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
                                    C-13

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