EPA-560/8-75-002
             ENVIRONMENTAL HAZARD ASSESSMENT REPORT
                 HIGHER BENZENEPOLYCARBOXYLATES
                          NOVEMBER 1975
                 ENVIRONMENTAL PROTECTION AGENCY
                   OFFICE OF TOXIC SUBSTANCES
                     WASHINGTON,  D,C,   20460

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ENVIRONMENTAL HAZARD ASSESSMENT REPORT
    Higher Benzenepolycarboxylates
              Prepared by
      Office of Toxic Substances
    Environmental Protection Agency
       Washington, D. C.  20460
             November  1975

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                          TABLE  OF CONTENTS
     PREFACE
     CONCLUSIONS' AND'RECOMMENDATIONS!
     SUMMARY OF TECHNICAL ASPECTS....
I.   GENERAL INFORMATION	
II.  ENVIRONMENTAL ASPECTS	
III. BIOLOGICAL ASPECTS	
     REFERENCES	
                                       11
                                        1
                                        2
                                        4
                                       11
                                       13
                                       16
                            LIST OF FIGURES
Figure 1.      Chemical Structures of the Higher
               Benzenepolycarboxylates	
                            LIST OF TABLES
Table I.



Table II.




Table III.
Some Available Physical Data for
Higher Benzenepolycarboxylates...
the
Producers of the Commercially Sig-
nificant Higher Benzenepolycarbox-
ylates	


Inhibition of cis-Aconitase by
Various Benzenepolycarboxylic Acids
at 10 mM	
                                                      14

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                                PREFACE

     Our society uses thousands of chemical  substances with many
of them released into the environment in varying quantities as
production or handling losses, as waste materials, or as a direct
consequence of intended or unintended uses.   Concern over possible
effects of these chemicals has prompted the  establishment of a
program by the Early Warning Branch of The Office of Toxic Sub-
stances to review release, exposure, and effects data to assist in
setting priorities for further study or possible regulatory action.
     Detailed analyses on every commercial chemical are not prac-
tical. Selected materials are initially screened by a simple
literature search and a limited number of these chemicals are
selected for more detailed study .  Criteria for this selection
include volume of production, manner of use, market growth poten-
tial, exposure patterns, detection in the environment, known toxic
effects, and functional or chemical relationships to known environ-
mental pollutants.  The early warning system, which first brings
chemicals to the attention of the program uses diverse sources,
including opinions of experts, referrals from other units of
government, reports in the scientific and trade literature,
predictive modelling, and public inquiries.   Much of the initia-
tive for this study was stimulated by the recently proposed new
use of the higher benzenepolycarboxylates as detergent builders in
nitrogen- and phosphorous-free formulations.  The potential for
widespread environmental release from such a use was a real
concern.
     These hazard assessments are prepared from reviews of the
subject substances supplemented by additional searches and inquir-
ies to obtain the most complete and recent information available.
Only data considered pertinent to an assessment of environmental
hazard are reported in this series.

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  :   Although the assessment uses as complete an information base as
possible, additional information may be available or may become available.
Therefore, these assessments are subject to revisions.   The Office of
Toxic Substances would welcome any additional pertinent data.

     Recommendations in this document are those of the Office of Toxic
Substances and may not represent an Agency consensus.  Nor do they
represent commitment to further action by the Environmental Protection
Agency or any other organization.  Mention of tradenames and manufacturers'
of  specific  products in this document  is  for purposes of clarity and
specificity  only and does not constitute an endorsement of any product.
     This report was written by Frank J. Letkiewicz.  The Environmental
Hazard Assessment Series is being prepared under the guidance of Dr.
Farley Fisher, Chief of the Early Warning Branch, Office of Toxic
Substances.
     The  literature review which preceded this assessment was conducted
by  Dr. Philip Howard and Mr. Patrick Durkin of the Syracuse University
Research  Corporation, Syracuse, New York.  That review was supplemented
by  consultations with selected knowledgeable individuals both within and
outside the  Federal Government and is part of a report entitled Pre-
liminary  Environmental Hazard Assessment of Chlorinated Naphthalenes,
Silicones, Fluorocarbons, Benzenepolycarboxylates and Qhlorophenols,
available through the National technical Information Service, Spring-
field, Virginia  22151 (NTIS accession number - PB-238 074/AS).
     Appreciation is expressed to the many individuals who provided
information  and reviewed drafts of this report.  Special appreciation is
expressed to the Office of Toxic Substances staff and to Dr. M. Schnitzer
of  the Soil  Research Institute, Central Experimental Farm, Canada, for
exchanges on the occurrence of benzenepolycarboxylates in soil humic
substances.  Additional technical reviews, comments and suggestions
incorporated into this report were contributed by Dr. Delbert S. Barth,
Director, EPA/NERC-Las Vegas; Robert E. McGaughy, EPA Office of

                              - iii -

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Research and Development, Health Effects Division, Washington, D.C.; Dr.
Norman R. Glass, Director, National Ecological  Research Laboratory,
EPA/NERC-Corvallis; Dr. Donald I. Mount, Director, EPA National Water
Quality Laboratory, Duluth; Dr. Charles F. Jelinek, FDA, Bureau of
Foods, Division of Chemical Technology, Washington, D.C.; Joan Davenport,
Acting Director, EPA Office of Enforcement and General Counsel, Office
of Technical Analysis; and Dr. Lawrence A. Plumlee, Medical Science
Advisor, EPA Office of Research and Development.

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                 CONCLUSIONS AND RECOMMENDATIONS

     Available data on the toxicity and ecological effects and on
the levels of environmental exposure to the higher benzenepolycar-
boxylates are insufficient to assess adequately the hazards to man
and the environment posed by these chemicals.  Since current uses
of and practices concerning these chemicals do not result in
significant losses to the environment, attempts to gather these
data cannot be justified at this time; such attempts should be
made if a new use or practice begins to disperse the chemical to
the environment.  Specific information which would be needed
includes:
     1.   Environmental fate, degradation, products formed,
          and the extent to which the compounds are incorporated
          into humic substances;
     2.   Health effects resulting from chronic exposure to the
          compounds if they are not readily degraded or incorpor-
          ated into humic substances; and
     3.   Health effects of any degradation products.

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                     SUMMARY OF TECHNICAL ASPECTS

     The higher benzenepolycarboxylates, as defined herein,  are
the benzenetricarboxylates through benzenehexacarboxylate.   Only
three members of this group of compounds have reported commercial
uses, but no detailed production figures are available.   Trimel-
litic anhydride (benzene-1,2,4-tricarboxylic acid,  1,2-anhydride)
is used to produce plasticizers, various resins, dyes, and  other
chemical intermediates.  Trimesic acid (benzene-1,3,5-tricarboxylic
acid) is currently used as a crosslinking agent in  solid propel-
lant fuels.  Pyromellitic dianhydride (benzene-1,2,4,5-tetracar-
boxylic acid, dianhydride) is used as a crosslinking  agent  and
curing agent for epoxy resins and in the production of polyimides,
a class of high-temperature-resistant specialty resins used in
aero-space and electrical applications.

     While the present view of the chemical structure  of humi'c
substances (the organic fraction of soil and water) is that it is
comprised of benzenepolycarboxylic and phenolic acids, joined by
hydrogen bonds, the extent to which benzenepolycarboxylates occur
naturally as "free" acids in the soil solution and  in  water is
believed to be exceedingly small.

     No standards or regulations directly or indirectly control-
ling these substances are known to exist.

     Toxicity data exist only for acute oral exposure  to trimel-
litic acid and trimellitic anhydride where the LD5Q values  suggest
no acute exposure hazard at environmentally realistic  levels.  No
information on general biological effects (such as  carcinogen-
icity, mutagenicity, etc.) was found in the literature.
                               - 2 -

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     One study indicated the ability of trimesic,  trimellitic and
pyromellitic acids to significantly inhibit cjs^-aconitase,  an enzyme of
the Krebs cycle.  The Krebs cycle is a cellular mechanism for obtaining
and storing chemical potential  energy from metabolized protein,  fat and
carbohydrates.  This study which used an isolated  enzyme preparation is
only indicative of a potential  for inhibition by these compounds in
whole plants or animals.

     From the available information it has been concluded that,  although
the fate and possible effects of these compounds in the environment are
not characterized, the current uses of the higher  benzenecarboxylates as
chemical intermediates are not resulting in significant environmental
release.  It is recommended, however, that, prior  to the initiation of
any potentially dispersive new use(s), fate and effects information be
obtained.
                              - 3 -

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I.   GENERAL.INFORMATION (including production and use)

     In the early 1970's, widely used phosphorus-containing detergent
builders were recognized as promoters of eutrophication.  (A builder is
any ingredient, such as water softener, sequestering or buffering agent,
that increases the detergent power of a soap or synthetic surfactant.)
Use of detergent formulations employing these builders contributed
significantly to water pollution problems by promoting algal growth in
both municipal wastes and freshwater bodies.
     Consequently, alternative builders were sought by the detergent
industry.  One group of compounds that has been proposed for use was the
benzenepolycarboxylates. An initial literature search revealed that
little was known about this group of compounds.  Because of this, and
because of the potential for wide dispersal in the environment should
these compounds be incorporated into detergent formulations, the benzene-
polycarboxylates were selected for the environmental hazard assessment
series.
     In this paper, the term "higher benzenepolycarboxylates" is used to
include the benzenetricarboxylates through benzenehexacarboxylate, the
chemical structures for which are shown in Figure 1. The abbreviations
used herein for these compounds are also given in Figure 1.  Howard and
Durkin (1974) have presented a literature review on all the benzenepoly-
carboxylates.

     Physically, these compounds are white crystalline solids or powders
with high melting points and varying degrees of water solubility.  Some
available data for these compounds are shown in Table I.  These compounds
would be expected to show the chemical behavior typical to carboxylate
compounds, such as the formation of water soluble alkali (sodium,
potassium) and ammonium salts, and the conversion to acid chlorides,
esters, amides, and, where the carboxylic acid groups are ortho to each
other on the ring, anhydrides.
                              - 4 -

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  Figure 1.  Chemical Structures of the Higher Benzenepolycarboxylates
                                    COOH
          CQOH
                COOH
                CODE

  Benzene-1,2,3-tri-
    carboxylic acid
  Hemimellitic acid
  (HMA)
Benzene-1,2,3-tricarboxylic
  acid, 1,2-dianhydride
Hemimellitic anhydride
(HMAN)

             COOH
                     0
                               HOOC
                  'COOH
            COOH
  Benzene-1,2,4-tricarboxylic
    acid, 1,2-dianhydride
  Trimellitic anhydride
  (THAN)
     Benzene-1,3,5-tri-
       carboxylic acid
     Trimesic acid
     (TMSA)
         COOH
HOOC
               COOH
               COOH
    HOOC
                               HOOC
COOH
                  COOH
  Benzene-1,2,3,5-tetra-
    carboxylic acid
  Prehnitic acid
     Benzene-1,2,4,5-tetra-
       carboxylic acid
     Pyromellitic acid
     (PMA)
                                                               COOH
                                          COOH
                  COOH
                 Benzene-1,2,4-tri-
                   carboxylic acid
                 Trimellitic acid
                 (TMA)
                                               COOH
                                                                          COOH
                                                                    COOH
                 Benzene-1,2,3,4-tetra-
                   carboxylic acid
                 Mellophanic acid
                 Benzene-1,2,4,5-tetra-
                   carboxylic acid,
                   dianhydride
                 Pyromellitic dianhydride
                 (PMDA)
                               -5-

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                      Figure 1.  (cont.)
            COOH
     HOOC
                  COOH
                  COOH
             COOH
Benzenepentacarboxylic acid
                                                  COOH
                                                       COOH
HOOC  "V   COOH
        COOH

  Benzenehexacarboxylic acid
  Mellitic acid
  (MA)
                                   -6-

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Night Vision  and Dark Adaptation (98)
    Feb 76
    NTIS/PS-76/0133/9GSB
Building Technology

Structural  Foundations  in Soils,  Ice,
    Snow, and Permafrost. Vol. 1. 1964-
    1971 (135) Jan  75 Excludes  sub-
    way and seabed construction
    NTIS/PS-75/282/4GSB

Structural  Foundations  in Soils,  Ice,
    Snow, and Permafrost. Vol. 2. 1972-
    1974 (57) Jan  75 Excludes subway
    and seabed construction
    NTIS/PS-75/283/2GSB

Construction Management  (103)  Apr 75
    NTIS/PS-75/352/SGSB

Architectural   Construction   Materials.
    Part 1. Non Concrete (189) May 75
    Excludes concretes, bridges, pave-
    ments,  airfields, cold weather con-
    struction,     composites,     and
    earthquake resistant construction
    NTIS/PS-75/389/7GSB

Architectural   Construction   Materials.
    Part 2. Concrete and Cement  (127)
    May  75 Excludes   non-concretes,
    bridges, pavements, airfields, cold
    weather construction, composites,
    and earthquake resistant  construc-
    tion
    NTIS/ PS-7S/ 390/5GS B

Construction Equipment (174) May 75
    Excludes translations
    NTIS/PS-75/391/3GSB

Cold Weather Construction (99) May 75
    Excludes permafrost construction
    NTIS/PS-75/394/7GSB

Structural  Mechanics  Software  (185)
    May 75
    NTIS/PS-75/428/3GSB

Stress  Crack Phenomena  (186) Jun 75
    Excludes  rock   mechanics   and
    mathematical analysis
    NTIS/ P S-75/46S/SGS B

Mathematical Analysis of Stress Cracks.
    Vol 1. 1964-1973 (207)  June 75
    NTIS/PS-7S/466/3GSB

Mathematical Analysis of Stress Cracks.
    Vol 2. 1974-May 75 (109) June 75
    NTIS/PS-75/467/1GSB

Concrete Polymer Composites (90)  Jun
    75
    NTIS/PS-75/475/4GSB

Finite  Elements in Structural  Analysis
    (70) Jun 75
    NTIS/PS-75/496/OGSB

Industrialized Housing (183) Jul 75
    NTIS/PS-75/571/OGSB

Earthquake   Engineering:   Buildings,
    Bridges, Dams  and  Related  Struc-
    tures. Vol 1. (172)  1964-1973
    NTIS/PS-75/632/OGSB

Earthquake   Engineering:   Buildings,
    Bridges, Dams, and Related  Struc-
    tures. Vol.2. (127)  1974-Jul75
    NTIS/PS-75/633/8GSB

Building Fires  (137) Sep 75
    NTIS/PS-75/652/8GSB

Solar Space Heating and Air Condition-
    ing (123) Sep 75
    NTIS/ P S-75/689/OGS B

Fire  Alarms and  Fire Detectors  (120)
    Oct 75
    NTIS/PS-75/793/OGSB

-------
Pine  Wood (65) Oct  75 Covers  pine
    wood products, uses, and properties
    NTIS/PS-75/798/9GSB

Wood Bonding (99) Dec 75
    NTIS/PS-75/861/5GSB

Wind  Effects.  Part 1.  Buildings  and
    Bridges (83)  Dec 75
    NTIS/PS-75/870/6GSB

Wind Effects. Part 2. General Structures
    (67) Dec 75 Excludes buildings and
    bridges
    NTIS/PS-75/871/4GSB

Prestressed Concrete Technology  (181)
    Feb 76
    NTIS/PS-76/0098/4GSB

Particle  Boards and Fiberboards:  Fabri-
    cation,  Use,  and Properties  (115)
    Feb 76
    NTIS/PS-76/0157/8GSB

Particle  Boards:  Fabrication, Use,  and
    Properties. (154) Mar 76 (£/)
    NTIS/ PS-76/0158/ 6GSB

Fiberboards: Fabrication, Use, and Pro-
    perties. Vol. 1. 1970-1974 (223)  Mar
    76  (£/)
    NTIS/ PS-76/0159/4GSB

Fiberboards: Fabrication, Use, and Pro-
    perties. Vol. 2. 1975-Jan 1976 (121)
    Mar 76  (Ei)
    NTIS/PS-76/0160/2GSB

Aircraft Sonic Boom. Part 2. Effects on
    Buildings  (64) Mar 76
    NTIS/PS-76/0176/8GSB


Medicine and  Biology

Ecosystem Models (144) Jan 74
    NTIS/PS-75/088/5GSB

Interferon (157) Jan 75
    NTIS/PS-75/100/8GSB

Ecology of  Insecticide  Water Pollution
    Vol 2. 1964-1973 (203) Jan 75
    NTIS/PS-75/108/1GSB

Drug Abuse (113) Jan 75
    NTIS/PS-75/147/9GSB

Cold Weather Stress on Humans (72)
    Jan 75
    NTIS/PS-75/170/1GSB

Radiology (102) 1967-Jan 75
    NTIS/PS-75/173/5GSB

Ultrasonics in Medicine (39)  Jan 75
    NTIS/PS-75/175/OGSB

Prostaglandins (37) 1967-Jan 75
    NTIS/PS-75/176/8GSB

Biological Effects of Mercury Pollution
    (112) Dec 74
    NTIS/PS-75/210/5GSB

Nuclear Medicine (218)  Jan 75
    NTIS/PS-75/213/9GSB

Tumor Immunology (51)  1964-Sept 73
    NTIS/PS-75/222/OGSB

Psychoses  (85) Jan 75
    NTIS/PS-75/235/2GSB

Hyperbaric  Oxygenation (125) Jan 75
    NTIS/PS-75/236/OGSB

Altitude Hypoxia  (166)  Jan 75
    NTIS/PS-75/ 237/ 8GSB
Forensic Medicine  (39) Jan 75
    NTIS/PS-75/245/1GSB

Hemophilia (22)  Jan 75
    NTIS/PS-75/260/OGSB

Chronic Obstructive Lung Disease (24)
    Jan 75
    NTIS/PS-75/273/3GSB

Underwater  Medicine  and  Physiology
    (191) Jan 75
    NTIS/PS-75/278/2GSB

Malaria. Vol 1. 1964-1970 (174)  Feb 75
    NTIS/PS-75/307/9GSB

Malaria. Vol 2. 1971-1974 (64) Feb 75
    NTIS/PS-75/308/7GSB

Oral Diseases and  Preventive Dentistry
    (119) Feb 75
    NTIS/P S-75/315/2G S B

Ecology  of  the Marine  Environment
    (205) Feb 75
    NTIS/PS-75/329/3GSB

Leukemia  (134) Feb 75
    NTIS/PS-75/339/2GSB

Dental Materials and Equipment (143)
    Feb 75
    NTIS/PS-75/340/OGSB

Schistosoma and Schistosomiasis (130)
    Feb 75
    NTIS/PS-75/344/2GSB

Septicemia (158) Feb 75
    NTIS/PS-75/349/1GSB

GRAS(Generally  Recognized . as  Safe)
    Food Ingredients  (253) April 75
    NTIS/PS-7S/356/6GSB

Medical Entomology. Vol. 2.  1970-1975
    (192) 1970-Jan 1975
    NTIS/PS-75/360/8GSB

Medical Entomology.  Vol.1.1964-1969
    (157) 1964-1969
    NTIS/PS-75/361/6GSB

Hemorrhagic Shock (70) 1964 - Apr 75
    NTIS/PS-75/369/9GSB

Biological  Effects of Microwaves (112)
    Mar 75
    NTIS/P S-75/ 384/ 8GS B

Toxicity of Gaseous Halocarbons (70)
    May 1975
    NTIS/PS-75/387/1GS B

Artificial Kidneys (182) 1968-Apr75
    NTIS/PS-75/418/4GSB

Blindness  (113) May 75
    NTIS/PS-75/427/5GS B

Radioactivity from Nuclear Power Plants
    (227) May 75
    NTIS/P S-75/429/1GSB

Sewage Effects in Marine and Estuarine
    Environments (136) May 75
    NTIS/PS-75/ 430/9GSB
Cyanoacrylate   Tissue  Adhesives (48)
    1964-May 75
    NTIS/PS-75/440/8GSB

Psychotropic    Drug    Research (114)
    1964-May 1975
    NTIS/PS-75/ 489/5GSB

Preventive Medicine (107) Jun 75
    NTIS/PS-75/502/5GSB
Computer Technology in Medicine  (192)
    1972-Jun 7
    NTIS/PS-7S/507/4GSB

Cryobiology (106) Jun-75
    NTIS/PS-75/508/2GSB

Antineoplastic agents (195)  1970-Jun 75
    NTIS/PS-75/509/OGSB

Sickle Cell Anemia  (38) Jun 75
    NTIS/ PS-75/515/7GSB

Eutrophication.  Vol  1.  1964-1973 (194)
    Jun 75
    NTIS/PS-75/522/3GSB

Eutrophication.  Vol  2.  1974-June 1975
    (86) Jun 75
    NTIS/PS-75/523/1GSB

Electroretinography  (87) Jun 75
    NTIS/PS-75/526/4GSB

Health  Services in Rural Areas (87) Jun
    75
    NTIS/PS-75/532/2GSB

Hepatitis and Blood Transfusions  (58)
    Jul 75
    NTIS/PS-75/543/9GSB

Radiation    Effects   on   Cells   and
    Chromosomes (109) Jun 75
    NTIS/PS-75/551/2GSB

Mine   Safety.   Part  3.  Occupational
    Health—General   Studies (110) Jun
    75
    NTIS/PS-75/564/5GSB

Mine   Safety.   Part  4.  Occupational
    Health-Radioactivity (49) Jun 75
    NTIS/PS-75/565/2GSB

Immunologic Diseases. Vol 2. 1975  (62)
    Jul 75
    NTIS/PS-75/578/5GSB

Immunologic Diseases. Vol 1. 1964-1974
    (237) Jul 75
    NTIS/PS-75/579/3GSB

Aquatic Weed Control (93) Jul 75
    NTIS/PS-75/581/9GSB

Nerve Regeneration  (35) Jul 75
    NTIS/PS-75/592/6GSB

Nitrogen Oxide  Air Pollution.  Part 4.
    Biological Effects (49) Jul 75
    NTI S/ PS-75/610/6GSB

Motor Vehicle Operator Behavior (119)
    Aug 75  Excludes studies on the ef-
    fects of stress,  alcohol,  and vision
    characteristics
    NTIS/PS-75/619/7GSB

Driver   Performance under Abnormal
    Conditions.   Physical   Impairment,
    Drugs, Gases (43)  Aug 75 Excludes
    alcohol effects
    NTIS/PS-75/620/5GSB

Anthropometry (203) Aug 75
    NTIS/PS-75/629/6GSB

DDT, ODD,  and  DDE  Pesticides (150)
    Jul 75
    NTIS/PS-75/ 640/3GSB

-------
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-------
 Explosives  and   Narcotics  Detection
     Using Dogs (29) Sep 75
     NTIS/PS-75/648/6GSB

 Polychlorinated  Biphenyls  in the  En-
     vironment (52)  Sep 75
     NTIS/PS-75/713/8GSB
 Oyster Utilization, Biology, and Growth
     (205) Sep 75
     NTIS/PS-75/718/7GSB

 Asbestos and  Silicate  Pollution (111)
     Oct   75 Includes   silicosis   and
     asbestosis
     NTIS/PS-75/746/8GSB
 Toxicity of Pesticides  (188)  Oct 75
     NTIS/PS-75/756/7GSB
 Venereal Diseases  (54) Aug 75
     NTIS/PS-75/777/3GSB

 Blood Preservation  and Storage. Vol. 1.
     1964-1973 (169) Oct 75
     NTIS/PS-75/778/1GSB
 Blood Preservation  and Storage. Vol. 2.
     1974-1975 (52)  Oct 75
     NTIS/PS-75/779/9GSB

 Vaccines and Immunity (187)  Oct 75
     NTIS/PS-75/781/5GSB

 Bioindicators of Pollution (167) Nov 75
     NTIS/PS-75/796/3GSB

 Transplantation  Immunology (122) Oct
     75
     NTIS/PS-75/799/7GSB

 Industrial Health  Hazards  Due  to  At-
     mospheric  Factors (202) 1970-Aug
     75
     NTIS/PS-75/800/3GSB

 Chemical and Biological Warfare. Part 3.
     Biology,  Chemistry,  Therapy,  and
    Toxicology  (115) Oct  75 Excludes
    the  biochemistry  .and  therapy  of
    cholinesterase inhibitors
    NTIS/PS-75/834/2GSB

 Chemical and Biological Warfare. Part 4.
    Defoliants  and   Herbicides (126)
    Nov 75
    NTIS/PS-75/835/9GSB
 Biochemistry    and    Therapy     of
    Cholinesterase   Inhibitors  (139)  Nov
    75 Primarily       covers       or-
    ganophosphorus nerve agents
    NTIS/PS-75/837/5GSB
 Lung Cancer (81) Nov 74
    NTIS/PS-75/841/7GSB
 Environmental  Carcinogens  (158) Oct
    75
    NTIS/PS-75/844/1GSB
 Ecosystem Models  (214) Nov 75
    NTIS/PS-75/846/6GSB
Congenital Abnormalities (79)  Nov 75
    NTIS/PS-75/849/OGSB

Information Processing in Humans. Vol
    1. 1964-1973 (209)  Dec 73
    NTIS/PS-75/857/3GSB
Information Processing in Humans. Vol
    2. 1974-Nov 75  (89) Nov 75
    NTIS/PS-75/858/1GSB

Fish Protein Concentrates (140) Dec 75
    NTIS/PS-75/862/3GSB

Shark  Behavior  and  Biology (68)  Dec
    75
    NTIS/PS-75/869/8GSB
 Contraceptives and  Birth Control  (51)
    Dec 75
    NTIS/PS-75/880/5GSB
 Endangered Species (39)  Dec 75
    NTIS/PS-75/881/3GSB

 Biofeedback (36) Dec 75
    NTIS/P S-75/885/4GS B

 Biological Pest Control (71)  Dec 75
    NTIS/P S-75/887/ OG S B

 Epilepsy (66)  Dec 75
    NTIS/PS-7S/889/6GSB

 Stress  Factors on  Pilot  Performance
    (94) Dec 75
    NTIS/P S-75/890/4GS B
 Biomedical  Information Systems (178)
    Dec 75  Bibliographic and  data in-
    formation systems are included
    NTIS/PS-75/891/2GSB
 Biological Effects of Laser  Radiation
    (188) Dec 75
    NTIS/PS-75/893/8GSB

 Molecular Biology (131) Dec 75
    NTIS/PS-76/0001 /8GS B
 Impacts and  Sudies of  the Extremely
    Low  Frequency   Communication
    System, Sanguine  (106) Jan 76 In-
    cludes environmental and biological
    effects of this  global  communica-
    tions system
    NTIS/PS-76/0003/4GSB
 Auditory Perception  in Cetacea (70) Jan
    76
    NTIS/PS-76/0008/3GSB
 Behavior  and Physiological  Effects of
    Noise. Vol 1.  1964-1972 (199)  1964-
    Oct72
    NTIS/PS-76/0013/3GSB
 Behavior  and Physiological  Effects of
    Noise. Vol 2.  1972-1975 (119)  1972-
    Dec 75
    NTIS/ PS-76/0014/1GS B

 Air Pollution  Effects on  Plants (173)
    Dec 75
    NTIS/PS-76/0015/8GSB

 Rehabilitation  of  the  Physically   Han-
    dicapped (179) Jan 76
    NTIS/PS-76/0028/1GSB

 Biodeterioration  of  Oil  Spills (99) Jan
    76
    NTIS/PS-76/0032/3GSB
 The Biological Effects of Oil Spills  (142)
    Jan 76 Excludes  biodeterioration
    NTIS/PS-76/0033/1GSB

 Ecology of Insecticide  Water Pollution.
    Vol 1. 1964-1973  (206) Jan 76
    NTIS/PS-76/003S/6GSB
 Ecology of Insecticide  Water Pollution.
    Vol 2. 1974-1975  (152) Jan 76
    NTIS/PS-76/0036/4GSB
 Biological Productivity  in Fresh Water
    Environments  (140) Jan 76
    NTIS/ PS-76/0056/2GS B
Color Vision  Jan 76
    NTIS/PS-76/0059/6GSB

Rehabilitation of the Mentally Retarded
    (125) Feb 76
    NTIS/ P S-76/0067/9GS B
Cigarette Smoking (60)  Feb 76
    NTIS/P S-76/0074/5GS B
 Emergency  Medical Services (160) Feb
    76
    NTIS/PS-76/0080/2GSB

 Herpes Virus (115) Feb 76
    NTIS/PS-76/0093/5GSB

 Effects of Fatigue on Human  Behavior
    and Performance (121) Jan 76
    NTIS/PS-76/0095/OGSB
 Biological  Effects of Lead  Pollution
    (117) Feb 76
    NTIS/PS-76/0097/6GSB

 Burn Therapy (157)  Feb  76
    NTIS/ PS-76/0104/ OGSB
 Whales (115) Feb 76
    NTIS/PS-76/0111/SGSB
 Cardiovascular  Diseases. Vol.  1.  1964-
    1972 (151)  1964-1972
    NTIS/PS-76/0117/2GSB
 Cardiovascular  Diseases. Vol.  2.  1973-
    1975 (179)  Mar 76
    NTIS/PS-76/0118/ OGSB
 Bacterial  Pollution of Water (206) Feb
    76
    NTIS/PS-76/0120/6GSB
 Radioimmunoassay Studies (79) Feb 76
    NTIS/PS-76/0125/5GSB

 Thermal Pollution. Part 2. Biological Ef-
    fects. Vol 1. 1964-1973  (132) Mar 76
    NTIS/PS-76/0128/9GSB

 Thermal Pollution. Part 2. Biological Ef-
    fects. Vol 2. 1974-March 1976 (132)
    Mar 76
    NTIS/ PS-76/0129/ 7GSB
 Night  Vision and Dark Adaptation  (98)
    Feb 76
    NTIS/PS-76/0133/ 9GSB
 Nystagmus  (209) Mar 76
    NTIS/PS-76/0143/8GSB
Tumor Viruses (76) Feb 76
    NTIS/PS-76/0172/7GSB

Aircraft Sonic Boom. Part  3. Biological
    Effects  (66) Mar 76
    NTIS/PS-76/0177/6GSB
Hypertension  (97)  Mar 76
    NTIS/PS-76/0179/2GSB

 Natural Resources

 Remote Sensing for Natural Resource,
    Environmental,    and     Regional
    Planning (91) 1973-Jan 75
    NTIS/PS-75/104/OGSB

 Coal Mine Waste (51) Dec 74
    NTIS/PS-75/112/3GSB

 Mine Ventilation (66) Jan 75
    NTIS/PS-75/196/6GSB

 Oil    Recovery  (86)  Jan    75 Excludes
    offshore drilling
    NTIS/PS-75/254/3GSB

 Seismic Detection. Part 1. General  Stu-
    dies (82) Jan  75  Excludes detec-
    tion of nuclear events.
    NTIS/PS-75/326/9GSB

Aeration  of  Sewage  Lagoons, Reser-
    voirs, and Streams (157)  Apr 75
    NTIS/PS-75/357/4GSB

Oil Shale  (137)  Apr 75
    NTIS/PS-75/362/4GSB

-------
 Public Opinion and Sociology of Water
     Resource  Development (82) 1970-
     Apr 75
     NTIS/PS-75/373/1GSB
 Planning and Impact of Water Resource
     Programs (210) 1972-Apr75
     NTIS/PS-75/374/9GSB
 Biochemical  Oxygen Demand (262) Mar
     75
     NTIS/PS-75/375/6GSB
 Geothermal Energy (148) Apr 75
     NTIS/PS-75/377/2GSB
 Underwater  Construction  and  Mining
     (127)  May 75
     NTIS/PS-75/392/1GSB
 Effects of Land Use and Urbanization on
     Water Resources (94)  1971-May 75
     NTIS/PS-75/401/OGSB
 Salt Marshes (92)  May 75
     NTIS/PS-75/426/7GSB
 Water Quality   Modeling—Hydrological
     and   Limnological  Systems (213)
     Jun 75
     NTIS/PS-75/441/6GSB

 Sport Fishing (150) Jun 75
     NTIS/PS-75/468/9GSB
 Forest Management (85) Jun 75
     NTIS/P S-75/483/ 8GS B

 Eutrophication. Vol 1.  1964-1973 (194)
    Jun 75
     NTIS/PS-75/522/3GSB
 Eutrophication.  Vol 2.  1974-June 1975
     (86) Jun  75
     NTIS/PS-75/523/1GSB

 Offshore Drilling (116) Jun 75 Includes
    environmental  impacts
    NTIS/PS-75/540/5GSB
 Flood Control (258) 1972-Jun 75
    NTIS/PS-75/552/OGSB
 Water  Rights and  Water  Law.  Vol 2.
    1974-1975 (99) July 75
    NTIS/PS-75/558/7GSB
 Water  Rights and  Water  Law.  Vol 1.
    1964-1973 (122) July 75
    NTIS/PS-75/559/5GSB

 Mine Safety.  Part  1.  Fires and  Explo-
    sions  (81) Jun 75
    NTIS/PS-75/562/9GSB
 Mine Safety. Part 2. Communication and
    Position Finding Systems (53) June
    1975
    NTIS/PS-75/563/7GSB

 Mine  Safety.  Part   3.   Occupational
    Health-General  Studies (110) Jun
    75
    NTIS/PS-7S/564/5GSB
Mine  Safety.  Part   4.   Occupational
    Health-Radioactivity (49) Jun 75
    NTIS/PS-75/565/2GSB
Mine Safety.  Part  5. General  Studies
    (121) Jun 75 Excludes fire  safety,
    communication systems,  and health
    studies
    NTIS/P S-75/ 566/OGS B

Coal Beneficiation  (71)  Jul 75
    NTIS/PS-75/593/4GSB
Urban Storm  Sewers and Water Runoff.
    Vol 2. 1974-Jun 1975. (105) Jul 75
    NTIS/ PS-75/ 602/3GS B
 Urban Storm Sewers and Water Runoff.
    Vol 1. 1964-1973 (177) Jul 75
    NTIS/PS-75/603/1GSB

 Automatic  Acquisition of Water Quality
    Data (140)  1970-Jul 75
    NTIS/PS-75/639/5GSB

 Agricultural  Resources  Surveys (81)
    Aug 75
    NTIS/PS-75/668/4GSB
 Network  Flows (138) Sep  75 Includes
    Applied Studies
    NTIS/PS-75/694/OGSB
 Water Quality Management in Estuaries
    and Coastal  Zones (214) Sep 75
    Excludes  specific  biological  and
    oceanographic studies
    NTIS/PS-75/698/1GSB

 Acid Mine Drainage (150) Sep 75
    NTIS/PS-75/714/6GSB
 Snow Studies (252) Sep 75
    NTIS/PS-75/719/5GSB

 Weather   Modification   Effects   and
    Management (117) Sep     75 Ex-
    cludes theory and physics of cloud
    seeding and nucleation
    NTIS/PS-7S/722/9GSB
 Mohole Project. Part 1. Drilling Platform
    (153) Sep 75
    NTIS/PS-75/724/5GSB

 Mohole Project. Part 2. Drilling Section
    (269) Sep 75
    NTIS/PS-75/725/2GSB
 Mohole Project. Part 3. Positioning and
    Reentry Systems  (86) Sep 75
    NTIS/PS-75/726/OGSB

 Mohole Project. Part 4. General Studies
    (132) Sep 75
    NTIS/PS-75/727/8GSB
 Water  Resources in Arid and Semiarid
    Regions (68) Sep 75
    NTIS/PS-75/737/7GSB

 Ground Water Pollution.  Part 1. General
    Studies  (193) Sep 75 Excludes stu-
    dies dealing with irrigation and fer-
    tilization
    NTIS/PS-75/739/3GSB
 Ground Water Pollution.  Part 2. Pollu-
    tion From Irrigation and Fertilization
    (178) Sep 75
    NTIS/PS-75/740/1GSB
 Ground Water Pollution. Part 3. Saline
    Ground Water (90) Sep 75
    NTIS/PS-75/741/9GSB

 Strip Mining (145) Oct 75
    NTIS/PS-75/751/8GSB
 Environmental and  Ecological Effects of
    Dredging (136) Oct 75
    NTIS/PS-75/7S5/9GSB

 Seismology (180) 1974-Oct      75 Ex-
    cludes  underground explosion de-
    tection
    NTIS/PS-75/769/ OGSB
Range  Finders (114) Nov 75
    NTIS/PS-75/812/8GSB

Development of  Forest Industries (109)
    Nov 75
    NTIS/PS-75/827/6GSB
Magnetometers  (162) Nov  75 Includes
    only equipment studies
    NTI S/PS-75/830/OGSB
  Sediment  Transport in Rivers (85)  Nov
     75
     NTIS/PS-75/848/2GSB
  Paleoclimatology (66)  Nov 75
     NTIS/PS-75/851/6GSB

  Paleomagnetism  (97) Nov 75
     NTIS/PS-75/852/4GSB
  Forest Watersheds (91) Nov 75
     NTIS/PS-7S/856/SGSB

  Reservoir and Lake Sedimentation (105)
     Dec 75
     NTIS/PS-75/886/2GSB
 Sediment-Water Interactions  and Their
     Effects Upon  Water Quality (106)
     Jan 76 Excludes salt water studies
     NTIS/PS-76/0021 /6GSB

 Time Series Forecasting and Prediction
     (117) Jan 76  Includes studies  on
     hydrology,  meteorology,  manage-
     ment, and energy among others
     NTIS/PS-76/0031/5GSB

 Coal Mine Waste  (78) Feb 76
     NTIS/PS-76/OOS3/9GSB

 Instrumentation  and  Data  Processing
     Used   in  the  Earth  Resources
     Technology Satellite (157) 1974-Jan
     76
     NTIS/PS-76/0055/4GSB

 Biological  Productivity in  Fresh  Water
     Environments (140) Jan 76
     NTIS/PS-76/0056/2GSB

 Permafrost.  Part  1.  General Studies
    (113) Feb 76
    NTIS/PS-76/0069/5GSB

 Permafrost. Part 2. Structural  Engineer-
    ing (188) Feb 76
    NTIS/PS-76/0070/3GSB

 Permafrost Engineering (171) Feb  76
    
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Table I - Some Available Physical Data for the Higher Benzenepolycarboxylates
                         Solubility (g/IOOg solvent)
Hemimenitic
Acid
Henri nielli tic
Anhydride
Trimesic
Acid
Tri nielli tic
Acid
Trimellitic
Anhydride
Pyromellitic
Acid
Pyromellitic
Di anhydride
Mellitic
Acid
BP(°C) MP(°C)
190-197
(decomp)
197
375-380
(sub!)
216-218
390 168
257-265
(decomp)
397-400 287
286-288
(decomp)
Water Methanol (m)/Ethanol (e) Xylene CC14
__
—
0.24 (25°C) 8.0(m) (25°C) 0.01 (o-xylene) 0.01
2.1 (25°C) 25.3(e) (25°C) 0.006 0.004
(reacts) (reacts) 0.4 0.002
1 (20°C) 10(e) (10°C)
__
Sol. Sol.

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     These compounds are manufactured by oxidation of the polyrnethy I benzene
analogs using air, nitric acid, or chromic acid as the oxidizing  agent
(Towle ejt al_., 1968).   Of the higher benzenepolycarboxylates,  only
trimesic acid, trimellitic acid (and its anhydride),  and pyromellitic
acid (and its dianhydride) have known current commercial significance.
Because these compounds are produced by fewer than three companies, no
production figures may be reported by the International  Trade  Commission.
Table II lists the three commercially significant compounds.
     Trimellitic anhydride is used to prepare plasticizers,  alkyd
resins, unsaturated polyesters, printing inks, resin intermediates,
adhesives, molding resins and dyes.  The largest outlet is the preparation
of its triisooctyl and triisodecyl esters, which are used as specialty
plasticizers in vinyl  resins where permanency is required (as  in  wire
insulation, upholstery, refrigerator gasketing and thin fabric coatings).
Production of trimellitic acid esters has increased steadily from 0.88
million pounds in 1963 to 15.4 million pounds in 1973, the latter requiring
between 5.4 and 6 million pounds of TMAN.  Other major applications of
TMAN include the production of poly(amide-imide) resins for use in wire
enamels and electric-insulating varnishes; poly(ester-imide) formulations
used for wire enamels; and water-based alkyd resins used in the surface
coatings industry (Stanford Research Institute, 1971; 1972;  1974).
     Toward the end of the 1960's, trimesic acid was reported to  have
been under development for commercial use as a crosslinking agent for
polymers, and in the preparation of triester plasticizers (Towle  et al.,
1968).  However, in an oral communication with American Bio-Synthetics
Corporation  (1974), it was learned that the only current commercial use
of TMSA is as a crosslinking agent in solid propellant fuels.
     Pyromellitic dianhydride  (PMDA) is used as a crosslinking and
curing agent for epoxy resins which, in turn, are used for
                              -  8 -

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               Table II - Producers of the Commercially
              Significant Higher Benzenepolycarboxylates
  Product
          Producer
   Capacity*
(Million  of Pounds)
Trimesic Acid
American Bio-Synthetics Corp.
(Milwaukee, Wise.)
Trimellitic Anhydride    Amoco Chem.  Corp.
                         (Joliet, 111.)
                                        50  (in 1969)
Pyromellitic Acid
(and dianhydride)
1. E.I. DuPont de Nemours & Co.
   Inc., Indust.  Chem. Dept.
   (Gibbstown, N. J.)
  3-4  (in  1971)
                         2. Princeton Chem.  Research Inc.
                            (Princeton, N.  J.)
                                        0.4  (in  1965)
     *Stanford Research Institute, 1971

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protective surface coatings, adhesives and a number of other applications.
Combined with aromatic diamines, PMDA is used to produce polyimides of
excellent high-temperature resistance.  PMDA-based polyimides are
specialty resins used in such applications as electrical sheet and film
insulation, laminates, electrical wire coatings, and varnishes, diamond
abrasive wheels, precision parts, and for various aerospace applications
(Stanford Research Institute, 1971).   Pyromellitic acid is described in
a patent as.the active ingredient in  dental plaque-inhibiting mouthwash,
toothpaste and toothpowder preparations (Felger, Gillette Co., 1972).
The patent office of the Gillette Company reported that the PMDA
dentifrice preparation is still  a "paper patent", j_. e_.s there is no
commercial use of these products, but that the National Institute of
Dental Research has expressed interest in testing PMDA in its anti-
plaque/anti-caries drug investigations (Anderson, 1975).
     In a patent for a nitrogen- and  phosphorus-free detergent for-
mulation, hexasodium benzenehexacarboxylate and pentasodium benzene-
pentacarboxylate are named as the primary detergent builders, with the
sodium salts of tri- and tetracarboxylates as additional builders
(Benjamin and Sayler, Procter and Gamble, 1973).  A second patent,
although naming only tetrasodium benzenetetracarboxylate as the deter-
gent builder, describes a typical composition which includes as a
builder at least one C, ~ aliphatic or aromatic carboxylate or anhy-
dride, or its ammonium or alkali metal salt at a concentration of 2
percent by weight (Hentschell and Hentschell, 1973).
     While the proposed use of the higher benzenepolycarboxylates as
detergent builders was instrumental in initiating this environmental
hazard assessment, a recent oral communication with a Procter and Gamble
representative (Hall, 1975) disclosed that benzenepentacarboxylate and
benzenehexacarboxylate, while found to be satisfactorily biodegradable,
were not adequate as detergent builders.  There has been no attempt
to market the benzenepolycarboxylates as detergent builders to date
by Procter and Gamble, or, as far as  can be determined, by any
other detergent formulator.
                           - 10 -

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II.  ENVIRONMENTAL ASPECTS

     No monitoring data or background level measurements are known
to exist for these compounds.   While no analytical  method specifi-
cally designed for detection of the higher benzenepolycarboxylates
in the environment has been reported in the literature, Schnitzer
and others working with humic substances have made extensive use
of gas chromatography to identify benzenepolycarboxylates (usually
as the more volatile methyl esters) in degraded humic and fulvic
acids (Schnitzer and Khan, 1972).  The method should be adaptable
for detecting benzenepolycarboxylates in other environmental
samples.
     To date, the higher benzenepolycarboxylates have not been
identified or implicated as environmental contaminants. No inci-
dents of losses to the environment from their manufacture, trans-
port, or use in the production of other substances have been
reported.
     As is the case for many chemical intermediates, entry into
the environment via decomposition of the end products is possible;
however, there are no reports describing such an occurrence
regarding the higher benzenepolycarboxylates.
     It does not appear that the higher benzenepolycarboxylates
occur naturally as the acids.   However, the chemical nature of
humic substances (the bulk of the organic matter in soil and
water) is currently viewed as being composed of benzenepolycar-
boxylic and phenolic acids held together by hydrogen bonds to form
a stable polymeric structure.   Weakening of these bonds will break
the structure and release the component parts.  All of the ben-
zenepolycarboxylates have been identified as products of humic
substances from various soils treated with permanganate, nitric
acid, or by a non-degradative method involving methylation with
diazomethane (Schnitzer and Khan, 1972).  The extent to which the

                               - 11 -

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benzenepolycarboxylates occur in humic substances as the "free"  acids is
not known, but is thought to be exceedingly small (Schnitzer,  1975).
     According to Poole (1975), benzenepentacarboxylate and benzene-
hexacarboxylate were found to be quite biodegradable using a 26-day
carbon dioxide production test (see Sturm,  1973)  and a BOD test. While
degradation appears probable, and incorporation into humic substances
possible, the mobility and ultimate fate of higher benzenepolycarboxylates
in the environment is not adequately understood.
     There are no known standards, regulations or guidelines to  control
the higher benzenecarboxylates.
                               -  12  -

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III.  BIOLOGICAL ASPECTS

     1.   Toxicity
     The only toxicity data encountered in the literature dealt with  the
acute toxicity of trimellitic acid and the corresponding anhydride.   The
oral LDgQ of TMA was determined to be 1.25 g/kg in mice and 1.90 g/kg in
rats, while TMAN was found to have an ID™ of 2.50 g/kg in mice and 6.25
g/kg in rats.  In both rats and mice, oral administration of TMA and
TMAN elicited the same basic symptoms:  swelling of internal organs and
skin, and respiratory depression.   Inhaled TMA seems primarily to attack
the mucous membranes, causing signs of respiratory distress (Batyrova
and Uzhdavini, 1970).
     The LD50 values for TMA and TMAN reported above indicate that they
are at most only moderately toxic under conditions of acute exposure  and
that the levels necessary to cause acute adverse effects are, for these
two compounds, environmentally unrealistic.  No chronic toxicity studies,
studies of carcinogenicity, mutagenicity, etc., were found, nor was  any
information found dealing with aquatic toxicity, phytotoxicity or toxicity
to microorganisms.
     2.  Metabolic Effects, In vitro
     Gawron and Birckbichler (1971) found that trimesic acid, trimellitic
acid and pyromellitic acid competitively inhibit the enzyme cis-aconitase,
isolated from pig heart.  Table III shows percentages inhibition for
these compounds and for three benzenedicarboxylates.  cis-Aconitase  is
an enzyme which converts citrate to isocitrate in the Krebs cycle.  The
Krebs cycle is the biochemical pathway present in animal and plant cell
mitochondria through which fragments of organic compounds, available
from various metabolic reactions involving the degradation of proteins,
fats and carbohydrates, can be effectively utilized to obtain and
                               - 13 -

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                         TABLE III.

               Inhibition of cis-Aconitase by
          Various Benzenepolycarboxylic Acids at mM

    Acid                                          % Inhibition

Terephthalic                                           0

Isophthalic                                            3

Phthalic                                               5

Trimesic                                              20

Trimellitic                                           33

Pyromellitic                                          51
                              -14-

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store chemical potential  energy.   Interference with the Krebs cycle is,
therefore, a serious threat to the organism.   Demonstration of in vitro
inhibition, as described above, does not imply that these compounds will
interfere with the Krebs cycle in vivo, where absorption, metabolism,
transport to the mitochondria and other factors need to be considered.
At the same time, the information does indicate a potential for this
metabolic effect to occur in whole plants and/or animals.
                                -  15  -

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                              REFERENCES
Anderson, Wm. (1975), Patent attorney for Gillette Co.,  oral
     communication.

Batyrova, T. F.  and E.  R.  Uzhdavini  (1970),  "Toxicology  of Trimel-
     litic Acid and Trimellitic Anhydride,"  Tr.  Nauch.-Issled.
     Inst. Neftekhiem,  Proizvod., 2^ 14S •

Benjamin, L. and J. H.  Saylor (1973), (Procter and Gamble Co.)
     Brit. Patent 1,317,076; U.S. Appl.  98,122 (1970).

Felger, C. B. (1972), (Gillette Co.) U.S. Patent 3,671,626-

Gawron, 0. and P. J. Birckbichler (1971), "1,2,3-DL-Tricarboxy-
     cyclopentene-1 and Other Inhibitors of  Cis-Aconitase," Arch.
     Bioch. Biophys., 147(2), 772 .

Hall, R. E. (1975), Associate Director of Product Development of
     Packaged Soap and Detergents Division,  Procter and  Gamble
     Co., oral communication.

Hentschell, U. S. E. and G. 0. Hentschell (1973), Brit.  Patent
     1,309,814 .

Howard, P. and P. Durkin (1973) "Preliminary Environmental Hazard
     Assessment of Chlorinated Naphthalenes, Silicones,  Fluoro-
     carbons, Benzenepolycarboxylates and Chlorophenols", NTIS  No.
     PB-238 074/AS.

Leithe, W. (1973), "The Analysis of Organic  Pollutants in Water
     and Waste Water,"  Ann Arbor Science Publishers, Inc., Ann  Arbor,
     Mich., pg.  4 •

Poole, R.  (1975), Product Development of Packaged Soap and Deter-
     gents Division, Procter and Gamble Co., oral communication.

Schnitzer, M. (1975), private communication.

Schnitzer, M. and S. U. Khan (1972), Humic Substances in the
     Environment, Marcel Dekker, Inc., New York.

Stanford Research Institute (1971), "Polyimide Resins",  Chemical
     Economics Handbook, 580.1402 A, B, F, G, J, M, 0.

Stanford Research Institute (1972), "Alkyd Surface Coatings",
     Chemical Economics Handbook, 592,5822 D .
                              - 16 -

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Stanford Research Institute (1974), "Plasticizers", Chemical
     Economics Handbook, 579.5022 H.

Sturm, R. N. (1973), "Biodegradability of Non-Ionic Surfactants:
     Screening Test for Predicting Rate and Ultimate Biodegrada-
     tion", Journ. Amer. Oil Chem. Soc., 50_(5):  159-167.

Towle, P. H., R. H. Baldwin, and D. H. Meyer (1968) "Phthalic
     Acids and other Benzenepolycarboxylic Acids", in Encyclo-
     pedia of Chemical Technology, A. Stauden (Ed.) (John Wiley
     & Sons, New York, Second Edit.) Vol. 15, 444-487.
                               - 17 -

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                                   TECHNICAL REPORT DATA
                            (Please rend Instructions on the reverse before completing)
1. REPORT NO.

     EPA-560/8-75-002
                              2.
4. TITLE AND SUBTITLE
      ENVIRONMENTAL HAZARD ASSESSMENT REPORT
      Higher Benzenepolycarboxylates
           Frank j_

           Office of Toxic Substances
           II -S-  Fnvirnnmpntal Prntpr-Hrm
                                           gency
                                                            3. RECIPIENT'S ACCESSIor»NO.
                5. REPORT DATE

                    November 1975	
                6. PERFORMING ORGANIZATION COC.H
                                                           8. PERFORMING ORGANIZATION HtPORT NO.
9. PERFORMING ORGANIZATION NAME AND ADDRESS

     Office  of Toxic Substances
     U.S.  Environmental Protection  Agency
     401  "M"  Street, S. W.
     Washington,  D.C	2Q4fiQ	
                                                            10. PROGRAM ELEMENT NO.
                    2LA328
                 11. CONTRACT/GRANT NO.
12. SPONSORING AGENCY NAME AND ADDRESS
                                                            13. TYPE OF REPORT AND PERIOD COVERED
                                                               Final	
                                                            14. SPONSORING AGENCY CODE
15. SUPPLEMENTARY NOTES
16. ABSTRACT
           This  report is an analysis  of available information on the higher
           benzenepolycarboxylates  (i.e., benzenecarboxylates through benzerie-
           hexacarboxylate) pertinent  to an assessment  of  the potential environ-
           mental  hazard posed by these compounds.  Aspects discussed are  produc-
           tion  and uses of the subject compounds, environmental aspects and
           biological  aspects.  The  study concludes that current uses of these
           compounds do not present  an environmental hazard, but makes recommendations
           for additional studies to be undertaken prior to initiation of  new and
           potentially dispersive uses.
 7.
                                KEY WORDS AND DOCUMENT ANALYSIS
                  DESCRIPTORS
           Carboxylic  acids
           Environment
           Pollution
           Toxicity
           Toxicology
           Evaluation
ie. ui-.;i HIBUTSON STATEMENT
           Release unlimited
                                              b.lDENTIFIERS/OPEN ENDED TERMS
     Benzenepolycarboxylates
     Benzenepolycarboxylic
     acids
     Environmental exposure
                                              19. SECURITY CLASS (This Report)
                                                Unclassified
   20. SECURITY CLASS (This page.)

     Unclassified
c. COSATI I'icld/Group


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 07/C
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