1,4-Cyclohexanedimethanol

Sweet (1,3/1,4-cyclohexanedimethanol mixture)

Mild hydrocarbon odor

1.0381 at 25 °C/4 °C

1.0381 @25 °C

Liquid

White waxy solid

In water, 920,000 mg/L at 20 °C

Solluble in ethyl alcohol

166 °C

330 °F OC

286 °C (cis-isomer), 283 °C (trans-isomer)

274 °C @760 [mm Hg]

This chemical does not meet GHS hazard criteria for 5.8% (27 of 467) of reports.

Danger

H318 (63.6%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, P305+P354+P338, P317, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 467 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: 1,4-Cyclohexanedimethanol

Regulation (EC) No 1935/2004 (amended)

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

Status: Active Update: 22-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14211

1,4-Cyclohexanedimethanol: Does not have an individual approval but may be used under an appropriate group standard

1 - Materials that, under emergency conditions, can cause significant irritation.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Eye Dam. 1 (63.6%)

Eye Dam. 1 (10%)

Eye damage - category 1

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.

9.6 [mg/m3]

110 [mg/m3]

630 [mg/m3]

LC50; Species: Pimephales promelas (Fathead minnow); Conditions: freshwater, static, 19-20 °C, pH 8.2-8.5, dissolved oxygen 8.2-9.0 mg/L; Concentration: >125.3 mg/L for 96 hr

LC50; Species: Daphnia magna (Water flea); Conditions: freshwater, static; Concentration: >100 mg/L for 96 hr

EC50; Species: Pseudokirchneriella subcapitata (Green algae); Conditions: freshwater, static; Concentration: >122.9 mg/L for 72 hr; Effect: inhibition of biomass

EC50; Species: Pseudokirchneriella subcapitata (Green algae); Conditions: freshwater, static; Concentration: >122.9 mg/L for 72 hr; Effect: inhibition of growth

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that 1,4-cyclohexanedimethanol is expected to have very high mobility in soil(SRC). Volatilization of 1,4-cyclohexanedimethanol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.4X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 3.08X10-4 mm Hg(3), and water solubility, 1.92X10+5 mg/L(4). Volatilization from dry soil surfaces may not be an important fate process based upon its vapor pressure(SRC). Using the OECD-302B method (Zahn-Wellens/EMPA test for inherent biodegradability), 98% of initial 1,4-cyclohexanedimethanol was degraded over a 19-day incubation period which classified the compound as inherently biodegradable(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that 1,4-cyclohexanedimethanol 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 6.4X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 3.08X10-4 mm Hg(4), and water solubility, 9.2X10+5 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 1.14(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1,4-Cyclohexanedimethanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Using the method OECD-111, <1% of initial 1,4-cyclohexanedimethanol hydrolyzed under acidic, neutral or basic conditions after a 5-day period at 50 °C(7). Using the OECD-302B method (Zahn-Wellens/EMPA test for inherent biodegradability), 98% of initial 1,4-cyclohexanedimethanol was degraded over a 19-day incubation period which classified the compound as inherently biodegradable(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-cyclohexanedimethanol, which has a vapor pressure of 3.08X10-4 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1,4-cyclohexanedimethanol 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 18 hours(SRC), calculated from its rate constant of 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1,4-cyclohexanedimethanol may be removed from the air by wet and dry deposition(SRC). 1,4-Cyclohexanedimethanol 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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,4-cyclohexanedimethanol can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,4-cyclohexanedimethanol is expected to have very high mobility in soil.

An estimated BCF of 3 was calculated in fish for 1,4-cyclohexanedimethanol(SRC), using an estimated log Kow of 1.14(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 1,4-cyclohexanedimethanol is estimated as 6.4X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 3.08X10-4 mm Hg(1), and water solubility, 1.92X10+5 mg/L(2). This Henry's Law constant indicates that 1,4-cyclohexanedimethanol is expected to be essentially nonvolatile from water surfaces(3). 1,4-cyclohexanedimethanol'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/ Rats (10 used, not specified if per dose or total) were administered 1,4-cyclohexanedimethanol via oral gavage at doses of 400 - 6400 mg/kg-bw and were observed for 14 days. Animals appeared normal to very weak with prostration and vasodilatation.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Male (12/dose) and female (10/dose) Sprague-Dawley rats administered 1,4-cyclohexanedimethanol in their drinking water at concentrations of 0, 4.0, 8.0 or 12.5 mg/L for 13 weeks. The approximate dose levels achieved were 0, 256, 479 or 861 mg/kg-bw/day in males and 0, 440, 754 or 1754 mg/kg-bw/day in females. High-dose rats experienced decreased survival and had bloody or brown/red discolored urine, softened and/or reduced feces, reductions in body weights and weight gains, decreased feed consumption and increased urinary protein levels. No treatment-related effects were seen in animals receiving the mid- and low-dose levels. LOAEL (male) = 861 mg/kg-bw/day (based on decreased survival, abnormal urine and feces, reduced body weights and weight gains, decreased feed consumption and increased urinary protein levels) LOAEL (female) = 1754 mg/kg-bw/(based on decreased survival, abnormal urine and feces, reduced body weights and weight gains, decreased feed consumption and increased urinary protein levels) NOAEL (male) = 479 mg/kg-bw/day NOAEL (female) = 754 mg/kg-bw/day

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Male and female Sprague-Dawley rats (12/sex/dose) were administered 1,4-cyclohexanedimethanol in their drinking water at concentrations of 0, 4.0, 8.0 or 12.5 mg/L during pre-mating (56 days), mating (up to 14 days), gestation (21-22 days), and early lactation (4 days). The approximate dose levels achieved were 0, 256, 479 and 861 mg/kg-bw/day in males and 0, 385, 854 and 1360 mg/kg-bw/day in females. One male and one female from the high dose group were euthanized in extremis during the pre-mating period. High-dose animals (gender not specified) exhibited bloody or discolored urine, reductions in body weights and weight gains and decreased feed consumption. These signs persisted through lactation in females. Decreased food consumption during lactation days 0-4 was observed in mid-dose females. No treatment-related effects were seen in organ weights harvested and histologically examined. There was no treatment-related effect on epididymal or testicular sperm counts. A decrease in sperm motility was noted in some males at the highest dose. This effect was not statistically significant, but was considered to be biologically significant. There were no reductions in any of the fertility parameters or indices examined. Biologically significant changes in litters were only noted in pups from high dose dams. These pups exhibited decreased body weights and weight gains as well as decreased postnatal survival between days 0 and 4. The incidence of pups with no or small amounts of milk in their stomachs, and pups that were either missing (presumably cannibalized) or found dead was also higher from dams exposed to higher doses. No treatment-related effects were noted in the two lower dose groups in the reproductive parameters assessed (reproductive performance, gestation length, pup survival rate, prenatal loss, number of implantation sites, number of live and dead pups, pup sex ration, body weights and weight gains). The fetotoxicity noted occurred at levels that induced significant maternal toxicity. LOAEL (systemic toxicity, male) = 861 mg/kg-bw/day (based on bloody or discolored urine, reductions in body weights and weight gains and decreased feed consumption) LOAEL (systemic toxicity, female) = 1360 mg/kg-bw/day (based on bloody or discolored urine, reductions in body weights and weight gains and decreased feed consumption) NOAEL (systemic toxicity, male) = 479 mg/kg-bw/day NOAEL (systemic toxicity, female) = 854 mg/kg-bw/day LOAEL (developmental toxicity) = 1360 mg/kg-bw/day (based on decreased fetal weight and postnatal survival) NOAEL (developmental toxicity) = 854 mg/kg-bw/day LOAEL (reproductive toxicity) > (highest dose tested) NOAEL (reproductive toxicity) = 1360 mg/kg-bw/day

/ENDOCRINE MODULATION/ Eastman Tritan copolyester, a novel plastic from Eastman is manufactured utilizing three monomers, di-methylterephthalate (DMT), 1,4-cyclohexanedimethanol (CHDM), and 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) in various ratios. As with most any polymer, the monomers along with the high molecular weight oligomers, whose toxicity is most commonly represented by the monomers, make up the predominate amount of free chemicals available for leaching into the environment and/or foods. In light of the high level of public concern about the presence of endocrine (primarily estrogenic) activity ascribed to certain plastics and chemicals in the environment, Tritan's monomers were evaluated using QSAR for binding to the androgen receptor and estrogen receptors (alpha and beta) as well as a battery of in vitro and in vivo techniques to determine their potential androgenicity or estrogenicity. The findings were universally negative. When these data are coupled with other in vivo data developed to assess systemic toxicity and developmental and reproductive toxicity, the data clearly indicate that these monomers do not pose an androgenic or estrogenic risk to humans. Additional data presented also support such a conclusion for terephthalic acid (TPA). TPA is also a common polyester monomer and is the main mammalian metabolite formed from DMT. /Tritan copolyester/

For more Non-Human Toxicity Excerpts (Complete) data for 1,4-CYCLOHEXANEDIMETHANOL (8 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of 1,4-cyclohexanedimethanol with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 18 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1,4-Cyclohexanedimethanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Using the method OECD-111, <1% of initial 1,4-cyclohexanedimethanol hydrolyzed under acidic, neutral or basic conditions after a 5-day period at 50 °C(3). 1,4-Cyclohexanedimethanol 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 1,4-cyclohexanedimethanol is 1000 or greater; the data may be greatly underestimated(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,900 workers (63 of these were female) were potentially exposed to 1,4-cyclohexanedimethanol in the US(1). Occupational exposure to 1,4-cyclohexanedimethanol may occur through inhalation and dermal contact with this compound at workplaces where 1,4-cyclohexanedimethanol is produced or used(SRC). During product formulation, dermal, ocular and inhalation exposure of workers to the chemical may occur, particularly where manual or open processes are used(2). Limited population exposure may occur via ingestion of and dermal contact with contaminated water in the vicinity of a spill site(SRC).

1,4-Cyclohexanedimethanol's production and use as an intermediate in the production of polyester resins, films and coatings may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 3.08X10-4 mm Hg at 25 °C indicates 1,4-cyclohexanedimethanol will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase 1,4-cyclohexanedimethanol 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 18 hours. Particulate-phase 1,4-cyclohexanedimethanol will be removed from the atmosphere by wet and dry deposition. 1,4-Cyclohexanedimethanol 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, 1,4-cyclohexanedimethanol is expected to have very high mobility based upon an estimated Koc of 10. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 6.4X10-11 atm-cu m/mole. Volatilization from dry soil surfaces may not be an important fate process based upon its vapor pressure. Using the OECD-302B method (Zahn-Wellens/EMPA test for inherent biodegradability), 98% of initial 1,4-cyclohexanedimethanol was degraded over a 19-day incubation period which classified the compound as inherently biodegradable. If released into water, 1,4-cyclohexanedimethanol 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 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to 1,4-cyclohexanedimethanol may occur through inhalation and dermal contact with this compound at workplaces where 1,4-cyclohexanedimethanol 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)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

(14)C-1,4-cyclohexanedimethanol (CHDM) (70% trans-, 30% cis-isomers) was dissolved in water & given to male & female charles river cd (SD) rats by gavage in doses of 40 or 400 mg/kg of body wt. T/2 of CHDM in plasma from rats dosed with 400 mg/kg was about 13 minutes.

(14)C-1,4-cyclohexanedimethanol (CHDM) (70% trans-, 30% cis-isomers) was dissolved in water & given to male & female charles river cd (SD) rats by gavage in doses of 40 or 400 mg/kg of body wt. Metabolites were identified in plasma & urine by gas chromatography & gas chromatography-mass spectrometry. In addn to CHDM, 4-hydroxymethylcyclohexanecarboxylic acid was detected in plasma. Unchanged chdm was not detected in urine. The major metabolites identified in urine were cyclohexanedicarboxylic acid (68%) & 4-hydroxymethylcyclohexanecarboxylic acid (31%). Less than 2% of radioactivity in urine was not fully characterized. The cis-trans ratio of metabolites excreted in urine was the same as that of original dose.

(14)C-1,4-cyclohexanedimethanol (CHDM) (70% trans-, 30% cis-isomers) was dissolved in water & given to male & female charles river cd (SD) rats by gavage in doses of 40 or 400 mg/kg of body wt. (14)C-CHDM was rapidly absorbed from GI tract. After 48 hr, 95% of dose was excreted in urine, 2.5% in feces, & 0.03% respired as (14)CO2 & 0.4% remained in carcass. The recovery of radioactivity averaged 98.9% of dose. T/2 of CHDM in plasma from rats dosed with 400 mg/kg was about 13 minutes.

Used in polyester films and protective coatings; for the reduction of reaction time in esterification; as a chemical intermediate for linear polyester fibers, polyester resins, unsaturated resins, high performance polyester enamels, polyurethane foams and elastomers, cyclohexane dimethanol glycidyl ether, and for its dimethacrylate ester derivative; [HSDB]

Painting (Solvents) [Category: Paint]

Polyester films and protective coatings; reduction of reaction time in esterification

Used to make saturated and unsaturated polyester resins and coatings; used in unsaturated polyester resins for gel coats, sheet molding compounds, and injection moldable fiberglass-reinforced plastics; used as a chemical and pharmaceutical intermediate

1,4-Cyclohexanedimethanol is used for polyester films and protective coatings. The substance is an intermediate reactant, promoting reduction of reaction time in esterification for polymers industry.

Used in saturated polyesters used in powder, water- and solvent-borne coatings to enhance, eg, outdoor durability as well as chemical, hydrolytic, stain, humidity, and corrosion resistance. It is used for example in automotive, trains, buses, aerospace, and general industrial coatings.

(1979) No Data

(1981) No Data

(1979) No Data

(1981) No Data

2023: 250,000,000 - <400,000,000 lb

(1977) AT LEAST 4.54X10+9 GRAMS

(1982) PROBABLY GREATER THAN 2.27X10+6 GRAMS

1,4-Cyclohexanedimethanol 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#5374]

For more U.S. Production (Complete) data for 1,4-CYCLOHEXANEDIMETHANOL (6 total), please visit the HSDB record page.

The manufacture of 1,4-cyclohexanedimethanol can be accomplished by the catalytic reduction under pressure of dimethyl terephthalate in a methanol solution. This glycol also may be prepared by the depolymerization and catalytic reduction of linear polyesters that have alkylene terephthalates as primary constituents. Poly(ethylene terephthalate) may be hydrogenated in the presence of methanol under pressure and heat to give good yields.

CATALYTIC REDUCTION OF DIMETHYL TEREPHTHALATE IN METHANOL SOLN

All Other Basic Organic Chemical Manufacturing

1,4-Cyclohexanedimethanol: ACTIVE

1,4-Cyclohexanedimethanol, cis-: ACTIVE

1,4-Cyclohexanedimethanol, trans-: ACTIVE

Enzymatic hydrolytic degradation of polybutylene succinate (PBS), poly(polybutylenesuccinate-co-1,4-cyclohexane dimethanol) (PBS/CHDM) and poly(polybutylene succinate-co-diglycolic acid) (PBS/DGA) in mixed solvent of tetrahydrofuran (THF) and toluene was examined. Lipase was used as catalyst to degrade polymers with molecular weight of more than 100,000, and the molecular weight of products ranged from hundreds to thousands. Thermal decomposition temperatures of all products were below 250 °C. The degradation products of both PBS/CHDM and PBS/DGA showed two melting points at about 85 and 99 °C. Mass spectrometry (MS) was employed to obtain the molecular weight of oligomers extracted from the products, which proved to be low-polyesters with the molecular weight of less 1,000. The butanediol (BDO) monomer was found in PBS/CHDM degradation product... /Polybutylene succinate/

A monomeric component of a polymer with food packaging applications.