United States Office of Water EPA 440/5-80-050
Environmental Protection Regulations and Standards October i960
Agency Criteria and Standards Division ,
Washington DC 20460 £ . j
&EPA Ambient
Water Quality
Criteria for
Haloethers
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AMBIENT WATER QUALITY CRITERIA FOR
HALOETHERS
Prepared By
U.S. ENVIRONMENTAL PROTECTION AGENCY
Office of Water Regulations and Standards
Criteria and Standards Division
Washington, D.C.
Office of Research and Development
Environmental Criteria and Assessment Office
Cincinnati, Ohio
Carcinogen Assessment Group
Washington, D.C.
Environmental Research Laboratories
Corvalis, Oregon
Duluth, Minnesota
Gulf Breeze, Florida
Narragansett, Rhode Island
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DISCLAIMER
This report has been reviewed by the Environmental Criteria and
Assessment Office, U.S. Environmental Protection Agency, and approved
for publication. Mention of trade names or commercial products does not
constitute endorsement or recommendation for use.
AVAILABILITY NOTICE
This document is available to the public through the National
Technical Information Service, (NTIS), Springfield, Virginia 22161.
ii
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FOREWORD
Section 304 (a)(l) of the Clean Water Act of 1977 (P.I. 95-217),
requires the Administrator of the Environmental Protection Agency to
publish criteria for water quality accurately reflecting the latest
scientific knowledge on the kind and extent of all identifiable effects
on health and welfare which may be expected from the presence of
pollutants in any body of water, including ground water. Proposed water
quality criteria for the 65 toxic pollutants listed under section 307
(a)(l) of the Clean Water Act were developed and a notice of their
availability was published for public comment on March 15 1979 (44 FR
15926), July 25, 1979 (44 FR 43660), and October 1, 1979 (44 FR 56628)
This document is a revision of those proposed criteria based upon a
consideration of comments received from other Federal Agencies, State
agencies, special interest groups, and individual scientists'. The
criteria contained in this document replace any previously published EPA
criteria for the 65 pollutants. This criterion document is also
published in satisifaction of paragraph 11 of the Settlement Agreement
in Natural Resources Defense Council, et. al. vs. Train 8 ERC 2120
(D.D.C. 1976). modified, 12 EEC 1833 (D.D.C. 1979).
The term "water quality criteria" is used in two sections of the
Clean Water Act, section 304 (a)(l) and section 303 (c)(2). The term has
a different program impact in each section. In section 304, the term
represents a non-regulatory, scientific assessment of ecological ef-
fects. The criteria presented in this publication are such scientific
assessments. Such water quality criteria associated with specific
stream uses when adopted as State water quality standards under section
JOJ become enforceable maximum acceptable levels of a pollutant in
ambient waters. The water quality criteria adopted in the State water
quality standards could have the same numerical limits as the criteria
developed under section 304. However, in many situations States may want
to adjust water quality criteria developed under section 304 to reflect
local environmental conditions and human exposure patterns before
incorporation into water quality standards. It is not until their
adoption as part of the State water quality standards that the criteria
become regulatory.
Guidelines to assist the States in the modification of criteria
presented in this document, in the development of water quality
standards, and in other water-related programs of this Agency, are beinq
developed by EPA. => ./> a
STEVEN SCHATZOW
Deputy Assistant Administrator
Office of Water Regulations and Standards
111
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ACKNOWLEDGEMENTS
Aauatic Life Toxicology:
William A. Brungs, ERL-Narragansett
U.S. Environmental Protection Agency
•John H. Gentile, ERL-Narragansett
U.S. Environmental Protection Aoencv
Mammalian Toxicology and Human Health Effects:
Patrick Durkin (author)
Syracuse Research Corporation
Betty Herndon
Midwest Research Institute
John F. Risher (doc. mgr.) ECAO-Cin Larry Fradkin, ECAO-Cin
U.S. Environmental Protection Agency U.S. Environmental Protection Agency
Jerry F. Stara (doc. ngr.) ECAO-Cin Rolf Hartung
U.S. Environmental Protection Agency University of Michigan
Steven D. Lutkenhoff, ECAO-Cin
Woodhall Stopford
U.S. Environmenta1 Protection Agency Duke University Medical Center
Anne Trontell
Energy Resources Co., Inc.
Jonathan Ward
University of Texas Medical Branch
lechnical Support Services Staff: D.J. Reisman. M.A. Ga^louqh, B.L. Zwayer,
P.A. Daunt, K.S. Edwards, T.A. Scandura. A.T. Pressley, C.A.~Cooper,
M.M. Denessen,
Clerical Staff: C.A. Haynes, S.J. Faehr, L.A. Wade, D. Jones. 6.J. Bordicks,
B.J. Quesnell, C. Russom, B. Gardiner.
IV
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TABLE OF CONTENTS
Criteria Summary
Introduction /\_1
Aquatic Life Toxicology B-l
Introduction B-l
Effects B-l
Acute Toxicity B-l
Chronic Toxicity B-l
Summary B-l
Criteria B-2
References B-5
Mammalian Toxicology and Human Health Effects C-l
Introduction c-1
Exposure c-2
Ingestion from Water c-2
Ingestion from Food c-5
Pharmacokinetics c 7
Effects c_7
Acute, Subacute, and Chronic Toxicity C-7
Synergism and/or Antagonism, Teratogenicity
Mutagenicity and Carcinogenicity C-7
Criteria Formulation c-10
Existing Guidelines and Standards C-10
Current Levels of Exposure C-10
Special Groups at Risk C-10
Basis and Derivation of Criteria C-10
References C-12
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CRITERIA DOCUMENT
HALOETHERS
CRITERIA
Aquatic Life
The available data for haloethers indicate that acute and chronic toxic-
ity to freshwater aquatic life occur at concentrations as low as 360 and 122
wg/1, respectively, and would occur at lower concentrations among species
that are more sensitive than those tested.
No saltwater organisms have been tested with any haloether and no state-
ment can be made concerning acute or chronic toxicity.
Human Health
Using the present guidelines, a satisfactory criterion cannot be derived
at this time because of the insufficiency in the available data for halo-
ethers.
VI
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INTRODUCTION
Haloethers are compounds which contain an ether moiety (R-O-R) and halo-
gen atoms attached to the aryl or alkyl groups. This document covers chlo-
rinated aromatic ethers, namely, chlorophenyl phenyl ethers, bromophenyl
phenyl ethers, and polychlorinated diphenyl ethers.
It is not possible to determine the most probable aquatic fate for
4-chlorophenyl phenyl ether from available data. This pollutant is reported
to be rapidly degraded by acclimated sewage sludge, but biodegradation data
from river-water die-away experiments indicate that this compound has a
potential for persistence in natural surface waters. Sorption by organic-
rich sediments and bioaccumulation in fish have been demonstrated. Although
photolysis may make a minor contribution to the degradation of this pollut-
ant near the air-water surface, oxidation and hydrolysis are probably not
important as fate processes. The role of volatilization is uncertain.
A review of the production range (including importation) statistics for
4-chlorophenyl phenyl ether (CAS No. 7005-72-3), which is listed in the ini-
tial U.S. Environmental Protection Agency TSCA Inventory (U.S. EPA, 1979),
has shown that between 100,000 and 800,000 pounds of this chemical were pro-
duced or imported in 1977.*
* This production range information does not include any production/importa-
tion data claimed as confidential by the person(s) reporting for the TSCA
Inventory, nor does it include any information which would compromise con-
fidential business information. The data submitted for the TSCA Inven-
tory, including production range information, are subject to the limita-
tions contained in the Inventory Reporting Regulations (40 CFR 710).
A-l
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The general physical properties of 4-chlorophenyl phenyl ether are as
follows.
Molecular weight 204.66
(calc. from Weast, 1977)
Melting point -8°C**
(Dow Chemical Company, 1979)
Boiling point at 760 torr 284°C***
(MaiThe and Murat, 1912)
Vapor pressure at 25°C 0.0027 torr
(Calc. by Branson, 1977)
Solubility in water at 25°C 3.3 mg/1
(Branson, 1977)
Log octanol/water partition coefficient 4.08
(Branson, 1977)
Among the polychlorinated diphenyl ethers, 4,4'-dichlorophenyl phenyl
ether, C^HgC^O, has the following physical properties: molecular
weight 239.11, melting point 30°C, boiling point, 312-4°C, density 1.1231,
and it is insoluble in water (Weast, 1978-1979).
Very little information pertaining to the environmental transport and
fate of 4-bromophenyl phenyl ether was found, and it is, therefore, not pos-
sible to determine the most probable aquatic fate at this time. Some infer-
ences can be drawn from experiments performed with this pollutant's chloro
analog. 4-Chlorophenyl phenyl ether is reported to be rapidly degraded by
acclimated sewage sludge, but biodegradation data from river water die-away
** Brewster and Stevenson (1940) report a melting point of 46 to 47°C
for 2-chlorophenyl phenyl ether. They were apparently unable to
prepare a crystalline sample of 4-chlorophenyl phenyl ether.
*** Dow Chemical Company (1979) has determined the boiling point at 760
torr to be 293.03°C.
A-2
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experiments indicate that this compound has a potential for persistence in
natural surface waters. Sorption by organic-rich sediments and bioaccumula-
tion in fish may be important. Although photolysis may make a minor contri-
bution to degradation near the air-water surface, oxidation and hydrolysis
are probably not important as fate processes. The role of volatilization in
the removal of halogenated aromatic ethers from aquatic systems has not been
demonstrated and remains uncertain.
The general physical properties of 4-bromophenyl phenyl ether include:
Molecular weight 249.11
(Weast, 1977)
Melting point 18.72°C
(Weast, 1977)
Boiling point at 760 torr 310.14°C
(Weast, 1977)
Vapor pressure at 20°C 0.0015 torr
(calc. from Oreisbach, 1952)
Density 1.4208
Solubility in water Insoluble
Log octanol/water partition coefficient 4.28
(calc. by method of Leo, et al. 1971
using the data of Branson, 1977)
A separate water quality criteria document, entitled "Chloroalkyl
Ethers," covers the following compounds:
Bis(chloromethyl) ether
Bis(2-chloroethyl)ether
2-Chloroethyl vinyl ether
Bis(2-chloroisopropyl)ether
Bis(2-chloroethoxy)methane
A-3
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REFERENCES
Branson, D.R. 1977. A New Capacitor Fluid - A Case Study in Product Stew-
ardship. In: F.L. Mayer and J.I. Hamelink (eds.), Aquatic Toxicology and
Hazard Evaluation. ASTM Spec. Tech. Publ. 634. p. 44.
Brewster, R.Q. and G. Stevenson. 1940. The chlorination of phenyl ether
and orientation in 4-chlorophenyl ether. Jour. Am. Chem. Soc. 62: 3144.
Dow Chemical Company. 1979. Personal communication from M. Thomas (Dow) to
N.W. Gabel. Versar, Inc.
Dreisbach, R.R. 1952. Pressure-Volume-Temperature Relationships of Organic
Compounds. 3rd ed. Handbook Publishers, Inc., Cleveland, Ohio.
Leo, A., et al. 1971. Partition coefficients and their uses. Chem. Rev.
71: 525.
Mailhe, A. and M. Murat. 1912. Derives halogenes de 1'oxyde de phenyle.
Bull. Soc. Chem. 11: 328. (Fre.)
Moriguchi, I. 1975. Quantitative structure-activity studies on parameters
related to hydrophobicity. Chem. Pharmacol. Bull. 23: 247.
A-4
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Weast, R.C. (ed.) 1977. Handbook of Chemistry and Physics. 58th ed. CRC
Press, Inc., Cleveland, Ohio.
Weast, R.C. (ed.) 1978-79. CRC Handbook of Chemistry and Physics. 59th
ed. CRC Press, Inc., West Palm Beach, Florida, p. 301.
A-5
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Aquatic Life Toxicology*
INTRODUCTION
The only toxicity data for haloethers, other than for those compounds dis-
cussed in the criterion document for chloroalkyl ethers, are for 4-bromophen-
ylphenyl ether and freshwater species, the bluegill, fathead minnow, and Daph-
nia magna.
EFFECTS
Acute Toxicity
Daphm'a magna has been exposed to 4-bromophenyl phenyl ether and is more
sensitive than the bluegill with a 48-hour EC5Q of 360 ug/l (Table 1).
The bluegill 96-hour LC5Q is 4,940 ug/l.
Chronic Toxicity
A chronic value for 4-bromophenylphenyl ether, 122 yg/1, is derived from
an embryo-larval test with the fathead minnow in which adverse effects on sur-
vival and growth were observed (Table 2). No acute-chronic ratio can be cal-
culated since no comparable acute value is available for this species.
Summary
Static, acute toxicity tests with freshwater organisms have been conducted
with the bluegill and Daphm'a magna and 4-bromophenylphenyl ether. The clado-
ceran is more sensitive with a species acute value of 360 yg/1 (Table 1). The
comparable value for the bluegill is 4,940 ug/1.
*The reader is referred to the Guidelines for Deriving Water Quality Cri-
teria for the Protection of Aquatic Life and Its Uses in order to better un-
derstand the following discussion and recommendation. The following tables
contain the appropriate data that were found in the literature, and at the
bottom of each table are calculations for deriving various measures of tox-
icity as described in the Guidelines.
B-l
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An embryo-larval test has been conducted with the fathead minnow and the
same haloether, but no acute-chronic ratio is calculable since no acute value
is available for this species.
No saltwater organisms have been tested with any haloether.
CRITERIA
The available data for haloethers indicate that acute and chronic toxicity
to freshwater aauatic life occur at concentrations as low as 360 and 122 ug/1,
respectively, and would occur at lower concentrations among species that are
more sensitive than those tested.
No saltwater organisms have been tested with any haloether and no state-
ment can be made concerning acute or chronic toxicity.
B-2
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Table 1. Acute values for haloethers (U.S. EPA, 1978)
Species
Cladoceran,
Daphnla magna
Bluegill,
Lepomis macrochirus
Method* Chemical
FRESHWATER SPECIES
S, U 4-bromopheny 1-
phenyl ether
S, U 4-bromopheny 1-
phenyl ether
LC50/EC50
(ug/U
360
4,940
Species Mean
Acute Value
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Table 2. Chronic values for haloethers (U.S. EPA, 1978)
Chronic
Limits Value
Species Test* Chemical (ng/l)
FRESHWATER SPECIES
03
I
Fathead minnow, ELS 4-bromopheny I- 89-167 122
Pimephales promelas phenyl ether
* ELS = early life stage
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REFERENCES
U.S. EPA. 1978. In-depth studies on health and environmental impacts of
selected water pollutants. U.S. Environ. Prot. Agency, Contract No. 68-01-
4646.
fl-5
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Mammalian Toxicology and Human Health Effects
INTRODUCTION
The U.S. EPA is currently charged with establishing water quality cri-
teria for haloethers. This document covers chlorinated aromatic ethers
including:
Chlorophenyl phenyl ethers
Bromophenyl phenyl ethers
Polychlorinated diphenyl ethers
A separate document in this series, entitled "Chloroalkyl Ethers,"
includes the following compounds:
Bis(chloromethyl)ether
Bis(2-chloroethyl)ether
2-Chloroethyl vinyl ether
Bis(2-chloroi sopropyl)ether
Bis(2-chloroethoxy)methane
C-l
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EXPOSURE
Ingestion from Water
Qualitative identifications of several haloethers in raw and finished
water have been reported. This information is summarized in Table 1. The
nomenclature used in specifying some haloethers creates a certain amount of
confusion in evaluating these monitoring data. For instance, in Table 1,
pentachlorophenoxy methyl ether is probably the same as pentachlorophenyl
methyl ether. The names used in Table 1 are those given in the various
cited references.
Shackelford and Keith (1976) have compiled information on the frequency
of organic compounds identified in water. This information was taken from
both published literature and unpublished results of survey analyses from
EPA regional and research laboratories. Although actual levels of the halo-
ethers in waters are not specified, a breakdown is given of the various
types of waters found to be contaminated. This information is presented in
Table 2.
The study by Ewing and his coworkers (1977) is based on the analysis of
204 water samples collected from 14 heavily industrialized river basins. As
indicated in Table 1, pentachlorophenyl methyl ether was found in 12 samples
(5.88 percent), with other chlorophenyl ethers found less frequently. As
indicated above, the reports of "pentachlorophenoxy methyl ether" probably
refer to pentachlorophenyl methyl ether. The studies by Friloux (1971) and
the U.S. EPA (1972), both listed in Table 1, were conducted in the New
Orleans area.
In the 1975 National Organics Reconnaissance Survey by the U.S. EPA, no
haloethers were found in the waters of Miami, Florida; Seattle, Washington;
Ottumwa, Iowa; or Cincinnati, Ohio (U.S. EPA, 1975).
C-2
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TABLE 1
Haloethers Qualitatively Identified in Water
(see text for details)
Reference
Haloethers
to
01
T3
S-
o
O)
o
(fl
cr.
o>
A
Cn
2
OJ
cn
x
3
o
Bromophenyl phenyl ether
Bis(4-chlorophenyl)ether
Oichlorophenyl chlorophenyl ether
2,4,4'-Trichloro-2'-hydroxy-
diphenyl ether
Dichlorophenyl methyl ether
Trichlorophenyl methyl ether
Tetrachlorophenyl methyl ether
Pentachlorophenyl methyl ether
Pentachlorophenoxy methyl ether
5*
2*
2*
1*
10"
1*
5*
1*
12*
2*
* Frequency of occurrence
X Occurrence reported, but without freauency
C-3
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TABLE 2
Frequency of Haloethers Identified in Various Types of Water3
FDW
Water Type Contaminated^
River
Raw Water
Effluent from:
CHEM
RS
STP
o
Bromophenyl phenyl ether
Bis(4-chloropheny1)ether
Oichlorophenyl chlorophenyl
ether
2,4,4'-Trichloro-2'-hydroxy-
diphenyl ether
Pentachlorophenyl methyl
ether
aSource: Shackelford and Keith, 1976
bFDW = Finished drinking water
CHEM = Chemical Plant
RS = Raw sewage
STP = Sewage treatment plant
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Ingestlon from Food
o monitoring data have been found on the levels of haloethers in food.
bioconcentration factor (BCF) relates the concentration of a chemical
ir .,- latic animals to the concentration in the water in which they 'ive.
The steady-state BCFs for a lipid-soluble compound in the tissues of •;-,, ous
aquatic animals seem to be proportional to the percent lipid in the ,; ae.
Thus the per capita ingestion of a lipid-soluble chemical can be estimated
from the pe ,-apita consumption of fish and shellfish, the weighted average
percent li; > of consumed fish and shellfish, and a steady-state BCF for
the chemicai
Data from a recent survey on fish and shellfish consumption in the
United States was analyzed by SRI International (U.S. EPA, 1980). These
data were used to estimate that the per capita consumption of freshwater and
estuarine fish and shellfish in the United States is 6.5 g/day (Stephan,
1980). In addition, these data were used with data on the fat content of
the edible portion of the same species to estimate that the weighted average
percent lipids for consumed freshwater and estuarine fish and shellfish is
3.0 percent.
No measured steady-state BCF is available for any of the following com-
pounds (Table 3), but the equation "Log BCF = (0.85 Log P) - 0.70" can be
used (Veith, et aK 1979) to estimate the steady-state BCF for aquatic or-
ganisms that contain about 7.6 percent lipids (Veith, 1980) from the oc-
tanol/water partition coefficient (P). Calculated log P values were ob-
tained using the method described in Hansch and Leo (1979). The adjustment
factor of 3.0/7.6 = 0.395 is used to adjust the estimated BCF from the 7.6
percent lipids on which the equation is based, to the 3.0 percent lipids
that is the weighted average for consumed fish and shellfish in order to ob-
C-5
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TABLE 3
Bioconcentration Factors for Haloethers
Chemical
2-Chlorophenyl
phenyl ether
3-Chlorophenyl
phenyl ether
4-Chlorophenyl
phenyl ether
4-Bromo phenyl
phenyl ether
Bis(4-chlorophenyl )
ether
2,4-Dichlorophenyl
phenyl ether
2,6-Dichlorophenyl
phenyl ether
3,5-Dichlorophenyl
Log P
Calc.
4.92
4.92
4.92
5.08
5.63
5.63
5.63
5.63
Estimated Steady
State BCF
3,030
3,030
3,030
4,150
12,200
12,200
12,200
12,200
Weighted
Average BCF
1,200
1,200
1,200
1,640
4,820
4,820
4,820
4,820
phenyl ether
C-6
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tain the weighted average bioconcentration factor for the edible portions of
all freshwater and estuarine aquatic organisms consumed by Americans.
Inhalation
No monitoring information is available on the levels of any haloethers
in ambient air.
Dermal
Because of the lack of monitoring data, no evaluation of the importance
of dermal exposures can be made for the haloethers.
PHARMACOKINETICS
Pertinent data could not be located in the available literature con-
cerning the pharmacokinetics of haloethers.
EFFECTS
Acute, Subacute, and Chronic Toxicity
The acute and subacute oral toxicity of various chlorinated phenyl
ethers is summarized in Tables 4 and 5. Because of the lack of experimental
detail presented in this summary of unpublished data by Hake and Rowe
(1963), these results are difficult to interpret. However, the reported
results on "highly purified" pentachlorophenyl ether compared to the other
pentachlorophenyl ether (i.e., "unpurified") suggest that impurities may be
major toxic constituents.
Hake and Rowe (1963) report that "small amounts" of hexachlorodiphenyl
ether may cause acneform dermatitis in man.
Synergism and/or Antagonism, Teratogenicity, Mutagenicity, and Carcinogeni-
city
Pertinent data could not be located in the available literature.
C-7
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TABLE 4
Chlorinated Phenyl Ethers: Summary of Single-dose
Oral Feeding Studies on Guinea Pigs*
o
i
00
Total Number
of Chlorines
1 x Cl
2 x Cl
3 x Cl
4 x Cl
5 x Cl
6 x Cl
After 4
Lethal Dose
(nig/kg)
700
1,300
2,200
3,000
3,400
3,600
Days
Survival
Dose (mg/kg)
200
400
400
400
1,800
400
After
Lethal Dose
(mg/kg)
600
1,000
1,200
50
100
50
30 Days
Survival
Dose (mg/kg)
100
50
200
0.5
5
5
*Source: Hake and Rowe, 1963
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TABLE &
Chlorinated Phenyl Ethers:
Results of Repeated Oral Feeding of Rabbits3
o
Total
Number of
Chlorines
1
2
3
4
5
6
Dose
(mg/kg)
100
100
100
50
10
50
5
50
100**
10**
I**
5
1
0.1
Number of
Doses*
19
19
5
20
20
4
20
8
20
20
20
8
20
20
Number of
Days
29
29
12
29
29
10
29
21
29
29
29
10
28
28
Effect
None
Mild liver injury
Death
Slight liver
No effect
Death
Severe liver
Death
injury
injury
Moderate liver injury
No growth
Slight liver
No effect
Death
Severe liver
No effect
injury
injury
*Animals dosed 5 days/week x 4 weeks unless death intervened.
**Highly purified pentachlorophenyl ether
aSource: Hake and Rowe, 1963
Vehicles not specified.
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CRITERIA FORMULATION
Existing Guidelines and Standards
The Occupational Safety and Health Administration (29 CFR 1910.1000) has
set a time-weighted average value of 500 Mg/m3 for the following aromatic
chloroethers in the air of the working environment: monochlorophenyl phenyl
ether, dichlorophenyl phenyl ether, trichlorophenyl phenyl ether, tetra-
chlorophenyl phenyl ether, and pentachlorophenyl phenyl ether. This value
has also been adopted by the American Conference of Governmental and Indus-
trjal Hygienists (1974). The standard is designed to prevent chloracne in
exposed workers.
Current Levels of Exposure
As detailed in the Exposure section, only limited information is avail-
able on the extent of human exposure to haloethers in water, and no informa-
tion is available on ambient levels of haloethers in air or food. Quantita-
tive estimates of human exposure cannot be made.
Special Groups at Risk
Individuals working with haloethers or living in areas where these halo-
ethers are produced are probably at greater risk than the general population.
Basis and Derivation of Criteria
As indicated, the Threshold Limit Value (TLV) for chlorophenyl phenyl
ethers is 500 ng/m . By a process analogous to that used by Stokinger and
Woodward (1958), this standard could be used to calculate a water criterion.
However, since the TLV for these compounds is based on preventing chloracne
rather than chronic toxicity, such a calculation would not be appropriate.
Because of the paucity of toxicologic data on the compounds covered in
this document, no ambient water quality criteria for the protection of human
health can be derived. It should be recognized that many halogenated
aromatic compounds display significant toxicologic properties (McConnell and
C-10
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Moore, 1979). Consequently, the inability to derive criteria for the halo-
ethers is a matter of concern which should be addressed by additional
research.
C-ll
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REFERENCES
American Conference of Governmental Industrial Hygienists. 1974. Documen-
tation of the Threshold Limit Values. 3rd ed. Cincinnati, Ohio.
Ewing, B.B., et al. 1977. Monitoring to detect previously unrecognized
pollutants in surface waters. EPA 560/6-7-015. p. 75.
Friloux, J. 1971. Petrochemical wastes as a pollution problem in the lower
Mississippi River. Paper submitted to the Senate Subcommittee on Air and
Water Pollution, April 5.
Hake, C.L. and V.K. Rowe. 1963. Ethers. In: F.A. Patty (ed.), Industrial
Hygiene and Toxicology, 2nd ed. Interscience Publishers, New York. 2: 1655.
Hansch, C. and J. Leo. 1979. Substituent Constants for Correlation Analy-
sis in Chemistry and Biology. Wiley-Interscience, New York.
McConnell, E.E. and J.A. Moore. 1979. Toxicopathology characteristics of
the halogenated aromatics. Ann. N.Y. Acad. Sci. 320: 138.
Shackelford, W.M. and L.H. Keith. 1976. Frequency of organic compounds
identified in water. EPA 600/4-76-062, U.S. Environ. Prot. Agency, Athens,
Georgia, p. 626.
Stephan, C.E. 1980. Memorandum to J. Stara. U.S. EPA. July 3.
C-12
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Stokinger, H.E. and R.L. Woodward. 1958. Toxicologic methods for estab-
lishing drinking water standards. Jour. Amer. Water Works Assoc. 50: 515.
U.S. EPA. 1972. Industrial pollution of the lower Mississippi River in
Louisiana. Region VI, Dallas, Texas, Surveillance and Analysis Division.
U.S. EPA. 1975. Preliminary assessment of suspected carcinogens in drink-
ing water. Interim Report to Congress, Washington, D.C.
U.S. EPA. 1980. Seafood consumption data analysis. Stanford Research In-
stitute International, Menlo Park, California. Final Report, Task 11, Con-
tract No. 68-01-3887.
Veith, G.D. 1980. Memorandum to C.E. Stephan. U.S. EPA. April 14.
Veith, G.D., et al. 1979. Measuring and estimating the bioconcentration
factors of chemicals in fish. Jour. Fish. Res. Board Can. 36: 1040.
a U S GOVERNMENT PRINTING OFFICE • 1980 720-016/5961
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