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Home > Encyclopedia > Triethylene glycol monoethyl ether

Triethylene glycol monoethyl ether

Triethylene glycol monoethyl ether structure

Triethylene glycol monoethyl ether 

structure
  • CAS No:

    112-50-5

  • Formula:

    C8H18O4

  • Chemical Name:

    Triethylene glycol monoethyl ether

  • Synonyms:

    Ethanol,2-[2-(2-ethoxyethoxy)ethoxy]-;2-[2-(2-Ethoxyethoxy)ethoxy]ethanol;Dowanol TE;Ethoxytriglycol;Triethylene glycol monoethyl ether;Triglycol monoethyl ether;3,6,9-Trioxaundecan-1-ol;Ethoxytriethylene glycol;Ethyltriglycol;Poly-solve TE;12: PN: WO2017021334 SEQID: 18 claimed sequence

  • Categories:

    Specialty Chemicals

Description

COLOURLESS HYGROSCOPIC LIQUID.


Ethoxy triglycol is an odorless colorless liquid. Sinks and mixes with water. (USCG, 1999)|Liquid|COLOURLESS HYGROSCOPIC LIQUID.


Ethoxy triglycol is an odorless colorless liquid. Sinks and mixes with water. (USCG, 1999)

Triethylene glycol monoethyl ether Basic Attributes

178.226

178.23

203-978-9

4G0E2G9582

0718

DTXSID3024368

Colorless liquid

2909499000

Characteristics

47.92000

-0.98

Ethoxy triglycol is an odorless colorless liquid. Sinks and mixes with water. (USCG, 1999)

1.018 g/cm3 @ Temp: 25 °C

-18.7 °C

255.4 °C @ Press: 760 Torr

106.4±21.8 °C

1.431

Solubility in water: very good

6.8 @ 20°C

Relative vapour density (air = 1): 6.2

Explosive limits , vol% in air: 1.0-6.5

ODORLESS

Henry's Law constant = 4.77X10-14 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 4.54X10-11 cu cm/molec-sec at 25 °C (est)

Water soluble.

Alcohols and Polyols

ETHOXY TRIGLYCOL is a ethoxy-alcohol derivative. The ether being relatively unreactive. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert alcohols to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Safety Information

NONH for all modes of transport

-

KK8950000

Separated from strong oxidants. Ventilation along the floor.

P264, P280, P305+P351+P338, P33, P313

H319

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.

Glycol ethers, glycols, ketones, and alcohols undergo violent decomposition in contact with 68-72% perchloric acid

Combustible.

|Warning|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 112 companies from 2 notifications to the ECHA C&L Inventory.

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing. Fire Extinguishing Agents: Dry chemical, carbon dioxide, or alcohol foam. (USCG, 1999)|Use water spray, alcohol-resistant foam, powder, carbon dioxide.

Chemical safety goggles and adequate protective clothing. (USCG, 1999)

Combustible|COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS.

Explosive limits , vol% in air: 1.0-6.5

Collect leaking liquid in sealable containers. Wash away remainder with plenty of water.

Separated from strong oxidants. Ventilation along the floor.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance defats the skin, which may cause dryness or cracking.

NO open flames.

Use ventilation.

Protective gloves.

Wear safety spectacles.

| 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.

Effluent from advanced waste treatment plants in Lake Tahoe, CA and Blue Plains, Washington, DC contained triethylene glycol monoethyl ether at unreported concentrations(1).

SOIL: Triethylene glycol monoethyl ether was detected 20 times in 300,000 groundwater, surface water and soil samples from Superfund sites(1).

Toxicity

LD50 Rat oral 10.6 g/kg|LD50 Rabbit dermal 8 mL/kg (8.2 g/kg)|LD50 Rat (Wistar, male) oral 8.5 g/kg|LD50 Rabbit dermal (abraded, 24 hr occlusion) >2.0 g/kg

Triethylene glycol monoethyl ether's production and use as a component of brake fluid(1) and to a lesser extent as a solvent in lacquers and paints(2) and chemcial intermediate(3) may result in its release to the environment through various waste streams(SRC).

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 monoethyl ether is expected to have very high mobility in soil(SRC). Volatilization of triethylene glycol monoethyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.8X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Triethylene glycol monoethyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.01 mm Hg(4). Based on aqueous studies giving degradation ranges of 1%(5) to 100%(6) from 5 to 20 days, respectively, triethylene glycol monoethyl ether is expected to biodegrade in soil.|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 monoethyl 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 4.8X10-14 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 -0.96(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Triethylene glycol monoethyl ether is expected to biodegrade based on studies with degradation ranges of 1%(8) to 100%(9) from 5 to 20 days, respectively.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethylene glycol monoethyl ether, which has a vapor pressure of 0.01 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethylene glycol monoethyl 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 8.5 hours(SRC), calculated from its rate constant of 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of triethylene glycol monoethyl ether with photochemically-produced hydroxyl radicals has been estimated as 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).

An estimated BCF of 3 was calculated in fish for triethylene glycol monoethyl ether(SRC), using an estimated log Kow of -0.96(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).

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

The Henry's Law constant for triethylene glycol monoethyl ether is estimated as 4.8X10-14 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that triethylene glycol monoethyl ether is expected to be essentially nonvolatile from water surfaces(2). Triethylene glycol monoethyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.01 mm Hg(3).

GROUNDWATER: Triethylene glycol monoethyl ether was detected 20 times in 300,000 groundwater, surface water and soil samples from Superfund sites(1).|DRINKING WATER: Triethylene glycol monoethyl ether was detected in drinking water in Cincinnati, OH in 1978 and 1980, in Philadelphia, PA in 1976, and in Ottumwa, IO in 1976 at unreported concentrations(1).|SURFACE WATER: Triethylene glycol monoethyl ether was detected 20 times in 300,000 groundwater, surface water and soil samples from Superfund sites(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 621 workers (44 of these are female) are potentially exposed to triethylene glycol monoethyl ether in the US(1). Occupational exposure to triethylene glycol monoethyl ether may occur through inhalation and dermal contact with this compound at workplaces where triethylene glycol monoethyl ether is produced or used(SRC). Monitoring and use data indicate that the general population may be exposed to triethylene glycol monoethyl ether via dermal contact with brake fluid and via ingestion of contaminated drinking water(SRC).

Drug Information

The in vitro rate of penetration of TGEE through human epidermis was reported as 0.024 mg/cm sq/hr.|... It is absorbable by skin /of expl animals/ in toxic amt.

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.

No appreciable hazard in ordinary handling or use. (USCG, 1999)

Wash affected parts with water. (USCG, 1999)


Fresh air, rest.


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.

/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/

triethylene glycol monoethyl ether

Dry skin.

Triethylene glycol monoethyl ether Use and Manufacturing

Methods of Manufacturing

BY DIRECT ALKYLATION OF TRIETHYLENE GLYCOL WITH ALKYLATING AGENT IN PRESENCE OF ALKALI.|Ethanol + ethylene oxide (epoxidation; coproduced with diethylene glycol monoethyl ether/ethylene glycol monoethyl ether)|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/

Uses

Functional fluids (closed systems)


Automotive care products

Production

10,000,000 - 50,000,000 lb|(1972) 1.28X10+10 GRAMS (ALL MONOETHERS)|(1975) 1.2X10+10 GRAMS|(2006) 1,612 million lb annual capacity /Glycol ethers/|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2374]|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).

(ALL TRIETHYLENE GLYCOL MONOETHERS) 95% AS A SOLVENT IN HYDRAULIC BRAKE FLUIDS; 5% AS A SOLVENT IN PROTECTIVE COATINGS, PRINTING INKS, & CHEMICAL SPECIALTIES(1972)

All other basic organic chemical manufacturing|Ethanol, 2-[2-(2-ethoxyethoxy)ethoxy]-: ACTIVE|IT MAY APPEAR IN 8 ISOMERIC FORMS, OF WHICH COMMERCIAL PRODUCT IS BELIEVED TO BE A MIXT.

LIQ-GAS PHASE CHROMATOGRAPHY WOULD BE USEFUL IN RESOLVING MIXT, WHICH COULD THEN BE IDENTIFIED BY INFRARED OR MASS SPECTROPHOTOMETRY. /GLYCOL ETHERS/

Computed Properties

Molecular Weight:178.23
XLogP3:-0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:9
Exact Mass:178.12050905
Monoisotopic Mass:178.12050905
Topological Polar Surface Area:47.9
Heavy Atom Count:12
Complexity:77.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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