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Triethylene glycol bis(2-ethylbutyrate)

HCID 7217
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
95-08-9
Standard SMILES
CCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CC
InChIKey
JEYLQCXBYFQJRO-UHFFFAOYSA-N
Molecular formula
C18H34O6
Average molar mass
346.5 g/mol
Monoisotopic mass
346.23553881

Overview

Triethylene glycol di-(2-ethylbutyrate) is a light colored liquid. (USCG, 1999)

Names & identifiers

Preferred name
Triethylene glycol bis(2-ethylbutyrate)
IUPAC
2-[2-[2-(2-ethylbutanoyloxy)ethoxy]ethoxy]ethyl 2-ethylbutanoate
English name
TRIETHYLENE GLYCOL DI(2-ETHYLBUTYRATE)
Molecular formula
C18H34O6
Molecular weight
346.46

Names & synonyms

Plasticizer 3GH95-08-9Triglycol dihexoateTriglycol dicaproateTRIETHYLENE GLYCOL BIS(2-ETHYLBUTYRATE)Flexol plasticizer 3GHTriethylene glycol di-2-ethylbutyrateTriethyleneglycol diethyl butyrateTriethylene glycol di(2-ethyl butyrate)2,2'-(Ethylenedioxy)di(ethyl 2-ethylbutyrate)Triethylene glycol bis(2-ethyl butyrate)NSC 406329
Show more names
Flexol 3GHFlexol-3GHplasticizer3ghtriglycoldihexoatetriglycoldicaproateflexolplasticizer3gh
Triglycol di-(2-ethylbutyrate)2-Ethylbutyric acid, triethylene glycol diesterButyric acid, 2-ethyl-, diester with triethylene glycolHSDB 5285Triethylene glycol di-(2-ethylbutyrate)Triethylene glycol, bis(2-ethylbutyrate)OWT3WGI62I2-Ethylbutyric acid, diester with triethylene glycol

Database identifiers

CAS
95-08-9

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
71.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
17
Heavy atoms
24
Formal charge
0
Complexity
291

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Ethylene Glycols
Density · 3 items

0.9946 at 68 °F (USCG, 1999) - Less dense than water; will float

0.9946 @ 20 °C/20 °C

Bulk density = 8.3 lb/gal @ 20 °C

Viscosity10.3 CENTIPOISES @ 20 °C
Color/FormLIGHT-COLORED LIQUID
Solubility0.02% BY WT IN WATER @ 20 °C
Flash Point · 2 items

385 °F (USCG, 1999)

385 °F

Boiling Point>300 °C
Melting Point-10 °C
Vapor Pressure · 2 items

0.0000905 [mmHg]

5.8 MM HG @ 200 °C

Physical Description · 2 items

Triethylene glycol di-(2-ethylbutyrate) is a light colored liquid. (USCG, 1999)

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 ClassificationNot Classified

Hazard information

Regulatory InformationChemical: Butanoic acid, 2-ethyl-, 1,2-ethanediylbis(oxy-2,1-ethanediyl) ester
Fire HazardsSpecial Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire. (USCG, 1999)
Health HazardsExposure can cause irritation of eyes, nose and throat. (USCG, 1999)
Hazards SummaryIn lethal-dose feeding studies, causes somnolence and kidney changes; [RTECS] An eye, nose, and throat irritant; [CAMEO] May cause irritation; [MSDSonline] See Triethylene glycol.
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Reactivity Profile · 1 item

TRIETHYLENE GLYCOL DI-(2-ETHYLBUTYRATE) is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire (USCG, 1999).

Air and Water ReactionsHygroscopic. Water soluble.
Hazard Classes and Categories

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as plasticizer; [HSDB]

PLASTICIZER

General Manufacturing InformationButanoic acid, 2-ethyl-, 1,1'-[1,2-ethanediylbis(oxy-2,1-ethanediyl)] ester: ACTIVE

Applications

General DescriptionLight colored liquid.

Suppliers1 total

DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
7217
DTXSID
DTXSID80861696
UNII
OWT3WGI62I
EC Number
202-389-4
Nikkaji
J12.875I

Light colored liquid; [HSDB] Hygroscopic; [CAMEO] Fruity pleasant odor; [MSDSonline]

Other Experimental Properties196 °C @ 5 MM HG

Physicochemical properties

Melting point
-10 °C · -10 °C
Boiling point
401.18 °C · 401.18°C (rough estimate)
Density
0.995 · 0.9950
refractive index
1.445 · 1.4450 (estimate)
Henry's Law Constant
9.9 · 9.9×105 mol/(m3Pa) at 25℃, HSDB (2015)
EWG's Food Scores
1 · 1
FDA UNII
3 WGI62I · OWT3WGI62I
EPA Substance Registry System
Triethylene glycol bis(2-ethylbutyrate) (95-08-9)
TSCA
TSCA listed
Hazardous Substances Data
95 · 95-08-9(Hazardous Substances Data)
Not Classified

Safety & protection

Fire FightingFire Extinguishing Agents Not to Be Used: Water.
First AidCall for medical aid.
Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal Protective Equipment (PPE)Full impervious protective clothing, including boots and gloves. Where splashing is possible wear full face shield or chemical safety goggles. Use approved respirator to protect against vapors. (USCG, 1999)

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 240(SRC), determined from an experimental water solubility(2) and a recommended regression-derived equation(3), indicates that triethylene glycol bis(2-ethylbutyrate) will have moderate mobility in soil(SRC). Volatilization of triethylene glycol bis(2-ethylbutyrate) is not expected to be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1X10-11 atm-cu m/mole(SRC), using a recommended regression equation(4). Volatilization from dry soil surfaces(SRC) is not expected based on an estimated vapor pressure of 9X10-5 mm Hg(SRC), determined from a fragment constant method(5). According to a biodegradation study(6), triethylene glycol bis(2-ethylbutyrate) will biodegrade quickly in soil(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 240(SRC), determined from an experimental water solubility(2) and a recommended regression-derived equation(1), indicates that triethylene glycol bis(2-ethylbutyrate) may adsorb to suspended solids and sediment in the water(SRC). Triethylene glycol bis(2-ethylbutyrate) will be essentially non-volatile from water surfaces(1,SRC) based on an estimated Henry's Law constant of 1X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), an estimated BCF value of 31(1,SRC), from an experimental water solubility(2), suggests that bioconcentration in aquatic organisms is moderate, not high(SRC). Base-catalyzed hydrolysis half-lives for triethylene glycol bis(2-ethylbutyrate) have been estimated(SRC), through a structure estimation method(5), to be 2.9 years and 29 years at pHs of 8 and 7, respectively(5,SRC). According to a biodegradation study(6), triethylene glycol bis(2-ethylbutyrate) will biodegrade quickly in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethylene glycol bis(2-ethylbutyrate), which has an estimated vapor pressure of 9X10-5 mm Hg at 25 °C(2,SRC), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase triethylene glycol bis(2-ethylbutyrate) 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 about 10 hours(3,SRC). Particulate-phase triethylene glycol bis(2-ethylbutyrate) may be physically removed from the air by wet and dry deposition(SRC).

Soil Adsorption/Mobility · 1 item

The Koc of triethylene glycol bis(2-ethylbutyrate) is estimated as approximately 240(SRC), using an experimental water solubility of 200 mg/l(1,SRC) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that triethylene glycol bis(2-ethylbutyrate) has medium mobility in soil(SRC).

TSCA Test Submissions · 1 item

The acute inhalation toxicity of triethylene glycol di(2-ethylbutyrate) was evaluated in groups of six rats (strain not reported) receiving whole body exposure. Animals were exposed to the mist formed by bubbling a stream of air through test article at 170 degrees Celsius. The maximum and minimum periods of exposure resulting in no fatality and all animals dying were 15 and 30 minutes, respectively.

Artificial Pollution SourcesTriethylene glycol bis(2-ethylbutyrate)'s production and use as an plasticizer(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationA four week biodegradation study using 30 mg/l sludge and a triethylene glycol bis(2-ethylbutyrate) concentration of 100 mg/L gave 79-84% theoretical BOD(1).
Environmental Bioconcentration · 1 item

An estimated BCF value of 31 was calculated for triethylene glycol bis(2-ethylbutyrate)(SRC), using an experimental water solubility of 200 mg/l(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is moderate, not high(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for triethylene glycol bis(2-ethylbutyrate) is estimated as 1X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that triethylene glycol bis(2-ethylbutyrate) will be essentially nonvolatile from water surfaces(2,SRC). Triethylene glycol bis(2-ethylbutyrate)'s values for vapor pressure, 9X10-5 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces should not occur(SRC).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of triethylene glycol bis(2-ethylbutyrate) with photochemically produced hydroxyl radicals has been estimated as 3.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Base-catalyzed hydrolysis half-lives for triethylene glycol bis(2-ethylbutyrate) have been estimated(SRC), through a structure estimation method(2), to be 2.9 years and 29 years at pHs of 8 and 7, respectively(2,SRC).

Probable Routes of Human ExposureOccupational exposure may occur through inhalation and dermal contact with this compound at workplaces where triethylene glycol bis(2-ethylbutyrate) is produced and used. (SRC)
Environmental Fate/Exposure Summary · 1 item

Triethylene glycol bis(2-ethylbutyrate)'s production and use as an plasticizer may result in its release to the environment through various waste streams. If released to soil, triethylene glycol bis(2-ethylbutyrate) will have moderate mobility based on an estimated Koc value of 240. Volatilization of triethylene glycol bis(2-ethylbutyrate) should not be important from moist soil surfaces given an estimated Henry's Law constant of 1X10-11 atm-cu m/mole. Volatilization from dry soil surfaces is not expected either based on an estimated vapor pressure of 9X10-5 mm Hg. According to a biodegradation study, triethylene glycol bis(2-ethylbutyrate) will biodegrade quickly in soil and water. If released to water, triethylene glycol bis(2-ethylbutyrate) may adsorb to suspended solids and sediment. Triethylene glycol bis(2-ethylbutyrate) will be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 1X10-11 atm-cu m/mole. An estimated BCF value of 31 suggests that bioconcentration in aquatic organisms is moderate, not high. Triethylene glycol bis(2-ethylbutyrate) has estimated based-catalyzed hydrolysis half-lives of 2.9 years at a pH of 8 and 29 years at a pH of 7. If released to the atmosphere, triethylene glycol bis(2-ethylbutyrate), which has an estimated vapor pressure of 9X10-5 mm Hg, will exist in both the vapor and particulate phases. Vapor-phase triethylene glycol bis(2-ethylbutyrate) is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 10 hours. Particulate-phase triethylene glycol bis(2-ethylbutyrate) may be physically removed from the air by wet and dry deposition. Occupational exposure may occur through inhalation and dermal contact with this compound at workplaces where triethylene glycol bis(2-ethylbutyrate) is produced and used. (SRC)

Safety data

tsca
TSCA listed
Hazardous Substances Data
95-08-9(Hazardous Substances Data)