Triethylene glycol monomethyl ether

-1.46 (calculated)

-0.7

1.026 (USCG, 1999) - Denser than water; will sink

1.0494

Relative density (water = 1): 1.05

1.0494 @25 °C

In water, miscible

Soluble in water

Solubility in heptane = 1.5 wt%, completely soluble in acetone, benzene, ethyl ether, methanol, and carbon tetrachloride at 25 °C.

Solubility in water: miscible

greater than 230 °F (USCG, 1999)

245 °F (118 °C) (OPEN CUP)

114.4 °C c.c.

246 °C

249 °C

249 °C @760 [mm Hg]

This chemical does not meet GHS hazard criteria for 88.1% (290 of 329) of all reports.

Warning

H315 (11.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 329 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

Chemical: Ethanol, 2-[2-(2-methoxyethoxy)ethoxy]-

Ethanol, 2-[2-(2-methoxyethoxy)ethoxy]- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-[2-(2-methoxyethoxy)ethoxy]- 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: 10-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14921

Ethanol, 2-[2-(2-methoxyethoxy)ethoxy]-: Does not have an individual approval but may be used under an appropriate group standard

In lethal-dose animal studies, causes liver injury; Oral doses of 4000 mg/kg/day for 91 days cause testicular injury in rats; Developmental toxicity is seen in rats receiving >1000 mg/kg/day; Genotoxic studies were negative; [OECD SIDS: 2-(2-(2-Methoxyethoxy)ethoxy)ethanol - 1996] No listed effects of short-term or long-term exposure; [ICSC] May form unstable peroxides in the presence of oxygen; [CAMEO] May cause mild skin and eye irritation; [eChemPortal: SIDSUNEP] See GLYCOL ETHERS.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Triethylene glycol monomethyl ether is included on this list.

Manufacturers and processors of triethylene glycol monomethyl ether are required to conduct developmental neurotoxicity tests under TSCA section 4.

A testing consent order is in effect for developmental neurotoxicity testing for triethylene glycol monomethyl ether for health effects testing. FR citation: April 3, 1989.

Ethers, such as TRIETHYLENE GLYCOL METHYL ETHER, can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid.

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.

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.

Use powder, foam, carbon dioxide.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Give one or two glasses of water to drink.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

LC50 Daphnia magna (Water flea) >10000 mg/L/48 hr /Conditions of bioassay not specified in source examined/

LC50 Pimephales promelas (Fathead minnow) >10000 mg/L/96 hr /Conditions of bioassay not specified in source examined/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that triethylene glycol monomethyl ether is expected to have very high mobility in soil(SRC). Volatilization of triethylene glycol monomethyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Triethylene glycol monomethyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-3 mm Hg(SRC), determined from a fragment constant method(4). Triethylene glycol monomethyl ether has percent theoretical BOD values of 14 and 23 at 10 and 20 days, respectively(5), which suggest that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that triethylene glycol monomethyl ether 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 3.5X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -1.46(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Triethylene glycol monomethyl ether has percent theoretical BOD values of 14 and 23 at 10 and 20 days, respectively(8), which suggest that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethylene glycol monomethyl ether, which has an estimated vapor pressure of 3.5X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethylene glycol monomethyl ether 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 9.6 hours(SRC), calculated from its rate constant of 4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The CIR Expert Panel concluded that the alkyl PEG ethers, listed below, are safe in the present practices of use and concentration described in this safety assessment when formulated to be nonirritating. This assessment is also intended to address future alkyl PEG ether cosmetic ingredients that vary from those ingredients recited herein only by the number of ethylene glycol repeat units...PEG-3 Methyl Ether...

Safe for use in cosmetics, with qualifications

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

Acute oral toxicity was evaluated in groups of 10 male albino Wistar rats administered single doses of undiluted Poly Solv TM (triethylene glycol monomethyl ether) by oral gavage at levels of 5.0, 7.12, 10.14, or 14.43 g/kg body weight. Mortality was observed in 1 animal in the 10.14 g/kg dose group, and in 8 animals in the highest dose group. The LD50 value was calculated to be 12.6 g/kg (10.4 to 15.3 g/kg 95% confidence limits) by the Litchfield and Wilcoxon method. Clinical observations included ataxia, piloerection, lethargy, blood in the anogenital area (1 rat), ptosis, and coma. Gross necropsy of animals in the highest dose group revealed yellow intestines with blood in the lumen, dark liver, and blood in the stomach.

Acute oral toxicity was evaluated in groups of 6 male rats (strain not reported) administered single doses of Dowanol TMH (triethylene glycol monomethyl ether) as a 20% solution in corn oil at levels of 0.5, 1.0, 2.0, and 3.98 g/kg body weight. Mortality was not observed and an LD50 value was not reported. Clinical findings and gross necropsy were not reported.

Acute oral toxicity was evaluated in groups of 5 male albino rats (strain not reported) administered single doses of undiluted methoxytriglycol by oral gavage at levels of 4.0, 8.0, and 16.0 mL/kg of body weight. Mortality was observed in all 5 animals in the 16.0 mL/kg dose group; the LD50 value was calculated to by 11.3 mL/kg by the moving average method. Clinical observations were not reported. Gross necropsy findings included congested lungs, mottled livers and kidneys, gastrointestinal tract irritation and slightly congested adrenals.

Acute dermal toxicity was evaluated in 10 New Zealand White rabbits receiving single occluded applications of Poly Solv TE (methoxy triethylene glycol) at a dose level of 2.0 g/kg of body weight. The test article was held in contact with the skin (half intact, half abraded) for a 24 hour period. Mortality was not observed. Clinical observations included dermal erythema and edema. Gross necropsy revealed mottled liver in 1 animal, white nodules in 2 animals, pocked kidneys in 2 animals, and dark lung areas in 1 animal.

For more TSCA Test Submissions (Complete) data for TRIETHYLENE GLYCOL MONOMETHYL ETHER (24 total), please visit the HSDB record page.

/EPIDEMIOLOGY STUDIES/ Ethylene glycol ethers (EGEs) including diglyme are used in the manufacture of semiconductors. Epidemiological studies of semiconductor populations evaluated potential adverse reproductive outcomes. ... In each of these studies, workers were exposed to mixtures including diglyme but not to diglyme alone. ... Exposure to EGEs was determined using questionnaires from subjects about the work performed and an assessment of the work environment by industrial hygienists, but no measurements of personal or area exposures were made. Workers in the fabrication area were considered exposed to EGEs. For the retrospective study, information on pregnancy outcomes and potential confounders (age, smoking, ethnicity, education, income, year of pregnancy, and stress) was obtained through a comprehensive interviewer-administered interview of female employees. The prospective study of early fetal loss and fecundity (probability of conception per menstrual cycle) was conducted in a subset of female employees from five plants. Daily diaries and measurements of daily urinary human chorionic gonadotrophin (hCG) levels for 6 months were collected in addition to the comprehensive interview. Of the 891 medically verified pregnancies identified for the retrospective study, 774 (86.9%) were live births, 113 (12.7%) were spontaneous abortions, and 4 (0.4%) were stillbirths. The overall unadjusted relative risk (RR) for spontaneous abortions was 1.45 (95% confidence interval [CI] = 1.02-2.05) and changed little after adjusting for confounders (adjusted RR =1.43; 95% CI = 0.95-2.09). When stratified by work group, the risk of spontaneous abortion was statistically significantly increased for female workers in the photolithography group (RR = 1.67; 95% CI = 1.04-2.55) and in the etching group (RR = 2.08; 95% CI = 1.27-3.19). For women working with higher levels of EGE only in masking, the risk for spontaneous abortion was increased 3-fold (RR = 3.38; 95% CI = 1.61-5.73). In the prospective study, no statistically significant differences were detected in the overall rate of spontaneous abortions between fabrication and non-fabrication workers or when pregnancy outcomes were examined by work group. However, the ability to conceive was lower among female workers exposed to EGEs (fertility rate [FR] = 0.37; 95% CI = 0.11-1.19). /Ethylene glycol ethers/

/BIOMONITORING/ In the present study, floor lacquerers' (n = 22) inhalation and total exposure to 2-(2-alkoxy)ethoxyethanols was measured. The measurements of inhalation exposure were done with charcoal tubes, and total exposure was biomonitored by urinalysis of 2-(2-alkoxyethoxy)acetic acids. The 8 hr inhalation exposures of floor lacquerers to 2-(2-methoxyethoxy)ethanol (DEGME), 2-(2-ethoxyethoxy)ethanol (DEGEE) and 2-(2-butoxyethoxy)ethanol (DEGBE) were in average 0.23 +/- 0.07 ppm (average +/-S.D., n = 3), 0.08 +/- 0.07 ppm (n = 16), and 0.05 +/- 0.03 ppm (n = 16), respectively. The excretions of 2-(2-methoxyethoxy)acetic acid (MEAA), 2-(2-ethoxyethoxy)acetic acid (EEAA) and 2-(2-butoxyethoxy)acetic acid (BEAA) were in average 4.9 +/- 4.3 mmol/mol creatinine, 9.3 +/- 8.0 mmol/mol creatinine and 9.2 +/- 7.4 mmol/mol creatinine, respectively. A linear relationship was found between the urinary 2-(2-alkoxyethoxy)acetic acid concentrations and the preceding 8-hr occupational exposure to 2-(2-alkoxyethoxy)ethanol.

Triethylene glycol monomethyl ether's production and use as a plasticizer intermediate(1), coupling solvent, brake/hydraulic fluid blending component, wetting agent, and solvent may result in its release to the environment through various waste streams(SRC).

AEROBIC: Triethylene glycol monomethyl ether has 10 and 20 day theoretical BOD values of 14 and 23, respectively(1). A study using activated sludge gave a degradation rate for diethylene glycol monoethyl ether of 0.22/hour(2) giving a half-life of 3.2 hours(SRC).

An estimated BCF of 3 was calculated in fish for triethylene glycol monomethyl ether(SRC), using an estimated log Kow of -1.46(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Triethylene glycol monomethyl ether is included on this list.

Manufacturers and processors of triethylene glycol monomethyl ether are required to conduct developmental neurotoxicity tests under TSCA section 4.

A testing consent order is in effect for developmental neurotoxicity testing for triethylene glycol monomethyl ether for health effects testing. FR citation: April 3, 1989.

The main metabolic pathway for metabolism of TGME and TGEE (and presumably the category members) is oxidation via alcohol dehydrogenase that leads to the formation of an alkoxy acid. A second important route of metabolism is oxidation by P-450 mixed function oxidases (O-dealkylation) that lead to the formation of triethylene glycol (TEG). TEG may be oxidized to a carboxylic acid. The principal metabolite of TGME is believed to be 2-[2-(2-methoxyethoxy)ethoxy] acetic acid.

It is slowly absorbed through skin. Excessive exposure involving large areas of skin for extended periods of time would be required before serious effects would be expected.

The penetration of triethylene glycol monomethyl ether (TGME) through human skin was studied in vitro using the epidermis from human abdominal skin. An area of 2.54 sq cm was exposed in a glass diffusion apparatus for treatment. The diffusion rate for TGME is 34 ug/sq cm/hr.

CIR ingredient: PEG-3 Methyl Ether

Used as coupling solvent (water-based paints), for blending brake and hydraulic fluids, and as a plasticizer and wetting agent (resins and paints); [HSDB] Used as raw material for automotive hydraulic brake fluids and a solvent in coatings, printing inks, cleaning products, cutting oils, and deicing agents; [eChemPortal: SIDSUNEP]

Metal Machining [Category: Heat or Machine]

Coupling solvent (water-based paints), brake/hydraulic fluid blending component, plasticizer/wetting agent (resins, paints), solvent.

A solvent and plasticizer intermediate.

(1972) 2.27X10+9 GRAMS (ALL MONOETHERS)

(1975) 2.27X10+9 GRAMS (ALL MONOETHERS)

(1984) 7.53X10+10 g /Ethers of Polyhydric alcohols and their derivatives/

(1972) NEGLIGIBLE

(1975) NEGLIGIBLE

2023: 40,000,000 - <55,000,000 lb

(1972) 1.44X10+10 GRAMS

(1975) 1.77X10+10 GRAMS

(2006) 1,612 million lb annual capacity /Glycol ethers/

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2666]

This chemical is listed as a High Production Volume (HPV) (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).

Ethylene glycol monoethers are commercially manufactured by reaction of an alcohol with ethylene oxide. /Ethylene Glycol Monoethers/

Ethylene glycol monoethers are usually produced by reaction of ethylene oxide with the appropriate alcohol. A mixture of homologues is obtained ... The glycol monoethers can be converted to diethers by alkylation with common alkylating agents, such as dimethyl sulfate or alkyl halides ( Williamson synthesis). Glycol dimethyl ethers are formed by treatment of dimethyl ether with ethylene oxide. /Ethers/

Printing and Related Support Activities

Ethanol, 2-[2-(2-methoxyethoxy)ethoxy]-: ACTIVE