Docket No. A-92-55
Item No. I-A-93
ff A)//o %?
FINAL REPORT
on
A LITERATURE REVIEW OF ATMOSPHERIC TRANSFORMATION
PRODUCTS OF CLEAN AIR ACT
TITLE m HAZARDOUS AIR POLLUTANTS
by
Chester W. Spicer, Albert J. Pollack,
Thomas J. Kelly, and Mukund Ramamurthi
Battelle
Columbus, Ohio 43201-2693
to
U.S. Environmental Protection Agency
Research Triangle Park, North Carolina 27711
U.S. EPA Contract No. 68-D80082
July 1993
-------
The information in this document has been funded wholly or in part
by the United States Environmental Protection Agency under
Contract No. 68-D80082 to Battelle. It has been subjected to the
Agency's peer and administrative review, and it has been approved
for publication as an EPA document. Mention of trade names or
commercial products does not constitute endorsement or
recommendation for use.
11
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TABLE OF CONTENTS
Page
INTRODUCTION 1
METHODOLOGY 2
Literature Surveyed 2
Search Strategy 2
Kinetics Data Base 4
Lifetime/Persistence Estimates 4
RESULTS 7
DISCUSSION 7
Overview 7
Reaction Products 13
Removal Processes and Lifetimes 13
Other Atmospheric Transformations 17
CONCLUSIONS AND RECOMMENDATIONS 18
REFERENCES ' 23
APPENDIX A. Summary of Hazardous Air Pollutant
Transformations 24
iii
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TABLE OF CONTENTS
(Continued)
Ea&g
Figures
Figure 1. Typical results from on-line literature search 3
Figure 2. Typical ABIOTIK, report identifying rate constants for
selected reaction processes 5
Figure 3. Example entry from the data summary in Appendix A 8
Tables
Table 1. Overview of the HAPs transformation data survey 9
Table 2. Data completeness by compound class 14
Table 3. Atmospheric lifetimes of HAP compounds (in days) 16
Table 4. Recommended highest priority chemicals for
transformation product studies 22
iv
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FINAL REPORT
on
A LITERATURE REVIEW OF ATMOSPHERIC TRANSFORMATION
PRODUCTS OF CLEAN AIR ACT
TITLE m HAZARDOUS AIR POLLUTANTS
by
Chester W. Spicer, Albert J. Pollack,
Thomas J. Kelly, and Mukund Ramamurthi
to
U.S. Environmental Protection Agency
U.S. EPA Contract No. 68-D80082
May 1993
INTRODUCTION
The presence of toxic contaminants in ambient air has been recognized as
a potential health concern for many years. To accelerate the pace of identifying and
regulating air contaminants, Congress established a list of 189 chemicals designated as
Hazardous Air Pollutants (HAPs) in the 1990 Clean Air Act Amendments (CAAA).
The 189 HAPs are a diverse group, including volatile organic compounds (VOCs),
pesticides, semivolatile compounds, and metals.
In addition to the concern of human exposure to these 189 chemicals, the
CAAA also identifies the need for "consideration of atmospheric transformation and
other factors which can elevate public health risks from such pollutants." Atmospheric
transformations of hazardous pollutants could result in products of higher or lower
1
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human health risk. A first step in ascertaining the effect of atmospheric transformations
of HAPs on human health involves determining the nature of the transformation
products. The reactions and products of some HAPs have been widely investigated, but
information on the transformations of most HAPs is scarce or nonexistent. The
purpose of this survey was to review and summarize the available literature on HAP
transformation products. Where possible, we also have summarized information on the
atmospheric lifetime of each HAP and the major processes affecting the lifetime.
METHODOLOGY
Literature Surveyed
For purposes of this survey, the 189 diverse chemicals designated as
HAPs were organized into chemical classes to facilitate searching for transformation
data. Information on the transformation products of the 189 HAPs was located using a
computerized database and through a general review of articles, reference books,
proceedings of relevant conferences, and unpublished reports.
We identified relevant literature through a keyword search of the
computerized databases of STN International (Columbus, Ohio). The databases
searched included the Chemical Abstract (CA) files from 1967 to present, Chemical
Abstract Previews (CAP) current files, and the National Technical Information Service
(NTIS) files from 1964 to present. All searches were conducted between November
1992 and January 1993.
Search Strategy
The search strategy targeted keywords such as "atmospheric or air,"
"reactions or kinetics or removal," and "rates or constants or lifetime." The search
was restricted to English language citations. The strategy used both Abstract and Basic
Index searches to increase the likelihood of finding relevant material. Figure 1 shows
an example of the actual on-line search strategy used.
2
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L1 (370205ISEA FILE-CA (ATMOS? OR AWI/AB.BI
L2 ( 1091«2)SEA FILE-CA 11 AND (REACT? OR KMET? OR REMOV?)/AB,BI
L3 ( 26394)S£A FILE-CA L2 AND (RATE? OR CONST? OR UFE?)/AB,BI
L4 ( 16985)SEA FILE-CA L3 AND BtQ/lA
LB ( 13717(SEA FILE-CA L4 NOT (SOIL? OR MANUF? OR SYNTH? OR FORIF?!/
L6 ( 11111)SEA FILE-CAL8 NOT (WASTE? OR BIOL? OR ENZYM? OR BACT7J/A
L7 ( 10527ISEA FILE-CA LB NOT (TOXICOL? OR SEPARATION OR COMPLEX?)/A
LB ( 102061SEA FILE-CA L7 NOT ELECTRODE7/AB.BI
LB ( B552)SEA FILE-CA LB NOT (GRAFT? OR COATBiO? OR REDOX? OR POLYM
L10 ( B617)SEA FILE-CA LB NOT SOLVB S L24 AND (DNfTRO AND CRESOL OR 534-52-1 )/AB,BI
3266 DMfTRO/AB
3021 DmrTRO/BI
14397 CRESOUAB
9056 CRESOUBI
278 534-52-1/AB
909 534-52-1 /Bf
L25 1 L26 AND (DMITRO AND CRESOL OR 534-52-1 l/AB.BI
- > DIS L26 1 TUU,SO,PY.AN
L44 ANSWER 1 OF 1 COPYRIGHT 1B82 ACS
T1 •**Atmotph«rtc#*# ##*rMctions##* of o-crMoi: gu phas* and Mrosoi products
AU Gro^Mn, D«W
SO Atmot. Environ., 18(8), 1B41-B2
PY 1984
AN CA101 (20):176631s
Figure 1. Typical Results from On-Line Literature Search
3
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Using the search strategy described above, master sets of citations were
set up in each of the STN files researched. These master sets were then combined with
the chemical names and CAS registry numbers to produce citation listings for specific
HAP compounds. The listed citations were then reviewed by title, abstract, and in
their entirety if the initial reviews indicated information of value.
Kinetics Data Base
Another resource used to uncover transformation information is the
computer database, ABIOTTK, (1). This database was developed to provide the
measured reaction rate constants for the abiotic degradation of organic compounds in
the atmosphere. Upon entering either the compound name or its CAS number, a
display is generated identifying published rate constants for several possible atmospheric
reactions for that chemical. A typical output is shown in Figure 2. This
database also provides literature citations for the rate data. In this study, the rate data
were used to estimate lifetimes and identify significant transformation processes, and
the cited literature was reviewed to identify reaction product information.
Lifetime/Persistence Estimates
To assess the impact of atmospheric transformations of HAPs on the risk
to human health, it is important to know the products of the transformations, and also
whether the rate of the reaction is fast enough to remove the hazardous chemical or to
cause the build up of hazardous levels of the products. Therefore, we searched for
information on the lifetimes of the HAPs, and the atmospheric processes that control
the lifetimes. For many of the HAPs, the lifetime is likely to be controlled by reaction
with hydroxyl radical, while for others, reaction with ozone, photolysis, or wet or dry
deposition processes, may control or at least influence the lifetime. Information on the
kinetics of atmospheric reactions has enabled us to list the primary removal processes
expected to control the lifetimes of many of the HAPs, and to estimate the lifetimes.
The lifetimes have been listed in our data summary within three broad ranges:
4
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4/16/93 1:52 PM
11:31:33 93.04.16
FASTSEARCH FOR CAS-NUMBERS
+ +
No. :000015 Lit. Com.: Z0015 CAS :71-43-2
NAME :Benzene
STRUCTURE:CH"CH-CH«CH-CH«CH SUM :C6H6
STRUC+-+ :+ +
kOH [con/s:] : 1.4 E-12 kN03 [can/#] :< 3. E-17
STATUS :R STATUS :R
LITERATURE:9 LITERATURE:8
k03 [can/5] : 7. E-23 k* :
STATUS :S STATUS :
"ITERATURE: 4,2 4 LITERATURE:
: STATUS : LITERATURE:
STATUS: (R)ecommended, (A)verage, (S)ingle,(E)stimate
¦* — — — +
! CAS-SEEK (+)PgDn (-)PgUp PRINT QUIT MASTER !
! SELECT WITH ARROW-KEYS OR FIRST LETTER !
+ +
Figure 2. Typical ABIOTDC, Report Identifying Rate Constants for Selected
Reaction Processes
5
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Less than one day
One to five days
Greater than five days.
These estimates are meant to provide the reader with a sense of the residence times of
these species in the atmosphere. The three broad categories represent rapidly
transformed/removed (r < 1 day), moderately persistent (r « 1-5 days), and highly
persistent (r > 5 days) species. The lifetime, r, is an exponential lifetime, or "e-
folding time", representing the time it takes for the mass of the HAP to decrease to 1/e
of its original value.
In some instances, estimates of the atmospheric lifetime of the target
chemicals have been reported in the literature. In other cases, we used reported rate
constants to identify the most important removal processes and to calculate a
corresponding lifetime. For those cases, we used the following reactant concentrations
in the calculations, to represent long-term average concentrations in a relatively polluted
atmosphere:
Reactant
Concentration
(molecules-cm3)
o3
1.5 x 10,:
OH
3.0 x 106
NOj
2.5 x 109
| HOj
1.0 x 109
Measured rate constants were not available for all of the pertinent reactions. When we
could not find an experimentally measured rate constant, we used published rate
estimates based on molecular structure. These cases are identified with an asterisk in
our data summaries.
In some instances, there was disagreement among rate constants and/or
lifetimes for a selected HAP from multiple references. In these cases, we have listed a
range of lifetimes.
6
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results
The results of this survey of HAP transformation products are compiled
in a 33-page table with an associated list o£ai^4 40" citations to relevant literature.
The full data table and reference list are included in this report as Appendix A. The
data table lists all 189 HAPs in the same order as in the CAAA. An example entry, for
toluene, is shown in Figure 3. The table lists the name and CAS number of each
compound, the chemical formula/structure, the major removal processes (in order of
importance when multiple processes are cited), the atmospheric lifetime, the reported
transformation products, references for the reported data, and any additional comments
or notes. As seen in the example, toluene is one of the chemicals for which there is a
substantial body of information. The transformation products are not listed in any
particular order. Many of the references report qualitative information only, so we
have not attempted to rank the products by abundance.
DISCUSSION
Qvgrvfcw
A summary of the data in Appendix A is given in Table 1. This table
lists the chemical name, the CAS number, the primary removal pathway, and the
atmospheric lifetime. Table 1 also notes whether transformation products are reported
and it assigns each species to one of ten compound classes for subsequent summaries.
The absence of an entry indicates that no information was found during the survey.
A review of Table 1 shows that 81 of the 189 HAP compounds have at
least partial information on removal processes, lifetimes, and documented
transformation products. Thirteen additional compounds were identified as being
unlikely to undergo any significant chemical transformation. Eighty-four compounds
had reaction rate and lifetime data but no identified transformation products. We found
no relevant information on either atmospheric kinetics or products for the remaining 11
compounds. It should be noted that transformation products have been reported for 81
7
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Compound and
| CAS Number
Chemical
Formula/Structure
fttyor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes
H Toluene
1 108-88-3
CHa
6
OH
1 to 5
Benzaldehyde, nitrotolueoe,
o.m.p-cresols, nitrocrcsols,
methyl nitrate, methyl glyoxal,
PAN, formaldehyde, benzyl-
nitrate, acetaldehyde, glyoxal,
dicarbonyls, benzoic acid, 2-
butenoic acid, Z-butenal, acetic
acid, butenedial, 4-oxo-2-
pentenal, 4-oxo-2-buteuoic acid,
4-oxo-2-pentenoic acid
4,5,6,7,9,14,17,
19.21,35,52,54,
55,65,102,110,
138,140,141
Figure 3. Example Entry from the Data Summary in Appendix A
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TABLE 1. OVERVIEW OF THE HAPs TRANSFORMATION DATA SURVEY
Compound
CAS
Mqjor Ramoval
Atmoapharic
Transformation
Compound
Rpgiftry No.
ProcMt
Ufatlma (daya)
Products
Claaa*
AcataMahyda
7547-0
OH
<1
Yaa
F
Aoatamtfa
flQ-36-g
OH
<1
E
AcatonitrMa
75-06-8
OH
>5
E
Acetoohenone
96-86-2
OH
1*d5
F
2-Aetty(aininoAuar«n«
83 963
OH
<1
E
Acroiain
107424
OH
<1
Yaa
F
AcryvTvoQ
7M6-1
E
Acryficacid
79-10-7
OH
<1
F
Auyuiin
107-13-1
OH
14 to >5
Yaa
E
AM
10746-1
OH
<1
Yaa
B
4-A»nino6iphany1
82-67-1
OH
«1
E
AnSrm
62-53-3
OH
<1
Yaa
E
o-Arwdm*
90444
OH
<1
E
Aabaaioa
1332-21-4
DapoaMon
>5
l|nn,
PVQnt
H
Dintint
71-43-2
OH
>5
Yaa
C
Btr&dim
82-87-5
OH
<1
E
Banzotrithionda
9647-7
OH
>5
D
Brayl chlondt
100-44-7
OH
1-5 to >5
Yaa
0
Biphanyl
82-52-4
OH
1 to5
Yaa
C
Ba (2-athylhaxyl) phthaiata (DEHP)
117-81-7
OH
<1
I
Bit (ehioroniathyl) athar
S4248-1
Watar
<1 to 1-5
Yaa
F
Bremoform
75-25-2
B
1,3-Butadiana
106-99-0
OH
<1
Yaa
A
Calevn cyanamida
156-62-7
OH
«1
H
CipnlKlim
106-60-2
F
Captan
133-06-2
OH
«1
G
Carbaryl
63-25-2
OH
<1
C
Carbon dfcutfida
75-1 SO
OH
14 to >5
Yaa
H
Carbon tatrachiorida
56-23-5
Phototyaia
>5
Nona
B
Cartxmyf auffide
463-56-1
OH
>5
Yaa
F
Catachot
12M0-9
OH
<1
C
- '
wrarwnotn
133-90-4
G
CNordana
57-74-9
OH
<1
G
CNorina
7782-50-5
Phototyaia
<1
Yaa
H
CNoroaosbe icid
79-11-8
OH
>5
F
532-27-4
OH
>5
F
CNofobiwoi
106-90-7
OH
>5
Yaa
0
CNoroteroftatt
510-15-6
OH
<1
G
wrwonn
6746-3
OH
>5
Yaa
B
CNoromathyt mathyl athar
107-30-2
Watar
<11014
Yaa
F
CMoreprana
126-994
OH
<1
Yaa
B
Craaote/Craayfcaeid
1319-77-3
OH
<1
Yaa
C
o-Craad
96-48-7
OH
<1
Yaa
c
nvCiaaol
106-39-4
OH
<1
Yaa
c
P-Craaei
106-44-5
OH
<1
Yaa
c
Cumana
96-824
OH
<1
c
2,4-D, Bats & aatara
•4-75-7
OH
<1
Yaa
G
DOE
72-56-9
Phototyaia
<1
G
9
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Table 1. (Continued)
Compound
CAS
M^jor Ramoval
Atmoapharic
Transformation
Compound
Registry No.
Procosa
Ufttlma (days)
Products
Class*
Diezomethene
TM M 3
Ossna
<1
E
Dfearoofmn
13244-9
OH
<1
F
154)fcmmo*cNaiaereeene
96-12-8
OH
>5
Yaa
B
DfcuMuWuWi
84.74.2
OH
<1
I
| A *¦
i.^ucnwww
108-46-7
OH
>5
Yaa
D
j.^vCiMwipBnnv
B144-1
0|y^|ik^jA
nwyw
<1
E
Oichtoreatfiyt athar
111-44-4
OH
1to5
F
1.3-DieNorcerapana
542-75-6
OH
<1
Yaa
B
Dct#rvo*
82-73-7
OH
<1
G
DtrthinolHwii
111-42-2
OH
<1
E
N.N-Omsthvtarina
121-80-7
OH
<1
Yaa
E
Diathyl sulfate
6447-5
Water
<1
Yaa
J
3,3"-Dimalfi«yban8dina
119-904
OH
<1
E
DimafbyiananQtzobanzana
80-11-7
OH
<1
E
3.3'-Pimathyfeanzidina
119-93-7
OH
<1
E
uwnnnycefBBH®yi uww
7*44-7
OH
<1
E
N.N-Oimathyffonnamida
86-12-2
E
1,1-0imstfcy< hydrizina
87-14-7
OH
<1
Yaa
E
Dimathyt pfthalala
131-11-3
OH
1 to 5
I
Dimethyl aulfata
77-78-1
Wat*
<1
Yaa
J
4,6-Dinilr©*5
E
2,4-Dinitrophanol
51-28-5
OH
>5
E
2.4-Owtrotokjant
121-14-2
Phctdyaia
1 to 5
E
1.4-Onocana
123-91-1
OH
1 to 5
F
1.2-Oiphanyfiy**zina
122-66-7
OH
<1
E
EpieNorehydrin
1064M
OH
>5
Yaa
F
1,2-EpooiybUane
10646-7
OH
1 to 5
F
Ethyl acrytat#
140-86-5
Ozena
1 to 5
Yaa
F
Eftyfeanzana
100-41-4
OH
<1
Yaa
C
Ethyl caitwnat*
51-79-6
OH
«1
E
Ethyl chtorida
7VOO-3
OH
>5
B
j£|Mgy|u4A
ttnyw onvnoi
106-83-4
OH
>5
Yaa
B
Ethytana dfchtorida
107-06-2
OH
>5
Yaa
B
Ethylana glyool
107-21-1
OH
1 to5
F
cinyinpnvi
151-86-4
OH
<1101-5
E
Ethytana ooda
75-21-8
OH
>5
Yaa
F
Ethytana thiouw
96-45-7
E
tnyiOW wnDrlll
7S34-3
OH
1to5
B
romviinvQv
soooo
mototywa
<1
Yaa
F
it, ,k i,,
nCPwwvwi
76-44-6
OH
<1
G
Haxachlomfaaniana
116-74-1
OH
>5
D
8748-3
OH
>5
B
Hattchtoracydopantadtana
77-47-4
OH
<1
Yaa
B
Hamrhtorpalhsna
87.72-1
OH
>5
B
Ha»ma«hytana-1,&dwoeyanata
822-06-0
E
n#iwiiPhyipiiutpooraTlio*
68031-9
E
Haxana
110-54-3
OH
<1
Yaa
A
Hyfrsina
302-01-2
OH
<1
E
10
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Table 1. (Continued)
Compound
CAS
Raglatry No.
Major RamovaJ
Proeoaa
Atmoapharic
Ufatima (day*)
Transformation
P rod u eta
Compound
Claaa *
nyuuuvonc ioo
T647-014
Oapoafeon
1 to5
Yaa
H
nyngsn nounov
7664 363
Dapoatton
1 to5
Yaa
H
Hy*equinona
123-31-8
OH
1to6
F
lacphoraoa
7646-1
OH
<1
F
Lindana (al iaomara)
SUM
OH
<1
Yaa
0
wwc vnyra
106-31-6
OH
<1
Yaa
F
M9hW
6746-1
OH
1 te5
Yaa
F
72-4«
OH
<1
0
KJ^Akyl
RMmyi uuum
7443-9
OH
>5
Yaa
6
Mtfhyl chlorida
7447-3
OH
>5
Yaa
6
71466
OH
>5
Yaa
6
Molhyl attvrf katona
76-9M
Hh ^¦ I i •.
rnOOyM
<1
Yaa
F
Msthyttydrcina
6M44
OH
<1
E
Mathyf iodida
74464
OH
>5
Yaa
6
Mathyl iaefcutyl katona
106-10-1
OH
1 to5
Yaa
F
Matbyf iaocyanata
62443-9
OH
<1
E
Mtfhyt mathaerytata
60424
OH
<1 to 14
Yaa
F
Mathyttart-buMalhar
1634444
OH
1 to5
Yaa
F
4.4'-M«thy(anabia(2-cNoro«iKn*)
101-144
OH
<1
E
Mathylana ehlorida
7W6-2
OH
>5
Yaa
6
Mfltfiytanadphsnyt dMoevanata
101464
OH
<1
E
4.4,-M*hyl«na£an»na
101-77-9
OH
<1
E
NapNhatona
91-20-3
OH
<1
Yaa
C
NireNnnm
96-96-3
OH
>5
Yaa
E
4-Nlrebiphany<
92-934
OH
14 to >5
E
A lf« ¦ r1- '
Mwopninoi
100-02-7
OH
14 to >5
E
2-Ntoopropan*
79-46-9
OH
<1
Yaa
E
N-Ntooao-N-matfiyluraa
664-934
OH
<1
Yaa
E
N-Nitraaod>natfiytarnina
62-75-9
Photofyw
«1
Yaa
E
N-Nitroaornorphoina
6649-2
OH
<1
Yaa
E
Parathion
96-36-2
OH
<1
Yaa
G
Panlachtaunttotoaraana
62464
OH
>6
E
Partachtaophanol
67464
OH
>5
F
Bka^l
rnpM
106-96-2
OH
<1
Yaa
F
^Phmyimidwnjni
106404
OH
<1
E
75-44-5
Wrtar
1lo 5
Yaa
F
rnepnme
760341-2
OH
<1
Yaa
H
PhOI^0VJI
7723-144
0*»an
<1
Yaa
H
rmK ¦nyuw
6644-9
OH
>5
1
PotycNorinatad bfehanyti
1336464
OH
>8
Yaa
D
1.3-Prapanaaufeona
1120-71-4
OH
1 to5
F
bata-Prapioiactena
67474
OH
>5
F
PiCKNunaldahyda
129464
OH
1 to 5
F
Propowr
114-26-1
OH
<1
O
Propyfana dcNonda
76474
OH
>5
6
Prcpytona soda
7546-9
OH
>6
Yaa
F
1,2*PfopylMiNna
75466
OH
<1
E
11
-------
Compound
CAS
Major Ramoval
Atmoapharic
Transformation
Compound
Raalatry No.
Procaas
Ufatlma (days)
Products
Clsss *
QUnotna
91-22-5
OH
1 to5
E
Qianen*
10W1-4
OH
>6
F
Styrana
10042-6
OH
<1
Yaa
C
Styrana anda
66093
OH
1 Id 6
F
2.3.7.6-Ta5
6
»- ^— - *-» —«
iiriGnBreisww
127-1M
OH
>5
Yaa
6
Itanium tatraeNorida
7960454
H
ToJuana
10646-3
OH
1 to5
Yaa
C
2,4-To*janad«mina
9M0-7
OH
<1
E
2.4-Toiuana daocvanata
66444-9
OH
<1
Yaa
E
oToiuidm
96-53-4
OH
<1
E
Tosplwn
6001-36-2
DapoiJbon
>6
6
1,2.4-TricNorcfearaana
120-82-1
OH
>5
. 0
1.1.2-TricNoroa«hana
7W&5
OH
>6
B
*-¦ - '
incnpDKnyRni
7M14
OH
>5
Yaa
6
n j a •-•-«-» *- ¦
1 nCnwvPWiQI
66-96-4
OH
>5
F
68-06-2
OH
>5
F
Triathytamina
121-444
E
Trifluraiin
1562-0M
OH
<1
Yaa
6
Z2,4-Trimalhyteartana
640-64-1
OH
1 to 5
Yaa
A
Vinyf acatata
106-05-4
OH
<1
F
Vflyl UUIM
503-60-2
OH
<1 to 1-5
B
Mnylehiorida
75-01-4
OH
<1to 1-5
Yaa
B
wiymnv craonov
7S36-4
OH
<1
Yaa
B
Xyianaa (iaomare & mfaduras)
133-02-07
OH
<1
Yaa
C
o-Xyterw
96-47-6
OH
<1
Yaa
C
m-Xytone
106-36-3
OH
<1
Yaa
c
»>Xy5
Nona
H
Araanic conwrdi
Dtpotition
>5
wont
H
Baryftum confounds
Dapoaibon
>5
nono
H
Cadmium eompeunda
Deposition
>5
non®
H
Chromium oompounda
Dopooltion
>5
nont
H
CcM compound#
Dopottton
>5
—
mm
H
Cote owan amiaaiona
c
Cyanida oompounda
OH
>8
H
Oyeotattws
OH
<1
F
laad compound#
Owoaten
»6
nono
H
Mmoamu eonpoundi
Dapoation
>5
Nona
H
Mvttfy oompomdi
• •
>5
Yaa
H
Mnaral ffeara (km)
Deposition
>5
nono
H
Mcfcai oompoinda
Dapoation
>6
fwn|
H
Potycyie ofiw mattar
OH
<1 to 1-5
Yaa
C
RadtonucSdaaGndudna Radon)
Daeay
1 to5
Yaa
H
Sdmmi compound#
Dapoaibon
>5
nono
H
* Compound Classas: <
A; Hydrocarbon*
B: Haioganatad Hydrocarbons
C: Aromatic Compounds
0; Haioganatad Aromatics
E Nitroganatad Organic*
F: Oxyganatad Organics
6: Pasticidas/Harbicidas
H: Inorganics
I: Phthalatas
J: Sutfatas
12
-------
of the HAPs, but for many of these compounds, the list of products is probably
incomplete.
Reaction Products
The transformation products reported in Appendix A cover a wide range
of chemical compositions. Many of the HAP compounds react with OH radical and are
degraded to low molecular weight aldehydes, alcohols, organic acids, ketones, nitrates,
carbon monoxide, carbon dioxide, and water. Some HAPs are transformed to other
HAP species, so the degree of health risk depends on the relative toxicity of the
original HAP and its transformation products. A further breakdown of the data
obtained during this survey is given in Table 2. This table shows that there were 95
compounds for which no transformation product data were found (84 no product data +
11 nodata at all). Many of the chemicals for which no reaction products are reported
are oxygenated and nitrogenated organic compounds. Even for those chemicals with
reported reaction products, the list of products may well be incomplete, depending on
the rigor of the experimental study. Few studies reported mass balances to document
the completeness of the list of products. This lack of product data represents a serious
gap in our knowledge about hazardous air pollutants and the health risks posed by their
atmospheric transformations. Additional research is needed to elucidate the products
and lifetimes of HAPs representing various classes on the HAPs list.
Removal Processes and Lifetimes
The process that drives the transformation of many of the HAP
compounds in the atmosphere is reaction with hydroxyl radicals, OH. Of the 178
HAPs for which a removal process is reported in Appendix A and Table 1, 145 (82
percent) show reaction with hydroxyl as the most important removal mechanism.
%
Thompson (2) has recently provided an excellent review of the hydroxyl radical and
other species that control the atmosphere's oxidizing capacity.
13
-------
TABLE 2. DATA COMPLETENESS BY COMPOUND CLASS
Data Reported for
Removal Process,
Lifetime and No Product No Transformation No
Compound Class Transformation Products Data Anticipated Data
Hydrocarbons
3
0
0
0
Halogenated Hydrocarbons
18
8
1
1
Aromatic Compounds
15
2
0
1
Halogenated Compounds
4
4
0
0
Nitrogenated Organics
10
33
0
6
Oxygenated Organics
18
21
0
1
Pesticides/Herbicides
4
10
0
1
Inorganics
20
2
12
1
Phthalates
0
4
0
0
Sulfates
2
0
0
0
TOTAL
94*
84
13
11
(*) Includes the 13 compounds that are not anticipated to undergo any atmospheric transformations.
-------
Reactions with ozone and nitrogen trioxide contribute to the removal of a
number of the HAPs, as noted in Appendix A, but these reactions appear to control the
lifetimes of only a few of the species. Photolysis is also an important degradation
mechanism for a number of the HAPs, and it is reported to be the main removal
mechanism for seven chemicals (one of these, CC14, is removed by photolysis in the
stratosphere). Deposition was identified as the primary^emovai process for 15 HAPs.
All but one of these (toxaphene) are inorganic chemicals that are not expected to
undergo significant chemical transformation in the atmosphere. Consequently, their
removal is expected to be controlled by physical removal processes (wet and dry
deposition). Five of the species react with liquid water. The lifetimes of these species
are expected to be controlled by this reaction when liquid water is present (in the form
of clouds, precipitation, over bodies of surface water) but to be dominated by other
removal mechanisms in the absence of liquid water. One of the HAPs (radionuclides
including radon) is removed by radioactive decay and/or deposition, and the other 11
have no reported information on removal processes.
The atmospheric lifetimes of the HAP compound classes are categorized
within broad ranges in Table 3. A total of 178 of the chemicals have lifetimes
reported. Sixty-one of these are based on estimated rate constants derived from
chemical structure. The table indicates that 83 (46 percent) of the 178 chemicals have
lifetimes of less than one day. Most of these species are removed by rapid reaction
with OH. Twenty-five of the species are reported to have lifetimes of one to five days,
and 57 have lifetimes greater than five days. There are conflicting data on 13 of the
HAPs, with eight of these reported to persist from less than one day to five days, and
five reported with residence times from one to greater than five days.
The lifetime data in Table 3 show that hydrocarbons, nitrogenated
organics, aromatic compounds, phthalates, sulfates, and pesticides/herbicides are
generally expected to degrade rapidly in the atmosphere. The oxygenated organics
range evenly across the lifetime ranges. The inorganics, halogenated hydrocarbons,
and halogenated aromatics are reported to be relatively persistent in the atmosphere.
As a cautionary note, we find that comparisons of lifetimes reported in Appendix A
15
-------
TABLE 3. ATMOSPHERIC LIFETIMES OF HAP COMPOUNDS
(in days)
Compound Class
<1
<1 to 1-5
1-5
1-5 to >5
>5
No Estimate
Totals
Hydrocaitoons
2
0
1
0
0
0
3
Halogenatcd Hydrocarbons
5
2
1
0
18
1
27
Aromatic Compounds
12
2
2
0
1
1
18
Halogenatcd Compounds
0
0
1
1
6
0
8
Nitrogenated Compounds
32
1
2
3
5
6
49
Oxygenated Compounds
11
3
14
0
II
1
40
Pesticides/Herbicides
13
0
0
0
1
1
15
Inorganics
4
0
3
1
14
1
23
Phthalates
2
0
1
0
1
0
4
Sulfates
2
0
0
0
0
0
2
TOTAL 83 8 25 5 57 11 189
-------
across HAPs with structural similarities sometimes show inconsistencies. The lifetimes
reported in this document have been measured or estimated by a variety of methods,
and these methods have not been reviewed for consistency. Consequently, the lifetime
estimates provided in this report should be used with caution.
Other Atmospheric Transformations
In addition to transformations of the 189 HAPs, there are other
atmospheric transformations that can elevate the risk to public health. Many chemicals
that are emitted to the atmosphere, whether from anthropogenic or natural sources, are
not on the Title III list of 189 chemicals, and may not be toxic themselves, but may
undergo atmospheric transformations that generate toxic products. Although
examination of non-HAP transformations was outside of the scope of this study, such
transformations should be considered in assessing human exposure to toxic air
pollutants. In the paragraph below, we briefly review one type of study that is
addressing this issue. That research is investigating mutagenic activity from the
atmospheric transformations of non-HAP compounds. The significance of the findings
with respect to public health risk merits our attention.
As noted above, there are non-HAP and even non-toxic compounds that
undergo atmospheric transformations to generate chemicals that may represent human
health hazards. An example of such a compound is the simple hydrocarbon, propylene.
It is reported that this ubiquitous ambient air constituent, when irradiated in the
presence of NO,, yields transformation products that are mutagens. The products that
have been identified from the atmospheric transformation of propylene include
formaldehyde, acetaldehyde, peroxyacety] nitrate, nitric acid, propylene glycol
dinitrate, 2-hydroxy propyl nitrate, 2-nitropropyl alcohol, a-nitroacetone, and carbon
monoxide (3). These products do not account for all of the mutagenic activity; other
unidentified mutagens likely include organic peroxides and nitrates. Further
investigations of the transformation of propylene by reaction with 03 (4) and with
hydroxyl and nitrate radicals (5) also identify organic oxygenates as products, although
they do not account for the mutagenic activity associated with propylene/NO,
17
-------
transformations. This work demonstrates that compounds considered to be non-toxic
can undergo atmospheric transformations to produce chemicals on the Title III list, as
well as other toxic pollutants. These studies were able to demonstrate mutagenic
activity, even though the specific mutagens could not always be identified. This
approach warrants careful consideration as a means of investigating the risks associated
with atmospheric transformations.
CONCLUSIONS AND RECOMMENDATIONS
We have surveyed the available literature to uncover information on the
transformation products and atmospheric persistence of the 189 hazardous air pollutants
listed in the Clean Air Act Amendments. We have been able to estimate the
atmospheric lifetimes for all but 11 of the chemicals. However, the transformation
product information is much less complete. We have been able to identify
transformation products for only about half of the 189 chemicals. Specific conclusions
from this survey are:
(1) Many of the 189 HAPs can be expected to undergo
atmospheric transformations due to reactions with hydroxy!
radical, ozone, nitrate radical, water, or by photolysis.
(2) Reaction product information is absent for 95 of the 189 HAP
compounds, and product data are incomplete for many of the other 94
chemicals.
(3) The transformation products identified from the
atmospheric reactions of HAPs include aldehydes,
alcohols, peroxides, nitrosamines, nitramines, amides,
organic acids, ketones, nitrates, carbon monoxide, carbon
dioxide, and a wide variety of other oxygenated,
nitrogenated, haJogenated, and/or sulfur-containing species.
Many of the products are multifunctional chemicals. Some
of the products are known to be toxic, while many others
have never been tested for toxicity.
(4) Reaction products have not been identified for 43 of the chemicals that
are expected to react rapidly in the atmosphere (lifetime < 1 day).
18
-------
, (5) Many of the 189 hazardous air pollutants undergo transformations to
produce other hazardous chemicals on the HAPs list. For example,
formaldehyde is a product of many HAP transformations.
(6) Transformation products can be either more or less toxic than the original
HAP. For example, one product of chloroform oxidation (phosgene) is
reported to be significantly more toxic than the chloroform itself (6).
(7) Chemicals not currently identified as hazardous air pollutants can undergo
atmospheric transformations to generate toxic products that pose a
potential health risk to humans.
The results from this survey suggest that considerably more information
must be gathered on HAP transformation products before transformations can be
incorporated in health risk assessments for many of the HAPs. We recommend that
research efforts be focused initially on the 11 HAPs for which neither lifetime nor
product data are available, and on those 43 HAPs expected to undergo rapid
atmospheric transformations, but for which no transformation product data are
available. The transformation products of this latter group of chemicals may build up
relatively rapidly, and therefore could represent a health risk if they are toxic. If the
products are found to be nontoxic, then the rapid removal of these HAPs from the
atmosphere should also be taken into account in the risk assessment process. The
specific chemicals in these two groups are listed below:
19
-------
RECOMMENDED PRIORITY CHEMICALS FOR
TRANSFORMATION PRODUCT STUDIES
Rapid Transformation/No Reaction Product Data
Acetamide
2-Acetylaminofluorene
Acrylic acid
4-Aminobiphenyl
o-Anisidine
Benzidine
Bis(2-ethylhexyl) phthalate (DEHP)
Calcium cyanamide
Captan
Carbaryl
Catechol
Chlordane
Chlorobenzilate
Cumene
DDE
Diazomethane
Dibenzofuran
Dibutyl phthalate
3,3'-Dichlorobenzidine
Dichlorvos
Diethanolamine
S^'-Dimethoxybenzidine
Dimethylaminoazobenzene
3,3'-Dimethylbenzidine
Dimethylcarbamoyl chloride
1,2-Diphenylhydrazine
Ethyl carbamate
Heptachlor
Hydrazine
Isophorone
Methoxychlor
Methylhydrazine
Methyl isocyanate
4,4'-Methylenebis (2-chloroaniline)
Methylenediphenyl diisocyanate
4,4'-Methylenedianiline
p-Phenylenediamine
Propoxur
1,2-Propyleneimine
2,4-Toluenediamine
o-Toluidine
Vinyl acetate
Glycol ethers
No Lifetime or Reaction Product Data
Acrylamide
Bromoform
Caprolactam
Chioramben
N.N-Dimethylformamide
Ethylene thiourea
Hexamethylene-1,6-diisocyanate
Hexamethylphosphoramide
Titanium tetrachloride
Triethylamine
Coke oven emissions
20
-------
We recommend that the elucidation of the transformation products of
these HAPs be given a high priority. However, we believe that further prioritization is
possible within this subset of 54 chemicals. Through a review of the toxicity and
emissions of these chemicals, we recommend that 9 of these chemicals be given the
highest priority for transformation product definition. The list of 9 chemicals is shown
in Table 4. Eight of these chemicals are expected to be transformed rapidly in the
atmosphere, but we have little or no information about their transformation products.
We know nothing about the products or lifetime of the ninth chemical. Six of the
chemicals are carcinogenic, and all but one are reported (7) to have total environmental
releases of 100,000 pounds per year or greater. The exception is 3,3'-dichloro-
benzidine, with an estimated release of 23,000 pounds/year. We have included this
chemical on our high priority list as a surrogate for the four carcinogenic benzidine
derivatives on the Title III list of HAPs. Information about the transformation products
of this compound should also be illuminating in terms of the other three species.
21
-------
TABLE 4. RECOMMENDED HIGHEST PRIORITY CHEMICALS FOR
TRANSFORMATION PRODUCT STUDIES
Chemical
Lifetime
(days)
Reaction
Products
Carcinogenic
Environmental Release0
(pounds/year nationwide)
acrylamide
unknown
unknown
yes
4,625,675
acrylic acid
<1
unknown
no
19,337,422
bis(2-ethylhexyl)phthalate
<1
unknown
yes
3,708,811
hydrazine
<1
unknown
yes
454,324
4,4'-methylenedianiline
<1
unknown
yes
454,324
styrene
< 1
incomplete data
yes
41,169,973
glycol ethers
<1
unknown
no
65,736,857
vinyl acetate
<1
unknown
no
7,138,898
3,3*-dichlorobenzkHne
<1
unknown
yes
23,000
(*) Estimated total release and transfers (see reference 7).
-------
REFERENCES
1. B. Daniel, G. Merz, and W. Klopffer, ABIOTIK^ Data-Base, Daniel Electronic,
In behalf of Battelle Institut e.V., Frankfurt, Germany, November 1990.
2. A.M. Thompson, The oxidizing capacity of the earth's atmosphere: probable
past and future changes, Science, 256, 1157, 1992.
3. T.E. Kleindienst, P.B. Shepson, E.O. Edney, L.T. Cupitt, and L.D. Claxton,
The mutagenic activity of the products of propylene photooxidation, Environ.
Sri. Techno!.. 19, 620, 1985.
4. P.B. Shepson, E.O. Edney, T.E. Kleindienst, J.H. Pittman, G.R. Namie, and
L.T. Cupitt, The production of organic nitrates from hydroxyl and nitrate radical
reaction with propylene, Environ. Sci. Technol.. 19, 849, 1985.
5. P.B. Shepson, T.E. Kleindienst, E.O. Edney, L.T. Cupitt, and L.D. Clayton.
The mutagenic activity of the products of ozone reaction with propylene in the
present and absence of nitrogen dioxide, Environ. Sci. Technol.. 19, 1094,
1985.
6. M. Sittig, Handbook of Toxic and Hazardous Chemicals and Carcinogens,
2nd Ed., Noyes Publications, Park Ridge, NJ, 1985.
7. U.S. EPA, Toxics in the community-national and local perspectives, EPA
560/4-91-014, September, 1991.
23
-------
APPENDIX A
SUMMARY OF HAZARDOUS AIR POLLUTANT TRANSFORMATIONS
24
-------
H Compound and
H CAS Number
Chemical
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation ftpoducto
RcfflTBINS
Comments/Notes
B AcetaMehyde
175-07-0
CH,CHO
OH, photolysis
<1
Formaldehyde, carbon dioxide,
carbon monoxide, PAN,
hydrogen peroxide, methyl
nitrate
1,2,4.5,13,14.16,
17,19,20,29,52,
54,55,69,79
1 Acetamide
[60-35-5
CH,C(0)NH,
OH
<1
No information found
21
*
1 Acetonitrile
J 75-05-8
CH,CN
OH
>5
No information found
19,21,52,54,55,
69,101,102,106
I Acetophenone
198-86-2
0=C—CH-
.6
OH
1 to 5
No information found
55
2-Acetylaminofluorene
53-96-3
OH
<1
No information found
21
~
Acrolein
107-02-8
H,C=CHCHO
OH, photolysis,
Oj
<1
Formaldehyde, carbon dioxide,
formic acid
2,3,5,9,13,21,52,
54,55,79,93
1 Acrylamide
179-06-1
CHjCHC(0)NH2
No information
found
No
information
found
No information found
Reaction with OH
and O, likely
25
-------
n Compound ind
| CAS Number
*<*- - - - • . ¦
tmnmn
Formula/Stnidare
M^jor Removal
Reported
Atmospheric
Lifetimes
(days)
Transformation IVoducfa
References
Comments/Notes
D Acrylic Acid
179-10-7
H,C-CHCO,H
OH, deposition
<1
No information found
17,21
1 Acrykmilrile
1107-13-1
CHjCHCN
OH
1-5 to >5
Formaldehyde, formic acid,
hydrogen cyanide, formyl
cyanide, oxalic acid mononttrile
5.7.11,13,19.21.
52,102.103.108
Altyt chloride (3-chloro-l-
propene)
107-05-1
CH,-CHCH,CI .
OH, O,
<1
Formaldehyde, fomric acid,
chloroacetaldehyde,
acetaldehyde, 1,3-
dichloroacetone, acrolein,
glyoxal, PAN. CI-PAN,
chlorinated hydroxy carbonyls
5.21,13,54,55,
93,137
14-Ammobiphenyl
192-67-1
<0€H
OH
<1
No infonnalion found
21
* H
Aniline
62-53-3
nh2
6
OH
<1
Nitrosamines, nilramines, nitro-
benzene, formic acid, hydrogen
peroxide, nitrophenols, nitro-
sobenzene, benzidine, a mi no-
phenol, nitroaniline, phenol,
hydroxybenznnitrile, N-phenyl-
formamide
7,8,9,55,102
-------
H Compound Mid
CAS Number
Chemical
Formula ^Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes
o-Anisidine
90-04-0
nh2
<§r
OH
<1
No information found
21
*
Asbestos
1 1332-21-4
Silicate minerals of the
serpentine and amphibole
groups
Deposition
>5
No chemical transformation
112
Benzene
71-43-2
0
OH, NO,
>5
Phenol, nitrobenzene, nitro-
phenol, dinitrophenol, glyoial,
2-Butene-l,4-dial
7,8,9.14,17,19,
21,35,41,52,54,
55,65
Benzidine
92-87-5
OH
<1
No information found
21
^ ¦
27
-------
Compound Hid
CAS Number
Chemical
Form (Ha/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes 1
n Benxotrichloride
U 98-07-7
CI
ci—A-a
6
OH
>5
No information found
21
* 1
Benzyl chloride
100-44-7
CI—CH,
6
OH
1 to >5
Phenol, chloromethyl phenols,
ring cleavage products
5,21,31,52.54,
55,103
Biphenyl
92-52-4
OH
1 to 5
3-Nilrobiphenyl
19,21,23,45,46,
47,48,49,52,55,
78
Bis (2-ethylhexyl)
phthalate (DEHP)
117-81-7
o
^^C-OCH-C^
o
OH, deposition
<1
No information found
21
* |
I Bis (chloromethyl) ether
1542-88-1
cich,och,ci
Liquid H20,
OH
< 1 to 1-5
Hydrochloric acid, formalde-
hyde, chloromethyl formate
5,21,130,131 I Rapid reaction with
1 liquid H,0
-------
n Compound md
1 CAS Number
Chemkal
Formula/Structure •
M^for Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation ftoducts
References
Comments/Notes Q
I Bromoform
H 75-25-2
CHBr,
No information
found
No
information
found
No information found
No literature; see H
chloroform for g
analogous pathways |
1,3-Butadtene
106-99-0
HjC-CHCH-CH,
OH, O,
<1
Acrolein, formaldehyde
15,17,21,52,54.
55,108,138
Caktum cyanamide
156-62-7
CaNCN
OH
<1
No information found
21
* N
Caprolactam
105-60-2
- oil) -
a W* -Z-w-t,
&
No information
found
«
No
information
found
No information found
Captan
133-06-2
0
_ 4 sea,
av
OH
<1
No information found
21
* D
Cvtiryl (Styin)
63-25-2
CH.-MH
cX
@6
OH
<1
No information found
21
* B
29
-------
H Compound and
| CAS Number
Chemical
Formula/Structure
M^for Removal
IVoeesses
Reported
Atmospheric
Lifetimes
(days)
Transformation hotels
References
Comments/Notes
U Carbon disulfide
J 75-15-0
CS,
OH
1-5 to >5
Carbonyl sulfide, sulfur
dioxide
17,19,26,119
Considerable dis-
agreement in
reported OH rate
constants
| Carbon tetrachloride
[56-23-5
cci.
Photolysis in
stratosphere
>5
No tropospheric reactions
anticipated
5,7,15,21,55,69
Carbonyl sulfide
463-58-1
COS
OH
>5
Carbon dioxide, hydrogen
sulfide, sulfur dioxide
19,26,27,69
Catechol
120-80-9
OH
JL OH
OH
<1
No information found
21
•
Chloramben
133-90-4
COOH
JL
jOc
No information
found
No
information
found
No information found
Chlordane
57-74-9
a a
**
OH
<1
No information found
21,136
~
-------
Compound snd
U CAS Number
Chemical
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes
1 Chlorine
17782-50-5
CI,
Photolysis
<1
Hydrogen chloride
III
HOiforncetic acid
J 79-11-8
CICH,CO,H
OH, deposition
>5
No information found
21
•
12-Chloroacetophcnone
1532-27-4
OH
>5
No information found
21
* I
1 Ctitorobenxene
| 108-90-7
CI
^6
OH
>5
Chlorophenols, 1 -chloro-3-
nitrobenzene, ring cleavage
products
5,7,8,9,17,19,21.
23,42,55
_
1 Chforofcenzilate
9 510-15-6
jCr®i
ct a
OH
<1
No information found
21
• I
9
Chloroform
67-66-3
ch ci,
OH
>5
Phosgene, hydrogen chloride
5,7,14,15,17,21,
22,54,55,69,129
Chloromethylmethyl ether
107-30-2
aCH,OCH,
Liquid H,0,
OH
< 1 to 1-5
Chloromethyl formate, methyl
formate, methanol,
chloro methanol
5,21,130
Rapid reaction with I
liquid H,0 1
31
-------
H Compound md
U CAS Number
¦ ,,, f ,|
likrhch
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation lYoducts
References
Comments/Notes
CMoroprane (2-chloro
1,3-butadiene)
126-99-8
CH,«CHCC1=CH,
OH, O,
<1
Formaldehyde, ethanediol,
chlorohydroxy acids, aldehydes
5.21
Creaols/Cresylltc Acid
1319-77-3
0
~CHg,+OH
OH. NO,
<1
Hydroxynitrotoluenes, ring
cleavage products
5.21
o-Cresol
95-48-7
OH
&-
OH, NO,
<1
Methyl nitrophenols, 2-hydroxy-
benzaldehyde, dihydroxy-
toluenes, hydroxynitrotoluenes
4.7.17,21,43.52,
54.55,60,102,
103,117
m-Cieaol
108-39-4
OH
OH, NO,
<1
3-Methyl-2-nitrophenol,
S-methyl-2-nitrophenol,
hydroxynitrotoluene,
dihydroxytoluene
17,21,52,54,103,
117
p-C(C90l
106-44-5
OH
(6
CH,
OH, NO,
< 1
4-Methyl-2-nitrophenol,
hydroxynitrotoltienes,
dihydroxytoluenes
8,17,21,52,54,
55,60,103,117
-------
Compound Mid
CAS Number
Chemical
Formula/Structure
M^for R (moral
IVocbs«s
Reported
Atmospheric
Lifetimes
(days)
l
Transformation Products
References
Comments/Notes 1
Cumene (isopropyl
beiume)
98-82-8
•
OH
<1
No information found
21,55
See toluene for |
analogous products H
2,4-D, salts and esters
(2,4-dichlorophenoiy-
acetic acid)
94-75-7
a
OH
<1
2,4-dichloroanisole
21,33
~
DDE
(1,1 -Dkhkm>-2,2-bis-
(p-chlorophenyl)ethylene)
72-55-9
-CK <•.
Photolysis, OH
<1
No information found
21
~
Diaaomethane
334-88-3
CH,N,
o,
<1
No information found
52
Dibenrofuran
132-64-9
OH
<1
No information found
21,30,31
*
33
-------
Compound mmI
CAS Number
Chemical
Fonnul*/Structure
M^Jor Removal
IVwcesses
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Cm mieiits/No*«
1,2-dibromo-
3-chloropropsne
96-12-8
BrCHjBfCHCHjCl
OH
>5
1,2-Dibromopropwtol,
chlorobromoprofimol
21,32,50
Dibutyfphthalate
84-74-2
0
OH, deposition
<1
No information found
21
~
1,4-Pichlorobenacnc
(p-dichlorobenzene)
106-46-7
a
T
OH
>5
2.5-Pk:hloro-6-nitrophenol. ¦'
2,5-dtcMnronitrohenisne,
2,5-dichloraphenol. chlorinated
phenols, nitro compounds, ring
cleavage products
5,7,17,19,21.5!,
54,55,56,70,72
3,3'-Dich1oTobenzidine
9!-94-1
Photolysis, OH
<1
No information found
21
* 1
1 Dichloroefhyl Elher (bis(2-
1 chloroelhyl) ether)
1111-44-4
(CICHjCH^O
OH
1 to 5
No information found
21
• |
-------
Compound and
CAS Number
Chemical
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
References
—]
1,3-diehk>ropropenc
542-75-6
CH,CICH-CHCI
OH. O,
<1
Formylchloride, chloroacetalde-
hyde, chloroacetic acid, carboo
dioxide, carbon monoxide,
hydrogen chloride
17,21,34,55,74,
75
Dichlorvos
62-73-7
°V\?
M-ch=ccl
CH fi
OH
<1
No information found
95
*
Diethanotanine
II1-42-2
(HOC,H4),NH
OH
<1
No information found
17,21
N.N-Diethylaniline
121-69-7
CH,
1 3
N-CH,
6
OH
<1
Nitrosamines, nitramines, N-
methyl formanilide, formic
acid, formaldehyde, hydrogen
peroxide
9,55,102,128
Diethyl sulfate
64-67-5
(c,h,)jso4
Liquid H20,
OH
<1
Monoethyl sulfate, sulfuric
acid, ethanol
100
Products based on
hydrolysis
3,3' Dimethoxybenzidine
119-90-4
CHjQ OCH,
OH
<1
No information found
21
* 1
35
-------
| Compound and
|| CAS Number
Chemical
Formula/Sir ttui e
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes
|| DinwthylaminoMobenttne
U 60-11-7
OH
<1
No information found
21
~
I 3,3' Dimethylbenridine
[ 119-93-7
OH
<1
No information found
21
*
Dimethy (carbamoyl
chloride
79-44-7
-------
Compound and
CAS Number
Chemical
Formula/Struct tire '
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transfnrmatiofi Products
References
Comments/Notes
Dimethyl sulfate
H 77-78-1
(CH,)jS04
#•
Liquid H20;
OH
<1
Mono methyl hydrogen sulfate,
sulfuric acid, methanol
99
Products based on
hydrolysis
4,6-dmilro-o-cresol, and
salts
534-52-1
OH
OjH JL
ior
NO,
OH
>5
No information found
21
*
2,4-dmitrophenol
51-28-5
OH
NO,
OH
>5
No information found
21
*
2,4-dinitrotoliiene
121-14 2
CH3
NO,
Photolysis
1 to 5
No information found
21
~
37
-------
1 Compound and
[ CAS Number
Chemical
Formula ^Structure
M^jor Removal
Processes
Reported
Atmospheric
Liretimes
(days)
Transformation Pnwtucts
References
Comments/Notes 1
H 1,4-Dioxane
R 123-91-1
0
OH
1 to 5
No information found
21,28,55
n
1,2-diphenylhydrazine
1122-66-7
OH
<1
No information found
21
* H
EpkMorohydrin
106-89-8
0
OH
>5
Formaldehyde, glyoxylic acid,
PAN (possibly), chloroacetalde-
hyde, peroxychloroacetyl nitrate
5,7,17,21,40,55
1,2-Epoxybutane
106-88-7
0
/\
HgC-CHCHgCHj
OH
1 to S
No information found
8,55,73,86
-------
| Compound and
CAS Number
Chemical
Formula/Structure
M^for Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transfnrmation Products
References
Comments/Notes i
Ethyl Acrylate
140-88-5
HjC-CHCOjC,Hj
o,
1 to 5
Glyoxylic acid, ethyl glyoxy-
late, ethyl formate, epoxides
11,21
1 Ethyl benzene
1100-41-4
6
OH
<1
Glyoxal, ethylglyoxal,
acetophenone, formaldehyde,
acetaldehyde, peroxyacetyl
nitrate, peroxypropionyl nitrate,
butenedial, 4-oxo-2-hexenal,
2-ethyl-butenedial,
4-oxo-2-butenoic acid,
4-oxo-2-hexenoic acid
17,21,31,54,55,
110
Ethyl carbamate
51-79-*
NH,C(0)0CjHj
OH
<1
No information found
21
~
Ethyl chloride
(Chloroethne)
75-00-3
CH,CH,CI
OH
>5
No information found
14,17,21,55
Ethylene dibrotnide
(1,2-Dibromoethane)
106-93-4
CH,BrCH,Br
OH
>5
Formaldehyde, bromoethanol,
hydrogen bromide, formyl
bromide
5,14,17,21,55,76
Ethylene dichloride
(1,2-dichloroethane)
107-06-2
CHjCICHjCl
OH
>5
Formyl chloride, chloroacetyl
chloride, hydrogen chloride,
chloroethanol
7,14,15,17,21,
55,76
Ethylene Glycol
1107-21-1
HOCH2CHjOH
OH, deposition
1 to 5
No information found
17,21,55
1
39
-------
Compound and
CAS Number
Chemical
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes
Ethylene* mine
151-56-4
ch2
Hh(—CH2
OH
<1 to 1-5
No information found
21,55
Ethylene oxide
75-21-8
OH
>5
Methanol, nitromethane, methyl
nitrate, ethyl nitrate
4,5,7.9,15.17,
19,21,55
Ethylene thiourea
96-45-7
| NH
NH^s
No information
found
No
information
found
No information found
Ethylidene dichloride
(1,1 -dichloroethane)
75-34-3
CHjCHO,
OH
1 to 5
No information found
14,21,39,55,76
Formaldehyde
50-00-0
HCHO
Photolysis, OH
<1
Carbon monoxide, carbon
dioxide, hydrogen peroxide,
hydrogen
4,5,9,13,16,17,
20,21,52,53,54,
55,69,79,91
Heptachlor
76-44-8
'
OH, photolysis
<1
No information found
21
*
-------
Reported
Atmospheric
Lifetimes
(days)
Chonicml
Fonnula/Stiutture
Transformation Products
Comments/Nates
HexMchkwobetiune
118-74-1
OH
No information found
>5
Hexachtorobuiadiene
87-68-3
af_fYijYi«rn
2*->111 *¦ V»V#I;
OH
No information found
>5
Hexachloro-
cyclopentadiene
77-47-4
OH, O,
Phosgene, diacytcfctorides,
ketones, hydrogen chloride
5,21
HexacMoroethane
67-72-1
OH
>5
No information found
No information found
No information
found
No
information
found
No information found
No information
found
No
information
found
2-HexyInitrate, 3-he*ylniti*te.
aldehydes, ketones
tfexam
110-54-3
OH, NO,
<1
41
-------
Compound and
CAS Nam her
Chemical
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes |
Hydrochloric acid
(HCl)7647-0l-0
HO
Deposition
1 to 5
Chloride salts (e.g., ammonium
chloride)
133,134
Hydrogen fluoride (HF)
7664-39-3
HF
Deposition
1 to 5
Fluoride salts
133,134
By analogy to HCI [
Hydroquinone
123-31-9
o
OH
1 to 5
No information found
21
* 1
laophocone
78-59-1
ch,
CH,
OH
<1
No information found
21
* 1
Lindane (ar-Hexachloro-
cyclohexane)
58-89-9
OH, photolysis
<1
a-Hexachlorocyclohexane
(photoisomerization)
21,33
* 1
-------
Compound and
CAS Number
Chemical
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation IVoducts
*
References
Comments/Notes
Maletc anhydride
108-31-6
0
0=0^CH"CH^C=0
OH
<1
Carbon dioxide, carbon
monoxide, aldehydes and esters
which should photolyze
5,17
Methanol
67-56-1
CHjOH
OH, deposition
1 lo 5
Water, formaldehyde
4,16,17,19,21,
55,69
—
Methoxychlor
72-43-5
OH
<1
No information found
21
*
Methyl bromide
(Bromo methane)
74-83-9
CHjBr
OH
>5
Formaldehyde, carbon
monoxide, hydrogen bromide
14,21,37,40,55
Methyl chloride
(Chkmnnethane)
74-87-3
CH,CI
OH
>5
Formaldehyde, carbon
monoxide, hydrogen chloride
14,21,17,37,55,
102
Methyl chloroform
(1,1,1 -Trichloroethane)
ca,cH,
OH
>5
Phosgene, formaldehyde,
hydrogen chloride, carbon
monoxide, acetyl chloride,
chloroacetyl chloride, formyl
chloride |
5,6,21,55,129
43
-------
II CoiHpowd and
1 CAS Number
Chemical
Fonmita/Struclure
Msyor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation lYwtuels
References
Comments/Notes |
B Methyl ethyl ketone
I (2-butanone)
J 78-93-3
C,HjCOCH,
Photolysis, OH
<1
Carbon dioiide, carbon
monoiide, water, formal-
dehyde, methanol, formic acid,
acetic acid, acetaldehyde, PAN
8,17.18,21.22,
29,55,87,88
U Methyfhydrazme
J 60-34-4
CHjNHNH,
OH. O,
<1
No information found
21,52,55,102,122
I Methyl iodide
1 (lodomethane)
II74-88-4
CH,I
OH
>5
Formaldehyde, carbon
monoxide, hydrogen iodide,
formyl iodide
5.21
U Methyl i-butyl ketone
108-10-1
(CHj)jCHCHjCOCH,
OH
1 loS
Acetone, PAN, formaldehyde
17,21,29,55
Methyl iaocyanate
624-83-9
CHjNCO
OH
<1
No information found
21
Methyl methacrylate
80-62-6
HjC «» C(CH^COjCH,
OH, O,
<1 to 1-5
Pyruvic acid, methyl pyruvate,
epoxides
16,17,21
Methyl t-butyl
ether
1634-04-4
(CHjJjCOCH,
OH
1 to 5
Formaldehyde
4,11,24,25,55
4,4'-Methylene bis
(2-chloro aniline)
101-14-4
ct a
OH
<1
No information found
21
~
Methylene chloride
75-09-2
ci-ch2-ci
OH
>5
Phosgene, carbon monoxide,
carbon dioxide, hydrogen
chloride, formyl chloride
6,7,14,15,17,21,
69,102,129
1
AA
-------
I Cmpnwd Mid
| CAS Number
Chemical
Formula/Structure
M%jor Removal
Procevses
Reported
Atmospheric
Lifetimes
(days)
i
Transformation Products
t
References
Comments/Notes
H Methylenediphenyl
B diraocjranate
1101-68-8
OH
<1
No information found
21
*
4,4'-Methylenediani1iiie
101-77-9
OH
<1
No information found
21,55.120
| Naphthalene
91-20-3
00
OH, NO,
<1
Methylnitronaphthalene.
3-nitrohiphenyl,
2-nitronaphthalene,
1 -nitronaphthalene
8.9,17,19,21,52,
55,56,61.68,78,
90,105
Nitrobenzene
98-95-3
NO.
6
OH
>5
Nitrophenols, ring cleavage
products
4,5.7.9,17,55,
102,126
45
-------
R Compound and
| CAS Number
Chemical
Pomrala/Stnicture
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(d»ys)
Transformation Products
References
Comments/Notes
14-Nitrobi phenyl
192-93-3
©CH
OH
1-5 to >5
No information found
21
*
14-Nitrophenol
B 1004)2-7
no2qh/>h
OH
1-5 to >5
No information found
19,21,117
Reaction of nitro- I
phenols generally 1
much slower than
those of phenols
(117)
2-Nitropropane
.79-46-9
CH,CH(NOJCH,
OH
<1
Formaldehyde, acetaldehyde
5,21
N-nitroso-N-methylurea
1684-93-5
CH|N(N0)C(0)NHj
OH, photolysis
<1
Aldehydes, nitramines
5,21
| N-nitrosodimethylamine
62-75-9
(CH^NNO
Photolysis, OH
<1
Nitric oxide, nitramines,
aldehydes
5,21,52,55,107,
121
Products based on
analogy with N-
nitrosodiethylamine |
N-Nitrosomorpholine
59-89-2
N=0
6
OH, photolysis
<1
Aldehydic ethers, nitric oxide
5,21
46
-------
8 Compound Mid
Q CAS Number
. « «
vMhIVOD
Formula/Structure
M^for Removal
IVoctsses
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes
H » ¦»'
u raiauiiun
156-38-2
O
z
o
>0
<1
Paraoxon, 4-nitrophenol,
diethylphosphoric acid, diethyl-
thiophosphoric acid
21,33,95,97,135
Peirtachloronitrobenzene
82-68-8
NOf
OH
>5
No information found
21
* 1
| Pentachtorophenol
| 87-86-5
OH
OH
>5
No information found
21,23
Phenol
108-95-2
OH
6
OH.NO,
<1
Dihydroiybcnaenes, 2&4-nitro-
phenols, benzenetriols
5,6,7,10,17.19,
21,50,51,54,55,
117
47
-------
Compound and
CAS Number
Chemical
Formula/Struct ore
M^}or Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation IVoducts
References
Comments/Notes 1
p-Phenylenediamine
106-50-3
NH.
$
nh2
OH
<1
No information found
21
* I
Phosgene
75-44-5
coci,
Liquid H,0,
deposition
1 to 5
Carbon dioxide, hydrogen
chloride
5,6,17,21.40,
129.132
Phosphine
7803-51-2
PH,
OH
<1
Phosphate salts
19
Phosphorus (elemental)
7723-14-0
p«
o,
<1
P4P„ P/V mixture of
phosphorus acids (in presence
of liquid water)
94.143
Phthalic anhydride
85-44-9
o
OH, deposition
>5
No information found
21
* 1
Polychlorinated biphenyls
j 1336-36-3
Biphenyl with CI at various
levels of saturation
OH, deposition
>5
Hydroxy PCBs, ring cleavage
products
5,116
I
-------
Compound and
CAS Number
Chemical
Formula/Structure
M^for Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes
1,3-propane sullone
1120-71-4
f r°
OH
1 to 5
No information found
21
*
6-propiolactone
57-57-8
OH
>5
No information found
21
Proptonaldehyde
123-38-6
CjH'jCHO
OH
1 to 5
No information found
4,21,69
See acetaldehyde 1
for analogous B
products 1
Prapoxor (Baygon)
114-26-1
O0^
OH
<1
No information found
21
* 1
Propylene dtchloride (1,2-
dichloropropane)
78-87-5
ch,chcich,ci
OH
>5
No information found
21,55,75
*
49
-------
Compound and
CAS Number
Ctmnkal
Formula/Structure
M^Jor Removal
FVocchb
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes l
Propylene oxide
75-56-9
o
/\
CH3CHCH2
•
OH
>5
Formaldehyde, gtyoxylic acid,
methylglyoxal, acetafdefiyde,
propionaldehyde, possibly
acetone and PAN
5,6,7,17,55
U 1,2-Propyleneimine
| (2-methyl ariridine)
75-55-8
w
/\
CH3CHCH2
OH
<1
No information found
21
• I
Qoinoline
91-22-5
00
OH
1 to 5
No information found
21
*
* 8
Quinone
106-51-4
0
OH
>5
No information found
21
-------
Compound and
CAS Number
Chemical
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes I
1 Styrene
100-42-5
or*
OH, O,, NO,
<1
Peroxybenzoylnitrate,
benzaldehyde, formaldehyde
17,21,52,54,55,
71,81,103.144
Styicne Oxide
96-09-3
_ CH-CH
OH
1 to 5
No information found
21
* 1
2,3,7,8 Tetrachloro-
dibenxo-p-dioxin
1746-01-6
OH, deposition
1 to 5
No information found
5,21
* D
1,1,2,2-Tetrachloroethane
79-34-5
ci,chchci,
OH
>5
No information found
21
* I
Tetrachloroethylene
(Perchloroethylene)
127-18-4
ci2c=cci,
OH
>5
Phosgene, formic acid, tri-
chloroacetylchlnride, carbon
monoxide, hydrogen chloride
7,15,21,34,35,
54,55,69,80,129
Titanium Tetrachloride
7550-45-0
TiCI4
No information
found
No
information
found
H
No information found
51
-------
| Compound and
| CAS Number
CVwkal
Formula/Structure
M^Jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
m
References
Comments/Notes p
| Tohiene
I 108-88-3
CH3
6
OH
1 lo 5
Benzaldehyde, nitrotoluene,
o,m,p-cresols, nitrocresols,
methyl nitrate, methyl glyoxal,
PAN, formaldehyde, benzyl-
nitrate, acetaldehyde, glyoxal,
dicarbonyls, benzoic acid, 2-
hufenoic acid, 2-butenal, acetic
acid, butenedial, 4-oxo-2-
pentenal, 4-oxo-2-butenoic acid,
4-oxo-2-pentenoic acid
4,5,6,7,9,14.17,
19,21,35,52,54,
55.65,102.110,
138,140,141
2,4-Toluenediamine
95-80-7
CH,
NHt
OH
<1
No information found
21,55,102,120
2,4-Tohwne
diisocyanate
584-84-9
CH.
T OCN
o
OCN
OH, photolysis,
liquid wafer
<1
Toluenediamine and diurethanes
21,55,120,132,
142
I
-------
Compound and
CAS Number
Chemical
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation IVoduds
References
Comments/Notes
o-Tohiidine
95-53-4
CHa
JC.nh2
OH
<1
No information found
21
~
Toxaphene
8001-35-2
R, R,
CHjCI CHCIj
chq, cH,a
CHjC! CH,CI
Deposition
>5
No information found
96
1,2,4-Trichlorobcnrene
120-82-1
a
?
OH
>5
No information found
19,21,23,51,55,
56,72,82,89,102
11,1,2-Trichloroethane
179-00-5
CHjCICHCI,
OH
>5
No information found
21,55,84,85,102
1
53
-------
Compoand and
CAS Number
ChanhJ
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes
Trichtoroethylene
79-01-6
ci2c-chci
OH
>5
Phosgene, dichloroacetyl-
chloride, fortnyl chloride, tri-
chloroethylene oxide, chloro-
form, formic acid, carbon
monoxide, hydrogen chloride
4,5,6,7,13,15,17,
21,22,34,35,69,
129
B 2,4,5-Trichlorophenol
195-95-4
OH
*
OH
>5
No information found
10,12,21,23
12,4,6-Trichlorophenol
188-06-2
OH
OH
>5
No information found
10,21,23
Triethy famine
1 121-44-8
(CjH,),N
No information
found
No
information
found
No information found
I
-------
Compound and
CAS Number
Chmiad
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(d-ys)
Transformation Pindutta
t
References
Comments/Notes
Trifluralin
1582-09-8
CH.-CH.-CH.
^.CHj-CHj-CH,
°«H. I .no,
nor
OH, O, O,
<1
Dealkylated trifluralin
97,98
~
2,2,4-Trimethylpentane
540-84-1
CH,C(CH^CHjCH-
(CH,)CH,
OH
1 to 5
Aldehydes, ketones
55,102,115
Vinyl acetate
108-05-4
CHjCOjCH—CHj
OH
<1
No information found
17
_
Vinyl Bromide
593-60-2
HjC-CHBf
OH, O,
< 1 to 1-5
No information found
4,21,55,57,102
See vinyl chloride
for analogous
products
Vinyl chloride
75-01-4
H,C-CHC1
OH, O,
< 1 to 1-5
Formic acid, formyl chloride,
hydrogen chloride, carbon
monoxide, formaldehyde,
carbon dioxide, monochloio-
acetaldehyde, monochloro-
peroxyacetyl nitrate
4,21,34.38.50.
52,54,55,57,58,
59
—
Vinylidene chloride
(1,1 -dichloroethylene)
75-35-4
HjC-CQj
OH, O,
<1
Phosgene, formaldehyde, formic
acid, chloroacetyl chloride,
carbon monoxide
7,13,21,52,54,
55,74,77,83,93
Xylenes (mixed)
133-02-07
(0 + (CH3)2
OH
<1
Substituted benialdehydes,
hydroxy xylenes, nitro
compounds, methyl glyoial,
biacetyl, ring cleavage products
5,21,35
55
-------
Q Compound and
| CAS Number
tamnan
Formula/Structure
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes
¦ o-xytene
H 95-47-6
CHS
6"
OH
<1
Tolualdehyde, dimethyl
phenols, dimethyl nitrobenzene,
maleic anhydride, biacetyl,
glyoxal. methyl glyoxal,
acetaldehyde, formaldehyde,
CO, PAN, butenedial, 4-oxo-2-
pentenal, 3-methyl-4-oxo-2-
pentenal, carboxylic acids
8,17,19,44,52,
54,55,60,65,103,
110
m-xyfene
108-38-3
CM,
OH
<1
Tolualdehyde, formaldehyde,
methyl glyoxal, acetaldehyde,
aliphatic dicarhonyls, PAN,
CO, glyoxal, 4-oxo-2-pentenal,
2-methyl-2-butenedial, 2-
methyl-4-oxo-2-pentenal,
carboxylic acids
8,9,14,17,21,55,
103,110
p-xylaie
106-42-3
ch3
O
5
No significant chemical trans-
formations
5
9 Arsenic Compounds
Primarily inorganic arsenic
compounds in particle
phase
Deposition
>5
No significant chemical trans-
formations
5
| Beryllium Compounds
Inorganic compounds in
particle phase
Deposition
>5
No significant chemical trans-
formations
5
1
-------
Cwpovnd ud
CAS Nianher
~ « «•
vHBMCH
Focmnta/Strucfare
M^jor Removal
Processes
Reported
Atmospheric
Lifetimes
(days)
Transformation IVoducts
References
Comments/Notes
Cadmium Compounds
Inorganic compounds in
particle phase
Deposition
>5
No significant chemical trans-
formations
5
Chromium Compounds
Inorganic compounds in
particle phase
Deposition
>5
No significant chemical trans-
formations
5
Cobalt Compounds
Inorganic compounds in
particle phase
Deposition
>5
No significant chemical trans-
formations
5
Coke Oven Emissions
Mixture of organic and
inorganic vapors and particles
No information
found
No
information
found
No information found
Species undefined
(see polycyclic
organic matter)
Cyanide Compounds
e.g., HCN (74-90-8), propio-
nitrile, C,H,CN (107-12-0).
cyanogen, C,N, (74-87-5).
(See .also acetonitrile,
•crylonitrile)
OH, O,
>5
No information found
9,21,52,54,55,
69,127
Glycol Ethers
e.g., HOCHjCHjOCH,
OH
<1
No information found
17,55
Lead Compounds
Primarily inorganic
compounds in particle phase.
Deposition
>5
No significant chemical
transformations
5
Trace amounts of organo-lead
compounds, e.g., tetraethyl
lead (CjH,)4Pb (78-00-2).
OH.O,,
photolysis
<1 to 1-5
Inorganic Pb compounds
21,52,55,123,124
I Manganese Compounds
Inorganic compounds in the
particle phase
Deposition
>5
No significant chemical
transformations
5
|
57
-------
C?4MI|KKM£ ssid
CAS Number
Fotmula/Stnadwc
mm—9 ft i. ¦ ,l
HV^|Or VCCTPOtII
IVoctsses
Reported
Atmospheric
Lifetimes
(days)
Transformation Products
References
Comments/Notes
Mercury Compounds
Primarily elemental mercury
vapor, Hg*
Aqueous O,,
deposition
>5
Particulate Hg compounds (see
below)
104
Small amounts of particulate
inorganic Hg compounds
Deposition
>5
No significant chemical
transformations
5
Gaaeoti* organic Hg»
compounds, e.g., (CH,)jHg
(593-74-8)
OH
<1
Particulate Hg compounds (see
above)
55,125
1 Fine Mineral Fibers
Fibrous glass, mmeral wool,
or ceramic fibers, similar in
shape but chemically and
physically distinct from
asbestos fibers
Deposition
>5
No chemical transformations
112
B Nickel tjompcpund^
Inorganic compounds in the
particle phase
Deposition
>5
No significant chemical
transformations
5
I Polycyclic Ofpnic matter
(aee text)
e.g.( Phenanthrene (85-01-8),
¦tlnocM (120-12-7),
(See also naphthalene)
OH, HO,
<1 to 1-5
Nitroarenes, nitronaphthakaies,
nitrofluoranthenes, nitro-
pyrenes, nitroacenaphthalenes
45,46,47,105,
111,139
Radionuclides
(including Radon)
Radon gas
Radioactive
decay
1 to 5
Radioactive daughters in the
particle phase (see below):
("•Po.^Pb, I,4Bi,,wPo)
113,114
Radioactive compounds in the
particle phase
Deposition
>5
No significant chemical
transformations
Selenium Compounds
Inorganic compounds in the
particle phase
Deposition
>5
No significant chemical
transformation
5
|
* Atmospheric lifetime calculated using rate constants estimated from structure-activity relationships.
58
-------
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64
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