Terephthalic Acid

log Kow = 2.00

2.00

1.96

1.68

1.51 (NTP, 1992) - Denser than water; will sink

Specific gravity = 1.522 at 25 °C

Relative density (water = 1): 1.51

1.51

1.51 @25 °C

Needles

White crystals or powder

Insoluble (NTP, 1992)

Insoluble in chloroform, ether, acetic acid; slightly soluble in alcohol; soluble in alkalies

Solubilities at 25 °C (g/100 g solvent): water = 0.0017, glacial acetic acid = 0.013, methanol = 0.1, dimethylformamide = 6.7, dimethyl sulfoxide = 19.0

In water, 15 mg/L at 20 °C

0.015 mg/mL at 20 °C

Solubility in water, g/100ml at 20 °C: 0.28

260 °C

500 °F (260 °C) (Open cup)

260 °C

greater than 572 °F at 760 mmHg (sublimes without melting) (NTP, 1992)

>572 °F (sublimes)

Sublimes (NTP, 1992)

427 °C (sealed tube)

> 300 °C

sublimes

0.0000092 [mmHg]

Vapor pressure: 1.3 kPa at 303 °C; 13.3 kPa at 353 °C; 26.7 kPa at 370 °C; 53.3 kPa at 387 °C; 101.3 kPa at 404 °C

Vapor pressure = 0.097 kPa at 250 °C

6X10-11 mm Hg at 25 °C /Antoine extrapolation from higher temperatures/

Vapor pressure, Pa at 20 °C:

FCS -> FDA Cumulative Estimated Daily Intake (CEDI)

FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

This chemical does not meet GHS hazard criteria for 82.5% (1040 of 1260) of all reports.

Warning

H315 (17.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1260 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

Chemical: 1,4-Benzenedicarboxylic acid

Regulation (EC) No 1935/2004 (amended)

1,4-Benzenedicarboxylic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenedicarboxylic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 15-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15563

Terephthalic acid: Does not have an individual approval but may be used under an appropriate group standard

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

Combustible. Finely dispersed particles form explosive mixtures in air.

Practically nontoxic in acute, high-dose animal studies; In high-dose feeding studies in rats, it causes bladder stones and subsequent bladder cancers; The bladder cancers are thought to be secondary to the presence of bladder stones. [ACGIH] A skin and eye irritant; [ICSC] An irritant; Effects in high-dose animal studies include abnormal liver function tests; [MSDSonline]

DOE/ORNL; Support for Establishing Structure-Activity Relationships Between a Series of Phthalate Esters and Toxicity to Aquatic Organisms. Report No. ORNL/TM-9254 Contract No# AC05-84OR21400 (1985)

PIERCE ET AL, PHTHALATE ESTERS IN THE AQUATIC ENVIRONMENT, NATL RES COUNC CAN ASSOC COMM SCI CRITER ENVIRON QUAL PUBL 0 (17583): 1 (1980). THE PHYSICAL-CHEMICAL PROPERTIES, ANALYTICAL DETERMINATION & ENVIRONMENTAL DYNAMICS OF PHTHALATE ESTERS (INDUSTRIAL PLASTICIZERS) ARE REVIEWED. ARTICLE INCLUDES DIBUTYL PHTHALATE.

USEPA; Ambient Water Quality Criteria Doc: Phthalate Esters (1980) EPA 440/5-80-067

USEPA/ECAO; Phthalate Atlas Report (1980)

Nat'l Research Council Canada; Phthalate Esters (1980) NRCC No.17583

TEREPHTHALIC ACID is a carboxylic acid. It donates hydrogen ions if a base is present to accept them. This "neutralization" generates substantial amounts of heat and produces water plus a salt. Insoluble in water but even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. May react with cyanide salts to generate gaseous hydrogen cyanide. Will react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by reaction with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. React with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. May initiate polymerization reactions; may catalyze (increase the rate of) chemical reactions.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Terephthalic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

After material has been contained, scoop up contaminated soil and place in impervious containers. Material may be /disposed of/ in an approved chemical incinerator. If facilities are not available, material may be /disposed of in/ an approved waste chemical landfill. When dilute, amenable to biological treatment at a municipal sewage treatment plant.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

INCR EFFECTIVENESS OF CERTAIN ANTIBIOTICS SUCH AS CHLORTETRACYCLINE.

... Chlorothiacide or dietary bicarbonate abolished terephthalic acid-induced urolithiasis in /male weanling Fisher 344 rats fed 4.0% terephthalic acid in diet for 2 weeks (postnatal days 28-42)/.

(14)C-labeled terephthalic acid may be both secreted and reabsorbed by the nephron, and when infused at 3 or 6 umol/min its excretion efficiency is comparable to that of p-aminohippuric acid and tetraethylammonium. Probenecid significantly inhibited the excretion of (14)C-labeled terephthalic acid. M-Hydroxybenzoic acid significantly decreased the excretion of (14)C-labeled terephthalic acid but was without any significant effect on the excretion of p-aminohippuric acid.

The joint injury actions and mechanisms of terephthalic acid (TPA), ethylene glycol (EG) and/or Dowtherm A (DOW): [SRP: a mixture of biphenyl and biphenyl oxide] on liver in rats were investigated. A subchronic toxicity study was designed by a 2(3) factorial method. Some enzymes, biochemical and morphologic indices reflecting the injury of liver were studied. The results showed that serum ALT and serum total bile acid (TBA) of rats in the combined intoxication groups were significantly higher than those in the groups with single toxic agent and control group. The results of factorial analysis showed that the joint action induced by TPA, EG and/or DOW were characterized as additive (TPA + EG), synergistic (EG + DOW), synergistic (TPA + DOW) and additive(TPA + EG + DOW) actions. The deduction was identified by morphologic observations.

To study injury of liver and kidney among the workers exposed to terephthalic acid(TPA), ethylene glycol(EG) and(or) dowtherm A(DOW), and research for early biological monitoring indexes. By using the method of occupational epidemiology, an investigation of industrial hygiene in a chemical fibre corporation was carried out and the changes of the liver and kidney functions were analyzed among the workers who had been exposed to TPA, EG, DOW.The values of serum gamma-glutamyl traspetidase(GGT) and total bile acid(TBA) in TPA + EG + DOW group men were (35.45 +/- 16.09) U/L, (10.29 +/- 6.76) umol/L respectively and the values of serum alanine transaminase(ALT) and TBA in TPA + EG + DOW group women were(30.68 +/- 8.58) U/L, (9.53 +/- 6.63) umol/L respectively, significantly higher than those in TPA, DOW and control groups(P < 0.05, P < 0.01). Compared with TPA, DOW and control groups, the values of urine N-acetyl-beta-D-glucosaminidase (NAG) and beta 2-2-microglobulim (beta 2-MG) in TPA + EG + DOW group of both men and women increased significantly(P < 0.05, P < 0.01), with (5.68 +/- 4.01) U/mmol Cr and (23.49 +/- 13.44) mg/mol Cr, and(6.68 +/- 4.68) U/mmol Cr and (22.80 +/- 13.00) mg/mol Cr, respectively. Analysis of regression indicated that both liver and renal injuries of the workers were evidently correlated with their exposure to TPA, EG and DOW after adjustment for the confounding factors such as sex, smoking, drinking, etc(P < 0.001). Based on available knowledge, it is reasonable to assume that the joint actions should be considered on the injury of liver and kidney caused by TPA, EG and(or) DOW among the workers. Serum ALT, GGT, TBA, urine NAG and beta 2-MG should be suggested as biomarkers for liver and kidney damage.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 79(SRC), determined from a structure estimation method(2), indicates that terephthalic acid is expected to have high mobility in soil(SRC). The pKa1 and pKa2 of terephthalic acid are 3.54 and 4.46 at 25 °C(3), respectively, indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of terephthalic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Terephthalic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 6X10-11 mm Hg at 25 °C(3). Terephthalic acid, present at 100 mg/L, reached 74.7% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test which classifies the compound as readily biodegradable(5). Terephthalic acid was determined to be biodegradable using the following biodegradation screening tests: Coupled Units (93% DOC, 1-day), Zahn-Wellens (93% DOC,4-days), Sturm Test (72% CO2 evolution, 28 days), Modified OECD Test (82% DOC, 19-day surface water die-away) and Closed Bottle Test (112% BODT, 30 days)(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 79(SRC), determined from a structure estimation method(2), indicates that terephthalic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.9X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of 2.00(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Terephthalic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Terephthalic acid, present at 100 mg/L, reached 74.7% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test which classifies the compound as readily biodegradable(6). Terephthalic acid was determined to be biodegradable using the following biodegradation screening tests: Coupled Units (93% DOC, 1-day), Zahn-Wellens (93% DOC,4-days), Sturm Test (72% CO2 evolution, 28 days), Modified OECD Test (82% DOC, 19-day surface water die-away) and Closed Bottle Test (112% BODT, 30 days)(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), terephthalic acid, which has an extrapolated vapor pressure of 6X10-11 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere; however, one monitoring study has reported its detection in the gas-phase(3). Terephthalic acid absorbs UV light at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).

/AQUATIC SPECIES/ The biodegradation and toxicity of the purified terephthalic acid (PTA) processing wastewater was researched ...The results of bioassay ...and calculation with software Ebis3 showed that the 48hr-LC50 (median lethal concentration) to Daphnia magna for the PTA concentration in the wastewater was only 1/10 of that for the chemical PTA. There were 5 kinds of benzoate pollutants and their toxicities existing in the wastewater at least. The toxicity parameter value of the pure chemical PTA cannot be used to predicate the PTA wastewater toxicity...

/OTHER TERRESTRIAL SPECIES/ By using model Caenorhabditis elegans, the toxicity of purified terephthalic acid (PTA) wastewater was evaluated through a battery of biotest, including life span, days of 50% lethal, generation time, brood size, head thrashes, and body bends. The results revealed that compared with control, the life span and generation time of C. elegans exposed to 660 mg PTA/L were delayed to some degree, and its head thrashes and body bends were inhibited. The procreation function of C. elegans exposed to PTA wastewater was greatly affected, with the brood size being as low as 25% of the normal one. The most sensitive indicator, brood size of C. elegans, might be a potential indicator in evaluating PTA wastewater toxicity.

/PLANTS/ Toxicity of products from polyester hydrolysis such as succinic acid (SA), adipic acid (AA), mandelic acid (MA), terephthalic acid (TA), 1,4-butanediol (1,4-B), ethylene glycol (EG), styrene glycol (SG) and 1,4-cyclohexane dimethanol (1,4-C) was evaluated by phytotoxicity test on germination of young radish seeds ...The phytotoxicity test revealed SG > MA > 1,4-C > AA approximately SA > TA approximately EG > 1,4-B in order of decreasing toxicity taking into consideration the growth behavior after germination as well as the percentage of germination...Tests for the phytotoxicity ...indicated that the aromatic compounds were more harmful than the aliphatic ones...

Cough.

Redness.

Redness.

Terephthalic acid was detected at a concentration of 5.3 ppb in the effluent of night soil treatment plant in Japan(1). The concentration of terephthalic acid in the waste water from a dimethyl terephthalate manufacturing plant was 459 mg/L(2).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of terephthalic acid can be estimated to be 79(SRC). According to a classification scheme(2), this estimated Koc value suggests that terephthalic acid is expected to have high mobility in soil. The pKa1 and pKa2 of terephthalic acid are 3.54 and 4.46 at 25 °C(3), respectively, indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

Chronic toxicity and oncogenicity were evaluated in groups of male and female Fischer 344 rats (total: 504/sex) ingesting terephthalic acid via the basal diet at nominal doses of 20, 142 and 1000 mg/kg/day for 2 years beginning at age seven weeks. Female rat survival was greater for control groups compared to treatment groups, but a dose-response relationship was not evident. Body weights and food consumption values were lower for high dose males for the duration of the study, with decreased lung, heart, liver and kidney weights at study termination. At six and twelve month sacrifice, relative liver weights were greater for high dose females. At termination, high and mid dose females had decreased heart and kidney weights and increased relative brain weights. Urinalyses, hematology and clinical chemistry evaluations revealed some statistical differences, but a dose-response relationship was not evident. Terephthalic acid induced bladder stones in high dose females, and histopathology of the bladder revealed microconcretions or calculi. The incidence of bladder tumors in high dose females was 19/118. The incidence of squamous metaplasia in the bladder of high dose females was 11/118. Both control and treatment groups had a high incidence of eye lesions, cataracts and uterine adenocarcinomas.

A one-generation reproduction study was conducted in tandem with a 90-day subchronic toxicity study which evaluated the effects on rats of dietary exposure to terephthalic acid (TA). Male and female Wistar and CD rats (number of animals/group not reported) were exposed to TA in the diet at dose levels of 0, 0.03, 0.125, 0.5, 2.0 or 5% at which time 10 breeding pairs from each dietary level were kept on their respective diet throughout mating, gestation, lactation and postweaning periods. There were significant differences observed between treated and control animals in the following: increased mortality of fetuses and neonates (76% of 17 Wistar pups and 96% of 23 CD pups found dead at birth (Day 0) were from groups of parents ingesting 2 and 5% TA), reduction of newborn viability (50% reduction of highest-dose level Wistar male newborns), decreased survivability (50% reduction for male and female CD pups from highest-dose group), decreased body weights (highest-dose level Wistar pups at Days 1 and 21, and highest-dose level CD pups at Day 21), increased unscheduled deaths of F1 weanling rats (prior to scheduled Day 51 sacrifice; confined to highest-dose groups of both strains of rats, associated with high incidence of renal and bladder calculi), and increased incidence of renal and bladder stones (high-dose level, both strains). There were no significant differences observed between treated and control animals in the following: fertility index, and litter size. Other findings observed at necropsy of the pups from treated groups included enlarged ceacum, enlarged or distended ureter, enlarged kidneys, and bladder wall thickening. There were no differences in the sensitivity of the two strains of rats to the oral exposure to TA. Full experimental details and results, or statistical treatments were not reported.

Terephthalic acid (CAS # 100-21-0) was evaluated for reproductive toxicity. The test substance was administered in the diets of adult male and female Wistar and CD rats for 90 days at concentrations of 0% (0 mg/kg/day), 0.03% (18 mg/kg/day), 0.125% (75 mg/kg/day), 0.5% (300 mg/kg/day), 2.0% (1200 mg/kg/day) or 5.0% (3000 mg/kg/day). The number of rats per group was not reported. At 2.0 and 5.0%, toxic effects included reductions in food consumption, body weight, and body weight gain, with CD rats being more sensitive to the test substance. At 5% concentration level, five deaths occurred. On Day 91, 10 male and 10 female rats of each strain from each group were bred and maintained on terephthalic acid diets. There were no treatment-related effects on reproduction or fertility. However, at 2.0 and 5.0% dietary concentration caused lethal effects on newborn and young rats. At 5%, reductions in Day 1 newborn body weights and 21-day survival were noted; and at Day 51 there was an increased incidence of renal and bladder calculi. There were no consistent strain difference.

Terephthalic acid (CAS # 100-21-0) was evaluated for reproductive toxicity. The test substance was administered as a particulate aerosol by inhalation at concentrations of 0, 1.0, 5.0, and 10.0 mg/m3 to four groups of 26 to 27 timed-pregnant primiparous Sprague-Dawley rats. The rats were exposed 6 hrs/day, 7 days/wk on gestation days 6 through 15 for a total of 10 consecutive days. No deaths occurred during the study. Clinical signs at all concentrations, included salivation, scaly tail, and red material around the nose/eyes/face. No significant differences in mean dam body or uterus weights, litter weights or dam body weight gain were evident. No pathological conditions were noted upon gross necropsy, although visible uterine implants were noted in all treatment groups. Embryo-fetotoxicity observations included similar numbers of resorptions in all treatment groups and at 5.0%, skeletal rib anomalies were significantly increased. There were no other significant differences in pup viability or fetal malformations.

A one-generation reproduction study was conducted in tandem with a 90-day subchronic toxicity study which evaluated the effects on rats of dietary exposure to terephthalic acid (TA). Male and female Wistar and CD rats (number of animals/group not reported) were exposed to TA in the diet at dose levels of 0, 0.03, 0.125, 0.5, 2.0 or 5% at which time 10 breeding pairs from each dietary level were kept on their respective diet throughout mating, gestation, lactation and postweaning periods. There were significant differences observed between treated and control animals in the following: increased mortality of fetuses and neonates (76% of 17 Wistar pups and 96% of 23 CD pups found dead at birth (Day 0) were from groups of parents ingesting 2 and 5% TA), reduction of newborn viability (50% reduction of highest-dose level Wistar male newborns), decreased survivability (50% reduction for male and female CD pups from highest-dose group), decreased body weights (highest-dose level Wistar pups at Days 1 and 21, and highest-dose level CD pups at Day 21), increased unscheduled deaths of F1 weanling rats (prior to scheduled Day 51 sacrifice; confined to highest-dose groups of both strains of rats, associated with high incidence of renal and bladder calculi), and increased incidence of renal and bladder stones (high-dose level, both strains). There were no significant differences observed between treated and control animals in the following: fertility index, and litter size. Other findings observed at necropsy of the pups from treated groups included enlarged ceacums, enlarged or distended ureters, enlarged kidneys, and bladder wall thickening.

URBAN/SUBURBAN: Terephthalic acid was qualitatively detected in the gas phase of urban air from Belgium(1). It was also qualitatively detected in the air particulate matter collected from Tokyo, Japan(2). Terephthalic acid was detected in atmospheric aerosol and in rainwater particle extracts from West Los Angeles, CA(3). Samples of urban aerosols over West Los Angeles, Downtown Los Angeles, Pasadena, Riverside, and San Nicholas Island (July-Dec) contained terephthalic acid at annual average concentrations of 1.3, 2.8, 1.5, 0.88, and less than 0.03 ng/cu m, respectively(4). The average atmospheric terephthalic acid concentration in the fine particulates collected at four urban sites in southern California (Sept 8-9, 1993 monitoring) was 5.4 ng/cu m with an overall range of 0.9 to 17.2 ng/cu m(5). Monitoring at 12 sites in southern CA in 1995, as part of the Southern California Children's Health Study, detected terephthalic acid particulate concentrations ranging from 0.256 to 0.7 ng/cu m(6).

RURAL/REMOTE: The average concns of terephthalic acid in the airborne aerosols from two relatively unpolluted mountainous regions of Japan were 11.1 ng/cu m and 3.9 ng/cu m(1). During 1995 air monitoring conducted at the Great Smoky Mountain National Park, TN, terephthalic acid was detected in 1 of 21 daytime samples at a concentration of 9 ng/cu m(1).

SOURCE DOMINATED: Terephthalic acid was detected at concentrations ranging from 20.8 to 99.6 ng/cu m in the particulates collected from a roadway tunnel in Hong Kong during Aug 2003 to Feb 2004 monitoring(1).

/HUMAN EXPOSURE STUDIES/ A 10 mL application of an oily paste containing 80% terephthalic acid to equal sites on the hand was not irritating. Also, a 24 hour application did not produce any signs of irritation or redness.

/SURVEILLANCE/ Forty-three workers exposed to terephthalic acid(TPA) were selected to study the dermal contamination of TPA and the load of TPA in urine. The results showed that there existed a double logarithmic correlation between dermal contamination of TPA and air TPA concentration and a logarithmic correlation between urinary TPA and total inhaled TPA. Neither dermal TPA contamination nor total TPA exposure exhibited a dose-dependent relationship with urinary TPA. Based on this occupational epidemiology investigation, it was proved that the absorption of TPA is not mainly from dermal exposure.

/ALTERNATIVE and IN VITRO TESTS/ Toxicity of products from polyester hydrolysis such as succinic acid (SA), adipic acid (AA), mandelic acid (MA), terephthalic acid (TA), 1,4-butanediol (1,4-B), ethylene glycol (EG), styrene glycol (SG) and 1,4-cyclohexane dimethanol (1,4-C) was evaluated ...by cytotoxicity test on HeLa cells...Toxicity on HeLa cells decreased /in order/ SG > 1,4-C > MA > TA > SA > AA > EG > 1,4-B. Tests for ...cytotoxicity indicated that the aromatic compounds were more harmful than the aliphatic ones...

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Terephthalic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

/The aim of this study was/ to investgate the metabolism of terephthalic acid (TPA) in rats and its mechanism. Metabolism was evaluated by incubating sodium terephthalate (NaTPA) with rat normal liver microsomes, or with microsomes pretreated by phenobarbital sodium, or with 3-methycholanthrene, or with diet control following a NADPH-generating system. The determination was performed by high performance liquid chromatography (HPLC), and the mutagenic activation was analyzed by umu tester strain Salmonella typhimurium NM2009. Expression of CYP4B1 mRNA was detected by RT-PCR. The amount of NaTPA (12.5-200 uL /per/ L) detected by HPLC did not decrease in microsomes induced by NADPH-generating system. Incubation of TPA (0.025-0.1 mmol /per/ L) with induced or noninduced liver microsomes in an NM2009 umu response system did not show any mutagenic activation. TPA exposure increased the expression of CYP4B 1 mRNA in rat liver, kidney, and bladder. Lack of metabolism of TPA in liver and negative genotoxic data from NM2009 study are consistent with other previous short-term tests...

... The concentrations of urine terephthalic acid(TPA) in rats after single oral administration in dose of 100 mg/kg bw were determined by high pressure liquid chromatography. ... The results showed that the first-order kinetics and two-compartment model were noted on the elimination of TPA. The main toxicokinetic parameters were as follows: Ka = 0.51/hr, half-life ka = 0.488 hr, half-life alpha = 2.446 hr, time to peak = 2.160 hr, Ku = 0.143/hr, half-life beta = 31.551 hr, Xu(max) = 10.00 mg. ...

The pharmacokinetics of (14)C labeled terephthalic acid were determined in Fischer 344 rats after iv and oral administration. After iv injection, the plasma concentration-time data were fitted using a 3-compartment pharmacokinetic model. The avg terminal half-life in rats was 1.2 hr and the average volume of distribution in the terminal phase was 1.3 L/kg.

(14)C-Terephthalic acid has a short elimination half-life (approximately 60-100 minutes) in the plasma; however, the apparent half-life was longer following administration by gavage.

A Rhodococcus species was isolated from soil by enriching for growth with dimethyl terephthalate as the sole carbon source. The organism degraded dimethyl terephthalate by hydrolysis of ester-bonds to free terephthalic acid which in turn was metabolized through protocatechuate by an ortho-cleavage pathway.

No evidence of metabolism of (14)C TPA was obtained by analysis of urine by high-performance liquid chromatography /following an iv dose to Fischer-344 rats/.

... The concentrations of urine terephthalic acid(TPA) in rats after single oral administration in dose of 100 mg/kg bw were determined by high pressure liquid chromatography. ... The results showed that the first-order kinetics and two-compartment model were noted on the elimination of TPA. ... The excretion rates of TPA in urine were about 50%, 52% and 53% in 0-24 hr, 0-48 hr and 0-72 hr respectively after administration. TPA is well absorbed when given orally and rapidly eliminated via urine. Urine TPA at the end of work shift should be considered as a biomarker of exposure for the occupational workers.

Terephthalic acid is absorbed from the gastrointestinal tract and is excreted in the urine apparently unchanged. Dermal or ocular absorption is negligible.

The pharmacokinetics of (14)C terephthalic acid were determined in Fischer-344 rats after iv and oral administration. After iv injection, the plasma concentration-time data were fitted with a three-compartment pharmacokinetic model. The average terminal half-life in 3 rats was 1.2 + or - 0.4 hr, and the average volume of distribution in the terminal phase was 1.3 + or - 0.3 l/kg. Following administration by gavage, a longer terminal half-life was obtained, indicating that dissolution of (14)C TPA or absorption from the gut may have been partially rate limiting. Recovery of (14)C TPA in the urine following a bolus iv dose was 101 + or - 8%, indicating essentially complete urinary excretion of the compound. No evidence of metabolism of (14)C TPA was obtained by analysis of urine by high-performance liquid chromatography. (14)C TPA was transported to the fetus after administration of the compound to pregnant rats; the concentrations in fetal tissues were low relative to the corresponding maternal tissues. Neonatal rats exposed to 5% TPA in the diet of their dams did not develop calculi until the onset of self-feeding. TPA was rapidly excreted into urine after administration to rats, and excretory mechanisms in the dam provided an effective mechanism of defense against TPA-induced urolithiasis in neonatal rats.

By use of the Sperber in vivo chicken preparation method, infusion of radiolabeled terephthalic acid ([14C]TPA) into the renal portal circulation revealed a first-pass excretion of the unchanged compound into the urine. This model was utilized further to characterize the excretory transport of [14C]TPA and provide information on the structural specificity in the secretion of dicarboxylic acids. At an infusion rate of 0.4 nmol/min. 60% of the [14C]TPA which reached the kidney was directly excreted. An infusion rate of 3 or 6 mumol/min resulted in complete removal of [14C]TPA by the kidney. These results indicate that TPA is both actively secreted and actively reabsorbed when infused at 0.4 nmol/min and that active reabsorption is saturated with the infusion of TPA at higher concentrations. The secretory process was saturated with the infusion of TPA at 40 mumol/mn. The excretory transport of TPA was inhibited by the infusion of probenecid, salicylate, and m-hydroxybenzoic acid, indicating that these organic acids share the same organic anion excretory transport process. m-Hydroxybenzoic acid did not alter the simultaneously measured excretory transport of p-aminohippuric acid (PAH), suggesting that there are different systems involved in the secretion of TPA and PAH. The structural specificity for renal secretion of dicarboxylic acids was revealed by the use of o-phthalic acid and m-phthalic acid as possible inhibitors of TPA secretion. m-Phthalate, but not o-phthalate, inhibited TPA excretory transport, indicating that there is some specificity in the renal secretion of carboxy-substituted benzoic acids. TPA was actively accumulated by rat and human cadaver renal cortical slices.

(14)C-Labeled terephthalic acid may be both secreted and reabsorbed by the nephron, and when infused at 3 or 6 umol/min its excretion efficiency is comparable to that of p-aminohippuric acid and tetraethylammonium.

Used in wool processing and making plastic films and sheets; Also added to poultry feeds and to certain antibiotics to increase their effectiveness; [HSDB]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry]

Terephthalic acid /is/ ... used almost exclusively to produce saturated polyesters.

Production of linear, crystalline polyester resins, fibers, and films by combination with glycols; reagent for alkali in wool; additive to poultry feeds.

Forms polyesters with glycols which are made into plastic films & sheets; /used/ in analytical chemistry.

Terephthalic acid is an intermediate in the production of oligomeric terephthalic acid esters.

TECHNICAL GRADE: MAXIMUM MOISTURE CONTENT 0.5 WT%; POLYMER GRADE SPECIFICATIONS: ASH, 15 PPM (MAX); TOTAL SIGNIFICANT METALS (MOLYBDINUM, CHROMIUM, NICKEL, COBALT, IRON, TIN, MAGNESIUM) 10 PPM (MAX); 4-FORMYLBENZOIC ACID, 25 PPM (MAX); MOISTURE, 0.5% (MAX)

(1973) 2.27-3.41X10+10 G

(1975) 4.5X10+10 G

(1982) 1.34X10+11 G /TEREPHTHALIC ACID AND DIMETHYL TEREPHTHALATE/

(1972) NEGLIGIBLE

(1975) 3.7X10+9 G (PRINCPL CUSTMS DISTS)

(1984) 8.06X10+7 G

2023: 5,500,000,000 - <7,000,000,000 lb

(1972) 3.63X10+10 G (FIBER GRADE)

(1975) 4.9X10+11 G

(1985) 3.26X10+7 g

(1990) 7.77 billion lb

For more U.S. Production (Complete) data for TEREPHTHALIC ACID (12 total), please visit the HSDB record page.

CHEM INT FOR POLYETHYLENE TEREPHTHALATE POLYESTERS, OF WHICH 93% IS USED IN POLYESTER FIBERS, AND 7% IS USED IN POLYESTER FILM (1973)

POLYESTER FILMS, 67%; PET FILMS AND PLASTICS, 23%; MISC, 3%; EXPORT, 7% (1982)

287X10+3 tons in the U.S. (1976)

1363X10+3 tons in the U.S. (1989)

p-Xylene is the feedstock for all terephthalic acid /production/. ... Oxidation catalysts and conditions have been developed which give nearly quantitative oxidation of the methyl groups, leaving the benzene ring virtually untouched. These catalysts are combinations of cobalt, manganese, and bromine, or cobalt with a co-oxidant, e.g., acetaldehyde [75-07-0]. Oxygen is the oxidant in all processes. Acetic acid [64-19-7] is the reaction solvent in all but one process. Given these constant factors, there is only one industrial oxidation process, with different variations, two separate purification processes, and one process which intermixes oxidation and esterification steps.

Produced commercially primarily by the Amoco process. Inhibition of the oxidation of the second methyl group of p-xylene is suppressed with the aid of added bromine-containing promoters as cocatalysts. ... The oxidation takes place in air and produces raw terephthalic acid, which is dissolved at high temperature under pressure in water, hydrated, and thus purified.

Prepared by oxidation of p-methylacetophenone.

(1) Oxidation of para-xylene or of mixed xylenes and other alkyl aromatics (phthalic anhydride); (2) reacting benzene and potassium carbonate over a cadmium catalyst.

Reacting carbon monoxide or methanol with toluene to form various intermediates which, upon oxidation, form terephthalic acid.

Grades: Commercial; fiber.

Technical grade: 98.5 wt%, min; polymer grade: >98.5 wt% polymer grade: >98.5 wt%

Specifications and typical analyses of purified terephthalic acid: [Table#2254]

Printing and Related Support Activities

1,4-Benzenedicarboxylic acid: ACTIVE

US Capacity = 3.2X10+6 tons/yr including dimethyl ester (1978)