EPA/600/R-93/132
August 1993
Environmental Fate Constants for
Organic Chemicals Under
Consideration for
EPA's Hazardous Waste identification Projects
Compiled and edited by
Heinz P. Kollig
Contributors: J. Jackson Ellington
Samuel W. Karickhoff
Brenda E. Kitchens
Heinz P. Kollig
J. MacArthur Long
Eric J. Weber
N. Lee Wolfe
Environmental Research Laboratory
Office of Research and Development
U.S. Environmental Protection Agency
Athens, GA 30605-2720
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DISCLAIMER
The information in this document has been funded by the United States
Environmental Protection Agency. It has been subjected to the Agency's peer and
administrative review and it has been approved for publication as an EPA document.
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TECHNICAL REPORT DATA.
(Please read Instructions on the reverse before c'ompiet
1. REPORT NO. 2.
EPA/600/R-93/132
3.
4. TITLE AND SUBTITLE
ENVIRONMENTAL FATE CONSTANTS FOR ORGANIC CHEMICALS
UNDER CONSIDERATION FOR EPA'S H7\ZARDOUS WASTE
IDENTIFICATION PROJECTS
5. REPORT DATE
August 1993
6. PERFORMING ORGANIZATION CODE
7. AUTHORISE
Heinz P. Kollig (Ed.)
8. PERFORMING ORGANIZATION REPORT NO.
9. PERFORMING ORGANIZATION NAME AND ADDRESS
Environmental Research Laboratory
U.S. Environmental Protection Agency
Athens GA 30605-2720
10. PROGRAM ELEMENT NO.
AC5D1A
11. CONTRACT/GRANT NO.
12. SPONSORING AGENCY NAME AND ADDRESS
Environmental Research Laboratory - Athens, GA
Office of Research and Development
U.S. Environmental Protection Agency
Athens GA 30605-2720
13. TYPE OF REPORT AND PERIOD COVERED
14. SPONSORING AGENCY CODE
KPA/600/01
15. SUPPLEMENTARY NOTES
16. ABSTRACT
Under Section 301 of the Resource Conservation and Recovery Act (RCRA), EPA's
Office of Solid Waste is in the process of identifying chemicals to be considered in
projects called the hazardous waste identification projects. At this time, there are
some 200 chemical chemical constituents identified in these projects. This publica-
tion addresses environmental fate constants and chemical hydrolysis pathways for the
189 organic chemicals already identified. Chemical hydrolysis rate constants for
parent compound and products including structural presentation of the pathways are
presented. Redox rate constants are given for selected compounds. Sorption coeffi-
cients are presented for parents and products in terms of the octanol/water partition
coefficient and the organic-carbon-normalized sediment/water partition coefficient.
The ionization constant is given when this process affects sorption in the environ-
mental 'pH range.
17. KEY WORDS AND DOCUMENT ANALYSIS
a. DESCRIPTORS
b.IDENTIFIERS/OPEN ENDED TERMS
c. cosati Field/Group
Hazardous waste
Pollutant fate constants
Hydrolysis rates
Sorption coefficients
Oxidation-reduction rates
Partition coefficients
18. DISTRIBUTION STATEMENT
RELEASE TO PUBLIC
19. SECURITY CLASS (This Report}
UNCLASSIFIED
j
21. no. of pages
183
20. SECURITY CLASS /This page)
UNCLASSIFIED
22. PRICE
EPA Form 2220-1 (R«v. 4-77! previous edition is obsolctj
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FOREWORD
As it becomes more and more obvious that many thousands of potentially hazardous
manmade chemicals find their way into ambient environments, the need for a
comprehensive understanding of the distribution of chemicals and their transport and
transformation reaches a higher level of importance. As part of this Laboratory's research
on the occurrence, movement, transformation, impact, and control of chemical
contaminants, the Chemistry Branch and the Measurements Branch determine the
occurrence of unexpected organic chemicals in the environment, define mechanisms of
transport and abiotic transformation, and develop and apply advanced methods to predict
and measure physical and chemical transformation and equilibrium constants for use in
exposure assessment.
Under Section 301 of the Resources Conservation and Recovery Act (RCRA), EPA's
Office of Solid Waste is required to develop and promulgate criteria for identifying and
listing hazardous wastes, taking into account, among other factors, persistence and
degradability in the environment of selected chemicals. A requirement of the legislation
is for EPA to take an initial step toward defining wastes that do not merit regulation
under Subtitle C of RCRA and can be managed under other regimes. For establishing
exemption criteria, the Agency has selected some 200 chemical constituents that may
occur in the various wastes. This report explains some of the means by which these
chemicals may be transformed and provides hydrolysis degradation pathways and fate
constants for the selected chemicals.
Rosemarie C. Russo, Ph.D.
Director
Environmental Research Laboratory
Athens, Georgia
iii
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ABSTRACT
Under Section 301 of the Resource Conservation and Recovery Act (RCRA), EPA's
Office of Solid Waste is in the process of identifying chemicals to be considered in projects
called the Hazardous Waste Identification Projects. This publication addresses the 189
organics already identified in these projects. The environmental fate constants and the
chemical hydrolysis pathways of these chemicals are listed. Chemical hydrolysis rate
constants for parent compounds and products including structural presentation of the
pathways are presented. Redox rate constants are given for selected compounds.
Sorption coefficients are presented for parents and products in terms of the octanol/water
partition coefficient and the organic-carbon-normalized sediment/water partition
coefficient. The ionization constant is given when this process affects sorption in the
environmental pH range.
iv
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Table
of Contents
Parti
Introduction
Hydrolysis
General
^^iiphotics 6
Siffiptc hCllQ£a%Cl$G(ji $
Polyhalogenated aliphatics 7
O/^fo/wpAospAonw Esters S
Carboxylic Acid Esters
Amides
Sorption 10
Neutral Organic Compunds 10
Ionizable Organic Compounds II
Estimated data 13
Redox 14
Abiotic Redox Transformations of Organic Compounds 14
Convention of Writing Redox Reactions IS
Reduction 15
Oxidation 16
Descriptions of Redox State of the System 16
Kinetics of Reaction in Heterogenous Systems 17
Calculation of Rate Constants..... 17
Reductive Processes 17
Nitroaromatics 17
Halogenated Hydrocarbons 17
Oxidative Processes ....... 18
Aldehydes 18
Amines 18
Table 1 19
Table 2 53
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Part 2
1. Acenaphthene 61
2. Acetone 61
3.- Acetonitrile 62
4. Acetophenone 63
5. Acrolein 63
6. Acrylaxnide 64
7. Acrylonitrile 64
8. Aldrin 65
9. Aniline 65
11. Aramite 66
14. Benz [a] anthracene 67
15. Benzene 67
16. SgqzIdine.........«..«..•••»*•.. 68
17. Benzo[6]fluoranthene[[[ 68
18. Benzo[a]pyrene 69
19« Benzotrichlonde 69
20. Benzyl alcohol 70
21. Benzyl chloride 70
23. fiis(2-chloroethyl)ether 71
24. j?is(2-chloroisopropyl)ether [[[ 72
25. fiis(2-ethylhexyl)phthalate 73
26. Bromodichloromethane 74
27. Bromomethane 74
28. Butanol 75
29. Butyl benzyl phthalate[[[ 75
30. 2-sec-Butyl-4,6-dinitrophenol 76
32. Carbon disulfide 76
33. Carbon tetrachloride 77
34. Chlordane 77
35. p-Chloroaniline 78
36. Chlorobenzene 78
37. Chlorobenzilate 79
38. 2-Chloro-l,3-butadiene 80
39. Chlorodibromomethane[[[ 80
40. Chloroform 81
41., Chloromethane 81
42. 2-Chlorophenol aaaaaMaaa«*M«aM«a«aaaaaaaa*»«*«a«aaa*aMaaa«aMaa«aaa«aaaaaaaaaaaaaaaa««aaa«aaaaaaaaa*aa«aa 82
43. 3-Chloropropene aaaaaaaaaaaaaaaaaaaaacaaaaaaMaHMaaaaaaaaaaaaaaaaaaaatMaaaaaaaaaaaaaaaaaaaaaaaaaaataaaat 82
45. Chrysene[[[ 83
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Cyanide 85
2,4-Dichlorophenoxyacetic acid 86
. DDD ................... ... ............. 86
. DDE 87
. p,p'-DDT 87
Diallate [[[ 88
Dibenz[a,&]anthracene[[[ 88
1,2-Dibromo-3-chloropropane 89
Dibromomethane 90
1,2-Dichlorobenzene 90
. 1,4-Dichlorobenzene 91
3,3'-Dichlorobenzidine 91
Dichlorodifluoromethane 92
1.1-Dichloroethane 92
1.2-Dichloroethane 93
1.1-Dichloroethylen e 94
cis-1,2-Dichloroethylene 94
trans-1,2-DichIoroethylene 95
Dichloromethane 95
2,4-Dichlorophenol 95
1.2-Dichloropropane 96
1.3-Dichlor opropene 97
Dieldrin 98
Diethyl phthalate 99
Diethylstilbestrol 100
Dimethoate (opposite page) 100
3,3'-Dimethoxybenzidiiie 102
7,12-Dimethylbenz[a]anthracene 102
3,3'-Dimethylbenzidine 103
2.4-Dimethylphenol 103
Dimethyl phthalate 104
1.3-Dinitrobenzene 105
2.4-Dinitrophenol 105
. 2,4-Dinitrotoluene 106
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96.
97.
98.
99.
100.
101.
102.
103.
104.
105.
106.
107.
108.
109.
110.
111.
112.
113.
114.
115.
116.
117.
118.
119.
120.
121.
122.
123.
124.
125.
126.
127.
128.
129.
130.
132.
134.
135.
136.
137.
138.
139.
140.
141.
Disulfoton ....
Endosulfan..
Endrin
Epichlorohydrin
2-Ethoxyethanol
Ethyl acetate
Ethylbenzene
Ethyl ether
Ethyl methacrylate
Ethyl methanesulfonate
Ethylene dibromide
Famphur
Fluoranthene
Fluorene
Formic acid
Fur an
2,3,7,8-TCDFuran
1^,3,7,8-PeCDFuran.
2,3,4,7,8-PeCDFuran
2,3,7,8-HxCDFurans ....
2,3,7,8-HpCDFurana
OCDF
Heptachlor
Heptachlor epoxide....
Hexachlorobenzene...
Hexachlorobutadiene
alpha-HCH
beta-HCH
Hexachlorocyclopentadiene
Hexachloroethane
Hexachlorophene
Indeno [ 1,2,3-ccflpyrene
Isobutyl alcohol
Isophorone
Kepone
gamma-HCH
Methacrylonitrile
Methanol
Methoxychlor
3-Methylcholanthrene
Methyl ethyl ketone.....
Methyl isobutyl ketone
Methyl methacrylate....
Methyl parathion
aaaaaaaaaaaMaaaaaaaaaaaaaa'
aMaaaaaiNiMMaaiMtaHtMaaaaaaiMaaaaiaaaaaaaaaaaaaa
•taa«aaM»ta«
MaaaaaaaaaMaaaaaaaaaaaaaaaaaaaaaaaaaaaaaMaaaaaaMaaaaataaaaaaaaaaaaaaa
•aaaaaaNaataafaaaaaaaaataaaaaaaaaaaavMaaaaaaaaaaaaMaamaaaaaaaaaaaaaa
•aaaMa«aaaaMaMaaaa*»aaaaaaaM«Haat«aaaaaMaa**aaaa«aaa«aaaaaa«aaa»»aa
aaMaaaaaaaaaaaa—aaaaaaaaaaaaaaaaaaawaaaaaaaaaaaaaaaaaaaaaaaa
MtaMaaaaaaaaaMa*aaaaa«aaaaaa«aaaaaaaaaaaaaaaMa«aaaaaaaaaa«aa«««aaaaa«
112
113
114
115
116
116
117
117
118
119
120
121
122
122
123
123
124
124
125
125
126
126
127
128
129
129
130
131
132
132
133
133
134
134
135
135
136
137
137
138
138
139
139
140
viii
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I'tA* 11 apiiviicUvIlv JL*±1
143. 2-Naphthylamine 141
145. Nitrobenzene[[[ 142
146. 2-Nitropropane 142
147. iV-Nitroso-di-re-butyiamine 143
148. iV-Nitrosodiethylamine 143
149. iV-Nitrosodimethylamine 144
150. iV-Nitrosodiphenylamine 144
151. iV-Nitroso-di-rc-propylamine 145
152. iV-Nitrosomethylethylamine 145
153. iV-Nitrosopiperidlne 146
154. iV-Nitrosopyrrolidine 146
155. Octamethyl pyrophosphoramide 147
156. Parathion [[[ 148
157. Pentachlorobenzene [[[ 149
158. Pentachloronitrobenzene[[[ 149
159. . Pentachlorophenol 150
160. Phenol[[[ 150
161. Phenylenediamine 150
162. Phorate 151
163. Phthalic anhydride 152
164. Polychlorinated biphenyls 152
165. Pronamide 153
166. Pyrene 153
167. Pyridine •••••••••••¦•••••••••¦¦••••••••••••••••••••a*154
168. Safrole 154
171. Strychnine[[[ 155
172. Styrene 155
173. 1,2,4,5-Tetrachlorobenzene 156
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190
191
192,
193
194
195.
196,
197,
198,
199,
201.
202.
Trichloroethyiene 166
Trichlorofluorometh hug 166
2.4.5-Trichloropheno l .. 167
2.4.6-Trichlorophenol 167
2,4,5-Trichlorophenoxyacetic acid 168
2-(2,4,5-Trichlorophenoxy)propionic acid (Silvez)............................. 168
1,2,3-Trichloropropane 169
1,1,2-Trichloro-l ,2,2-trifluoroethane 170
1,3,5-Trinitrobenzene 170
7Hs(2,3-dibromopropyl)phosphate 171
Vinyl chloride 172
Xylenes 172
x
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Parti 1
Introduction
Assessment of potential risk posed to humans by man-made chemicals in the environment
requires the prediction of environmental concentrations of those chemicals under various
environmental reaction conditions. Whether mathematical models or other assessment
techniques are employed, knowledge of equilibrium and kinetic constants (fate constants)
is required to predict the transport and transformation of these chemicals.
Under section 301 of the Resource Conservation and Recovery Act (RCRA), EPA's Office of
Solid Waste (OSW) has identified wastes that may pose a substantial hazard to human
health and the environment. RCRA requires that EPA develop and promulgate criteria
for identifying and listing hazardous wastes, taking into account, among other factors,
persistence and degradability in the environment of selected chemicals.
EPA continues to believe that the Agency must assure continuity of the hazardous waste
program while developing appropriate revisions. While fully preserving existing hazardous
waste identification rules, EPA is considering alternatives to take an initial step towards
defining wastes that do no merit regulation under Subtitle C and that can and will be
safely managed under other regulatory regimes.
EPA plans to hold a series of public meetings to solicit input on how best to insure that
waste mixtures containing hazardous wastes and wastes derived from the treatment,
storage or disposal of hazardous wastes do not pose unreasonable risks to health and the
environment. This effort will complement EPA's ongoing program to improve RCRA
regulations.
In the course of developing appropriate revisions, OSW is in the process of identifying
chemicals to be considered in projects called the Hazardous Waste Identification Projects.
At this time, there are some 200 chemicals contituents identified in these projects. The
environment fate constants and the chemical hydrolysis pathways of the 189 organics are
listed in Part I and Part II of this report, respectively. Inorganic compounds are not
addressed in this publication.
For all selected organic compounds, OSW requested that the Environmental Research
Laboratory-Athens (ERL-Athens):
a) identify those that do not hydrolyze.
b) identify those that do hydrolyze and list products of degradation including hydrolysis
rate constants for parents and intermediates obtained either through laboratory
experiments at ERL-Athens, literature searches, or pathway analyses.
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2
Fate Constants for Hazardous Waste identification
c) obtain sorption data as the organic-carbon-normalized sediment-water partition
coefficient either through laboratory experiments at ERL-Athens, literature searches,
or computational techniques.
d) to the extent that current scientific knowledge will permit, identify those that will be
subject to other important degradation reactions and identify products of these
reactions including rate constants.
For compounds identified as having no hydrolyzable functional group (NHFG), hydrolysis
will not occur by abiotic reaction pathways in the pH range of 5 to 9 at 25°C.
The compounds identified as having non-labile functional groups (NLFG) will not
hydrolyze to any reasonable extent. Although a molecule with a non-labile functional
group contains one or more heteroatoms, they react so slowly over the pH range of 5 to 9
at 25°C, that their half-lives will be greater than 50 years, if they react at all.
Polychlorinated biphenyls (PCBs) have been addressed here only as a class because of the
many different congeners of these compounds. The given Chemical Abstract Service
number 1336-36-3 is the number for the general class of Aroclors without designating any
specific Aroclor. Because PCBs will not hydrolyze to any reasonable extent, our Pathway
Analysis Team classified them as non-labile. The sorptive capacity, however, will be
different from congener to congener. We have found reported log K^, values ranging from
2.59 to 11.20. Therefore, a single sorption value for the class of Aroclors was not
assigned.
The chemical hydrolysis pathways of compounds with negative boiling points that exist as
gases at room temperature were not addressed in this report.
Some compounds may exist in the environment as ionized species. The transformation
pathways show these species in the neutral form for better identification. It should be
understood that both the persistence and mobility of a chemical in the environment is
influenced by many environmental factors that may change from environment to environ-
ment. The values in this document are for those conditions specified in the references.
A team of EPA scientists met several times to discuss the rates and probable pathways of
transformation for hydrolysis and redox reactions. The methods used to arrive at the
reaction products were based primarily on the team's experience with similar compounds,
their knowledge of the theory of these processes, and their understanding of structure-
activity relationships. For hydrolysis, the team's decisions are identified in Table 1 with a
zero in the Reference column. Final stable products are identified as containing either no
hydrolyzable functional group (NHFG) or a non-labile functional group (NLFG) in the
Comment column.
Literature searches were conducted afterwards to find needed fate data for the intermedi-
ate products of hydrolysis. If the literature failed to provide the required data, they were
determined in the laboratory for some compounds.
This report is composed of two parts. Part I includes text and data on chemical hydrolysis,
sorption, and redox reactions. In the hydrolysis section hydrolysis kinetics are elucidated
for the chemical classes of halogenated aliphatics, organophosphorus esters, carboxylic acid
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Parti
esters, amides, carbamates and nitrites. In the sorption section, the sorption of neutral and
ionizable organic compounds is addressed including computational techniques. In the
redox section, the kinetics of the unexplored area of the heterogeneous redox reactions is
elucidated. Part I concludes with a table listing hydrolysis products (intermediate and
final) including rate constants for parents and intermediates, and sorption data for parents
and for intermediate and final products, and a table listing computed redox rate constants
at different levels of organic carbon for selected halogenated aliphatics and nitroaromatics.
Part II includes the chemical structures of all organic compounds under consideration in
the projects and the pathways of chemical hydrolysis of these compounds that undergo this
transformation. When a compound was identified as NHFG, the text with the structure will
say that the compound will not hydrolyze. When a compound was identified as NLFG, the
text with the structure will say that the compound will not hydrolyze to any reasonable
extent. When a compound might be subject to other abiotic transformation processes, the
text with the structure will point this out; however, these processes have been identified.
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Parti 5
Hydrolysis
General
In general, hydrolysis is a bond-making, bond-breaking process in which a molecule, RX,
reacts with water forming a new R-0 bond with the oxygen atom from water and cleaving
an R-X bond in the original molecule. One possible pathway is the direct displacement of X'
with HO' as shown in Equation 1.
RX + HjO ~ ROH + HX (1)
The detailed mechanisms of hydrolytic processes are well defined and have been shown to
involve the formation of intermediates such as protonated species, anions and carbonium
ions, as well as combinations of these intermediates.
Generally, hydrolysis of organic compounds in water under pH-buffered conditions is first-
order in the concentration of the organic species ([RX]), where the rate of hydrolysis
(d[RX]/
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6
Fate Constants for Hazardous Waste Identification
tions of the ith and theyth pair of general acids and bases in the reaction mixture, respective-
ly.
In Table 1, ka, kb, and kn values are reported for the particular chemical at 25°C (+/-4°C). A
half-life at 25°C can be calculated by using Equation 4 to calculate followed by Equation
3 to calculate the time at 50% hydrolysis. Concentration and time units used are molar (M)
and year (Y), respectively. Products of hydrolysis are listed indented under the parent
compound, e.g., acetonitrile (parent): acetamide is the first hydrolysis product and it then
becomes an intermediate by hydrolyzing to a secondary product, acetic acid. Both products
are indented according to the order of their appearance in the hydrolysis pathway of the
original parent.
Hydrolysis rate constants that were reported in the literature at an elevated temperature
were reanalyzed with RATE28 to extrapolate the values to 25°C. These reanalyzed values are
identified by RATE in the Comment column. Those compounds that were identified as non-
hydrolyzable or non-labile were designated as rNHFG' and 'NLFG', respectively, in the
Comment column.
Halogenated Aliphatics
Simple halogenated aliphatics
Hydrolysis of the simple halogenated aliphatics (halogen substitution at one carbon atom) is
generally pH independent, resulting in the formation of alcohols by nucleophilic substitution
with water (Equation 1). Although a number of the simple halogenated aliphatics are
susceptible to base-mediated hydrolysis, the rate term for the base-medi-
ated process will not contribute to the overall hydrolysis rate under environmental conditions.
The halogenated methanes, except for the trihalomethanes, hydrolyze by direct nucleophilic
displacement by water (S>j2 mechanism). An increase in the number of halogen substituents
on carbon increases the hydrolysis half-life because of the greater steric bulk about the site
of nucleophilic attack. The type of halogen substituent also affects reactivity. For example,
hydrolysis data indicate that the fluorinated aliphatics are much more stable than the
chlorinated aliphatics, which in turn are more stable than the brominated aliphatics (F > CI
> Br). This trend in reactivity reflects the strength of the carbon-halogen bond that is broken
in the nucleophilic substitution reaction.
Hydrolysis of the trihalomethanes, or haloforms, is thought to occur initially by proton
abstraction and subsequent formation of the carbene, which reacts with HO- to form carbon
monoxide and chloride ion:41
CHCI3 + HO"
"CCh
:CCl2 + 2 HO"
•CCI3 + H20
:CCIj + cr
co + 2cr + h2o
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Parti 7
In contrast to the halogenated methanes which have hydrolysis half-lives on the order of
years, the hydrolysis half-lives for allylic and benzylic halides are on the order of minuteB to
hours. The hydrolysis of these chemicals occurs through an indirect nucleophilic displace-
ment by water (SnI mechanism). The dramatic increase in reactivity is due to the structural
features of these compounds that allow for delocalization, and thus, stabilization, of the
carbonium ion intermediate. Resonance structures can be drawn for the allylic and benzyl
carbonium ions that delocalize the positive charge over several carbon atoms.
The lack of reactivity observed for vinyl halides and halogenated aromatics is a reflection of
the high energy pathway required for nucleophilic substitution at vinylic and aromatic
carbons. Vinyl and phenyl carbonium ions have been observed, but their formation requires
very reactive leaving groups.
Polyhalogenated aliphatics
The hydrolysis kinetics for the polyhalogenated ethanes and propanes are somewhat more
complex than for the simple halogenated aliphatics. In addition to nucleophilic substitution
reactions, degradation of these compounds can occur through the base-mediated loss of HX.
Depending on structure type, elimination or dehydrohalogenation may be the dominant
reaction pathway at pITs characteristic of ambient environments. The loss of HX occurs
through a bimolecular elimination (E2) reaction in which abstraction of the hydrogen beta
to the halogen (X) occurs simultaneously with cleavage of the C-X bond:
^"OH
-c-c- * X- + "iO
This process often results in the formation of halogenated alkenes, which can be more
persistent and of more concern than substitution products42.
The distribution of reaction products resulting from the hydrolytic degradation of the
polyhalogenated ethanes and propanes will depend on the relative rates for the nucleophilic
substitution and dehydrohalogenation reaction pathways. Furthermore, because dehydro-
halogenation is pH dependent, product distribution will also be pH dependent.
A wide range of reactivity is observed for these compounds; the environmental hydrolysis
half-lives in years range over 7 orders of magnitude. For a number of the polyhalogenated
aliphatics, it is apparent that both neutral and base-mediated hydrolysis will occur at
ambient environmental pH values and that the relative contributions of these processes will
be dependent on the degree and pattern of halogen substitution.
As with nucleophilic substitution reactions, rates of dehydrohalogenation reactions will be
dependent on the strength of the C-X bond being broken in the elimination process.
Accordingly, it is expected that the ease of elimination of X will follow the series Br> CI > F.
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8
Fate Constants for Hazardous Waste Identification
Epoxides
The hydrolysis of epoxides is pH dependent and can occur through acid-, neutral-, or base-
promoted processes. Because the acid and neutral processes dominate over ambient environ-
mental pH ranges, the base-mediated process can often be ignored. The products resulting
from the hydrolysis of epoxides are diols, and to a lesser extent, rearrangement products:
A ^ h20 fr?
Ft,—
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Part I 9
products proceeds at a rate approximately a factor of 10 less than that of the triester.
Hydrolysis of the resulting monoalkyl ester (dianion) proceeds at a rate of approximately one
half that of the triester. Hydrolysis of the monoester has been shown to occur through
nucleophilic attack on the phosphorus rather than carbon-oxygen cleavage86.
Carboxyllc Acid Esters
Hydrolysis of carboxylic acid esters results in the formation of a carboxylic acid and an
alcohol:
Hydrolysis mechanisms of carboxylic acid esters have been thoroughly investigated. Although
nine distinct mechanisms have been proposed45, our comments will be limited to the two most
common mechanisms involving acyl-oxygen bond cleavage by acid catalysis (Aac2) and base
mediation (BAC2). Hydrolysis via the Aac2 mechanism involves initial protonation of the
carbonyl oxygen. Protonation polarizes the carbonyl group, removing electron density from
the carbon atom and making it more electrophilic and thus more susceptible to nucleophilic
addition by water. The base-mediated mechanism (BAC2) proceeds via the direct nucleophilic
addition of HO- to the carbonyl group. Base mediation occurs because the hydroxide ion is
a stronger nucleophile than water. Although neutral hydrolysis of carboxylic acid esters does
occur, the base-mediated reaction will be the dominant pathway in most natural waters.
Generally, acid hydrolysis will dominate in acidic waters with pH values below 4.
Both electronic and steric effects can significantly alter the reactivity of carboxylic acid esters.
Because the acid-catalyzed process for both aliphatic and aromatic esters is relatively insensi-
tive to structural changes, observed changes in the magnitude of k^, with structure are due
primarily to changes of kb, and to a lesser extent, kn. Based on the mechanism for base
mediation (BAC2), we would expect that electronic factors that enhance the electrophilicity of
the carbon atom of the carbonyl group would make it more susceptible to nucleophilic attack
by HO~. The electron-withdrawing groups can be substituents of either the acyl group
(RC(O)} or the alcohol portion of the ester.
Hydrolytic degradation of amides results in the formation of a carboxylic acid and an amine:
F^-C—O—R2 + HzO
R1-C—OH + HOR2
Amides
+
r
HN—R3
In general, amides are much less reactive towards hydrolysis than esters. Typically, half-
lives for amides at ambient environmental conditions are measured in hundreds to thousands
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10
Fate Constants for Hazardous Waste Identification
of years8. This observation can be explained by the ground-state stabilization of the carbonyl
group by the electron donating properties of the nitrogen atom:
This stabilization is lost in the transition state leading to the formation of the tetrahedral
intermediate. The result is that the hydrolysis of amides generally requires base or acid
catalysis, both of which can compete at neutral pH.
Carbamates
A carbamate is hydrolyzed to an alcohol, carbon dioxide, and an amine:
Carbamates are susceptible to acid, neutral and base hydrolysis, although in most cases, base
hydrolysis will dominate at environmental conditions. In an analogous manner to carboxylic
acid ester and amide hydrolysis, electron-withdrawing substituents on either oxygen or
nitrogen will accelerate the rate of hydrolysis. The most dramatic differences in reactivities
are observed when the hydrolysis half-lives of primary (R^H, R^alkyl) and secondary
(R^alkyl, R2=alkyl) carbamates are compared. The primary carbamates hydrolyze at rates
that are approximately 6 to 7 orders of magnitude faster than the corresponding secondary
carbamates.
Nitriles are hydrolyzed to give a carboxylic acid and ammonium ion. Hydrolysis occurs
through the intermediate amide:
+
Nitriles
Base-mediated hydrolysis appears to be the dominant hydrolysis pathway at pH 7.
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Parti 11
Sorption
Neutral Organic Compounds
Partitioning between water and natural soils, sediments, and aquifer materials is an
important process affecting transformation rates, toxicity, and the ultimate disposition of
organic chemicals in the environment. Research focusing on the partitioning of neutral
organic compounds has shown that adsorption of these compounds is usually controlled by
hydrophobic interactions. As a result, the affinity that a natural sorbent has for neutral
organic solutes, in most cases, can be reliably estimated from characterization (quantification)
of the hydrophobicity of chemical and the sorbent. Organic carbon content has been used
almost exclusively as a measure of the hydrophobic nature of natural sedimentary material
(organic matter or volatile solids content has also been used but not as widely). To
quantitatively characterize the hydrophobic nature of organic compounds, researchers have
used various measurable parameters, including octanol-water partition coefficients (^J,
water solubility (corrected for crystal energy), reverse phase HPLC retention, and topological
parameters of the compounds such as calculated surface area. Generally, octanol-water
partition coefficients have been used extensively for estimating the partitioning of organic
compounds to sedimentary materials.
lonizable Organic Compounds
Predicting the partitioning of ionizable organic compounds is not as straightforward as for
the neutral compounds. These compounds, whether they are acids or bases, can exist as ions
in solution depending upon the pH of the solution according to the following equations. For
acids:
K = (5)
[HA]
and bases:
K - (6)
[HB-]
where [H+] is the hydrogen ion activity, [HA] is the neutral organic acid activity (or
concentration), [A ] is the organic acid anion activity, [B] is the neutral organic base activity,
[HB+] is the protonated organic base activity, and K0 is the acid dissociation or ionization
constant.
In general, more effort has been expended investigating the sorption of organic acids than the
sorption of organic bases. For organic acids, adsorption can be modeled to sediments, soils,
and aquifer materials in a similar manner to that of the neutral compounds, after taking
into account ionization, as long as the pH is not more than one unit above the pK0 of the
compound48.
Compounds with low pK0 values are more problematic. Adsorption of these compounds occurs
predominantly by the anionic species through modified hydrophobic interactions47. Therefore,
an estimate of a partition coefficient from the of the neutral species would significantly
-------
12
Fate Constants for Hazardous Waste Identification
overestimate the magnitude of adsorption. Jafvert et al.48 and Jafvert47 have investigated the
partitioning behavior of these and similar compounds in the octanol-water system and in sediment-
and soil-water systems. For example, Jafvert47 has reported on the sediment-water distribu-
tion of silvex in 13 soils or sediments. If the partition coefficients (in which the pH of the
slurry is greater than 7) are regressed versus the fraction organic carbon, a value of log Kx
= 1.8 is obtained for the organic-carbon-normalized partition coefficient, K^. The log of
the neutral form of silvex is 3.8. Similar results for pentachlorophenol and 4-chloro-a-(4-
chlorophenyl)benzeneacetic acid (DDA) suggest that the partition coefficient (at pH 7.0) of the
anionic form of these compounds is approximately two orders of magnitude less than the
respective values of the neutral form of these compounds.
Unlike anionic organic compounds, which partition more weakly than their neutral counter-
parts, organic cations tend to partition more strongly than the corresponding unprotonated
bases. Also, unlike organic anions, which partition largely through modified hydrophobic
interactions, the organic cations can undergo cation (or ligand) exchange reactions. Pyridine,
for example, is an organic base that has a pKa value of 5.3. At pH 7, a small fraction (2.2%)
will exist as an organic cation in aqueous solution. Because the cationic species is expected
to adsorb more strongly to most natural soils, sediments, and aquifer materials than the
neutral species, an organic-carbon-normalized partition coefficient (Kx) may severely
underestimate the adsorption of this compound at near-neutral pH. Because no predictive
methods exist for describing the partitioning of organic cations to natural matrices, however,
the organic-carbon-normalized partition coefficient calculated from the of the neutral
species (not accounting for ionization) is given in Table 1. For virtually every sediment and
aquifer material, this constant will underpredict the true magnitude of adsorption of these
compounds, with the error intensifying as the organic carbon content of a sediment or aquifer
material decreases.
For neutral compounds and organic bases with pKa values below 6, the organic-carbon-
normalized partition coefficients in Table 1 have been calculated using the relationship,
log K<>c = - 0.32 (7)
given by Hassett et al.49 This correlation was calculated from adsorption isotherms of 13
organic chemicals, representing several classes of compounds, using 14 different sediment and
soil samples. This correlation adequately predicts partitioning of several classes of organic
compounds, including chlorinated and nonchlorinated aromatic and alkyl hydrocarbons. Use
of this correlation will generally be valid for soils, sediments, and aquifer materials that have
organic carbon contents greater than 0.1%.
For organic acids, the pK„ must be considered in the computation of the Kk. The following
relationships were used according to the range of pKa values:
pKa > 9: = 1.05
(8)
-------
Parti 13
6 < pK0 < 9: = 1.05C82)
(0.82)
(9)
which simplifies at pH 7 to:
K
OC
1.05 x 10"7 x Kfwn)
10"7 + Ka
(10)
pKc < 6: log = log Kw - 2
(11)
For organic bases, the pKa value was considered in the computation of the Kx, where pKa =
14-pKb. Equation (7) was used for compounds with pKa values of less than 6. For organic
bases with pKa values larger than 6, no Kx values were calculated because the uncertainty
is too great. When a Kx value was needed for a complex ion with successive ionization
constants, the first ionization constant ipKj) was used in the computation of the Kx value.
All ionization constants were computed with SPARC29.
Estimated data
Most of the log K^. values in Table 1 were computed with QSAR4 and SPARC29. QSAR is an
interactive chemical database and hazardous assessment system designed to provide basic
information for the evaluation of the fate and effects of chemicals in the environment. The
QSAR4 system is a composite of databases containing measured values obtained from the
literature and a state-of-the-art QSAR model library capable of estimating chemical
properties, behavior, and toxicity, based on conventional estimation techniques, many of
which were derived from the work of Lyman et al.60 The QSAR system contains automated
estimation routines for 13 properties based upon modified structure-activity correlations.
SPARC29 is a computational expert system that predicts chemical reactivity. The system has
the capability of crossing chemical boundaries to cover all organic chemicals and uses
algorithms based on fundamental chemical structure theory to estimate parameters. SPARC
quantifies reactivity by classifying molecular structures and selecting appropriate
"mechanistic" models. It uses an approach that combines principles of quantitative structure-
activity relationships, linear free energy theory (LFET), and perturbed molecular orbital
(PMO) or quantum chemistry theory. In general, SPARC utilizes LFET to compute thermal
properties and PMO theory to describe quantum effects such as delocalization energies or
polarizabilities of it electrons.
For example, SPARC computes the log of the octanol-water partition coefficient from activity
coefficients in the octanol (y") and water (y~ ) phases:
-------
14
Fate Constants for Hazardous Waste Identification
Kow = + J°8 rjr- (12)
Yo M*
where M0 and Mw are solvent molecularities of octanol and water, respectively. Activity
coefficients for either solvent or solute are computed by solvation models that are built from
structural constituents requiring no data besides the structures.
A goal for SPARC is to compute log K^, values that are as accurate as values obtained
experimentally for a fraction of the cost required to measure them. Because SPARC does not
depend on laboratory measurements conducted on compounds with structures closely related
to that of the solute of interest, it does not have the inherent problems of phase separation
encountered in measuring highly hydrophobic compounds (log > 5). For these compounds,
SPARC'S computed value should, therefore, be more reliable than a measured one.
Redox
Abiotic Redox Transformations of Organic Compounds
Abiotic redox reactions will not generally mineralize large organic molecules, but the transfor-
mations will result in daughter products with different chemical and physical properties81.
Furthermore, abiotic transformations can convert bio-resistant compounds to more bio-
susceptible compounds. For example, redox reactions can result in oxidation or reduction of
key functional groups on molecules that will render them labile to microbial transformations
and ultimately mineralization or conversion to other environmentally innocuous components.
A large number of functional groups on organic compounds have been shown to undergo
abiotic reduction under ambient environmental conditions. In general, these redox transfor-
mations encompass almost all chemical functional groups, utilize a large number of organic
and inorganic redox agents, and result in an almost unlimited number of products52.
Furthermore, the rates of redox reactions can be expected to span many orders of magnitude,
depending upon the reaction type and redox agents' activities. Unfortunately, only a few of
the reactions have been studied in enough detail to identify the system redox agents and
provide kinetics data.
It is not currently possible to address redox transformations for all the listed compounds in
soils, sediments and aquifer systems because of a lack of quantitative research in the area
of environmental redox reactions. For the few classes of compounds where detailed studies
have been carried out, it is possible to obtain reductive rate constants and apply them to
environmental systems83,84. In these detailed studies, kinetic expressions and the reducing
agents have been identified.
In this report, reduction of halogenated hydrocarbons and nitroaromatics, and the autooxida-
tion of aldehydes and amines are addressed. Estimated rate constants for halogenated
hydrocarbons and nitroaromatics are given in Table 2. These rate constants were computed
for soil-water systems in which the solids contained 1% and 0.02% organic carbon. The data
-------
Part I 15
clearly indicate the dependence of the reductive process on organic carbon. A 50-fold increase
in organic carbon from a concentration of 0.02% decreases the half-lives by about 4 orders of
magnitude for the halogenated hydrocarbons and about 1 order of magnitude for the
nitroaromatics. For the QSAR computations of the halogenated hydrocarbons, either
published sigma constants or estimated values were used. For the QSAR computations of
the nitroaromatics, published sigma constants were used except for parathion and methyl
parathion. For these two compounds, the sigma constants were estimated from 1-methoxy-p-
nitrobenzene. Rate constants for the nitroso compounds were not computed. However,
preliminary laboratory studies of some nitroso compounds indicated half-lives of less than 1
hour. It was not possible to identify products of degradation. We hope that the following will
give the reader some insight into this difficult and unexplored area of heterogeneous redox
reactions.
Convention of Writing Redox Reactions
In the environmental literature, as well as in organic chemistry textbooks, the definitions of
oxidation-reduction are often empirical and can result in ambiguities, especially when applied
across classes of compounds82. Reactions that form new bonds with hydrogen are often
referred to as reduction, whereas those forming new bonds with oxygen are often referred to
as oxidation. Although this system may hold for specific classes of compounds, it is not
generally applicable to the myriad of chemicals of environmental importance.
The overall reaction is not given because, for the most part, the activity of the reducing or
oxidizing agent responsible for the transformation is not known. Thus it is not possible to
sum up the two half-reactions and write the overall equation.
An unambiguous method for describing redox processes is to write the chemical equation for
each half-reaction with the reactants on the left and the products on the right, balancing the
equation by using hydrogen ions to provide needed hydrogen and hydroxide ions or water
molecules to provide needed oxygen atoms. Electrons are then added to balance the charge
(Figure 1). If electrons are added to the left side of the equation, it is a reduction reaction.
If electrons are added to the right side of the equation, it is an oxidation reaction. Examples
of half-reactions for reduction and oxidation are given below.
Reduction
Figure 1 shows two examples of reductive transformations. The first is a two-electron
transfer reaction for the reduction of 1,2-dichloroethane to ethene and chloride. The second
is a six-electron reduction of nitrobenzene, requiring six protons that gives aniline and water
as products.
-------
16 Fate Constants for Hazardous Waste Identification
u I_IU + 2e- *• HgC—CH2 + 2CI"
n2v",,vn2
Figure I.
Half-reactions for the reduction of 1,2-dichloroethane to
ethene and the reduction of nitrobenzene to aniline.
Oxidation
Figure 2 shows two examples of redox half-reactions. The first is a two-electron oxidation of
1,1,2-trichloroethylene to 1,1-dichloroacetic acid, chloride, and three protons. The second is
a two-electron oxidation of benzaldehyde to benzoic acid. In this reaction, water provides the
source of oxygen and results in two protons as a product.
ClgC^CHCI + 2H2O »- CfeHCC02H + Ql~ + 3H+ + 2e*
Figure 2. Half-reactions for the oxidation of 1,1,2-trichloro-
ethylene to 1,1-dichloroacetic acid and the oxidation
of benzaldehyde to benzoic acid.
Descriptions of Redox State of the System
Eh
When the Eh of the heterogenous system, as measured by a platinum electrode, is above Eh
50 mv (relative to Ag:AgCl), the reductive reaction does not occur for the halogenated
-------
Pari I 17
hydrocarbons and nitroaromatics65. When the Eh of the system is below 50 mv, the reaction
occurs and the rate of reaction is independent of the magnitude of the Eh.
pH
In general, in heterogenous systems, pH effects on the rates of abiotic reductions are
minimal. This is partly because the solids tend to buffer the pH of the system66. For
example, over the pH range of 5 to 9, the rate constant for reduction of nitrobenzene to
aniline was independent of pH. The same has been observed for the reduction of halogenated
hydrocarbons.
Kinetics of Reaction in Heterogenous Systems
To carry out abiotic reactions in heterogenous systems such as soils, sediments and aquifer
materials, requires an understanding of the kinetics of reaction. In these heterogenous
systems, sorption of the compounds to the solids will affect the overall kinetics of reaction.
A working model has been proposed to account for the observed kinetics of reduction of
compounds in these types of heterogenous systems54'66,56,88. The model, which is shown below,
assumes non-reactive and reactive sorptive sites on the solids.
P + S
kl
PS
k-1
Where P is pollutant concentration; S is sediment concentration (g/g); k1 and k.j are the
respective sorption-desorption rate constants to a non-reactive sink, P:S; k2 and k 2 are the
respective sorption-desorption rate constants to the reactive sink, P:R; kr is the first-order
rate constant for reduction at reactive solid sites.
Calculation of Rate Constants
Reductive Processes
Nitroaromatics
Rate constants for the reduction of nitroaromatics can be calculated using the SAR based on
Hammett sigma constants reported by Wolfe et al.66 This relation provides selected, observed
first-order disappearance rate constants for nitroaromatic compounds. These first-order rate
constants have been shown by Wolfe et al.66 to correlate with the organic carbon of the
system.
Halogenated hydrocarbons
Wolfe and co-workers67,68 developed a structure reactivity relationship that associates the
reductive disappearance rate constants of halogenated hydrocarbons in anoxic sediments with
readily available molecular descriptors. The correlation is based on disappearance rate
constants for the reductive transformation of 19 halogenated hydrocarbons. The compounds
-------
18
Fate Constants for Hazardous Waste Identification
span a large cross section of chemical structures that includes halogenated methanes,
ethanes, ethenes, and halogenated aromatics.
Wolfe and co-workers57,68 also corrected the rate constants for hexachloroethane for sorption.
These rate constants were obtained in 18 different sediment, soil and aquifer samples and
correlated with the organic carbon.
Oxidative Processes
Aldehydes
In general, aldehydes will undergo autooxidation to the corresponding carboxylic acids in the
presence of oxygen62,69. In sediments, soil and aquifer materials, aldehydes have been shown
to undergo such oxidations even under anoxic conditions. No comprehensive data base of rate
constants is available for these reactions and, furthermore, the autooxidation kinetics are too
complex to extrapolate precise rate constants from laboratory to field conditions.
These reactions have been observed for a large number of aldehydes and, based on this
qualitative data base, half-lives of less than 1 year are reasonable.
Amines
In general, amines undergo rapid autooxidation62,59. Their autooxidation mechanisms and
transformation kinetics are complicated and not well understood. In the presence of oxygen
in sediments and soils, they can form covalent bonds with the organic components of the
solids and thus become bound residues. Under anoxic conditions in sediments and soils,
however, they appear to be stable for long periods of time and tend not to bind irreversibly
to the organic matter associated with the organic carbon.
No comprehensive data base of rate constants for these types of reactions has been compiled
and, furthermore, the reaction kinetics are too complex to extrapolate precise rate constants
from the laboratory to field conditions.
Because reactions have been observed for a large number of amines, it is reasonable to
assume that these compounds will undergo autooxidation in the field. Based on the qualita-
tive data base, half-lives for this class of compounds will be less than 1 year.
-------
TABLE 1. Chemical hydrolysis rate constants and sorption data for organic compounds.
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
k.
K
K
References
Common Name
No.
LogK^
Log K,.
M'Y"
r'
M'Y'
Comment
Koc/Kc/k,,
1. Acenaphthene
83-32-9
3.75
4.07
0
0
0
NHFG
/ 4/ 0
2. Acetone (2-propanone)
67-64-1
-0.588
-0.268
0
0
0
NHFG
/ 4/ 0
3. Acetonitrile (methyl cyanide)
75-05-8
-0.714
-0.394
0
0
45
RATE
/ 4/ 24
Acetamide
60-35-5
-1.55
-1.23
2.6E2
0
1.5E3
/ 4/ 5
Acetic acid
64-19-7
-2.23
-0.234
0
0
0
NHFG
/ 4/ 0
(pK.-4.65)
Ammonia
7664-41-7
NA
NA
0
0
0
NHFG
/ 0/ 0
4. Acetophenone
98-86-2
1.26
1.58
0
0
0
NHFG
/ 4/ 0
5. Acrolein
107-02-8
-0.219
0.101
NG
6.68E8
NG
/ 4/ 30
3-Hydroxy-1 -propanal
2134-29-4
-1.3
-1.0
0
0
0
NHFG
/ 29/ 0
6. Acrylamide
79-06-1
•0.989
-0.669
31.5
1.8E-2
0
a
/ 4/ 6
Acrylic acid
79-10-7
-1.84
0.161
0
0
0
NHFG
/ 4/ 2
(pK.-4.13)
Ammonia
7664-41-7
NA
NA
0
0
0
NHFG
/ 0/ 0
7. Acrylonitrile
107-13-1
-0.089
0.231
5E2
0
5.2E3
RATE
/ 4/ 6
Acrylamide **
79-06-1
-0.989
-0.669
31.5
1.8E-2
0
a
/ 4/ 6
Acrylic acid
79-10-7
-1.84
0.161
0
0
0
NHFG
/ 4/ 2
(PK.-4.13)
Ammonia
7664-41-7
NA
NA
0
0
0
NHFG
/ 0/ 0
8. Aldrin
309-00-2
6.18
6.496
0
0
0
NLFG
/ 7/ 0
9. Aniline
62-53-3
0.595
0.915
0
0
0
NHFG
/ 4/ 0
(benzeneamine: pK„-9.3)
-------
ro
o
Common Name
Chemical
Abstract
Service
No.
Sorption
LogK^
Sorption
Log K„.
Chemical Hydrolysis
K *n K
MV r' M'Y1
Comment
References
K~/Ko./*h
10. Antimony (and compounds N.O-S.)
¦mmmsi
11. Aramite
140-57-8
5.2
5.5
0
7.7
6.0E4
ff
/ 29/
1 -Methyl-2-[p-(1,1 -dimethyl-
ethyl)phenoxy[ethylhydrogensulfite
1 -Methyl-2[p-(1,1 -dimethyl-
ethyl)phenoxy]ethanol
Sulfuric acid
1 -Methyl-2[p-(1,1 -dimethylethyl)-
phenoxyjethanol
2-Chloroethylhydrogensulfite
Sulfuric acid
2-Chloroethanol
Hydrochloric acid
Ethylene oxide
Ethylene glycol
2-Chloroethanol
Hydrochloric acid
Ethylene oxide
Ethylene glycol
NG
2416-30-0
7664-93-9
2416-30-0
NG
7664-93-9
107-07-3
7647-01-0
75-21-8
107-21-1
107-07-3
7647-01-0
75-21-8
107-21-1
3.15
NA
3.15
NA
-0.492
NA
-1.1
-1.5
-0.492
NA
-1.1
-1.5
3.47
NA
3.47
NA
-0.172
NA
-0.792
-1.2
-0.172
NA
-0.792
-1.2
0
0
0
0
0
0
0
0
2.9E5
0
0
0
2.9E5
0
7.7
0
0
0
7.7
6.0E40
3.9E-2
0
21
0
3.9E-2
0
21
0
6.0E4
0
0
0
6.0E4
0
3.2E5
0
0
0
3.2E5
0
0
0
gg
NLFG
NHFG
NLFG
gg
NHFG
NHFG
NHFG
NHFG
NHFG
/ / o
/ 4/ 0
/ 01 o
/ 4/ 0
/ / o
/ 0/ 0
/ 4/ 3
/ 0/ 0
/ 4/ 5
1 29/ 0
1 4/ 3
/ 0/ 0
/ 4/ 5
/ 29/ 0
12. Arsenic (and compounds N.O.S.)
13. Barium (and compounds N.O.S.)
7440-39-3
14. Benz[a]anthracene
56-55-3
5.34
5.66
0
0
0
NHFG
/ 4/ 0
15. Benzene
71-43-2
1.80
2.12
0
0
0
NHFG
/ 37/ 0
16. Benzidine
(pK|,~9-3)
92-87-5
1.26
1.58
0
0
0
NHFG
/ 4/ 0
17. Benzo[b]fluoranthene
205-99-2
5.8
6.12
0
0
0
NHFG
1 4/ 0
18. Benzo[a]pyrene
50-32-8
5.8
6.12
0
0
0
NHFG
/ 4/ 0
J
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
Log
Log
M-V
Y"
MV
Comment
KclK.IK
19. Benzotrichloride
98-07-7
4.06
4.38
0
2.0E6
0
1 29/ 5
Benzoic acid
65-85-0
-0.11
1.89
0
0
0
NHFG
/ 4/ 0
(pK.-4.18)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
20. Benzyl alcohol
100-51-6
0.78
1.10
0
0
0
NHFG
/ 4/ 0
(PK.-15.1)
21. Benzyl chloride
100-44-7
2.84
3.16
0
4.1 E2
0
RATE
/ 29/24
Benzyl alcohol **
100-51-6
0.78
1.10
0
0
0
NHFG
/ 4/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 o
22. BeryilUim (and compound* N.O.S.)
7440-41-7
23. S/s(2-chloroethyl)ether
111-44-4
0.80
1.12
0
0.23
0
/ 1/ 3
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
2-(2-chloroethoxy)ethanol
628-89-7
-0.186
-0.154
0
0.28
0
/ 4/ 3
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
S/s(2-hydroxyethyl)ether
111-46-6
-1.62
-1.30
0
0
0
NHFG
1 4/ 2
1,4-Dioxane **
123-91-1
-0.812
-0.492
0
0
0
NHFG
/ 4/ 2
24. 8/s(2-chloroi8opropyl)ether
39638-32-9
2.39
2.71
0
0
See Part II.
/ 4/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 o
(2-Hydroxyi9opropyl-2-chloro-
NG
2.7
3.0
b
1 29/ 0
i9opropyl)ether
S/s(2-hydroxyi8opropyl)
72986-46-0
1.1
1.4
0
0
0
NHFG
1 291 0
ether
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 0
-------
Fate Constants for Hazardous Waste Identification
o o o o
Oi O) 0> ^4-
C\J CM CM ^
5 o o o
o o o
o o
Tf o
O)
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o o o
^ O)
o o o o o
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o
LL
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CD O
I U-
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z z
o o o
U. U- LL
xxx
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o o
U. LL
X x
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Z Z
o o
LL 11.
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z z
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U- u.
x x
O
LL
X
10
«5
>»
8
2
z
75
o
>-
jf*-
CO
LU
CM
O LJJ O O
N
LU
O
in
o o o
(O
UJ
CM
O UJ o
(O
O O UJ o o
CO
o o o o
o
z
if
O)
o o o o o
o o o o
o
o o o o o
s *
«5
s
N
8
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CM
< < <
z z z
GO
o
|s
in
o
CM
CO
CO
in
o>
CM
CO
CM
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CO
N
CO
GO
1 .
h.
O
O
O
CO
7—
o
CM
o
S j
If
CO
hi
(£) ,. (O S
in ^ in cm
CM 10 CM V
h»
h.
< < <
00 ^
o <
r-» Z
§
o
00
CM
8 5 CO CO JJ;
o to fs, CM
CM
o
CM
a>
N.
N.
CO
o
CM
N-
cb
CO
00
1
N
N
5*
(0
N
h.
O)
O)
O
Q
o
GO
y—
T~
GO
s.
CM
in
N
9?S
§ « 9
V O S
88S
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-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log K„
Sorption
Log K„.
Chemical Hydrolysis
K K K
MY r1 MY
Comment
References
k^ik^ik
32. Carbon disulfide
75-15-0
1.84
2.16
0
0
3.15E4
1 1/61
Carbonyt sulfide
Carbon dioxide
Hydrogen sulfide
(Flammable gas: bp- -60°C;
(PK.-7.0)
463-58-1
124-38-9
7783-06-4
0.4
NA
NA
0.7
NA
NA
NO
0
0
6.3E2
0
0
4.1 E8
0
0
NHFG
NHFG
/ 29/ 40
/ 0/ 0
/ 0/ 0
33. Carbon tetrachloride
56-23-5
2.41
2.73
0
1.7E-2
0
RATE
/ 37/13
Carbon dioxide
Hydrochloric acid
124-38-9
7647-01-0
NA
NA
NA
NA
0
0
0
0
0
0
NHFG
NHFG
/ 0/ 0
/ 0/ 0
34. Chlordane
57-74-9
5.89
6.21
0
0
37.7
y
/ 62/ 3
2,4,5,6,7,8,8-Heptachloro-
3a,4,7,7a-tetrahydro-4,7-
methano-1 H-indene
5103-65-1
6.2
6.5
0
0
0
NLFG
/ 29/ 2
35. p-Chloroaniline
(pKb-10)
106-47-8
1.61
1.93
0
0
0
NLFG
/ 4/ 0
36. Chlorobenzene
108-90-7
2.578
2.898
0
0
0
NLFG
1 71 1
37. Chlorobenzilate
(PK.-13.6)
510-15-6
4.04
4.36
0
0
2.8E6
ff
/ 4/
S/s(p^hlorophenyl)hydroxy-
acetic acid (pK,-3.1)
p.p'-Dichlorobenzophenone
Ethanol
23851-46-9
90-98-2
64-17-5
2.5
4.43
-0.62
4.5
4.75
-0.30
0
0
0
0
0
0
2.8E5
0
0
ff
NLFG
NHFG
1 291 0
1 4/ 0
1 29/ 0
36. 2-Chloro-1,3-butadiene
(Chloroprene)
126-99-8
1.74
2.06
0
0
0
NLFG
1 4/ 0
-------
ro
Common Name
Chemical
Abstract
Service
No.
Sorption
Log K.
Sorption
Log K„.
Chemical Hydrolysis
K kn *b
M-'V' yi M'Y'
Comment
References
Koc/K^/k,
39. Chlorodibromomethane
124-48-1
1.91
2.23
NG
NG
2.5E4
t
/ 4/41
Carton monoxide
Hydrobromic acid
Hydrochloric acid
630-08-0
10035-10-6
7647-01-0
NA
NA
NA
NA
NA
NA
0
0
0
0
0
0
0
0
0
NHFG
NHFG
NHFG
/ 0/ 0
/ 0/ 0
/ 0/ 0
40. Chloroform
67-66-3
1.58
1.90
0
1.0E-4
2.74E3
/ 37/13
Carbon monoxide
Hydrochloric acid
630-08-0
7647-01-0
NA
NA
NA
NA
0
0
0
0
0
0
NHFG
NHFG
1 01 o
/ 01 0
41. Chloromethane
(Methyl Chloride: bp- -23.7°C)
74-87-3
42. 2-Chlorophenol
(PK.-8.4)
95-57-8
1.82
2.20
0
0
0
NLFG
/ 41 0
43. 3-Chloropropene
107-05-1
1.13
1.45
0
40
0
/ 4/ 5
3-Hydroxypropene
Hydrochloric acid
107-18-6
7647-01-0
-0.57
NA
-0.250
NA
0
0
0
0
0
0
NHFG
NHFG
/ 4/ 0
/ 01 o
44. Chromium (and compounds N.O.S.)
7440-47-3
45. Chrysene
218-01-9
5.34
5.66
0
0
0
NHFG
1 4/ 0
46. Cre8ols (See below)
47. o-Cresol
(PK.-9.8)
95-48-7
1.76
2.12
0
0
0
NHFG
/ 4/ 1
48. m-Cresol
(PK.-10.0)
108-39-4
1.76
2.12
0
0
0
NHFG
/ 4/ 1
49. p-Cresol
(PK.-10.1)
106-44-5
1.76
2.12
0
0
0
NHFG
/ 4/ 1
50. Cumene
98-82-8
3.40
3.72
0
0
0
NHFG
/ 4/ 0
J
&
§
5T
3
5?
I
to
I
5
£
(n
§-
I
to
o*
3
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
LogK^
Log K_
M'r'
V1
M-'Y'
Comment
Koc/K^/k,
51. Cyanide (amenable)
57-12-5
0
29
0
e
/ / 27
Carbon dioxide
124-38-9
NA
NA
0
0
0
NHFG
1 01 0
Ammonia
7664-41-7
NA
NA
0
0
0
NHFG
1 01 o
52. 2,4-Dichlorophenoxyacetic acid
94-75-7
0.68
2.68
0
0
0
NLFG
/ 4/ 1
(2,4-D: PK.-3.1)
53. DDD
72-54-8
5.89
6.21
0
2.5E-2
2.2E4
RATE
/ 4/ 24
2,2-S/'s(4-chlorophenyl)-1 -
1022-22-6
6.47
6.79
0
0
0
NLFG
1 29/ 0
chloroethene
(DDMU)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 o
54. DDE
72-55-9
6.64
6.956
0
0
0
NLFG
/ 7/ 12
55. p,p'-DDT
50-29-3
6.59
6.91
0
6.0E-2
3.1 E5
/ 4/ 12
DDE **
72-55-9
6.64
6.956
0
0
0
NLFG
/ 71 12
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 01 0
56. Diallate
2303-16-4
4.17
4.49
0
0.10
8E3
/ 62/ 3
Diallate (Z-)
17708-57-5
3.8
4.1
0
3.2E-1
0
RATE
/ 29/24
Diallate (£-)
17708-58-6
3.8
4.1
0
7.8E-2
7.3E3
RATE
/ 29/24
Diisopropylamine
108-18-9
0.84
1.16
0
0
0
NHFG
/ 4/ 0
(pK.,-11.5)
frans-2,3-Dichloro-2-propene-l -
16714-72-0
2.4
2.84
0
0
0
NLFG
1 29/ 0
thiol
(PK.-8.2)
c/s-2,3-Dichloro-2-propene-1 -
16714-71-9
2.5
3.0
0
0
0
NLFG
1 29/ 0
thiol
(PK.-8.2)
Carbon dioxide
124-38-9
NA
NA
0
0
0
NHFG
/ 01 o
57. DibenzJa,/)]anthraoene
53-70-3
6.52
6.84
0
0
0
NHFG
/ 4/ 0
-------
Fate Constants for Hazardous Waste Identification
S sf
R
ttl u
= J
/ 4/ 31
1 01 o
/ 4/ 0
1 01 o
/ 4/ 5
1 29/ 0
1 29/ 5
/ 29/ 0
/ 0/ 0
/ 29/ 0
/ 0/ 0
/ 29/ 0
/ 0/ 0
/ 29/41
/ 4/ 0
/ 29/ 5
/ 29/ 0
/ 0/ 0
/ 29/ 0
/ 0/ 0
/ 29/31
/ 0/ 0
/ 4/ 31
/ 29/ 0
/ 0/ 0
/ 0/ 0
I . .. _ .
/ 4/ 0
/ 37/ 1
Comment
RATE
NHFQ
CC
NHFQ
f
NHFG
NHFQ
NHFG
NHFG
cc
NHFG
cc
NHFG
NHFG
NHFG
NHFG
NHFG
NLFG
NHFG
NHFG
NLFG.w
NLFG
Chemical Hydrolysis
K K
MY V1 M'Y"'
m io in mm
LU LLI LU LLI LU
Csl O^OOQO ° ooo o^oo^ o ooo ooooooo
ir> mm
o
o
4.0E-3
0
1.4
0
30.9
0.46
8.9
0
0
0
0
1.4
0
1.6E1
1.4
8.9
0
0
0
0
29
0
1.8
0
0
0
o
o
O oooifjo ft! OOO O O O oJ O ftl ooo ooooooo
oi n r- k
o
o
S «
£ *
f 9
m ->
2.26
NA
0.49
NA
-0.210
-0.5
-1.4
-1.9
NA
-1.9
NA
1.42
NA
0.5
-0.857
-1.4
-1.9
NA
-1.9
NA
2.71
NA
2.07
1.72
NA
NA
1.53
I
3.40
b
1.94
NA
0.17
NA
-0.53
-0.8
-1.7
-2.2
NA
-23.
NA
1.10
NA
0.2
-1.2
-1.7
-2.2
NA
-2.2
NA
2.39
NA
1.75
1.40
NA
NA
1.21
00
o
CO
Chemical
Abstract
Service
No.
96-12-8
10035-10-6
73727-39-6
10035-10-6
106-89-8
96-24-2
556-52-5
56-81-5
7647-01-0
56-81-5
7647-01-0
96-13-9
10035-10-6
3132-64-7
4704-77-2
556-52-5
56-81-5
10035-10-6
56-81-5
7647-01-0
513-31-5
10035-10-6
16400-63-8
598-19-6
10035-10-6
7647-01-0
74-95-3
95-50-1
Common Name
58.1,2-Dibromo-3-ctiloropropane
(K.)
Hydrobromic acid
2-Bromo-3-chloropropanol
Hydrobromic acid
Epichlorohydrin
1 -Chloro-2,3-dihydroxy-
propane
1 -Hydroxy-2,3-
propylene oxide
Glycerol
Hydrochloric acid
Glycerol
(U
Hydrochloric acid
2,3-0ibromo-1 -propanol
Hydrobromic acid
Epibromohydrin
1-Bromo-2,3-
dihydroxypropane
1 -Hydroxy-2,3-
propylene oxide
Glycerol
Hydrobromic acid
Glycerol
(kj
Hydrochloric acid
2,3-Dibromopropene
Hydrobromic acid
2-Bromo-3-chloropropene
2-Bromo-3-hydroxypropene
Hydrobromic acid
Hydrochloric acid
59. Dibromomethane (methylene bromide)
60.1,2-Dichlorobenzene
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
LogK^
Log K„.
M'V
V1
M'V
Comment
Kcc/K^/k,
61.1,4-Dichlorobenzene
106-46-7
3.05
3.37
0
0
0
NLFG
/ 37/ 1
62. 3,3'-Dichlorobenzidine
91-94-1
3.32
3.64
0
0
0
NLFQ
/ 4/ 0
(pKb-11.7)
63. Dichlorodifluoromethane
75-71-8
(Freon 12: bp - -29°C)
64.1,1-Dichloroethane
75-34-3
1.46
1.78
0
1.13E-2
3.78E-1
RATE
/ 4/ 13
Acetaldehyde
75-07-0
-0.544
-0.224
0
0
0
NHFG
/ 4/ 0
(bp - 20 °C)
Vinyl chloride
75-01-4
1.04
1.36
0
0
0
NLFG
/ 1/ o
(bp - -13.37°C)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
65.1,2-Dichloroethane
107-06-2
1.13
1.45
0
9.61 E-3
54.7
/ 37/ 13
Vinyl chloride
75-01-4
1.04
1.36
0
0
0
NLFG
/ 1/ 0
(bp - -13.37°C)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
2-Chloroethanol
107-07-3
-0.492
-0.172
0
3.9E-2
3.2E5
/ 4/ 3
Ethylene oxide
75-21-8
-1.1
-0.792
2.9E5
21
0
/ 4/ 5
Ethylene glycol
107-21-1
-1.52
-1.2
0
0
0
NHFG
/ 29/ 2
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 0
66.1,1-Dichloroethytene
75-35-4
1.79
2.11
0
0
0
NLFG
/ 1/ 2
(Vinylidene chloride: bp - 30-32°C)
67. c/s-1,2-Dichloroethylene
156-59-2
1.7
2.0
0
0
0
NLFG
1 291 0
68.
-------
Fate Constants for Hazardous Waste Identification
P
o
o
o o o o in o
14/ /
/ 29/ 0
1 29/ 0
1 01 0
/ 29/ 0
1 291 Q
1 01 0
0 I6Z 1
0 IGZ 1
9 ll 1
Comment
NLFG
RATE
NLFG
NHFG
f
NHFG
NLFG
8
NLFG
NHFG
8
NLFG
NHFG
RATE
NLFG
NLFG
»
«5
>>
e
76
o
§
£
o
V
o
4.2
0
0
1.8E5
0
3E3
0
o o o o o o
o o o
o
4.6E-2
0
0
0.46
0
17
0
5 o o § o o
6.3E-2
0
0
o
<0
O O O O O 0) o
o o o o o o
o o o
S I
^1
85
3.07
1.99
2.0
NA
0.90
NA
-0.27
-1.06
2.2
0.55
NA
22.
0.50
NA
5.401
3.5
3.5
Sorption
Log K„
2.49
1.67
1.7
NA
0.58
NA
-0.59
-1.38
1.43
1.8
0.23
NA
1.8
0.18
NA
5.08
3.2
3.2
Chemical
Abstract
Service
No.
120-83-2
78-87-5
590-21-6
7647-01-0
19210-21-0
7647-01-0
75-56-9
57-55-6
542-75-6
10061-01-5
4643-05-4
7647-01-0
10061-02-6
4643-06-5
7647-01-0
60-57-1
64839-05-0
57345-89-8
Common Name
70. 2,4-Dichlorophenol
(PK.-7.9)
71.1,2-Dichloropropane
1 -Chloro-1 -propene
Hydrochloric acid
2-Chloropropan-1-ol
Hydrochloric acid
Propylene oxide
1,2-Dihydroxypropane
72.1,3-Dichloropropene
(mixture of isomers)
cis-1,3-Dichloropropene
cfS-3-Chloro-2-propen-l -ol
Hydrochloric acid
tran9-1,3-Dichloropropene
f/ans-3-Chloro-2-propen-1 -ol
Hydrochloric acid
73. Dieldrin
cis-1,2,3,4,10,10-Hexachloro-
6,7-dihydroxyexo-1,4,4a,5,6,7,
8,8a-octahydroexo-1,4-endo-5,8-
dimethanonaphthalene
(Dieldrin diol)
trans-1,2,3,4,10,10-Hexachloro-
6,7-dihydroxyexo-1,4,4a, 5,6,7,
8,8a-octahydroexo-1,4-endo-5,8-
dimethanonaphthalene
(Dieldrin diol)
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log K„.
Chemical Hydrolysis
k. K K,
MY V' M'Y'
Comment
References
Koc/K^/k,.
74. Diethyl phthalate
84-66-2
1.99
2.57
0
0
3.1 E5
RATE
11/ 4/ 9
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 291 0
Ethyl hydrogen phthalate
2306-33-4
2.18
2.50
0
0
1.6E5
C
1 29/ 0
o-Phthalic acid
88-99-3
-1.27
0.732
0
0
0
NHFG
1 4/ 0
(pK.-3.03)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 29/ 0
75. Dle1hyl8tilbe8trol
(PK.-9.3)
56-53-1
4.09
4.96
0
0
0
NHFG
1 4/ 0
-------
Fate Constants for Hazardous Waste Identification
8^
P
/ 4/ 32
/ 29/ 0
/ 4/ 0
1 291 0
1 4/ 0
/ 29/ 64
/ 0/ 0
/ 0/ 0
/ 29/ 0
/ 29/ 0
/ 29/ 0
/ 29/ 0
/ 4/ 0
/ 29/ 64
/ 4/ 0
/ 0/ 0
/ 4/ 0
/ 29/ 0
/ 4/ 0
1 29/ 0
1 4/ 0
/ 29/64
/ 0/ 0
/ 0/ 0
/ 29/ 0
Comment
RATE
z
NHFG
z
NHFG
bb
NHFG
NHFG
NLFG
NLFG
z
NHFG
bb
NHFG
NHFG
NHFG
z
NHFG
z
NHFG
bb
NHFG
NHFG
NLFG
«
•a
>.
8
* -L
7S
S
i
¦C
o
>-
<0
LD
o oo ooooo o oo ooooo o oo oo ooo
S 2: o T- OOOOO 2; O O CO O O O O T- oco ooo
^ O O O
O O OO OOOOO o oo ooooo o oo oo ooo
S i
B *
f &
0) ->
0.452
-0.5
-0.764
1.3
-0.764
-1.6
NA
NA
-0.5
1.5
-0.5
1.3
-0.764
-1.6
NA
NA
-0.764
-1
-0.764
-2.0
-0.764
-3.0
NA
NA
-1.0
Sorption
LogK,,.
0.132
-2.5
-1.08
-0.7
-1.08
-3.6
NA
NA
-0.8
-0.5
-0.8
-0.7
-1.08
-3.6
NA
NA
-1.08
-3
-1.08
-4
-1.08
-5
NA
NA
-0.8
Chemical
Abstract
Service
No.
60-51-5
756-80-9
67-56-1
106191-34-8
67-56-1
15834-33-0
7664-38-2
7783-06-4
5415-94-1
2700-77-8
5415-94-1
106191-34-8
67-56-1
15834-33-0
7664-38-2
7783-06-4
67-56-1
1112-38-5
67-56-1
1111-99-5
67-56-1
13598-51-1
7664-38-2
7783-06-4
20938-74-3
Common Name
76. Dimethoate
(K, at C)
O.O-Dimethylphosphorodithioic acid
(PK.-1.6)
Methanol **
O-Methylphosphorodithioic acid
(PK.-1.5)
Methanol **
Pho8phorodithioic acid (pK„-1.7)
Phosphoric acid
Hydrogen sulfide
/V-Methyl-2-hydroxyacetamide
(K, at P)
OMethyl-S-[2-(/V-methylacetamide)]-
phosphorodithioic acid (pK,-1.6)
N-Methyl-2-hydroxyacetamide
O-Methylphosphorodithioic acid
(PK.-1.5)
Methanol **
Phosphorodithlolc acid
Phosphoric acid
Hydrogen sulfide
Methanol **
(kj
O.O-Dimethylphosphorothioic acid
(PK.-1.6)
Methanol **
0-Methylpho8phorothioic acid
(PK.-1.5)
Methanol **
Phosphorothioic acid
(PK.-1.5)
Phosphoric acid
Hydrogen sulfide
W-Methyl-2-mercaptoacetarrtde (pK.-8.7)
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log K„.
Chemical Hydrolysis
K K K,
M'r1 r1 mV1
Comment
References
KclK^IK
77. 3,3'-Dimethoxybenzidine
(pKb-10.3)
119-90-4
1.49
1.81
0
0
0
NHFG
1 4/ 0
78. 7,12-Dimethylbenz{a|anthracene
57-97-6
6.64
6.96
0
0
0
NHFG
/ 41 0
79. 3,3'-Dimethylbenzidine
(PK.-9.3)
119-93-7
2.55
2.87
0
0
0
NHFG
/ 4/ 0
80. 2,4-Dimethylphenol
(PK.-10.1)
105-67-9
2.29
2.77
0
0
0
NHFG
/ 4/ 0
81. Dimethyl phthalate
131-11-3
1.20
1.52
0
0
1.8E6
RATE
/ 4/ 9
Methanol **
Methyl hydrogen phthalate
Methanol **
o-Phthalic acid (pk.-3.03)
67-56-1
4367-18-5
67-56-1
88-99-3
-1.08
1.6
-1.08
-1.27
-0.764
1.9
-0.764
0.732
0
0
0
0
0
0
0
0
0
9E5
0
0
NHFG
c
NHFG
NHFG
/ 4/ 0
/ 29/ 0
/ 4/ 0
/ 4/ 0
82.1,3-Dinttrobenzene
99-65-0
1.31
1.63
0
0
0
NHFG
/ 4/ 0
83. 2,4-Dinitrophenol
(PK.-3.3)
51-28-5
•0.09
1.91
0
0
0
NHFG
/ 4/ 0
84. 2,4-Dinitrotoluene
121-14-2
1.68
2.00
0
0
0
NHFG
/ 4/ 1
85. 2,6-Dfrrttrotoiuene
606-20-2
1.40
1.72
0
0
0
NHFG
/ 4/ 0
86. Di-n-butyl phthalate
84-74-2
4.37
4.69
0
0
1.2E5
RATE
/ 4/ 9
n-Butanol **
n-Butyl hydrogen phthalate
n-Butanol **
o-Phthalic acid
(pK.- 3.03)
71-36-3
131-70-4
71-36-3
88-99-3
0.503
3.43
0.503
-1.27
0.832
3.75
0.823
0.732
0
0
0
0
0
0
0
0
0
6E4
0
0
NHFG
c
NHFG
NHFG
/ 4/ 0
/ 29/ 0
/ 4/ 0
/ 4/ 0
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
LogK^
Sorption
Log K_
Chemical Hydrolysis
K
mrV V m'y'
Comment
References
87. Di-n-octyl phthalate
117-84-0
7.6
7.9
0
0
5.2E5
RATE
1 29/15
n-Octanol
n-Octyl hydrogen phthalate
n-Octanol
o-Phthalic acid
(pK.- 3.03)
111-87-5
5393-19-1
111-87-5
88-99-3
2.77
5.8
2.77
-1.27
3.09
6.1
3.09
0.732
0
0
0
0
0
0
0
0
0
2.6E5
0
0
NHFG
C
NHFQ
NHFG
1 291 0
1 29/ 0
/ 29/ 0
/ 4/ 0
88. 1,4-Dloxane
123-91-1
-0.812
-0.492
0
0
0
NHFG
/ 4/ 0
89. 2378 TCDDioxin
1746-01-6
6.10
6.42
0
0
0
NLFG
/ 16/ 0
90. 2378 PeCDOiOXins
6.9
7.2
0
0
0
NLFG
1 29/ 0
91. 2378 HxCDDiOxins
7.3
7.6
0
0
0
NLFG
1 29/ 0
92. 2378 HpCDDiOxins
7.8
8.1
0
0
0
NLFG
/ 29/ 0
93. OCDD
(Octachlorodibenzo-/>dioxin)
3268-87-9
8.08
8.4
0
0
0
NLFG
/ 29/ 0
94. Diphenylamine
(pK.,-13.4)
122-39-4
3.30
3.62
0
0
0
NHFG
/ 4/ 0
95. 1,2-Diphenythydrazine
(pK,,-13.2)
122-66-7
1.4
1.7
0
0
0
NHFG
/ 4/ 0
Oi
ro
21
8
5
3"
a
(o
I
to
I
§
0)
c/>
&
&)
o'
3
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log K„
Sorption
LogK,.
Chemical Hydrolysis
k. K. K,
MY r1 M"1Y''
Comment
References
Koc/K^/k*
96. Di8ulfoton
298-04-4
2.94
3.26
0
2.3
5.4E4
RATE
/ 4/ 6
(K, at Q
O.O-Diethylphosphofodithioic
298-06-6
-2.2
-0.2
0
0.2
0
z
/ 29/ 0
acid (pK,-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 291 0
O-Ethylphosphorodithioic
NG
-1
1.0
0
1
0
z
1 29/ 0
acid (pK,-1.6)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
Phosphorodithioic acid
15834-33-0
-3.6
-1.6
0
3
0
bb
/ 29/64
(PK.-1.7)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 0/ 0
2-Hydroxyettiylethylthioether
110-77-0
0.8
1.1
0
0
0
NLFG
/ 29/ 0
(K, at P)
Ethanol
64-17-5
•0.62
-0.30
0
0
0
NHFG
/ 29/ 0
0-Ethyl-S42-
-------
Fate Constants for Hazardous Waste Identification
References
/ 4/ 0
/ 4/ 0
Comment
RATE
RATE
NHFG
NLFQ
NLFG
NLFQ
f
NHFQ
NHFG
NHFG
NHFG
NHFG
NHFG
NHFG
I
NHFG
I*
(0
05
>>
8
* t
1 jA
(S
0
1
£
O
V
*""2
1.7E8
3.0E8
0
0
O O O
0
1.8E5
0
0
0
0
O
3.4E6
0
0
O
O
6.1 E-2
8.9E-2
0
0
5.5E-2
0
0
30.9
0.46
8.9
0
0
0
O
4.8E-3
0
0
O
O
O O O O
O O O
2.5E4
0
7.7E4
0
0
0
O
3.5E3
0
0
O
O
8 *
**
as
CO CO ^ CO
z csi
4.92
3.5
3.5
-0.210
-0.5
-1.4
-1.9
NA
-1.9
-0.217
0.671
-0.234
-0.30
3.32
g
CO
0
g j
**
a *
00 <10
Z CNJ
4.60
3.2
3.2
-0.53
-0.8
-1.7
-2.2
NA
-2.2
-0.54
0.351
-2.23
-0.62
ooe
0.55
Chemical
Abstract
Service
No.
115-29-7
959-98-8
33213-65-9
7664-93-9
2157-19-9
72-20-8
34015-58-2
14737-72-5
106-89-8
96-24-2
556-52-5
56-81-5
7647-01-0
56-81-5
110-80-5
141-78-6
64-19-7
64-17-5
100-41-4
60-29-7
Common Name
97. End08ulfan(Endosulfan I and II,
mixture)
Endosulfan I (alpha)
Endosulfan II (beta)
Sulfuric acid
1,4,5,6,7,7-Hexachloro-bicyclo-
[2.2.1 ]hept-5-ene-2,3-dimethanol
(Endosulfan diol)
"5
5'
^ LLJ
UJ 0
1
c
UJ
00
0>
99. Epichlorohydrin
1 -Chloro-2,3-dihydroxypropane
1 -Hydroxy-2,3-propylene
oxide
Glycerol
Hydrochloric acid
Glycerol
100. 2-Ethoxyethanol
(PK.-15.1)
101. Ethyl acetate
Acetic acid
(pK.-4.65)
Ethanol
102. Ethylbenzene
103. Ethyl ether
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
References
Common Name
No.
Log
Log K„,
MV
r'
M'V'
Comment
Koc/K~/*h
104. Ethyl methacrylate
97-63-2
1.27
1.59
0
0
1.1 E6
g
/ 4/ 0
Methacrylic acid
79-41-4
-1.53
0.470
0
0
0
NHFG
/ 4/ 0
(pK.-4.45)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 29/ 0
105. Ethyl methane8ulfonate
62-50-0
-0.27
0.051
0
1.25E3
0
RATE
1 4/60
Methylsulfonic acid
75-75-2
-2
0
0
0
0
NLFG
/ 29/ 0
(pK. - -0.39)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 291 0
106. Ethylene dibromide
106-93-4
1.42
1.74
0
6.3E-1
0
RATE
1 4/ 3
(1,2-Dibromoethane)
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
/ 0/ 0
Vinyl bromide
593-60-2
1.23
1.55
0
0
0
NLFG
/ 4/ 0
(bp-l6°C)
2-Bromoethanol
540-51-2
-0.35
-3.2E-2
0
0.1
1E6
r
/ 4/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
/ 0/ 0
Ethylene oxide
75-21-8
-1.1
-0.792
2.9E5
21
0
/ 4/ 5
Ethylene glycol
107-21-1
-1.5
-13.
0
0
0
NLFG
/ 29/ 0
-------
Fate Constants for Hazardous Waste Identification
References
K-/K-/H,
/ 4/ 6
/ 4/ 0
1 29/ 0
1 4/ 0
/ 29/ 0
/ 29/ 64
/ 0/ 0
/ 0/ 0
1 291 0
1 29/ 0
/ 29/ 0
/ 4/ 0
/ 29/ 0
/ 4/ 0
/ 29/64
/ 0/ 0
/ 0/ 0
o
O
/ 29/ 0
1
1
Comment
RATE
NHFG
z
NHFQ
z
bb
NHFG
NHFG
NLFG
NLFG
z
NHFG
z
NHFG
bb
NHFG
NHFG
NHFG
NHFG
NHFG
CO
o5
>»
2
1 *
2
o
V
io o o o o oooo oooooooo
o
o
o
cvi C\l CM
O Or- COOOO O^jOr-OCOOO
o
o
o
o oo o o OOOO oooooooo
o
o
o
Sorption
Log K„
2.27
-0.764
4.0
-0.764
2.5
-3.0
NA
NA
2.0
2.0
-1
-0.764
-2.0
-0.764
-3.0
NA
NA
4.95
4.23
-0.7
If
1.95
-1.08
2
-1.08
0.5
-5
NA
NA
1.6
1.6
-3
-1.08
-4
-1.08
-5
NA
NA
4.63
o>
CO
-2.7
Chemical
Abstract
Service
No.
52-85-7
67-56-1
15020-55-0
67-56-1
NG
13598-51-1
7664-38-2
7783-06-4
15020-57-2
15020-57-2
1112-38-5
67-56-1
1111-99-5
67-56-1
13598-51-1
7664-38-2
7783-06-4
206-44-0
86-73-7
64-18-6
Common Name
107. Famphur
(kn)
Methanol **
0-Methyl-0-p-(/V,/V-
dimethylsulfamoyl)-
phenylphosphorothioic acid
(PK.-1.5)
Methanol **
0-p-( W,/V-Dimethyl8ulfamoyl)-
phenylpho8phorothioic acid
(PK.-1.5)
Phosphorothioic acid
(PK.-1.5)
Phosphoric acid
Hydrogen sulfide
p-(N,W-Dimethyl-
8ulfamoyl)phenol
(PK.-8.4)
—(Ki.kb)
p-(/V,W-Dlmethyl8ulfamoyl)phenol
(PK.-8.4)
O.O-Dimethylphosphorothioic
acid (pK.-l.6)
Methanol **
O-Methylphosphorothioic
acid (pK.-1.5)
Methanol **
Phosphorothioic acid
(PK.-1.5)
Phosphoric acid
Hydrogen sulfide
108. Fluoranthene
©
c
£
o
3
LL
2
110. Formic acid
(PK.-3.8)
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log K„.
Chemical Hydrolysis
*. K K
M'r1 r1 m-'y'
Comment
References
Kc/K^/k,
111. Furan
110-00-9
1.00
1.32
0
0
0
NHFG
/ 4/ 0
112. 2378 TCDFuran
(2,3,7.8-Tetrachlorodlbenzofuran)
51207-31-9
6.62
6.94
0
0
0
NLFG
/ 4/ 0
113.12378 PeCDFuran
(1,2,3,7,8-Pentachlorodibenzofuran)
57117-41-6
6.5
6.8
0
0
0
NLFG
/ 29/ 0
114. 23478 PeCDFuran
(2,3,4,7,8-Pentachlorodibenzofuran)
57117-31-4
6.60
6.92
0
0
0
NLFG
/ 16/ 0
115. 2378 HxCDFuran8
7.0
7.3
0
0
0
NLFG
/ 29/ 0
116. 2378 HpCDFurans
7.6
7.9
0
0
0
NLFG
1 291 0
117. OCDF
(Octachlorodlbenzofuran)
39001-02-0
8.13
8.45
0
0
0
NLFG
1 29/ 0
118. Heptachlor
76-44-8
5.21
5.53
0
61
0
RATE
/ 62/25
1-Hydroxychlofdene
Hydrochloric acid
24009-05-0
7647-01-0
4.5
NA
4.8
NA
0
0
0
0
0
0
NLFG
NHFG
/ 29/ 2
1 01 o
119. Heptachlor epoxide
1024-57-3
4.9
52
0
6.3E-2
0
h
/ 29/0
noptacnTor oioi
Heptachlor triol
126959-40-8
126959-41-9
3.7
2.2
4.0
2.5
0
0
3.9E-3
0
3.2E4
0
h
NLFG
/ 29/ 0
/ 29/ 0
120. Hexachlorobenzene
118-74-1
5.411
5.731
0
0
0
NLFG
/ 7/ 1
121. Hexachlorobutadiene
87-68-3
4.46
4.78
0
0
0
NLFG
1 37/ 1
-------
Fate Constants for Hazardous Waste Identification
s *
u
O O CM <0(0 0
"t og Tj- Tf o
/ 4/ 0
E / 19/ 19
B II 0
/ / 0
|j \Z 11 1
/ 29/ 0
o
r-
o
GO
O
1
NHFQ
NLFG
NLFG
NHFQ
NLFG
j, RATE
unstabli
NLFG
NLFG
NHFG
NHFG
NHFG
k, NLF(
(0
o5
>»
e
i ^
*8
0
1
•C
O
1.74E6
0
6.5E5
0
0
0
o
o
o
o
o
o
o
o
1.05
0
0.26
0
0
0
o
00
CM
o
o
o
o
o
o
o o o o o o
o
O
o
o
o
o
o
o
*°X Sot
UORdJOS
3.75
NA
3.6
4.28
4.28
NA
3.75
5.04
CO
O*
CO
7.3
8S°9
0.76
2.2
4.47
Is
3.43
NA
3.3
3.96
3.96
NA
3.43
CM
3.61
5.0
6.26
0.44
1.9
4.15
Chemical
Abstract
Service
No.
319-84-6
7647-01-0
319-94-8
87-61-6
120-82-1
7647-01-0
319-85-7
77-47-4
NG
67-72-1
70-30-4
193-39-5
78-83-1
78-59-1
143-50-0
CM
1
CD
z
o
o
122. alpha-HCH
Hydrochloric acid
1,3,4,5,6-pentachlorocyclo-
hexene
1.2.3-T richlorobenzene
1.2.4-T richlorobenzene
Hydrochloric acid
X
0
1
124. Hexachlorocyclopentadiene
1,1 -Dihydroxytetrachloro-
cyclopentadiene
Polymers
125. Hexachloroethane
126. Hexachlorophene
(PK.-6.1)
0>
c
t
Q.
CO
c\T
o*
c
©
"D
c
K
CM
r"
128. Isobutyl alcohol
(PK.-15.8)
129. Isophorone
130. Kepone
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
Log
Log
MV
r1
M'Y"1
Comment
KclK.IK
132. gamma- HCH
58-89-9
3.40
3.72
0
1.05
1.73E6
1 1/ 4
(Lindane)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 0
1,3,4,5,6-pentachlorocydo-
319-94-8
3.3
3.6
0
0.26
6.5E5
/ 29/ 2
hexene
1,2,3-T richlorobenzene
87-61-6
3.96
4.28
0
0
0
NLFG
/ 4/ 6
1,2,4-Trichlorobenzene
120-82-1
3.96
4.28
0
0
0
NLFQ
/ 4/ 6
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFQ
/ 0/ 0
133. Mercury (and compounds N.O.S.)
7439-97-6
134. Methacrylonrtrile
126-98-7
0.22
0.540
5E2
0
5.2E3
I
/ 4/ 0
Methacryl amide
79-39-0
0.7
1.0
31.5
1.8E-2
0
I
/ 29/ 0
Methacryiic acid
79-41-4
-1.53
0.470
0
0
0
NHFQ
/ 4/ 0
(pK.-4.45)
Ammonia
7664-41-7
NA
NA
0
0
0
NHFG
1 01 o
135. Methanol
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
136. Methoxyctilor
72-43-5
4.90
5.08
0
0.69
1.2E4
38 / 38/ 12
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 01 0
2,2-8/s(p-methoxyphenyl)-
2132-70-9
4.1
4.4
0
0
0
NLFG
/ 9/ 0
1,1-dichloroethytene
Anisoin
119-52-8
3.9
4.2
0
6E3
0
m
/ 9/ 0
Anisil
1226-42-2
3.38
3.70
0
0
0
NHFG
1 4/ 0
137.3-Methylcholanthrene
56-49-5
7.0
7.3
0
0
0
NHFG
1 291 0
138. Methyl ethyi ketone
78-93-3
-0.03
0.29
0
0
0
NHFG
1 65/ 1
139. Methyl isobutyl ketone
108-10-1
0.87
1.19
0
0
0
NHFG
/ 4/ 0
-------
4k
O
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
LogK^
Log
M-'r1
r1
MV1
Comment
Ko/K^/k,,
140. Methyl methacrylate
80-62-6
0.74
1.06
0
0
1.9E6
RATE
/ 4/ 24
Methacrylic acid
79-41-4
-1.53
0.470
0
0
0
NHFG
/ 4/ 0
(pK.-4.45)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
141. Methyl parathlon
298-00-0
2.47
2.79
NG
2.8
NG
n
/ 4/ 39
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
O-Methyl-O-(p-nrtrophenyl)-
7699-30-1
-2.5
-0.5
0
0.2
0
z
/ 29/ 0
phosphorothioic acid (pK.-l.3)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
O(p-Nitrophenyl)pho8phoro-
18429-96-4
0
1
0
z
/ / o
thtoic acid (pK,-l.l)
Pho8phorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 01 o
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 0/ 0
p-Nitrophenol
100-02-7
1.2
1.85
0
0
0
NHFG
/ 4/ 0
(PK.-7.0)
p-Nitrophenol
100-02-7
1.2
1.85
0
0
0
NHFG
/ 41 0
(PK.-7.0)
O.O-Dimelhylphosphorothioic acid
1112-38-5
-3
-1
0
0.2
0
z
/ 29/ 0
(PK.-1.6)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
O-Methylphosphorothioic acid
1111-99-5
-4
-2.0
0
1
0
z
/ 29/ 0
(PK.-1.5)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/ 64
(PK.-1.5)
Phosphoric add
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 01 o
142. Naphthalene
91-20-3
3.11
3.36
0
0
0
NHFG
38/ 38/ 0
143. 2-Naphthylamine
91-59-8
1.77
2.09
0
0
0
NHFG
/ 4/ 0
(pKb"9.8)
144. Nickel {and compounds N.O.S.)
7440-02-0
2?
of
s>
3
5f
<7T
I
Q)
I
§
I
(/>
Q.
P
Si
o*
3
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log K„.
Chemical Hydrolysis
K K K
MY1 V1 M'Y"1
Comment
References
Koc/K^/k,
145. Nitrobenzene
98-95-3
1.51
1.83
0
0
0
NLFG
/ 37/ 1
146. 2-Nitropropane
79-46-9
0.23
0.554
0
0
0
NHFG
/ 4/ 0
147. W-Nitroeo-di-n-butylamine
(PK.<1)
924-16-3
2.09
2.41
0
0
0
NHFG
/ 29/ 0
148. /V-Nitroaodiethylamine
(PK.<1)
55-18-5
-0.03
0.290
0
0
0
NHFG
/ 29/ 0
149. N-Nitroaodimethylamine
(PK.<1)
62-75-9
0.448
0.768
0
0
0
NHFG
/ 29/ 0
150. W-Nitrosodiphenylamine
(pK.<0)
86-30-6
2.84
3.16
0
0
0
NHFG
1 291 0
151. W-Nttroso-di-n-prapylamine
(PK.<1)
621-64-7
1.03
1.35
0
0
0
NHFG
1 29/ 0
152. N-Nitroaomethylethylamine
(PK.<1)
10595-95-6
1.03
1.35
0
0
0
NHFG
1 29/ 0
153. W-Nttroaopiperidine
100-75-4
-0.02
0.305
0
0
0
NHFG
1 4/ 0
154. A/-Nitroaopyrrolidine
930-55-2
-0.57
•0.254
0
0
0
NHFG
/ 4/ 0
155. Octamethyi pyrophosphoramtde
S/s(W,A/-ethylamino)-
pho8phoric acid (pK.4.2)
152-16-9
27972-73-2
1.9E3
0
NG
0
NG
0
NLFG
1 1 34
/ / o
-------
N>
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
Log
Log
hY'
r1
MTV'
Comment
156. Parathion (ethyl)
56-38-2
3.15
3.47
0
2.4
3.7E6
1 4/ 21
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 291 0
O-Ethyl-O-(p-nitrophenyl)-
15576-30-4
0
0.2
0
z
1 1 0
pho8phorothioic acid (pK,-l.2)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFQ
/ 29/ 0
0-(p-Nitrophenyl)pho8phoro-
18429-96-4
0
1
0
z
/ / o
thioic acid (pK,-1.1)
p-Nitrophenol
100-02-7
1.2
1.85
0
0
0
NHFG
/ 4/ 0
(PK.-7.0)
Phopsphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/ 64
(PK.-1-5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 0/ 0
p-NHrophenol
100-02-7
1.2
1.85
0
0
0
NHFG
/ 4/ 0
(PK.-7.0)
O.O-Diethylphosphorothioic acid
2465-65-8
-2
0
0
02
0
z
/ 29/ 0
(PK.-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 291 0
O-Ethylphosphorothioic acid
14018-63-4
-1.5
0.5
0
1
0
z
1 29/ 0
(PK.-15)
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/ 64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 0/ 0
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
157. Pentachlorobenzene
608-93-5
5.39
5.183
0
0
0
NLFG
/ 71 0
158. Pentachloronitrobenzene (PCNB)
82-68-8
4.57
4.89
0
0
0
NLFG
/ 4/ 0
159. Pentachlorophenol
87-86-5
3.06
5.06
0
0
0
NLFG
/ 4/ 1
(PK.-4.8)
160. Phenol
108-95-2
123
1.48
0
0
0
NHFG
/ 4/ 1
(PK.-10)
2?
(5"
&
in
5)
5?
§-
§
i
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log K„
Chemical Hydrolysis
K K
MY r1 M'Y1
Comment
References
K»/K~/kh
161. Phenylenediamine:
1,2-Phenylenediamine
95-54-5
-0.1
0.2
0
0
0
NHFG
/ 29/ 0
(pKb-9.3)
1,3-Phenylenediamine
108-45-2
-0.3
0.05
0
0
0
NHFG
/ 29/ 0
(pKb"8.7)
1,4-Phenylenediamine
106-50-3
NA
-0.4
0
0
0
NHFG
1 29/ 0
(pKb-7.7)
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
References
Common Name
No.
Log
Log
M'r1
r1
M"Y'
Comment
162. Phorate
298-02-2
2.64
2.96
0
62
0
RATE
/ 4/ 25
(k„ at P-O)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 29/ 0
0-Ethyl-S-[(ethylthio)methy11-
NG
-2.5
-0.5
0
0.2
0
z
1 29/ 0
phosphorodithioic acid
(PK.-1.6)
O-Ethylphosphorodithioic
NG
-1
1.0
0
1
0
z
1 291 0
acid (PK.-1.6)
Ptio8phorodtthioic acid
15834-33-0
-3.6
-1.6
0
3
0
bb
1 29/ 64
(PK.-1.7)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 01 o
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 29/ 0
Hydroxymethylethylthio-
15909-30-5
0.2
0.5
0
0
0
NLFG
/ 29/ 0
ether
(ig
Mencaptomethylethylthioether
29414-49-1
2.0
2.3
0
0
0
NLFG
/ 29/ 0
O.ODiethylpho8phorothioic acid
2465-65-8
-2
0
0
0.2
0
z
/ 29/ 0
(PK.-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
O-Ethylphosphorothioic acid
14018-63-4
-1.5
0.5
0
1
0
z
/ 29/ 0
(PK.-1.5)
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/ 64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 0/ 0
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
(K, at S-C)
Hydroxymethylethylthioether
15909-30-5
0.2
0.5
0
0
0
NLFG
/ 29/ 0
O.O-Diethylphosphorodithioic
298-06-6
-2.2
-0.2
0
0.2
0
z
/ 29/ 0
acid (pK,-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
O-Ethylphosphorodithioic acid
NG
-1
1.0
0
1
0
z
/ 29/ 0
(PK.-1.6)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
Phosphorodithioic acid
15834-33-0
-3.6
-1.6
0
3
0
bb
/ 29/64
(PK.-1.7)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 29/ 0
21
cS"
&
5?
5T
3
co
&
s
0)
(/>
&
Q)
O*
3
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log K„,
Chemical Hydrolysis
K K K
wr'r1 rx m'y'
Comment
References
Koc/Ko./**
163. Phthalic anhydride
85-44-9
-0.62
0
4.9E5
0
U, RATE
/ 35/22
oPhthalic acid
(pK.-3.03)
88-99-3
-1.27
0.732
0
0
0
NHFG
/ 4/ 0
164. Polychlorinated biphenyls
(Aroclors)
1336-36-3
0
0
0
NLFG
/ / o
165. Pronamide
23950-58-5
2.63
2.95
59
0
6.1 E2
RATE
/ 4/ 6
3,5-Dichlorobenzoic acid
(pK.-3.46)
1,1 -Dimethyl-2-propynylamine
(pKb-8.1)
51-36-5
2978-58-7
1.5
-0.63
3.5
-0.306
0
0
0
0
0
0
NLFG
NHFG
1 291 0
1 4/ 0
166. Pyrene
129-00-0
4.92
5.18
0
0
0
NHFG
/ 38/ 0
167. Pyridine
(P«b"8.7)
110-86-1
0.34
0.665
0
0
0
NHFG
/ 4/ 1
168. Safrole
94-59-7
2.34
2.66
0
0
0
NHFG
1 4/ 24
169. Selenium (and compounds N.O.S.)
7782*49-2
170. Stim (arttfooropotrnde N.O.S.)
7440-28-4
171. Strychnine and salts
(pKb-4.7)
57-24-9
NA
2.0 "
0
0
0
NLFG
1 291 0
172. Styrene
100-42-5
2.84
3.16
0
0
0
NHFG
1 37/ 0
173.1,2,4,5-Tetrachlorobenzene
95-94-3
4.284
4.604
0
0
0
NLFG
/ 7/ 0
-------
•fc.
O)
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
k.
kb
References
Common Name
No.
LogK„
Log K„.
M-V
Y1
M'Y"'
Comment
174.1,1,1,2-Telrachloroethane
630-20-6
2.71
3.03
0
1.37E-2
1.13E4
RATE
1 1/13
1,1,2-T rtchloroelhylene **
79-01-6
2.10
2.42
0
0
0
NLFG
/ 37/ 2
2,2,2-Trichloroethanol (pK.-3.7)
115-20-8
1.13
1.45
0
0.65
0
V
/ 29/ 0
Hydroxyacetic acid
79-14-1
-4
-2
0
0
0
NHFG
/ 29/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFQ
/ 0/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
175.1,1,2,2-Tetrachloroethane
79-34-5
2.07
2.39
0
5.10E-3
1.59E7
RATE
/ 37/13
1,1,2-T richloroethylene **
79-01-6
2.10
2.42
0
0
0
NLFG
/ 37/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
176. Tetrachloroethylene
127-18-4
2.21
2.53
0
0
0
NLFG
/ 37/ 0
177. 2,3,4,6-Tetrachlorophenol
58-90-2
2.32
4.32
0
0
0
NLFG
/ 4/ 1
(PK.-5.3)
178. Tetraethyl dithiopyrophosphate
3689-24-5
3.51
3.83
0
84
9E6
0
/ 62/ 36
(Sulfotep)
0,0-Diethylpho8phorothioic acid
2465-65-8
-2
0
0
0.2
0
z
/ 29/ 0
(PK.-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
OEthylphosphorothioic acid
14018-63-4
-1.5
0.5
0
1
0
z
1 291 0
(PK.-1.5)
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
1 29/64
(pK.-1.5J
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 01 o
Hydrogen sulfide
7783-06-04
NA
NA
0
0
0
NHFG
/ 01 0
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
179. Thallium (and compounds N.O.S.)
180. Toluene
108-88-3
2.43
2.75
0
0
0
NHFG
/ 29/ 1
181. 2,4-Toluenediamine
95-80-7
0.02
0.337
0
0
0
NHFG
/ 4/ 0
(pKt-9.0)
&
s
3"
a
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
K,
References
Common Name
No.
LogK,,
Log K„.
irY1
r'
M'Y'
Comment
182. 2,6-Toluenediamine
823-40-5
0.02
0.337
0
0
0
NHFG
/ 4/ 0
(pKh-8.9)
183. o-Toluidine
95-53-4
1.24
1.56
0
0
0
NHFG
/ 4/ 0
(pKt-9.3)
184. p-Toluidine
106-49-0
1.24
1.56
0
0
0
NHFG
/ 4/ 0
(pKt"8.9)
185. Toxaphene (chlorinated camphenes)
8001-35-2
4.31
4.63
0
7.0E-2
2.8E4
P
/ 62/24
186. Tribromomethane
75-25-2
2.05
2.37
NO
NG
1E4
t
/ 4/ 1
(Bronx) form)
Carbon monoxide
630-08-0
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
1 01 o
187.1,2,4-T richlorobenzene
120-82-1
3.96
4.28
0
0
0
NLFG
/ 4/ 2
188.1,1,1-Trichloroethane
71-55-6
2.16
2.47
0
6.4E-1
2.4E6
/ 37/67
1,1 -Dlchloroethytene **
75-35-4
1.79
2.11
0
0
0
NLFG
/ 1/ 2
(bp-31.9°C)
Acetic acid
64-19-7
-2.23
-0.234
0
0
0
NHFG
/ 4/ 2
(pK.-4.73)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 o
189.1,1,2-Trichloroethane
79-00-5
1.73
2.05
0
2.73E-5
4.95E4
RATE
1 4/ 13
1,1 -Dichloroethytene **
75-35-4
1.79
2.11
0
0
0
NLFG
/ 1/ 2
(bp-31.9°C)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 01 0
Chloroacetaldehyde
107-20-0
0.07
0.389
0
7E-3
2.6E4
/ 4/ 2
Hydroxyacetaldehyde
141-46-8
-1.38
-1.06
0
0
0
NHFG
/ 4/ 2
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
190. Trichloroethylene
79-01-6
2.10
2.42
0
0
0
NLFG
/ 37/ 2
(1,1,2-Trichloroethytene)
J
3.
-------
48 Fate Constants for Hazardous Waste Identification
8^
P
o
/ 4/ 0
<0 o co m o m oooo oooo
v*- n O) ^ O) O) ® n O) o n A n
^ CM CM CM CM CM CM
O
Comment
NLFG.ee
NLFG
NLFG
NLFG
NLFG
RATE
NHFG
f
NHFG
NHFG
NHFG
NHFG
NHFG
X
NLFG
NHFG
2
—1
z
CO
¦a
&
2
x j=>-
!
¦C
o
o
o
o
o
o
co in in
LLI ID UJ
(O o CO O GO ° OOOO OOOO
CO r- r—
o
o
o
o
o
o
1.7E-2
0
0.46
30.9
0.46
8.9
0
0
0
0
0
1.8
0
0
o
o
o
o
o
o
* *•
o o o l{{ o }ii oooo oooo
cvi h-
o
S 1
s *
f *
X -J
2.43
3.85
3.57
3.43
CO
1.98
NA
0.8
-0.210
-0.5
-1.4
-1.9
NA
-1.9
NA
NA
2.1
0.25
NA
3.29
1^
f
55 -J
2.11
2.93
2.25
1.43
1.74
1.66
NA
0.5
-0.53
-0.8
-1.7
-2.2
NA
-2.2
NA
NA
1.8
-0.1
NA
2.97
Chemical
Abstract
Service
No.
75-69-4
95-95-4
CNJ
(O
9
00
CO
93-76-5
93-72-1
96-18-4
7647-01-0
616-23-9
106-89-8
96-24-2
556-52-5
56-81-5
7647-01-0
56-81-5
7647-01-0
7647-01-0
78-88-6
5976-47-6
7647-01-0
76-13-1
Common Name
191. Trichlorofluoromethane
(Freon 11: bp-24.1°C)
192. 2,4,5-Trichlorophenol
(PK.-7.1)
193. 2,4,6-Trichlorophenol
(PK.-6.4)
194. 2,4,5-Trichlorophenoxyacetic acid
(PK.-3.0)
195. 2-(2,4,5-Trichlorophenoxy)propionic
acid (Silvex; (pK,-3.4)
196.1,2,3-Trichloropropane
Hydrochloric acid
2,3-Dichloro-1 -propanol
Epichlorohydrin
1 -Chloro-2,3-dihydroxy-
propane
1 -Hydroxy-2,3-
propylene oxide
Glycerol
Hydrochloric acid
Glycerol
Hydrochloric acid
Hydrochloric acid
2,3-Dichloropropene
2-Chloro-3-hydroxypropene
Hydrochloric acid
197.1,1,2-T richloro-1,2,2-trifluoro-
ethane
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
k.
K,
K
References
Common Name
No.
Log
Log K„.
MY'
Y-1
M'Y1
Comment
Koc/Ko./k,
198. sym-Trinitrobenzene
99-35-4
1.05
1.37
0
0
0
NHFG
/ 4/ 0
(1,3,5-Trinitrobenzene)
199. rns(2,3-dibromopropyl)pho8phate
126-72-7
3.19
3.51
0
8.8E-2
3.0E5
RATE
/ 4/ 24
(kn)
0,0-(2,3-Dibromopropy1)-
5412-25-9
0
0.2
0
z
/ / o
phosphoric acid (pK,-0.8)
0-(2,3-Dibromopropyl)-
5324-12-9
0
1
0
z
/ / o
pho8phoric acid (pK,-1.3)
2,3-Dibromo-l -propanol
96-13-9
1.10
1.42
0
1.4
5.4E5
cc
/ 29/ 0
Phosphoric add
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
2,3-Dibromo-1 -propanol
96-13-9
1.10
1.42
0
1.4
5.4E5
cc
1 291 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
1 01 o
Epibromohydrin
3132-64-7
0.2
0.5
1.9E4
1.6E1
0
/ 29/ 41
1-Bromo-2,3-
4704-77-2
-1.18
-0.857
0
1.4
5.4E5
CC
/ 4/ 0
dihydroxypropane
1-Hydroxy-2,3-
556-52-5
-1.7
-1.4
7.7E4
8.9
0
/ 29/ 5
propylene oxide
Glycerol
56-81-5
-2.2
-1.9
0
0
0
NHFG
1 291 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
1 01 o
Glycerol
56-81-5
-22.
-1.9
0
0
0
NHFG
/ 29/ 0
2,3-Dibromo-1 -propanol
96-13-9
1.10
1.42
0
1.4
5.4E5
cc
/ 29/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
/ 01 0
2-Bromo-1,3-propanediol
4704-87-4
-1.4
-1.1
0
2
9E5
q
1 291 0
Glycerol
56-81-5
-2.2
-1.9
0
0
0
NHFG
1 29/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
/ 01 o
(|g
0,0(2,3-Dibromopropyi)-
5412-25-9
0
0.2
0
z,dd
/ / o
phosphoric acid (p«,-0.8)
2,3-Dibromo-1 -propanol
96-13-9
1.10
1.42
0
1.4
5.4E5
cc
/ 29/ 0
2-Bromo-2-propen-1 -ol
598-19-6
0.43
0.75
0
0
0
NLFG
/ 29/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
/ 01 o
200. Vanadium
7440-62-2
201. Vinyl chloride
75-01-4
1.04
1.36
0
0
0
NLFG
1 1/ o
(Chloroethene: bp - -13.4°C)
J
3.
CO
-------
U1
o
Common Name
Chemical
Abstract
Service
No.
Sorption
Log Koc
Sorption
LogK,,.
Chemical Hydrolysis
k. K K
w'r' V m-'v1
Comment
References
202. Xylenes
1330-20-7
0
0
0
NHFG
1 1 o
(mixture of three isomers)
o-Xylene
95-47-6
3.02
3.34
0
0
0
NHFG
/ 29/ 0
m-Xylene
108-38-3
3.09
3.41
0
0
0
NHFG
/ 29/ 0
p-Xylene
106-42-3
3.12
3.44
0
0
0
NHFG
/ 29/ 0
203. Zinc (and compounds N.O.S.)
7440-66-6
2?
&
s
5?
5?
I
Qj
I
§
I
Q.
CD
55.
P*
a>
o'
a
COMMENT
RATE) Hydrolysis data were extrapolated with the RATE program to obtain rate constants at 25° C (see referenoe #28).
NG) A rate constant was not given in the publication or a CAS number was not assigned in the CAS Registry.
**) This product appears as a parent compound elsewhere in the alphabetically arranged table.
NA) When NA (not applicable) appears in one of the sorption columns, the compound is either an inorganic compound or an organic base that is ionized within the
environmental pH range with a pK, value greater than 6. A value cannot be computed.
Shaded rows contain inorganic compounds which are not addressed in this work.
a) At an alkaline pH and concentrations above 2 ppm for acrylamide, cloudiness was observed in the laboratory hydrolysis experiment. Cloudiness was thought to have been
polymerization.
b) The hydrolysis rate constant was assumed to be the same as the parent compound's by analogy to Ws(2-chloroethyl)ether and its product 2-(2- chloroethoxy)ethanol (see
text in Part II).
c) The hydrolysis rate constant was assumed to be half the parent's.
d) The hydrolysis rate constant was assumed to be the same as the one for di-n-butyl phthalate for both pathways.
e) Cyanide will not sorb onto sediments at a detectable rate.
f) The hydrolysis rate constants for 2-chloropropan-l-ol and 1-chioro-2t3-dihydroxypropane were assumed by analogy to be the same as those of 2,3-dichloro-1-propanol
(see #196).
-------
g) The hydrolysis rate constant was estimated by analogy to be 0.6 of methyl methacrylate's.
h) The hydrolysis rate constant for heptachlor epoxide was assumed by analogy to be the same as dieldrin's. The reaction to the final product heptachlor triol occurs through
the intermediate heptachlor diol, for which a rate estimate was assumed to be 1/10 the rate of 2-chloro-ethanol.
i) The hydrolysis rate constants were assumed by analogy to be the same as lindane's.
j) Hydrolysis of hexachlorocyclopentadiene results in the formation of 1,1-dihydroxytetrachlorocyclopentadiene which is an unstable product. Its degradation leads to the
formation of polymers which cannot be identified.
k) Kepone hydrates in an aqueous medium. The sorption coefficient of the hydrated form may be orders of magnitude lower than the coefficient of the unhydrated form. The
given log values are for the unhydrated form. A value for the hydrated form cannot be estimated.
I) The hydrolysis rate constants for methacrylonitrile and its product methacrylamide were assumed by analogy to be the same as those for acrylonitrile and its product
acryl amide.
m) The product of methoxychlor, anisoin, degrades to anisil by autooxidation with an estimated half-life of one hour.
n) The hydrolysis rate was determined at a pH<8.
o) The hydrolysis rate constants for tetraethyl dithiopyrophosphate were based by analogy on the rate constants of tetraethyl pyrophosphate and tetraethyl
monothiopyropho8phate. The rate constants of tetraethyl pyrophosphate were divided by 10 as an adjustment for the two sulfur substituents in tetraethyl
dithiopyrophosphate.
p) Toxaphene is produced by the chlorination of camphene and is a complex mixture of at least 177 C10 polychloro- derivatives. It has an approximate overall empirical
formula of C10H10CI8 (The Merck Index, Eleventh Edition). Products can, therefore, not be identified.
q) The hydrolysis rate constants for 2-bromo-1,3-propanediol were estimated by analogy to be five times those of 2,3-dichloropropanol'8 (see #196) because of the two
hydroxide groups and the greater reactivity of bromine.
r) The hydrolysis rate constants for 2-bromoethanol were estimated by analogy to be three times larger than those of 2-chloroethanol because of the greater reactivity of
bromine.
8) The hydrolysis rate constants for the c«9- and trans-'\ ,3-dichloropropene were assumed by analogy to be the same as 3-chloropropene'8 (#43).
t) The hydrolysis rate constants for bromodichloromethane, chlorodibromomethane, and tribromomethane were determined in 66.67% (v/v) dioxane/water.
u) Phthalic anhydride hydrolyzes to o-phthalic acid with a half-life of less than one minute. A value for the anhydride would be meaningless.
v) The hydrolysis rate constant for 2,2,2-trichloroethanol was assumed by analogy to be the same as 1,1,1-trichloroethane's (see #186).
w) QSAR model computations have indicated that the half-life of this halogenated methane is several thousand years. Its hydrolysis process was, therefore, designated as
NLFQ.
x) The hydrolysis rate constant for 2,3-dichloropropene was assumed by analogy to be the same as 2-bromo-3-chloropropene's (see #58).
cn
-------
y) The log value for technical grade chlordane was calculated by averaging the measured values of the cis- and trans- Isomers. The hydrolysis rate constant given is
for the c/9- isomer only. The trans- isomer will not hydrolyze.
z) The hydrolysis rate constant for the degradation of the organophosphorus diester to the monoester was estimated to be smaller than the parent's by a factor of ten, whereas
the rate constant for the degradation of the monoester to the acid was estimated to be half the rate of the parent's". These estimated rate constants were based on the
average of the neutral rate constants of five organophosphorus compounds.
aa) The hydrolysis rate constants for dichloromethane were extrapolated to 25°C from elevated temperatures.
bb) The hydrolysis rate constant was estimated by extrapolation. Because the value was estimated, no distinction was made of the fact that hydrolysis of the phosphorodithioic
acid is slightly faster than the monoacid.
cc) The hydrolysis rate constants for 2-bromo-3-chloropropanol, 2,3-dibromo-1 -propanoi, and 1 -bromo-2,3-dihydroxypropane were estimated by analogy to be three times larger
than those of 2,3-dichk>ro-1-propanoi (see #196) because of the greater reactivity of bromine.
dd) The alkaline hydrolysis pathway of the diester is identical to its neutral pathway.
ee) Half-lives of polyhalogenated methanes are usually larger than 50 years. The half-life of trichlorofluoromethane is estimated to be larger than 50 years. Its hydrolysis
prace88 is, therefore, designated as NLFG.
ff) The hydrolysis rate constants for aramite and chlorobenzilate were determined experimentally in ERL-Athens' laboratory. Products, except the hydrogen sulfites, were
confirmed by spectral analyses. The hydrolysis rate constants for the products were estimated.
gg) The hydrolysis rate constants were assumed to be the same as the parent's.
-------
Part I 53
TABLE 2. SAR computed reductive rate constants for selected halogenated aliphatics
and nitroaromatics.
Halogenated Aliphatics
Chemical
Abstract
Service No.
1%
Organic Carbon
k(year1)
0.02%
Organic Carton
k(year"1)
26. Bromodichloromethane
75-27-4
1.2E3
1.9E-1
27. Bromomettiane
74-83-9
1.4E2
2.2E-2
33. Carbon tetrachloride
56-23-5
5.8E1
9.3E-3
39. Chlorodibromomethane
124-48-1
1.2E3
1.8E-1
40. Chloroform
67-66-3
2.6E1
4.2E-3
58. 1,2-Dibromo-3-chloropropane
96-12-8
2.4E2
3.8E-2
59. Dibromomethane
74-95-3
4.0E2
6.4E-2
64. 1,1-Dichloroethane
75-34-3
1.1 El
1.7E-3
65. 1,2-Dichioroethane
107-06-2
4.0
6.5E-4
69. Dichloromethane
75-09-2
8.7
1.4E-3
71. 1,2-Dichloropropane
78-87-5
5.4
8.5E-4
72. 1,3-Dichloropropene
542-75-6
6.7
1.1 E-3
106. Ethylene dibromide
106-93-4
1.7E2
2.7E-2
125. Hexachloroethane
67-72-1
2.8E1
4.5E-3
174. 1,1,1,2-Tetrachloroethane
630-20-6
7.0
1.1 E-3
175. 1,1,2,2-Tetrachloroethane
79-34-5
7.5
1.2E-3
186. Tribromomethane
75-25-2
1.2E3
1.8E-1
188. 1,1,1-Trichloroethane
71-55-6
1.5E1
2.4E-3
189. 1,1,2-T richloroethane
79-00-5
5.4
8.5E-4
191. Trichlorofluoromethane
75-69-4
5.8E1
9.3E-3
196. 1,2,3-Trichloropropane
96-18-4
4.3
6.8E-4
197. 1,1,2-Trichloro-1,2,2-trifluoroethane
76-13-1
4.0E1
6.4E-3
Nitroaromatics
Chemical
Abstract
Service No.
1%
Organic Carbon
k(year'1)
0.02%
Organic Carbon
k(year'1)
30. Dinoseb
88-85-7
5.0E3
8.8E1
82. 1,3-Dinitrobenzene
99-65-0
8.0E2
1.4E2
83. 2,4-Dinitrophenol
51-28-5
2.2E3
3.9E2
84. 2,4-Dinitrotoluene
121-14-2
6.6E2
1.2E2
85. 2,6-Dinitrotoluene
606-20-2
8.0E2
1.4E2
141. Methyl parathion
298-00-0
1.2E2
2.2E1
145. Nitrobenzene
98-95-3
3.0E2
5.2E1
156. Parathion
56-38-2
1.2E2
2.2E1
198. sym-Trinitrobenzene
99-35-4
2.2E3
3.9E2
-------
Part I 55
REFERENCES
0. Kollig, H.P., J.J. Ellington, E.J. Weber, and N.L. Wolfe. Pathway Analysis of Chemical
Hydrolysis. U.S. Environmental Protection Agency, Athens, GA.
1. Ellington, J.J., C.T. Jafvert, H.P. Kollig, E.J. Weber, and N.L. Wolfe. 1991. Chemical-
Specific Parameters for Toxicity Characteristic Contaminants. U.S. Environmental
Protection Agency, Athens, GA, EPA/600/3-91/004.
2. Kollig, H.P., J.J. Ellington, E.J. Weber, and N.L. Wolfe. 1990. Pathway Analysis of
Chemical Hydrolysis for 14 RCRA Chemicals. U.S. Environmental Protection Agency,
Athens, GA, EPA/600/M-89/009.
3. Ellington, J.J., F.E. Stancil, W.D. Payne, and C.D. Trusty. 1988. Measurements of
Hydrolysis Rate Constants for Evaluation of Hazardous Waste Land Disposal. Volume
III. Data on 70 Chemicals. U.S. Environmental Protection Agency, Athens, GA,
EPA/600/3-88/028.
4. QSAR, a structure-activity based chemical modeling and information system. 1986.
Developed jointly by the U.S. Environmental Protection Agency, Environmental Research
Laboratory-Duluth, Montana State University Center for Data Systems and Analysis,
and the Pomona College Medicinal Chemistry Project.
5. Mabey, W. and T. Mill. 1978. Critical review of hydrolysis of organic compounds in water
under environmental conditions. J. Phys. Chem. Ref. Data. 7(2):383-415.
6. Ellington, J.J., F.E. Stancil, Jr., and W.D. Payne. 1986. Measurement of Hydrolysis Rate
Constants for Evaluation of Hazardous Waste Land Disposal. Volume I. U.S.
Environmental Protection Agency, Athens, GA, EPA/600/3-86/043.
7. De Bruijn, J., F. Busser, W. Seinen, and J. Hermens. 1989. Determination of
octanol/water partition coefficients for hydrophobic organic chemicals with the
"slow-stirring" method. Environ. Toxicol. Chem. 8:499-512.
8. Mabey, W.R., J.H. Smith, R.T. Podoll, H.L. Johnson, T. Mill, T.-W. Chou, J. Gates, I.W.
Partridge, H. Jaber, and D. Vandenberg. 1982. Aquatic Fate Process Data for Organic
Priority Pollutants. U.S. Environmental Protection Agency, Washington, DC,
EPA-440/4-81-014.
9. Wolfe, N.L., W.C. Steen, and LA. Burns. 1980. Phthalate ester hydrolysis: Linear free
energy relationships. Chemosphere 9:403-408.
10. Castro, C.E. and N.O. Belser. 1981. Photolysis of methyl bromide and chloropicrin. J.
Agric. Food Chem. 29:1005-1008.
11. Russell, D.J. and B. McDuffie. 1986. Chemodynamic properties of phthalate esters:
Partitioning and soil migration. Chemosphere 15(8):1003-1021.
12. Wolfe, N.L., R.G. Zepp, D.F. Paris, G.L. Baughman, and R.C. Hollis. 1977. Methoxychlor
and DDT degradation in water. Rates and products. Environ. Sci. Technol.
11(12):1077-1081.
-------
56
Fate Constants for Hazardous Waste Identification
13. Jeffers, P.M., L.M. Ward, L.M. Woytowitch, and N.L. Wolfe. 1989. Homogeneous
hydrolysis rate constants for selected chlorinated methanes, ethanes, ethenes, and
propanes. Environ. Sci. Technol. 23(8):965-969.
14. Leistra, M. 1970. The distribution of 1,3-Dichloropropene over the phases in soil. J. Agr.
Food Chem. 18:1124-1126.
15. Wolfe, N.L., LA. Burns, and W.C. Steen. 1980. Use of linear free energy relationships
and an evaluative model to assess the fate and transport of phthalate esters in the
aquatic environment. Chemosphere 9:393-402.
16. Sijm, D.T., H.M. Han Wever, P.J. de Vries, and A. Opperhuizen. 1989. Octan-l-ol/water
partition coefficients of polychlorinated dibenzo-p-dioxins and dibenzofurans:
Experimental values determined with a stirring method. Chemosphere 19(l-6):263-266.
17. Shiu, W.Y., W. Doucette, F.A.P.C. Gobas, A. Andren, and D. Mackay. 1988.
Physical-chemical properties of chlorinated dibenzo-p-dioxins. Environ. Sci. Technol.
22:651-658.
18. Doucette, W.J. and A.W. Andren. 1987. Correlation of octanol/water partition coefficients
and total molecular surface area for highly hydrophobic aromatic compounds. Environ.
Sci. Technol. 21(8):821-824.
19. Wolfe, N.L., R.G. Zepp, P. Schlotzhauer, and M. Sink. 1982. Transformation pathways
of hexachlorocyclopentadiene in the aquatic environment. Chemosphere 11(2):91-101.
20. Callahan, M.A., M.W. Slimak, N.W. Gabel, LP. May, C.F. Fowler, J.R. Freed, P.
Jennings, R.L. Durfee, F. C. Whitmore, B. Maestri, W.R. Mabey, B.R. Holt, and C. Gould.
1979. Water-related Environmental Fate of 129 Priority Pollutants. Volume II. U.S.
Environmental Protection Agency, Washington, DC, EPA-440/4-79-029b.
21. Faust, S.D. and H.M. Gomaa. 1972. Chemical hydrolysis of some organic phosphorus and
carbamate pesticides in aquatic environments. Environ. Lett. 3(3):171-201.
22. Hawkins, M.D. 1975. Hydrolysis of phthalic and 3,6-dimethylphthalic anhydrides. J.
Chem. Soc., Perkin Trans. 2:282-284.
23. Eadsforth, C.V. 1986. Application of reverse-phase h.p.l.c. for the determination of
partition coefficients. Pest. Sci. 17:311-325.
24. Ellington, J.J., F.E. Stancil, Jr., W.D. Payne, and C. Trusty. 1987. Measurement of
Hydrolysis Rate Constants for Evaluation of Hazardous Waste Land Disposal: Volume
II. Data on 54 Chemicals. U.S. Environmental Protection Agency, Athens, GA,
EPA/600/3-87/019.
25. Chapman, R.A. and C.M. Cole. 1982. Observations on the influence of water and soil pH
on the persistence of insecticides. J. Environ. Sci. Health B17(5):487-504.
26. Ellington, J.J. 1989. Hydrolysis Rate Constants for Enhancing Property-reactivity
Relationships. U.S. Environmental Protection Agency, Athens, GA, EPA/600/3-89/063.
27. Fiskel, J., C. Cooper, A. Eschenroeder, M. Goyer, J. Perwak, K. Scow, R. Thomas, W.
Tucker, M. Wood, and AD. Little Inc. 1981. An Exposure and Risk Assessment for
Cyanide. U.S. Environmental Protection Agency, Washington, DC, EPA-440/4-85-008.
28. Hamrick, K.J., H.P. Kollig, and B.A. Bartell. 1992. Computerized extrapolation of
-------
EPA/600/R-93/132
August 1993
Environmental Fate Constants for
Organic Chemicals Under
Consideration for
EPA's Hazardous Waste Identification Projects
Compiled and edited by
Heinz P. Kollig
Contributors: J. Jackson Ellington
Samuel W. Karickhoff
Brenda E. Kitchens
Heinz P. Kollig
J. MacArthur Long
Eric J. Weber
N. Lee Wolfe
Environmental Research Laboratory
Office of Research and Development
U.S. Environmental Protection Agency
Athens, GA 30605-2720
-------
DISCLAIMER
The information in this document has been funded by the United States
Environmental Protection Agency. It has been subjected to the Agency's peer and
administrative review and it has been approved for publication as an EPA document.
-------
TECHNICAL REPORT DATA.
(Please read Instructions on the reverse before c'omplet
1. REPORT NO. 2.
EPA/600/R-93/132
3.
4. TITLE AND SUBTITLE
ENVIRONMENTAL, FATE CONSTANTS FOR ORGANIC CHEMICALS
UNDER CONSIDERATION FOR EPA'S HAZARDOUS WASTE
IDENTIFICATION PROJECTS
5. REPORT DATE
August 1993
6. PERFORMING ORGANIZATION CODE
7. AUTHOR(S)
Heinz P. Kollig (Ed.)
8. PERFORMING ORGANIZATION REPORT NO.
9. PERFORMING ORGANIZATION NAME AND ADDRESS
Environmental Research Laboratory
U.S. Environmental. Protection Agency
Athens GA 30605-2720
10. PROGRAM ELEMENT NO.
AC5D1A
11. CONTRACT/GRANT NO.
12. SPONSORING AGENCY NAME AND ADDRESS
Environmental Research Laboratory - Athens, GA
Office of Research and Development
U.S. Environmental Protection Agency
Athens GA 30605-2720
13. TYPE OF REPORT AND PERIOD COVERED
14. SPONSORING AGENCY CODE
EPA/600/01
15. SUPPLEMENTARY NOTES
16. ABSTRACT
Under Section 301 of the Resource Conservation and Recovery Act (RCRA), EPA's
Office of Solid Waste is in the process of identifying chemicals to be considered in
projects called the hazardous waste identification projects. At this time, there are
some 200 chemical chemical constituents identified in these projects. This publica-
tion addresses environmental fate constants and chemical hydrolysis pathways for the
189 organic chemicals already identified. Chemical hydrolysis rate constants for
parent compound and products including structural presentation of the pathways are
presented. Redox rate constants are given for selected compounds. Sorption coeffi-
cients are presented for parents and products in terms of the octanol/water partition
coefficient and the organic-carbon-normalized sediment/water partition coefficient.
The ionization constant is given when this process affects sorption in the environ-
mental pH range.
17. KEY WORDS AND DOCUMENT ANALYSIS
a. DESCRIPTORS
b.IDENTIFIERS/OPEN ENDED TERMS
c. COSATi Field/Group
Hazardous waste
Pollutant fate constants
Hydrolysis rates
Sorption coefficients
Oxidation-reduction rates
Partition coefficients
18. DISTRIBUTION STATEMENT
RELEASE TO PUBLIC
19. SECURITY CLASS (This Report)
UNCLASSIFIED
)
21. NO. OF PAGES
183
20. SECURITY CLASS /This page)
UNCLASSIFIED
22. PRICE
EPA Form 2220-1 (Rev. 4-77) previous edition is OBSOtETr
1 \
-------
FOREWORD
As it becomes more and more obvious that many thousands of potentially hazardous
manmade chemicals find their way into ambient environments, the need for a
comprehensive understanding of the distribution of chemicals and their transport and
transformation reaches a higher level of importance. As part of this Laboratory's research
on the occurrence, movement, transformation, impact, and control of chemical
contaminants, the Chemistry Branch and the Measurements Branch determine the
occurrence of unexpected organic chemicals in the environment, define mechanisms of
transport and abiotic transformation, and develop and apply advanced methods to predict
and measure physical and chemical transformation and equilibrium constants for use in
exposure assessment.
Under Section 301 of the Resources Conservation and Recovery Act (RCRA), EPA's
Office of Solid Waste is required to develop and promulgate criteria for identifying and
listing hazardous wastes, taking into account, among other factors, persistence and
degradability in the environment of selected chemicals. A requirement of the legislation
is for EPA to take an initial step toward defining wastes that do not merit regulation
under Subtitle C of RCRA and can be managed under other regimes. For establishing
exemption criteria, the Agency has selected some 200 chemical constituents that may
occur in the various wastes. This report explains some of the means by which these
chemicals may be transformed and provides hydrolysis degradation pathways and fate
constants for the selected chemicals.
Rosemarie C. Russo, Ph.D.
Director
Environmental Research Laboratory
Athens, Georgia
iii
-------
ABSTRACT
Under Section 301 of the Resource Conservation and Recovery Act (RCRA), EPA's
Office of Solid Waste is in the process of identifying chemicals to be considered in projects
called the Hazardous Waste Identification Projects. This publication addresses the 189
organics already identified in these projects. The environmental fate constants and the
chemical hydrolysis pathways of these chemicals are listed. Chemical hydrolysis rate
constants for parent compounds and products including structural presentation of the
pathways are presented. Redox rate constants are given for selected compounds.
Sorption coefficients are presented for parents and products in terms of the octanol/water
partition coefficient and the organic-carbon-normalized sediment/water partition
coefficient. The ionization constant is given when this process affects sorption in the
environmental pH range.
iv
-------
Table
of Contents
Part 1
Introduction
Hydrolysis
General
a ologeTi&ted Alfpftc^ics • ..................... 6
Simple halogenated aliphatics .. 6
Polyhalogenated aliphatics.7
Organophosphorus Esters - ........ 8
Carboxylic Acid Esters
Amides
Carbamates 10
Nitriles................... 10
Sorption10
Neutral Organic Compunds.......... 10
Ionizable Organic Compounds.... 11
Estimated data 13
Abiotic Redox Transformations of Organic Compounds 14
Convention of Writing Redox Reactions 15
Reduction IS
Oxidation 16
Descriptions of Redox State of the System 16
Eh .... 16
pH .... 17
Kinetics of Reaction in Heterogenous Systems.......~..~..~~..............~~.~.........~~~~~~...... 17
Calculation of Rate Constanta 17
Reductive Processes 17
Nitroaromatics 17
Halogenated Hydrocarbons 17
Oxidative Processes 18
Aldehydes 18
Amines 18
Table 1 19
Table 2 53
References 55
-------
Part 2
x* nwuapuiuvuc
2. Acetone [[[
3. Acetonitrile
4. Acetophenone...........
5. Acrolein
6. Acrylamide
7. Acrylonitrile
8. Aldrin
9. Aniline[[[
11. ArSlXlltO hww..............wmm.wHWH*.w»i>.wmw».HWwm....MWWWM«>.m—..mw
14. Benz[a]anthracene
15. Benzene
16. Benzidine
17. Benzo[6]fluoranthene
18. Benzo[a]pyrene
19. Benzotrichloride
20. Benzyl alcohol[[[
21. Benzyl chloride
23. fiis(2-chloroethyl)ether
24. Bis (2-c hlo rois op ropyl) ether
25. £zs(2-ethylhexyl)phthalate
26. Bromodichloromethane
27. Bromomethane
28. Butanol
29. Butyl benzyl phthalate
30. 2-.sec-Butyl-4,6-dinitrophenol
32. Carbon disulfide ••¦••••a«Haaa«aaaa*MHn«»a«ta«a*a*aaa«**MMata«aaaata«a*a«M*«t4aaaa*aa*a*aa«a(a*»«*«aa
33. Carbon tetrachloride[[[
34. Chlordane...... ^••••••••fimatataataaaaaMMfaatMattvaaaafMaMfaatMMaNataaaaMaavtaaaMaaaaHatMaaaaMaaM
35. p-Chloroaniline aaaaaaaNaaa««tataMfaaa»aat«M««Mata«aMaaaMMa«a«*a*t*«*aa<**»t«aa*aat*a««af«aM*«*«a«aM
36. Chlorobenzene
37. Chlorobenzilate
38. 2-Chloro-l,3-butadiene[[[
39. Chlorodibromomethane aiaaa*aaaa*M«>faav«ftaiaaaataaaa««***«t««t*aa***«a»ia**«*fa*«*a*«at«tM**aa»«
40. Chloroform ta»»»a«t»afM»MttW«Ha<»»«t»ttaw»ta«»»«aMa»>«ttM»waa»aa—>MatM»*<»a»aaaw«»aa»a*a«a>»a
41.. Chloromethane M*aM«aaaaaaaaaaaMa*«a«attaMaaaa*aaaa«aaM«aaaaaMaaaaMaaaaamaaa«M*M»aaaM«aM«aaa*«a
42. 2-Chlorophenol aaaaaaaaaaaaaataaaaaaaaaiaaMaaaaaaaaaaaaaaaaaaaMaaaaaaaaaaaaaaaaaaaaaaaatatataataaaaaaaaaaaa
43. 3-Chloropropene
45. Chrysene ¦a««ta«f>aaia«a*aa«Nama*a««M«fH«H«aaaHMaMHHaHi*aaa>aaaaaaMa«a*aaaa«a«aMMaaaa«a«aaH**aa«*»
47. o-Cresol ia*af*»aMMa«a(«awaM**Ma*aaaaaaaMaM**ta««*««*a«aMa«aaa*aaM*aa«aMa«a««ti**Maa*aaaa«aaaa««aaaMaaai
-------
Cyanide..................— 85
2,4-Dichlorophenoxyacetic acid- .. .. .. 86
. DDD 86
. DDE 87
. p.p'-DDT 87
Diallate ••••••(••••f«taM««M«*faafaftiaf»«*aMaM«Ma«aMt(a«aM*a««aMM«atfMMM»*aaMaaaa»aaaaa«aMafaaaaaaa«a 88
Dibenz[a,A]anthracene 88
1,2-Dibromo-3-chloropropane „ 89
Dibromomethane 90
1,2-Dichlorobenzene —90
1,4-Dichlorobenzene 91
3,3'-Dichlorobenzidine 91
Dichlorodifluoromethane avaaaatatNaatatamaaafaaaattaMtaaaaavfafaaaiaaMMHaMaaMaitMaataaaaa 92
1,1-Dichloroethane aaaaaaaataamNaaMaatataaaaaaaMaaaaaaavaMatfaaaaaaaaaaaaaaaaaafaantatavtvtHaaaaaa 92
1 ,2-Dichloroethane 93
1.1-Dichloroethylene •aaMaaaaaaaaa>a»»a»aaaaaMaa>aa—aaaaaa»»aaa»»»»*Ma>>aw»aaaaa> 96
1.3-Dichloropropen e aaaaaaaaaaaaaaaM4aMaaa«aMaaaaaMaaaaaaaaaaa«»Maaa*aa* 97
Dieldrin
maa*fMaaaaaafa«a*a«Maaaaa»a«aaaaaa«aaaaaaaaaa*t««aaa*aaaaaaaa»aaaaaaaaaa«a*»Hatataf«aaaaaaaaaaiaaaai«( 98
Diethyl phthalate f*««aaaaaaaaNa*aaaM«a«*a(a«a»aaaaa*>a«aaaa(Ma«aiaMa(aaavaiaa*a»aMaa«»a«Maata«aaaaHt 99
Diethylstilbestrol .. .... 100
Dimethoate (opposite page) 100
3,3'-Di2nethoxybenzidine aiaaaataataaaaaaaaaaaaaaMMaaamaaaaaaaaaataaaaaaaaMamaMaaataaaaaaat 102
7,12-Dimethylbenz[a]anthracene aata*aaaa«aaa*a*aaaaaa»aaaa«aaataaaaM«a«aaMaa«ataatt«aaa*i 102
3,3'-Dimethylbenzidine 103
2.4-Dimethylphenol a*aaaaaaataaaaaaaa»taat«afaHaaaaaaa«aaaa(MaH*aaaaaaaaaataHaMaaaaaM«MMaaaiaaa 103
Dimethyl phthalate 104
1.3-Dinitrobenzene [[[ 105
2.4-Dinitropheno l
»»aa*aaa*a«»aaataa«M«aaaaaaaaaaa»aaataaaa«aaa«ataaaaaaaaaaa«aaaatai 105
2,4-Dinitrotoluene aaaa*aa«aaaa*a(aa«a(a«»taa»a«aMa>aaaNMaaaaa4aaa*a«aa»aaaaaa(aaaM*maM*iaaaaaa»a« 106
2,6-Dinitrotoluene at*ta»aaaaaaaaaaaaa»a«aaaa«a«aaaaaaaaaaaaaaaaaM»ataaaa»aaaaa«aa*aaaaaaM«aaaMaM«aM 106
Di-n-butyl phthalate [[[ 107
Di-zi-octyl phthalate i»aMt»»»«>ai»—>a«»M»woMam«H«wa»w»a«naa»«aa»«taaMa»»aaM««»a 108
1,4-Dioxane .. .. 109
. 2,3,7,8-TCDDioxin
itaMaaaaaaaaaaxafaaaxaaaattaaaaataaaaaaaaaaafaaaaaaaaaaaaaaa 109
• 2,3,7 j8*P6CDI}ioxizis 1X0
2,3,7,8-HxCDDioxins aaaaaaaaaaaaaaaaaaaaaataaaaaaaaaMaaaaaataaaaaHaMaaataaaaaMaaaaaaaaaaaaaaaMaaa 110
-------
96.
97.
98.
99.
100.
101.
102.
103.
104.
105.
106.
107.
108.
109.
110.
111.
112.
113.
114.
115.
116.
117.
118.
119.
120.
121.
122.
123.
124.
125.
126.
127.
128.
129.
130.
132.
134.
135.
136.
137.
138.
139.
140.
141.
Disulfoton
Endosulfan
Endrin
Epichlorohydrin
2-Ethoxyethanol
Ethyl acetate
Ethylbenzene
Ethyl ether
Ethyl methacrylate
Ethyl methanesulfonate
Ethylene dibromide.......
Famphur
Fluoranthene
Fluorene
•«••••••••••••••<
Formic acid
Fur an
2,3,7,8-TCDFuran
1,2,3,7,8-PeCDFuran .....
2,3,4,7,8-PeCDFuran
2,3,7,8-HxCDFurans
2,3,7,8-HpCDFurans
OCDF
Heptachlor
Heptachlor epoxide
Hexachlorobenzene
Hexachlorobutadiene ......
alpha-nCK NMNI
6efo-HCH
Hexachlorocyclopentadiene
Hexachloroethane
•••••••••
aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
Hexachlorophene
Indeno[l,2,3-caaaa
MaaMaaaa*M4M«MMaaa«am»aaaMaHMa«aaaaaaM*MaNaaHaa«
«HM«H«HMa«a»H«m«HtaMaaaaaM«n«mflaM«Maaa«m
aaaaaaaa*aaaaa»«aa»a«aa
aaaaaaaaaaaMaaaaaaaaaaaaaaaMi
aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaMtaaaaaaaaaaaaaaMaaaaaMaaa
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viii
-------
142. Naphthalene 141
143. 2-Naphthylamine 141
145. Nitrobenzene 142
146. 2-Nitropropane 142
147. JV-Nitroso-di-re-butylamine 143
148. JV-Nitrosodiethylamine [[[ 143
149. JV-Nitrosodimethylamine[[[ 144
150. iV-Nitrosodiphenylamine 144
151. Af-Nitroso-di-rc-propylamine 145
152. JV-Nitrosomethylethylamine 145
153. iV-Nitrosopiperidine 146
154. 2V-Nitrosopyrrolidine 146
155. Oetamethyl pyrophosphoramide 147
156. Parathion [[[ 148
157. Pentachlorobenzene 149
158. Pentachloronitrobenzene[[[ 149
159. • Pentachlorophenol . 150
160. Phenol 150
161. Phenylenediamine 150
162. Phorate 151
163. Phthalic anhydride 152
164. Polychlorinated biphenyls 152
165. Pronamide......H..»..»....H......H„..m.....».H«..............M.....M.........».........«...... 153
166. Pyrene[[[ 153
167. Pyridine 154
168. Safrole 154
171. Strychnine 155
172. Styrene 155
173. 1,2,4,5-Tetrachlorobenzene 156
174. 1,1,1,2-Tetrachloroethane „ 156
175. l,l»2>2-Tetrachloroethane 157
176. Tetrachloroethylene .. 157
177. 2,3,4,6-Tetrachiorophenol 158
178. Tetraethyl dithiopyrophosphate 159
180. Toluene 160
181. 2,4-Toluenediamine ..... 160
182. 2,6-Toluenediamine 161
183. o-Toluidine aaaaataaMaaMaMaaMMfHtatnttaffnfanaftMaaaaaaaaamatMtaMttfMHaavatMtataaaatMfaNaaa* 161
184. p-Toluidine •ta««Maa*aaaaat«aaaf«a*aaa««ataa«aM*«aa«aa(*atMaaa»a*amaaaata««*ta**«aaaa*M«aaf*aaaa«aaat«aaa 162
-------
190
191.
192,
193
194
195.
196
197,
198.
199,
201,
202,
Trichloroethylene
Trichlorofluoromethane
2.4.5-Trichloropheno l
2.4.6-Trichlorophenol.......................
2,4,5-Trichlorophenoxyacetic acid
2-(2,4,5-Trichlorophenoxy)propionic acid (Silvex)
1,2,3-Trichloropropane
l,l,2-Trichloro-l,2,2-trifluoroethane.
1,3,5-Trinitrobenzene
TWs(2,3-dibromopropyl)phosphate
Vinyl chloride
Xylenes
166
.. 166
.. 167
.. 167
.. 168
.. 168
.. 169
.. 170
170
171
172
172
x
-------
Part f 1
Introduction
Assessment of potential risk posed to humans by man-made chemicals in the environment
requires the prediction of environmental concentrations of those chemicals under various
environmental reaction conditions. Whether mathematical models or other assessment
techniques are employed, knowledge of equilibrium and kinetic constants (fate constants)
is required to predict the transport and transforation of these chemicals.
Under section 301 of the Resource Conservation and Recovery Act (RCRA), EPA's Office of
Solid Waste (OSW) has identified wastes that may pose a substantial hazard to human
health and the environment. RCRA requires that EPA develop and promulgate criteria
for identifying and listing hazardous wastes, taking into account, among other factors,
persistence and degradability in the environment of selected chemicals.
EPA continues to believe that the Agency must assure continuity of the hazardous waste
program while developing appropriate revisions. While fully preserving existing hazardous
waste identification rules, EPA is considering alternatives to take an initial step towards
defining wastes that do no merit regulation under Subtitle C and that can and will be
safely managed under other regulatory regimes.
EPA plans to hold a series of public meetings to solicit input on how best to insure that
waste mixtures containing hazardous wastes and wastes derived from the treatment,
storage or disposal of hazardous wastes do not pose unreasonable risks to health and the
environment. This effort will complement EPA's ongoing program to improve RCRA
regulations.
In the course of developing appropriate revisions, OSW is in the process of identifying
chemicals to be considered in projects called the Hazardous Waste Identification Projects.
At this time, there are some 200 chemicals contituents identified in these projects. The
environment fate constants and the chemical hydrolysis pathways of the 189 organics are
listed in Part I and Part II of this report, respectively. Inorganic compounds are not
addressed in this publication.
For all selected organic compounds, OSW requested that the Environmental Research
Laboratory-Athens (ERL-Athens):
a) identify those that do not hydrolyze.
b) identify those that do hydrolyze and list products of degradation including hydrolysis
rate constants for parents and intermediates obtained either through laboratory
experiments at ERL-Athens, literature searches, or pathway analyses.
-------
2
Fate Constants for Hazardous Waste Identification
c) obtain sorption data as the organic-carbon-normalized sediment-water partition
coefficient either through laboratory experiments at ERL-Athens, literature searches,
or computational techniques.
d) to the extent that current scientific knowledge will permit, identify those that will be
subject to other important degradation reactions and identify products of these
reactions including rate constants.
For compounds identified as having no hydrolyzable functional group (NHFG), hydrolysis
will not occur by abiotic reaction pathways in the pH range of 5 to 9 at 25°C.
The compounds identified as having non-labile functional groups (NLFG) will not
hydrolyze to any reasonable extent. Although a molecule with a non-labile functional
group contains one or more heteroatoms, they react so slowly over the pH range of 5 to 9
at 25°C, that their half-lives will be greater than 50 years, if they react at all.
Polychlorinated biphenyls (PCBs) have been addressed here only as a class because of the
many different congeners of these compounds. The given Chemical Abstract Service
number 1336-36-3 is the number for the general class of Aroclors without designating any
specific Aroclor. Because PCBs will not hydrolyze to any reasonable extent, our Pathway
Analysis Team classified them as non-labile. The sorptive capacity, however, will be
different from congener to congener. We have found reported log values ranging from
2.59 to 11.20. Therefore, a single sorption value for the class of Aroclors was not
assigned.
The chemical hydrolysis pathways of compounds with negative boiling points that exist as
gases at room temperature were not addressed in this report.
Some compounds may exist in the environment as ionized species. The transformation
pathways show these species in the neutral form for better identification. It should be
understood that both the persistence and mobility of a chemical in the environment is
influenced by many environmental factors that may change from environment to environ-
ment. The values in this document are for those conditions specified in the references.
A team of EPA scientists met several times to discuss the rates and probable pathways of
transformation for hydrolysis and redox reactions. The methods used to arrive at the
reaction products were based primarily on the team's experience with similar compounds,
their knowledge of the theory of these processes, and their understanding of structure-
activity relationships. For hydrolysis, the team's decisions are identified in Table 1 with a
zero in the Reference column. Final stable products are identified as containing either no
hydrolyzable functional group (NHFG) or a non-labile functional group (NLFG) in the
Comment column.
Literature searches were conducted afterwards to find needed fate data for the intermedi-
ate products of hydrolysis. If the literature failed to provide the required data, they were
determined in the laboratory for some compounds.
This report is composed of two parts. Part I includes text and data on chemical hydrolysis,
sorption, and redox reactions. In the hydrolysis section hydrolysis kinetics are elucidated
for the chemical classes of halogenated aliphatics, organophosphorus esters, carboxylic acid
-------
Parti
esters, amides, carbamates and nitriles. In the sorption section, the sorption of neutral and
ionizable organic compounds is addressed including computational techniques. In the
redox section, the kinetics of the unexplored area of the heterogeneous redox reactions is
elucidated. Part I concludes with a table listing hydrolysis products (intermediate and
final) including rate constants for parents and intermediates, and sorption data for parents
and for intermediate and final products, and a table listing computed redox rate constants
at different levels of organic carbon for selected halogenated aliphatics and nitroaromatics.
Part II includes the chemical structures of all organic compounds under consideration in
the projects and the pathways of chemical hydrolysis of these compounds that undergo this
transformation. When a compound was identified as NHFG, the text with the structure will
say that the compound will not hydrolyze. When a compound was identified as NLFG, the
text with the structure will say that the compound will not hydrolyze to any reasonable
extent. When a compound might be subject to other abiotic transformation processes, the
text with the structure will point this out; however, these processes have been identified.
-------
Parti 5
Hydrolysis
General
In general, hydrolysis is a bond-making, bond-breaking process in which a molecule, RX,
reacts with water forming a new R-0 bond with the oxygen atom from water and cleaving
an R-X bond in the original molecule. One possible pathway is the direct displacement of X'
with HO" as shown in Equation 1.
RX + HjO ~ ROH + HX (1)
The detailed mechanisms of hydrolytic processes are well defined and have been shown to
involve the formation of intermediates such as protonated species, anions and carbonium
ions, as well as combinations of these intermediates.
Generally, hydrolysis of organic compounds in water under pH-buffered conditions is first-
order in the concentration of the organic species ([RX]), where the rate of hydrolysis
(d[RX]/d£) is proportional to the concentration of pollutant RX:
d[RX]
dt
(2)
Where k^, is the observed pseudo-first-order disappearance rate constant. The first-order
dependence of the disappearance rate on [RX] is important, because it means that the half-
life (tyg) of the reaction described by Equation 2 is independent of [RX], Thus, the results
obtained at a high RX concentration can be extrapolated to lower RX concentrations if other
reaction conditions are held constant. The half-life of the reacting compound is given by
Equation 3:
In 2 0.693
where kcan include contributions from acid-catalyzed or base-mediated hydrolysis, nucleo-
philic attack by water, or catalysis by buffers in the reaction medium.
For abiotic hydrolysis, the general expression for k^, is given by:
+ + K + (4)
where ka and kb are the specific acid and base second-order rate constants, respectively; kn
is the neutral hydrolysis rate constant; and and kA are the general acid-catalyzed and
base-mediated hydrolysis rate constants, respectively. In Equation 4, [H+] and [HO ] are the
hydrogen and hydroxyl ion concentrations, respectively, and [HA] and [A] are the concentra-
-------
6
Fate Constants for Hazardous Waste Identification
tions of the ith and the jth pair of general acids and bases in the reaction mixture, respective-
ly.
In Table 1, ka, kb, and kn values are reported for the particular chemical at 25°C (+/-4°C). A
half-life at 25°C can be calculated by using Equation 4 to calculate k#, followed by Equation
3 to calculate the time at 50% hydrolysis. Concentration and time units used are molar (M)
and year (Y), respectively. Products of hydrolysis are listed indented under the parent
compound, e.g., acetonitrile (parent): acetamide is the first hydrolysis product and it then
becomes an intermediate by hydrolyzing to a secondary product, acetic acid. Both products
are indented according to the order of their appearance in the hydrolysis pathway of the
original parent.
Hydrolysis rate constants that were reported in the literature at an elevated temperature
were reanalyzed with RATE28 to extrapolate the values to 25°C. These reanalyzed values are
identified by RATE in the Comment column. Those compounds that were identified as non-
hydrolyzable or non-labile were designated as rNHFG' and 'NLFG', respectively, in the
Comment column.
Halogenated Aliphatics
Simple halogenated aliphatics
Hydrolysis of the simple halogenated aliphatics (halogen substitution at one carbon atom) is
generally pH independent, resulting in the formation of alcohols by nucleophilic substitution
with water (Equation 1). Although a number of the simple halogenated aliphatics are
susceptible to base-mediated hydrolysis, the rate term for the base-medi-
ated process will not contribute to the overall hydrolysis rate under environmental conditions.
The halogenated methanes, except for the trihalomethanes, hydrolyze by direct nucleophilic
displacement by water (Sj.,2 mechanism). An increase in the number of halogen substituents
on carbon increases the hydrolysis half-life because of the greater steric bulk about the site
of nucleophilic attack. The type of halogen substituent also affects reactivity. For example,
hydrolysis data indicate that the fluorinated aliphatics are much more stable than the
chlorinated aliphatics, which in turn are more stable than the brominated aliphatics (F > CI
> Br). This trend in reactivity reflects the strength of the carbon-halogen bond that is broken
in the nucleophilic substitution reaction.
Hydrolysis of the trihalomethanes, or haloforms, is thought to occur initially by proton
abstraction and subsequent formation of the carbene, which reacts with HO~ to form carbon
monoxide and chloride ion:41
CHCI3 + HO"
¦CCI3
:CCIj + 2 HO'
"CCI3 + H20
:CCl2 + q|-
CO + 2CI" + h2o
-------
Parti 7
In contrast to the halogenated methanes which have hydrolysis half-lives on the order of
years, the hydrolysis half-lives for allylic and benzylic halides are on the order of minutes to
hours. The hydrolysis of these chemicals occurs through an indirect nucleophilic displace-
ment by water (S^-l mechanism). The dramatic increase in reactivity is due to the structural
features of these compounds that allow for delocalization, and thus, stabilization, of the
carbonium ion intermediate. Resonance structures can be drawn for the allylic and benzyl
carbonium ions that delocalize the positive charge over several carbon atoms.
The lack of reactivity observed for vinyl halides and halogenated aromatics is a reflection of
the high energy pathway required for nucleophilic substitution at vinylic and aromatic
carbons. Vinyl and phenyl carbonium ions have been observed, but their formation requires
very reactive leaving groups.
Polyhalogenated aliphatics
The hydrolysis kinetics for the polyhalogenated ethanes and propanes are somewhat more
complex than for the simple halogenated aliphatics. In addition to nucleophilic substitution
reactions, degradation of these compounds can occur through the base-mediated loss of HX.
Depending on structure type, elimination or dehydrohalogenation may be the dominant
reaction pathway at pITs characteristic of ambient environments. The loss of HX occurs
through a bimolecular elimination (E2) reaction in which abstraction of the hydrogen beta
to the halogen (X) occurs simultaneously with cleavage of the C-X bond:
^•'OH
pHp1
This process often results in the formation of halogenated alkenes, which can be more
persistent and of more concern than substitution products42.
The distribution of reaction products resulting from the hydrolytic degradation of the
polyhalogenated ethanes and propanes will depend on the relative rates for the nucleophilic
substitution and dehydrohalogenation reaction pathways. Furthermore, because dehydro-
halogenation is pH dependent, product distribution will also be pH dependent.
A wide range of reactivity is observed for these compounds; the environmental hydrolysis
half-lives in years range over 7 orders of magnitude. For a number of the polyhalogenated
aliphatics, it is apparent that both neutral and base-mediated hydrolysis will occur at
ambient environmental pH values and that the relative contributions of these processes will
be dependent on the degree and pattern of halogen substitution.
As with nucleophilic substitution reactions, rates of dehydrohalogenation reactions will be
dependent on the strength of the C-X bond being broken in the elimination process.
Accordingly, it is expected that the ease of elimination of X will follow the series Br> CI > F.
—C—C— + X' + Ha©
-------
B
Fate Constants for Hazardous Waste Identification
Epoxides
The hydrolysis of epoxides is pH dependent and can occur through acid-, neutral-, or base-
promoted processes. Because the acid and neutral processes dominate over ambient environ-
mental pH ranges, the base-mediated process can often be ignored. The products resulting
from the hydrolysis of epoxides are diols, and to a lesser extent, rearrangement products:
„ A h2o ?T Vs?
c'^3 B,—C—C—R4 + R,—C—C—R4
X Rz Ra Rz
Organophosphorus Esters
Mechanistic studies of organophosphorus esters have demonstrated that hydrolysis occurs
through direct nucleophilic displacement at the central phosphorus atom and does not involve
formation of a pentavalent intermediate with HjO or HO~43,44. Accordingly, hydrolysis rates
for phosphorus esters will be sensitive to electronic factors that alter the electrophilicity of
the central phosphorus atom and steric interactions that impede nucleophilic attack. For
example, substitution of sulfur (P=S) for oxygen (P=0) in the ester moiety will reduce the
electrophilicity of the phosphorus center because of the weaker electron withdrawing effect
of sulfur. Accordingly, phosphorothioate and phosphonothioate esters will exhibit greater
stability towards neutral and base-mediated hydrolysis than their respective 0-substituted
counterparts.
An interesting feature of the hydrolytic degradation of phosphorus esters is that carbon-
oxygen or carbon-sulfur cleavage may also occur. It is generally observed that base-mediated
hydrolysis favors P-0 cleavage, which is shown in the first chemical reaction below, and that
neutral and acid catalysis favors C-0 or C-S cleavage, which is shown in the second reaction
below. As a result, hydrolysis mechanisms and product distribution for the organophosphorus
esters will be pH dependent.
R10.
F^cr"
!?
P-0-GH2R2 + OH
^cr"
'—O—CH2R2 + H2O
^O—p—O—CH2R2 + HOB,
OH
RiOs?
r^P-OH + HOCH2R2
tal
Because hydrolysis of phosphorus esters results in the formation of phosphate mono- and
diesters, assessment of their hydrolytic activity is necessary. At any ambient environmen
^H;oildicL^9dn6eah$lddi^ra-Bf1^ifi aasiiBtis pwiihariijbeQHTi^brtaiiA, tauteraeuUa} kydpetyBielyf
these species must be considered. Hydrolysis of the dialkyl monoion to yield monoalkyl
-------
Parti 9
products proceeds at a rate approximately a factor of 10 less than that of the triester.
Hydrolysis of the resulting monoalkyl ester (dianion) proceeds at a rate of approximately one
half that of the triester. Hydrolysis of the monoester has been shown to occur through
nucleophilic attack on the phosphorus rather than carbon-oxygen cleavage86.
Carboxylic Acid Esters
Hydrolysis of carboxylic acid esters results in the formation of a carboxylic acid and an
alcohol:
Hydrolysis mechanisms of carboxylic acid esters have been thoroughly investigated. Although
nine distinct mechanisms have been proposed48, our comments will be limited to the two most
common mechanisms involving acyl-oxygen bond cleavage by acid catalysis (Aac2) and base
mediation (BAC2). Hydrolysis via the Aac2 mechanism involves initial protonation of the
carbonyl oxygen. Protonation polarizes the carbonyl group, removing electron density from
the carbon atom and making it more electrophilic and thus more susceptible to nucleophilic
addition by water. The base-mediated mechanism (BAC2) proceeds via the direct nucleophilic
addition of HO- to the carbonyl group. Base mediation occurs because the hydroxide ion is
a stronger nucleophile than water. Although neutral hydrolysis of carboxylic acid esters does
occur, the base-mediated reaction will be the dominant pathway in most natural waters.
Generally, acid hydrolysis will dominate in acidic waters with pH values below 4.
Both electronic and steric effects can significantly alter the reactivity of carboxylic acid esters.
Because the acid-catalyzed process for both aliphatic and aromatic esters is relatively insensi-
tive to structural changes, observed changes in the magnitude of k^, with structure are due
primarily to changes of kb, and to a lesser extent, kn. Based on the mechanism for base
mediation (BAC2), we would expect that electronic factors that enhance the electrophilicity of
the carbon atom of the carbonyl group would make it more susceptible to nucleophilic attack
by HO". The electron-withdrawing groups can be substituents of either the acyl group
(EC(O)} or the alcohol portion of the ester.
Hydrolytic degradation of amides results in the formation of a carboxylic acid and an amine:
RrC-O—R2 + H20
?
R-C-OH + HOR2
Amides
+
r
HN—Rg
In general, amides are much less reactive towards hydrolysis than esters. Typically, half-
lives for amides at ambient environmental conditions are measured in hundreds to thousands
-------
10
Fate Constants for Hazardous Waste Identification
of years8. This observation can be explained by the ground-state stabilization of the carbonyl
group by the electron donating properties of the nitrogen atom:
This stabilization is lost in the transition state leading to the formation of the tetrahedral
intermediate. The result is that the hydrolysis of amides generally requires base or acid
catalysis, both of which can compete at neutral pH.
Carbamates
A carbamate is hydrolyzed to an alcohol, carbon dioxide, and an amine:
Carbamates are susceptible to acid, neutral and base hydrolysis, although in most cases, base
hydrolysis will dominate at environmental conditions. In an analogous manner to carboxylic
acid ester and amide hydrolysis, electron-withdrawing substituents on either oxygen or
nitrogen will accelerate the rate of hydrolysis. The most dramatic differences in reactivities
are observed when the hydrolysis half-lives of primary (Rj=H, R^alkyl) and secondary
(R1=alkyl, R2=alkyl) carbamates are compared. The primary carbamates hydrolyze at rates
that are approximately 6 to 7 orders of magnitude faster than the corresponding secondary
carbamates.
Nitriles are hydrolyzed to give a carboxylic acid and ammonium ion. Hydrolysis occurs
through the intermediate amide:
R—C—N—R
+
Nitriles
o
o
R-C-N
Base-mediated hydrolysis appears to be the dominant hydrolysis pathway at pH 7.
-------
Parti 11
Sorption
Neutral Organic Compounds
Partitioning between water and natural soils, sediments, and aquifer materials is an
important process affecting transformation rates, toxicity, and the ultimate disposition of
organic chemicals in the environment. Research focusing on the partitioning of neutral
organic compounds has shown that adsorption of these compounds is usually controlled by
hydrophobic interactions. As a result, the affinity that a natural sorbent has for neutral
organic solutes, in most cases, can be reliably estimated from characterization (quantification)
of the hydrophobicity of chemical and the sorbent. Organic carbon content has been used
almost exclusively as a measure of the hydrophobic nature of natural sedimentary material
(organic matter or volatile solids content has also been used but not as widely). To
quantitatively characterize the hydrophobic nature of organic compounds, researchers have
used various measurable parameters, including octanol-water partition coefficients (K^),
water solubility (corrected for crystal energy), reverse phase HPLC retention, and topological
parameters of the compounds such as calculated surface area. Generally, octanol-water
partition coefficients have been used extensively for estimating the partitioning of organic
compounds to sedimentary materials.
lonizable Organic Compounds
Predicting the partitioning of ionizable organic compounds is not as straightforward as for
the neutral compounds. These compounds, whether they are acids or bases, can exist as ions
in solution depending upon the pH of the solution according to the following equations. For
acids:
K = EH m i (5)
[HA]
and bases:
if = mm (©
* [HB]
where [H+] is the hydrogen ion activity, [HA] is the neutral organic acid activity (or
concentration), [A] is the organic acid anion activity, [B] is the neutral organic base activity,
[HB+] is the protonated organic base activity, and Ka is the acid dissociation or ionization
constant.
In general, more effort has been expended investigating the sorption of organic acids than the
sorption of organic bases. For organic acids, adsorption can be modeled to sediments, soils,
and aquifer materials in a similar manner to that of the neutral compounds, after taking
into account ionization, as long as the pH is not more than one unit above the pKa of the
compound46.
Compounds with low pKa values are more problematic. Adsorption of these compounds occurs
predominantly by the anionic species through modified hydrophobic interactions47. Therefore,
an estimate of a partition coefficient from the of the neutral species would significantly
-------
12
Fate Constants for Hazardous Waste Identification
overestimate the magnitude of adsorption. Jafvert et al.48 and Jafvert47 have investigated the
partitioning behavior of these and similar compounds in the octanol-water system and in sediment-
and soil-water systems. For example, Jafvert47 has reported on the sediment-water distribu-
tion of 8ilvex in 13 soils or sediments. If the partition coefficients (in which the pH of the
slurry is greater than 7) are regressed versus the fraction organic carbon, a value of log Kx
- 1.8 is obtained for the organic-carbon-normalized partition coefficient, Kx. The log of
the neutral form of silvex is 3.8. Similar results for pentaehlorophenol and 4-chloro-a-(4-
chlorophenyl)benzeneacetic acid (DDA) suggest that the partition coefficient (at pH 7.0) of the
anionic form of these compounds is approximately two orders of magnitude less than the
respective values of the neutral form of these compounds.
Unlike anionic organic compounds, which partition more weakly than their neutral counter-
parts, organic cations tend to partition more strongly than the corresponding unprotonated
bases. Also, unlike organic anions, which partition largely through modified hydrophobic
interactions, the organic cations can undergo cation (or ligand) exchange reactions. Pyridine,
for example, is an organic base that has a pKa value of 5.3. At pH 7, a small fraction (2.2%)
will exist as an organic cation in aqueous solution. Because the cationie species is expected
to adsorb more strongly to most natural soils, sediments, and aquifer materials than the
neutral species, an organic-carbon-normalized partition coefficient (K^) may severely
underestimate the adsorption of this compound at near-neutral pH. Because no predictive
methods exist for describing the partitioning of organic cations to natural matrices, however,
the organic-carbon-normalized partition coefficient calculated from the of the neutral
species (not accounting for ionization) is given in Table 1. For virtually every sediment and
aquifer material, this constant will underpredict the true magnitude of adsorption of these
compounds, with the error intensifying as the organic carbon content of a sediment or aquifer
material decreases.
For neutral compounds and organic bases with pKa values below 6, the organic-carbon-
normalized partition coefficients in Table 1 have been calculated using the relationship,
log = log K^- 0.32 (7)
given by Hassett et al.49 This correlation was calculated from adsorption isotherms of 13
organic chemicals, representing several classes of compounds, using 14 different sediment and
soil samples. This correlation adequately predicts partitioning of several classes of organic
compounds, including chlorinated and nonchlorinated aromatic and alkyl hydrocarbons. Use
of this correlation will generally be valid for soils, sediments, and aquifer materials that have
organic carbon contents greater than 0.1%.
For organic acids, the pKa must be considered in the computation of the Kx. The following
relationships were used according to the range of pKa values:
pKa > 9: Kx = 1.05
(8)
-------
Parti 13
6 < pKa < 9: K„ = 1.05^'82)
(9)
1.0+ f_
[HI
which simplifies at pH 7 to:
K
OC
1.05 x 10 7 x Kfwn)
10"7 - Ka
(10)
pKa < 6: log K„ = log - 2
(11)
For organic bases, the pKa value was considered in the computation of the Kx, where pKa =
14-pKb. Equation (7) was used for compounds with pKa values of less than 6. For organic
bases with pKa values larger than 6, no values were calculated because the uncertainty
is too great. When a Kx value was needed for a complex ion with successive ionization
constants, the first ionization constant (pKj) was used in the computation of the Kx value.
All ionization constants were computed with SPARC29.
Estimated data
Most of the log values in Table 1 were computed with QSAR4 and SPARC29. QSAR is an
interactive chemical database and hazardous assessment system designed to provide basic
information for the evaluation of the fate and effects of chemicals in the environment. The
QSAR4 system is a composite of databases containing measured values obtained from the
literature and a state-of-the-art QSAR model library capable of estimating chemical
properties, behavior, and toxicity, based on conventional estimation techniques, many of
which were derived from the work of Lyman et al.50 The QSAR system contains automated
estimation routines for 13 properties based upon modified structure-activity correlations.
SPARC29 is a computational expert system that predicts chemical reactivity. The system has
the capability of crossing chemical boundaries to cover all organic chemicals and uses
algorithms based on fundamental chemical structure theory to estimate parameters. SPARC
quantifies reactivity by classifying molecular structures and selecting appropriate
"mechanistic" models. It uses an approach that combines principles of quantitative structure-
activity relationships, linear free energy theory (LFET), and perturbed molecular orbital
(PMO) or quantum chemistry theory. In general, SPARC utilizes LFET to compute thermal
properties and PMO theory to describe quantum effects such sb delocalization energies or
polarizabilities of n electrons.
For example, SPARC computes the log of the octanol-water partition coefficient from activity
coefficients in the octanol (y~) and water (y~ ) phases:
-------
14
Fate Constants for Hazardous Waste Identification
Y» M„
kg Kow = lo8 — + kg TT- (12)
where M0 and Mw are solvent molecularities of octanol and water, respectively. Activity
coefficients for either solvent or solute are computed by solvation models that are built from
structural constituents requiring no data besides the structures.
A goal for SPARC is to compute log values that are as accurate as values obtained
experimentally for a fraction of the cost required to measure them. Because SPARC does not
depend on laboratory measurements conducted on compounds with structures closely related
to that of the solute of interest, it does not have the inherent problems of phase separation
encountered in measuring highly hydrophobic compounds (log > 5). For these compounds,
SPARC'S computed value should, therefore, be more reliable than a measured one.
Redox
Abiotic Redox Transformations of Organic Compounds
Abiotic redox reactions will not generally mineralize large organic molecules, but the transfor-
mations will result in daughter products with different chemical and physical properties61.
Furthermore, abiotic transformations can convert bio-resistant compounds to more bio-
susceptible compounds. For example, redox reactions can result in oxidation or reduction of
key functional groups on molecules that will render them labile to microbial transformations
and ultimately mineralization or conversion to other environmentally innocuous components.
A large number of functional groups on organic compounds have been shown to undergo
abiotic reduction under ambient environmental conditions. In general, these redox transfor-
mations encompass almost all chemical functional groups, utilize a large number of organic
and inorganic redox agents, and result in an almost unlimited number of products82.
Furthermore, the rates of redox reactions can be expected to span many orders of magnitude,
depending upon the reaction type and redox agents' activities. Unfortunately, only a few of
the reactions have been studied in enough detail to identify the system redox agents and
provide kinetics data.
It is not currently possible to address redox transformations for all the listed compounds in
soils, sediments and aquifer systems because of a lack of quantitative research in the area
of environmental redox reactions. For the few classes of compounds where detailed studies
have been carried out, it is possible to obtain reductive rate constants and apply them to
environmental systems53,84. In these detailed studies, kinetic expressions and the reducing
agents have been identified.
In this report, reduction of halogenated hydrocarbons and nitroaromatics, and the autooxida-
tion of aldehydes and amines are addressed. Estimated rate constants for halogenated
hydrocarbons and nitroaromatics are given in Table 2. These rate constants were computed
for soil-water systems in which the solids contained 1% and 0.02% organic carbon. The data
-------
Parti 15
clearly indicate the dependence of the reductive process on organic carbon. A 50-fold increase
in organic carbon from a concentration of 0.02% decreases the half-lives by about 4 orders of
magnitude for the halogenated hydrocarbons and about 1 order of magnitude for the
nitroaromatics. For the QSAR computations of the halogenated hydrocarbons, either
published sigma constants or estimated values were used. For the QSAR computations of
the nitroaromatics, published sigma constants were used except for parathion and methyl
parathion. For these two compounds, the sigma constants were estimated from 1-methoxy-p-
nitrobenzene. Rate constants for the nitroso compounds were not computed. However,
preliminary laboratory studies of some nitroso compounds indicated half-lives of less than 1
hour. It was not possible to identify products of degradation. We hope that the following will
give the reader some insight into this difficult and unexplored area of heterogeneous redox
reactions.
Convention of Writing Redox Reactions
In the environmental literature, as well as in organic chemistry textbooks, the definitions of
oxidation-reduction are often empirical and can result in ambiguities, especially when applied
across classes of compounds62. Reactions that form new bonds with hydrogen are often
referred to as reduction, whereas those forming new bonds with oxygen are often referred to
as oxidation. Although this system may hold for specific classes of compounds, it is not
generally applicable to the myriad of chemicals of environmental importance.
The overall reaction is not given because, for the most part, the activity of the reducing or
oxidizing agent responsible for the transformation is not known. Thus it is not possible to
sum up the two half-reactions and write the overall equation.
An unambiguous method for describing redox processes is to write the chemical equation for
each half-reaction with the reactants on the left and the products on the right, balancing the
equation by using hydrogen ions to provide needed hydrogen and hydroxide ions or water
molecules to provide needed oxygen atoms. Electrons are then added to balance the charge
(Figure 1). If electrons are added to the left side of the equation, it is a reduction reaction.
If electrons are added to the right side of the equation, it is an oxidation reaction. Examples
of half-reactions for reduction and oxidation are given below.
Reduction
Figure 1 shows two examples of reductive transformations. The first is a two-electron
transfer reaction for the reduction of 1,2-dichloroethane to ethene and chloride. The second
is a six-electron reduction of nitrobenzene, requiring six protons that gives aniline and water
as products.
-------
16
Fate Constants for Hazardous Waste Identification
H + 26 *" + 2 CI"
Figure 1.
Half-reactions for the reduction of 1,2-dichloroethane to
ethene and the reduction of nitrobenzene to aniline.
Oxidation
Figure 2 shows two examples of redox half-reactions. The first is a two-electron oxidation of
1,1,2-trichloroethylene to 1,1-dichloroacetic acid, chloride, and three protons. The second is
a two-electron oxidation of benzaldehyde to benzoic acid. In this reaction, water provides the
source of oxygen and results in two protons as a product.
CI^^CHCI + 2 H2O * C^HCC02H + Q|- + 3 + 2e~
Figure 2. Half-reactions for the oxidation of 1,1,2-trichloro-
ethylene to 1,1-dichloroacetic acid and the oxidation
of benzaldehyde to benzoic acid.
Descriptions of Redox State of the System
Eh
When the Eh of the heterogenous system, as measured by a platinum electrode, is above Eh
50 mv (relative to Ag:AgCl), the reductive reaction does not occur for the halogenated
-------
Parti 17
hydrocarbons and nitroaromatics88. When the Eh of the system is below 50 mv, the reaction
occurs and the rate of reaction is independent of the magnitude of the Eh.
pH
In general, in heterogenous systems, pH effects on the rates of abiotic reductions are
minimal. This is partly because the solids tend to buffer the pH of the system56. For
example, over the pH range of 5 to 9, the rate constant for reduction of nitrobenzene to
aniline was independent of pH. The same has been observed for the reduction of halogenated
hydrocarbons.
Kinetics of Reaction in Heterogenous Systems
To carry out abiotic reactions in heterogenous systems such as soils, sediments and aquifer
materials, requires an understanding of the kinetics of reaction. In these heterogenous
systems, sorption of the compounds to the solids will affect the overall kinetics of reaction.
A working model has been proposed to account for the observed kinetics of reduction of
compounds in these types of heterogenous systems54'65'86,58. The model, which is shown below,
assumes non-reactive and reactive sorptive sites on the solids.
P+S
ki
P:S
k-1
Where P is pollutant concentration; S is sediment concentration (g/g); k1 and k_2 are the
respective sorption-desorption rate constants to a non-reactive sink, P:S; k2 and k_2 are the
respective sorption-desorption rate constants to the reactive sink, P:R; kr is the first-order
rate constant for reduction at reactive solid sites.
Calculation of Rate Constants
Reductive Processes
Nitroaromatics
Rate constants for the reduction of nitroaromatics can be calculated using the SAR based on
Hammett sigma constants reported by Wolfe et al.66 This relation provides selected, observed
first-order disappearance rate constants for nitroaromatic compounds. These first-order rate
constants have been shown by Wolfe et al.56 to correlate with the organic carbon of the
system.
Halogenated hydrocarbons
Wolfe and co-workers57,88 developed a structure reactivity relationship that associates the
reductive disappearance rate constants of halogenated hydrocarbons in anoxic sediments with
readily available molecular descriptors. The correlation is based on disappearance rate
constants for the reductive transformation of 19 halogenated hydrocarbons. The compounds
-------
18
Fate Constants for Hazardous Waste Identification
span a large cross section of chemical structures that includes halogenated methaneB,
ethanes, ethenes, and halogenated aromatics.
Wolfe and co-workers57,68 also corrected the rate constants for hexachloroethane for sorption.
These rate constants were obtained in 18 different sediment, soil and aquifer samples and
correlated with the organic carbon.
Oxidative Processes
Aldehydes
In general, aldehydes will undergo autooxidation to the corresponding carboxylic acids in the
presence of oxygen62,69. In sediments, soil and aquifer materials, aldehydes have been shown
to undergo such oxidations even under anoxic conditions. No comprehensive data base of rate
constants is available for these reactions and, furthermore, the autooxidation kinetics are too
complex to extrapolate precise rate constants from laboratory to field conditions.
These reactions have been observed for a large number of aldehydes and, based on this
qualitative data base, half-lives of less than 1 year are reasonable.
Amines
In general, amines undergo rapid autooxidation62,89. Their autooxidation mechanisms and
transformation kinetics are complicated and not well understood. In the presence of oxygen
in sediments and soils, they can form covalent bonds with the organic components of the
solids and thus become bound residues. Under anoxic conditions in sediments and soils,
however, they appear to be stable for long periods of time and tend not to bind irreversibly
to the organic matter associated with the organic carbon.
No comprehensive data base of rate constants for these types of reactions has been compiled
and, furthermore, the reaction kinetics are too complex to extrapolate precise rate constants
from the laboratory to field conditions.
Because reactions have been observed for a large number of amines, it is reasonable to
assume that these compounds will undergo autooxidation in the field. Based on the qualita-
tive data base, half-lives for this class of compounds will be less than 1 year.
-------
TABLE 1. Chemical hydrolysis rate constants and sorption data for organic compounds.
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
k.
K
K
References
Common Name
No.
Log Koc
Log K„.
MY
r1
MV
Comment
K^/Kc/kb
1. Acenaphthene
83-32-9
3.75
4.07
0
0
0
NHFG
/ 4/ 0
2. Acetone (2-propanone)
67-64-1
-0.588
-0.268
0
0
0
NHFG
/ 4/ 0
3. Acetonitrile (methyl cyanide)
75-05-8
-0.714
-0.394
0
0
45
RATE
/ 4/ 24
Acetamide
60-35-5
-1.55
-1.23
2.6E2
0
1.5E3
/ 4/ 5
Acetic acid
64-19-7
-2.23
-0.234
0
0
0
NHFG
/ 4/ 0
(pK.-4.65)
Ammonia
7664-41-7
NA
NA
0
0
0
NHFG
/ 0/ 0
4. Acetophenone
98-86-2
1.26
1.58
0
0
0
NHFG
/ 4/ 0
5. Acrolein
107-02-8
-0.219
0.101
NG
6.68E8
NG
/ 4/ 30
3-Hydroxy-1 -propanal
2134-29-4
-1.3
-1.0
0
0
0
NHFG
o
o>
CM
6. Acrylarride
79-06-1
-0.989
-0.669
31.5
1.8E-2
0
a
/ 4/ 6
Acrylic acid
79-10-7
-1.84
0.161
0
0
0
NHFG
/ 4/ 2
(pK.-4.13)
Ammonia
7664-41-7
NA
NA
0
0
0
NHFG
1 01 o
7. Acrylonitriie
107-13-1
-0.089
0.231
5E2
0
5.2E3
RATE
/ 4/ 6
Acryiamide **
79-06-1
-0.989
-0.669
31.5
1.8E-2
0
a
/ 4/ 6
Acrylic acid
79-10-7
-1.84
0.161
0
0
0
NHFG
/ 4/ 2
(pK.-4.13)
Ammonia
7664-41-7
NA
NA
0
0
0
NHFG
1 01 o
8. Aidrin
309-00-2
6.18
6.496
0
0
0
NLFG
/ 7/ 0
9. Aniline
62-53-3
0.595
0.915
0
0
0
NHFG
/ 4/ 0
(benzeneamine: pK,,-9.3)
-------
to
o
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
LogK^
Chemical Hydrolysis
k. K, K.
nrV r' m'y'
Comment
References
KclK^IK
10. Antimony (and compounds N.O.S.)
11. Aramite
140-57-8
5.2
5.5
0
7.7
6.0E4
ff
1 29/
1 -Methyl-2-{p-(l ,1-dimethyl-
ethy))phenoxy)ethylhydrogen8ulfite
1 -Methyl-2[p-(l ,1 -dimethyl-
ethyl)phenoxy]ethanol
Sulfuric acid
1 -Methyl-2[p-(l ,1 -dimethylethyl)-
phenoxyjethanol
2-Chloroethylhydrogen8ulfite
Sulfuric acid
2-Chloroethanol
Hydrochloric acid
Ethylene oxide
Ethylene glycol
2-Chloroethanol
Hydrochloric acid
Ethylene oxide
Ethylene glycol
NG
2416-30-0
7664-93-9
2416-30-0
NG
7664-93-9
107-07-3
7647-01-0
75-21-8
107-21-1
107-07-3
7647-01-0
75-21-8
107-21-1
3.15
NA
3.15
NA
-0.492
NA
-1.1
-1.5
-0.492
NA
-1.1
-1.5
3.47
NA
3.47
NA
-0.172
NA
-0.792
-1.2
-0.172
NA
-0.792
-1.2
0
0
0
0
0
0
0
0
2.9E5
0
0
0
2.9E5
0
7.7
0
0
0
7.7
6.0E40
3.9E-2
0
21
0
3.9E-2
0
21
0
6.0E4
0
0
0
6.0E4
0
3.2E5
0
0
0
3.2E5
0
0
0
gg
NLFG
NHFG
NLFG
gg
NHFG
NHFG
NHFG
NHFG
NHFG
/ / 0
/ 4/ 0
/ 0/ 0
/ 4/ 0
/ / o
/ 01 0
/ 4/ 3
/ 0/ 0
/ 4/ 5
1 291 0
1 4/ 3
/ 0/ 0
/ 4/ 5
/ 29/ 0
12. Arsenic (and compounds N .O.S.)
7440-38-2
13. Barium {and compounds N.O.S.)
7440-39-3
14. Benz[a]anthracene
56-55-3
5.34
5.66
0
0
0
NHFG
/ 4/ 0
15. Benzene
71-43-2
1.80
2.12
0
0
0
NHFG
/ 37/ 0
16. Benzidine
(pKt-9-3)
92-87-5
1.26
1.58
0
0
0
NHFG
/ 4/ 0
17. Benzo[&]fluoranthene
205-99-2
5.8
6.12
0
0
0
NHFG
/ 4/ 0
18. Benzo[a]pyrene
50-32-8
5.8
6.12
0
0
0
NHFG
/ 4/ 0
J
&
in
53"
(7?
I
Q)
I
§
I
a
CD
3
g*
?
Q)
O'
3
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
K
References
Common Name
No.
LogK„
Log K„
M'Y"1
V1
M'V1
Comment
Koc/K^/kn
19. Benzotrichloride
98-07-7
4.06
4.38
0
2.0E6
0
/ 29/ 5
Benzoic acid
65-85-0
-0.11
1.89
0
0
0
NHFG
/ 4/ 0
(pK.-4.18)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
20. Benzyl alcohol
100-51-6
0.78
1.10
0
0
0
NHFG
/ 4/ 0
(PK.-15.1)
21. Benzyl chloride
100-44-7
2.84
3.16
0
4.1 E2
0
RATE
/ 29/24
Benzyl alcohol **
100-51-6
0.78
1.10
0
0
0
NHFG
/ 4/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
22. Beryllium {and compounds N.Q.S.)
7440-41*7
23. S/s(2-chloroethyl)ether
111-44-4
0.80
1.12
0
0.23
0
/ 1/ 3
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 o
2-(2-chloroethoxy)ethanol
628-89-7
-0.186
-0.154
0
0.28
0
/ 4/ 3
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
S/s(2-hydroxyethyi)ether
111-46-6
-1.62
-1.30
0
0
0
NHFG
/ 4/ 2
1,4-Dioxane **
123-91-1
-0.812
-0.492
0
0
0
NHFG
/ 4/ 2
24. 8/s(2-chloroiaopropyi)ether
39638-32-9
2.39
2.71
0
0
See Part II.
/ 4/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 01 0
(2-Hydroxyi8opropyl-2-chloro-
NG
2.7
3.0
b
1 29/ 0
isopropyl)ether
S/s(2-hydroxyi8opropyl)
72986-46-0
1.1
1.4
0
0
0
NHFG
1 29/ 0
ether
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 o
-------
ro
ro
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
Log
Log K„
M-'r'
Y"1
M'Y1
Comment
Kcli^lK
25. 8/s(2-ethylhexyl)phthalate
117-81-7
7.13
7.453
0
0
1.4E3
RATE
1 71 9
2-E1hylhexanol
104-76-7
2.56
2.88
0
0
0
NHFG
/ 29/ 0
2-Ethylhexyl hydrogen phthalate
4376-20-9
5.5
5.8
0
0
7E2
c
/ 29/ 0
2-Ethylhexanol
104-76-7
2.56
2.88
0
0
0
NHFG
/ 29/ 0
o-Phthalic acid
88-99-3
-1.27
0.732
0
0
0
NHFG
/ 4/ 0
(pK.-3.03)
26. Bromodichloromelhane
75-27-4
1.77
2.09
NG
NG
5.0E4
t
/ 4/ 41
Carbon monoxide
630-08-0
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
1 01 o
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
27. Bromomethane
74-83-9
0.76
1.08
0
9.46
0
/ 4/ 10
(Flammable gas, bp-4°C)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
/ 0/ 0
28. Butanol
71-36-3
0.503
0.823
0
0
0
NHFG
/ 4/ 0
29. Butyl benzyl phthalate
85-68-7
4.23
5.05
0
0
1.2E5
d
11 / 29/ 0
Benzyl alcohol **
100-51-6
0.78
1.10
0
0
0
NHFG
/ 4/ 0
Butyl hydrogen phthalate
131-70-4
3.43
3.75
0
0
6E4
c
/ 9/ 0
o-Phthalic acid
88-99-3
-1.27
0.732
0
0
0
NHFG
/ 4/ 0
(pK.-3.03)
n-Butanol **
71-36-3
0.503
0.823
0
0
0
NHFG
/ 4/ 0
n-Butanol **
71-36-3
0.503
0.823
0
0
0
NHFG
/ 4/ 0
Benzyl hydrogen phthalate
2528-16-7
3.63
3.95
0
0
6E4
c
/ 29/ 0
Benzyl alcohol **
100-51-6
0.78
1.10
0
0
0
NHFG
/ 4/ 0
o-Phthalic acid
88-99-3
-1.27
0.732
0
0
0
NHFG
/ 4/ 0
(pK.-3.03)
30. 2-sec-Butyl-4,6-dinitrophenol
88-85-7
2.02
4.02
0
0
0
NHFG
/ 4/ 0
(Dinoseb: pK.-3.5)
31. Cadmium (and compounds N.O.S.)
7440-43-9
2?
&
3"
55"
|
&}
I
s
a>
(0
Q.
a>
I
&)
o'
3
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log K„.
Chemical Hydrolysis
K K
irY1 r1 mY1
Comment
References
Koc/K^/k,
32. Carbon disulfide
75-15-0
1.84
2.16
0
0
3.15E4
/ 1/ 61
Carbonyl sulfide
Carbon dioxide
Hydrogen sulfide
(Flammable gas: bp- -60°C;
(PK.-7.0)
463-58-1
124-38-9
7783-06-4
0.4
NA
NA
0.7
NA
NA
NG
0
0
6.3E2
0
0
4.1 E8
0
0
NHFG
NHFG
/ 29/ 40
/ 0/ 0
1 01 o
33. Carbon tetrachloride
56-23-5
2.41
2.73
0
1.7E-2
0
RATE
/ 37/13
Carbon dioxide
Hydrochloric acid
124-38-9
7647-01-0
NA
NA
NA
NA
0
0
0
0
0
0
NHFG
NHFG
/ 0/ 0
/ 0/ 0
34. Chlordane
57-74-9
5.89
6.21
0
0
37.7
y
/ 62/ 3
2,4,5,6,7,8,8-Heptachtoro-
3a,4,7,7a-tetrahydro-4,7-
methano-1 H-indene
5103-65-1
6.2
6.5
0
0
0
NLFG
1 29/ 2
35. p-Chloroaniline
(pKb~10)
106-47-8
1.61
1.93
0
0
0
NLFG
1 4/ 0
36. Chlorobenzene
108-90-7
2.578
2.898
0
0
0
NLFG
/ 7/ 1
37. Chlorobenzilate
(PK.-13.6)
510-15-6
4.04
4.36
0
0
2.8E6
ff
/ 4/
0/s(p-chlorophenyl)hydroxy-
acetic acid (pK.-3.l)
p.p'-Dichlorobenzophenone
Ethanol
23851-46-9
90-98-2
64-17-5
2.5
4.43
-0.62
4.5
4.75
-0.30
0
0
0
0
0
0
2.8E5
0
0
ff
NLFG
NHFG
/ 29/ 0
1 4/ 0
/ 29/ 0
38. 2-Chloro-l ,3-butadiene
(Chloroprene)
126-99-8
1.74
2.06
0
0
0
NLFG
/ 4/ 0
-------
ro
4*
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log K„.
Chemical Hydrolysis
K K
Nr'r' r1 M'V
Comment
References
Koc/K^/k,,
39. Chlorodibromomethane
124-48-1
1.91
2.23
NG
NG
2.5E4
t
/ 4/ 41
Carton monoxide
Hydrobromic acid
Hydrochloric acid
630-08-0
10035-10-6
7647-01-0
NA
NA
NA
NA
NA
NA
0
0
0
0
0
0
0
0
0
NHFG
NHFG
NHFG
1 01 o
/ 0/ 0
1 01 o
40. Chloroform
67-66-3
1.58
1.90
0
1.0E-4
2.74E3
1 37/13
Carbon monoxide
Hydrochloric acid
630-08-0
7647-01-0
NA
NA
NA
NA
0
0
0
0
0
0
NHFG
NHFG
/ 0/ 0
1 01 o
41. Chloromethane
(Methyl Chloride: bp- -23.7°C)
74-87-3
42. 2-Chloropheno!
(PK.-8.4)
95-57-8
1.82
2.20
0
0
0
NLFG
1 4/ 0
43. 3-Chloropropene
107-05-1
1.13
1.45
0
40
0
/ 4/ 5
3-Hydroxypropene
Hydrochloric acid
107-18-6
7647-01-0
-0.57
NA
-0.250
NA
0
0
0
0
0
0
NHFG
NHFG
/ 4/ 0
/ 0/ 0
44. Chromium (and compounds N.O.S.)
45. Chrysene
218-01-9
5.34
5.66
0
0
0
NHFG
/ 4/ 0
46. Cresols (See below)
47. o-Cre8ol
(PK.-9.8)
95-48-7
1.76
2.12
0
0
0
NHFG
/ 4/ 1
48. m-Cresol
(PK.-10.0)
108-39-4
1.76
2.12
0
0
0
NHFG
/ 4/ 1
49. p-Cre80l
(PK.-10.1)
106-44-5
1.76
2.12
0
0
0
NHFG
/ 4/ 1
50. Cumene
98-82-8
3.40
3.72
0
0
0
NHFG
/ 4/ 0
21
&
3
ST
CO
I
&)
I
s
I
Co
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
k.
K
K
References
Common Name
No.
Logt^
Log K„.
MV
r'
M-V1
Comment
Koc/Ko./k,
51. Cyanide (amenable)
57-12-5
0
29
0
e
/ / 27
Carbon dioxide
124-38-9
NA
NA
0
0
0
NHFG
/ 0/ 0
Ammonia
7664-41-7
NA
NA
0
0
0
NHFG
/ 0/ 0
52. 2,4-Dlchlorophenoxyacetic acid
94-75-7
0.68
2.68
0
0
0
NLFG
/ 4/ 1
(2,4-D: PK.-3.1)
53. DDD
72-54-8
5.89
6.21
0
2.5E-2
2.2E4
RATE
/ 4/ 24
2,2-B/s(4-chlorophenyl)-1-
1022-22-6
6.47
6.79
0
0
0
NLFG
1 29/ 0
chloroethene
(DDMU)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 o
54. DDE
72-55-9
6.64
6.956
0
0
0
NLFG
/ 7/ 12
55. p,p'-DDT
50-29-3
6.59
6.91
0
6.0E-2
3.1 E5
/ 4/ 12
DDE **
72-55-9
6.64
6.956
0
0
0
NLFG
/ 7/ 12
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
56. Diallate
2303-16-4
4.17
4.49
0
0.10
8E3
1 621 3
Diallate (Z-)
17708-57-5
3.8
4.1
0
3.2E-1
0
RATE
1 29/24
Diallate (£-)
17708-58-6
3.8
4.1
0
7.8E-2
7.3E3
RATE
/ 29/24
Dii8opropylarrine
108-18-9
0.84
1.16
0
0
0
NHFG
/ 4/ 0
(PK<,-11.5)
frans-2,3-Dichloro-2-propene-1 -
16714-72-0
2.4
2.84
0
0
0
NLFG
1 291 0
thiol
(PK.-8.2)
c/s-2,3-Dichloro-2-propene-1 -
16714-71-9
2.5
3.0
0
0
0
NLFG
1 29/ 0
thiol
*
"l
00
£2
Carbon dioxide
124-38-9
NA
NA
0
0
0
NHFG
/ 0/ 0
57. Dibenz(a,/7]anthracene
53-70-3
6.52
6.84
0
0
0
NHFG
/ 4/ 0
-------
Fate Constants for Hazardous Waste Identification
8^
• X
/ 4/ 31
/ 0/ 0
/ 4/ 0
/ 0/ 0
/ 4/ 5
/ 29/ 0
/ 29/ 5
/ 29/ 0
/ 0/ 0
/ 29/ 0
/ 0/ 0
/ 29/ 0
/ 0/ 0
/ 29/41
/ 4/ 0
/ 29/ 5
/ 29/ 0
/ 0/ 0
/ 29/ 0
I 01 0
/ 29/31
/ 0/ 0
/ 4/ 31
1 29/ 0
I 01 0
/ 0/ 0
/ 4/ 0
1 lie 1
Comment
RATE
NHFG
CC
NHFG
f
NHFG
NHFG
NHFG
NHFG
cc
NHFG
cc
NHFG
NHFG
NHFG
NHFG
NHFG
NLFG
NHFG
NHFG
NLFG.w
NLFG
V
CO
>
e
i
CO
0
1
¦C
O
V
*5
in 10 in in in
LLJ LU LU III LLI
oj 0 0 0 © 0 000 o3oo3 0 000 OOOOOOO
1- in 1- in in
O
O
4.0E-3
0
1.4
0
30.9
0.46
8.9
0
0
0
0
1.4
0
1.6E1
1.4
8.9
0
0
0
0
29
0
1.8
0
0
0
O
O
O OOoSjo m OOO ooojjjo fij OOO OOOOOOO
cvj K r- rs!
O
O
Sorption
Log K^,
2.26
NA
0.49
NA
-0.210
-0.5
-1.4
-1.9
NA
-1.9
NA
1.42
NA
0.5
-0.857
-1.4
-1.9
NA
-1.9
NA
2.71
NA
2.07
1.72
NA
NA
1.53
3.40
Sorption
Log
1.94
NA
0.17
NA
-0.53
-0.8
-1.7
-2.2
NA
-2.2
NA
1.10
NA
0.2
-1.2
-1.7
-2.2
NA
-2.2
NA
2.39
NA
1.75
1.40
NA
NA
1.21
3.08
1
Chemical
Abstract
Service
No.
96-12-8
10035-10-6
73727-39-6
10035-10-6
106-89-8
96-24-2
556-52-5
56-81-5
7647-01-0
56-81-5
7647-01-0
96-13-9
10035-10-6
3132-64-7
4704-77-2
556-52-5
56-81-5
10035-10-6
56-81-5
7647-01-0
513-31-5
10035-10-6
16400-63-8
598-19-6
10035-10-6
7647-01-0
74-95-3
95-50-1
Common Name
58.1,2-Dibromo-3-chloropropane
OO
Hydrobromic acid
2-Bromo-3-ctiloropropanol
Hydrobromic acid
Epichlorohydrin
1 -Chloro-2,3-dihydroxy-
propane
1 -Hydroxy-2,3-
propylene oxide
Glycerol
Hydrochloric acid
Glycerol
00
Hydrochloric acid
2,3-Dibromo-l -propanol
Hydrobromic acid
Epibromohydrin
1 -Bromo-2,3-
dihydroxypropane
1 -Hydroxy-2,3-
propylene oxide
Glycerol
Hydrobromic acid
Glycerol
OO
Hydrochloric acid
2,3-Dibromopropene
Hydrobromic acid
2-Bromo-3-chloropropene
2-Bromo-3-hydroxypropene
Hydrobromic acid
Hydrochloric acid
59. Dibromomethane (methylene bromide)
a>
c
s
c
©
f
0
c
0
0
1
CO
0
(0
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K.
K
References
Common Name
No.
Log Kx
LogK^
M-'Y"
Y"1
Air'Y'1
Comment
Koc/K^/k,
61.1,4-Dichtorobenzene
106-46-7
3.05
3.37
0
0
0
NLFG
/ 37/ 1
62. 3,3'-Dichlorobenzidine
91-94-1
3.32
3.64
0
0
0
NLFG
/ 4/ 0
(pKb-11.7)
63. Dichlorodifluoromethane
75-71-8
(Freon 12: bp - -29°C)
64.1,1 -Dichioroethane
75-34-3
1.46
1.78
0
1.13E-2
3.78E-1
RATE
/ 4/ 13
Acetaldehyde
75-07-0
-0.544
-0.224
0
0
0
NHFG
/ 4/ 0
(bp - 20°C)
Vinyl chloride
75-01-4
1.04
1.36
0
0
0
NLFG
/ 1/ 0
(bp - -13.37°C)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
65.1,2-Dichloroethane
107-06-2
1.13
1.45
0
9.61 E-3
54.7
/ 37/13
Vinyl chloride
75-01-4
1.04
1.36
0
0
0
NLFG
/ 1/ 0
(bp - -13.37°C)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 0
2-Chloroethanol
107-07-3
-0.492
-0.172
0
3.9E-2
3.2E5
/ 4/ 3
Ethylene oxide
75-21-8
-1.1
-0.792
2.9E5
21
0
/ 4/ 5
Ethylene glycol
107-21-1
-1.52
-12
0
0
0
NHFG
/ 29/ 2
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 0
66.1,1-Dichloroethylene
75-35-4
1.79
2.11
0
0
0
NLFG
/ 1/ 2
(Vinylidene chloride: bp - 30-32°C)
67. cis-1,2-Dichloroethylene
156-59-2
1.7
2.0
0
0
0
NLFG
1 29/ 0
68. trans-1,2-Dichloroethylene
156-60-5
1.60
1.92
0
0
0
NLFG
1 29/ 0
69. Dichloromethane
75-09-2
0.93
1.25
0
1E-3
6E-1
aa
/ 4/ 63
(Methylene Chloride)
Formaldehyde
50-00-0
-1.3
-1.0
0
0
0
NHFG
1 291 0
(bp- -19.5°C; HYDRATES RAPIDLY)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 o
3
ro
-------
Fate Constants for Hazardous Waste Identification
8^
R
o
CM
O O O O W o
g]og]o*«
O) O) 1
CM CM 1
o
o o
Oi Q
O)
0)
CM
CM °
CM
CM
•
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•
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S
<
en
u o o
u. U- _ U-
_i x x
z z z
o
o (D no
<
cr
2
o
11-
OJ
«5
>.
9
*
z
TB
it
>
jf*-
S-
CM
m ^
tu CO
OOfflOUiO
oo
o o o o o o
CM
UJ
_ - o f"- <©
q < S < cm o
^ iz9v
CM
CM g < CM g <
CM ^ Z CM ^ Z
§
id
in
CO
m
CO
g*?
Is
o>
CM
h-
9
CD
N
in
8
£
CO
o
xf
h-
(O
in
©
sz
Q.
B
o
9 V
* *
CM Q.
o
©
5
Q.
s
Q.
e
o
XT
o
b
CM
Q.
2
Q.
= £
© O «||
isv*§1
| 8 i o ® "9
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iz &f 8"
O 8 Sx Ql
•c -H «C
9 1-9
r- I CM
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i
•! i 1
~ § 2 B S
V J ® J ®
.{ft N CD fc «
O (O GO ^ W
CO
* in
R Is* .
i «•§
8 "i =
ag*
© * *
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o *7 o 13
O >S £
O X ® £
" s. S "o.
j. |*S a
CT. S -S Od
«?2
>¦? Sil
' T w * ©
s co E ~
¦fc (O CO 73 S.
I
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log K..
Sorption
Log K„,
Chemical Hydrolysis
K K
MV r1 M"1Y'1
Comment
References
Koc/K^/k,
74. Diethyl phthaiate
84-66-2
1.99
2.57
0
0
3.1 E5
RATE
11/ 4/ 9
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFQ
1 291 0
Ethyl hydrogen phthaiate
2306-33-4
2.18
2.50
0
0
1.6E5
c
1 29/ 0
o-Phthalic acid
88-99-3
-1.27
0.732
0
0
0
NHFG
/ 4/ 0
(pK.-3.03)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
75. Diethylstilbestrol
(PK.-9.3)
56-53-1
4.09
4.96
0
0
0
NHFG
/ 4/ 0
-------
(a)
O
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
Log
Log
irV'
Y"'
M'Y'
Comment
KclK~IK
76. Dimethoate
60-51-5
0.132
0.452
0
1.68
4.48E6
RATE
1 4/ 32
(K, at C)
O.O-Dimethylphosphorodithioic acid
756-80-9
-2.5
-0.5
0
0.2
0
z
1 29/ 0
(PK.-1.6)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFQ
1 4/ 0
O-Methylphosphorodithioic acid
106191-34-8
-0.7
1.3
0
1
0
z
1 29/ 0
(PK.-1.5)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
1 4/ 0
Phoaphorodithioic acid (pK„-1.7)
15834-33-0
-3.6
-1.6
0
3
0
bb
/ 29/64
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 01 o
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 0/ 0
W-Methyl-2-hydroxyacetamide
5415-94-1
-0.8
-0.5
0
0
0
NLFG
/ 29/ 0
(K, at P)
OMethyl-S-[2-(/V-methylacetamide)]-
2700-77-8
-0.5
1.5
0
0.2
0
/ 29/ 0
phosphorodithioic acid (pK,-l .6)
W-Methyl-2-hydroxyacetamide
5415-94-1
-0.8
-0.5
0
0
0
NLFG
/ 29/ 0
O-Methylphosphorodithloic acid
106191-34-S
-0.7
1.3
0
1
0
z
/ 29/ 0
(PK.-1.5)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
Phosphorodithioic acid
15834-33-0
-3.6
-1.6
0
3
0
bb
/ 29/ 64
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 4/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 01 o
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
00
0,0-Dimethylpho8phorothioic acid
1112-38-5
-3
-1
0
0.2
0
z
1 29/ 0
(PK.-1.6)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
1 41 0
O-Methylphosphorothioic acid
1111-99-5
-4
-2.0
0
1
0
z
/ 29/ 0
(PK.-1.5)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 01 o
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 01 o
W-Methyl-2-mercaptoacetamide (pK,«8.7)
20938-74-3
-0.8
-1.0
0
0
0
NLFG
/ 29/ 0
J
8
3
S"
CO
§•
£
(/)
CD
I
3
?
Q)
o*
3
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log K„.
Chemical Hydrolysis
k. K K,
mV r1 M'Y1
Comment
References
K0c/K0./kh
77. 3,3'-Dimethoxybenzidine
(pKb-10.3)
119-90-4
1.49
1.81
0
0
0
NHFG
/ 4/ 0
78. 7,12-Dimethylbenz(a]anthracene
57-97-6
6.64
6.96
0
0
0
NHFG
/ 4/ 0
79. 3,3'-Dimethylbenzidine
(pKt-9.3)
119-93-7
2.55
2.87
0
0
0
NHFG
/ 4/ 0
80. 2,4-Dlmethylphenol
(PK.-10.1)
105-67-9
2.29
2.77
0
0
0
NHFG
/ 4/ 0
81. Dimethyl phthalate
131-11-3
1.20
1.52
0
0
1.8E6
RATE
/ 4/ 9
Methanol **
Methyl hydrogen phthalate
Methanol **
o-Phthallc acid (pk.-3.03)
67-56-1
4367-18-5
67-56-1
88-99-3
-1.08
1.6
-1.08
-1.27
-0.764
1.9
-0.764
0.732
0
0
0
0
0
0
0
0
0
9E5
0
0
NHFG
c
NHFG
NHFG
/ 4/ 0
1 29/ 0
1 4/ 0
/ 4/ 0
82.1,3-Dlnitrabenzene
99-65-0
1.31
1.63
0
0
0
NHFG
/ 4/ 0
83. 2,4-Dinitrophenol
(PK.-3.3)
51-28-5
•0.09
1.91
0
0
0
NHFG
/ 4/ 0
84. 2,4-Dinitrotoluene
121-14-2
1.68
2.00
0
0
0
NHFG
/ 4/ 1
85. 2,6-DMtrotoluene
606-20-2
1.40
1.72
0
0
0
NHFG
/ 4/ 0
86. Di-n-butyl phthalate
84-74-2
4.37
4.69
0
0
1.2E5
RATE
/ 4/ 9
n-Butanol **
n-Butyl hydrogen phthalate
n-Butanol"
o-Phthalic acid
(PK.- 3.03)
71-36-3
131-70-4
71-36-3
88-99-3
0.503
3.43
0.503
-1.27
0.832
3.75
0.823
0.732
0
0
0
0
0
0
0
0
0
6E4
0
0
NHFG
c
NHFG
NHFG
/ 4/ 0
/ 29/ 0
/ 4/ 0
/ 4/ 0
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log Kk
Sorption
Log K,,.
Chemical Hydrolysis
K K K
M'r1 r1 m'y1
Comment
References
Koc/K^/k*
87. Di-n-octyl phthalate
117-84-0
7.6
7.9
0
0
5.2E5
RATE
/ 29/15
n-Oclanol
n-Oclyl hydrogen phthalate
n-Octanol
o-Phthalic acid
(pK.- 3.03)
111-87-5
5393-19-1
111-87-5
88-99-3
2.77
5.8
2.77
-1.27
3.09
6.1
3.09
0.732
0
0
0
0
0
0
0
0
0
2.6E5
0
0
NHFG
c
NHFG
NHFG
/ 29/ 0
1 29/ 0
/ 29/ 0
/ 4/ 0
88.1,4-Dioxane
123-91-1
-0.812
-0.492
0
0
0
NHFG
1 4/ 0
89. 2378 TCDDioxin
1746-01-6
6.10
6.42
0
0
0
NLFG
/ 16/ 0
90. 2378 PeCDDioxin8
6.9
7.2
0
0
0
NLFG
/ 29/ 0
91. 2378 HxCDDioxins
7.3
7.6
0
0
0
NLFG
1 291 0
92. 2378 HpCDDioxins
7.8
8.1
0
0
0
NLFG
1 29/ 0
93. OCDD
(Octachlorodibenzo-p-dioxin)
3268-87-9
8.08
8.4
0
0
0
NLFG
/ 29/ 0
94. Diphenylamine
(PKb~13.4)
122-39-4
3.30
3.62
0
0
0
NHFG
/ 4/ 0
95.1,2-Diphenylhydrazine
(PKb~13.2)
122-66-7
1.4
1.7
0
0
0
NHFG
1 4/ 0
CO
ro
ctT
8
3
5>
a
CO
§•
g
i
(n
0>
£
I
to
o*
3
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
k.
References
Common Name
No.
LogK«
Log K„.
M V'
r'
MTV
Comment
96. Disulfoton
298-04-4
2.94
3.26
0
2.3
5.4E4
RATE
1 4/ 6
(K, at C)
O,0-Diethylph08phorodi1hiolc
298-06-6
-2.2
-0.2
0
0.2
0
z
/ 29/ 0
acid (pK,-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
O-Ethylphosphorodithioic
NG
-1
1.0
0
1
0
z
/ 29/ 0
acid (pK,-1.6)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 291 0
Phosphorodithioic acid
15834-33-0
-3.6
-1.6
0
3
0
bb
1 29/64
(PK.-1.7)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 01 0
2-Hydroxyethylethytthioether
110-77-0
0.8
1.1
0
0
0
NLFG
/ 29/ 0
(K. at Pi
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
OEthyl-S42-{ethytthlo)e1tTyll-
94139-29-4
-1.9
0.1
0
0.2
0
z
/ 29/ 0
phosphorodithioic acid(pK,-1.6)
2-Hydroxyethylethylthio-
110-77-0
0.8
1.1
0
0
0
NLFG
/ 29/ 0
ether
O-Ethylphosphorodlthioic
NO
-1
1.0
0
1
0
z
/ 29/ 0
acid (pK.-1.6)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
Phosphorodithioic acid
15834-33-0
-3.6
-1.6
0
3
0
bb
/ 29/ 64
(PK.-1.7)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 0/ 0
(kj
O,0-Diethylph08phorothioic acid
2465-65-8
-2
0
0
0.2
0
z
/ 29/ 0
(pK-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 29/ 0
0-Ethylpho8phorothioic acid
14018-63-4
-1.5
0.5
0
1
0
z
/ 29/ 0
(PK.-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/ 64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
1 01 o
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
1 01 0
2-Thioethylethylthioether
26750-44-7
2.7
3.0
0
0
0
NLFG
1 29/ 0
j
G>
CO
-------
Fate Constants for Hazardous Waste Identification
References
/ 29/ 6
/ 29/ 6
/ 0/ 0
1 291 0
/ 62/ 1
1 29/ 0
1 29/ 0
1 4/ 5
/ 29/ 0
/ 29/ 5
/ 29/ 0
/ 0/ 0
/ 29/ 0
/ 4/ 0
/ 4/ 5
/ 41 0
/ 9/ 0
/ 4/ 0
/ 41 0
Comment
RATE
RATE
NHFG
NLFG
NLFG
NLFG
f
NHFG
NHFG
NHFG
NHFG
NHFG
NHFG
NHFG
1
NHFG
V
CO
*
>•
8
* I.
I ji-
76
Si
i
¦C
o
V
1.7E8
3.0E8
0
0
o o o
0
1.8E5
0
0
0
0
o
3.4E6
0
0
o
o
6.1 E-2
8.9E-2
0
0
5.5E-2
0
0
30.9
0.46
8.9
0
0
0
o
4.8E-3
0
0
o
o
o o o o
o o o
2.5E4
0
7.7E4
0
0
0
o
3.5E3
0
0
o
o
S 8
CO CO ^ CO
Z CNI
4.92
3.5
3.5
-0.210
-0.5
-1.4
-1.9
NA
-1.9
-0.217
0.671
-0.234
-0.30
3.32
0.870
f *
« -1
o o < in
^ *•' Z C\J
4.60
3.2
3.2
-0.53
-0.8
-1.7
-2.2
NA
-2.2
-0.54
0.351
-2.23
-0.62
ooe
0.55
Chemical
Abstract
Service
No.
115-29-7
959-98-8
33213-65-9
7664-93-9
2157-19-9
72-20-8
34015-58-2
14737-72-5
106-89-8
96-24-2
556-52-5
56-81-5
7647-01-0
56-81-5
110-80-5
141-78-6
64-19-7
64-17-5
100-41-4
60-29-7
Common Name
97. Endo8ulfan(Endosulfan I and II,
mixture)
End08ulfan I (alpha)
Endosulfan II (beta)
Sulfuric acid
1,4,5,6,7,7-Hexachloro-bicyclo-
[2.2.1 ]hept-5-ene-2,3-dimethanol
(Endosulfan diol)
o
E
¦a =
^ UJ
"i! si
I *i
C
UJ
CO
Oi
99. Epichlorohydrin
1 -Chloro-2,3-dihydroxypropane
1 -Hydroxy-2,3-propylene
oxide
Glycerol
Hydrochloric acid
Glycerol
100. 2-Ethoxyethanol
(PK.-15.1)
101. Ethyl acetate
Acetic acid
(pK.-4.65)
Ethanol
102. Ethylbenzene
103. Ethyl ether
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
K
References
Common Name
No.
Log
Log
MY
r'
M-'Y'
Comment
Koc/K^/k,
104. Ethyl methacrylate
97-63-2
1.27
1.59
0
0
1.1 E6
g
/ 4/ 0
Methacrylic acid
79-41-4
-1.53
0.470
0
0
0
NHFG
/ 4/ 0
(pK.-4.45)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
105. Ethyl methanesulfonate
62-50-0
-0.27
0.051
0
1.25E3
0
RATE
/ 4/60
Methylsulfonic acid
75-75-2
-2
0
0
0
0
NLFG
/ 29/ 0
(pK. - -0.39)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
106. Ethylene dibromide
106-93-4
1.42
1.74
0
6.3E-1
0
RATE
/ 4/ 3
(1,2-Dibromoethane)
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
1 01 o
Vinyl bromide
593-60-2
1.23
1.55
0
0
0
NLFG
/ 4/ 0
(bp-16°C)
2-Bromoethanol
540-51-2
-0.35
-3.2E-2
0
0.1
1E6
r
/ 4/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
/ 0/ 0
Ethylene oxide
75-21-8
-1.1
-0.792
2.9E5
21
0
/ 4/ 5
Ethylene glycol
107-21-1
-1.5
-1.2
0
0
0
NLFG
/ 29/ 0
-------
Fate Constants for Hazardous Waste Identification
s *
•> 8
/ 4/ 6
/ 4/ 0
/ 29/ 0
/ 4/ 0
/ 29/ 0
/ 29/ 64
/ 0/ 0
/ 0/ 0
1 291 0
1 29/ 0
/ 29/ 0
/ 4/ 0
/ 29/ 0
/ 4/ 0
/ 29/ 64
/ 0/ 0
/ 0/ 0
O
O
/ 29/ 0
Comment
RATE
NHFG
z
NHFG
z
bb
NHFG
NHFG
NLFG
NLFG
z
NHFG
z
NHFG
bb
NHFG
NHFG
NHFG
NHFG
NHFG
CO
•55
8
X
(0
0
1
•C
O
V
<0 OO OO OOOO OOOOOOOO
O
O
O
o£j Of COOOO O Ot- oco 00
O
O
O
0 OO OO OOOO OOOOOOOO
O
O
O
S g
B ^
I'
X -1
2.27
-0.764
4.0
-0.764
2.5
-3.0
NA
NA
2.0
2.0
-1
-0.764
-2.0
-0.764
-3.0
NA
NA
4.95
4.23
-0.7
1*
1.95
-1.08
2
-1.08
0.5
-5
NA
NA
1.6
1.6
-3
-1.08
-4
-1.08
-5
NA
NA
4.63
3.91
-2.7
Chemical
Abstract
Service
No.
52-85-7
67-56-1
15020-55-0
67-56-1
NG
13598-51-1
7664-38-2
7783-06-4
15020-57-2
15020-57-2
1112-38-5
67-56-1
1111-99-5
67-56-1
13598-51-1
7664-38-2
7783-06-4
206-44-0
CO
(O
CO
64-18-6
Common Name
107. Famphur
(|g
Methanol **
0-Methyl-0-p-(W,/V-
dimethylsulfamoyl)-
phenylphosphorothioic acid
(PK.-1.5)
Methanol **
O-p-(W,A/-Dim0thyl8ulfamoyl)-
phenylphosphorothioic acid
(PK.-1.5)
Phosphorothioic acid
(PK.-1.5)
Phosphoric add
Hydrogen sulfide
p-(W,Af-Dimethyl-
8ulfamoyl)phenol
(pK.-8.4J
(kniig
p-(N,/V-Dimethylsulfamoy1)phenol
(PK.-8.4)
O,0-Dimethylpho8phorothioic
acid (PK.-1.6)
Methanol **
O-Methylphosphorothioic
acid (pK.-1.5)
Methanol **
Phosphorothioic acid
(PK.-1.5)
Phosphoric acid
Hydrogen sulfide
108. Fluoranthene
I 109. Fluorene
110. Formic acid
(PK.-3.8)
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
LogK^
Sorption
Log K„„
Chemical Hydrolysis
K K K
M"Y' Y"1 M'Y'
Comment
References
K«/Kow/kh
111. Furan
110-00-9
1.00
1.32
0
0
0
NHFG
/ 4/ 0
112. 2378 TCDFurari
(2,3,7,8-T etrachlorodibenzofuran)
51207-31-9
6.62
6.94
0
0
0
NLFG
/ 4/ 0
113.12378 PeCDFuran
(1,2,3,7,8-Pentachlorodibenzofuran)
57117-41-6
6.5
6.8
0
0
0
NLFQ
/ 29/ 0
114. 23478 PeCDFuran
(2,3,4,7,8-Pentachlorodibenzoluran)
57117-31-4
6.60
6.92
0
0
0
NLFG
/ 16/ 0
115. 2378 HxCDFurans
7.0
7.3
0
0
0
NLFG
/ 29/ 0
116. 2378 HpCDFurans
7.6
7.9
0
0
0
NLFG
/ 29/ 0
117. OCDF
(Octachlorodibenzofuran)
39001-02-0
8.13
8.45
0
0
0
NLFG
/ 29/ 0
118. Heptachlor
76-44-8
5.21
5.53
0
61
0
RATE
/ 62/25
1-Hydroxychlordene
Hydrochloric acid
24009-05-0
7647-01-0
4.5
NA
4.8
NA
0
0
0
0
0
0
NLFG
NHFG
/ 29/ 2
1 01 o
119. Heptachlor epoxide
1024-57-3
4.9
5.2
0
6.3E-2
0
h
/ 29/0
' lepiacnior utot
Heptachlor trtol
126959-40-8
126959-41-9
3.7
2.2
4.0
2.5
0
0
3.9E-3
0
3.2E4
0
h
NLFG
/ 29/ 0
1 29/ 0
120. Hexachlorobenzene
118-74-1
5.411
5.731
0
0
0
NLFG
/ 7/ 1
121. Hexachlorobutadiene
87-68-3
4.46
4.78
0
0
0
NLFG
/ 37/ 1
-------
Fate Constants for Hazardous Waste Identification
8^
P
O O CNJ <0(0 0
Tf Ojj •<* Tf O
/ 4/ 0
/ 19/ 19
/ / o
/ / o
*2 11 1
O
a
o
T—
o
00
o
Comment
NHFG
NLFG
NLFG
NHFG
NLFG
j, RATE
unstable
NLFG
NLFG
NHFG
NHFG
NHFG
k, NLFG
l-
CO
¦a
>>
e
* t
i
¦#
o
§
£
o
V
1.74E6
0
6.5E5
0
0
0
o
O
o
o
o
o
o
o
1.05
0
0.26
0
0
0
o
GO
CM
o
o
o
o
o
o
o o o o o o
o
O
o
o
o
o
o
o
Sorption
Log K„
3.75
NA
3.6
4.28
4.28
NA
3.75
5.04
3.93
7.3
6.58
T—
4.15
Chemical
Abstract
Service
No.
319-84-6
7647-01-0
319-94-8
87-61-6
120-82-1
7647-01-0
319-85-7
77-47-4
NG
67-72-1
70-30-4
193-39-5
78-83-1
78-59-1
143-50-0
S
o>
Common Name
122. alpha-HCH
Hydrochloric acid
1,3,4,5,6-pentachlorocyclo-
hexene
1.2.3-T richlorobenzene
1.2.4-T richlorobenzene
Hydrochloric acid
X
o
X
8
124. Hexachlorocyclopentadiene
1,1 -Dihydroxytetrachkjro-
cyclopentadiene
Polymers
125. Hexachloroethane
126. Hexachlorophene
(PK.-6.1)
127. lndeno[1,2,3-odJpyrene
128. Isobutyl alcohol
(PK.-15.8)
a>
c
2
o
.c
Q.
s
$
130. Kepone
uS
:: WM.
CD
1
lil
® m
I
s
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
k.
K
K.
References
Common Name
No.
Log
Log
M'Y1
r1
M-V
Comment
Koc/K^/k,
132. gamma-HCH
58-89-9
3.40
3.72
0
1.05
1.73E6
/ 1/ 4
(Lindane)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
1,3,4,5,6-pentachlorocyclo-
319-94-8
3.3
3.6
0
0.26
6.5E5
1 29/ 2
hexene
1,2,3-Trichlorobenzene
87-61-6
3.96
4.28
0
0
0
NLFG
1 4/ 6
1,2,4-T richlorobenzene
120-82-1
3.96
4.28
0
0
0
NLFG
/ 4/ 6
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 0
133. Mercury (and compounds N.O.S.)
134. Methacrylonitrile
126-98-7
0.22
0.540
5E2
0
5.2E3
I
/ 4/ 0
Methacryi amide
79-39-0
0.7
1.0
31.5
1.8E-2
0
I
1 291 0
Methacryiic acid
79-41-4
-1.53
0.470
0
0
0
NHFG
1 4/ 0
(pK.-4.45)
Ammonia
7664-41-7
NA
NA
0
0
0
NHFG
/ 0/ 0
135. Methanol
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
136. Methoxychlor
72-43-5
4.90
5.08
0
0.69
1.2E4
38/ 38/ 12
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
2,2-»s(p-methoxyphenyi)-
2132-70-9
4.1
4.4
0
0
0
NLFG
/ 91 0
1,1-dichloroethytene
Anisoin
119-52-8
3.9
4.2
0
6E3
0
m
/ 9/ 0
Anisil
1226-42-2
3.38
3.70
0
0
0
NHFG
/ 4/ 0
137. 3-Methylcholanthrene
56-49-5
7.0
7.3
0
0
0
NHFG
/ 29/ 0
138. Methyl ethyl ketone
78-93-3
-0.03
0.29
0
0
0
NHFG
/ 65/ 1
139. Methyl i9obutyl ketone
108-10-1
0.87
1.19
0
0
0
NHFG
/ 4/ 0
-------
o
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
K
References
Common Name
No.
Log
Log K„.
MY
V
W'Y"1
Comment
Kcc/K^/k,,
140. Methyl methacrylate
80-62-6
0.74
1.06
0
0
1.9E6
RATE
/ 4/ 24
Methacrylic acid
79-41-4
-1.53
0.470
0
0
0
NHFG
/ 4/ 0
(pK.-4.45)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/0
141. Methyl parathlon
298-00-0
2.47
2.79
NG
2.8
NG
n
/ 4/ 39
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
O-Methyl-O-(p-nrtrophenyl)-
7699-30-1
-2.5
-0.5
0
0.2
0
z
1 291 0
phosphorothloic acid (pK.-l.3)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
1 4/ 0
0-(p-Nitrophenyl)pho8phoro-
18429-96-4
0
1
0
z
/ / o
thioic acid (PK.-1.1)
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 01 o
p-Nitrophenol
100-02-7
12.
1.85
0
0
0
NHFG
/ 4/ 0
(PK.-7.0)
p-NHrophenol
100-02-7
1.2
1.85
0
0
0
NHFG
/ 4/ 0
(PK.-7.0)
O.O-Dimethylphosphorothioic acid
1112-38-5
-3
-1
0
0.2
0
z
/ 29/ 0
(PK.-1.6)
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
/ 4/ 0
O-Methylphosphorothioic acid
1111-99-5
-4
-2.0
0
1
0
z
1 291 0
T3
*
0
1
b\
Methanol **
67-56-1
-1.08
-0.764
0
0
0
NHFG
1 4/ 0
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/ 64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 01 o
142. Naphthalene
91-20-3
3.11
3.36
0
0
0
NHFG
38/ 38/ 0
143. 2-Naphthylamine
91-59-8
1.77
2.09
0
0
0
NHFG
/ 4/ 0
(PKb"9-8)
144. Nickel {and compounds N.O.S.)
7440-02-0
2?
Cb
&
3
5T
3
CO
I
Qj
I
5
1
CO
Q.
CD
3
P
to
o*
a
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log
Chemical Hydrolysis
k. K K
mY r1 nr'Y1
Comment
References
Koc/K^/k,
145. Nitrobenzene
98-95-3
1.51
1.83
0
0
0
NLFG
/ 37/ 1
146. 2-Nitropropane
79-46-9
0.23
0.554
0
0
0
NHFG
/ 4/ 0
147. W-Nitroao-di-n-butyiamine
(PK.<1)
924-16-3
2.09
2.41
0
0
0
NHFG
1 291 0
148. N-Nitroaodiethyiamine
(PK.<1)
55-18-5
-0.03
0.290
0
0
0
NHFG
1 29/ 0
149. W-Nitroaodimethylamine
(PK.<1)
62-75-9
0.448
0.768
0
0
0
NHFG
1 291 0
150. W-Nitroaodiphenylarrine
(PK.<0)
86-30-6
2.84
3.16
0
0
0
NHFG
1 29/ 0
151. Af-Nitroao-di-n-propylamine
(PK.<1)
621-64-7
1.03
1.35
0
0
0
NHFG
/ 29/ 0
152. /V-Nitroaomethylethylamlne
(PK.<1)
10595-95-6
1.03
1.35
0
0
0
NHFG
/ 29/ 0
153. W-Nilroaopiperfdine
100-75-4
-0.02
0.305
0
0
0
NHFG
/ 4/ 0
154. W-Nitro so pyrrolidine
930-55-2
-0.57
-0.254
0
0
0
NHFG
/ 4/ 0
155. Octamethy) pyrophosphoramide
S/s(/V,/V-ethylamino)-
phosphoric acid (pK,4.2)
152-16-9
27972-73-2
1.9E3
0
NG
0
NO
0
NLFG
/ / 34
/ / o
-------
ro
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
LogK^
Log K„.
pyrV'
r1
MV
Comment
KclKo.lK
156. Parathion (ethyl)
56-38-2
3.15
3.47
0
2.4
3.7E6
1 4/ 21
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
O-Ethyl-O-(p-nitrophenyl)-
15576-30-4
0
0.2
0
z
/ / o
phosphorothioic acid (pK.-1.2)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFQ
/ 29/ 0
0-(p-Nitrophenyl)phosphoro-
18429-96-4
0
1
0
z
/ / o
thtoic acid (pK,-1.l)
p-Nitrophenol
100-02-7
12.
1.85
0
0
0
NHFG
/ 4/ 0
(PK.-7.0)
Phopsphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 0/ 0
p-Nrtrophenol
100-02-7
1.2
1.85
0
0
0
NHFG
/ 4/ 0
(PK.-7.0)
O.O-Diethylphosphorothioic acid
2465-65-8
-2
0
0
02
0
z
/ 29/ 0
(PK.-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
0-Ethylpho8phorothioic acid
14018-63-4
-1.5
0.5
0
1
0
z
/ 29/ 0
(PK.-1.5)
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/ 64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 0/ 0
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
157. Pentachlorobenzene
608-93-5
5.39
5.183
0
0
0
NLFG
/ 7/ 0
158. Pentachloronitrobenzene (PCNB)
82-68-8
4.57
4.89
0
0
0
NLFG
/ 4/ 0
159. Pentachlorophenol
87-86-5
3.06
5.06
0
0
0
NLFG
/ 4/ 1
(PK.-4.8)
160. Phenol
108-95-2
1.23
1.48
0
0
0
NHFG
/ 4/ 1
(PK.-10)
a
&
g
5T
3
Co
I
&)
I
s
I
c5"
I
:a
g*
0)
o'
3
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log
Sorption
Log K„.
Chemical Hydrolysis
K K K
M'r1 Y"1 MV
Comment
References
161. Phenylenediamine:
1,2-Phenylenediamine
95-54-5
-0.1
0.2
0
0
0
NHFG
1 29/ 0
(pKb-9-3)
1,3-Pheny)enediamine
108-45-2
•0.3
0.05
0
0
0
NHFG
/ 29/ 0
(pKb-8.7)
1,4-Pheny)enediamine
106-50-3
NA
-0.4
0
0
0
NHFG
1 29/ 0
(pKb-7.7)
-------
-b
4^
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
K
References
Common Name
No.
Log
Log K„,
M-'r1
r1
irv
Comment
K~/Ko./*h
162. Phorate
298-02-2
2.64
2.96
0
62
0
RATE
/ 4/ 25
(kn at P-O)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 291 0
OEthyl-S-[(ethyithio)methyl]-
NG
-2.5
-0.5
0
0.2
0
z
1 29/ 0
phosphorodithioic acid
(PK.-1.6)
O-Ethylphosphorodithioic
NG
-1
1.0
0
1
0
z
/ 29/ 0
acid (PK.-1.6)
Phosphorodithioic acid
15834-33-0
-3.6
-1.6
0
3
0
bb
/ 29/ 64
(PK.-1.7)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 01 o
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 29/ 0
Hydroxymethyiethyithio-
15909-30-5
0.2
0.5
0
0
0
NLFG
/ 29/ 0
ether
— (kj
Mercaptomethylethyithioether
29414-49-1
2.0
2.3
0
0
0
NLFG
/ 29/ 0
O.O-Diethyiphosphorothioic acid
2465-65-8
-2
0
0
0.2
0
z
1 29/ 0
(PK.-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
0-Ethylpho8phorothioic acid
14018-63-4
-1.5
0.5
0
1
0
z
/ 29/ 0
(PK.-1.5)
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
/ 01 0
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
(kn at S-C)
Hydroxymethyiethyithioether
15909-30-5
0.2
0.5
0
0
0
NLFG
/ 29/ 0
O.O-Diethylphosphorodithioic
298-06-6
-2.2
-0.2
0
02.
0
z
/ 29/ 0
acid (pK,-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
O-Ethylphosphorodithioic acid
NG
-1
1.0
0
1
0
z
/ 29/ 0
(PK.-1.6)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
1 29/ 0
Phosphorodithioic acid
15834-33-0
-3.6
-1.6
0
3
0
bb
1 29/ 64
(PK.-1.7)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 01 o
Hydrogen sulfide
7783-06-4
NA
NA
0
0
0
NHFG
1 29/ 0
J
&
5T
(O
I
ft
I
s
or
Co
a
a>
I
Q)
O*
3
-------
Common Name
Chemical
Abstract
Service
No.
Sorption
Log K^
Sorption
LogK..
Chemical Hydrolysis
K K K
mY1 r1 m'y-'
Comment
References
Koc/K^/k,
163. Phthalic anhydride
85-44-9
-0.62
0
4.9E5
0
U, RATE
/ 35/22
o-Phthalic acid
(pK.-3.03)
88-99-3
-1.27
0.732
0
0
0
NHFG
/ 4/ 0
164. Polychlorinated biphenyls
(Aroclore)
1336-36-3
0
0
0
NLFG
/ / o
165. Pronamide
23950-58-5
2.63
2.95
59
0
6.1 E2
RATE
/ 4/ 6
3,5-Dichlorobenzoic acid
(pK.-3.46)
1,1 -Dimethyi-2-propyhylannine
(pKb-8.1)
51-36-5
2978-58-7
1.5
•0.63
3.5
-0.306
0
0
0
0
0
0
NLFG
NHFG
1 291 0
1 4/ 0
166. Pyrene
129-00-0
4.92
5.18
0
0
0
NHFG
1 38/ 0
167. Pyridine
(pKb-8.7)
110-86-1
0.34
0.665
0
0
0
NHFG
/ 4/ 1
168. Safrole
94-59-7
2.34
2.66
0
0
0
NHFG
/ 4/ 24
169. Selenium (and compounds N.O.S.)
7782-49*2
170. S»*er {and ooropowxie N.O.S.)
7440-22-4
171. Strychnine and salts
(pKt-4.7)
57-24-9
NA
2.0 "
0
0
0
NLFG
/ 29/ 0
172. Styrene
100-42-5
2.84
3.16
0
0
0
NHFG
/ 37/ 0
173.1,2,4,5-Tetrachlorobenzene
95-94-3
4.284
4.604
0
0
0
NLFG
/ 7/ 0
-------
0>
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
K
References
Common Name
No.
LogK^
Log K„,
MV'
r1
M-Y1
Comment
KclK.IK
174.1,1,1,2-Tetrachloroethane
630-20-6
2.71
3.03
0
1.37E-2
1.13E4
RATE
1 1/13
1,1,2-Trichloroethylene **
79-01-6
2.10
2.42
0
0
0
NLFG
/ 37/ 2
2,2,2-Trichloroelhanol (pK„-3.7)
115-20-8
1.13
1.45
0
0.65
0
V
1 29/ 0
Hydroxyacetic acid
79-14-1
-4
-2
0
0
0
NHFG
1 29/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFQ
/ 01 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 01 o
175.1,1,2,2-Tetrachloroethane
79-34-5
2.07
2.39
0
5.10E-3
1.59E7
RATE
/ 37/13
1,1,2-Trichloroethylene **
79-01-6
2.10
2.42
0
0
0
NLFG
/ 37/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
176. Telrachloroethylene
127-18-4
2.21
2.53
0
0
0
NLFG
/ 37/ 0
177. 2,3,4,6-Tetrachlorophenol
58-90-2
2.32
4.32
0
0
0
NLFG
1 4/ 1
(PK.-5.3)
178. Tetraethyl dithiopyrophosphate
3689-24-5
3.51
3.83
0
84
9E6
O
/ 62/36
(Sulfotep)
O.O-Diethylphosphorothioic acid
2465-65-8
-2
0
0
0.2
0
z
/ 29/ 0
(PK.-1.5)
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
O-Ethylphosphorothioic acid
14018-63-4
-1.5
0.5
0
1
0
z
/ 29/ 0
(PK.-1.5)
Phosphorothioic acid
13598-51-1
-5
-3.0
0
3
0
bb
/ 29/64
(PK.-1.5)
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
/ 01 0
Hydrogen sulfide
7783-06-04
NA
NA
0
0
0
NHFG
/ 01 0
Ethanol
64-17-5
-0.62
-0.30
0
0
0
NHFG
/ 29/ 0
179. Thallium (and compounds N.O.S.)
mmmim
180. Toluene
108-88-3
2.43
2.75
0
0
0
NHFG
/ 29/ 1
181. 2,4-Toluenediamine
95-80-7
0.02
0.337
0
0
0
NHFG
/ 4/ 0
(pKt-90)
2?
fB"
9
§
5)
55"
&
5
i
(a
ft
a
0)
3
?
Q)
O*
3
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
LogK^
Log K„.
V
Comment
Koc / / k,,
182. 2,6-Toluenediamine
823-40-5
0.02
0.337
0
0
0
NHFG
/ 4/ 0
(pK.,-8.9)
183. o-Toluidine
95-53-4
1.24
1.56
0
0
0
NHFG
/ 4/ 0
(pKb-9.3)
184. p-Toluidine
106-49-0
1.24
1.56
0
0
0
NHFG
/ 4/ 0
(pKb-8.9)
185. Toxaphene (chlorinated camphenes)
8001-35-2
4.31
4.63
0
7.0E-2
2.8E4
P
/ 62/24
186. Tribromomethane
75-25-2
2.05
2.37
NG
NG
1E4
t
/ 4/ 1
(Bramoform)
Cartoon monoxide
630-08-0
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
1 01 o
187.1,2,4-Trichlorobenzene
120-82-1
3.96
4.28
0
0
0
NLFG
/ 4/ 2
188.1,1,1-Trichloroethane
71-55-6
2.16
2.47
0
6.4E-1
2.4E6
/ 37/67
1,1 -Dlchloroethytene **
75-35-4
1.79
2.11
0
0
0
NLFG
/ 1/ 2
(bp—31.9°C)
Acetic acid
64-19-7
-223
-0.234
0
0
0
NHFG
1 4/ 2
(pK.-4.73)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
189.1,1,2-T richioroethane
79-00-5
1.73
2.05
0
2.73E-5
4.95E4
RATE
/ 4/ 13
1,1-Dichioroethylene **
75-35-4
1.79
2.11
0
0
0
NLFG
/ 1/ 2
(bp-31.9°C)
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
Chloroacetaldehyde
107-20-0
0.07
0.389
0
7E-3
2.6E4
/ 4/ 2
Hydroxyacetaldehyde
141-46-8
-1.38
-1.06
0
0
0
NHFG
/ 4/ 2
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
190. Trichloroethylene
79-01-6
2.10
2.42
0
0
0
NLFG
/ 37/ 2
(1,1,2-Trichloroethylene)
-------
I*
00
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
References
Common Name
No.
LogK^
Log K„.
NTY"
r1
M'Y1
Comment
K„cl*~IK
191. Trichlorofiuoromethane
75-69-4
2.11
2.43
0
0
0
NLFG.ee
1 4/ 0
(Freon 11: bp-24.1°C)
192. 2,4,5-Trichlorophenol
95-95-4
2.93
3.85
0
0
0
NLFG
/ 4/ 1
(PK.-7.1)
193. 2,4,6-Trichlorophenol
88-06-2
2.25
3.57
0
0
0
NLFG
/ 4/ 1
(PK.-6.4)
194. 2,4,5-Trichlorophenoxyacetic acid
93-76-5
1.43
3.43
0
0
0
NLFG
/ 4/ 0
(PK.-3.0)
195. 2-(2,4,5-Trichlorophenoxy)propionic
93-72-1
1.74
3.74
0
0
0
NLFG
/ 4/ 1
acid (Silvex: (pK.-3.4)
196.1,2,3-T richloropropane
96-18-4
1.66
1.98
0
1.7E-2
3.6E3
RATE
/ 4/ 6
~K - - - -
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
2,3-Dichloro-1 -propanol
616-23-9
0.5
0.8
0
0.46
1.8E5
/ 29/ 3
Epichlorohydrin
106-89-8
-0.53
-0.210
2.5E4
30.9
0
/ 4/ 5
1 -Chloro-2,3-dihydroxy-
96-24-2
-0.8
-0.5
0
0.46
1.8E5
f
/ 29/ 0
propane
1-Hydroxy-2,3-
556-52-5
-1.7
-1.4
7.7E4
8.9
0
/ 29/ 5
propyiene oxide
Glycerol
56-81-5
-2.2
-1.9
0
0
0
NHFG
1 29/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
1 01 0
Glycerol
56-81-5
-2.2
-1.9
0
0
0
NHFG
/ 29/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
2,3-Dichloropropene
78-88-6
1.8
2.1
0
1.8
0
X
/ 29/ 0
2-Chloro-3-hydroxypropene
5976-47-6
-0.1
0.25
0
0
0
NLFG
/ 4/ 0
Hydrochloric acid
7647-01-0
NA
NA
0
0
0
NHFG
/ 0/ 0
197.1,1,2-Trichloro-1,2,2-trifiuoro-
76-13-1
2.97
3.29
0
0
0
NLFG
/ 4/ 0
ethane
J
CD
&
En
5T
(JT
&
§
i
(o
I
3
&>
o*
3
-------
Chemical
Chemical Hydrolysis
Abstract
Service
Sorption
Sorption
K
K
K
References
Common Name
No.
LogK«
Log K_
M-'V
r1
MY
Comment
198. sym-Trinitrobenzene
99-35-4
1.05
1.37
0
0
0
NHFG
1 4/ 0
(1,3,5-T rinitrobenzene)
199. Tr/s(2,3-dibromopropyl)pho8phate
126-72-7
3.19
3.51
0
8.8E-2
3.0E5
RATE
/ 4/ 24
(kj
0,0-(2t3-Dibromopropyl)-
5412-25-9
0
0.2
0
z
/ / o
pho8phoric acid (pK.-0.8)
0-(2,3-Dibromopropyl)-
5324-12-9
0
1
0
z
/ / o
phosphoric acid (pK.-1.3)
2,3-Dibromo-1 -propanol
96-13-9
1.10
1.42
0
1.4
5.4E5
cc
/ 29/ 0
Phosphoric acid
7664-38-2
NA
NA
0
0
0
NHFG
1 01 o
2,3-Dibromo-1 -propanol
96-13-9
1.10
1.42
0
1.4
5.4E5
cc
1 291 0
Hydrobromic add
10035-10-6
NA
NA
0
0
0
NHFG
1 01 o
Epibromohydrin
3132-64-7
0.2
0.5
1.9E4
1.6E1
0
/ 29/ 41
l-Bromo-2,3-
4704-77-2
-1.18
-0.857
0
1.4
5.4E5
cc
/ 4/ 0
dihydroxy propane
1-Hydroxy-2,3-
556-52-5
-1.7
-1.4
7.7E4
8.9
0
/ 29/ 5
propylene oxide
Glycerol
56-81-5
-2.2
-1.9
0
0
0
NHFG
/ 29/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
/ 0/ 0
Glycerol
56-81-5
-2.2
-1.9
0
0
0
NHFG
/ 29/ 0
2,3-Dibromo-1 -propanol
96-13-9
1.10
1.42
0
1.4
5.4E5
CC
/ 29/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
/ 01 0
2-Bromo-1,3-propanedlol
4704-87-4
-1.4
-1.1
0
2
9E5
q
1 29/ 0
Glycerol
56-81-5
-2.2
-1.9
0
0
0
NHFG
1 29/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
1 01 0
(|g
0,0(2,3-Dibromopropyl)-
5412-25-9
0
0.2
0
z,dd
1 1 o
phosphoric acid (pK,-0.8)
2,3-Dibromo-1 -propanol
96-13-9
1.10
1.42
0
1.4
5.4E5
CC
/ 29/ 0
2-Bromo-2-propen-1 -ol
598-19-6
0.43
0.75
0
0
0
NLFG
/ 29/ 0
Hydrobromic acid
10035-10-6
NA
NA
0
0
0
NHFG
/ 01 o
200* Vanadium
7440-62-2
201. Vinyl chloride
75-01-4
1.04
1.36
0
0
0
NLFG
/ 1/ o
(Chloroethene: bp - -13.4°C)
3.
•K.
<0
-------
en
o
Common Name
Chemical
Abstract
Service
No.
Sorption
Log Kc
Sorption
Log K„.
Chemical Hydrolysis
K K K
M-'r' r' m-'y1
Comment
References
K.IK-IK
202. Xylenes
1330-20-7
0
0
0
NHFG
1 1 o
(mixture of three isomers)
o-Xylene
95-47-6
3.02
3.34
0
0
0
NHFG
/ 29/ 0
m-Xylene
108-38-3
3.09
3.41
0
0
0
NHFG
/ 29/ 0
p-Xylene
106-42-3
3.12
3.44
0
0
0
NHFG
1 291 0
203. Zinc (and compounds N.O.S.)
7440-66-6
CD
&
In
5T
-------
g) The hydrolysis rate constant was estimated by analogy to be 0.6 of methyl methacrytate'8.
h) The hydrolysis rate constant for heptachlor epoxide was assumed by analogy to be the same as dieldrin's. The reaction to the final product heptachlor triol occurs through
the intermediate heptachlor diol, for which a rate estimate was assumed to be 1/10 the rate of 2-chloro-ethanol.
i) The hydrolysis rate constants were assumed by analogy to be the same as lindane's.
j) Hydrolysis of hexachlorocyclopentadiene results in the formation of 1,1-dihydroxytetrachlorocyclopentadiene which is an unstable product. Its degradation leads to the
formation of polymers which cannot be identified.
k) Kepone hydrates in an aqueous medium. The sorption coefficient of the hydrated form may be orders of magnitude lower than the coefficient of the unhydrated form. The
given log values are for the unhydrated form. A value for the hydrated form cannot be estimated.
I) The hydrolysis rate constants for methacrylonitrile and its product methacrylamide were assumed by analogy to be the same as those for acrylonitrile and its product
acryi amide.
m) The product of methoxychlor, anisoin, degrades to anisil by autooxidation with an estimated half-life of one hour.
n) The hydrolysis rate was determined at a pH<8.
o) The hydrolysis rate constants for tetraethyl dithiopyrophosphate were based by analogy on the rate constants of tetraethyl pyrophosphate and tetraethyl
monothiopyrophosphate. The rate constants of tetraethyl pyrophosphate were divided by 10 as an adjustment for the two sulfur substituents in tetraethyl
dithiopyrophosphate.
p) Toxaphene is produced by the chlorination of camphene and is a complex mixture of at least 177 C10 polychloro- derivatives. It has an approximate overall empirical
formula of C10H10CI8 (The Merck Index, Eleventh Edition). Products can, therefore, not be identified.
q) The hydrolysis rate constants for 2-bromo-1,3-propar>edlol were estimated by analogy to be five times those of 2,3-dichloropropanor8 (see #196) because of the two
hydroxide groups and the greater reactivity of bromine.
r) The hydrolysis rate constants for 2-bromoethanol were estimated by analogy to be three times larger than those of 2-chloroethanol because of the greater reactivity of
bromine.
8) The hydrolysis rate constants for the da- and trana-1,3-dichloropropene were assumed by analogy to be the same as 3-chloropropene's (#43).
t) The hydrolysis rate constants for bromodichloromethane, chlorodibromomethane, and tribromomethane were determined in 66.67% (v/v) dioxane/water.
u) Phthalic anhydride hydrolyzes to o-phthalic acid with a half-life of less than one minute. A value for the anhydride would be meaningless.
v) The hydrolysis rate constant for 2,2,2-trichloroethanol was assumed by analogy to be the same as 1,1,1 -trichloroethane's (see #186).
w) QSAR model computations have indicated that the half-life of this halogenated methane is several thousand years. Its hydrolysis process was, therefore, designated as
NLFG.
x) The hydrolysis rate constant for 2,3-dichloropropene was assumed by analogy to be the same as 2-bromo-3-chioropropene's (see #58).
01
-------
y) The log value for technical grade chlordane was calculated by averaging the measured values of the cis- and trans- Isomers. The hydrolysis rate constant given is
for the cia- isomer only. The trans- isomer will not hydrolyze.
z) The hydrolysis rate constant for the degradation of the organophosphorus diester to the monoester was estimated to be smaller than the parent's by a factor of ten, whereas
the rate constant for the degradation of the monoester to the acid was estimated to be half the rate of the parent's9. These estimated rate constants were based on the
average of the neutral rate constants of five organophosphorus compounds.
aa) The hydrolysis rate constants for dichloromethane were extrapolated to 25°C from elevated temperatures.
bb) The hydrolysis rate constant was estimated by extrapolation. Because the value was estimated, no distinction was made of the fact that hydrolysis of the phosphorodKhioic
acid is slightly faster than the monoacid.
cc) The hydrolysis rate constants for 2-bromo-3-chloropropanol, 2,3-dibromo-1 -propanol, and 1 -bromo-2,3-dihydroxypropane were estimated by analogy to be three times larger
than those of 2,3-dichloro-1 -propanol (see #196) because of the greater reactivity of bromine.
dd) The alkaline hydrolysis pathway of the diester is identical to its neutral pathway.
ee) Half-lives of polyhalogenated methanes are usuaSy larger than 50 years. The half-life of trichlorofluoromethane is estimated to be larger than 50 years. Its hydrolysis
prace88 is, therefore, designated as NLFG.
ff) The hydrolysis rate constants for aramite and chlorobenzilate were determined experimentally in ERL-Athens' laboratory. Products, except the hydrogen sulfites, were
confirmed by spectral analyses. The hydrolysis rate constants for the products were estimated.
gg) The hydrolysis rate constants were assumed to be the same as the parent's.
-------
Part I
TABLE 2. SAR computed reductive rate constants for selected halogenated aliphatics
and nitroaromatics.
Halogenated Aliphatics
Chemical
Abstract
Service No.
1%
Organic Carbon
k(year"1)
0.02%
Organic Carbon
k(year1)
26. Bromodichloromethane
75-27-4
1.2E3
1.9E-1
27. Bromomethane
74-83-9
1.4E2
2.2E-2
33. Carbon tetrachloride
56-23-5
5.8E1
9.3E-3
39. Chlorodibromomethane
124-48-1
1.2E3
1.8E-1
40. Chloroform
67-66-3
2.6E1
4.2E-3
58. l,2-Dibromo-3-chloropropane
96-12-8
2.4E2
3.8E-2
59. Dibromomethane
74-95-3
4.0E2
6.4E-2
64. 1,1-Dichloroethane
75-34-3
1.1E1
1.7E-3
65. 1,2-Dichloroethane
107-06-2
4.0
6.5E-4
69. Dichloromethane
75-09-2
8.7
1.4E-3
71. 1,2-Dichloropropane
78-87-5
5.4
8.5E-4
72. 1,3-Dichloropropene
542-75-6
6.7
1.1 E-3
106. Ethylene dibromide
106-93-4
1.7E2
2.7E-2
125. Hexachloroethane
67-72-1
2.8E1
4.5E-3
174. 1,1,1,2-Tetrachloroethane
630-20-6
7.0
1.1 E-3
175. 1,1,2,2-Tetrachloroethane
79-34-5
7.5
1.2E-3
186. Tribromomethane
75-25-2
1.2E3
1.8E-1
188. 1.1,1-Trichloroethane
71-55-6
1.5E1
2.4E-3
189. 1,1,2-Trichloroethane
79-00-5
5.4
8.5E-4
191. Trichlorofluoromethane
75-69-4
5.8E1
9.3E-3
196. 1,2,3-Trichloropropane
96-18-4
4.3
6.8E-4
197. 1,1,2-Trichloro-1,2,2-trifluoroethane
76-13-1
4.0E1
6.4E-3
Nitroaromatics
Chemical
Abstract
Service No.
1%
Organic Carbon
k(year"1)
0.02%
Organic Carbon
kjyear'1)
30. Dinoseb
88-85-7
5.0E3
8.8E1
82. 1,3-Dinitrobenzene
99-65-0
8.0E2
1.4E2
83. 2,4-Dinitrophenol
51-28-5
2.2E3
3.9E2
84. 2,4-Dlnitrotoluene
121-14-2
6.6E2
1.2E2
85. 2,6-Dinitrotoluene
606-20-2
8.0E2
1.4E2
141. Methyl parathion
298-00-0
1.2E2
2.2E1
145. Nitrobenzene
98-95-3
3.0E2
5.2E1
156. Parathion
56-38-2
1.2E2
2.2E1
198. sym-Trinitrobenzene
99-35-4
2.2E3
3.9E2
-------
Part I 55
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-------
56 Fate Constants for Hazardous Waste Identification
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-------
Parti 57
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36. Coates, H. 1949. The chemistry of phosphorus insecticides. Ann. Appl. Biol 36:156-159.
37. Banerjee, S., S.H. Yalkowsky, and S.C. Valvani. 1980. Water solubility and octanol/water
partition coefficients of organics. Limitations of the solubility-partition coefficient
correlation. Environ. Sci. Technol. 14(10):1227-1229.
38. KarickhofF, S.W., D.S. Brown, and T.A. Scott. 1979. Sorption of hydrophobic pollutants
on natural sediments. Water Res. 13:241-248.
39. Smith, J.H., W.R. Mabey, N. Bohonos, B.R. Holt, S.S. Lee, T.-W. Chou, D.C. Bomberger,
and T. Mill. 1978. Environmental Pathways of Selected Chemicals in Fresh Water
Systems. Part II: Laboratory Studies. U.S. Environmental Protection Agency, Athens,
GA, EPA-600/7-78-074.
40. Elliot, S., E. Lu, and F.S. Rowland. 1989. Rates and mechanisms for the hydrolysis of
carbonyl sulfide in natural waters. Environ. Sci. Technol. 23(4):458-461.
41. Hine, J., A.M. Dowell, Jr., and J.E. Singley, Jr. 1956. Carbon dihalides as intermediates
in the basic hydrolysis of haloforms. IV. Relative reactivities of haloforms. J. Am. Chem.
Soc. 78:479-482.
42. Bolt, H.M., R.J. Laib, and J.G. Filser. 1982. Reactive metabolites and carcinogenicity of
halogenated ethylenes. Biochem. Pharmacol. 31:1-4.
43. Hudson, R.F. 1965. Structure and Mechanism in Organophosphorus Chemistry, New
York, NY: Academic Press.
44. Kirby, A.J. and S.G. Warren. 1967. The Organic Chemistry of Phosphorus, New York,
NY: Elsevier Publishing Company.
-------
58
Fate Constants for Hazardous Waste Identification
45. Ingold, C.K. 1969. Structure and Mechanism in Organic Chemistry, 2nd ed., Ithaca, NY:
Cornell University Press, p. 1131.
46. Schellenberg, K., C. Leuenberger, and R.P. Schwarzenbach. 1984. Sorption of chlorinated
phenols by natural sediments and aquifer materials. Environ. Set Technol.
18(9):652-657.
47. Jafvert, C.T. 1990. Sorption of organic acid compounds to sediments: Initial model
development. Environ. Toxicol Chem. 9:1259-1268.
48. Jafvert, C.T., J.C. Westall, E. Grieder, and R.P. Schwarzenbach. 1990. Distribution of
hydrophobic ionogenic organic compounds between octanol and water: Organic acids.
Environ. Sci. Technol. 24(12):1795-1803.
49. Hassett, J.J., J.C. Means, W.L. Banwart, and S.G. Wood. 1980. Sorption Properties of
Sediments and Energy-related Pollutants. U.S. Environmental Protection Agency,
Athens, GA, EPA-600/3-80-041.
50. Lyman, W.J., W.F. Reehl and D.H. Rosenblatt. 1982. Handbook of Chemical Property
Estimation Methods: Environmental Behavior of Organic Compounds. McGraw-Hill Book
Company, New York, New York.
51. Wolfe N.L. and D.L. Macalady. 1992. New Perspectives in redox chemistry: Abiotic
transformations of pollutants in groundwater and sediments. J. Contamin. Hydrol.
1992:17-34.
52. March, J. 1977. Advanced Organic Chemistry Reactions, Mechanisms and Structure. 2nd
ed., McGraw-Hill, New York.
53. Jafvert, C.T. and N.L. Wolfe. 1987. Degradation of selected halogenated ethanes in
anoxic sediment-water systems. Environ. Toxicol. Chem. 6(ll):827-837.
54. Weber, E.J. and N.L. Wolfe. 1987. Kinetic studies of aromatic azo compounds in
anaerobic sediment/water systems. Environ. Toxicol. Chem. 6(12):911-919.
55. Wolfe, N.L., P.F. Sanders, and M.C. Delgado. Reduction of nitroaromatic compounds in
anaerobic sediment/water systems. Environ. Toxicol. Chem. Submitted for publication,
1993.
56. Wolfe, N.L. and M.C. Delgado. Structure-activity relationships for the reduction of p-
substituted nitrobenzenes in anaerobic sediments. Environ. Toxicol. Chem. Submitted for
publication, 1993.
57. Wolfe, N.L., W. Peijnenburg, H. d Hollander, H. Verboom, and D. v d Meent. Kinetics of
reductive transformations of halogenated hydrocarbons under anoxic reaction conditions.
Environ. Toxicol. Chem. Submitted for publication, 1993.
58. Wolfe, N.L., W. Peijnenburg, H. d Hollander, H. Verboom, and D. v d Meent. Structure
reactivity relationships for predicting reductive transformation rate constants of
halogenated hydrocarbons in anoxic sediment systems. Environ. Toxicol. Chem.
Submitted for publication, 1993.
59. Pryor, W.A. 1966. Free Radicals, McGraw-Hill, New York.
60. Barnard, P.W.C. and R.E. Robertson. 1961. The hydrolysis of a series of straigh-chain
alkyl methanesulphonic esters in water. Can. J. Chem. 39:881-888.
-------
Part/
59 (,«>
61. Elliott, S. 1990. Effect of hydrogen peroxide on the alkaline hydrolysis of carbon disulfide.
Environ. Sci. Technol. 24:264-267.
62. Ellington, J.J. and F.E. Standi, Jr. 1988. Octanol/water Partition Coefficients for
Evaluation of Hazardous Waste Land Disposal: Selected Chemicals. U.S. Environmental
Protection Agency, Athens, GA, EPA/600/M-88/010.
63. Fells, I. and E.A. Moelwyn-Hughes. 1958. The kinetics of the hydrolysis of methylene
dichloride. J. Chem. Soc. Part H 268:1326-1333.
64. Brois, S.J. 1967. A new synthesis of thiophosphoric acid. Chem. Communications 1237-
1238.
65. Hansch, C. and S.M. Anderson. 1967. The effect of intramolecular hydrophobic bonding
on partition coefficients. J. Org. Chem. 32(8):2583-2586.
66. Shen, C.Y. and F.W. Morgan. 1973. Hydrolysis of Phosphorus Compounds. In:
Environmental Phosphorus Handbook. E.J. Griffith, A. Beeton, J.M. Spencer, and D.T.
Mitchell (Eds.). John Wiley & Sons, New York. p. 255-259.
67. Gerkens, R.R. and J.A. Franklin. The rate of degradation of 1,1,1-trichloroethane in
water by hydrolysis and dehydrochlorination. Chemosphere 19(12):1929-1937.
-------
Pari II 61
1. Acenaphthene
Acenaphthene will not hydrolyze. It has no hydrolyzable functional group.
Acenaphthene
2. Acetone
Acetone will not hydrolyze; however, it may undergo other abiotic transformation processes.
O
h3c—
-------
62 Fate Constants for Hazardous Waste Identification
3. Acetonitrile
Acetonitrile is resistant to hydrolysis. Hydroxide or hydronium is required to facilitate
hydrolysis. Hydrolysis proceeds through the intermediate amide to the final product, acetic
acid.
H3C—C—N
Acetonitrile
HO"
* i
h3c-c—nh2
Acetamide
H
HO
O
II
H3C—C—OH + NH3
Acetic acid
-------
Part II
63
4. Acetophenone
Acetophenone will not hydrolyze; however, it may undergo other abiotic transformation
processes.
O
d—ChU
Acetophenone
5. Acrolein
Acrolein undergoes a rapid addition of water across the double bond (Michael addition) to
yield 3-hydroxy-1 -propanal.
H H
H2c=k-k=o
Acrolein
H2O
H H H
HfwUUi-O
I T
H H
3-Hydroxy-1 -propanal
-------
64 Fate Constants for Hazardous Waste Identification
6. Acrylamide
Acrylamide is an intermediate in the hydrolysis of acrylonitrile to acrylic acid. At high
concentrations of hydroxide, acrylamide polymerizes. The reported neutral hydrolysis rate
constant was determined at pH 7 by monitoring the disappearance of acrylamide from the
solution. This constant, together with the acid hydrolysis rate constant, can be used to
calculate persistence. The end product of hydrolysis is acrylic acid.
O
H2C=CH-(!-*NH2
Acrylamide
H+
HoO
H9C=CH-(!1-0H +
NH,
Acryf c acid
7. Acrylonitrile
See compounds #3 and #6. Acrylonitrile hydrolyzes to acrylic acid through the intermediate
acrylamide.
H2C-CH-C-N
Acrylonitrile
H+
HO-
HjjC-CH-i-NHa
Acrylamide
HgO
H2C=CH-£-OH + NH3
Acrylic acid
-------
Part II 65
8. Aldrin
The chlorinated tricyclic structure of aldrin is common to several persistent pesticides. All
aldrin chlorine atoms are either protected from nucleophilic attack (bridgehead carbon) or
are nonreactive (on the sp2 carbon). The previously reported hydrolysis rate constant for
aldrin in reference 6 was based on disappearance kinetics without confirmation of hydroly-
sis products. For this report, the hydrolysis experiments were repeated in sealed glass
ampules, and no disappearance of the aldrin was observed after 2 weeks at pH 11 and
85°C. Aldrin has been designated the assignment of NLFG.
Aldrin
9. Aniline
Aniline will not hydrolyze; however, it may undergo other abiotic transformation processes.
NH?
6
Aniline
-------
Fate Constants for Hazardous Waste Identification
11. Aramite
The sulfite bond in Aramite is very susceptible to hydrolysis (see endosulfan, #97). Initial
hydrolysis of Aramite proceeds with cleavage of either of two sulfoxide bonds. This initial
hydrolysis yields four products, two alcohols and two hydrogen sulfites. Hydrolysis of the
hydrogen sulfites continues at a rate comparable to that of Aramite. Hydrolysis of 2-
chloroethanol is discussed with 1,2-dichloroethane, #65.
Aramite
H20 HO
HaC
H2CH—O—S—OH + H3C
6h3
:H2CH—OH + HO—S—O—CHjCHjCl +CI—CHj-CHj-OH
CHj 2-Chloroethanol
2-Chloroeth^hydrogensulflls
2-Chloroethanol
1 -Me»i^-2-[p-(1,1 -dimettiyte1tiy()pfisnoxy)athanol
1 -Methyl-2-lp-(1,1 -dlmettiyfethy()phenoxy)etiy!hydrogensulfite
H..CH—OH + H2S0,
CI—CHj-CHj-OH + H2SO,
2-Chloroethanol
1 -Methyl-2-|p-(1,1 -dlmettiytethyi)phenoxy)ethanol
H,d-H3H2 + HCf *•
Ethylene o)dde
HO-CHj-CHj-OH
Ethylene glycol
-------
Part II 67
14. Benz[a]anthracene
Benz[a]anthracene will not hydrolyze. It has no hydrolyzable functional group.
Benzfajarrthracene
15. Benzene
Benzene will not hydrolyze. It has no hydrolyzable functional group.
0
Benzene
-------
68 Fate Constants for Hazardous Waste Identification
16. Benzidine
Benzidine will not hydrolyze; however, it may undergo other abiotic transformation pro-
cesses.
•NH.
Benzidine
17. Benzo[fljfluoranthene
Benzo[fc]fluoranthene will not hydrolyze. It has no hydrolyzable functional group.
Benzo[b]fluoranthene
-------
Part II 69
18. Benzo[a]pyrene
Benzo[a]pyrene will not hydrolyze. It has no hydrolyzable functional group.
Benzo[a]pyrene
19. Benzotrichloride
Hydrolysis of benzotrichloride proceeds through nucleophilic substitution of chlorine by
H20. The halohydrin formed by this displacement is unstable and reacts further to yield
benzoic acid.
CCl:
Benzotrichloride
HoO
Benzoic acid
-------
70 Fate Constants lor Hazardous Waste Identification
20. Benzyl alcohol
Benzyl alcohol will not hydrolyze. It has no hydrolyzable functional group.
HoOH
Benzyl alcohol
21. Benzyl chloride
Hydrolysis of benzyl chloride occurs through nucleophilic displacement of chlorine by HjO.
Hydrolysis is not mediated by hydroxide.
HoCI
Benzyl chloride
H20
h2-oh
+ HCI
Benzyl alcohol
-------
Part II 71
23. g/s(2-chloroethyl)ether
Hydrolysis of feis(2-chloroethyl)ether occurs through nucleophilic displacement of chlorine
with H20. The monochloroether formed by this reaction will undergo a second substitution
by H20 to yield fcis(2-hydroxyethyl)ether and intramolecular displacement of chlorine to
yield dioxane.
CICH2CH2-0-CH2CH2CI
Bis(2-chloroethyl)ether
h2o
I'
ho-ch2ch2—o-ch2ch2ci + HCI
2 - (2-Chtoroethoxy)ethanoI
HO—CH2CH2—O—CH2CH2-OH + HCI
Bi s(2-hydroxyethyl)ether
0
xr
p-Dioxane
-------
72
Fate Constants for Hazardous Waste Identification
24. 0/s(2-chloroisopropyl)ether
The literature hydrolysis rate constant for 6zs(2-chloroisopropyl)ether seems to be question-
able. This value was estimated by analogy to fcis(2-chloroethyl)ether by Mabey et al.8 The
value for bis(2-chloroethyl) ether was determined in aqueous dioxane at 100°C and
extrapolated to 20°C by Mabey et al.8 However, Mabey et al.8 named the compound bis(2-
chloroisopropyl)ether but give the Chemical Abstract Service number and structure for
6is(l-chloroisopropyl)ether. Moreover, it is questionable whether feis(2-chloroisopropyl)ether
should be the compound on the list or whether it should be 6is(l-chloroisopropyl)- ether.
Our Pathway Analysis Team deliberated and concluded that 6is(2-chloroisopropyl)- ether is
a halohydrin and is, thus, unstable. If the intended compound on the list is bis( 1-
chloroisopropyl)ether, the hydrolysis rate should be the one given by Mabey et al.8 (kn =
3.5E-2 Yx). However, if the intended compound is bis(2-chloroisopropyl)ether, its half-life is
on the order of minutes because of its instability.
C
Bis(2-chloroisopropy!)ettier
H20
+ HCI
(2-Hydroxyisopropyl-2-chloroisopropyl)ether
+ HC!
Bis(2-hydroxyisopropyl)ether
-------
Part II 73
25. g/s(2-ethylhexyl)phthalate
Bis(2-ethylhexyl)phthalate will hydroiyze by nucleophilic attack of HO" at the ester car-
bonyl group to give 2-ethylhexyl hydrogen phthalate and 2-ethylhexanol. The monoester
will undergo further base-mediated hydrolysis to o-phthalic acid and 2-ethylhexanol.
O CH2CH3
II .23
C—O—C H2~C H—(C H2)3C h3
<^-0-CH2-CH—(CH2)3CH3
O CH2CH3
Bis(2-e1hylhexyl)phthalate
HO'
aC-OH
-------
74
Fate Constants for Hazardous Waste Identification
26. Bromodichloromethane
Hydrolysis of bromodichloromethane occurs initially by proton abstraction followed by
formation of the carbene, which reacts with HO to form carbon monoxide and the mineral
acids.
CHBrC!2
Bromodichloromethane
HO-
CO + HCI + HBr
Carbon monoxide
27. Bromomethane
Hydrolysis of bromomethane proceeds through nucleophilic substitution of bromine by HjO
to yield methanol and hydrobromie acid.
CH3Br
Bromomethane
H20
CH3OH + HBr
Methanol
-------
Part II 75
28. Butanol
Butanol will not hydrolyze. It has no hydrolyzable functional group.
CH3CH2CH2CH2OH
Butanol
29. Butyl benzyl phthalate
Butyl benzyl phthalate is a mixed ester formed by condensation of phthalic acid with two
different alcohols. The hydrolysis mechanism is the same as described for 6is(2-ethyl-
hexyl)phthalate (#25) with the two resulting monoesters undergoing further hydrolysis to o-
phthalic acid and the corresponding alcohols.
—o— CH:
-------
76 Fate Constants for Hazardous Waste Identification
30. 2-seo-Butyl-4,6-dinltrophenol
2-sec-Butyl-4,6-dinitrophenol will not hydrolyze; however, it may undergo other abiotic
transformation processes.
2-sec-ButyK6-dinitrophenol
32. Carbon disulfide
Hydrolysis of carbon disulfide occurs by nucleophilic attack of HO. The initial hydrolysis
product is carbonyl sulfide, which reacts further with H20 or HO to give carbon dioxide and
hydrogen sulfide.
S=C=S
Carbon disulfide
HO"
o=c=s
Carbonyl sulfide
0=C=0 + H2S
Carbon dioxide
-------
Part II 77
33. Carbon tetrachloride
Hydrolysis of carbon tetrachloride occurs by reaction with H^O to yield carbon dioxide and
the mineral acid.
CCI4
Carbon tetrachloride
H20
HCI
Carbon dioxide
34. Chlordane
Hydrolysis of chlordane proceeds by nucleophilic substitution of chlorine by HO to give
2)4»5,6,7,8,8-heptachloro-3a)4)7,7a-tetrahydro-4,7-methano-lH-indene, which will not be
susceptible to further hydrolysis.
Chlordane
h2o
OH
2l4,5,67,8,8-HeptacHofO-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene
-------
78
Fate Constants for Hazardous Waste Identification
35. p-Chtoroaniline
p-Chloroaniline will not hydrolyze to any reasonable extent; however, it may undergo other
abiotic transformation processes.
NH.
p-Chtoroaniline
36. Chlorobenzene
Chlorobenzene will not hydrolyze to any reasonable extent; however, it may undergo other
abiotic transformation processes.
Chlorobenzene
-------
Part II
79
37. Chlorobenzilate
Hydrolysis of chlorobenzilate is analogous to the phthalate esters and proceeds through
nucleophilic attack of HO at the ester carbonyl. The resulting acid is stable in the ionic
form, but the protonated form that would exist at acidic pH values will decarboxylate with
concurrent oxidation to yield carbon dioxide and p,p'-dichlorobenzophenone. The conversion
of 6is(p-chlorophenyl)hydroxyacetic acid to p,p'-dichlorobenzophenone was estimated to
proceed at 10% of the hydrolysis rate of the parent.
CI
Chlorobenzilate
HO
Bls(p-chbrophenyl)hydroxyacetic acid
CH3CH2-OH
Ethanol
«K>K>
p.p'-Dichlorobenzophenone
-------
80 Fate Constants for Hazardous Waste Identification
38. 2-Chloro-1,3-butadiene
2-Chloro-l,3-butadiene will not hydrolyze to any reasonable extent; however, it may un-
dergo other abiotic transformation processes.
J'
H2C—c—ch=ch2
2-Chloro-1,3-butadiene
39. Chlorodibromomethane
Hydrolysis of chlorodibromomethane occurs initially by proton abstraction followed by
formation of the carbene, which reacts with HO" to form carbon monoxide and the mineral
acids.
CHBr2CI
C hlorodibromomethane
H20, HO'
CO + HBr + HCI
Carbon monoxide
-------
Part II 81
40. Chloroform
Hydrolysis of chloroform occurs initially by proton abstraction followed by formation of the
carbene, which reacts with HO' to form carbon monoxide and the mineral acid.
CHCI3
Chloroform
H20,H0'
1'
CO + HCI
Carbon monoxide
41. Chloromethane
Chloromethane has a negative boiling point and exists in a gaseous state at room tempera-
ture. Its hydrolysis pathway has not been addressed.
CH3CI
Chloromethane
-------
82 Fate Constants for Hazardous Waste Identification
42. 2-Chlorophenol
2-Chlorophenol will not hydrolyze to any reasonable extent; however, it may undergo other
abiotic transformation processes.
2-Chlorophenol
43. 3-Chloropropene
Neutral hydrolysis of 3-chloropropene occurs through the formation of the allylic carbonium
ion, which reacts with H20 to give 3-hydroxypropene and the mineral acid.
H2C=CH-CH2CI
3-CMoropropene
H20
i'
H2C=CH—CH2-OH + HCI
3-Hydroxypropene
-------
Part II 83
45. Chrysene
Chrysene will not hydrolyze. It has no hydrolyzable functional group.
Chrysene
47. o-Cresol
o-Cresol will not hydrolyze. It has no hydrolyzable functional group.
OH
CH,
o-Cresol
-------
84 Fate Constants for Hazardous Waste Identification
48. ro-Cresol
m-Cresol will not hydrolyze. It has no hydrolyzable functional group.
OH
CH;
m-Cresol
49. p-Cresol
p-Cresol will not hydrolyze. It has no hydrolyzable functional group.
p-Cresol
-------
Part II 85
50. Cumene
Cumene will not hydrolyze. It has no hydrolyzable functional group.
,CH(CH3)2
Cumene
51. Cyanide
Cyanide will hydrolyze by nucleophilic attack of H20 resulting in carbon dioxide and ammo-
nia.
CN
H20
r
0=C=0 + NHa
Carbon dioxide
-------
86
Fate Constants for Hazardous Waste Identification
52. 2,4-Dichlorophenoxyacetic acid
2,4-Dichlorophenoxyacetic acid will not hydrolyze to any reasonable extent.
2,4-Dichlorophenoxyacetic acid
53. DDD
The reaction of DDD occurs by the elimination of chlorine (dehydrochlorination) to give 2,2-
6is(4-chlorophenyl)-l-chloroethene (DDMU). This process will occur by reaction with either
Hp or Ha.
CHCIg
DDD
H90 HO
H
CI—^"~y~
-------
Part It 87
54. DDE
DDE will not hydrolyze to any reasonable extent; however, it may undergo other abiotic
transformation processes.
55. AP'-DDT
The reaction of p„p'-DDT occurs in a manner analogous to that previously described for
DDD. The reaction products resulting from dehydrochlorination are DDE and the mineral
acid.
c,-C)^h~0~c
DDT
HgO
HO
HC!
DDE
-------
88 Fate Constants lor Hazardous Waste Identification
56. Diallate
Diallate will hydrolyze by nucleophilic attack of and HO at the carbonyl group result-
ing in the formation of diisopropylamine and cis- and £rans-2,3-dichloro-2-propene-l-thiol.
(CH3)2CH
H—C—S—C H2-C=C H
(CH^CH ii ii
Diallate
HoO
HO
(CH3)2CH
N—H + HS"~H + 0=C=0
(CH3)2CH CI CI Carbon dioxide
Diisopropylamine cis- & trans -2,3-Dichloro-2-propene-1 -thiol
57. Dibenz[a,/i]anthracene
Dibenz[a,/t]anthracene will not hydrolyze. It has no hydrolyzable functional group.
Dibenzfa.hlarrthracene
-------
PartU 89
58. 1,2-Pibromo-3-chloropropane
1,2-Dibromo-3-chloropropane is subject to both neutral and base-mediated hydrolysis.
Neutral hydrolysis occurs initially by nucleophilic displacement of either chlorine or bro-
mine. Nucleophilic attack at the carbon bearing the chlorine results in the formation of 2,3-
dibromopropanol, which will react further to give 2,3-dihydroxybromopropane through the
intermediate epoxide, epibromohydrin. 2,3-Dihydroxybromopropane will undergo further
hydrolysis through the intermediate epoxide, l-hydroxy-2,3-propylene oxide, which reacts
with HjO to give glycerol. Nucleophilic displacement of bromine from l,2-dibromo-3-
chloropropane gives 2-bromo-3-chloropropanol, which will react further through epoxide
intermediates eventually to give glycerol, as described previously for the hydrolysis of 2,3-
dibromopropanol.
The base-mediated hydrolysis of l,2-dibromo-3-chloropropane will occur by dehydrohalo-
genation to give two initial products, 2-bromo-3-chloropropene and 2,3-dibromo-l-propene.
2-Bromo-3-chloropropene is expected to be the major reaction product because bromine is a
better leaving group than chlorine. Both products, however, will undergo facile hydrolysis
through formation of an allylic carbonium ion, which will react with H20 to give 2-bromo-3-
hydroxypropene. This product will be stable to further hydrolysis.
1,2-Dlbromo-3-ctioropropane
CH2-CH-CH2 ~ HBr HaC-C-CHa + H2C-C-<>
OH Br CI Br Br Br CI
2-Bromo-3-cttoropro parol 2,3-Dibromopropene
2,3-Dibromo-1-propanol
;H2-CH-^CH2 + HBr
EpicMorohydrin
Epibromohydrtn
2-Bromo-3-hydroxypfoper»
2-Brorno-3-chioropropene
HCl / + HBr
1 -Bromo-2,3-d!hyrinc»fypropane
1-Chtoro-2,3-dihydroxypropane
^a-Ct^CHs + HBr
1 -Hydroxy-2,3-propytene oxido
1 -H>droxy-2,3-propytene oxide
+ HCl
Glycerol
Glycerol
-------
90 Fate Constants tor Hazardous Waste Identification
59. Dibromomethane
Dibromomethane should not hydrolyze to any reasonable extent. QSAK model computa-
tions have indicated that the half-life of this halogenated methane is several thousand
years.
CH2Br2
Dibromomethane
60. 1,2-Dichforobenzene
1,2-Dichlorobenzene will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
1,2-Dichlorobenzene
-------
Part II 91
61. 1,4-Dichlorobenzene
1,4-Dichlorobenzene will not hydrolyze to any reasonable extent, however, it may undergo
other abiotic transformation processes.
1,4-DicNorobenzene
62. 3,3'-Dichlorobenzidine
3,3'-Dichlorobenzidine will not hydrolyze to any reasonable extent; however, it may un-
dergo other abiotic transformation processes.
3,3'-DicWorobenzidine
-------
92
Fate Constants for Hazardous Waste Identification
63. Dichlorodifluoromethane
Dichlorodifluoromethane has a negative boiling point and exists in a gaseous state at room
temperature. Its hydrolysis pathway has not been addressed.
CCI2F2
Dichlorodifluoromethane
64. 1,1 -Dichloroethane
The reaction of 1,1-dichloroethane occurs by both nucleophilic substitution and dehydro-
chlorination. The reaction products resulting from nucleophilic substitution by HjO and
HO" are acetaldehyde and HC1, whereas dehydrochlorination gives vinyl chloride and the
mineral acid.
Vj1
H—C=C—H
Vinyl chloride
CH3CHCI2
1,1-Dichloroethane
HoO
HO
f
H3C—C—H + HCI
Acetaldehyde
-------
Part II 93
65. 1,2-Dichloroethane
The reaction of 1,2-dichloroethane by H^O and HO" occurs by both nucleophilic substitution
and dehydrochlorination. Hydrolysis by nucleophilic substitution will lead to the formation
of 2-chloroethanol and HCI, whereas dehydrochlorination results in vinyl chloride and the
mineral acid. 2-Chloroethanol will react further producing ethylene oxide, which will hydro-
lyze by reaction with H20 to yield ethylene glycol.
aCHgCHjjCI
1,2-Dichloroethane
H20,H0/ \ H20, HO
CI H
H—C===C—H + HCI
Vinyl chloride
CI—CH2-CH2-OH + HCI
2-Chloroethanol
O
/\ +
H2C—CH2
Ethylene o)dde
HCI
HO-CH2-CH2-OH
Ethylene glycol
-------
94
Fate Constants for Hazardous Waste Identification
66. 1,1-Dichloroethylene
1,1-Dichloroethylene will not hydrolyze to any reasonable extent.
CI H
I I
CI—C=C—H
1,1 -Dichtoroeth^ene
67. c/s- 1,2-Dichloroethylene
cw-1,2-Dichloroethylene will not hydrolyze to any reasonable extent; however, it may
undergo other abiotic transformation processes.
CI CI
H—C=C—H
cis-1,2-DichloroettTylene
-------
Part 11 95
68. frans-1,2-Dichloroethylene
trans-l,2-Dichloroethylene will not hydrolyze to any reasonable extent; however, it may
undergo other abiotic transformation processes.
CI
!
H—c=C—H
I
CI
trans-1,2-Dichloroethylene
69. Dichloromethane
Hydrolysis of dichloromethane occurs by nucleophilic substitution with H20 (neutral hy-
drolysis) resulting in the displacement of chlorine with HO\ The resulting chlorohydrin is a
transient intermediate that immediately loses chlorine to yield formaldehyde, the final
hydrolysis product.
ChfeClz
Dichloromethane
H;>0
? + HCI
H—C-H
Formaldehyde
70. 2,4-Dichlorophenol
2,4-Dichlorophenol will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
OH
2,4-DicNorophenol
-------
96
Fate Constants for Hazardous Waste Identification
71. 1,2-Dichloropropane
The reaction of 1,2-dichloropropane with I^O or HO" will proceed through competing reac-
tion pathways (nucleophilic substitution and dehydrohalogenation). Nucleophilic substitu-
tion will occur at the primary carbon resulting in the formation of 2-chloropropanol. This
intermediate will degrade by intramolecular nucleophilic displacement of the chlorine atom
by the adjacent hydroxyl group resulting in the formation of propylene oxide. Propylene
oxide will undergo predominantly neutral hydrolysis to give 1,2-dihydroxypropane. Base-
mediated elimination of chlorine will result in the formation of 1-chloro-l-propene, which
will be stable to further hydrolysis.
H—CH
1,2-Dichloropropane
CI H
OH CI
+ HCI
h2<^—h—ch3 + HCI
1-CNoro-1-propene
2-CWoropropanol
H2C—-CH—CH3 + HCI
Propylene oxide
H-CH.
1,2-Dihydroxypropane
-------
Part II 97
72. 1,3-Dichloropropene
Hydrolysis of 1,3-dichloropropene will occur by reaction with HjO through nucleophilic
substitution resulting in the formation of 3-chloro-2-propene-l-ol. Because the
stereochemistry about the carbon-carbon double bond is not affected in this hydrolysis
reaction, the trans isomer of 1,3-dichloropropene will give the trans isomer of the allylic
alcohol and the cis isomer of 1,3-dichloropropenewill lead to the formation of the cis isomer
of the allylic alcohol.
hcci=ch-ch2ci
1,3-DicNoropropene
H
cis-1,3-Dichloropropene
C!
trans-1,3-Dichloropropene
OH H
H
cis-3-CNoro-2-propen-1 -ol
trans-3-Chloro-2-propen-1 -o!
-------
98 Fate Constants for Hazardous Waste Identification
73. Pieldrin
Hydrolysis of dieldrin will occur through nucleophilic substitution with H20 at the epoxide
moiety resulting in the formation of the diol. The diol will be stable to further hydrolysis.
C
Dieldrin
H20
C
Dieldrin diol
-------
Part II 99
74. Diethyl phthalate
The base-mediated hydrolysis of diethyl phthalate will initially result in formation of the
monoester, which will undergo further hydrolysis to o-phthalic acid. The hydrolysis of the
monoester will occur at a rate approximately half that of the parent compound.
aC 0 CH2CH3
|-o-ch2ch3
Diethyl phthalate
HO'
?
C-OH
c—o—ch2ch3
II 2 3
o
Ethyl hydrogen phthalate
+ CH3CH2-OH
Ethanol
afi-OH
+ CH3CH2-OH
f~°H
o
o-PhthaKc acid
Ethanol
-------
100
Fate Constants for Hazardous Waste Identification
75. Diethylstilbestrol
Diethylstilbestrol will not hydrolyze. It has no hydrolyzable functional group.
ch2ch3
H
H
Diethylstilbestrol
76. Dimethoate (opposite page)
Hydrolysis of dimethoate may occur through either reaction with H^O (neutral hydrolysis)
or reaction with HO- (base-mediated hydrolysis). Nucleophilic substitution by water can
occur at either the methylene carbon of the thio substituent, which gives 0,0-dimethyl-
phosphorodithioic acid and iV-methyl-2-hydroxyacetamide, or the carbon of the methoxy
substituent to give 0-methy 1-S-[2- (iV-methylacetamide) ]phosphorodithioic acid and metha-
nol. In either case, the diester that is formed will be much more persistent than the parent
compound. Because the diesters are ionized at pH 7, they are approximately a factor of 10
less reactive towards hydrolysis than the triesters. Hydrolysis of 0,0-dimethylphosphoro-
dithioic acid will occur through formation of the monoester, 0-methylphosphorodithioic
acid, which hydrolyzes further to eventually give phosphoric acid and hydrogen sulfide.
Likewise, hydrolysis of 0 -methyl-S- [2 - (N-methylacetamide) Iphosphorodithioic acid will
result in the formation of the monoester, O-methylphosphorodithioic acid, in addition to N-
methyl-2-hydroxyacetamide. Hydrolysis of the monoester, which occurs by nucleophilic
attack at the phosphorus atom, will proceed at a rate of approximately one half that of the
parent triester.
Base-mediated hydrolysis of dimethoate will occur by nucleophilic attack of HO at the
central phosphorus atom to give 0,0-dimethylphosphorothioic acid and iST-methyl-2-
mercaptoacetamide. Further hydrolysis of 0,0-dimethylphosphorothioic acid may occur as
previously described.
-------
Part II
CH30-P-S-CH2-C-NH-CH3
Dimethoate
H2O
CH30—P—SH + HO-CH2CNHCH3
icH:
B
I !
P-OH + HSCHoCh
CH3O-P-OH + HSCH2CNHCH3
1 vAcH3 j
CH3O—P—SH + CH3OH CH30—P—S—CH2CNHCH3 + CH3OH
c Ah
I
HO-P—SH + CH3OH
E OH D
H il
f f
P—S-CH0CNHCH0 +
H
CHgO-P-OH + CH3OH
k Ah D
? f
CH30—P—SH + HO—CH2CNHCH3 HO—P—OH + CH3OH
c Ah
B
l Ah
HO—P—SH
E Ah
O
HO-P-OH + HgS
F Ah G
A O,0-Dimethylphosphorodithioic acid
B N-Methyl-2-hyidroxyacetamide
C O-Methylphosphorodithioic acid
D Methanol
E Phosphorodithioic acid
F Phosphoric acid
G Hydrogen sulfide
H 0-Methyl-S-(2-(N-methyiacetamide))phosphorodithioic acid
I 0,0-Dimethyfphosphorothioic acid
J N-Methyf-2-mercaptoacetamide
K O-Methylphosphorothioic acid
L Phosphorothioic acid
HO-P-OH
p I
F OH
CHjOH
D
HgS
G
O
II
HO-P-OH
F Ah
h2s
G
-------
102 Fate Constants tor Hazardous Waste Identification
77. 3,3'-Dimethoxybenzldine
3,3'-Dimethoxybenzidine will not hydrolyze; however, it may undergo other abiotic transfor-
mation processes.
NH.
3,3'-Dimethoxybenzidine
78. 7,12-Dimethylbenz[a]anthracene
7,12-Dimethylbenz[a]anthracene will not hydrolyze. It has no hydrolyzable functional
group.
CH
7,12-Dimethylbenz(a]anthracene
-------
Part II 103
79. 3,3'-Dimethyibenzidine
3,3'-Dimethylbenzidine will not hydrolyze; however, it may undergo other abiotic
transformation processes.
CH
NH.
HaC
3,3'-Dimethylbenzi dine
80. 2,4-Dimethylphenol
2,4-Dimethylphenol will not hydrolyze. It has no hydrolyzable functional group.
CH
CH3
2,4-Dimethylphenol
-------
Fate Constants for Hazardous Waste Identification
81. Dimethyl phthalate
Dimethyl phthalate will hydrolyze by nucleophilic attack of HO' at the ester carbonyl group
resulting in methyl hydrogen phthalate and methanol, which can undergo further base-
mediated hydrolysis to o-phthalic acid.
^N^C-O-CHg
^^-o-CHa
O
Dimethyl phthalate
HO
a
o
d—OH
C_0_CH
H 3
o
+ ch3oh
Methyl hydrogen phthalate
O
II
C-OH
C-OH
II
O
Methanol
CH3OH
o-Phthaic acid
Methanol
-------
Part II
82. 1,3-Dinitrobenzene
1,3-Dinitrobenzene will not hydrolyze; however, it may undergo other abiotic transforma-
tion processes.
1,3-Dinitrobenzene
83. 2,4-Dinitrophenol
2,4-Dinitrophenol will not hydrolyze; however, it may undergo other abiotic transformation
processes.
no2
2,4-Dinitrophenol
-------
106 Fate Constants for Hazardous Waste Identification
84. 2,4-Dinitrotoluene
2,4-Dinitrotoluene will not hydrolyze; however, it may undergo other abiotic transformation
processes.
CH.
NO.
N02
2,4-Dinitrotoluene
85. 2,6-Dinitrotoluene
2,6-Dinitrotoluene will not hydrolyze; however, it may undergo other abiotic transformation
processes.
2,6-Dinitrotoluene
-------
Part II 107
86. Di-n-butyl phthalate
The reaction pathway for the hydrolysis of di-n-butyl phthalate is identical to that de-
scribed previously for dimethyl phthalate (#81).
S-O—
(CH2)3CH3
C-0-(CH2)3CH3
o
Di-rvbutyl phthalate
HO
aC-OH
,
CH3(CH2)3-OH
C-0-(CH2)3CH3
o
n-Butyl hydrogen phthalate
rvButanol
r^wc"0H
o-Phthalic acid
CH3(CH2)3-OH
rvButanol
-------
108 Fate Constants for Hazardous Waste Identification
87. Di-n-octyl phthalate
The reaction pathway for the hydrolysis of di-n-octyl phthalate is identical to that described
previously for dimethyl phthalate (#81).
0
II
C-0-CH2(CH2)6CH3
c-o-ch2(ch2)6ch3
0
Di-n-octyl phthalate
HO
C-OH
C-0-CH2(CH2)6CH3
O
n-Octyl hydrogen phthalate
HO(CH2)7CH3
n-Octanol
HO
a
C—OH
II
O
HO(CH2)7CH3
n-Octanol
o-Phthalic acid
-------
Part II
109
88. 1,4-Dioxane
1,4-Dioxane will not hydrolyze. It has no hydrolyzable functional group.
1,4-Dioxane
89. 2,3,7,8-TCDDioxin
2,3,7,8-TCDDioxin will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
cr ^ ^CT ^ XI
2,3,7,8-TCDDioxin
-------
Fate Constants for Hazardous Waste Identification
90. 2,3,7,8-PeCDDioxins
2,3,7,8-PeCDDioxins will not hydrolyze to any reasonable extent; however, they may
undergo other abiotic transformation processes.
C
c
91. 2,3,7,8-HxCDDioxins
2,3,7,8-HxCDDioxins will not hydrolyze to any reasonable extent; however, they may
undergo other abiotic transformation processes.
cr ^ "cr ^ xi
2,3,7,8-HxCDD
92. 2,3,7,8-H pCDD ioxi ns
2,3,7,8-HpCDDioxins will not hydrolyze to any reasonable extent; however, they may
undergo other abiotic transformation processes.
C
2,3,7,8-HpCDD
-------
Pari II 111
93. OCDD
OCDD will not hydrolyze to any reasonable extent; however, it may undergo other abiotic
transformation processes.
cr cr y xi
Ci ci
OCDD
94. Diphenylamine
Diphenylamine will not hydrolyze; however, it may undergo other abiotic transformation
processes.
Diphenylamine
95. 1,2-Diphenylhydrazine
1,2-Diphenylhydrazine will not hydrolyze; however, it may undergo other abiotic
transformation processes.
H H ,—,
1,2-Diphenylhydrazine
-------
Fate Constants for Hazardous Waste Identification
96. Disulfoton
The reaction pathways for the hydrolysis of disulfoton are quite similar to those already
discussed for the hydrolysis of dimethoate (#76). Neutral hydrolysis can occur at two sites
resulting in the formation of phosphorus diesters, which will hydrolyze through the phos-
phate monoester to eventually give phosphoric acid and hydrogen sulfide. As with di-
methoate, base-mediated hydrolysis will occur by nucleophilic attack of HO at the central
phosphorus atom resulting in 2-thioethylethylthioether and 0,0-diethylphosphorothioic
acid, which will hydrolyze further to phosphoric acid and hydrogen sulfide.
CHjCHj-O-I—S-CHgCH^S—CHgCHa
icH,CH,
Disulfoton
HzO,
ch3ch2
A
. —SH + HO—CH2CH2-S—CH2CH3
Ach2ch3 B
CH3CH2-O-P-OH
1 AcH2CH3
H,0
CH3CH20—P—SH + CHgCHaOH
C Ah d
CH3CH2-oJ—S-CHjCHj-S—CH2CH3
Ah H
HO-P-SH + CH3CH2OH
E Ah V
hs—c h2c h2-s—c h2ch3
J
CHgCHjO-P-OH + CH3CH2OH
Al
H
+ CHaCHaOH f
D HO-P-OH + CH3CH2OH
l Ah n
CH3CH20—P—SH + HO—CH2CH2-S—CH2CH3
C Ah b
HO—P—OH + HgS
F ^ G HO-P-SH + CHgCHaOH
E Ah d
A O.O-Diethylphosphoiodlthioic acid
B 2-Hydroxyethylethytthioether
C O-Ethylphosphorodithioic acid
D Ethanol
E PhosphoroditNoic acid HO—P—OH + H2S
F Phosphoric acid p qh Q
Q Hydrogen sulfide
H O-Ethyl-S-t(2-(ethyltNo)ethy0]phosphorodithioic acid
I 0,0-Diethylphosphorothioic acid
J 2-Thioethylethylthioether
K O-Ethylphosphorothioic acid
L Phosphorothioic acid
HO—OH + HZS
F Ah
-------
Part II
97. Endosulfan
Endosulfan, which is a mixture of the alpha (Endosulfan I) and beta (Endosulfan II) iso-
mers, will hydrolyze by nucleophilic attack of I^O or HO* at the sulfur atom resulting in the
alpha and beta isomers of endosulfan diol. The ratio of the alpha to the beta isomers of
endosulfan diol will reflect the ratio of Endosulfan I to Endosulfan II in the parent com-
pound.
alpha-Endosuifan
beta-Endosulfan
Endosulfan diol
-------
114 Fate Constants for Hazardous Waste Identification
98. Endrln
Hydrolysis of endrin will proceed by nucleophilic attack of HjO at the epoxide moiety result-
ing in the formation of endrin diol, which will be stable to further hydrolysis.
c
Endrin
H20
C
OH
OH
Endrin diol
-------
Part II 115
99. Epichlorohydrin
Hydrolysis of epichlorohydrin will occur initially by attack of HjO at the epoxide moiety
resulting in the formation of l-chloro-2,3-dihydroxypropane. Subsequently, loss of chlorine
will occur through the intramolecular attack of HO" on the adjacent carbon to give 1-hy-
droxy-2,3-propylene oxide, which will undergo further hydrolysis by attack of H20 at the
epoxide moiety to give glycerol.
O
H2C—chch2ci
Epichlorohydrin
H20, H+
1 -Chloro-2,3-dihydroxypropane
0H / \
I / \ +
h2c-ch—ch2
1 -Hydroxy-2,3-propylene oxide
HCI
Glycerol
-------
116 Fate Constants for Hazardous Waste Identification
100. 2-Ethoxyethanol
2-Ethoxyethanol will not hydrolyze. It has no hydrolyzable functional group.
ch3ch2-o-ch2ch2-oh
2-Ethoxyethanol
101. Ethyl acetate
Hydrolysis of ethyl acetate will occur by acyl-oxygen bond cleavage by HgO and acid cataly-
sis and base mediation resulting in the formation of acetic acid and ethanol.
V
ch3-c-o-ch2ch3
Ethyl acetate
H+, H20, HO"
CHg-C-OH +
Acetic acid
HOCH2CH3
Ethanol
-------
Part II 117
102. Ethylbenzene
Ethylbenzene will not hydrolyze. It has no hydrolyzable functional group.
Ethylbenzene
103. Ethyl ether
Ethyl ether will not hydrolyze. It has no hydrolyzable functional group.
CH3CH2—0—CH2CH3
Etfiyl ether
-------
Fate Constants for Hazardous Waste Identification
104. Ethyl methacrylate
Hydrolysis of ethyl methacrylate will occur by the base-mediated cleavage of the acyl-
oxygen bond resulting in methacrylic acid and ethanol.
H2C=C—A—O—C H;
ch3
Ethyl methacrylate
2CH3
HO
H2C=C—C—OH + HOCH2CH3
ch3
Methacrylic acid Ethanol
-------
Part II 119
105. Ethyl methanesulfonate
Hydrolysis of ethyl methanesulfonate will occur in a manner analogous to the hydrolysis of
carboxylic acid esters. Nucleophilic attack of H20 at the carbon results in the formation of
methylsulfonic acid and ethanol.
9
ch3-|-o-ch2ch3
o
Ethyl metbanesiifonate
HgO
CH3-|—OH +
MethyteutforHC acid
HOCH2CH3
Ethanol
-------
120
Fate Constants for Hazardous Waste Identification
106. Ethylene dibromide
The reaction of ethylene dibromide proceeds by either nucleophilic substitution or
dehydrohalogenation. Nucleophilic displacement of bromine by HjO results in 2-bromo-
ethanol, which will react further through the epoxide intermediate to yield ethylene glycol.
Dehydrohalogenation results in the formation of vinyl bromide, which will be stable to
further hydrolysis.
Br Br
I I
H2C-CH2
Ethylene dibromide
+ HBr
H2C=CH + HBr
Vinyl bromide
?r
H2C-CH2
2-Bromoethanol
O
/ \ + HBr
H2C CH2
Ethylene oxide
Ethylene glycol
-------
Pari II
107. Famphur
The reaction pathways for the hydrolysis of famphur are similar to the organophosphorous
esters previously discussed. Both base and neutral hydrolysis can occur by nucleophilic
attack at the phosphorus atom resulting in the formation of phosphorous diesters, which
will hydrolyze through the phosphate monoester eventually to result in phosphoric acid and
hydrogen sulfide, and p-(NJV- dimethylsulfamoyl)phenol.
CHjO g CHa
Famphu
• 0H,0H C^-0« * HC^-0-t
-------
122 Fate Constants tor Hazardous Waste Identification
108. Fluoranthene
Fluoranthene will not hydrolyze. It has no hydrolyzable functional group.
Fluoranthene
109. Fluorene
Fluorene will not hydrolyze. It has no hydrolyzable functional group.
Fluorene
-------
Part II 123
110. Formic acid
Formic acid will not hydrolyze. It has no hydrolyzable functional group.
II
H-C-OH
Formic acid
111. Furan
Furan will not hydrolyze. It has no hydrolyzable functional group.
A
Furan
-------
124 Fate Constants tor Hazardous Waste Identification
112. 2,3,7,8-TCDFuran
2,3,7,8-TCDFuran will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
2,3,7,8-TCDFu-an
113. 1,2,3,7,8-PeCDFuran
1,2,3,7,8-PeCDFuran will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
1,2,3,7,8-PeCDFuran
-------
Part II 125
114. 2,3,4,7,8-PeCPFuran
2,3,4,7,8-PeCDFuran will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
C!
2,3,4,7,8-PeCDFiran
115. 2,3,7,8-HxCDFurans
2,3,7,8-HxCDFurans will not hydrolyze to any reasonable extent; however, they may
undergo other abiotic transformation processes.
cr ~ ~ ci
2,3,7,8-HxCDFiran
-------
126 Fate Constants for Hazardous Waste Identification
116. 2,3,7,8-HpCDFurans
2,3,7,8-HpCDFurans will not hydrolyze to any reasonable extent; however, they may
undergo other abiotic transformation processes.
C
c
2,2,7,8-HpCDFuran
117. OCDF
OCDF will not hydrolyze to any reasonable extent; however, it may undergo other abiotic
transformation processes.
CI CI
OCDF
-------
Part II 127
118. Heptachlor
Hydrolysis of heptachlor will occur by nucleophilic substitution of H20 at the allylic-carbon-
bearing chlorine resulting in the formation of 1-hydroxychlordene, which will be stable to
further hydrolysis.
Heptachlor
H20
1f
1 -Hydroxychlordene
-------
Fate Constants for Hazardous Waste Identification
119. Heptachlor epoxide
Heptachlor epoxide will hydrolyze by nucleophilic attack of HaO at the epoxide moiety
resulting in heptachlor diol. Further hydrolysis of the diol can occur by nucleophilic substi-
tution of HjO at the chlorine-bearing carbon adjacent to the hydroxyl groups. The resulting
triol will be stable to further hydrolysis.
Heptachlor epoxide
HzO
OH
Heptachlor diol
+ HCI
Heptachlor triol
-------
Part II 129
120. Hexachlorobenzene
Hexachlorobenzene will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
Hexachlorobenzene
121. Hexachlorobutadiene
Hexachlorobutadiene will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
CI CI CI
ci—i=c—
-------
Fate Constants for Hazardous Waste Identification
122. alpha-HCH
The reaction of alpha-HCH occurs by frarcs-dehydrochlorination of the axial chlorines
resulting in the intermediate 1,3,4,5,6-pentachlorocyelohexene. This cylcohexene will react
further with either H20 or HO through sequential dehydrochlorination steps to give a
mixture of the regioisomers, 1,2,3-trichlorobenzene and 1,2,4-trichlorobenzene.
alpha-HCH
HoO
HO
HC!
H CI
1,3,4,5,6-Pertochlorocyclohexene
+ HCI
1,2,3-Trichlorobenzene
+ HCI
1,2,4-TricNorobenzene
-------
Part II
123. beta-HCH
6e/a-HCH will not hydrolyze to any reasonable extent (NLFG). The six equatorial chlorines
do not permit initial £rans-dehydrochlorination to yield the intermediate
pentachlorocyclohexene as occurs in the alpha- (#122.) and gamma-isomers (#132).
beta-HCH
-------
132
Fate Constants for Hazardous Waste Identification
124. Hexachlorocyclopentadiene
Hydrolysis of hexachlorocyclopentadiene results in the formation of 1,1-dihydroxy-
tetrachlorocylcopentadiene, which is an unstable product. Its degradation leads to the
formation of polymers.
Polymers
CI CI
Hexachlorocyclopentadiene 1,1 -Dihydroxytetrachlorocycloperrtadiene
125. Hexachloroethane
Hexachloroethane will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
CI
CI—(p—CI
CI CI
Hexachloroethane
-------
Part II 133
126. Hexachlorophene
Hexachlorophene will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
OH HO
CI
Hexachlorophene
127. lndeno[1,2,3-ccflpyrene
Indeno[l,2,3-cd]pyrene will not hydrolyze. It has no hydrolyzable functional group.
lndeno[1,2,3-cd]pyrene
-------
134 Fate Constants for Hazardous Waste Identification
128. Isobutyl alcohol
Isobutyl alcohol will not hydrolyze. It has no hydrolyzable functional group.
Qh3
ch3-ch—ch2-oh
isobutyl alcohol
129. Isophorone
Isophorone will not hydrolyze. It has no hydrolyzable functional group.
CH
Isophorone
-------
Part II
130. Kepone
Kepone will not hydrolyze to any reasonable extent; however, it may undergo other abiotic
transformation processes.
Kepone
132. gamma-HCH
The reaction pathway for the hydrolysis of gamma-HCH (lindane) is identical to that de-
scribed for alpha-HCH (#122).
gamma-HCH
HjO, HO"
1,3,4,5,6-PentacNorocyclohexene
/ \
CI
1,2,3-Trichtorobenzene 1,2,4-Tricrtorobenzene
-------
136
Fate Constants for Hazardous Waste Identification
134. Methacrylonitrile
Hydrolysis of methacrylonitrile will occur by the acid-catalyzed or base-mediated hydrolysis
of the nitrile moiety to give methacrylic acid and ammonia.
ch3
H2C=(!/—C""N
Methacrylonitrile
H+, HO
H2C=C—^—nh2
o
Methacryl amide
CH3
H2C=i—C—OH + NH3
&
Methacrylic acid
-------
Part It 137
135. Methanol
Methanol will not hydrolyze. It has no hydrolyzable functional group.
CH3OH
Methanol
136. Methoxychlor
The products formed during aqueous hydrolysis of methoxychlor are influenced by the pH of
the system. Above pH 10, 2,2-6is(p -methoxyphenyl)-1,1 -dichloroethylene (DMDE) is the
only reported product. Below pH 10 a second product, anisoin, is observed. Anisoin is the
major product formed by hydrolysis when the system is below pH 8; however, it is unstable
and will oxidize to anisil. Hydrolysis is not an important pathway in further degradation of
DMDE and anisil.
HaC
Methoxychlor
H20
H3cc>hO^-hO~QC h3 +
2£-Bls(p-methoxyphenyt)-1,1 -dlcrtoroethytene
HC!
Hal
H
Anisoin
Oxidation
HaCO—^
Ho
Anisil
-------
138 Fate Constants for Hazardous Waste Identification
137. 3-Methylcholanthrene
3-Methyleholanthrene will not hydrolyze. It has no hydrolyzable functional group.
Xjfiy
3-Methylcholanthrene
138. Methyl ethyl ketone
Methyl ethyl ketone will not hydrolyze. It has no hydrolyzable functional group.
O
II
CH3CH2-C—CH3
Methyl ethyl ketone
-------
Part II 139
139. Methyl isobutyl ketone
Methyl isobutyl ketone will not hydrolyze. It has no hydrolyzable functional group.
O
(CH3)2CHCH2-5-CH3
Methyl isobutyl ketone
140. Methyl methacrylate
Hydrolysis of methyl methaciylate proceeds through nucleophilic attack by HO" at the ester
carbonyl to yield methacrylic acid and methanol. The second order alkaline hydrolysis rate
constant and the corresponding calculated half-life are in the range of values reported for
esters of similar structure.
O
II
H2C=C—c—o—c h3
ch3
Methyl methacrylate
H2C=(j>
CH.
4
HO
'—OH
+ CHgOH
Methanol
Methacrylic acid
-------
Fate Constants for Hazardous Waste Identification ¦.
141. Methyl parathion
Hydrolysis of methyl parathion may occur through either reaction with I^O (neutral hy-
drolysis) or reaction with HO" (base-mediated hydrolysis). Nucleophilic substitution by
occurs in sequence at the two methoxy carbons to yield 0-methyl-0-(p-nitrophenyl)-
phosphorothioic acid (diester) and 0-(p-nitrophenyl)phosphorothioic acid (monoester),
respectively. Loss of the second methyl group from the disubstituted ester would be at a
rate approximately a factor of 10 less than the loss of the methyl group from the triester.
Hydrolysis of the monosubstituted ester [0-(p-nitrophenyl)phosphorothioic acid] would
proceed through cleavage of the P-0 bond at a rate of approximately one-half the rate of the
parent triester. Hydroxide-ion-mediated hydrolysis of methyl parathion proceeds through
initial attack of the hydroxide ion on the phosphorus atom with displacement of the p-
nitrophenylate ion. Loss of the two methyl groups from the 0,0-dimethylphosphorothioic
acid will proceed as described above. The phosphorothioic acid generated in each hydrolytic
pathway will eventually degrade to phosphoric acid and hydrogen sulfide.
h3c-
h3c-
Methyi parathion
Hp / \HO"
H,C-
N02
0-MethyM>(p-nitropheny))phosphorothioic acid O.O-Dimethylphosphorotttoic acid p-Nitrophenol
+ CH3OH
Methanol
HO„
HC
0-(p-Nltrophenyl)phosphorothioic acid
+ CH3OH
Methanol
HC\f
Phosphorothioic acid p-Mtrophenol
HO. II
>-OH + H2S
HO
O-Methytphosphorothlolc acid
+ HO—^ ^—N02
HOs.
I^p-oh
HO^
Phosphorothioic acid
. Hz
HO
Phosphoric acid
CH3OH
Methanol
CH3OH
Methanol
Phosphoric acid
-------
Part II 141
142. Naphthalene
Naphthalene will not hydrolyze. It has no hydrolyzable functional group.
Naphthalene
143. 2-Naphthylamine
2-Naphthylamine will not hydrolyze; however, it may undergo other abiotic transformation
processes.
CO"
2-Naphthylamine
-------
Fate Constants for Hazardous Waste Identification
145. Nitrobenzene
Nitrobenzene will not hydrolyze; however, it may undergo other abiotic transformation
processes.
NO-
Nitrobenzene
146. 2-Nitropropane
2-Nitropropane will not hydrolyze; however, it may undergo other abiotic transformation
processes.
no2
CH3-CH-CH3
2-Nitropropane
-------
Part II 143
147. AlNitroso-di-/>-butylamine
iV-Nitroso-di-n-butylamine will not hydrolyze; however, it may undergo other abiotic trans-
formation processes.
II
N
C H3 (C H2)3—N— (C H2>3C H3
N-Ni troso-di-n-butylami ne
148. W-Nitrosodiethylamine
iV-Nitrosodiethylamine will not hydrolyze; however, it may undergo other abiotic
transformation processes.
I
CH3CH2-N—CH2CH3
N-Nitrosodiethylamine
-------
144
Fate Constants for Hazardous Waste Identification
149. M-Nitrosodimethylamine
2V-Nitrosodimethylamine will not hydrolyze; however, it may undergo other abiotic
transformation processes.
I
CH3-N-CH3
N-Nitrosodimethylamine
150. Af-Nitrosodiphenylamine
iV-Nitrosodiphenylamine will not hydrolyze; however, it may undergo other abiotic transfor-
mation processes.
N-Nitrosodiphenylamine
-------
Part II 145
151. AE-Nitroso-di-/f-propylamine
iV-Nitroso-di-n-propylamine will not hydrolyze; however, it may undergo other abiotic
transformation processes.
0
II
N
1
CH3(CH2)2-N— (CH2)2CH3
N-Nitroso-di-n-propylamine
152. A/-N it roso methyl ethyl amine
JV-Nitrosomethylethylamine will not hydrolyze; however, it may undergo other abiotic
transformation processes.
N
I
CH3CH2-N—CHg
N-Nitrosomethylethylamine
-------
146 Fate Constants for Hazardous Waste Identification
153. /V-Nitrosopiperidine
iV-Nitrosopiperidine will not hydrolyze; however, it may undergo other abiotic transforma-
tion processes.
II
N
6
N-Nitrosopiperidine
154. M-Nitrosopyrrolidine
iV-Nitrosopyrrolidine will not hydrolyze; however, it may undergo other abiotic transforma-
tion processes.
N
A
N-NitrosopyrroHdi ne
-------
Part II 147
155. Octamethyl pyrophosphoramide
Hydrolysis of octamethyl pyrophosphoramide (OMPP) proceeds through cleavage of the P-
O-P bond. OMPP is stable to attack by the hydroxide ion and the neutral water molecule,
but is degraded under acidic conditions.
(H3C)2N^y_o_V/N
-------
148 Fate Constants for Hazardous Waste Identification
156. Parathion
Parathion is the ethyl analog of methyl parathion. The products formed and mechanisms of
hydrolysis parallel those of methyl parathion (#141) but hydrolysis proceeds at a slower
rate typical for triethyl phosphates compared to trimethyl phosphates.
CHjCHjOJ /-V
p_0—/ \—|
CH,CHoO \=/
Parathion
CH3CH201
/P-Q—^ y—N02 + CH3CH2OH
0-Ethyl-0-(p-nitrophenyDphosphorothioic acid
Ethanol
HO,
s \r~\
\ / N°2 + CH3CH2OH
0,0-
hc^>N°2
p-Nitrophenol
S
CH3CH0-O. II
+ 3 2 >-0H
CH3CH2—O
¦Diethylphosphorothioic acid
0-(p-Nitrophenyl)phosphorothioic acid Ethanol
HO^f
^P-OH
HO—/ N02
HO"^ \n—/
Phosphorothioic acid p-Nitrophenol
HoJ?
yP—OH + H2s
HO
Phosphoric acid
CH3CH20vI_oh + CH3ch20H
HC"
O-Ethylphosphorothioic acid Ethanol
HO. I
'S»
>-OH
HO
Phosphorothioic acid
CH3CH2OH
Ethanol
Ha II
>-0H + H2S
HO
Phosphoric acid
-------
Part II
157. Pentachlorobenzene
Pentachlorobenzene will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
158. Pentachloronitrobenzene
The previously reported hydrolysis rate constant for pentachloronitrobenzene (PCNB) in
reference 6 was based on disappearance kinetics without confirmation of hydrolysis prod-
ucts. For this report, the hydrolysis experiment was repeated in glasa-sealed ampules. No
disappearance of PCNB was observed after 33 days at pH 11 and 85°C. PCNB has, there-
fore, been designated as NLFG.
H
CI
Pentachlorobenzene
N02
CI
Pentachloronitrobenzene
-------
150
Fata Constants for Hazardous Waste Identification
159. Pentachlorophenol
Pentachlorophenol will not hydrolyze to any reasonable extent; however, it may undergo
other abiotic transformation processes.
Pentachlorophenol
160. Phenol
Phenol will not hydrolyze. It has no hydrolyzable functional group.
Phenol
161. Phenylenediamlne
The three isomers of phenylenediamine, ortho-, meta-, and para-, will not hydrolyze; how-
ever, they may undergo other abiotic transformation processes.
NH2
,NHj>
1,2-Phenytenediamine
-------
Part II
162. Phorate
Phorate, by virtue of having one less methylene group in the sulfide side chain, is an analog
of disulfoton. The products formed and mechanisms of hydrolysis parallel those of disulfot-
on. Phorate has a neutral hydrolysis rate of approximately 30 times that of disulfoton (#96).
CH3CH2OJ
P—S-C H2-S-C h2c h3
CHaCHgO
Phorate
CH3CH20jj
CH3CH2oJ
p-s-ch2-s-ch2ch3
-SH
H-SH + CH3CH2OH CH3CH20J
HO p Q|-|
O-Ethylphosphorodithioic acid Ethanol HO^
:P—SH + CH3CH2OH
HOs.1
O-Ethylphosphorothioic acid
PhosphoroditWoic acid Ethanol
HO'
:p-sh + ch3ch2oh
HoJ?
Phosphoric acid
HgS
Phosphorodithioic acid Ethanol
H0^P—OH + HZS
HO^
Phosphoric acid
+ CH3CH2OH
Ethanol
HOs.1
ho>-°h
Phosphorothioic acid
+CH3CH2OH
Ethanol
"4-0,
HO
H
HoS
Phosphoric acid
-------
152 Fate Constants for Hazardous Waste Identification
163. Phthalic anhydride
Phthalic anhydride hydrolyzes to o-phthalic acid in water. The hydrolysis occurs through
nucleophilic attack of H20 at a carbonyl carbon. The resulting ring opening yields o-
phthalic acid.
Phthalic anhydride
H20
i '
i—OH
C-OH
164. Polychlorinated biphenyls
Polychlorinated biphenyls will not hydrolyze to any reasonable extent.
n = 1 -5
Polychlorinated biphenyls
-------
Part II
153
165. Pronamide
The N- substituted amide bond in pronamide, formed by reaction of a carboxylic acid and
primary amine, is more resistant to hydrolysis than similar bonds formed with carboxylic
acids and alcohols such as the previously discussed acrylate and phthalate esters.
CH,
C—N H—C—C—C H
CH3
Pronamide
H+
HO
-OH
3,5-Dichlorobenzoic acid
CH,
I 3
H2N-C-C-CH
I
CH.
1,1 -Dimethyl-2-propynylamine
166. Pyrene
Pyrene will not hydrolyze. It has no hydrolyzable functional group.
Pyrene
-------
154 Fate Constants for Hazardous Waste Identification
167. Pyridine
Pyridine will not hydrolyze. It has no hydrolyzable functional group.
Pyridine
168. Safrole
Safrole will not hydrolyze. It has no hydrolyzable functional group.
Safrole
-------
Pari II
171. Strychnine
Strychnine will not hydrolyze to any reasonable extent.
Strychnine
172. Styrene
Styrene will not hydrolyze; however, it may undergo other abiotic transformation processes.
CH=CH2
6
Styrene
-------
Fate Constants for Hazardous Waste Identification
173. 1,2,4,5-Tetrachlorobenzene
1,2,4,5-Tetrachlorobenzene will not hydrolyze to any reasonable extent.
1,2,4,5-TetrachlorobenzBne
174. 1,1,1,2-Tetrachloroethane
The hydrolysis pathway for 1,1,1,2-tetrachloroethane will proceed through competing
pathways (nucleophilic substitution and dehydrohalogenation). Nucleophilic substitution
will occur at the monochlorfnated carbon with formation of trichloroethanol. Degradation of
trichloroethanol will continue to yield glycolic acid (hydroxyacetic acid). Base-mediated
elimination of chlorine from 1,1,1,2-tetrachloroethane will result in formation of 1,1,2-
trichloroethylene.
H Cl
1,1,1,2-Tetrachio roe thane
~ hc,
H CI
2,2,2-TrichloroBthanol
CI CI
h—i=
-------
Part II 157
175. 1,1,2,2-Tetrachloroethane
1,1,2,2-Tetrachloroethane hydrolyzes by the base-mediated elimination of chlorine to 1,1,2-
trichloroethylene. This quantitative conversion occurs in the pH range of 5-9.
CI CI
CI—C-C-CI
H H
1,1,2,2-Tetrachloroethane
HoO
HO
CI
CI—(p=C—CI + HCI
H
1,1,2-Trichloroethylene
176. Tetrachloroethylene
Tetrachloroethylene will not hydrolyze to any reasonable extent.
a
CI—C=C-CI
Tetrachloroethylene
-------
158 Fate Constants for Hazardous Waste Identification
177. 2,3,4,6-Tetrachlorophenol
2,3,4,6-Tetrachlorophenol will not hydrolyze to any reasonable extent; however, it may
undergo other abiotic transformation processes.
OH
CI
2,3,4,6-Tetrachlorophenol
-------
Part II 159
178. Tetraethyl dithiopyrophosphate
The P-O-P bond of tetraethyl dithiopyrophosphate is very labile to attack by hydroxide,
even at concentrations of hydroxide present below pH 7. The resulting 0,0-diethyl-
phosphorothioic acid is hydrolyzed to the final products phosphoric acid and ethanol by the
mechanisms discussed in the section on hydrolysis of phosphates.
j^OCH2CH3
ch3ch2o §
P—O—Pv
CH3CH20/ VOCH2CHa
Tetraethyl dithiopyrophosphate
HO
HoO
CH3CH20 f
P—OH
CH3CH20
0,0-Diethylphosphorothioic acid
CH3CH2Ov§
V—OH + CHaCHgOH
HO
O-Ethyiphosphorothioic acid Ethanol
HOs.
^P—OH + CH3CH2OH
HO 3 2
PhosphorotWoic acid
Ethanol
HO.?
/P—OH + H2S
HO 2
Phosphoric acid
-------
Fate Constants tor Hazardous Waste Identification
180. Toluene
Toluene will not hydrolyze. It has no hydrolyzable functional group.
Toluene
181. 2,4-Toluenediamine
2,4-Toluenediamine will not hydrolyze; however, it may undergo other abiotic transforma-
tion processes.
NH
NHg
2,4-Toluenediamine
-------
Part II
182. 2,6-Toluenediamine
2,6-Toluenediamine will not hydrolyze; however, it may undergo other abiotic transforma-
tion processes.
B
2,6-Toluenediamine
183. o-Toluidine
o-Toluidine will not hydrolyze; however, it may undergo other abiotic transformation pro-
cesses.
NB
o-Toluidine
-------
Fate Constants for Hazardous Waste Identification
184. p-Toluidlne
p-Toluidine will not hydrolyze; however, it may undergo other abiotic transformation
processes.
NH2
p-Toluidine
185. Toxaphene
Toxaphene is a complex but reproducible mixture of chlorinated camphene (67-69% chlorine
by weight). The mixture has been shown to contain at least 177 and up to 670 components.
The degradation rate was determined by monitoring the loss of chlorine with time during
hydrolysis rate studies.
CH.
CH.
Toxaphene
+ HCI
-------
Part II
186. Tribromomethane
Hydrolysis of tribromomethane occurs initially by proton abstraction followed by formation
of the carbene, which reacts with HO' to form carbon monoxide and the mineral acid.
H
Br——Br
Br
Tribromomethane
HoO
HO
CO + HBr
Carbon monoxide
187. 1,2,4-Trichlorobenzene
1,2,4-Trichlorobenzene will not hydrolyze to any reasonable extent; however, it may un-
dergo other abiotic transformation processes.
1,2,4-Trichlorobenzene
-------
Fate Constants for Hazardous Waste Identification
188. 1,1,1-Trichloroethane
Nucleophilic attack by H20 on the trichloro- substituted carbon yields acetic acid, while the
hydroxide-ion-mediated elimination product is 1,1-dichloroethylene. The ratio of these
products is pH dependent. Acetic acid is the major product at low values of pH, while the
amount of the hydroxide-ion-mediated elimination product, 1,1-dichloroethylene, increases
with increasing values of pH.
H CI
1,1,1-Trichloroethane
H20 HO
H O
II
+ HCI
I
H
Acetic acid
1,1-DicNoroethylene
-------
Part II 165
189. 1,1,2-Trichloroethane
Hydrolysis of 1,1,2-trichloroethane will yield the substitution product, chloroacetaldehyde,
and the base-mediated elimination product, 1,1-dichloroethylene. The most acidic hydrogen
(dichloro-substituted carbon) is lost during elimination of chlorine to form 1,1-dichloro-
ethylene rather than 1,2-dichloroethylene. The ratio of products will be determined by the
pH of the system.
H H
1,1,2-Trichloroethane
H20 HO"
H H
H CI
+ H—C=C—CI + HCI
H
Chloroacetaldehyde
1,1-Dichloroethylene
H H
+ HCI
H
Hydroxyacetaldehyde
-------
166
Fate Constants for Hazardous Waste Identification
190. Trichloroethylene
Trichloroethylene will not hydrolyze to any reasonable extent.
CI CI
h-A=c-ci
Trichloroethylene
191. Trlchlorofluoromethane
Trichlorofluoromethane will not hydrolyze to any reasonable extent based on other
polyhalogenated methanes.
F
CI—C-CI
Trichlorofluoromethane
-------
Part II 167
192. 2,4,5-Trichlorophenol
2,4,5-Trichlorophenol will not hydrolyze to any reasonable extent.
OH
C
2,4,5-Trichlorophenol
193. 2,4,6-Trichlorophenol
2,4,6-Trichlorophenol will not hydrolyze to any reasonable extent.
2,4,6-Trichlorophenol
-------
Fate Constants tor Hazardous Waste Identification
194. 2,4,5-Trichlorophenoxyacetic acid
2,4,5-Trichlorophenoxyacetic acid will not hydrolyze to any reasonable extent; however, it
may undergo other abiotic transformation processes.
O
II
Ho-C—OH
2,4,5-Trichlorophenoxyacetic acid
195. 2-(2,4,5-Trichlorophenoxy)propionicacid (Silvex)
Silvex will not hydrolyze to any reasonable extent; however, it may undergo other abiotic
transformation processes.
(Ch2)2-^--oh
2- (2,4,5-TricNorophenoxy)propionic acid
-------
Part II
196. 1,2,3-Trichloropropane
By analogy to l,2-dibromo-3-chloropropane (#58), the ultimate products of aqueous
degradation of 1,2,3,-trichloropropane are 2-chloro-3-hydroxy-l-propene and glycerol. The
route to the substitution product, glycerol, proceeds through intermediate haloalcohols and
halohydrins. The amount of the elimination product, 2-chloro-3-hydroxy-l-propene, will
increase with increase in hydroxide ion concentration.
H H H
1,2,3-Trichbropropane
HoO
CI CI OH
H—cp—H
H—(^—(^—(^—H
H H H
1 -Chtoro-2,3-dihydroxypropane
^HyHyH
H H H
Glycerol
H + HCI
?H A
H + HCI
H H H
1 -Hydroxy-2,3-propylene oxide
OH OH OH
H-C-C-C—H
H H H
Glycerol
-------
170
Fate Constants for Hazardous Waste Identification
197. 1,1,2-Trichloro-1,2,2-trifluoroethane
l,l,2-Trichloro-l,2,2-trifluoroethane will not hydrolyze to any reasonable extent; however,
it may undergo other abiotic transformation processes.
CCIF2CCI2F
1,1,2--Trichloro-1,2,2-trifluoroethane
198. 1,3,5-Trinitrobenzene
1,3,5-Trinitrobenzene will not hydrolyze; however, it may undergo other abiotic transforma-
tion processes.
NO.
NO-
sym-Tri nitrobenzene
-------
Part II
199. Tris{2,3-dibromopropyl)phosphate
Hydrolysis of £r is (2,3 -dibromopropyl)phosphate by nucleophilic attack of H20 on the C-0
bond or hydroxide ion attack on phosphorus will yield the same products. The 2,3-dibromo-
propanol can undergo hydroxide-ion-mediated elimination to yield 2-bromo-2-propen-l-ol or
intramolecular displacement of bromine by the adjacent hydroxyl group to form
epibromohydrin. The epibromohydrin is ultimately hydrolyzed to the final product, glycerol.
The 0,0-(2,3-dibromopropyl)phosphoric acid will hydrolyze further to yield phosphoric acid
and 2,3-dibromopropanol.
Br Br
iHjAHCHj—O 9 ?r f"
^P-O-CHjCHCHa
Tris£,3-«ibromopropyl) phosphtfe
HjO
IhjIhCHj—o9
?-OH
HO'
n
HCHj—O
+ h4?4-
H H H
0.0-(2,3-Dibramopropyl)phosphaiic acid 2,3-Dibromopropanol
ko
H Br Br
Br Br
CHj&HCHj—
^P—OH +
MU wuw
H H H
0-(2,3-Dlbromcpropyf)phosphDric acid 2,3-Dibromopropanol
ko
^-OH
HO.
HO'
Phosphoric acid
H H H
2,3-Dibromopropanol
HjO
L . H„
ft H H
Epibromohydrin
O ™
"-fri
H Br Br
HO-1-ol
HBr
HO-4-i-i-OH + HBr
H H H
2-Bromo-1,3-propanadiol
jn
H—c—c—c—
H H "
"3-dihy
A
H OH OH
H H H
1 - Bromo-2,3-d«hydro*ypropanB
OH OH OH
HO—C—G—C—H +
HBr
H H H
Glycerol
H H H
Glycerol
0
-------
172
Fate Constants for Hazardous Waste Identification
201. Vinyl chloride
Vinyl chloride will not hydrolyze to any reasonable extent; however, it may undergo other
abiotic transformation processes.
H H
I I
H—C=C—CI
Vinyl chloride
202. Xylenes
The three isomers of xylene will not hydrolyze. They have no hydrolyzable functional group.
CHo
CH,
o-Xylene
m-Xylene
p-Xylene
------- |