CAS NO: 112-27-6
Synonyms: TRIETHYLENE GLYCOL; trietilen glikol; triethilenglikol; trietilen glikol; triethylene glycol; triethileneglycol; trietilen glikoll; glikol trietilen; triethylene glycol; trietilen gılikol; triethylen glykol; 112-27-6; trietilen glikol; triethylene glycol; Triglycol; 2,2'-(Ethane-1,2-diylbis(oxy))diethanol; triethylene glycol; 2,2'-Ethylenedioxydiethanol; trietilen glikol; triethylene glycol; Triethyleneglycol; triethylene glycol; Trigen; Triethylenglykol;1,2-Bis(2-hydroxyethoxy)ethane; trietilen glikol; triethylene glycol; 2,2'-(Ethylenedioxy)diethanol; trietilen glikol; 2-[2-(2-Hydroxyethoxy)ethoxy]ethanol; triethylene glycol; trietilen glikol; triethylene glycol; 3,6-Dioxaoctane-1,8-diol; trietilen glikol; triethylene glycol; Ethanol, triethylene glycol; 2,2'-[1,2-ethanediylbis(oxy)]bis-; trietilen glikol; Di-beta-hydroxyethoxyethane; triethylene glycol; 2,2'-Ethylenedioxybis(ethanol); triethylene glycol; 2,2'-Ethylenedioxyethanol; triethylene glycol; 2,2'-[ethane-1,2-diylbis(oxy)]diethanol; trietilen glikol; triethylene glycol; Triethylene glcol; Glycol bis(hydroxyethyl) ether; Caswell No. 888; triethylene glycol; Ethylene glycol dihydroxydiethyl ether; trietilen glikol; Trigol; TEG; triethylene glycol; Triethylenglykol [Czech]; trietilen glikol; Bis(2-hydroxyethoxyethane); trietilen glikol; Ethanol, 2,2'-(ethylenedioxy)di-; trietilen glikol; triethylene glycol; UNII-3P5SU53360; trietilen glikol; triethylene glycol; 2,2'-(1,2-Ethanediylbis(oxy))bisethanol; trietilen glikol; triethylene glycol; Ethylene glycol-bis-(2-hydroxyethyl ether); EINECS 203-953-2; triethylene glycol; EPA Pesticide Chemical Code 083501; triethylene glycol; 2-[2-(2-HYDROXY-ETHOXY)-ETHOXY]-ETHANOL; trietilen glikol; BRN 0969357; Di-.beta.-hydroxyethoxyethane; trietilen glikol; 2-[2-(2-hydroxyethoxy)ethoxy]ethan-1-ol; triethylene glycol; AI3-01453; triethylene glycol; CHEBI:44926; Ethanol, 2,2'-(1,2-ethanediylbis(oxy))bis-; triethylene glycol; 3P5SU53360; trietilen glikol; triethylene glycol; NSC 60758; trietilen glikol; HSDB 898; trietilen glikol; NCGC00163798-03; trietilen glikol; Triethylene glycol, 99%; DSSTox_CID_1393; DSSTox_RID_76135; triethylene glycol; DSSTox_GSID_21393; CAS-112-27-6; Trigenos; triethylenglycol; CCRIS 8926; triethylene-glycol; Triethyleneglycol,; Tri-ethylene glycol; triethylene glycol; 3,8-diol; ACMC-1C4BE; triethylene glycol; EC 203-953-2; Triethylene glycol, puriss.; SCHEMBL14929; triethylene glycol; WLN: Q2O2O2Q; triethylene glycol; 3,6-Dioxa-1,8-octanediol; trietilen glikol; triethylene glycol; 4-01-00-02400 (Beilstein Handbook Reference); KSC909E5P; 2,2-(Ethylenedioxy)diethanol; triethylene glycol; 2,2-(Ethylenedioxy)diethanol.; trietilen glikol; triethylene glycol; di(2-ethylbutyrate), diacetate; triethylene glycol; trietilen glikol; triethylene glycol; Ethanol,2'-(ethylenedioxy)di-; CHEMBL1235259; trietilen glikol; triethylene glycol; DTXSID4021393; triethylene glycol; Triethylene Glycol Reagent Grade; trietilen glikol; CTK8A9257; trietilen glikol; NSC60758; STR02345; ZINC1690436; Tox21_112073; triethylene glycol; Tox21_202440; trietilen glikol; triethylene glycol; Tox21_300306; triethylene glycol; ANW-16436; LS-550; trietilen glikol; triethylene glycol; MFCD00002880; trietilen glikol; triethylene glycol; NSC-60758; triethylene glycol; STL282716; trietilen glikol; AKOS000120013; trietilen glikol; Triethylene Glycol (Industrial Grade); triethylene glycol; CS-W018156; trietilen glikol; triethylene glycol; DB02327; triethylene glycol; HY-W017440; trietilen glikol; MCULE-7605038595; trietilen glikol; NCGC00163798-01; trietilen glikol; NCGC00163798-02; trietilen glikol; NCGC00163798-04; trietilen glikol; triethylene glycol; NCGC00163798-05; trietilen glikol; triethylene glycol; NCGC00163798-06; triethylene glycol; NCGC00254097-01; trietilen glikol; NCGC00259989-01; 2-[2-(2-Hydroxyethoxy)ethoxy]ethanol #; triethylene glycol; AK-72565; triethylene glycol; BP-21036; SC-79003; trietilen glikol; Triethylene glycol, trietilen glikol; ReagentPlus(R), 99%; triethylene glycol; Ethanol,2'-[1,2-ethanediylbis(oxy)]bis-; trietilen glikol; FT-0652416; triethylene glycol; FT-0659862; trietilen glikol; NS00002182; trietilen glikol; triethylene glycol; 7813-EP2270101A1; trietilen glikol; 7813-EP2272849A1; triethylene glycol; 7813-EP2284165A1; 7813-EP2292597A1; trietilen glikol; 7813-EP2308858A1; triethylene glycol; 7813-EP2308865A1; trietilen glikol; triethylene glycol; 7813-EP2311816A1; trietilen glikol; 7813-EP2311817A1; trietilen glikol; triethylene glycol; 7813-EP2315303A1; trietilen glikol; 7813-EP2316905A1; trietilen glikol; 7813-EP2316906A2; 7813-EP2371809A1; trietilen glikol; triethylene glycol; 7813-EP2374895A1; 7813-EP2380568A1; M-6031; Triethylene glycol, SAJ first grade, >=96.0%; trietilen glikol; triethylene glycol; 2,2'-[Ethane-1,2-diylbis(oxy)]di(ethan-1-ol); trietilen glikol; Q420630; SR-01000944720; Triethylene glycol, Vetec(TM) reagent grade, 98%; J-506706; trietilen glikol; triethylene glycol; SR-01000944720-1; F0001-0256; triethylene glycol; Triethylene glycol, BioUltra, anhydrous, >=99.0% (GC); trietilen glikol; Z1318198494; Triethylene glycol, United States Pharmacopeia (USP) Reference Standard; trietilen glikol; triethylene glycol; 1,2-Bis(2-hydroxyethoxy)ethane; 2,2'-(1,2-Ethanediylbis(oxy))bisethanol; 2,2'-(ethylenedioxy)diethanol; triethylene glycol; 2,2'-Ethylenedioxybis(ethanol); trietilen glikol; triethylene glycol; 2,2'-Ethylenedioxydiethanol; triethylene glycol; 2,2'-Ethylenedioxyethanol; trietilen glikol; 3,6-Dioxaoctane-1,8-diol; trietilen glikol; triethylene glycol; Bis(2-hydroxyethoxyethane); triethylene glycol; Di-beta-hydroxyethoxyethane; trietilen glikol; Ethanol, 2,2'-(1,2-ethanediylbis(oxy))bis-; trietilen glikol; triethylene glycol; Ethanol, 2,2'-(ethylenedioxy)di-; triethylene glycol; Ethylene glycol dihydroxydiethyl ether; trietilen glikol; triethylene glycol; Ethylene glycol-bis-(2-hydroxyethyl ether); trietilen glikol; Glycol bis(hydroxyethyl) ether; trietilen glikol; Triethylene glycol; Triethyleneglycol; Triethylenglykol; trietilen glikol; triethylene glycol; 2,2'-(ethylenedioxy) diethanol; triethylene glycol; 2,2'-[ethane-1,2-diylbis(oxy)]diethanol; trietilen glikol; triethylene glycol; trietilen glikol; 2,2’- {ethane-1,2-diylbis(oxy)}diethanol; trietilen glikol; triethylene glycol; trietilen glikol; 2-[2-(2-hydroxyethoxy)ethoxy]ethan-1-ol; trietilen glikol; triethylene glycol; 2-[2-(2-Hydroxyethoxy)ethoxy]ethanol; Triethylene Glycol (TEG); triethylene glycol; Triethylene glycol, also known as TEG.; 1,2-Di(.beta.-hydroxyethoxy)ethane; triethylene glycol; 2,2'-(Ethylendioxy)diethanol; trietilen glikol; triethylene glycol; 2,2'-(etilendioxi)dietanol; trietilen glikol; 2,2'-(éthylenedioxy)diéthanol; trietilen glikol; triethylene glycol; 2-(2-(2-Hydroxyethoxy)ethoxy)ethanol; triethylene glycol; Ethanol, 2,2'-[1,2-ethanediylbis(oxy)]bis- (9CI); Ethylene Glycol – DE; trietilen glikol; Ethylene Glycol Antifreeze Grade; Ethylene Glycol Industrial Grade; triethylene glycol; Glikol trietylenowy; TEG (glycol); TEG HP; trietilen glikol; triethylene glycol; Tri Ethylene Glycol; Triethylene glycol (8CI); triethylene glycol; trietilen glikol; Triethylene Glycol HP; triethylene glycol; Triethylene Glycol Technical Grade; triethylene glycol; TRIETHYLENEGLYCOL HP; trietilen glikol; TRIETILENOGLICOL 98.5; trietilen glikol; triethylene glycol; Triglykol; 2,2'-[1,2-Éthanediylbis(oxy)]diéthanol; 2,2'-[1,2-Ethandiylbis(oxy)]diethanol; trietilen glikol; triethylene glycol; 2,2'-[Ethane-1,2-diylbis(oxy)]diethanol;
SUMMARY
Triethylene glycol, TEG, or triglycol is a colorless odorless viscous liquid with molecular formula HOCH2CH2OCH2CH2OCH2CH2OH. It is used as a plasticizer for vinyl polymers. It is also used in air sanitizer products, such as "Oust" or "Clean and Pure". When aerosolized it acts as a disinfectant. Glycols are also used as liquid desiccants for natural gas and in air conditioning systems. It is an additive for hydraulic fluids and brake fluids and is used as a base for "smoke machine" fluid in the entertainment industry.
Triethylene glycol is a colorless liquid with a mild odor. Dense than water. Triethylene glycol is a poly(ethylene glycol) that is octane-1,8-diol in which the carbon atoms at positions 3 and 6 have been replaced by oxygen atoms. It has a role as a plasticiser. It is a poly(ethylene glycol), a diol and a primary alcohol.
PROPERTIES
Triethylene glycol is a member of a homologous series of dihydroxy alcohols. It is a colorless, odorless and stable liquid with high viscosity and a high boiling point. Apart from its use as a raw material in the manufacture and synthesis of other products, triethylene glycol is known for its hygroscopic quality and its ability to dehumidify fluids. This liquid is miscible with water, and at a pressure of 101.325 kPa has a boiling point of 286.5°C and a freezing point of -7°C.
Triethylene glycol (TEG) is a liquid chemical compound with the molecular formula C6H14O4. Triethylene glycol is recognized for its hygroscopic quality and ability to dehumidify fluids. It is miscible with water and soluble in ethanol, acetone, acetic acid, glycerine, pyridine, and aldehydes. It is slightly soluble in diethyl ether, and insoluble in oil, fat, and most hydrocarbons.
CHEMICAL AND PHYSICAL PROPERTIES OF TRIETHYLENE GLYCOL
Triethylene glycol’s molecule formula: C6-H14-O4
Triethylene glycol’s molecular weight: 150.17
Triethylene glycol’s colour/form: colourless, liquid
Triethylene glycol’s odor: practically odorless
Triethylene glycol’s boiling point: 285°C; 165 °C at 14 mm Hg
Triethylene glycol’s melting point: -7°C
Triethylene glycol’s density: 1.1274 at 15°C/4 °C
Triethylene glycol’s heat of vaporization: 61.04 kJ/mol at 101.3 kPa /=760 mm Hg/
Triethylene glycol’s octanol/water partition coefficient: log Kow = -1.98
Triethylene glycol’s solubility: Miscible with alcohol, benzene, toluene; sparingly sol in ether; practically insol in petroleum ether. Soluble in oxygenated solvents. Slightly soluble in ethyl ether, chloroform; insoluble in petroleum ether. In water, miscible.
Triethylene glycol’s vapor pressure: 1.32X10-3 mm Hg at 25°C (est)
Triethylene glycol’s viscosity: 47.8 cP at 20°C
Triethylene glycol’s flash point: 350°F (177°C) (Open cup)
Triethylene glycol’s flammable limits: Lower flammable limit: 0.9% by volume; Upper flammable limit: 9.2% by volume
Triethylene glycol’s autoignition temperature: 700°F (371°C)
PREPARATIONS OF TRIETHYLENE GLYCOL
Triethylene glycol is prepared commercially as a co-product of the oxidation of ethylene at high temperature in the presence of silver oxide catalyst, followed by hydration of ethylene oxide to yield mono(one)-, di(two)-, tri(three)- and tetraethylene glycols.
METHODS OF MANUFACTURING OF TRIETHYLENE GLYCOL
Prepared from ethylene oxide and ethylene glycol in presence of sulfuric acid ... manufactured by forming ether-ester of hydroxyacetic acid with glycol and then hydrogenating.
Produced commercially as by-product of ethylene glycol production. Triethylene glycol's formation is favored by a high ethylene oxide to water ratio.
Diethylene glycol + ethylene oxide (epoxidation)
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/
GENERAL MANUFACTURING INFORMATION ABOUT TRIETHYLENE GLYCOL
Triethylene glycol is described as an oligomer of ethylene glycol. So-called polyglycols are higher molecular weight adducts of ethylene oxide and distinguised by intervening ether linkages in the hydrocarbon chain. After years of study, triethylene glycol was found to be the ideal chemical for aerial disinfection in sterile filling units because triethylene glycol had a high bactericidal potency at reasonable cost and was non-toxic. triethylene glycol was most effective at relative humidities of 30 to 55% and the rate of kill increased with temperature and degree of saturation of air with the vapor.
APPLICATIONS OF TRIETHYLENE GLYCOL
Triethylene glycol is used by the oil and gas industry to "dehydrate" natural gas. It may also be used to dehydrate other gases, including CO2, H2S, and other oxygenated gases. It is necessary to dry natural gas to a certain point, as humidity in natural gas can cause pipelines to freeze, and create other problems for end users of the natural gas. Triethylene glycol is placed into contact with natural gas, and strips the water out of the gas. Triethylene glycol is heated to a high temperature and put through a condensing system, which removes the water as waste and reclaims the triethylene glycol for continuous reuse within the system. The waste triethylene glycol produced by this process has been found to contain enough benzene to be classified as hazardous waste (benzene concentration greater than 0.5 mg/L).
The oil and gas industries use triethylene glycol to dehydrate natural gas as well as other gases including CO2, H2S, and other oxygenated gases. Industrial uses include adsorbents and absorbents, functional fluids in both closed and open systems, Intermediates, petroleum production processing aids, and solvents. Triethylene glycol is used in the manufacture of a host of consumer products that include anti-freeze, automotive care products, building and construction materials, cleaning and furnishing care products, fabric, textile, and leather products, fuels and related products, lubricants and greases, paints and coatings, personal care products, and plastic and rubber products.
Triethylene glycol is well established as a relatively mild disinfectant toward a variety of bacteria, influenza A viruses and spores of Penicillium notatum fungi. However, its exceptionally low toxicity, broad materials compatibility, and low odor combined with its antimicrobial properties indicates that it approaches the ideal for air disinfection purposes in occupied spaces. Much of the scientific work with triethylene glycol was done in the 1940s and 1950s, however that work has ably demonstrated the antimicrobial activity against airborne, solution suspension, and surface bound microbes. The ability of triethylene glycol to inactivate Streptococcus pneumoniae (original citation: pneumococcus Type I), Streptococcus pyogenes (original citation: Beta hemolytic streptococcus group A) and Influenza A virus in the air was first reported in 1943. Since the first report the following microorganisms have been reported in the literature to be inactivated in the air: Penicillium notatum spores, Chlamydophila psittaci (original citation: meningopneumonitis virus strain Cal 10 and psittacosis virus strain 6BC), Group C streptococcus, type 1 pneumococcus, Staphylococcus albus, Escherichia coli, and Serratia marcescens Bizio (ATCC 274). Solutions of triethylene glycol are known to be antimicrobial toward suspensions of Penicillium notatum spores, Streptococcus pyogenes (original citation: Beta hemolytic streptococcus Group A ), Streptococcus pneumoniae (original citation: pneumococcus Type I), Streptococcus viridans, and Mycobacterium bovis (original citation: tubercle bacilli Ravenel bovine-type). Further, the inactivation of H1N1 influenza A virus on surfaces has been demonstrated. The latter investigation suggests that triethylene glycol may prove to be a potent weapon against future influenza epidemics and pandemics. However, at least some viruses, including Pseudomonas phage phi6 become more infectious when treated with triethylene glycol.
HUMAN HEALTH EFFECTS
TOXICITY SUMMARY
Triethylene glycol (TEG) is a liquid higher glycol of very low vapor pressure with uses that are primarily industrial. It has a very low order of acute toxicity by iv, ip, peroral, percutaneous and inhalation (vapor and aerosol) routes of exposure. It does not produce primary skin iritation. Acute eye contact with the liquid causes mild local transient irritation (conjunctival hyperemia and slight chemosis) but does not induce corneal injury. Animal maximization and human volunteer repeated insult patch tests studies have shown that triethylene glycol does not cause skin sensitization. A study with Swiss-Webster mice demonstrated that triethylene glycol aerosol has properties of a peripheral chemosensory irritant material and caused a depression of breathing rate with an RD(50) of 5140 mg/cu m. Continuous subchronic peroral dosing of triethylene glycol in the diet of rats did not produce any systemic cumulative or long-term toxicity. The effects seen were dose-related increased relative kidney weight, increased urine volume and decreased urine pH, probably a result of the renal excretion of triethylene glycol and metabolites following the absorption of large doses of triethylene glycol. There was also decreased hemoglobin concentration, decreased hematocrit and increased mean corpuscular volume, probably due to hemodilution following absorption of triethylene glycol. The NOAEL was 20,000 ppm triethylene glycol in diet. Short-term repeated aerosol exposure studies in the rat demonstrated that, by nose-only exposure, the threshold for effects by respiratory tract exposure was 1036 mg/cu m. Neither high dosage acute nor repeated exposures to triethylene glycol produce hepatorenal injury characteristic of that caused by the lower glycol homologues. Elimination studies with acute peroral doses of triethylene glycol given to rats and rabbits showed high recoveries (91-98% over 5 days), with the major fraction appearing in urine (84-94%) and only 1% as carbon dioxide. triethylene glycol in urine is present in unchanged and oxidized forms, but only negligible amounts as oxalic acid. Developmental toxicity studies with undiluted triethylene glycol given by gavage produced maternal toxicity in rats (body weight, food consumption, water consumption, and relative kidney weight) with a NOEL of 1126 mg/kg/day, and mice (relative kidney weight) with a NOEL of 5630 mg/kg/day. Developmental toxicity, expressed as fetotoxicity, had a NOEL of 5630 mg/kg/day with the rat and 563 mg/kg/day with mice. Neither species showed any evidence of embryotoxicity or teratogenicity. There was no evidence for reproductive toxicity with mice given up to 3% triethylene glycol in drinking water in a continuous breeding study. triethylene glycol did not produce mutagenic or clastogenic effects in the following in vitro genetic toxicology studies: Salmonella typhimurium reverse mutation test, SOS-chromotest in E. coli, CHO forward gene mutation test (HGPRT locus), CHO sister chromatid exchange test, and a chromosome aberration test with CHO cells. The use patterns suggest that exposure to triethylene glycol is mainly occupational, with limited exposures by consumers. Exposure is normally by skin and eye contact. Local and systemic adverse health effects by cutaneous exposure are likely not to occur, and eye contact will produce transient irritation without corneal injury. The very low vapor pressure of triethylene glycol makes it unlikely that significant vapor exposure will occur. Aerosol exposure is not a usual exposure mode, and acute aerosol exposures are unlikely to be harmful, although a peripheral sensory irritant effect may develop. However, repeated exposures to a triethylene glycol aerosol may result in respiratory tract irritation, with cough, shortness of breath and tightness of the chest. Recommended protective and precautionary measures include protective gloves, goggles or safety glasses and mechanical room ventilation. LC(50) data to various fish, aquatic invertebrates and algae, indicate that triethylene glycol is essentially nontoxic to aquatic organisms. Also, sustained exposure studies have demonstrated that triethylene glycol is of a low order of chronic aquatic toxicity. The bioconcentration potential, environmental hydrolysis, and photolysis rates are low, and soil mobility high. In the atmosphere triethylene glycol is degraded by reacting with photochemically produced hydroxyl radicals. These considerations indicate that the potential for ecotoxicological effects with triethylene glycol is low.
ENVIRONMENTAL FATE & EXPOSURE
Triethylene glycol's production and use a fragrance ingredient in cosmetics, as a solvent, plasticizer in vinyl, polyester and polyurethane resins, as a humectant in printing inks, and in the dehydration of natural gas may result in its release to the environment through various waste streams; triethylene glycol's use as a bacteriostat and as an inert ingredient to facilitate delivery of formulated pesticide products will result in its direct release to the environment. If released to air, a vapor pressure of 1.32X10-3 mm Hg at 25 °C indicates triethylene glycol will exist solely as a vapor in the atmosphere. Vapor-phase triethylene glycol 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 11 hours. Alcohols and ethers do not absorb light at wavelengths >290 nm and therefore triethylene glycol is not expected to be susceptible to direct photolysis by sunlight. If released to soil, triethylene glycol 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 3.2X10-11 atm-cu m/mole. River die-away test data demonstrate that biodegradation is likely to be the most important removal mechanism of triethylene glycol from aerobic soil and water; complete degradation in river die-away studies required 7-11 days. If released into water, triethylene glycol 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 triethylene glycol lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to triethylene glycol may occur through inhalation and dermal contact with this compound at workplaces where triethylene glycol is produced or used. Monitoring and use data indicate that the general population may be exposed to triethylene glycol via inhalation of ambient air, and dermal contact with products containing triethylene glycol.
