United States EpA 600/6-84-011
Environmental Protection
A9ency FEBRUARY 1984
&EPA Research and
Development
DATA ACQUISITION FOR ENVIRONMENTAL
TRANSPORT AND FATE SCREENING FOR
COMPOUNDS OF INTEREST TO THE OFFICE
OF EMERGENCY AND REMEDIAL RESPONSE
Prepared for
OFFICE OF EMERGENCY AND REMEDIAL RESPONSE
Prepared by
Office of Health and
Environmental Assessment
Washington DC 20460
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February 1984
DATA ACQUISITION FOR ENVIRONMENTAL TRANSPORT AND FATE SCREENING
FOR COMPOUNDS OF INTEREST TO THE OFFICE OF EMERGENCY AND REMEDIAL RESPONSE
By
H. M. Jaber, W. R. Mabey, A. T. Liu,
T. W. Chou, H. L. Johnson, T. Mill,
R. T. Podoll, and J. S. Winterle
SRI International
333 Ravenswood Avenue
Menlo Park, CA 94025
EPA Contract No. 68-03-2981
Work Assignment No. 14
Project Officer
Lee A. Mulkey
Environmental Research Laboratory
U.S. Environmental Protection Agency
Athens, GA 30613
Technical Project Monitor
Gregory Kew
Exposure Assessment Group
Office of Health and Environmental Assessment
Office of Research and Development
U.S. Environmental Protection Agency
Washington, DC 20460
OFFICE OF HEALTH AND ENVIRONMENTAL ASSESSMENT
OFFICE OF RESEARCH AND DEVELOPMENT
U.S. ENVIRONMENTAL PROTECTION AGENCY
WASHINGTON, DC 20460
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DISCLAIMER
This report has been reviewed in accordance with U.S.
Environmental Protection Agency policy and approved for
publication. Mention of trade names or commercial products
does not constitute endorsement or recommendation for use.
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FOREWORD
The Exposure Assessment Group of EPA's Office of Research and
Development has three main functions: 1) to conduct exposure
assessments; 2) to review assessments and related documents; and 3) to
develop guidelines for Agency exposure assessments. The activities
under each of these functions are supported by and respond to the needs
of the various EPA program offices. This project was undertaken to
gather data for use in assessing enviornmental transport and fate of
chemicals for the Office of Emergency and Remedial Response (OERR) and
therefore falls under the first function.
The Office of Emergency and Remedial Response is required to
determine "reportable quantities" (RQs) for various chemicals under
Sections 101(14) and 102 of the Comprehensive Environmental Response,
Compensation, and Liability Act of 1980 (CERCLA). After promulgation of
regulations listing RQs, releases to the environment of amounts of these
chemicals in excess of the corresponding RQ must be reported to a
designated Federal organization. The toxicity of each chemical is one
of several factors considered in determining an appropriate RQ. Since
the knowledge of the transport and fate of these chemicals in the
environment is important in determining their potential toxicity it is
imperative to gather basic data to evaluate transport and fate.
James W. Falco, Director
Exposure Assessment Group
ii
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ABSTRACT
Physical properties, equilibrium, and kinetic constants for
evaluating the transformation and transport in aquatic systems for
organic chemicals of interest to the Environmental Protection Agency
have been obtained from the literature and calculated from theoretical
or empirical relations. Values for selected physical properties such as
melting point, boiling point, vapor pressure, water solubility, and
octanol/water partitioning, and for rate constants such as hydrolysis,
microbial degradation, photolysis, and oxidation are listed for each
chemical along with the source of the data. Values are reported in
units suitable for use in a current aquatic fate model. A discussion of
the empirical relationships between water solubility, octanol/water
partition coefficients, and partition coefficients for sediment and
biota is presented.
This report was submitted in partial fulfillment of Contract No.
68-03-2981 by SRI International under the sponsorship of the U.S.
Environmental Protection Agency. This report covers a period from 1 May
1983 to 30 September 1983 and work reported herein was completed as of
30 September 1983.
iii
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CONTENTS
FOREWORD ii
ABSTRACT ill
1. Introduction 1
Purpose 1
Background 2
References 8
2. Definition of Processes and Sources of Data 9
Basis for derivation of data 9
Chemical name, Chemical Abstracts Service registry
number, and molecular weight 10
Water solubility 10
Melting and boiling point 11
Vapor pressure 11
Molecular weight to oxygen ratio 12
Octanol/water partition coefficient • 12
Hydrolysis rate constants 13
Microbial degradation rate constant 14
Photolysis rate constant 16
Oxidation rate constant 16
References 20
3. Data Sheets for Chemicals of Interest 22
List of data sheets 23
List of source codes 26
Data sheets 28
References Ill
4. Calculation of Partition Coefficients of Organic
Chemicals in Aquatic Environments 113
iv
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SECTION 1
INTRODUCTION
PURPOSE
Decisions on possible regulatory action or cost-effectiv.e remedial
measures for toxic chemicals require an understanding of environmental
and human risks associated with the manufacture, use, and disposal of
chemicals. Part of the risk assessment requires the best scientific
information about what the concentration of a chemical is in the
environment. In the absence of reliable and extensive monitoring data,
the concentration of a chemical can be estimated using one of several
fate models and data for the individual processes that may be dominant
for that chemical. These data may be measured in the laboratory,
obtained from literature sources, or estimated using appropriate
structure-activity relationships (SARs) or correlation methods. These
data used with environmental parameters in a mathematical model
constitute the process modeling approach (Baughman and Burns, 1980;
Baughman and Lassiter, 1978; Smith et al., 1977; Mill, 1978).
The Environmental Protection Agency's Office of Emergency and
Remedial Repsonse (OERR) is required to determine "reportable
quantities" (RQs) for various chemicals under Sections 101(14) and 102
of the Comprehensive Environmental Response, Compensation, and Liability
Act of 1980 (CERCLA). After promulgation, releases to the environment
of amounts of these chemicals in excess of the corresponding RQ must be
reported to a designated Federal organization (usually the U.S. Coast
Guard). The toxicity of each chemical is one of several factors
considered in determining an appropriate RQ. Earlier, scientists in the
Office of Health and Environmental Assessment (OHEA) summarized the
toxicological literature on these compounds for OERR. Since the
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transport and fate of these chemicals and their persistence in the
environment are also important factors in determining their potential
toxicity, Work Assignment 14 provides for a lit.erature search for 10
fundamental physical and chemical parameters for 82 compounds not
previously investigated in this fashion by the Agency. This information
will be analyzed to predict potential environmental transport and fate.
These data are to be used in a screening assessment to decide what
chemicals clearly would not persist in aquatic environments because of
exceptional reactivity and what environments may be of particular
concern because of dominant volatilization or sorption processes. This
information will also be used to decide what data gaps exist and what
particular process data need to be obtained for subsequent and more
detailed assessments.
The data are made available in this report with the expectation
that they may be of interest in other assessment efforts. Use of the
data in the context of other assessments requires that each user
understand the sources and limitations of the data. Each user must
decide what additional data are required for the particular
assessment. Any user of these data must particularly recognize that
some values were estimated by SRI staff with expertise in the process of
interest, and that considerable subjective judgment was applied for some
of the estimates. Such judgments based on even crude analogies are
indeed valuable and acceptable in screening level evaluations. In cases
where even expert judgment cannot be used to provide a value, no value
was entered. Users of these data are encouraged to conduct more
intensive literature searches or to consult other knowledgeable
scientists to augment or supplant data in this report.
In this report, "process data" are defined as data relating to rate
constants, equilibrium constants, or physical properties that describe
the intrinsic processes the chemicals may undergo independent of
environmental influences. "Environmental parameter" in this report
refers to properties or data that describe (or are a function of) the
environment.
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BACKGROUND
The processes that can be important for transforming or transport-
ing a chemical in an aquatic environment are shown in Figure 1.1. The
following discussion summarizes the mathematical basis for the process
modeling approach applied to aquatic systems: (1) the evaluation of
rates of loss of chemical due to transformations and volatilization
processes, (2) the influence of sorption processes on the rates of loss
of chemical, and (3) the prediction of concentration and half-life of
chemical in the aquatic environment, including terms for input of
chemical, dilution, and flow out of the environment. This discussion
assumes that sorption to particulates in the environment is not
kinetically controlled (i.e., sorption equilibrium is attained
instantaneously).
Inflow of
Chemical
Outflow of
Chemical
Volatilization
Organic Chemical
in Aquatic
Environment
Sorption/Desorption
to Particulates,
Chemical Transformations
Photochemistry
Hydrolysis
Oxidation
B ^transformations
Hydrolysis
Oxidation
Reduction, etc.
II
Sedimentation
FIGURE 1.1 TRANSPORT AND TRANSFORMATION PROCESSES IN
AQUATIC ENVIRONMENTS
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EVALUATION OF CHEMICAL LOSS RATES
The rate of loss of a chemical due to the above transformation
processes and volatilization, R.J., is given by the sum of the rates of
the individual processes, R^, according to the equation
RT - m± = n^'iEjic] (i.i)
where k^' is the rate constant for the i-th process, [E^] is an
environmental parameter that is kinetically important for the i-th
process, and [C] is the concentration of the chemical. The calculations
of R^ for individual processes from environmental parameter and process
data are discussed in subsequent sections. The important environmental
parameters for each process have been reviewed, and the use of the
parameters in the calculations of environmental transformation rates has
been discussed in detail by Baughman and Burns (1980), Mill (1978), and
Smith et al. (1977).
The above expression for R™ assumes that the loss of chemical is
first order in the chemical concentration, as certainly must be the case
at the highly dilute concentrations expected in the environment.
Equation (1.1) also requires that the rate of loss of chemical due to
any one process RJ is first order in the environmental parameter term
E.; R. is then considered as following overall second-order kinetic
behavior. If it is assumed that the low concentration of chemical in
the environment has no significant effect on the environment (for
example, does not change pH, biomass, dissolved oxygen, etc.) and that
the environmental parameter, E^, is constant over a specific region and
time period, the term k^' [EjJ can be expressed as a simple pseudo-
first-order rate constant, kj, and then
RT " [3^] [C] - kT[C] (1.2)
or
\ - B^ (1.3)
where kT is the overall pseudo-first-order rate constant for loss of
chemical due to transformation and volatilization. The half-life for
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loss of chemical due to these processes is then given by
Cl/2 = ln2/kT (1-4)
INFLUENCE OF SORPTION
In addition to losses of chemicals due to these transformation and
volatilization processes, sorption to particulates can also reduce the
concentrations of chemicals in aquatic systems. These particulates may
be either suspended sediments or biotic in.origin and the particulates
may eventually be deposited into benthic sediments. The suspended or
benthic sediment may later serve as a source of chemical from sorption-
desorption equilibrium as the chemical in solution volatilizes or
undergoes transformation in the water column. If biotransformation does
not occur in biota (such as bacteria, algae, and fish), the chemical may
be released back into solution when the organism dies and decomposes.
The understanding of chemical transformation when the chemical is sorbed
onto particulates is inadequate to predict or measure the rates of such
reactions for use in modeling. Therefore, the following discussion
assumes that no transformations occur on particulates and that sorption
is completely reversible and rapid in comparison with transformations
that occur in solution.
The partitioning of a chemical between particulates (sediment or
biota) and water at the low concentrations of chemicals usually found in
the environment can be expressed as a partition coefficient K^:
kp = Cs/Cw C1'5)
where Cs and Cw are the eauilibrium concentrations of chemical on
sediment and in water, respectively (Baughman and Lassiter, 1978; Smith
and Bomberger, 1982).
By convention, K_ is unitless when C is in units that are
equivalent to C^. (i.e., Cg is in g chemical/g particulate and Cw is in g
chemical/g water). In this discussion, [Cw] will be defined in these
weight units and [C] will be defined in molecular units (moles L"1");
because 1 g water is approximately 1 mL, it follows that fCl = IcPfC I
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where MW is the molecular weight of chemical. Note that [Cl and [Cwl
can be used interchangeably in expressions such as equation (1.2)
because first-order rate constants are concentration independent, but
the rate of loss term, R, is of course defined in units corresponding to
[Cw] or [C].
For a chemical in aqueous solution containing particulates, the
chemical is equilibrated between the water and particulate P according
to the relation
C + P , C-P (1.6)
and the partition coefficient can be rewritten as
, - [OP] „ _
where [C-P] is the mass of sorbed chemical per unit solution volume and
[P] is the mass of sorbing particulate per unit solution volume. The
mass balance of chemical in the solution-sediment system is given by
[CT] = [C-P] + [Cw]
(1.8)
where [C™] is the total mass of chemical in a unit solution volume of
water containing [P] grams of particulate. Combining equations (1.7)
and (1.8) then gives the fraction of the total chemical dissolved in
solution:
jfjj 1
[C 1 = K [PI + 1 (L-9>
T p
Baughman and Lassiter (1978) have pointed out that, given the relation-
ship shown in equation (1.9), the fraction of chemical in solution may
be quite high in spite of a large K value because the sediment or biota
loading, [P], is often low in aquatic systems (i.e., K^[P] < 1)
The concentration of chemical in sol
particulate-water system is then given by
The concentration of chemical in solution [C ] in the presence of a
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fP]K + 1
p
Substituting equation-(1.10) into equation (1.2) for the rate of loss of
chemical then gives
VT
R =
T fPlK +1 ^
P
This relationship shows that unless transformation on particulate is as
fast as or faster than that in solution, the net effect of sorption will
be to reduce the overall rate of loss of chemical from the aquatic
system. From equation (1.11), it also follows that the half-life of the
chemical is given by
(FP1K + I)ln2
The process modeling approach is then a valuable tool in risk
assessments. Although values of tj/2 or Cw can be manually calculated,
the calculations are more easily done using computer programs. One such
computer model is EXAMS, which allows the user to choose environmental
parameters and is able to accommodate chemicals when several processes
compete to be the important fate pathway. Computer models also allow
for sophisticated and environmentally realistic dynamic models to be
used rather than assuming steady-state conditions.
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REFERENCES
Baughman, G. L. , and L. A. Burns. 1980. Transport and Transformation of
Chemicals: A Perspective. In: The Handbook of Environmental Chem-
istry, Vol. 2, Part A. 0. Hutzinger, Ed. Springer-Verlag, New York.
Baughman, G. L., and R. R. Lassiter. 1978. Prediction of Environmental
Pollutant Concentration. In: Estimating the Hazard of Chemical
Substances to Aquatic Life. ASTM STP 657. J. Cairns, Jr., K. L.
Dickson, and A. W. Maki, Eds. American Society for Testing and
Materials, Philadelphia, PA.
Mill, T. 1978. Data Needed to Predict Environmental Fate of Organic
Compounds. Symposium on Environmental Fate held at American
Chemical Society Meeting, Miami, FL, September 1978.
Smith, J. H., and D. C. Bomberger. 1982. Volatilization from Water.
In: Laboratory Protocols for Evaluating the Fate of Organic Chem-
icals in Air and Water. EPA-600/3-82-022. U.S. EPA, Washington, DC.
Smith, J. H. , W. R. Mabeyj, N. Bohonos, B. R. Holt, S. S. Lee, T.-W. Chou,
D. C. Bomberger, and T. Mill, 1977. Environmental Pathways of
Selected Chemicals in Freshwater Systems. Part I. Background and
Experimental Procedures. EPA-600/7-77-113. U.S. EPA, Washington, DC.
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SECTION 2
DEFINITIONS OF PROCESSES AND SOURCES OF DATA
BASIS FOR DERIVATION OF DATA
The data on chemicals given in this report were obtained from the
literature and from calculations based on theory, SARs, or empirical
calculations. In general, the physical properties of a chemical are
functions of the molecular structure as an entity; that is, the
elemental composition, spatial relationships and size, molecular weight,
and functional groups of the molecule all may contribute to the property
of the chemical. In contrast, the chemical or biological reactivity of
a molecule is usually caused by selected functional groups in the
molecular structure, and the functional group may undergo transformation
with sometimes only minor changes in the total structure of the
molecule.
The individual processes that chemicals may undergo can then be
classified and evaluated according to specific physical properties or
the reactive functional groups that these chemicals may have in
common. The basis for the empirical correlations between KQW and Sw is
discussed in Section 4. These constants describe equilibrium processes
for the chemical between water and a second (organic) phase. Similarly,
the volatilization of a chemical can be evaluated in terms of Henry's
constants, which are functions of vapor pressure and water solubility.
The reactivity of a chemical can be classified according to select
functional groups in the molecular structure. For evaluations of
hydrolysis reactions, chemicals are classified as carboxylic acid esters
(-C02R), carboxylic acid amides (-CONH2), alkyl halides (R-X), and
phosphoric acid esters ((KO^PO), to name only a few. Data for
hydrolysis of a chemical can often be estimated by analogy to another
chemical with a similar functional group or calculated by more formal
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procedures using linear free-energy relationships such as the Taft
equation, the Hammett equation, or other such correlations (Mill, 1979;
Wolfe et al., 1978 and 1980).
Chemical oxidation rate constants can be calculated by evaluating
the reaction of an oxidant at a particular type of carbon-hydrogen bond
(i.e., hydrogen abstraction process) or at an olefinic bond. No SAR or
correlation method is available for predicting a direct photolysis rate
.constant except by analogy to other chemicals, which is often unreliable
because of the complex chemistry of photoexcited states.
For this report, data obtained from calculations involving theory,
SARs, or empirical correlations have been clearly identified so that the
user can recognize the source of such data and can recalculate data
using current or improved procedures.
The following briefly describes the environmental processes and the
process data important in aquatic fate assessments. The process data
are discussed in the order that they appear on the data sheets. The
sources of the process data are also discussed.
CHEMICAL NAME, CHEMICAL ABSTRACTS SERVICE REGISTRY NUMBER, AND MOLECULAR
WEIGHT
The names of the chemicals used on the data sheets are those as
given on the original EPA list. The Chemical Abstracts Service (CAS)
number has been obtained mainly from the original EPA list. Handbooks,
catalogs, or the CAS were used when necessary. The molecular weight
(MW) has been calculated from the molecular formula. Although the MW is
not used for environmental assessments, it is required for conversion of
units from ppm to molar units (M). The MW has also been used to
calculate the molecular weight/oxygen ratio.
WATER SOLUBILITY
Water solubility (Sw) data are required for calculating Henry's
constant and for calculating other partition coefficients using the
correlation equations discussed in Section 4. Values of Sw (ppm or
mg L"^-) were calculated from Kow using a correlation equation developed
by Yalkowsky and Valvani (1980).
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For organic pollutants that are liquid in their pure state at 25°C
log Sw = -1.08 log Kow + 3.70 + log MW (2.1)
where MW is the molecular weight of the pollutant (g mole~l). For
organic pollutants that are solid in their pure state at 25°C
AS-,
log Sw = -1.08 log Kow + 3.70 + log MW - (—|-)(mp - 25) (2.2)
where mp is the melting point of the pollutant (°C) and AS is the
entropy of fusion of the pollutant (cal mol deg ). If ASF is not
known, it may be approximated by
ASF ~ 13.6 + 2.5 (n - 5) (2.3)
where n is the number of flexible atoms (i.e., atoms not involved in
double bonds, triple bonds, or part of a ring structure) in the
pollutant molecule, other than hydrogen. If n is less than 5, n - 5 is
set equal to zero.
For solids that had no literature melting points available, Sw was
calculated using,the equation for liquids. This results in a maximum Sw
and should be used only for a screening risk assessment.
MELTING AND BOILING POINT
These data are not used directly in aquatic fate assessments, but
they show in which phase (gas, liquid, solid) the pure chemical is found
under environmental conditions. Boiling point data are cited for 760
torr (1 atmosphere) unless otherwise noted. The melting point should be
used in the calculation of water solubility from octanol/water partition
coefficient (Kow) data for compounds that are solids above 25°C.
VAPOR PRESSURE
The vapor pressure PV (torr) of an organic chemical is, in itself,
a qualitative or relative measure of the volatility of the chemical in
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Its pure state and can be used to calculate the Henry's constant used in
volatilization rate constant calculations. Unless otherwise specified,
the Pv values listed are at 25 °C.
Vapor pressure data not found in the literature were calculated
using procedures described by Grain (1982). The method uses a
modification of the Watson correlation to express the temperature
dependence of AH such that
[3 - 2(T/T )]m (2.4)
where AH is the heat of vaporization at temperature T, AH is the heat
of vaporization at the normal boiling point, and m is a constant that
depends upon the physical state. Substitution in the Clausius-Clapeyron
equation and integration results in an expression with adjustable
parameters that depend on the molecular structure, functional groups,
and physical state at the temperature of interest. With further
modification, the method can also be used to extrapolate vapor pressures
from one temperature to another.
This procedure has an estimated maximum error of 7.1% over the
pressure range 10-760 torr, 50% over 10~3-10 torr, and 200% below 10
torr. The average error is <50%, which is often less than the range of
Pvs found in the literature.
MOLECULAR WEIGHT TO OXYGEN RATIO
The molecular weight to oxygen ratio is used to estimate the
volatilization rate constant for a chemical (Mabey et al. 1983). The
ratio was calculated from the molecular weights of the chemical and
molecular oxygen (the latter is 32 g/mole).
OCTANOL/WATER PARTITION COEFFICIENT
The octanol/water partition coefficient KOW has been used in
medical and environmental science as a measure of the hydrophobicity/
hydrophillcity of chemicals (Hansch and Leo, 1979; Kenaga and Goring,
1978). The Kow values in this report were used to calculate Sw; Kow
values also are useful for estimating sediment and biota partitioning
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coefficients (see Section 4). The calculation of KQW from structural
features of the molecule is also discussed in Section 4.
HYDROLYSIS RATE CONSTANTS
Hydrolysis refers to reaction of a chemical with water, usually
resulting in the introduction of a hydroxyl function into a molecule and
loss of a leaving group -X:
R-X + H20 •- ROH + HX (2.5)
The hydrolyses of some classes of compounds are catalyzed by acid or
base, and therefore the hydrolysis rates of these chemicals in the
environment can be pH dependent. The subject of hydrolysis in aquatic
systems has been reviewed in detail by Mill et al. (1982), and an
extensive compilation of hydrolysis data was published in a review by
Mabey and Mill (1978).
The rate of hydrolysis of a compound at a specific pH value is
given by the equation
RH " kh[C] = (kA[H+] + kN + kB[OH~])[C] (2.6)
where k^ is the first-order rate constant for hydrolysis at the pH, k^
and kg are second-order rate constants for acid- and base-promoted
hydrolyses respectively, and kjj is the first-order rate constant for the
pH-independent, neutral hydrolysis process. Using the autoprotolysis
equilibrium expression
[H+HOH-] = Kw (2.7)
equation (2.6) can be rewritten as
kh = kA[H+]+kN+^ (2.8)
I" J
Equation (2.8) shows that k^ will depend on the pH of the aquatic system
and on the relative values of kA, kg, and kfl. At present, no reliable
information shows that hydrolysis rates in aquatic environments will be
catalyzed by species other than [H+] or [OH~].
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The hydrolysis rate constants kA, kg, and kN used to calculate kh
as a function of pH are described below along with the source codes for
calculating or estimating the values of the rate constants.
ACID-PROMOTED HYDROLYSIS RATE CONSTANT
The acid-promoted hydrolysis rate constant k^ (M"^h~^) is for the
acid-promoted hydrolysis of a chemical. In regions where only k/.
contributes to hydrolysis (i.e., kA[H+] » kN = kg[OH~]), kh will
decrease by a factor of 10 for each 1-unit increase in pH.
BASE-PROMOTED HYDROLYSIS RATE CONSTANT.
The base-promoted hydrolysis rate constant kg (M~-'-h~1) is for the
base-promoted (OH~) hydrolysis of a chemical. In regions where only kg
contributes to hydrolysis, kh will increase by a factor of 10 for each
1-unit increase in pH.
NEUTRAL-HYDROLYSIS RATE CONSTANT.
The neutral-hydrolysis rate constant kN (h~^) is for the pH-
independent hydrolysis of a chemical. Data or sources pertaining to the
hydrolysis of the organic chemicals have been entered in the data sheets
in several ways. When a chemical structure had Tap _hydrolyzable
functional _groups, NHFG was entered. When chemical hydrolysis occurs
only at extreme pH values or temperatures or with catalysts not
available in aquatic environments, HNES was entered (hydrolysis jipt
environmentally _signifleant). Other data for hydrolysis are referenced
or are based on analogy to similar chemicals.
MICROBIAL DEGRADATION RATE CONSTANT
Biotransformations are undoubtedly important processes for
degradation of chemicals in aquatic environments, resulting in
hydrolysis, oxidation, and reduction of the chemical structure to
ultimately produce carbon dioxide and water. The complex factors
influencing the biotransformation of a chemical include pH, temperature,
dissolved oxygen, available nutrients, other organic chemicals
(synthetic or naturally occurring) that may serve as cometabolites or
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alternative energy sources, and the populations and types of organisms
capable of transforming the chemical. For most assessments, the initial
biotransformation step is of prime importance (i.e., removal of the
specific chemical from the environment). However, the biotransformation
process is still too complex to be used to reliably predict a
biotransformation rate constant using theoretical approaches such as
those available for chemical and physical processes.
Maki et al. (1980) recently reviewed some of the aspects of the
measurement of biotransformation rates and the use of such data. The
rates of biotransformation are complex functions of chemical concen-
tration and microbial biomass. However, at the typical concentrations
of a chemical in the environment (< 1 ppm), the rates may be expected to
follow second-order kinetics because they are first order in chemical
kinetics and first order in biomass kinetics. Furthermore, the
microorganism growth due to consumption of the chemical may not be
significant; therefore, the rates of biotransformation are pseudo-first-
order as a function of the chemical concentration.
The biotransformation data given in this report were estimated for
the approach described by Baughman et al. (1980), in which the rate of
biotransformation of a chemical, RB, is given by the expression
RB = - kb[B][C] (2.9)
where k^ is a second-order rate constant for biotransformation of a
chemical by bacteria of population [B] in the solution phase of the
water column. When k^ is given in mL cell"1 h"1, the units of [B] are
in cell mL'1. Because data for k^ were not available for most chemicals
covered by this report, the rate constants were estimated solely for use
in aquatic fate modeling by EPA. These data were estimated using on
relative rates of biodegradation of the chemicals as reported in
literature, structural analogies, and judgment of SRI staff with
expertise in biotransformation studies. These data have been estimated
and appropriate caution should be exercised in the use of the data.
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PHOTOLYSIS RATE CONSTANT
The direct photolysis rate constants kp (h~^) f°r most of the
chemicals cannot be estimated because of insufficient spectral and
quantum yield data. For chemicals where no light absorption occurs
above the solar cutoff (300 nm), the rate constant can be considered as
zero, and therefore photolysis is _npt ^environmentally jrelevant (NER).
In cases where the chemical is expected to photolyze in the
environment but no data are available, no value is entered. Similarly,
no value is entered if nothing is known about a chemical's photolytic
reactivity. No data for indirect photolysis of chemicals is provided in
this report except that which results from oxidation processes (see next
section).
OXIDATION RATE CONSTANTS
Chemical oxidation of organic chemicals in aquatic environments may
be caused by several different oxidants, among which are singlet oxygen
( °2^» alkyl peroxyl radical (R02*), alkoxy radical (R0»)> or hydroxyl
radical («OH). The source of these oxidants is primarily photochemical,
but because the oxidants react with chemicals in their ground state, and
oxidation therefore does not involve the photochemistry of the chemical
itself, oxidations are reasonably considered as discrete processes apart
from photochemistry. Each oxidant has a unique reactivity toward
organic moieties, and the relative and absolute concentrations of these
oxidants will vary with environmental parameters, such as concentration
and origin of humic-fulvic materials and sunlight intensity.
Literature Information classifies reported data on oxidation of
organic chemicals by oxy radicals such as R0~» and ^02. The laboratory
study conducted by Mill et al. (1982) using natural waters indicates
—9
that R02» radical concentrations of ~ 1 x 10 M may be present in the
surface waters of sunlit water bodies. Oxidation reactions initiated
by RO • include the following:
16
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R02« + -C-H -R02H + -O (2.10)
R02« + C=C «-R02-C-0 (2.11)
R02» + ArOH » R02H + ArO' (2.12)
R02» + ArNH2 *. R02H + ArNH (2.13)
Of these reactions, the last two are quite rapid in aquatic environments
(tl/2 ^ several days), whereas the others are slower and usually will
not be important for most chemicals.
Zepp et al. (1978) have shown that ^C^ can be formed at
» 1 x 10~12 M concentrations in sunlit natural waters. The most
important reactions for 02 with organic chemicals are those involving
reaction with olefinic moieties (Ranby and Rabek, 1978).
o0 +^rc=c. »• -C-C=CH
2 -" ^ . |i
OOH
H - . (2.14)
r products
I I
0-0
Some rate constants for ^^ and R0_« are listed in a review by Mill
(1980).
The rate of loss of organic chemicals RQ^ by oxidation is
ROX = ^0 JR02*][C] + kl [lo2ltC] + koX[OX1[C] <2
2 02
where kgx and [OX] are the rate constants and concentration values for
other unspecified oxidants. Only data for the second-order rate
constants k and k have been estimated for this report. When two
R°2* ^2
rate constants are given on the data sheets, the second-order rate
constants should be multiplied by their respective oxidant concentra-
tions to determine which of the first-order rate constant values is
larger, and that rate constant should be used for an assessment.
17
-------
Apart from a direct measurement of a rate constant at a specific
temperature (which is rare), most rate constants in this report were
obtained either from extrapolation of a rate constant for the organic
chemical measured at another temperature or from a correlation of
structure with reactivity as discussed below.
RATE CONSTANT FOR OXIDATION BY ALKYL PEROXYL RADICAL
Because many chemicals on the list of chemicals of concern have
several kinds of reactive centers for oxidation by RO •, the overall
rate constant k (M~^h~*)was obtained by first calculating the
individual rate constants for each reactive site and then summing these
rate constants. For example, acrolein has two reactive sites: (1)
addition to the double bond and (2) H-atom transfer from the carbonyl
k
R02« + CH2=CHCHO - = - -R02C-C-CHO (2.16)
RO- + CH2=CHCHO - - - ^CH2=CHCO + R02H (2.17)
kR02 = kl + k2 (2.18)
When one oxidation process was found to be fast, the important oxidant
was listed and the other reactions were ignored. When there were more
than one -CH bond of a given kind, the rate constant was multiplied by
the number of similar -CH bonds to give the correct total rate constant
for oxidation of that CH-bond.
Two procedures were used to calculate individual kg™ values
for RO • reactions. In the first, when a structure was analogous to
another chemical structure with a measured rate constant at a similar
temperature, the measured rate constant was used directly (Hendry et
al., 1974). (The -CHO bond in acrolein is an example.) The second
procedure, used most often, is based on SARS established by Howard and
coworkers for H-atom transfer (Korcek et al., 1972) and addition to
double bonds (Howard, 1972), as shown below.
For the H-atom transfer reaction
log kRQ = 18.96 - 0.2[D(R-H)] (2.19)
18
-------
where D(R-H) is the bond dissociation energy of the CH-bond.
For the R02 addition to double bonds
log k^Q - [16.54 - 0.2D(XCR2-H)]70.75 (2.20)
where D(XCR2~H) is the bond dissociation energy of a species that gives
the radical formed by R02 addition and where R02 is assumed to have the
same effect as methyl (Me) on D(C-H). Thus for "oxidation of vinyl
chloride
x ^ ^
RV + ^C=C^ R02 (2.21)
the closest analog would be MeCH2CHCl, and the value of D(MeCH2CHCl-H)
would be used in equation (2..20). Bond dissociation energies were taken
from Furuyama et al. (1969).
RATE CONSTANT FOR OXIDATION BY SINGLET OXYGEN
Only a few of the chemicals tabulated in this report are reactive
toward 02» these include some polycyclic aromatic and a few olefinlc
double bond or diene systems. All reactive chemicals were assigned rate
constants by analogy with similar structures that have shown rate
constants for reaction with singlet oxygen. For cyclic olefins, the
values of Matsuura et al. (1973) were used. For alicyclic olefins and
other structures, the rate data summarized by Gollnick (1978) were used.
19
-------
REFERENCES
Baughman, G. L., D. L. Paris, and W. C. Steen. 1980. Quantitative
Expression of Bio.transformation Rate. In: Biotrans'formation and
Fate of Chemicals in Aquatic Environments. A. W. Maki, K. L. Dickson,
and J. Cairns, Jr., Eds. American Society for Microbiology, Wash-
ington, DC.
Furuyama, S., D. M. Golden, and S. W. Benson. 1969. J. Am. Chem. Soc.
.91, 7564-7569.
Gollnick, K. 1978. In: Singlet Oxygen, B. Ranby and J. F. Rabek, Eds.
John Wiley and Sons, New York.
Grain, C. 1982. Vapor Pressure. In: Handbook of Chemical Property
Estimation Methods. W. J. Lyman, W. F. Reehl, D. H. Rosenblatt,
Eds. McGraw-Hill Book Company, New York.
Hansch, C., and A. Leo. 1979. Substituent Constants for Correlation
Analysis in Chemistry and Biology. Wiley-Interscience, New York.
Hendry, D. G., T. Mill, L. Piszkiewicz, J. A. Howard, and H. K. Eigenmann.
1974. J. Phys. Chem. Ref. Data. _3, 937-978.
Howard, J. A. 1972. Adv. Free Radical Chem. 4^ 49-174.
Kenaga, E.-E., and C. A. I. Goring. 1978. Relationship Between Water
Solubility, Soil-Sorption, Octanol/Water Partitioning, and Bio-
concentration of Chemicals in Biota. In: Aquatic Toxicology, ASTM
STP 707, J. G. Eaton, P.. R. Parrish, and A. C. Hendricks, Eds.
American Society for Testing and Materials, Philadelphia, PA.
Korcek, S., J. H. B. Chenier, J. A. Howard, and K. U. Ingold. 1972.
Can J. Chem. J50, 2285-2297.
Mabey, W. R. , and T. Mill. 1978. J. Phys. Chem. Ref. Data. _7> No- 2»
383-415.
Mabey, W. R., T. Mill, and R. T. Podoll. 1983. Estimation Methods for
Process Constants and Properties Used in Fate Assessments. Final
Report for Work Assignment No. 5 in partial fulfillment of EPA
Contract No. 68-03-2981, U. S. EPA, Athens, GA.
Maki, A. W., K. L. Dickson, and J. Cairns, Jr., Eds. 1980. Biotrans-
formation and Fate of Chemicals in Aquatic Environments. American
Society for Microbiology, Washington, DC.
Matsuura, T., A. Horinaka, and R. Nakashima. 1973. Chem. Lett. 887-890.
Mill, T. 1979. Structure Reactivity Correlations for Environmental
Reactions. EPA-560/11-79-012. U.S. EPA, Washington, DC.
20
-------
REFERENCES
Mill, T. 1980. Photooxidation in the Environment. In: The Handbook
of Environmental Chemistry, Vol. 2, Part-A. 0. Hutzinger, Ed.
Springer-Verlag, New York.
Mill, T., W. R. Mabey, and D. G. Heridry. 1982. Hydrolysis in Water.
In: Laboratory Protocols for Evaluating the Fate of Organic
Chemicals in Air and Water. EPA-600/3-82-022. U.S. EPA, Washington.
Ranby, B., and J. F. Rabek, Eds. 1978. Singlet -Oxygen. John Wiley and
Sons, New York.
Wolfe, N. L., L. A. Burns, and W. C. Steen. 1980. Chemosphere. J9,
393-402.
Wolfe, N. L., R. G. Zepp, and D. F. Paris. 1978. Water Res. 12, 561-563.
Yalkowsky, S. H., and S. C. Valvani. 1980. J. Pharm. Sci. 69, No. 8,
912-922.
Zepp, R. G., N. L. Wolfe, G. L. Baughman, and R. C. Hollis. 1978. Nature.
267, 421-423.
21
-------
SECTION 3
DATA SHEETS FOR CHEMICALS OF INTEREST
This section contains a list of data sheets showing the Chemical Abstract
Services registry number and compound name, a list of source codes for the
data sheets, and the data sheets and references for this work assignment.
22
-------
LIST OF DATA SHEETS
CAS
Number Registry Ndmber
1 62-44-2
2 53-96-3
3 1402-68-2
4 148-82-3
5 92-67-1
6 61-82-5
7 7778-39-4
8 492-80-8
9 115-02-6
10 151-56-4
11 50-07-7
Compound Name
12
13
14
15
16
17
18
19
56-49-5
225-51-4
57-97-6
3165-93-3
60-11-7
101-14-4
636-21-5
99-55-8
20
21
22
23
24
25
510-15-6
94-59-7
120-58-1
94-58-6
82-68-8
13597-99-4
Acetamide, N-(ethoxyphenyl)-
Acetamide, N-9H-fluoren-2-yl-
(2-Acetamidofluorene)
Aflatoxin
Alanine, [p-bis(2-chloroethyl)amino]phenyl-, L-
4-Aminobiphenyl
Amitrole
(3-Amlno-l,2,4-triazole)
Arsenic acid
Auramine
Azaserine
Aziridine
(Ethyleneimine)
Azirino(2',3f:3,4)pyrrolo(l,2-a)indole-4,7-
dionen,6-amino-8-[((aminocarbonyl)oxy)methyl]-
1 ,la,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-
(Porifomycin)
Benz[j]aceanthrylene, 1,2-dihydro-3-methyl-
Benz[c]acridine
1,2-Benzanthracene, 7,12-dimethyl-
Benzenamine, 4-chloro-2-methyl-, hydrochloride
Benzenamine, N, N-dimethyl-4-phenylano-
Benzenamine, 4,4'-methylenebis(2-chloro-)-
Benzenamine, 2-methyl-, hydrochloride
Benzenamine, 2-methyl-5-nitro-
(2-Amino-4-nitrotoluene)
Benzeneacetic acid, 4-chloro-alpha-
(4-chlorophenyl)-alpha-hydroxy-, ethyl ester
(Chlorobenzilate)
Benzene, 1,2-methylenedioxy-4-allyl-
(Safrole)
Benzene, 1,2-methylenedioxy-4-propenyl-
(Isosafrole)
Benzene, 1,2-methylenedioxy-4-propyl-
(Dihydrosafrole)
Benzene, pentachloronitro-
Beryllium nitrate
23
-------
LIST OF DATA SHEETS (continued)
CAS
Number Registry Number
Compound Name
26
27
28
29
30
31
32
33
34
35
1464-53-5
119-93-7
119-90-7
305-03-3
8001-35-2
51-79-6
615-53-2
759-73-9
684-93-5
62-56-6
2,2'-Bioxirane
(l,l'-Biphenyl)-4,4'-diamine, 3 , 3 ' -dimethoxy-
( 1 , 1 ' -Biphenyl) -4,4' -diamine , 3,3' -dime thy 1-
(o-Tolidine)
Butanoic acid, 4-[bis(2-chloroethyl)amino]
benzene-
Camphene, octachloro-
Carbamic acid, ethyl ester
(Ethyl carbamate urethane)
Carbamic acid, methylnitroso-, ethyl ester
Carbamide, N-ethyl-N-nitroso-
Carbamide, N-methyl-N-riitroso-
Carbamide, thio-
(Thiourea)
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
79-44-7 Carbamoyl chloride, dimethyl-
494-03-1 Chloronaphazine
106-89-8 l-Chloro-2,3-epoxypropane
(Epichlorohydrin)
50-18-0 Cyclophosphamide
20830-81-3 Daunomycin
2303-16-4 Diallate
302-01-2 Diamine
(Hydrazine)
95-80-7 2,4-Diaminotoluene
189-55-9 l,2:7,8-Dibenzopyrene
96-12-8 1,2-Dibromo-3-chloropropane
692-42-2 Diethylarsine
123-91-1 1,4-Diethylene dioxide
(p-Dioxane)
57-14-7 1,1-Dimethylhydrazine
1615-80-1 N,N'-Diethylhydrazine
56-53-1 Diethylstilbestrol
77-78-1 Dimethyl sulfate
25321-14-6 Dinitrotoluenes
602-01-7 2,3-Dinitrotoluene
619-15-8 2,5-Dinitrotoluene
610-39-9 3,4-Dinitrotoluene
24
-------
LIST OF DATA SHEETS (continued)
CAS
Number Registry Mimber
Compound Name
56
57
58
59
60
61
62
63
64
65
122-39-4
55-18-5
62-55-5
1116-54-7
4549-40-0
106-93-4
75-21-8
62-50-0
9004-66-4
18883-66-4
N, N-Diphenylamine
Ethanamine, N-ethyl-N-nitroso-
Ethanethioamide
Ethanol, 2,2'-(nitrosoimino)bis-
Ethenamine, N-methyl-N-nitroso-
Ethylene dibromide
Ethylene oxide
Ethyl methanesulfonate
Ferric dextran
D-Glucopyranose, 2-deoxy-2-(3-methyl-3-
nitrosoureido)-
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
765-34-4 Glycidylaldehyde
70-25-7 Guanidine, N-nitroso-N-methyl-N'-nitro-
143-50-0 Kepone
303-34-4 Lasiocarpine
75-55-8 2-Methylaziridine
(Propyleneimine)
505-60-2 Mustard Gas
72-57-1 2,7-Napththalenedisulfonic acid, 3,3'-[(3,3'-
dimethyl-(l,l'-biphenyl)-4,4'-diyl)-bis(azo)]
bis(5-amino-4-hydroxy)-tetrasodium salt
134-32-7 1-Naphthylamine
91-59-8 2-Naphthylamine
13463-39-3 Nickel carbonyl
100-75-4 N-Nitrosopiperidine
930-55-2 N-Nitrosopyrrolidine
1120-71-4 1,2-Oxathiolane, 2,2-dioxide
50-06-6 Phenobarbital
126-72-7 1-Propanol, 2,3-dibromo-, phosphate (3:1)
[tris(2,3-Dibromopropyl)phosphate]
75-86-5 Propanenitrile, 2-hydroxy-2-methyl-
(Acetone cyanohydrin)
72-54-8 TDE
(1,1-Dichloro-2,2-bis(p-chlorophenyl)ethane)
66-75-1 Uracil, 5-[bis(2-chloroethyl)amino]-
(Uracil mustard)
25
-------
Calc
CC-Kow
C-Sw f Kow
C-vp f bp
E-A-Azirldine
LIST OF SOURCE CODES
Molecular weight/oxygen ratio was calculated directly.
Value of the octanol/water partition coefficient (KQW) was
obtained by computer calculation using FRAGMENT calculation
procedure (see Section 4.4).
The water solubility (Sw) was calculated from the
octanol/water partition coefficient (K. ) using the
equation of Yalkowsky and Valvani (1980); the calculation
of Sw values is discussed in Section 2.
Vapor pressure (vp) was calculated from the boiling point
(bp) using the method discussed by Grain (1982); the method
is discussed in Section 2.
Estimate by analogy to aziridine; hydrolysis data for
aziridine from Mabey and Mill (1978) or from Earley et al.
(1958).
E-A-Dibromopropane Estimate by analogy to dibromopropane; hydrolysis data for
dibromopropane from Vogel (1983).
E-A-Glycirdol
E-A-Naled
E-A-NM
E-KB
HF-NBD
HNES
Estimate by analogy to glycirdol; hydrolysis data for
glycirdol from Mabey and Mill (1978).
Estimate by analogy to Naled; hydrolysis data for Naled
from Jentzsch and Fischer (1978).
Estimated by analogy to nitrogen mustards; hydrolysis data
for nitrogen mustards from Ross (1949) indicates a maximum
half-life of 8 hours in aquatic environments •
Estimate of biotrans formation rate constant (k0) is
on relative rates of transformation reported in literature
or on structure-reactivity analogies.
Hydrolysis is too fast for biotransformation studies to be
conducted. Therefore, no biotransformation data are
available.
Hydrolysis is not environmentally significant • Chemical
hydrolysis occurs only at extreme pHs or temperatures or
with catalysts not available in aquatic environments.
26
-------
INERT
M-OX
NBD
NHFG
OX
partial
PNER
R02
SO
VF-NBD
Oxidation reactions at ambient oxygen levels have half-life
greater than 2 years and are therefore considered
unimportant fate processes.
Oxidation rate constants were modelled using functional
group reactivity toward alkyl peroxyl radical (R02) and
singlet oxygen (SO).
No biotransformation data are available.
No hydrolyzable functional groups in molecule.
Oxidation rate constants are experimental values.
Partial notation indicates that the computer calculated
octanol/water partition coefficient has not accounted for
each functional moiety of the molecule. This occurs when a
substituent fragment is not represented in the data base or
when there are possible hydrogen bonding interactions.
Photolysis is not environmentally relevant.
Alkyl peroxyl radical, R02*
Singlet oxygen, ^2
Volatilization is too fast for biotransformation studies to
be conducted. No biotransformation data are therefore
available.
27
-------
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
OC2H5
Compound Name: Acetamide, N-(ethoxyphenyl)-
CAS Registry Number: 62-44-2
-Molecular Weight (g):
179.22
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Reference
Alkaline
Constant
Hydrolysi
(M-ihr'1)
is Rate
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr"1)
Microbial Degradation 1
Rate Constant (ml cell hr" )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M~ hr~ )
578
134-135
6.9 x 10~7
5.60
1.76
HNES
HNES .
3 x 10~9
INERT
C-Sw f Kow
Merck (1976)
Wiedemann (1972)
Gale
CC-Kow
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
28
-------
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H
N-C-CHj
Compound Name: Acetamide. N-9H-fluoren-2-yl- (2-Acetamidofluorene)
CAS Registry Number; 53-96-3
-Molecular Weight (g):
223.28
Parameters;
Water Solubility (ppra)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation -
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr'1)
Oxidation Rate Constant (M~1hr~ )
Reference
6.5
192-196
6.98
3.28
HNES
HNES
-9
3 x 10
INERT
C-Sw f Kow
Aldrich (1982)
Calc
CC-Kow
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
29
-------
o o
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
CH,
Compound Name: Aflatoxin
CAS Registry Number; 1402-68-2
-Molecular Weight (g).:
312
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (OctanoI/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M~ hr~ )
Reference
993
268-269
9.75
0.71 (partial)
1 x ID'10
2 x 1010
C-Sw f Kow
Merck (1976)
Calc
CC-Kow
E-KB
M-OX SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
30
-------
u u / Nv .CHjCHjCI
EPA CONTRACT 68-03-2981 HooC-C-e -/fYS-N
WORK ASSIGNMENT NO. 14 jQ? "V-v" X
Compound Name: Alanine, [p-bis(2-chloroethyl)amino]phenyl-, L-
CAS Registry Number: 148-82-3 Mnlenilar Weieht(e): 305.20
Parameters: Reference
Water Solubility (ppm) 22
Melting Point (°C) 180-181
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen 9.54
Log (Octanol/Water Partition 1.20
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant QM hr )
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation _g
RatP C.n-^srant (ml r-f»1 1 hr~ ) ^ 3 X 10
Oxidation Rate Constant (M'^r'1) unknown
C-Sw f Row
Merck (1976)
Calc
CC-Kow
EA-NM
EA-NM
EA-NM
E-KB
-
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
(a) Aryldialkyl amines react with R02 by electron-, not H-transfer.
31
-------
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: 4-Aminobiphenyl
CAS Registry Number; 92-67-1
-Molecular Weight (g).:
169.23
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M^lir"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .,
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
842
53
302
6.0 x 10~5
5.29
2.78
NHFG
NHFG
NHFG
3 x 10~9
2 x 106
C-Sw f Kow
Verschueren (1977)
Weast (1981)
C-VP f bp
Calc
CC-Kow
E-KB
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
32
-------
NH2
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Amitrole ( 3-Amino-1,2,4-triazole)
CAS Registry Number; 61-82-5
-Molecular Weight(g):
84.08
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M hr'1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation 1
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
Reference
2.8 x 105/25°C
159
2.66
-2.08
1 x 10-10
2 x 106
Spencer (1973)
Merck (1976)
Calc
CC-Kow
E-KB
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
33
-------
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H3As04- Vi H20
Compound Name: Arsenic acid
CAS Registry Number; 7778-39-4
-Molecular Weight (g):
150.9
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M'-'-hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation 1
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M-1hr~ )
Reference
35.5
loses H20 at 160°
non-volatile
4.72
hydrated in
solution
INERT
Hawley (1977)
Hawley (1977)
Spencer (1973)
Gale
NBD
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
34
-------
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Auramine
CAS Registry Number; 492-80-8
-Molecular Weight (g).:
267.38
Parameters;
Water Solubility (ppm)
Melting Point C°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M'-hir"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant
Reference
2.1
136
8.34
4.16 (partial)
1 x 10-10
unknown
C-Sw f Kow
Weast (1973)
Calc
CC-Kow
E-KB
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
(a) Aryldialkyl amines react with R02 by electron-, not H-atom transfer.
35
-------
EPA CONTRACT 68-03-2981 HN=N_CH —C-
WORK ASSIGNMENT NO. 14 II
O
NH20
Compound Name: Azaserine
CAS Registry Number; 115-02-6
-Molecular Weight (g).:
173.13
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant '
Acid Hydrolysis Rate
Constant (M hr-1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M~1hr~ )
Reference
1.36 x 105
146-162 (dec)
5.41
-1.08 (partial)
3 x 10~9
INERT
C-Sw f Row
Merck (1976)
Calc
CC-Kow
E-KB
M-ox Ro?r sn
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
36
-------
10
H
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
/
HzP -
Compound Name: Aziridine (Ethyleneimine)
CAS Registry Number; 151-56-4
-Molecular Weight (g):
43.07
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant '
Reference
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation .
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant
2.66 x 106
56-57
255
1.35
-1.01
HNES
1.87 x Iff3
2.5 x 10~3
1 x 10~?
PNER
INERT
C-Sw f Kow
Merck (19.76)
Osborn and Scott (1980)
Calc
CC-Kow
Mabey & Mill (1978)
Earlevpf- nT . HQSSI
E-KB
M-nx R02. SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
37
-------
11.
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Azirino (2 ' , 3 ' : 3 , 4)pyrrolo (1, 2-a) indole-4 , 7-dionen, 6-amino-8-
Compound Name: [ ((aminocarbonv^oxy^ethyll-l.la^.S.SaiSb-hexahvdro-Sa-methQxy-
CAS Registry Number:
50-07-7
Weight (g):
348.35
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M^hr"1)
Reference
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation _ -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M hr~ )
1.6 x 106
201-201.5 (dec)
10.89
-2.19'
HNES
2.2 x 10~3
2.5 x 10~3
1 x lO'10
INERT
C-Sw f Row
Merck (1976)
Calc
CC-Kow
E-A-Aziridine as cited in
Mabey and Mill (1978)
E-A-Aziridine as cited in
Mabey and Mill (1978)
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
38
-------
12
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Benz[j]aceanthrylene, 1,2-dihydro-3-methyl-
CAS Registry Number; 56-49-5 Mplecular Weight(g) : 268.34
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M^br'1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant
Reference
1.15 x 10~3
179-180
280/80 torr
3.8 x 10"6
8.39
6.97
NHFG
NHFG
NHFG
3 x ID'12
2 x 108
C-Sw f Kow
Merck (19.76)
Merck (1976)
C-VP f bp
Calc
CC-Kow
E-KB
M-OX SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
39
-------
13
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Bpnz[c]acridlne
Parameters:
Water Solubility
Boiling Point (°
Coefficient)
Constant
> .
Constant (M~ hr-1
Constant (hr )
Rate Constant
umber: 225-51-4 Molemlar weight
1 A
ty (ppm)
re,
(torr)
ht/Oxygen 7-16
ater Partition 4,55
lysis Rate
r"1) NHFG
s_R*te NHFG
ysis Rate
) NHFG
adation _1 _1 io~12
> Constant (M^hr'1) INERT
r^: 229
Reference
C-Sw f Kow
Calc
CC-Kow
E-KB
M-OX R02. SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
40
-------
14
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: 1^2-Benzanthracene. 7,12-dimethyl-
CAS Registry Number; 57-97-6
-Molecular Weight (g):
256.33
Parameters:
Water Solubility (ppra)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Reference
Hydrolysi
(M-ihr"1)
is Rate
Alkaline
Constant
Acid Hydrolysis Rate
Constant (M~ hr-1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M hr~ )
4.40 x 10~3
121-123
8.01
6.94
NHFG
NHFG
NHFG
3 x 10~12
2 x 108
C-Sw f Kow
Alrich (1982)
Calc
CC-Kow
E-KB
M-OX SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
41
-------
15
NH, - HCI
CH,
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Cl
Compound Name: 'Bpngf>namlne> 4—chloro-2-methyl—. hydrochlorlde
CAS Registry Number; 3165-93-3 Molecular Weight(g): 176
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M~ hr~ )
Reference
1400
5 50
2.58 (partial)
NHFG
NHFG
NHFG
1 x 10-10
INERT
C-Sw f Kow
Gale
rn-Kow
.
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
42
-------
16
EPA CONTRACT 68-03-2981 //\>
WORK ASSIGNMENT NO. 14 \ /
Compound Name: Benzenamine, N,N-dimethyl-4-phenylano-
CAS Registry Number; 60-11-7 Molecular Weight(g).;
225.28
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M'-hir"1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant
Reference
13.6
114-117
3.3 x 10~7
7.04
3.72 (partial)
-NHFG
NHFG
NHFG
3 x 10-12
unknown
C-Sw f Row
Merck (1976)
Green and Jones (1967)
Calc
CC-Kow
E-KB
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
(a) Aryldialkyl amines react with R02 by electron, not H-atom transfer.
43
-------
17
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Benzenamine, 4,4'-methylenebis(2-chloro-)-
CAS Registry Number; 101-14-4 Molecular Weight (g):
232
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
1700
7.25
2.62 (partial)
NHFG
NHFG
NHFG
3 x 10-12
4 x 106
C-Sw f Row
Calc
CC-Kbw
-------
18
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Benzenamine, 2-methyl-, hydrochloride
CAS Reeistrv Number: 636-21-5 Mni«M,inr we-fEhf
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weieht/Oxvsen 4.44
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M-^-hr'1) NHFG
Acid Hydrolysis Rate NHFG
CouslduL (M lu ) ...
Neutral Hydrolysis Rate
Constant (hr~r) NHFG
Microbial Degradation . -in"10
Rafo rnnsfaTil- (ml r.«.n~1hr~±) 1 X 10
Oxidation Rate Constant (M'^r'1) INERT
Ce): 142
Reference
Calc
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
45
-------
19
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Benzenamine. 2-methvl-5-nitro- C2-Amino-4-nttrotoluene)
CAS Registry Number; 99-55-8 Molecular Weight (g): 152
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Reference
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
1.3 x 105
107-108
4.75
-0.06 (partial)
NHFG
NHFG
NHFG
1 x 10-10
2 x 106
C-Sw f Kow
Weast (1973)
Calc
CC-Kow
E-KB
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
46
-------
20
OH
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
COOCjH,
Benzeneacetic acid, 4-chloro-alpha-(4-chlorophenyl)-alpha-
Compound Name: hvdroxv-. ethyl ester (chlorobenzilate)
CAS Registry Number; 510-15-6
-Molecular Weight (g):
325.20
Parameters:
Water Solubility (ppm)
Melting Point
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M'-hir'1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
Reference
21.9
35-37
146-148/0. 04 torr
1.2 x 10~6/25°C
2.2 x 10~6/20°C
10.2
4.51 (partial)
1 x ID'10
INERT
C-Sw f Kow
Spencer (1973)
Merck (1976")
C-VP f bp
Merck C1976')
Calc
CC-Kow
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
47
-------
21
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
.CH2CH=CH2
Compound Name: Benzene. 1.2-methvlenedioxv-4-allvl- (Safrole)
CAS Registry Number; 94-59-7 Molecular Weight(g): 162.18
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M^hr'1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr" )
insoluble
1500
11.2
234.5
9.1 x 10
-2
5.07
2.53
NHFG
NHFG
NHFG
1 x 10
-10
2 x 10
10
Reference
Hawley -(1977)
C-Sw f Kow
Weast (1973)
Weast (1973)
C-vp f bp
Calc
CC-Kow
E-KB
M-OX SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
48
-------
22
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Benzene, 1,2-methylenedioxy-4-propenyl-
(Iso'safrole)
CAS Registry Number; 120-58-1 Molecular Weight (g):
162.18.
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Reference
Acid Hydrolysis Rate
Constant (M hr'1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M^lir
1.09 x 103
253
_o
1.6 x 10 (extrap)
5.07
2.66
NHFG
NHFG
NHFG
1 x 10-10
2 x 1010
C-Sw f Kow
Merck (1976)
Merck (1976)
Calc
CC-Kow
E-KB
M-OX SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
49
-------
23
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
CH2CH2CHj
Compound Name: Benzene, 1,2-methylenedioxy-4-propyl- (Dihydrosafrole)
CAS Registry Number; 94-58-6
Molecular Weight (g):
164.2
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (OctanoI/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~-1-hr~1)
Acid Hydrolysis Rate
Constant (M'^r"1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr~l)
Oxidation Rate Constant (M hr~ )
Reference
1500
5.13
2.54
NHFG
NHFG
NHFG
1 x 10-10
2 x 101Q
C-Sw f Kow
Calc
CC-Kow
E-KB
M-OX SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
50
-------
24
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Benzene, pentachloronitro-
CAS Registry Number; 82-68-8
-Molecular Weight (g):
295.36
Parameters;
Water Solubility (ppm)
Melting Point C8C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (OctanoI/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M~1hr~1)
Neutral Hydrolysis Rate
Constant
Microbial Degradation
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr" )
Reference
7.11 x 10~2
146
328
1.8 x 10~6
1.13 x 10~4
9.23
5.45 (partial)
NHFG
NHFG
NHFG
1 x 10-10
INERT
C-Sw f Kow
Verschueren (19.77)
Merck (1976)
C-Vp f bp
Spencer (1973)
Calc
CC-Kbw
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
51
-------
25
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Beryllium nitrate
CAS Registry Number: 13597-99-4 Molecular Weight (g):
187.1
Parameters;
Water Solubility (ppm)
Melting Point C°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M~1hr~ )
Reference
1
60
100-200 (dec)
5.85
dissociates
in solution
INERT
Merck (1976)
Hawley (1977)
Calc
a
NBD
M-OX R02. SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
52
-------
26
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: 2. 2f-Bioxirane
CAS Registry Number; 1464-53-5
-Molecular Weight (g):
86.09
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M hr-1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr'1)
Oxidation Rate Constant (M hr )
Reference
1.07 x 107
138
6.9
2.69
-1.29
HNES
8.9
1.02 x 10~3
INERT
C-Sw f Kow
Merck (1976)
C-VP f bp
Calc
CC-Kow
E-A-Glycirdol
E-A-Glycirdol
NBD
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
53
-------
27
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: (l.l'-BiphenyD-A^'-diamine, S.S'-dlmethoxy-
CAS Registry Number; 119-93-7 Molecular Weight(g): 244.28
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant '
Reference
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
430
137-138
7.63
1.78
NHFR
NHFG
NHFG
3 x ID'12
4 x 106
C-Sw f Kow
Merck (1976)
Calc
CC-Kow
E-KB
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
54
-------
28
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H3C
H,N
Compound Name: (l.l'-Biphenvl)-4.4'-diamine. 3.3'-dimethyl- (o-Tolidine)
CAS Registry Number; 119-90-7 Molecular Weight(g): 212.28
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M~1hr~1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr ) 4 x 1Q6
Reference
73.5
129-131
6.63
2.88
NHFG
NHFG
NHFG
3 x 10-12
4 x in6
C-Sw f Kow
Merck (1976)
Calc
CC-Kow
E-KB
M-DY PIT?
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
55
-------
29
EPA CONTRACT 68-03-2981 CICH£Hj!
WORK ASSIGNMENT NO. 14
Compound Name: Butanoic acid, 4-[bis(2-chloroethyl)amino3benzene-
CAS Registry Number; 305-03-3
.Molecular Weight(g):
304.23
Parameters;
Water Solubility (ppm)
Melting Point (.°C).
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant '
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation _ .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr'1)
Oxidation Rate Constant (M hr~ )
Reference
1.67 x 103
64-66
9.51
2.74 (partial)
1 x 10-10
unknown
C-Sw f Kow
Merck (1976)
Gale
CC-Kow
EA-NM
EA-NM
EA-NM
E-KB
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
(a) Aryldialkyl amines react with R02 by electron, not H-atom transfer.
56
-------
30
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Aicn
Compound Name: Camphene, octachloro-
CAS Reeistrv Number: 8001-35-2 M«la,,,,ia,. t^Ev
Parameters:
Water Solubility (com)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen 12.94
Log (Octano I/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M^hr"1) (a)
Acid Hydrolysis Rate /a\
Constant. (M hi )
Neutral Hydrolysis Rate
Constant (hr~ ) (a)-
Microbial Degradation _ . -12
TCal-a rnnflfar"" (™1 nell hr~ ) ., X
Oxidation Rate Constant (M hr~ ) INERT
M: 414
Reference
Calc
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
(a)Some isomers may hydrolyze, but rates will vary with structure.
57
-------
31
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
HiN-C-OC2H5
O
Compound Name: Carbamic acid, ethyl ester (Ethyl carbamate urethane)
CAS Registry Number; 51-79-6 Molecular Weight (g): 89.09
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Reference
Alkaline
Constant
Hydrolysi
(M-ihr""1)
is Rate
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr'1)
Oxidation Rate Constant (M-1hr~ )
6.48 x 105
48-50
182-184
0.44
0.36 (extrap.)
2.78
-0.15
1 x 10~7
INERT
C-Sw f Kow
Merck (1976.)
Merck (1976)
C-vp f bp
Weast (1973)
Calc
CC-Kow
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
58
-------
32
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
CH,
N-C-OC2H5
O
Compound Name: Carbamic acid, methylnitroso-, ethyl ester
CAS Registry Number; 615-53-2 Molecular Weight (g): 132.1
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr'1)
-i _i
Oxidation Rate Constant (M xhr )
Reference
4.43 x 107
62-64/12 torr
1.1
4.13
-1.69
3 x 10~9
INERT
C-Sw f Kow
Klein (1982)
Klein (1982)
Calc
CC-Kow
•
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
59
-------
33
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
0=N—N
,CH2 CH,
II
O
Compound Name: Carbamide. N-ethyl-N-nitroso-
CAS Registry Number; 759-73-9
-Molecular Weight (g):
117.1
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant '
Acid Hydrolysis Rate
Constant (M'-Hir"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
3.31 x 108
103-104
3.66
-3.27
3 x 10~9
INERT
C-Sw f Kow
Merck (1976)
Calc
CC-Kow
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
60
-------
34
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
xCH3
0=N—N
NCNH,
Compound Name: Carbamide. N-methvl-N-nitroso-
CAS Registry Number; 684-93-5
-Molecular Weight (g):
103.1
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (OctanoI/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M hr-1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
6.89 x 108
124
3.22
-3.81
3 x 10~9
INERT
C-Sw f Kow
Merck (1976)
Calc
CC-Kow
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
61
-------
35
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H2N—C—NH2
S
Compound Name: Carbamide, thio- (Thiourea)
CAS Registry Number; 62-56-6
-Molecular Weight (s):
_ 1 7
Parameters:
Water Solubility (ppm)
Melting Point C°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M^hr"1)
Reference
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr" )
Microbial Degradation .,
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M hr~ )
1.72 x 106
180^182
2.38
-2.05 (partial)
1 x 10~7
4 x 1010
C-Sw f Kow
Hawlev (197.7)
Calc
CC-Kow
E-KB
M-OX SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
62
-------
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H,C
X
-CI
upound Name: Carbamoyl chloride, dimethyl—
CAS Registry Number; 79-44-7
-Molecular Weight (g):
107.54
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M'-hir"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
1.44 x 107
55-57/11 torr
1.95
3.34
-1.32 (partial)
3 x 10~9
INERT
C-Sw f Kow
Fluka (1982)
Jaber and Gunderson (1983)
Calc
CC-Kow
E-KB
M-ox Rn9j <;n
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
63
-------
37
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Chloronaphazine
CAS Registry Number; 494-03-1
-Molecular Weight (g):
268.20
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Reference
Hydrolysi
(M-l-hr'1)
is Rate
Alkaline
Constant
Acid Hydrolysis Rate
Constant (M^hr"1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant
165
210
0.30
8.38
3.62 (partial)
3 x 10~9
unknown
C-Sw f Row
Merck (1976)
C-Vp f bp
Calc
CC-Kow
EA-NM
EA-NM
EA-NM
E-KB
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
(a) Aryldialkyl amines react with R02 by electron, not H-atom transfer.
64
-------
38
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
CH2CI
Compound Name: l-Chloro-2,3-epoxypropane (Epichlorohydrin)
CAS Registry Number; 106-89-8 Molecular Weight (g): 92.53
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient) .
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M hr )
Reference
3.19 x 105
117.9
15.7
2.89
0.15 (partial)
HNES
2.88,j
3.51 x 10~3
INERT
C-Sw f Kow
Merck (1976)
Weast (19.73)
Calc
CC-Kow
Mabey & Mill (1978).
Mabey & Mill (1978)
HF-NBD
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
65
-------
39
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Cyclophosphamide
CAS Registry Number: 50-18-0
-Molecular Weight (g):
261.10
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M*1^"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
1.31 x 109
41-45
8.16
-3.22 (partial)
1 x ID'10
INERT
C-Sw f Kow
Merck (1976)
Calc
CC-Kow
E-KB
M-OX. R02. SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
66
-------
40
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Daunomycin
CAS Registry Number; 20830-81-3 Molecular Welght(g):
527.5
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Reference
Acid
Constant
Hydrolysis Ra
ant (M'-hir'1)
Rate
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~" )
2.7 x 105
188-190 (dec)
16.48
-1.99
3 x 10~9
8 x 109
4 x 107
C-Sw f Kow
Merck (1976)
Calc
CC-Kow
•
E-KB
M-OX SO
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
67
-------
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
-N-C
jl
O
Cl
H i
-s-c-c=
=CHCI
H
Compound Name: Diallate
CAS Registry Number; 2303-16-4
-Molecular Weight (g):
273.5
Parameters;
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M^hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Reference
Oxidation Rate Constant
"
14
150/9 torr
6.4 x 10" 3
8.55
0.73 (partial)
3 x 10~9
PNFR
INERT
Spencer (1973)
Merck (1976)
C-Vp f bp
Gale
CC-Kow
E-KB
.M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not b'e used in more detailed assessments.
68
-------
EPA CONTRACT 68-03-2981 Hf(j NH2
WORK ASSIGNMENT NO. 14 2
42
Compound Name: rHam-lne (Hydrazine)
Parameters:
Boiling Point (°C)
Coefficient)
Constant
Constant (hr~ )
Rate Constant (ml
umber: 302-01-2 Molf>-Mlar weight
tv (own) 3.41 x 108
(°C) 113.5
(torr) 14
ht/Oxygen 1.00
ater Partition
-3.08
lysis Rate
r-1) NHFG
s Rate
-1, NHFG
i )
ysis Rate
) NHFG
adation 1 _y
r™i r(an"1hr--h l x 10
_ pnr)^rnrir fv,r— i\ . ,?li^
• Constant (M'^r'1) labile
fe): 32.05
Reference
C-Sw f Kow
Aldrlch C1982')
Yaws pf al . Ciq74>>
CC-Kow
E-KB
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
(a) Reacts with oxygen directly. Half-life estimated to be less than 10 days.
69
-------
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
NH,
Compound Name: 2,4-Diaminotoluene
CAS Registry Number; 95-80-7
-Molecular Weight (g):
122.17
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M^hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M hr~ )
Reference
4.77 x 104
9.7-98
292
3.8 x 10~5
3.82
0.35
NHFG
NHFG
NHFG
1 x ID'10
2 x 106
C-Sw f Kow
Aldrich (1982)
Weast (1981)
C-Vp f bp
Calc
CC-Kow
E-KB
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
70
-------
44
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: l,2;7,8-Dibenzopyrene
CAS Registry Number; 189-55-9
-Molecular Weight (g):
305
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M hr'1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr"" )
Reference
0.11
9.53
6.62
NHFG
NHFG
NHFG
-i «-12
3 x 10
2 x 108
C-Sw f Kow
Calc
CC-Kow
E-KB
M-OX SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
71
-------
45
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Cl Br
r r
H2C-CH— CH2
Compound Name: 1,2-Dibromo-3-chloropropane
CAS Registry Number: 96-12-8 MoipniTar WeightCg1): 236.3
Parameters: Reference
Water Solubility (ppm) 100°
Boiling Point (°C) 196
1.0
Vapor Pressure (torr) 0.8/21°C
Molecular Weight/Oxygen 7.38
Log (Octanol/Water Partition
Coefficient) 2.29
Alkaline Hydrolysis Rate
Constant (M^hr'1) 21
Acid Hydrolysis Rate vrnvs
<-> ~ ^~_*. /•»/"" -*-i —— 1^ nrdLO
CousLauL CM hr '•;
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation . n~^^
T?at» Constant (ml roT^^r'^ ,.. 3 X 10
PVirtfi-kl iri--f i- 77 -i t-rk Pnn^^-m^ ^lrr— 1^ FNc.R
Oxidation Rate Constant (M^hr'1) INERT
Spencer (1973)
Merck (1976)
C-Vp f bp
Merck (1976)
Calc
CC-Kow
Burlinson et al. (.1982).
E-KB
-
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
72
-------
46
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H
H 5 G- AS «C j H 3
Compound Name: Diethylarsine
CAS Registry Number: 692-42-2
-Molecular Weight (g):
134.05
Parameters;
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M'-'-hr'1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
417
105
35
4.19
2.97 (partial)
NHFG
NHFG
NHFG
1 x 10-10
PNER
unknown
C-Sw f Kow
Weast (1981)
C-VP f bp
Calc
CC-Kow
E-KB
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
73
-------
47
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
O
Compound Name: 1,4-Diethylene dioxide (p-Dioxane)
CAS Registry Number; 123-91-1
-Molecular Weight (g):
88.10
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~ )
Acid Hydrolysis Rate
Constant (M'TuT1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr )
Reference
4.31 x 105
101.1
39.9
2.75
0.01
NHFG
NHFG
NHFG
1 x 10-10
PNER
INERT
C-Sw f Kow
Merck (1976)
Weast (1973)
Calc
CC-Kow
f>
E-KB
M-OY Rf>9 <;n
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
74
-------
48
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H2N—N—CHj
CH,
Compound Name: 1,1-Dimethylhydrazine
CAS Registry Number: 57-14-7
-Molecular Weight (s):
60.10.
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant '
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
• Reference
1.24 x 108
63.9
157
1.88
-2.42
NHFG
NHFG
NHFG
1 x 10-10
PNFR
C-Sw f Kow
Merck (1976)
Verschueren (1977)
Calc
CC-Kow
•
E-KB
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
75
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49
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H H
H5C2— N — N —C2H,
Compound Name: N.N'-Diethylhydrazine
CAS Registry Number; 1615-80-1
-Molecular Weight (g):
88
Parameters:
Water Solubility '(ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .,
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr'1)
Oxidation Rate Constant (M hr~ )
Reference
2.88 x 107
2.75
-1.68
NHFG
NHFG
NHFG
1 x 10-10
PNER
C-Sw f Kow
Calc
CC-Kow
E-KB
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
76
-------
50
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Diethylstilbestrol
CAS Registry Number; 56-53-1
-Molecular Weight (g):
268.34
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M hr""1)
Neutral Hydrolysis -Rate
Constant (hr~ )
Microbial Degradation 1
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M-1hr~ )
Reference
9.60 x 10~3
169-172
8.39
5.46
NHFG
NHFG
NHFG
1 x 10-10
2 x 107
C-Sw f Kow
Merck (1976)
Calc
CC-Kow
E-KB
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
77
-------
51
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
(CHjsO
Compound Name: Dimethyl sulfate
CAS Registry Number; 77-78-1
-Molecular Weight (g>:
126:13
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M~1hr~1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant
Reference
3.24 x 105
188 (dec)
76/15 torr
0.68/20°C
3.94
-1.24 (partial)
53
HNES
0.6
3 x 10-12
INERT
C-Sw f Kow
Verschueren (19.77)
Merck (1976)
Weber et al. (1981)
Calc
CC-Kow
Mabey and Mill (1978)
Mabey and Mill (1978)
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
78
-------
52
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Dinitrotoluenes
CAS Registry Number; 25321-14-6
Weight (g):
182.14
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M^hr"1)
Reference
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
3100
5.69
2.29
NHFG
NHFG
NHFG
(0.2 - 7) x 10"10
(a)
INERT
C-Sw f Kow
Calc
CC-Kow
Spanggord et al. (1981)
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
(a)Nitrotoluene with o-nitro6oluene structure have photolysis rate constant
> 0.01 hr-1 CTse et al., 1983)
79
-------
53
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: 2,3-Dinitrotoluene
CAS Registry Number; 602-01-7
-Molecular Weight (g):
182.14
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M~1hr~1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant
Reference
3100
5.69
2.29
NHFG
NHFG
NHFG
5 x ID'10
0.07
INERT
C-Sw f Kow
Calc
CC-Kow
Spanggord et al. (1981)
T«P Pf al noST*
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
80
-------
54
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: 2.5-Dinitrotoluene
CAS Registry Number; 619-15-8
-Molecular Weight(g):
182.14
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M hr-1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
Reference
1.32 x 103
52.5
5.69
2.28
NHFG
NHFG
NHFG
7 x ID'10
0.3
INERT
C-Sw f Kow
Weast (1981)
Calc
CC-Kow
Spanggord et al. (1981)
Tse P.t al . (1381}
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
81
-------
55
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: 3,4-Dinitrotoluene
CAS Registry Number; 610-39-9
-Molecular Weight (g):
182.14
Parameters;
Water Solubility (ppm)
Melting Point
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M^hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M hr~ )
Reference
1.08 x 103
58.3
5.69
2.29
NHFG
NHFG
NHFG
4 x 10-10
INERT
C-Sw f Kow
Weast (1981)
Calc
CC-Kow
Spanggord et al. (1981)
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
82
-------
56
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: N.N-DIphenylamine
CAS Registry Number; 122-39-4
-Molecular Weight (g>:
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
Reference
57.6
53-54
302
3.8 x 10~^
5.29
3.60
NHFG
NHFG
NHFG
3 x 10~9
3 x 107
C-Sw f Row
Merck (1976)
Merck (1976)
C-vp f bp
Calc
CC-Kow
E-KB
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
83
-------
57
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
= N—N
Compound Name: Ethanamine, N-ethyl-N-nitroso-
CAS Registry Number; 55-18-5
-Molecular Weight (g): 102.14
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M^hr"1)
Reference
Acid Hydrolysis Rate
Constant (M hr-1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant
Oxidation Rate Constant (M hr~ )
2.2 x 105
175-177
1.10
3.19.
0.34
3 x ID'12
INERT
C-Sw f Kow
Merck (19-76)
Klein (1982)
Calc
CC-Kbw
E-KB
M-DY Pf>9
-------
58
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H,C-
-NH,
Compound Name: Ethanethioamide
CAS Registry Number; 62-55-5
-Molecular Weight (g):
75.14
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation -
Rate Constant (ml cell" hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
1.63 x 105
108.5
2.35
-0.91 (partial)
1 x 10-10
PNER
INERT
Merck (197*^
Verschueren (1977)
Calc
CC-Kow
E-KB
M-DY RO7, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
85
-------
59
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
0=N—N
Compound Name: Ethanol, 2>2t-(pitrosoimino)bis-
CAS Registry Number; 1116-54-7 Molecular Weight(g>:
134.1
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M^hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .,
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr~l)
Oxidation Rate Constant (M~~hr~ )
Reference
3.1 x 107
114/1.5 torr
8.3 x 10~4
4.19
-1.54
3 x ID'12
INERT
C-Sw f Row
Klpin ("1982)
Klp-in fl982")
Calc
CC-Kow
•
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
86
-------
60
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
I
CH2= CH —N-CHj
Compound Name: Ethenamine. N-methvl-N-nitroso-
CAS Registry Number; 4549-40-0
-Molecular Weight (g):
86.1
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation -
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr )
Reference
7.6 x 105
47-48/30 torr
12.3
2.69
-0.23
3 x ID'12
INERT
C-Sw f Row
Klein (1982)
Klein (1982)
Calc
CC-Kow
E-KB
M-OX R02. SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
87
-------
61
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Br-CHz— CH,- Br
Compound Name: Ethylene dibromide
CAS Registry Number; 106-93-4 Molecular Weight(g): 187.88
Parameters;
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M^hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr~l)
Oxidation Rate Constant (M hr~ )
Reference
1.18 x 104
131.4
11.7
5.87
1.76
HNES
HNES
3.7 x 10~5
1 x 10-10
PNER
INERT
C-Sw f Kow
Dreisbach (1959)
Dreisbach (1959)
Calc
CC-Kow
E-A-Dibromopropane
E-KB
M-OY T?O? sn
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
88
-------
62
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
A
Compound Name: Ethylene oxide
CAS Registry Number; 75-21-8 Molecular Weight(g): 44.05
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M^hr'1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation _
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
Reference
complete
10.7
1305
1.38
-0.22
HNES
33.5
2.43 x 10~3
PNER
TNFT?T
Conway et al. (1983)
Merck (1976)
Conway et al. (1983)
Calc
CC-Kow
Mabey & Mill (1978)
Mabey & Mill (1978)
VF-NBD
M-OY T3D9 SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
89
-------
63
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H,C—S
Compound Name: Ethyl methanesulfonate
CAS Registry Number; 62-50~°
-Molecular Weight (g):
124.16
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M^hr""1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
3.69 x 105
85-86/10 torr
0 . 206
3.88
0.21
PNER
INERT
C-Sw f Kow
Aldrich (1982)
Jaber and Gunderaon (19S3\
Calc
CC-Kow
HF-NBD
M-OX pn? <;n
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
90
-------
64
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name!
CAS Registry Number; QnfU-fifi-4
-Molecular Weight (g): 5000-7500
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M^hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
Reference
3 x 10
-9
INERT
E-KB
M-OX R02. SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
91
-------
65
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: n-ftlueopy-ranose. 2-deoxv-2-O-methvl-a-nitrosoureido)-
CAS Registry Number; 18883-66-4 Molecular Weight (g) : 265.22
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant ""
Acid Hydrolysis Rate
Constant (M^hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M-1hr~ )
Reference
2.7 x 1011
115 (dec).
8.29
-6,20
1 x 10-10
INERT
C-Sw f Kow
Merck C1976)
Calc
CC-Kow
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
92
-------
66
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
-CH
O O
Compound Name: Glycidylaldehyde
CAS Registry Number; 765-34-4
-Molecular Weight (g):
72.1
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M^hr"1)
Reference
Acid Hydrolysis Rate
Constant (M^hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
1.70 x 108
112-113
19.7
2.25
-1.55
HNES
8.86
1.02 x 10~3
INERT
C-Sw f Kow
SRI Chemical Handbook
C-VP f bp
Calc
CC-Kow
E-A-Glycirdol
E-^A-Glycirdol
HF-NBD
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
93
-------
67
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
NONHH
HjC-N-C-N-NOz
Compound Name:
-r^ f-rnsn— N— methl— N* -nitre—
CAS Registry Number; 70-25-7
Molecular WeightCg):
147.09
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M'-hir"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M hr~ )
Reference
2.35 x 108
118 (dec)
4.60
-3.18 (partial)
3 x 10-12
INERT
C-Sw f Kow
Merck (1976)
Calc
CC-Kow
-
E-KB
M-OX R02. SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
94
-------
68
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Kepone
CAS Registry Number: 143-50-0
-Molecular Weight (g):
490.6
Parameters:
Water Solubility (ppm)
Melting Point (°C>
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant "
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr"~ )
Reference
9.9 x 10~3
350 (dec)
15.3
2.00 (partial)
NHFG
NHFG
NHFG
3 x 10-12
PNKH
INERT
C-Sw f Kow
Merck (1976.).
Calc
CC-Kow
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
(a).This compound exists as the gem-dio.1 in aqueous solution.
95
-------
69
II Cll, CM,
EPA CONTRACT 68-03-2981 \..c' cu -c-oii
WORK ASSIGNMENT NO. 14 a','. Wo a.,-o-co-r-u.-cn,
/SA »o ocii,
V-y
Compound Name: Lasiocarpine
CAS Reeistry Number: 303-34-4 Molecular Weiektfe'): 411.5
Parameters: Reference
Water Solubility Cppm) . 1600
Melting Point (°C) 96.4-97
Boiline Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen 13.8
Log (Octanol/Water Partition
Coefficient) 0.99
Alkaline Hydrolysis Rate
Constant (M^hr"1)
Acid Hydrolysis Rate
Cons taut (M hr ^-) •
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml eeT-1 br~ ) ~ ..
Oxidation Rate Constant (M'^hr"1) 2 x 10
C-Sw f Kow
SRI Chemical Handbook
Calc
CC-Kow
NBD
M-OY SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
96
-------
70
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H
/ \ CH3
Compound Name: Z-Methvlaziridine (Propyleneimine)
CAS Registry Number: 75-55-8
-Molecular Weight (g):
57.10
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant ""
Reference
Acid Hydrolysis Rate
Constant (M hr-1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr )
9.44 x 105
66-67
141
1.78
-0.48
HNES
1.87 x 10~7
2.5 x 10~3
_
PNER
INERT.
C-Sw f Row
Hawley (1977)
C-vp f bp
Calc
CC-Kow
E-A-Aziridine as cited by
Mabey and Mill (1978)
E-A-Aziridine as cited by
Ear ley. et al. (1958)
HF-NBD
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
97
-------
71
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H H H H
:—s—c—c—ci
H H H H
Compound Name: Mustard Gas
CAS Registry Number; 505-60-2
-Molecular Weight (g):
159.08
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M'-hir'1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
Reference
800
13-14
215-217
0.17
4.94
1.37 (partial)
PNER
2 x 1010
Franke (1967)
Merck (1976)
Merck (1976)
Franke (1967)
Calc
CC-Kow
HF-NBD
M-OX SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
98
-------
72
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
H,N H
2,7-Naphthalenedisulfonic acid, 3,3'-[ O.S'-dimethyl-U.l'-biphenyl)
Compound Name: A. A'-divD-bis (azo) Ibis (5-amino-4-hvdroxy)-tetrasodium salt
CAS Registry Number; 72-57-1
-Molecular Weight (g).:
960.83
Parameters;
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant '
Acid Hydrolysis Rate
Constant (M^hr'1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
Reference
3.8 x 108
30.0
-1.76 (oartial)
NHFG
NHFG
NHFG
1 x 10-10
1 x 107
C-Sw f Kow
Calc
CC-Kow
E-KB
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
99
-------
73
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: 1-Naphthylamine
CAS Registry Number: 134-32-7
-Molecular Weight (g):
143.18
Parameters;
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
2.35 x 103
50.
301
6.5 x 10~5
4.47
2.07
NHFG
NHFG
NHFG
3 x 10~9
6 x 106
C-Sw f Row
Verschueren (1977).
Merck C1976")
C-VP f br>
Calc
CC-Kow
E-KB
OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments,
100
-------
74
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: 2-Naphthylamine
CAS Registry Number: 91-59-8
-Molecular Weight (g):
143.18
Parameters: .
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation -
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant
Reference
586
110.2
306
2.56 x 10~4
4.47
2.07
NHFG
NHFG
NHFG
3 x 10~9
4 x 106
C-Sw f Kow
Verschueren (1977)
Merck (1976)
Karyakin et al. (1968)
Calc
CC-Kow
•
E-KB
OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
101
-------
75
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
CO
CO — Ni — CO
Compound Name: Nickel carbonyl
Parameters:
Boiling Point (°C)
Coefficient)
Constant (M~1hr~1)
Constant (hr )
CO
umber: 13463-39-3 MoiPrMiar tJ
> Constant (M^hr'1) INERT
(<>}.. 170.73
Reference
Merck (1976)
Baev and Fedulova (1973)
Calc
NBD
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
102
-------
76
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: N—
CAS Registry Number: 1QQ-75-4
-Molecular Weight (g):
114
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M"1^"1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr~l)
Oxidation Rate Constant
Reference
1.9 x 106
215/721 torr
1.4 x 10'1
3.56
-0.49
NHFG
NHFG
NHFG
3 * 10-12
INERT
C-Sw f Row
Klein (1982)
Klein (1982)
Calc
CC-Kow
IN *'
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
103
-------
77
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
6
Compound Name: N-Nitrosopvrrolidine^
CAS Registry Number: 930-55-2
-Molecular Weight (g):
100.12
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M'-Hir"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation _
Rate Constant (ml cell hr"~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M hr~ )
Reference
7.0 x 106
214
1.1 x Kf1
3.13
-1.06
NHFG
NHFG
NHFG
3 x ID'12
INERT
C-Sw f Row
Aldrich (1982)
Klein (1982)
Calc
CC-Kow
E-KB
M-OX R02
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
104
-------
78
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: 1.2-Oxathiolane. 2.2-dioxide
H2C-
-1
°2
CAS Registry Number; 1120-71-4
-Molecular Weight (g):
122.1
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation 1
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr-1)
Oxidation Rate Constant (M hr"" )
Reference
1.7 x 106
3.82
-0.40
1 x 10-10
PNER
INERT
C-Sw f Kow
Calc
CC-Kow
E-KB
M-DY T?n9 <;n
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
105
-------
79
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Phenobarbital
CAS Registry Number: 50-06-6
-Molecular Weight (g):
232.23
Parameters:
Water Solubility (ppm)
Melting Point C°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M~1hr~1)
Neutral Hydrolysis Rate
Constant (hr )
Microbial Degradation
Rate Constant (ml cell hr )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
moo
174-178
7.26
-0.19
1 x ID'10
INERT
Merck fl976")
Merck (1976)
Calc
CC-Kow
E-KB
M-OX R02. SD
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
106
-------
80
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Br Br ° Br pr
ztH CHjC 0-P-OCH2CH CH2
O
HC-Br
HjC-Br
Compound Name: i-propanol. 2.3-dibromo. phosphate (3:1)
.tris (2,3-dibromopropyl) phosphate
CAS Registry Number; 12,6-72-7 Molecular Weight(g):
698
Parameters:
Water Solubility (ppm)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (OctanoI/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant '
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
120
21.81
4.12 (oartial")
HNES
HNES
1.15 x 10~3
3 x 10-12
PNER
TNPTJT
C-Sw f Row
Calc
CC-Kow
E-A-Naled
E-KB
M-OX R02. SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
107
-------
81
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
CH,
^
CH,
OH
Compound Name: Propanenitrile, 2-hydroxy-2-methyl- (Acetone cyanohydrin)
CAS Registry Number; 75-86-5 Molecular Weight(g): 85.11
Parameters:
Water Solubility (ppm)
Boiling Poinp (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant
Acid Hydrolysis Rate
Constant (M~ hr~^)
Neutral Hydrolysis Rate
Constant Chr"1)
Microbial Degradation ..
Rate Constant (ml cell hr~ )
Reference
tolysis Rate Constant
Oxidation Rate Constant
1.52 x 106
95
44.9
2.66
-0.51
HNES
HNES
3 x 10~9
PMTpp
INERT
C-Sw f Kow
Weber, et al. (1981)
C-VP f'bp
Calc
CC-Kow
E-KB
M-OX R02. SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
108
-------
82
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: TDE (l,l-Dichloro-2.2-bis (4-chlorophenvl)ethane)
CAS Registry Number; 72-54-8 Molecular Weight(g): 320.1
Parameters;
Water Solubility (ppm)
Melting Point
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M hr-1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation 1
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M hr~ )
Reference
2.2 x 10~2
10.9- 110.
10.0
6.21
NHFG
NHFG
NHFG
1 x ID'10
PWPTJ
INERT
C-Sw f Kow
Merck (19J6)
Calc
CC-Kow
•
E-KB
M-OX R02, SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
109
-------
83
EPA CONTRACT 68-03-2981
WORK ASSIGNMENT NO. 14
Compound Name: Uracil, 5-[bisC2-chloroethyl)aminoj-(Uracil mustard)
CAS Registry Number; 66-75-1 _ Molecular Weight (g).: 252.1
Parameters:
Water Solubility (ppm)
Melting Point (°C)
Boiling Point (°C)
Vapor Pressure (torr)
Molecular Weight/Oxygen
Log (Octanol/Water Partition
Coefficient)
Alkaline Hydrolysis Rate
Constant (M~1hr~1)
Acid Hydrolysis Rate
Constant (M hr"1)
Neutral Hydrolysis Rate
Constant (hr~ )
Microbial Degradation .
Rate Constant (ml cell hr~ )
Photolysis Rate Constant (hr"1)
Oxidation Rate Constant (M-1hr~ )
Reference
641
206 (dec)
7.88
-1.09 (partial)
3 x lO'12
INERT
C-Sw f Kow
Merck (1976)
Calc
CC-Kow
E-A-NM
E-A-NM
• E-A-NM
E-KB
M-OX R02. SO
These data were estimated for use in a preliminary assessment to be
conducted by the EPA, and should not be used in more detailed assessments.
110
-------
REFERENCES
Aldrich Chemical Company. 1982-1983. Aldrich Catalog/Handbook of Fine
Ch'dmicals. Milwaukee, Wisconsin.
Baev, A. K. and L. G. Fedulova. 1973. Zh. Fiz. Khim. 47, No. 10, 2523-
2526.
Burlinson, N. E., .L. Ai.= Lee, and D. H. Rosenblatt. 1982. Environ. Sci.
Technol. _16, No. 9, 627-632.
Conway, R. A., G. T. Waggy, M. H. Speigel, and R. L. Berglund. 1983.
Environ. Sci. Technol. 17, No. 2, 107-112.
Dreisbach, R. R. 1959. Physical Properties of Chemical Compounds-II.
Advances in Chemistry Series No. 22. American Chemical Society,
Washington, DC.
Earley, J. E., C. E. O'Rourke, L. B. Clapp, J. 0. Edwards, and B. C.
Lawes. 1958. J. Amer. Chem. Soc. JKH No. 13, 3458-3462.
Fluka Chemical Corporation. 1982/1983 Catalog. Hauppauge, NY.
Franke,S. 1967. Manual of Military Chemistry, Volume 1. Chemistry of
Chemical Warfare Agents. (Translation of: Lehrbuch der Militarver-
lag, Band 1, Chemie der Kampfstcffe.) Deutscher Militarverlag,
East Berlin.
Grain, C. 1982. Vapor Pressure. In: Handbook of Chemical Property
Estimation Methods. W. J. Lyman, W. F. Reehl, D. H. Rosenblatt,
Eds. McGraw-Hill Book Company, New York.
Green, H. S., and F. Jones. 1967. Trans. Faraday Society* 63, No. 7,
1612-1619.
Hawley, G. G. 1977. The Condensed Chemical Dictionary, Ninth Edition.
Van Nostrand Reinhold Co., New York.
Jaber, H. M., and E. C. Gunderson. 1983. Data Acquisition for Environ-
mental Transport and Fate Screening for Compounds of Interest to
the Office of Emergency and Remedial Response. Part II. Vapor
Pressure Measurements. Final Report for U. S. EPA, Washington, DC.
Work Assignment No. 14 in partial fulfillment of EPA Contract No.
68-03-2981.
Jentzsch, R., and G. W. Fischer. 1978. Journal f. Prakt. Chemie. 320,
No. 4, 634-646.
Karyakin, N. V., I. B.. Rabinovich, and L. G. Pakhomov. 1968. Zh. Fiz.
Khim. .42, No. 7, 1814-1816.
Ill
-------
Klein, R. G. 1982. Toxicology. _23, No. 2-3, 135-147.
.Mabey, W. , and T. Mill. 1978. J. Phys. Chem. Ref. Data. ]_, No. 2,
383-415.
The Merck Index. 1976. Ninth Edition. Merck and Co., Rahway, New Jersey.
Osborn, A. G. , and D. W. Scott. 1980. J. Chem. Thermodynamics. 12,
No. 5, 429-438.
Ross, W. C. J. 1949. J. Chem. Soc. 183. 183-191.
Spanggord, R. J. , W. R. Mabey, T. Mill, T.-W. Chou, J. H. Smith, and S.
Lee. 1981. Environmental Fate Studies of Certain Munition Waste-
water Constituents. Final Report, Phase III, Part II - Ancillary
Studies. Prepared for U. S. Army Medical Research and Development
Command, Fort Detrick, Frederick, MD in partial fulfillment of
Contract No. DAMD 17-78-C-8081.
Spencer, E. Y. 1973. Guide to the Chemicals Used in Crop Protection.
Agriculture Canada. Publication 1093, Sixth Edition. Ottawa,
Ontario, Canada.
SRI Chemical Handbook. SRI International Chemical-Environmental Depart-
ment: Files. Menlo Park, CA.
Tse, D., J. Winterle, and W. Mabey. 1983. Unpublished work for U. S.
EPA, Work Assignment No. 5, Contract No. 68-03-2981.
Verschueren, K. 1977. Handbook of Environmental Data on Organic Chemicals.
Van Nostrand Reinhold Co., New York.
Vogel, T. 1983. Unpublished work. Stanford University, Stanford, CA.
Weast, R. C. Ed. 1973. Handbook of Chemistry and Physics. 54th Edition.
CRC Press, Cleveland, OH.
Weast, R. C. Ed. 1981. Handbook of Chemistry and Physics. 62nd Edition.
CRC Press, Cleveland, OH.
Weber, R. C., P. A. Parker, and M. Bowser. 1981. Vapor Pressure Distrib-
ution of Selected Organic Chemicals. EPA Report No. 600/2-81-021.
Wiedemann, H. G. 1972. Thermochim. Acta. _3, No. 5, 355-366.
Yalkowsky, S. H., and S. C. Valvani. 1980. J. Pharm. Sci. 69, No. 8,
912-922.
Yaws, C. L., J. R. Hopper, and M. G. Rojas. 1974. Chemical Engineering.
j.8, No. 25, 91-100.
112
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SECTION 4
CALCULATION OF PARTITION COEFFICIENTS OF
ORGANIC CHEMICALS IN AQUATIC ENVIRONMENTS
This section was taken in whole from W. R. Mabey, J. H. Smith,
R. T. Podoll, et al., "Aquatic Fate Process Data for Organic Priority
Pollutants," EPA Report No. 440/4-81-014, December 1982.
113
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Section 4
CALCULATION OF PARTITION COEFFICIENT OF
ORGANIC CHEMICALS IN AQUATIC ENVIRONMENTS
4.1 BACKGROUND
The partitioning of a chemical between water and sediment and between
water and biota will affect the concentration of the chemical in water and
the rate of loss of the chemical from aquatic systems. Solubility data,
on the other hand, are required for calculation of Henry's constants,
which are needed to calculate volatilization rates of chemicals in aquatic
systems.
This section discusses the relationships between water solubility,
the partition coefficients for a chemical between sediment and biota, and
the partition coefficient for a chemical between octanol and water.
Moreover, the theoretical basis for such relationships is explained, and
some of the published correlations for these data are discussed. This
section also briefly discusses the calculation of the octanol-water
partition coefficient data used to calculate many of the other, partitioning
constants.
As discussed in Section 2, the partitioning of a chemical is given
by the equation
K - C /C (4.1)
p p w
where C and C are the concentrations on a particulate material (sediment
p w
or biota) and in water, respectively, and K is the partitioning constant
P
(or coefficient) whose units are determined by those of C and C (see
p w
section 2). In practice, C is usually defined as the amount of chemical
per dry weight of sediment (or organisms) to correct for the variability
of the particulate water content. The partition coefficient between
*
This section was taken in whole from W. R. Mabey, J. H. Smith, R. Ti Podoll,
et al., "Aquatic Fate Process Data for Organic Priority Pollutants," EPA
Report No. 440/4-81-014, December 1932.
114
-------
microorganism and water, K.,, given for individual organic chemicals in
Section 3, is in units of micrograms of chemical per gram of microorganism
divided by grams of chemical per liter of water. Because the amount of
organic chemical sorbed to sediments has been found to depend on the
amount of organic carbon in the sediment, it is useful to normalize a
measured sediment partition coefficient (K ) for organic carbon content:
KOC - yfoc <4-2>
where f is the fraction of organic carbon and K is the normalized
(for organic carbon content) partition coefficient. Karickhoff et al.
(1979) have also shown that, because f varies with sediment particle
size, the distribution of sediment particle size will markedly affect
measured K values.
oc
The octanol-water partion coefficient K has commonly been used
as a measure of the hydrophobicity of a chemical in medical and toxico-
logical applications as well as in environmental chemistry (Hansch and
Leo, 1979; Kenaga and Goring, 1978). A large number of K values is
therefore available as a result of the number of uses of such data. Most
significantly, K values can be calculated from molecular structure (see
Section 4.4). The K data in Section 3 are given to allow calculations
ow
of other properties (partitioning coefficients for biota as well as toxi-
cological data) for use in environmental assessments of the organic
priority pollutants.
4.2 CALCULATION METHODS
Several correlation equations have been proposed to calculate the
water solubility (.S ), K , and 1C from K values and to calculate K
values from water solubility. The more widely used of these equations
are discussed and analyzed in Section 4.3. Although we recognize that
better equations are evolving as more experimental data are obtained,
the following equations are recommended for use in environmental fate
assessments.
115
-------
4.2.1 Correlation Equations
In the following equations, all partition coefficients (K , K and
1C-) are unitless, and water solubility (S ) is in units of parts per million
a * w
(ppm). As discussed in Section 4.2.2, however, the solubility units of
molarity (moles per liter) or mole fraction are preferred.
K and K are correlated by the following equation (Karickhoff, 1979):
log KQC = 1.00 log KQW- 0.21 (4.3)
Correlation of S and K was reported by Yalkowsky and Valvani (1980).
For organic pollutants that are liquid in their pure state at 25°C:
log S = -1.08 log K + 3.70 + log MW (4.4)
where MW is the molecular weight of the pollutant (g mole ) . For organic
pollutants that are solid in their pure state at 25°C:
/AS
log Sw = -1.08 log KQW + 3.70 + log MW-lTp^; (mp-25) (4.5)
where mp is the melting point of the pollutant (°C) and ASf is the entropy
-1 -1
of fusion of the pollutant (cal mol deg ). If ASf is not known, it
may be approximated by (Yalkowsky and Valvani, 1980):
ASf - 13.6 + 2.5 (n - 5) (4-6)
where n is the number flexible atoms (i.e., atoms not involved in double
bonds, triple bonds, or part of a ring structure) in the pollutant molecule,
other than hydrogen. If n is less than 5, (n - 5) is set equal to zero.
The original equations in the literature are different if they were
reported in different solubility units. Refer to Section 4.2.2 for
the appropriate solubility units conversion factors.
116
-------
Correlation of K and S is provided by (Kenaga and Goring, 1978):
log KQC = -0.55 log Sw + 3.64 (4.7)
K-, can be correlated with K by
D OW
K_ = 0.16 K (4.8)
O OW
4..2..2 Units and Conversion Factors
Three commonly used units of aqueous solubility are defined below:
(.1) Mole fraction, x, the unitless ratio of the number of moles of
solute to the total number of moles of solute., plus water. In
symbols, for a binary solution of n moles of solute in n moles
of water
x = n/ (n + n )
~ n/n for n » n (4.9)
w w
(.2) Molarity, S, expressed in moles of solute per liter of solution
CM):
S(M) = n(mol)/liter of solution (4.10)
(3) Weight fraction, expressed in milligrams of solute per liter of
water, or parts per million, ppm
s roDm) = n (mol) MW (a mol"1) 1000 (mg s"1) „ ,
w VFF ' liter of water '
where MW is the molecular weight of the solute.
For solutions with S < 1 M, one liter of aqueous solution contains
approximately 55.5 moles of water. Thus
f or s
117
-------
or
x - 55.5 x for x < 10~2
(4.13)
To convert from molarity to ppm is straightforward by substituting
Equation (4.10) into equation (4.11)
ppm -* S(MW) (1000) for S < 1 M
(4.14)
Thus to convert from mole fractions to ppm follows from equations
(4.11) and (4.13)
ppm = ,?5'5..XN (MW) (1000)
(1 - x )
~55.5(x) (MW) (1000) for x < 10
These conversion factors are summarized in Table 4.1.
-2
(.4.15)
Table 4.1
CONVERSION FACTORS FOR COMPOSITION UNITS
FROM
ppm
(mole fraction)
M
(Molarity)
x
TO
ppm
M
(mole fraction) (Molarity)
5.55 x 104 (MW)
CMW) (103)
1.80 x 10~5
MW
1
55.5
io-3
MW
55.5
118
-------
Concentration in aqueous solution is preferably given in mole fraction
or molarity units since these units are measures of the amount of solute
per amount of solution. The weight fraction or ppm, on the other hand,
expresses the weight of solute per weight of solution and is thus a
function of the molecular weight of the molecule, which is not relevant
to environmental or toxicological effects.
4.3 CALCULATION OF K and S FROM K
OC W OW -
The sediment partition coefficient, normalized for organic carbon
content (K ), and aqueous solubility (S ) of an organic pollutant are
critical to its environmental fate. Because K and S values may be
unmeasured or unreliable, it is important to.be able to correlate these
environmental parameters with other experimental quantitites, namely, to
predict unmeasured values and appraise the reliability of measured values.
It is useful to correlate these parameters with octanol/water
partition coefficients (K ) for practical as well as theoretical reasons.
ow
Practically, K values are easier to measure and, where K measurements
ow ow
have not been made, calculated values may be used with confidence. The
theoretical basis for expecting correlations of K and S with K is
oc w ow
described below. The correlation of IL, with other partitioning constants
is not discussed in this section since a recent review of the subject is
available.
4.3.1 Partitioning Thermodynamics
This discussion first considers the partitioning of a chemical
between octanol and water, with octanol being a representative organic
phase. If a small amount of a chemical is added to a closed vessel
containing n-octanol and water, the vessel is shaken, and the octanol
and water are allowed to separate, the chemical will partition between
the two phases (see Figure 4.1). 3y convention, the small amount of
chemical in each phase is called the solute. The partitioning of the
solute molecules between the two phases can be understood in terms of a
simple lattice model. If we assume that every molecule (water, octanol,
119
-------
to
O
0
0
0
o
0
o
w w w w w w w
w w w w s w w
w w w w w w w
w w w w w w w
SA-6729-8
FIGURE 4.1 LATTICE MODEL OF A SOLUTE (S)
PARTITIONING BETWEEN OCTANOL
(0) AND WATER (W) PHASES
K " C/C - 2
s
0
o
w
w
w
w
0 0
0 0
s o
WWW
w s w
WWW
WWW
S 0
0 0
o s
WWW
WWW
WWW
w s . w
SA-6729-9
FIGURE 4.2 LATTICE MODEL OF A HIGHER MOLE
FRACTION OF SOLUTE (S) PARTITIONING
BETWEEN OCTANOL (0) AND WATER
(W) PHASES
Because the environment of each solute mole-
cule is the same, K = C 1C = 2 as in
ow o w
Figure 4.1.
-------
and solute) in both phases occupies a particular site on a three-dimensional
lattice, with uniform spacing between sites, then the fraction of sites
in each phase occupied by the chemical is the mole fraction x. A two-
dimensional cross section of this lattice is shown in Figures 4.1 and
4.2.
The tendency for a solute molecule to leave either phase is propor-
tional to the solute mole fraction in that phase and to the forces acting
on the solute in that phase. The forces acting on a solute molecule will
depend on which molecules occupy neighboring sites on the lattice.
Figures 4.1 and 4.2 show that, over the mole fraction range of x = 1/28
to x = 1/14, solute molecules in the water phase are surrounded by water
molecules. Thus, the forces acting on the solute in the water phase are
independent of the solute mole fraction. Consequently, the tendency (f)
of a solute molecule to leave the water phase is directly proportional
to its mole fraction:
f = Hx (4.16)
where H is a constant representing the forces exerted on the solute by
the solvent. At higher solute mole fractions, where solute-solute inter-
actions become important (that is, where the solute is concentrated
enough that solute molecules occupy neighboring lattice sites), H becomes
a function [H(x)] of the solute mole fraction, and thus f is no longer
directly proportional to x:
f = H(x) x (4.17)
The partitioning of the chemical between the octanol and water phases
depends on this relative tendency of the chemical to leave each phase (f),
which is conveniently viewed as a force per unit area. In thermodynamics,
*
f is called the fugacity and, as explained above, is proportional to the
relative amount of the solute in the phase, x, and the forces acting on
the solute within each phase; explicitly,
*
See, for example, G. L. Lewis and M. Randall, Thermodynamics, revised
by K. S. Pitzer and L. Brewer (McGraw-Hill, NY, 1961).
121
-------
fw • (fV xw
fo -
where subscripts w and o refer, respectively, to the water and octanol
T>
phases, and f and y..are, respectively, the reference fugacity and
activity coefficient, which together represent the forces acting on the
solute in the i phase. At equilibrium
fw = fo (4.20)
so that
_R
f Y Y
/ w w // 01 \
x /x = —-— = — (4.21)
o w -R Y
Y
T>
In general, at constant pressure, f depends only on the temperature and
y. depends on the composition as well as the temperature of the i phase.
In sufficiently dilute solutions, however, the forces acting on a solute
molecule will be independent of x. because, as explained above, the
environment of a solute molecule will remain constant. Thus (f y.) will
be a function only of temperature
(fRYi) = E± (4.22)
where H. is the Henry's constant for a very dilute solution of the solute
in phase i. Thus
x /x = H /H (4.23)
o w w o
is a function only of temperature. However, if x or x is large enough
that y or Y is not constant, then K will also no longer be constant.
o ' w ow °
122
-------
Because composition is commonly measured in moles liter (M), it
is convenient to define:
K = C /C = r (x /x ) = r (H /H ) (4.25)
ow o w wo o w wo w o
where r is a constant equal to the ratio of the molar volume of water
wo n
r = v /v (= 0.115) (4.26)
wo wo
to that of octanol. (In terms of the lattice mode, r is equal to the
wo
ratio of the number of sites per unit volume of octanol to that of water.)
Numerous workers have"correlated the partitioning of chemicals be-
tween sediment and water and between biota and water with octanol/water
partition coefficients. Before discussing these specific correlations
in detail, it is useful to understand the conditions that must be met
for these correlations to be successful.
Partitioning of a solute between water and any other water immiscible
phase p (.!•&• t biota, sediment) may be described by
K = r (H /H ) (4.27)
pw wp w p
From equation (4.25) for partitioning between octanol and water
H = K H /r (.4.28)
w ow o wo
thus
K » (r /r )(H /H )K = r (H /H )K (4.29)
pw wp wo o p ow op o p ow
where r is the ratio of the molar volume of octanol to that of phase
op
p. Thus, taking the logarithm of both sides of equation (4.29)
123
-------
log Kpw = log KQW + log CropHo/Hp) (4.30)
Thus, for the second term on the right-hand side of equation (4.30) to
remain constant for a set of chemicals partitioning between water-octanol
and water-phase p, phase p must be chemically similar to octanol and both
K and K must be measured at low enough solute concentrations that
ow pw °
solute-solute interactions are absent.
The success of K -K correlations (to be discussed in detail below),
ow oc '
for example, may thus be understood. First, by normalizing adsorption
for organic carbon content, we ensure the chemical similarity of phase p
(.that is, the organic content) and octanol. Second, the partitioning of
the chemical between the water and sediment phases is usually measured
at very low surface coverage (in the linear region of the adsorption
isotherm) where adsorbate-adsorbate interactions are minimal.
Octanol/water partition coefficients have been used not only to
correlate other partitioning data, but also to predict aqueous solubili-
ties. The assumptions implicit in these predictions become apparent
on close examination of the octanol/water partition experiment.
If it is assumed that the ratio of the number of solute molecules
in each phase remains constant up to the limit of solubility, then
Kow = (Co/Cw) dilute = CCo/Cwisaturated (.4.31)
From equation (4.21), this means that the ratio of activity coefficients
Y /Y remains constant up to saturation. As explained above, however,
the ratio Y /Y will depend on solute concentration, particularly if
C (saturated) is large enough that solute-solute interactions become
w
*Because of the chemical similarity of a neutral organic solute with
n-octanol, it is expected that Y will not vary significantly with C
124
-------
important. Furthermore, if we assume that the solubility of the chemical
in pure.water equals its solubility in the octanol-saturated water phase
of the partition measurement, then
Kow = VSw
where S and S are solubilities in moles liter (M) in pure octanol and
o w
pure water, respectively.
To correlate aqueous solubility with K , many authors have proposed
ow
an equation of the form:
log S = -(I/a) log K + c (4.33)
w ' ow
where a and c are constants. Equation (4.33) may be derived by modifying
equation (4.32) to account for deviations of real systems from model be-
havior:
K - (S /S )S (4.34)
ow o w
This equation is clearly identical to equation (4.32) for a = 1. Taking
the logarithm of both sides of equation (4.34) and rearranging terms:
log S - - (I/a) log KQW + (I/a) log SQ (4.35)
If S is assumed constant for a set of solutes in octanol, equation
o
(4.35)becomes
log Sw - - (I/a) log KQW + c (4.36)
and the correlation coefficients a and c may be calculated from a plot
of known values of log S versus known values of log K for the given
125
-------
set of solutes. Clearly, if the assumptions implicit in equation (.4.32)
are reasonable, the calculated value of ji should be close to one.
The variability of S for a set of solutes is difficult to quantify
except by comparing liquid and solid solutes. If two solutes are identi-
cal except that one is a liquid and the other is a solid in its pure state
at temperature T, the solid will be less soluble than the liquid because
of the additional energy required to remove solute molecules from the
solid phase. Thus, if we assume that all liquid solutes have the same
solubilities in n-octanol, and we use this pure liquid solute as the ref-
erence state, calculated solid solubilities must be corrected for the
energy necessary to transform the solid to the liquid state. This energy
is called the enthalpy of fusion, and from simple thermodynamic argu-
ments, we can modify equation (.4.35) for solid solutes:
fiHf Tf- T
log S = - a/a) log K + c - (I/a) - (.4.37)
where AH,, is the enthalpy of fusion, R is the gas constant, and Tf is
the melting temperature of the solute. At the melting point,
AHf = Tf AS (.4.38)
Therefore at 25°C, equation (.4.38) becomes
AS
log Sw = - (I/a) log Kow + c - Gnp-25) (.4.39)
where mp is the melting point (in °C) and AS. is the entropy of fusion
-1 -1
(in cal deg mole ) . This correction is zero for solutes that are
liquid at 25 C, but substantial for solutes with high melting points.
Assuming that the theory is approximately correct and the correlation
coefficient a_ is approximately equal to one, Table 4.2 and Figure 4.3
illustrate the magnitude of this correction as a function of melting
point for a hypothetical solute with an uncorrected solubility of 100 ppm
and a typical entropy of fusion of 13.6 entropy units (cal deg mol )•
126
-------
Table 4.2
EFFECT OF MELTING POINT CORRECTION
ON WATER SOLUBILITY VALUES
Solubility po.nt Solubility*
(uncorrected) ° (.corrected)
(ppm) (. C) (ppm)
100 25 . 100
100 50 56
100 100 18
100 200 2
100 300 0.2
* o
log S (.corrected) = log S Cuncorrected) - 0.01 (mp-25) at 25 C,
Vv vv
where &S. = 13.6 and a = 1 are assumed in equation (4.39) and S
i w
is the water solubility in ppm.
127
-------
1.2
1.0
0.8
f 0.6
0.4
0.2
f = Sw (corrected )/Sw( unconnected)
f = 10-(0.01)(mp-25)
-50
50 100 150 200 250
MELTING TEMPERATURE (°C)
300 350
SA-6729-10
FIGURE 4.3 ENTHALPY OF FUSION CORRECTION FACTOR FOR AQUEOUS SOLUBILITY
AT 25°C AS A FUNCTION OF MELTING TEMPERATURE
128
-------
4.3.2 Comparison of Reported Correlations
Table 4.3 lists a representative sample of recently published
correlations among K , K , S . This section examines these correla-
ow oc w
tions in detail.
K -K . As discussed earlier, the sorption constant K is the
oc ow r oc
amount of chemical adsorbed per unit weight of organic carbon in the
sediment divided by the equilibrium concentration of the chemical in
the water phase. This constant is useful because, once K has been
oc
determined for a chemical, the sorption partition coefficient may be
calculated if the fraction organic content (f ) is known:
oc
K = K (f N = C /C C4.40)
p oc ocj s w
where
K = Sorption partition coefficient
P
K = Sorption partition coefficient normalized for organic carbon
content
f = Fraction of organic content in the sediment CO < OC <1)
oc
C = Concentration of the adsorbed chemical
s
C = Equilibrium solution concentration.
Furthermore, it is useful to be able to predict K values from
* oc
the more easily measured K values. The theoretical basis for expect-
J ow
ing good K -K correlations has been discussed above. Two recent
° ° oc ow
K -K correlations that have appeared in the literature are listed in
oc ow
Table 4.3. The significantly different correlation equations of Kenaga
and Goring (1978) and Karickhoff et al. (1979) probably reflect the
different data bases used to correlate K with K .
oc ow
129
-------
Table 4. J
REPORTED CORRELATIONS Of K . K AND S
ow oc w
Corn-Lie ion
K - K
oc ow
Equation
lug K = 0.544 log K +1.377
oc ow
Data Base
Pollutants
I Aromatic hydrocarbons (8)
Carboxyllc acids and esters (5)
Phosphorus containing insectlciu«-s (5)
Ureas and uraclls (7)
Symmetrical trlazines (6)
Miscellaneous (14)
Adsorbents
Variety of soils
Authors
Kenaga and Goring (1978)
K - K
oc ow
log K = 1.00 log K - 0.21
oc ° ow
(4.3) Pollutants
Polycycllc aromatics (8)
Chlorinated hydrocarbons (2)
Karlckhoff et al. (1979)
S - K
LO
O
log S = - 0.922 log K + 4.184
w ow
S in ppm
(4.42) Substituted benzenes and halobenzenes (12)
Halogenated blphenyls and dlphenyl oxides (11)
Aromatic hydrocarbons (9)
Phosphorus containing insecticides (16)
Carboxyllc acids and esters (9)
Ureas and uraclls (7)
Miscellaneous (24)
Kenaga and Goring (1978)
S - K
w ow
log x • - 1.08 log K - 1.04
S ° OW
1360
(mp - 25)
x is the mole fraction solubility at 25 C
S
AS is the entropy of fusion in cal deg mol
mp Is the melting point In °C (If mp i 25
then the term in brackets Is zero)
(4.43) Simple aliphatics and arnmatics
in the following groups (n = 114)
Alcohols
Halogens
Amines
Carboxylic acids and esters
Aldehydes and ketones
Ethers
Nltro compounds
Yalkowsky (1980)
Number in parentheses refer to the number of pollutants In the data base.
-------
x in the mole fraction solubility
Table 4.3 (continued)
REPORTED CORRELATIONS OF K . K AND S
ow oc w
: lac Ion
K - S
oc u
Equation
log K " - 0.55 log Sw -f 3.64
Data Base
Authors
(4.7) Similar to data base for equation (4.41) Kenaga and Goring (1978)
K - S
oc w
in ppm
leg K - - 0.56 log S + 0.70
Offl W
log K - - 0.56 log S +0.93
(4.44) Pollutants
(4.45)
Polychlorlnated biphenyls (3)
Pesticides (4)
llalogenated ethanes and propanes (6)
Te t rachloroethene
1.2-Dlchlorobenzene
Adsorbents
Willamette silt loam
Miscellaneous other soils
Chlou et al. (1979)
K - S
oc u
log K - - 0.54 log x -1-0.44
oc -s
(4.46) Similar to data base for equation (4.3)
Karlckhoff (1979)
K is the sorption partition coefficient normalized for organic matter reported by
Chlou et al. (1979). Assuming K - 1.7 K . equation (4.45) is derived.
a on
-------
The theoretical equation of Table 4.4,
log K =1.00 log K + constant (.4.47)
follows from assuming that the second term on the right-hand side of
equation (.4.30) is constant; the data base required for a good fit with
equation (.4.47) follows from the assumptions used in the derivation of
equation (4.30). It is clear from Table 4.4 that the data base and
correlation equation of Karickhoff et al. (1979) closely conform with
the theoretical model; however, the data base and correlation equation
of Kenaga and Goring (1978) do not.
The advantages and disadvantages of using these alternative equa-
tions are not as well defined, however. Although the equation of
Karickhoff et al. (.1979) conforms to a simple model and accurately pre-
dicts sorption coefficients from K data for a limited class of organic
ow e
chemicals, it has not been widely tested and may be highly inaccurate
for a more universal set of pollutants and soil/sediments. The equation
of Kenaga and Goring (.1978) , however, is strictly empirical and only
roughly predicts K values from K data, but it is applicable to a
more universal set of pollutant/adsorbent systems because of the data
base used. When more precise K and K data are available, it will
oc ow
be of interest to assess the predictive value of both of these correla-
tions for both the universal set and individual classes of pollutant/
adsorbent systems. It may become apparent that several correlation
equations may be required to adequately predict K values from K
values for the variety of systems of interest.
S - K Several comparisons of the equations of Kenaga and Goring
(1978) and Yalkowsky (1980) can be made. For reasons discussed earlier,
the mole fraction units of solubility used by Yalkowsky are to be pre-
ferred to the ppm units used by Kenaga and Goring. In fact, to compare
equation (4.42) of Kenaga and Goring with equation (4.43) of Yalkowsky,
we must assume an average molecular weight for the chemicals in the data
132
-------
Table 4.4
DATA BASES FOR K -K CORRELATIONS
oc ow
log K
oc
K
ow
oc
Chemicals
Kenaga and Goring (1978)
0.54 log K + 1.38
b ow
Measured and calculated
values compiled from
literature
Calculated average values
for each chemical from
adsorption coefficients
for widely differing soils
Very wide range of
organic classes
Karickhoff et al. (1979)
1.00 log K - 0.21
6 ow
Measured by Karickhoff
et al.
Measured values for the
silt (high organic content)
fractions of two natural
sediments
Nonpolar or slightly
polar organics
Theoretical
1.00 log K + constant
& ow
Measured for very
dilute solution
Uniform organic content
of soil/sediment. Mea-
sured for adsorption
from very dilute solutions
Nonpolar organics
-------
base of Kenaga and Goring. Converting equation (4.42) from ppm to mole
fractions units
log x - - 0.922 log KQW - 0.56 - log MW (4.48)
where x is the mole fraction solubility and MW is the.average molecular
weight.
The variation of equation (4.48) with MW is shown in Figure 4.4
and compared with Yalkowsky's equation for liquid solutes. Two observa-
tions can be made about Figure 4.4. First, the molecular weight depen-
dence of equation (4.48) is not very great for chemicals in the molecular
weight range of 100-400. Second, because the average molecular weight
of chemicals in the data base used to determine equation (4.48) is in
the range of 100-400, it is clear that solubilities predicted by equation
(4.48) will be approximately an order of magnitude lower than those
predicted by equation (4.43).
A comparison of measured solubilities (in molarity units, M) with
those predicted by the equations of Kenaga and Goring and of Yalkowsky
is shown in Table 4.5 for a series of chlorinated methanes and ethanes.
Note that all the chemicals listed in Table 4.5 (except hexachloroethane,
which sublimes) are liquid at 25 C. Furthermore, is is clear from
Table 4.5 that equation (4.43) of Yalkowsky predicts the aqueous solu-
bility of chlorinated methanes and ethanes very accurately, whereas the
corresponding prediction of equation (4.42) is an order of magnitude
lower. Table 4.6, which compares calculated and measured solubilities
for some low melting point aromatics, further supports these conclusions.
The cause of this discrepancy becomes clear when we examine the con-
trasting methods and data bases used by Kenaga and Goring and by Yalkowsky
to develop their correlations. Kenaga and Goring empirically correlated
K with the solubility of a set of chemicals, most of which are solid
ow J
at 25°C. In other words, Kenaga and Goring implicitly used a solid
solute reference state; consequently, their correlation equation cannot
accurately predict the solubility of a chemical that is liquid at 25 C.
134
-------
-2
-3
X
ra -5
-7
Kenaga and Goring
(log xs = -0.922 log Kow -0.56 - log MW)
Yalkowsky
(log xs = -1.08 log Kow -1.04)
xs = Mole Fraction Solubility
MW = Molecular Weight
I J_ I I
MW = 1
MW = 10
MW = 100
MW = 200
MW = 400
I
1
log K
ow
SA-6729-11
FIGURE 4.4 COMPARISON OF SOLUBILITY -
EQUATIONS FOR LIQUID SOLUTES
135
-------
Table 4.5
CALCULATED VERSUS MEASURED SOLUBILITIES FOR CHLORINATED METHANES AND ETHANES
u>
Chloromethane
Dichloromethane
Chloroethane
1,1-Dichloroethane
Trichloromethane
1,1.2-Trichloroethane
1,1,1-Trichloroethane
1,1,2,2-Tetrachloroethane
Tetrachloromethane
Hexachloroethane
mp
log S
(M)
w
-LOR ^
& OW
0.95
1.26
1.49
1.80
K96
2.07
2.50
2.66
2.96
4.62
<°c)
-98
-95
-136
-97
-64
-37
-30
-36
-23
Sublimes
Kenaga and Goring
-1.4
-1.87
-2.03
-2.45
-2.67
-2.84
-3.25
-3.48
-3.70
-5.45
Yalkowsky
-0.32
-0.66
-0.91
-1.24
-1.41
-1.53
-2.00
-2.17
-2.49
-4.29
Measured
-0.89
-0.80
-1.05
-1.25
-1.16
-1.47
-2.27
-1.76
-2.29
-3.68
-------
Yalkowsky, on the other hand, explicitly used a liquid solute reference
state. To calculate the solubilities of chemicals that are solid at
25 C, Yalkowsky included an entropy of melting correction term. Thus
the equation of Yalkowsky, assuming accurate known values of the entropy
of fusion C^S-) and melting point (T_), is equally valid for liquid
and solid solutes.
As discussed earlier, if two solutes are identical except that one
is a liquid and the other is a solid in its pure state at 25 C, then the
solid will be less soluble than the liquid by a factor of
exp [-2.303(.ASf/1360)(jnp-25)] (4.49)
where &Sf is the entropy of fusion and mp is the melting point ( C).
If AS is constant, then it is clear from equation (4.46) that solu-
bility decreases as the melting point increases. Assuming AS, = 13.6
entropy units and converting mole fraction solubilities to molarity
units, Figure 4.5 illustrates that equation (4.43) of Yalkowsky, in
contrast with equation (.4.42) of Kenaga and Goring, successfully predicts
the decrease in solubility with increase in melting point for a-, B-,
&-, and Y-
Figure 4.5 also indicates that implicit in equation (4.42) of
Kenaga and Goring is an empirical average of the solid solute correction
term. Because the solubilities of liquid solutes predicted by equation
(.4.42) are approximately an order of magnitude lower than measured values,
we can assume that this average correction term is approximately equal
to 0.10, which is the dashed line in Figure 4.3. Thus, the predicted
solubilities of equation (.4.42) should approximate those of Yalkowsky
and measured values for solutes with melting points in the 100 to 200 C
temperature range. Figure 4.6 illustrates, in fact, that for solutes
with an approximate molecular weight of 150, an entropy of fusion of
13.6 and a melting point of 125°C, the correlation equations of Yalkowsky
and of Kenaga and Goring are similar. Moreover, Table 4.7 illustrates
137
-------
Table A.6
CALCULATED VERSUS MEASURED SOLUBILITIES FOR LOW MELTING POINT AROMATICS
u>
oo
Nitrobenzene
Benzene
Toluene
Chlorobenzene
Ethylbenzene
1,2-Dlchlorobenzene
mp
log S
w
-LOg K.
" OW
1.87
2.13
2.79
2.84
3.34
3.56
( C)
5.6
5.5
-95
-45
-94.9
-17
Kenaga and Goring
-2.63
-2.63
-3.35
-3.48
-3.92
-4.26
Yalkowsky
-1.32
-1.60
-2.31
-2.37
-2.90
-3.14
Measured
-1.82
-1.64
-2.24
-2.37
-2.85
-3.00
-------
-2.0
-3.0
_ -4.0
CO
O)
2 -5.0
-6.0
-7.0
Yalkowsky
| Kenaga and Goring
• Measured
7 - BHC
a - BHC
I
I
50 100 150 200 250
MELTING TEMPERATURE (°C)
300
350
SA-6729-12
FIGURE 4.5 SOLUBILITIES OF HEXACHLOROCYCLOHEXANES (a-, 0-. 5-, -y-BHC)
AS A FUNCTION OF MELTING TEMPERATURE
139
-------
-3
-5
en
O
-7
Kenaga and Goring
— log xs = -0.922 log Kow -0.56 - log MW
= 150
Yalkowsky
log xs - -1.08 log K^ -1.04 -[(mp - 25)ASf/1360]
ASf = 13.6 mp = 125°C
I I I I I
1
3 4
log Kow
SA-6729-13
FIGURE 4.6 COMPARISON OF SOLUBILITY - K EQUATIONS FOR SOLID SOLUTES
ow
140
-------
Table 4.7
CALCULATED VERSUS MEASURED SOLUBILITIES FOR SELECTED PESTICIDES
Lindane
Aldrin
Chlordane
ODD
DDT
log K
& ow
3.89
5.30
5.48
6.20
6.91
MP
(°C)
113
104
108
112
109
log
Kenaga and Goring
-4.85
-6.24
-6.46
-7.04
-7.74
Sw(M)
Yalkowsky
-4.38
-5.80
-6.04
-6.85
-7.59
Measured
-4.40 to -5.15
-6.30 to -7.35
-5.30 to -6.85
-6.5 to -7.2
-6.6 to -8.5
-------
that for selected pesticides with melting points around 110 C the cor-
relations of Yalkowsky and of Kenaga and Goring compare equally well
with measured values.
Figure 4.5 also suggests that solubilities predicted from equation
(.4.42) of Kenaga and Goring will become progressively higher relative
to measured values as the melting temperature increases above 200 C.
Table 4.8 indicates that, indeed, measured solubilities of chemicals
with melting points above 200 C systematically fall below those pre-
dicted by Kenaga and Goring.
In summary, equation (.4.42) of Kenaga and Goring should be re-
stricted to chemicals with melting points in the 100 to 200 C range,
but equation (.4.43) of Yalkowsky, because it includes a melting point
correction factor is not limited by melting point restrictions.
K - S . To compare equation (4.7) with equations (4.45) and
(4.46), it is again necessary to assume an average molecular weight
for the correlation equation of Kenaga and Goring. If an average
molecular weight of 200 is assumed, converting equations (4.7) and
(.4.45) to mole fraction solubility units gives
log K = - 0.55 log x - 0.23 (Kenaga and Goring, 1978) (4.50)
log K = - 0.56 log x - 0.04 (.Chiou et al. , 1979) (4.51)
oc s
log K = - 0.54 log x + 0.44 (Karickhoff et al., 1979) (4.46)
oc s
Several observations can be made about these equations. First,
the similarity of equations (4.50) and (4.51) is remarkable, consider-
ing the contrasting data bases used by Kenaga and Goring and by Chiou
et al. to determine their correlation coefficients. In fact, equations
C4.50), (4.51), and (.4.46) may all be written in the form
K = (constant) x'0'55(±°'01)
oc
142
-------
Table 4.8
AQUEOUS SOLUBILITIES OF HIGH MELTING POINT CHEMICALS
Chemical Name
Benzo[k]fluoranthene
Anthracene
Benzo[g,h,i]perylene
Chrysene
Dibenz[a,h]anthracene
TCDD
B-BHC
Melting Point
217
219
222
258
270
303
309
Solubilities
(ppm)
Measured
5.6 x 10
0.045
2.6 x 10
1.8 x 10
5 x 10~4
2 x 10~4
0.24
-4
-4
-3
Predicted by
Equation (4.42)'
0.04
1.2
0.015
0.1
9 x 10
-3
7.5 x 10
4.0
-3
Kenaga and Goring (1978)
143
-------
It is not clear why the solubility coefficient of -0.55(±0.01) should
appear in each of these correlations. If as expected from the above
discussions [see equations (4.3), (4.42), and (4.43)],
log K = a log K + constant (4.53)
oc ow
and
log K = - a log x +• constant "(4.54)
ow s
where a -*• 1, then by substituting equation (.4.54) into equation (.4.53)
2
log K = - a log x + constant /^ 55)
~ - 1.0 log x + constant
It is also apparent that none of these three equations accounts for
the variation in solubility and hence variation in K value with the
oc
melting point of the adsorbed chemical. The difference in adsorption
behavior between solid and liquid solutes, in general, has been well
documented in the literature (see, for example, Kipling, 1965). In fact,
Roe (.1975) has accounted for this difference in terms of the solid solute
correction factor discussed earlier in this report. Karickhoff et al.
(.1979), in discussing their relatively poor correlation of K with x
(.compared with their excellent correlation of K with K ) , mention
that a correction term is probably needed in equation (4.40) to account
for the enthalpy of fusion of the chemicals they studied.
K,, - K . The partitioning of organic chemicals has recently been
a OW
reviewed by Baughman and Paris (1981), who noted the paucity of reliable
data available for correlating K_ with other partitioning parameters.
For the chemicals in Section 3, the following equation was used to cal-
culate K_
a
KB = °-16 Kow C4'81
144
-------
which is the simplified version of the equation given by Baughman and
Paris (1981),
log ^ = 0.907 log KQW - 0.21 (4.56)
The reader is referred to the above review for an excellent exposition
on the problems of reliably measuring K^ and the use of correlation
equations to calculate K_ from S or from K or K data.
B w oc ow
4.4 CALCULATION OF K FROM STRUCTURAL PARAMETERS
ow
The thermodynamics of partitioning of a chemical solution between
octanol and water phases was discussed in 4.3.1, and the use of the
octanol/water partition coefficient, K , for calculating S , K and
^ ow & w' oc
K_ was described in Section 4.3.2. Although K is the symbol used by
B OW
many scientists for this partition coefficient, earlier literature and
some current medical toxicology literature has commonly referred to the
logarithm value of K as "log P" (Hansch and Leo, 1979). For discussion
ow
in this section only, the log P nomenclature will be used instead of
log K , although the K term will be used.
ow ° ow
The K data on the data sheets in Section 3 were calculated using
ow
a computer program developed at SRI; it uses the FRAGMENT method for
calculating log P values (Hansch and Leo, 1979). The theory and pro-
cedures for these calculations are discussed in detail in that reference.
Briefly, the method assumes that select groups of atoms in a molecule
can be considered fragments, each of which contributes to the total log
P value in an additive manner
n
log P = I a f (4.57)
i n n
where a is the number of occurrences of fragment f of structural type n.
Values of f have been empirically derived from the vast body of log P
data available in the literature. Since the calculation of log P values
145
-------
for complex molecules can be time—consuming and subject to numerous cal-
culation errors, the FRAGMENT calculation method and the data base for
fragment values have been incorporated into a computer program using the
*
PROPHET computer network. The log P data are generated by first enter-
ing the structure on a graphic tablet. The log P program then uses an
ordered substructure search routine to obtain fragment values for frag-
ments of the molecular structure. Fragments are used, rather than atoms,
because atomic contributions to log P vary with certain structural en-
vironments. The program then adds the fragment values to obtain log P
values. It also identifies where the log P calculation may be incomplete
because of the absence of values for particular fragments or because
polar interactions must be accommodated by manual calculations. The log
P program is under continuing development and evaluation at SRI and
other laboratories .
The manual calculation of log P values using the FRAGMENT method
is already established as a valid method for obtaining these data (Hansch
and Leo, 1979). The calculations are, of course, subject to errors
arising from subtle structural differences that are not recognized or
cannot be accounted for when obtaining empirical values for the molecular
fragments. In fact, the primary source of error is the original data
on which the fragment values are based. The lack of reliable data is
also a dilemma for verification of calculated log P values.
As an indicator of the accuracy of the log P calculation program
Table 4.9 compares the K values recently published by Hassett et al.
ow
(1980) with the K values calculated by the log P program. Although
ow
the chemicals are not among the organic priority pollutants, they do
represent some of the best K data currently available. The calculated
ow
and measured K values agree within the factor of two for 8 of the 14
ow °
*PROPHET is a NIH resource available to biological and
scientists on a time-share basis. Information on the log P/PROPHET
system can be obtained from Dr. Howard L. Johnson at SRI.
146
-------
Table 4.9
CORRELATION OP MEASURED AND CALCULATED VALUES OF K
ow
Computer-Calculated
Measured K ± S.D.3 K b
_ Compound _ _ ow _ _ ow r
Pyrene 124,000 ± 11,000 79,400 1.6
7,12-Dimethylbenz[a]anthracene 953,000 ± 59,000 871,000 1.1
Dibenz[a,h]anthracene 3,170,000 ± 883,000 5,890,000 0.54
3-Methylcholanthrene 2,632,000 ± 701,000 9,330,000 0.28
Dibenzothiophene 24,000 ± 2,200 33,900 0.71
Acrldine 4,200 ± 940 2,570 1.6
13H-Dibenzo[a,i]carbazole 2,514,000 ± 761,000 692,000 3.6
Acetophenone 38.6 ± 1.2 38.9 0.99
1-Napthol 700 ±62 417 1.7 .
Benzidine 46.0 ± 2.2 35.5 1.3
2-Aminoanthracene 13,400 ± 930 1,660 8.1
6-Aminochrysene 96,600 ± 4,200 24,000 4.0
Anthracene-9-carboxylic acid 1,300 ± 130 15,500 0.08
3 Hassett et al. (1980).
b Ratio of measured K to calculated K .
ow ow
-------
compounds listed and agree within a factor of five for 12 of toe 14
compounds. It is also significant to note that the last three compounds
in Table 4.9 show the most disagreement between calculated and measured
K values, and these compounds are large molecules containing groups
that may participate in H-bonding interactions.
In general, the accuracy of log P calculations by this method
closely approaches the accuracy of experimental determinations performed
over the last ten or twenty years because the fragment values were
derived largely from those experimental data (.by regression analysis)
and incorporate the same experimental errors. It is not uncommon for
measured log P values for a given compound in the literature to vary
by 1 to 2 units; this corresponds to a factor of 10 to 100 in measured
K variation.
ow
148
-------
4.5 REFERENCES
Baughman, G. L., and D. F. Paris. 1981. Microbial Bloconcentration
of Organic Pollutants from Aquatic Systems - A Critical Review.
Critical Reviews in Microbiology, January 1981.
Chiou, C. T., L. J. Peters, and V. H. Freed. 1979. A'Physical Concept
Of Soil-Water Equilibria for Nonionic Organic Compounds. Science, 206,
831.
Hansch, C. , and A. Leo. 1979. Substituent Constants for Correlation
Analysis in Chemistry and Biology (Wiley-Interscience, New York)
Karickhoff, S. W., D. S. Brown, and J. A. Scott. 1979. Sorption of
Hydrophobic Pollutants on Natural Sediments. Water Research 13, 241.
Kenaga, E. E., and C. A. I. Goring. 1978. Relationship Between Water
Solubility. Soil-Sorption, Octanol-Water Partitioning and Bioconcen-
tration of Chemicals in Biota. ASTM, Third Aquatic Toxicology Symposium,
October 17-18, New Orleans, LA
Kipling, J. J. 1965. "Adsorption From Solutions of Non-Electrolytes",
(Academic Press, London).
Lewis, G. L., and M. Randall. 1961. "Thermodynamics", revised by K. S.
Pitzer and L. Brewer, (McGraw-Hill, New York).
Roe, R. J. 1975. Adsorption of Solid Solutes from Solution: Application
of the Multilayer Theory of Adsorption. J. Colloid Interface Sci.,
10, 64.
Yalkowsky, S. H. and S. C. Valvani. 1980. Solubility and Partitioning I:
Solubility of Nonelectrolytes in Water. J. Pharm. Sci.,j59_, 912.
149
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Data Acquisition for Environmental Transport and Fate
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