HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

Triethylene glycol monobutyl ether

HCID 8923
New noteNew reactionRequest quotes
Print preview

Completing data — refresh the page later to see the latest

Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
143-22-6
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

TRIETHYLENE GLYCOL MONOBUTYL ETHER143-22-6Butoxytriglycol2-[2-(2-Butoxyethoxy)ethoxy]ethanolButyltriglycolEthanol, 2-[2-(2-butoxyethoxy)ethoxy]-2-(2-(2-Butoxyethoxy)ethoxy)ethanolDTXSID7021520HSDB 5645EINECS 205-592-6UNII-OC116GRO69BRN 1750600
Show more names
OC116GRO69Ethanol, 2-(2-(2-butoxyethoxy)ethoxy)-AI3-30236BUTETH-3PEG-3 BUTYL ETHERNSC-164915DTXCID701520EC 205-592-6

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 propertiesFilling in

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

SolventsSolvents -> Glycol Ethers (E Series)
CosmeticsCosmetic ingredients (Buteth-3) -> CIR (Cosmetic Ingredient Review)
SpringerMaterials PropertiesDielectric constant
PesticidesPesticide -> EPA IRIS
SurfactantsSurfactant
LogP0.02
OdorMild smelling
Density · 2 items

0.9890 g/cu cm at 20 °C

Relative density (water = 1): 0.98 (25 °C)

Viscosity9.2 centistokes at 25 °C
Color/FormColorless liquid
Solubility · 3 items

Very soluble in ethanol, methanol

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

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 · 4 items

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.

Other Safety InformationIMAP assessments - Ethanol, 2-[2-(2-butoxyethoxy)ethoxy]-: Human health tier II assessment
Fire HazardsCombustible.
Fire PotentialCombustible
Hazards Summary · 1 item

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.

Chemistry & industry

Pharmacology

Absorption, Distribution and Excretion · 1 item

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 · 6 items

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 · 2 items

(1979) No Data

(1981) No Data

U.S. Imports · 2 items

Related reactions

12 records
New reaction record
HRID 2535 reaction equation
HRID 2535As reactantuspto-grants-1998_03
HRID 126969 reaction equation
HRID 126969As reactantuspto-grants-1981_03
HRID 480386 reaction equation
HRID 480386As reactantuspto-grants-2003_11
HRID 601957 reaction equation
HRID 601957As reactantuspto-grants-2011_03
HRID 611960 reaction equation
HRID 611960As reactantuspto-grants-1999_12
HRID 895800 reaction equation
HRID 895800As reactantuspto-grants-2005_07
HRID 1052337 reaction equation
HRID 1052337As productuspto-grants-2016_07
HRID 1355304 reaction equation
HRID 1355304As reactantuspto-grants-2003_07
Page 1 of 2

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes

Miscible with water.

Solubility in water: miscible

Flash Point · 2 items

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)
EC ClassificationSymbol: Xi; R: 41; S: (2)-26-39-46
TSCA Requirements · 2 items

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 · 3 items

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 · 5 items

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

Explosive Limits and PotentialExplosive limits , vol% in air: 0.8-3.8
Skin, Eye, and Respiratory IrritationsFound to be highly irritating in the rabbit eye in two separate studies.Rabbit eyes were necrosed by instillation of 0.02 mL. Minor to moderate injury resulted from instillation of 0.005 mL.
Hazardous Reactivities and IncompatibilitiesGlycol ethers, glycols, ketones, and alcohols undergo violent decomposition in contact with 68-72% perchloric acid

Safety & protection

Fire FightingUse water spray, powder, alcohol-resistant foam, carbon dioxide.
First Aid Measures · 4 items

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 · 1 item

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 · 1 item

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 · 1 item

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.

Eye PreventionWear safety goggles.
Fire PreventionNO open flames.
Inhalation RiskA harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse ventilation.
Effects of Long Term ExposureThe substance defats the skin, which may cause dryness or cracking.

Toxicology

Ecotoxicity Values · 4 items

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 · 3 items

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).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol.
Toxicity Summary · 2 items

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 · 2 items

Redness. Dry skin.

Redness. Pain.

Effluent ConcentrationsTriethylene glycol monobutyl ether has been identified in the effluents from the following industries: paint and ink (3438 ng/uL extract), printing and publishing (3868 ng/uL extract), and organic chemicals (160 ng/uL extract)(1).
EPA IRIS InformationTriethylene glycol monobutyl ether
Soil Adsorption/Mobility · 1 item

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 · 5 items

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 · 1 item

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).

Environmental BiodegradationAEROBIC: The theoretical BODs for triethylene glycol monobutyl ether are 0, 5, and 24% for 5 days, 10 days, and 20 days, respectively, indicating that it will be partially removed from biological wastewater treatment plants(1).

Regulatory information

TSCA Requirements · 2 items

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.

(1979) No Data

(1981) No Data

U.S. Production · 6 items

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).

Consumer UsesHydraulic fluids
Industry UsesOther
Methods of Manufacturing · 3 items

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/

Household ProductsInformation on 58 consumer products that contain Butoxytriglycol in the following categories is provided:
General Manufacturing Information · 2 items

Wholesale and Retail Trade

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