Basic information
- Standard SMILES
CCCCOCCOCCOCCO- InChIKey
COBPKKZHLDDMTB-UHFFFAOYSA-N- Molecular formula
- C10H22O4
- Average molar mass
- 206.28 g/mol
- Monoisotopic mass
- 206.15180918
Overview
Triethylene glycol monobutyl ether is a poly(ethylene glycol).
Names & identifiers
- Preferred name
- Triethylene glycol monobutyl ether
- IUPAC
- 2-[2-(2-butoxyethoxy)ethoxy]ethanol
- English name
- Butoxytriethylene glycol
- Molecular formula
- C10H22O4
- Molecular weight
- 206.28
Names & synonyms
Show more names
Database identifiers
- CAS
143-22-6- PubChem CID
- 8923
- DTXSID
DTXSID7021520- ChEMBL
CHEMBL3184092- ChEBI
CHEBI:231291- UNII
- OC116GRO69
- EC Number
- 205-592-6
- Nikkaji
- J52.422K
Properties
Computed structural properties
- XLogP
- 0.4
- Topological polar surface area
- 47.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 11
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 98.1
Experimental & physicochemical properties
Density
0.9890 g/cu cm at 20 °C
Relative density (water = 1): 0.98 (25 °C)
Solubility
Very soluble in ethanol, methanol
Miscible with water.
Solubility in water: miscible
Flash Point
290 °F (143 °C) (CLOSED CUP)
143 °C c.c.
Physicochemical properties
- Melting point
- -35 °C · -35 °C
- Boiling point
- 278 °C · 278 °C
- Density
- 0.989 g/cm3 · 0.9890 g/cm3
- pka
- 14.36 · 14.36±0.10(Predicted)
Safety & regulation
GHS classification
GHS Classification
Danger
H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]
P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for < 0.1% (2 of 3582) of reports.
Danger
H318 (> 99.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
Hazard information
Regulatory Information
Chemical: Ethanol, 2-[2-(2-butoxyethoxy)ethoxy]-
Ethanol, 2-[2-(2-butoxyethoxy)ethoxy]- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-[2-(2-butoxyethoxy)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: 21-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14102
Ethanol, 2-[2-(2-butoxyethoxy)ethoxy]-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards Summary
High-dose animal studies: Not genotoxic; Doses >1000 mg/kg/day cause liver injury; Repeated oral doses >4000 mg/kg/day cause testicular injury; Not a developmental toxin at doses <1000 mg/kg/day; No deaths after inhalation of saturated solution for 8 hours; [OECD SIDS: High Boiling Ethylene Glycol Ethers - 2002] An eye and mild skin irritant; [ICSC] In lethal-dose animal studies after oral administration, causes flaccid paralysis; [RTECS] A strong eye irritant, based on animal studies; [HSDB] A mild to moderate skin irritant; Very irritating to eyes; [eChemPortal: SIDSUNEP] May cause serious eye injury; [eChemPortal: ESIS] See GLYCOL ETHERS.
TSCA Requirements
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 monobutyl ether is included on this list.
A testing consent order is in effect for triethylene glycol monobutyl ether for health effects testing. FR citation: January 9, 1989.
NFPA Hazard Classification
2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.
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.
Hazard Classes and Categories
Eye Dam. 1 (> 99.9%)
Eye damage - category 1
Serious eye damage/eye irritation - Category 2A
Serious eye damage/eye irritation - Category 1
Eye Dam. 1
Safety & protection
First Aid Measures
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.
Rinse mouth.
Disposal Methods
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.
Spillage Disposal
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Wash away remainder with plenty of water.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Toxicology
Ecotoxicity Values
LC50 Leuciscus idus /(Ide)/ >2150 and <4640 mg/L; 96hr; static bioassay (purity of test compound 87.2%)
LC50 Pimephales promelas /(Fathead minnow)/ 2400 mg/L/96 hr; static bioassay (also 24 hr and 48 hr)
LC50 Poecilia reticulata /(Guppy)/ 197 mg/L/7 days; semi-static bioassay
LC50 Daphnia magna (Water flea) 2210 mg/L/48 hr; static bioassay
Environmental Fate
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 monobutyl ether is expected to have very high mobility in soil(SRC). Volatilization of triethylene glycol monobutyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.5X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Triethylene glycol monobutyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.5X10-3 mm Hg(4). The theoretical BODs for triethylene glycol monobutyl ether are 0, 5, and 24% for 5, 10 and 20 days, respectively(5), suggesting that triethylene glycol monobutyl ether is expected to biodegrade slowly 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 monobutyl 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 9.5X10-14 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 0.02(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The theoretical BODs for triethylene glycol monobutyl ether are 0, 5 and 24% for 5, 10 and 20 days, respectively(8), triethylene glycol monobutyl ether is expected to biodegrade slowly in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethylene glycol monobutyl ether, which has a vapor pressure of 2.5X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethylene glycol monobutyl 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 7.5 hours(SRC), calculated from its rate constant of 5.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Alcohols and ethers do not contain chromophores that absorb at wavelengths >290 nm and therefore triethylene glycol monobutyl ether is not expected to be susceptible to direct photolysis by sunlight(4).
Toxicity Summary
The CIR Expert Panel concluded that the following butyl polyoxyalkylene ethers safe in the present practices of use and concentration in cosmetics when formulated to be non-irritating...Buteth-3...
Safe for use in cosmetics, with qualifications
Signs and Symptoms
Redness. Dry skin.
Redness. Pain.
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of triethylene glycol monobutyl ether can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that triethylene glycol monobutyl ether is expected to have very high mobility in soil(SRC).
TSCA Test Submissions
Acute oral toxicity was evaluated in groups of 10 male albino Wistar rats administered single doses of Poly Solv TB (triethylene glycol monobutyl ether) by oral gavage atlevels of 3.2, 5.0, 7.73, and 12.18 g/kg body weight. Mortality was observed in 6 animals in the 5.0 g/kg dose group, 8 animals in the 7.73 g/kg dose group, and all animals in the highest dose group. The LD50 value was calculated to be 5.3 g/kg (4.1 to 6.8 g/kg 95% confidence limits) by the Litchfield and Wilcoxon method. Clinical observations included loss of righting reflex and flaccid muscle tone in the 5.0 g/kg dose group, flaccid muscle tone, heavy breathing and coma in the 7.73 g/kg dose group, and death within 3 hours in the highest dose group. Gross necropsy was not reported.
Acute oral toxicity was evaluated in groups of 6 male rats (strain not reported) administered single doses of undiluted Dowanol TBH (triethylene glycol monobutyl ether) at levels of 0.5, 1.0, 2.0, and 3.98 g/kg body weight. Mortality was observed in 3 animals in the 3.98 g/kg dose group; an LD50 value was not reported. Clinical and gross necropsy findings were not reported.
Acute oral toxicity was evaluated in groups of 5 male Dow-Wistar albino rats administered single doses of undiluted butoxy triglycol by oral gavage at levels of 4.0, 8.0, and 16.0 ml/kg of body weight. Mortality was observed in 1 animal in the 4.0 ml/kg dose group, 3 animals in the 8.0 ml/kg dose group and in all animals in the highest dose group. The LD50 value was calculated by the moving average method to be 6.73 ml/kg (4.13 to 10.96 ml/kg). Clinical observations were not reported. Gross necropsy evaluation revealed congestion of abdominal viscera and lungs.
Acute dermal toxicity was evaluated in 10 New Zealand white rabbits (sex not reported) receiving single occluded applications of Poly Solv TB (triethylene glycol monobutyl ether) at a dose level of 2.0 g/kg body weight. The test article was held in contact with abraded skin for a 24 hour period. Mortality was not observed in any animal; an LD50 value was not reported. The observation period was uneventful and gross necropsy was not reported.
For more TSCA Test Submissions (Complete) data for TRIETHYLENE GLYCOL MONOBUTYL ETHER (9 total), please visit the HSDB record page.
Artificial Pollution Sources
Triethylene glycol monobutyl ether's production and use as a plasticizer intermediate(1), a solvent for cellulose nitrate, cellulose ethers, chlorinated rubber, poly(vinyl acetate), colophony, many other natural and synthetic resins, stoving chemicals, wood paints, pharmaceutical and cosmetic preparations, as well as drying greases and oils(3), as a solubilizer for mutually incompatible liquids(3), in the production of household and metal cleansing agents as well as for wood preservation(3), in cutting and hydraulic oils, production of inks(3), as a leveling agent(3), in the leather auxiliaries industry(3), and in the chemical, textile, and transportation industries(2) may result in its release to the environment through various waste streams(SRC).
Regulatory information
TSCA Requirements
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 monobutyl ether is included on this list.
A testing consent order is in effect for triethylene glycol monobutyl ether for health effects testing. FR citation: January 9, 1989.
Chemistry & industry
Pharmacology
Absorption, Distribution and Excretion
Human abdominal whole skin (2.54 cm sq) was mounted in a glass diffusion apparatus (at 30 +/- 1 degree C) and the diffusion of triethylene glycol monobutyl ether was monitored during a 12-hr period using gas chromatography (n=6). The integrity of the epidermal membranes was first assessed by measuring permeability of membranes to tritiated water. Epidermal membranes displaying permeability constants greater than 1.5 x 10E-3 cm/hr were deemed to have been damaged during preparation and were rejected. The mean steady state of absorption for triethylene glycol monobutyl ether was 22.2 ug/cm sq/hr (SD +/- 8.59), which was 100-fold less than that of ethylene glycol monomethyl ether. Test material did not increase permeability of the membrane (damage ratio of 1.26).
Uses & manufacturing
Uses
CIR ingredient: Buteth-3
Used as plasticizer, intermediate, and solvent (resins, paints, metal cleansing agents, pharmaceuticals, cosmetics, greases, and oils) ; Also used in wood preservatives, cutting and hydraulic oils, inks, and in the leather, textile, and transportation industries; [HSDB] Used mainly in automotive hydraulic brake fluids; Also used as a solvent and intermediate; [eChemPortal: SIDSUNEP]
Metal Degreasing [Category: Clean]
Plasticizer, intermediate
CHEM INT FOR REACTION PRODUCTS WITH ALUMINUM ISOPROPOXIDE
Solvent for cellulose nitrate, cellulose ethers, chlorinated rubber, poly(vinyl acetate), colophony, many other natural and synthetic resins, stoving chemicals, wood paints, pharmaceutical and cosmetic preparations, as well as drying greases and oils, as a solubilizer for mutually incompatible liquids, in the production of household and metal cleansing agents as well as for wood preservation, in cutting and hydraulic oils, production of Indian inks, writing inks, and ballpoint pen pastes, as a leveling agent, and in the leather auxiliaries industry.
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) No Data
(1981) No Data
U.S. Production
2023: 40,000,000 - <55,000,000 lb
(1979) 4.52X10+9 GRAMS
(1981) 3.56X10+9 GRAMS
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5480]
(2006): 1,612 million lb annual capacity /Glycol ethers/
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).
Methods of Manufacturing
REACTION OF ETHYLENE OXIDE WITH ETHYL ALCOHOL (PRODUCT IS ISOLATED FROM THE RESULTANT MIXTURE OF ETHYL ETHERS OF GLYCOLS BY VACUUM DISTILLATION)
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. /Ethylene Glycol Monoethers/
General Manufacturing Information
Wholesale and Retail Trade
Ethanol, 2-[2-(2-butoxyethoxy)ethoxy]-: ACTIVE
Suppliers50 total
Related reactions
Linked notes
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