Dimethylcyclohexan-1,4-dicarboxylat

Specific gravity: 1.102 at 35 °C/4 °C

Density: 1.095 - 1.097 g/cu cm at 30 °C

Partially crystalline solid

Clear colorless liquid

In water, 12,000 mg/L at 25 °C

Soluble in all proportions in most organic solvents

0.08 [mmHg]

0.00441 mm Hg at 25 °C /Extrapolated from data at higher temperatures/

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 38.3% (36 of 94) of reports.

Warning

H319 (61.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 94 reports by companies from 6 notifications to the ECHA C&L Inventory.

Warning

Chemical: 1,4-Cyclohexanedicarboxylic acid, dimethyl ester

1,4-Cyclohexanedicarboxylic acid, 1,4-dimethyl ester, trans- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Cyclohexanedicarboxylic acid, 1,4-dimethyl ester, trans- 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)

1,4-Cyclohexanedicarboxylic acid, 1,4-dimethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Cyclohexanedicarboxylic acid, 1,4-dimethyl ester 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)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 19-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/11660

In the days immediately following January 9, 2014, the West Virginia Poison Center received calls from over 1,900 patients reporting chemical exposures related to the drinking water. Most reported symptoms included mild rashes and reddened skin from dermal exposure, or GI distress (nausea, vomiting and/or diarrhea) from ingesting contaminated water. The symptoms tendeed to be mild and self-limiting.

On January 9, 2014, an estimated 10,000 gallons of an industrial chemical, 4-Methylcyclohexanemethanol (MCHM), spilled into the Elk River just upstream from the Kanawha County municipal water intake in Charleston, West Virginia. This municipal water system serves nearly 300,000 people whose water was affected by the chemical spill. Due to the uncertainty over the chemical levels in the water supply, the Office of the Governor issued a "Do Not Use" order at 6:00 pm on January 9, 2014. Later that evening, the West Virginia Department of Health and Human Resources contacted CDC about the release and requested assistance to review water sampling data and provide a drinking water screening level for MCHM. On January 21, 2014, the manufacturer reported that another material was part of the chemical release that occurred on January 9, 2014. This material has been identified as a proprietary mixture primarily composed of propylene glycol phenyl ether (PPH) and dipropylene glycol phenyl ether (DiPPH). It was in the same tank and entered the water system at the same time as the MCHM. This mixture represented a relatively small percentage (approximately 7.3% by weight) of the total amount in the tank.

Skin Irrit. 2 (100%)

Eye Irrit. 2 (61.7%)

Eye Irrit. 2A (100%)

Acute Eye Irritation/Corrosion: Not irritating to the eye.

Acute Dermal Irritation/Corrosion: Irritating

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.

LC50; Species: Daphnia magna (Water flea); Conditions: freshwater, static, 23-25 °C, pH 7.7-7.9, alkalinity 44 mg/L CaCO3, hardness 82 mg/L CaCO3, dissolved oxygen 8.0-8.1 mg/L; Concentration: >100 mg/L for 96 hr /purity 99.9%/

LC50; Species: Pimephales promelas (Fathead minnow); Conditions: freshwater, static, 23-25 °C, pH 7.7-8, alkalinity 50 mg/L CaCO3, dissolved oxyen 6.0-5.4 mg/L; Concentration: 23 mg/L for 96 hr /purity 99.9%/

EC50; Species: Selenastrum capricornutum (green algae); Conditions: freshwater, static; Concentration: >124.6 mg/L for 72 hr; Effect: growth inhibition /purity 92.9%/

LC50; Species: Leuciscus idus (orfe); Conditions: freshwater, static; Concentration: 49 gm/L for 48 hr European Chemicals Agency; IUCLID Dataset for Dimethyl cyclohexane-1,4-dicarboxylate (CAS 94-60-0) p.13 (2000); Available from, as of August 13, 2014:

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 31(SRC), determined from a structure estimation method(2), indicates that dimethyl hexahydroterephthalate is expected to have very high mobility in soil(SRC). Volatilization of dimethyl hexahydroterephthalate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.7X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 4.41X10-3 mm Hg(3), and water solubility, 1.2X10+4 mg/L(4). Volatilization from dry soil surfaces may not be an important fate process based upon its vapor pressure(SRC). Results of several biodegradation tests indicate that dimethyl hexahydroterephthalate is inherently biodegradable(5) and that biodegradation may be an important fate process in the environment(5,6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 31(SRC), determined from a structure estimation method(2), indicates that dimethyl hexahydroterephthalate 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 9.7X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 4.41X10-3 mm Hg(4), and water solubility, 1.2X10+4 mg/L(5). According to a classification scheme(6), an estimated BCF of 11(SRC), from an estimated log Kow of 2.11(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A base-catalyzed second-order hydrolysis rate constant of 0.00243 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 9 years and 331 days at pH values of 7 and 8, respectively(2). Results of several biodegradation tests indicate that dimethyl hexahydroterephthalate is inherently biodegradable(7) and that biodegradation may be an important fate process in the environment(7,8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethyl hexahydroterephthalate, which has an extrapolated vapor pressure of 4.41X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dimethyl hexahydroterephthalate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 days(SRC), calculated from its rate constant of 7.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Dimethyl hexahydroterephthalate does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; See the data in Chemical Explorer/[USEPA; ICSS Dashboard Application; Available from, as of March 28, 2014: http://actor.epa.gov/dashboard/]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of dimethyl hexahydroterephthalate can be estimated to be 31(SRC). According to a classification scheme(2), this estimated Koc value suggests that dimethyl hexahydroterephthalate is expected to have very high mobility in soil.

AEROBIC: Using OECD Guide-line 302B (Inherent biodegradability: Modified Zahn-Wellens Test) and a non-adapted activated sludge inoculum, dimethyl hexahydroterephthalate reached 98% after 14-days(1). Dimethyl hexahydroterephthalate, present at 52.3 mg/L, reached 82% of its theoretical BOD in 4 weeks using a non-adapted activated sludge inoculum(1). Using OECD Guide-line 301B (Ready biodegradation using the CO2 evolution test, Modified Sturm), dimethyl hexahydroterephthalate reached 81% and 79% degradation at 10 mg/L and 20 mg/L concentrations, respectively, over a 35-day incubation period(2); time for 10% degradation was 11 days(2).

An estimated BCF of 11 was calculated in fish for dimethyl hexahydroterephthalate(SRC), using an estimated log Kow of 2.11(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for dimethyl hexahydroterephthalate is estimated as 9.7X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 4.41X10-3 mm Hg(1), and water solubility, 1.2X10+4 mg/L(2). This Henry's Law constant indicates that dimethyl hexahydroterephthalate is expected to be essentially nonvolatile from water surfaces(3). Dimethyl hexahydroterephthalate's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Volatilization from dry soil surfaces may not be an important fate process based upon its vapor pressure(SRC).

/LABORATORY ANIMALS: Acute Exposure/ Not irritating for rabbit eye.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Exposure levels: 0, 0.1, 0.3, and 1.0% in diet; Actual doses received: Males: 0, 81, 246, 871 mg/kg; Females: 0, 86, 259, 894 mg/kg. Repeated oral-dose toxicity /in/ Sprague-Dawley (CD(SD)BR) /rats (males and females 5/sex) for/ 4-weeks...Rats, were approximately 6-7 weeks in age and weighed 177 g (males) and 143 g (females) at study initiation. Animals were weighed and had detailed clinical observations recorded on Days 0, 4, 7, 14, 18, 22, and 29. Feed intake was assessed twice/week. At termination hematology (Hb conc., Hct, RBC count and morphology, WBC count and diff., and plt. Count) and clinical chemistries (AST, ALT, SDH, ALK, Creat., BUN, and gluc.) were conducted. At termination, animals underwent a gross examination with the following organs weighed: liver, spleen, kidneys, adrenals, testes, and thymus. Organs examined by histology included: trachea, lungs, heart, esophagus, stomach, small & large intestine, pancreas, liver, salivary glands, kidney, urinary bladder, pituitary, adrenals, thyroids, parathyroids, thymus, spleen, mesenteric lymph nodes, bone marrow, brain, testes, epididymis, accessory sex organs in males, fallopian tubes, uterus, vagina and ovaries. NOAEL (NOEL): 1.0%; [871 mg/kg (males) and 894 mg/kg (females)]. There were no mortalities or clinical signs related to exposure. There were no differences in body weights, feed consumption, hematology, clinical chemistries, and organ weights compared to controls. There were no gross or histological changes observed. CHDA induced essentially no toxicity following 4 weeks of exposure at a high exposure rate (1% of diet).

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ /Dose/ 0, 1.5, 4.5, and 15.0 mg/g of feed (0.15, 0.45, and 1.5%) Approx. 92, 276, and 888 mg/kg (male), and 111, 351, and 1124 mg/kg (female). /Rats Sprague-Dawley, exposure 38-57 days/. The study consisted of four phases: pre-mating (14 days); mating (1 to 14 days); pregnancy (21 to 23 days); and early lactation (4 to 6 days). The male rats were treated throughout the study, a period of 50 days. The female rats were treated throughout the study until they were euthanized, a period of approximately 38-57 days. The male rats were euthanized on Day 51. The female rats that delivered a litter, and their offspring, were euthanized on Days 4, 5, or 6 postpartum. Female rats that showed evidence of mating but did not deliver were euthanized on Day 23 of gestation. The study design included the additional endpoints of epididymal spermatozoan numbers and motility, and testicular spermatid head counts. Male rats that consumed diets containing 15.0 mg/g (1.50%) of the test substance exhibited reduced mean body weights and/or feed consumption values for the duration of the study. However, there were no adverse effects on fertility, histology of the testes and epididymis, or testicular and epididymal sperm counts. No treatment related effects were seen in male rats from the lower dose groups. There were no treatment related effects or histopathological alterations seen in the ovaries of female rats from any dose group and there were no biologically significant changes in their offspring. There were no toxicologically significant differences in the reproductive parameters evaluated including reproductive performance, fertility index, fecundity index, precoital interval, gestation duration, numbers of implants, number of corpora lutea, pre- and post implantation loss, pup survival, live and dead pups, male and female pups, pup body weight and body weight changes. Although the duration of the gestation phase was shorter (p < 0.05) for female rats from the mid dose group, there was no apparent effect on pup viability. Mean pup weight change and percent pup weight change from Days 0 to 4 were also significantly (p < 0.05) higher for pups from the low dose group when compared with the control group, but these changes were not considered biologically significant. /NOAEL (male, paternal) 888 mg/kg; NOAEL (female, maternal) 1124 mg/kg; NOAEL (offsping, F1) 888 mg/kg/.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Exposure levels: 0, 1.5, 4.5, and 15.0 mg/g of feed (0.15, 0.45, and 1.5%) Actual /oral/ dose levels: Approx. 92, 276, and 888 mg/kg (male), and 111, 351, and 1124 mg/kg (female Control group and treatment: Controls were exposed to basal diet. Duration of test: The study consisted of four phases: pre-mating (14 days); mating (1 to 14 days); pregnancy (21 to 23 days); and early lactation (4 to 6 days). The male rats were treated throughout the study, a period of 50 days. The female rats were treated throughout the study until they were euthanized, a period of approximately 38-57 days. The male rats were euthanized on Day 51. The female rats that delivered a litter, and their offspring, were euthanized on Days 4, 5, or 6 postpartum. Female rats that showed evidence of mating but did not deliver were euthanized on Day 23 of gestation. Remarks: The study design included the additional endpoints of epididymal spermatozoan numbers and motility, and testicular spermatid head counts. Maternal/Paternal toxicity NOAEL: 1.5%; or 888 mg/kg for males and 1124 mg/kg for females Repro./Develop. toxicity NOAEL: 1.5%; or 888 mg/kg for males and 1124 mg/kg for females Parental toxic responses: Male rats that consumed diets containing 15.0 mg/g (1.50%) of the test substance exhibited reduced mean body weights and/or feed consumption values for the duration of the study. However, there were no adverse effects on fertility, histology of the testes and epididymis, or testicular and epididymal sperm counts. No treatment-related effects were seen in male rats from the lower dose groups. There were no treatment-related effects or histopathological alterations seen in the ovaries of female rats from any dose group and there were no biologically significant changes in their offspring. Postnatal toxic responses: There were no toxicologically significant differences in the reproductive parameters evaluated including reproductive performance, fertility index, fecundity index, precoital interval, gestation duration, numbers of implants, number of corpora lutea, pre- and post-implantation loss, pup survival, live and dead pups, male and female pups, pup body weight and body weight changes. Although the duration of the gestation phase was shorter (p = 0.05) for female rats from the mid-dose group, there was no apparent effect on pup viability. Mean pup weight change and percent pup weight change from Days 0 to 4 were also significantly (p = 0.05) higher for pups from the low-dose group when compared with the control group, but these changes were not considered biologically significant. DMCD did not affect the reproductive capacity of the adult animals in this study.

For more Non-Human Toxicity Excerpts (Complete) data for DIMETHYL HEXAHYDROTEREPHTHALATE (9 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of dimethyl hexahydroterephthalate with photochemically-produced hydroxyl radicals has been estimated as 7.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.00243 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 9 years and 331 days at pH values of 7 and 8, respectively(1). Dimethyl hexahydroterephthalate does not contain chromophores that absorb at wavelengths >290 nm(2) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of dimethyl hexahydroterephthalate is 1000 or greater; the data may be greatly underestimated(1).

Occupational exposure to dimethyl hexahydroterephthalate may occur through inhalation and dermal contact with this compound at workplaces where dimethyl hexahydroterephthalate is produced or used. Limited population exposure may occur via ingestion of and dermal contact with contaminated water in the vicinity of a spill site. (SRC)

Dimethyl hexahydroterephthalate's production and use in the synthesis of polyester resins, polyamides, alkyds, plasticizers, and polyurethane coatings may result in its release to the environment through various waste streams. If released to air, an extrapolated vapor pressure of 4.41X10-3 mm Hg at 25 °C indicates dimethyl hexahydroterephthalate will exist solely as a vapor in the atmosphere. Vapor-phase dimethyl hexahydroterephthalate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2 days. Dimethyl hexahydroterephthalate does not contain chromophores that absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight. If released to soil, dimethyl hexahydroterephthalate is expected to have very high mobility based upon an estimated Koc of 31. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 9.7X10-8 atm-cu m/mole. Volatilization from dry soil surfaces may not be an important fate process based upon its vapor pressure. Results of several biodegradation tests indicate that dimethyl hexahydroterephthalate is inherently biodegradable and that biodegradation may be an important fate process in the soil and water environments. If released into water, dimethyl hexahydroterephthalate is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 11 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis in acidic and neutral conditions is too slow to be of environmental importance (estimated half-lives on the order of years); hydrolysis half-life in very alkaline media of pH 9 is on the order of one month at 25 °C. Occupational exposure to dimethyl hexahydroterephthalate may occur through inhalation and dermal contact with this compound at workplaces where dimethyl hexahydroterephthalate is produced or used. Limited population exposure may occur via ingestion of and dermal contact with contaminated water in the vicinity of a spill site. (SRC)

Used in plasticizers and polymers; [HSDB]

Plasticizers, polymers

Used as a chemical intermediate in the production of trans-1,4-cyclohexane diisocyanate.

Used as a chemical intermediate in the commercially important production of 1,4-cyclohexanedimethanol.

Used for the synthesis of polyester resins, polyamides, alkyds, and plasticizers. Used to make polyester polyols for polyurethane coatings for automotive, industrial maintenance, transportation, and aerospace applications.

/Ingredient of crude MCHM/ dimethyl 1,4-cyclohexanedicarboxylate 1%

2023: 1,000,000 - <8,500,000 lb

2023: 150,000,000 - <500,000,000 lb

1,4-Cyclohexanedicarboxylic acid, dimethyl ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5342]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,4-Cyclohexanedicarboxylic acid, 1,4-dimethyl ester. Aggregated National Production Volume: 100 to < 500 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1,4-Cyclohexanedicarboxylic acid, 1,4-dimethyl ester. National Production Volume: Withheld.

Intermediate

Intermediate

All Other Basic Organic Chemical Manufacturing

All Other Basic Organic Chemical Manufacturing

1,4-Cyclohexanedicarboxylic acid, 1,4-dimethyl ester: ACTIVE

1,4-Cyclohexanedicarboxylic acid, 1,4-dimethyl ester, trans-: ACTIVE