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 -
-------
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-
-------
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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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
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(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-
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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-
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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
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NTIS/PS-75/176/8GSB
Biological Effects of Mercury Pollution
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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-
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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
-------
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.
-------
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 -
-------
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
-------
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.
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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
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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.
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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
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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
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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.
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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.
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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
06/F
07/C
21. NO. OF PACXS
22. PRiCE
Form 2220-1 (9-73)
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