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Bis(2-(2-butoxyethoxy)ethyl) adipate

HCID 8836
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
141-17-3
Standard SMILES
CCCCOCCOCCOC(=O)CCCCC(=O)OCCOCCOCCCC
InChIKey
SCABKEBYDRTODC-UHFFFAOYSA-N
Molecular formula
C22H42O8
Average molar mass
434.6 g/mol
Monoisotopic mass
434.28796829

Names & identifiers

Preferred name
Bis(2-(2-butoxyethoxy)ethyl) adipate
IUPAC
bis[2-(2-butoxyethoxy)ethyl] hexanedioate
English name
Bis[2-(2-butoxyethoxy)ethyl] adipate
Molecular formula
C22H42O8
Molecular weight
434.56

Names & synonyms

Bis[2-(2-butoxyethoxy)ethyl] adipate141-17-3WareflexDibutoxyethoxyethyl adipatePlasthall DBEEAPlasthall 226SAdipic acid, bis(2-(2-butoxyethoxy)ethyl) esterBIS(2-(2-BUTOXYETHOXY)ETHYL) ADIPATEReomol BCDTP-95Bisoflex 111Thiokol TP 95
Show more names
BXAtp759BIS(BUTOXYETHOXYETHYL)ADIPATEdyscmzrx11806reomolbcdthiokoltp95bisoflex111
Thiokol TP 759Hexanedioic acid, bis[2-(2-butoxyethoxy)ethyl] esterHSDB 5480EINECS 205-465-5TP 759Adipic acid bis(diethylene glycol monobutyl ether) esterBRN 1808453RX 11806

Database identifiers

CAS
141-17-3
PubChem CID
8836
DTXSID
DTXSID3027085
ChEMBL
CHEMBL2132625
UNII
O955C8WB42
EC Number
205-465-5
Nikkaji
J45.502D

Properties

Computed structural propertiesFilling in

XLogP
2.5
Topological polar surface area
89.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
8
Rotatable bonds
25
Heavy atoms
30
Formal charge
0
Complexity
353

Experimental & physicochemical properties

Boiling Point240 °C @ 5 mm Hg
Melting Point-47 °C
Vapor Pressure0.0000001 [mmHg]
Physical Description · 2 items

Liquid

Insoluble in water; [ChemIDplus]

Collision Cross Section · 1 item

198.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3027085];205.4 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3027085];203.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID3027085]

Physicochemical properties

Melting point
11 °C · −11 °C(lit.)
Boiling point
467.61 °C · 467.61°C (rough estimate)
Density
1.01 g/mL · 1.01 g/mL at 25 °C(lit.)

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 · 3 items

This chemical does not meet GHS hazard criteria for 98.6% (138 of 140) of all reports.

Not Classified;Reported as not meeting GHS hazard criteria by 138 of 140 companies (only 1.4% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

Aggregated GHS information provided per 140 reports by companies from 4 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 138 of 140 reports by companies.;There are 2 notifications provided by 2 of 140 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 3 items

Chemical: Hexanedioic acid, 1,6-bis[2-(2-butoxyethoxy)ethyl] ester

Hexanedioic acid, 1,6-bis[2-(2-butoxyethoxy)ethyl] ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanedioic acid, 1,6-bis[2-(2-butoxyethoxy)ethyl] ester 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: 25-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12122

Hazards SummaryMay cause irritation; [MSDSonline]
Hazard Classes and CategoriesNot Classified

Safety & protection

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used as a plasticizer and softener for natural and synthetic rubbers; [HSDB]

Plasticizer-eg, for cellulose nitrate and polyvinyl acetate

PLASTICIZER & SOFTENER FOR NATURAL & SYNTHETIC RUBBERS

U.S. Production · 3 items

2023: 1,000,000 - <2,500,000 lb;2022: 2,500,000 - <4,000,000 lb;2021: 4,000,000 - <5,500,000 lb;2020: 1,000,000 - <5,000,000 lb

(1979) PROBABLY GREATER THAN 9.08X10+6 GRAMS

(1981) PROBABLY GREATER THAN 9.08X10+6 GRAMS

Consumer UsesPlasticizer;Solvent
Industry UsesSolvent;Processing aids not otherwise specified;Plasticizer;Intermediate
Methods of ManufacturingREACTION OF 2-(2-BUTOXYETHOXY)ETHANOL WITH ADIPIC ACID
Use Classification · 2 items

Plastics -> Polymer Type -> N.a.

Plastics -> Plasticisers

General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing;Textiles, apparel, and leather manufacturing;Plastics Material and Resin Manufacturing;Adhesive Manufacturing;Synthetic Rubber Manufacturing;Rubber Product Manufacturing

Hexanedioic acid, 1,6-bis[2-(2-butoxyethoxy)ethyl] ester: ACTIVE

Applications

UsesPlasticizer

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Related reactions

1 records
New reaction record
HRID 1196072 reaction equation
HRID 1196072As productuspto-grants-1992_05

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
refractive index
20 · n20/D 1.448(lit.)
Flash point
230 °F · >230 °F
form
liquid
Water Solubility
570 mg/L · 570mg/L at 20℃
Henry's Law Constant
3.2 · 3.2×107 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
InChI=1S/C22H42O8/c1-3-5-11-25-13-15-27-17-19-29-21(23)9-7-8-10-22(24)30-20-18-28-16-14-26-12-6-4-2/h3-20H2,1-2H3
InChIKey
SCABKEBYDRTODC-UHFFFAOYSA-N
SMILES
C(OCCOCCOCCCC)(=O)CCCCC(OCCOCCOCCCC)=O
LogP
3.24 · 3.24
Indirect Additives used in Food Contact Substances
DIBUTOXYETHOXYETHYL ADIPATE
FDA 21 CFR
177.26 · 177.2600
EWG's Food Scores
1 · 1
FDA UNII
955 C8WB42 · O955C8WB42
EPA Substance Registry System
2 · Bis[2-(2-butoxyethoxy)ethyl] adipate (141-17-3)
UNSPSC Code
12162002 · 12162002
NACRES
23 · NA.23
Safety Statements
24 · 24/25
WGK Germany
2 · 2
RTECS
8420000 · AU8420000
TSCA
TSCA listed
HS Code
29171900 · 29171900
Storage Class
10 · 10 - Combustible liquids
Hazardous Substances Data
141 · 141-17-3(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: 6gm/kg
REACH Registrations
Active
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.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,400(SRC), determined from an estimated log Kow of 3.24(2,SRC) and a regression-derived equation(3), indicates that bis(2-(2-butoxyethoxy)ethyl) adipate is expected to have low mobility in soil(SRC). Volatilization of bis(2-(2-butoxyethoxy)ethyl) adipate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Bis(2-(2-butoxyethoxy)ethyl) adipate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.8X10-8 mm Hg(SRC), determined from a fragment constant method(5). Bis(2-(2-butoxyethoxy)ethyl) adipate, present at 100 mg/l, achieved 86 percent of its theoretical BOD in 4 weeks using an activated sludge inoculum(6), suggesting this compound may biodegrade in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,400(SRC), determined from an estimated log Kow of 3.24(2,SRC) and a regression-derived equation(3), indicates that bis(2-(2-butoxyethoxy)ethyl) adipate is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected to be an important fate process(3) based upon an estimated Henry's Law constant of 3.1X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). A base-catalyzed second-order hydrolysis rate constant of 0.27 L/mole-sec(SRC) was estimated using a structure estimation method(5); this corresponds to half-lives of 294 and 29 days at pH values of 7 and 8, respectively(5). According to a classification scheme(6), an estimated BCF of 62(SRC), from an estimated log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Bis(2-(2-butoxyethoxy)ethyl) adipate, present at 100 mg/l, achieved 86 percent of its theoretical BOD in 4 weeks using an activated sludge inoculum(8), suggesting this compound may biodegrade in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(2-(2-butoxyethoxy)ethyl) adipate, which has an estimated vapor pressure of 9.8X10-8 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bis(2-(2-butoxyethoxy)ethyl) adipate 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 5 hours(SRC), calculated from its rate constant of 7.4X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). Bis(2-(2-butoxyethoxy)ethyl) adipate may also undergo direct photolysis in the environment since this compound contains a functional group that can absorb light greater than 290 nm(4). Particulate-phase bis(2-(2-butoxyethoxy)ethyl) adipate may be removed from the air by wet and dry deposition(SRC).

Soil Adsorption/Mobility · 1 item

The Koc of bis(2-(2-butoxyethoxy)ethyl) adipate is estimated as 1,400(SRC), using an estimated log Kow of 3.24(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that bis(2-(2-butoxyethoxy)ethyl) adipate is expected to have low mobility in soil(SRC).

Artificial Pollution SourcesBis(2-(2-butoxyethoxy)ethyl) adipate's production and use as a plasticizer(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationBis(2-(2-butoxyethoxy)ethyl) adipate, present at 100 mg/l, reached 86 percent of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1), suggesting biodegradation is rapid.
Environmental Bioconcentration · 1 item

An estimated BCF of 62 was calculated for bis(2-(2-butoxyethoxy)ethyl) adipate(SRC), using an estimated log Kow of 3.24(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for bis(2-(2-butoxyethoxy)ethyl) adipate is estimated as 3.1X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bis(2-(2-butoxyethoxy)ethyl) adipate is expected to be essentially nonvolatile from water surfaces(2). Bis(2-(2-butoxyethoxy)ethyl) adipate's estimated Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected(SRC). Volatilization from dry soil surfaces is not expected to be an important environmental fate process given an estimated vapor pressure of 9.8X10-8 mm Hg at 25 °C(3).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of bis(2-(2-butoxyethoxy)ethyl) adipate with photochemically-produced hydroxyl radicals has been estimated as 7.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.27 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 294 and 29 days at pH values of 7 and 8, respectively(2). Bis(2-(2-butoxyethoxy)ethyl) adipate may also undergo direct photolysis in the environment since this compound contains a functional group that can absorb light greater than 290 nm(3).

Probable Routes of Human Exposure · 1 item

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,476 workers (75 of these are female) are potentially exposed to bis(2-(2-butoxyethoxy)ethyl) adipate in the US(1). Occupational exposure to bis(2-(2-butoxyethoxy)ethyl) adipate may occur through inhalation and dermal contact with this compound at workplaces where bis(2-(2-butoxyethoxy)ethyl) adipate is produced or used(SRC).

Environmental Fate/Exposure Summary · 1 item

Bis(2-(2-butoxyethoxy)ethyl) adipate's production and use as a plasticizer may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 9.8X10-8 mm Hg at 25 °C indicates bis(2-(2-butoxyethoxy)ethyl) adipate will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bis(2-(2-butoxyethoxy)ethyl) adipate 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 5 hours. Bis(2-(2-butoxyethoxy)ethyl) adipate may also undergo direct photolysis in the environment, but the kinetics of this reaction are unknown. Particulate-phase bis(2-(2-butoxyethoxy)ethyl) adipate will be removed from the atmosphere by wet and dry deposition. If released to soil, bis(2-(2-butoxyethoxy)ethyl) adipate is expected to have low mobility based upon an estimated Koc of 1,400. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 3.1X10-13 atm-cu m/mole. Bis(2-(2-butoxyethoxy)ethyl) adipate is not expected to volatilize from dry soil surfaces based on its vapor pressure. Bis(2-(2-butoxyethoxy)ethyl) adipate, achieved 86 percent of its theoretical BOD in 4 weeks using an activated sludge inoculum, suggesting this compound may biodegrade in the environment. If released into water, bis(2-(2-butoxyethoxy)ethyl) adipate is expected to adsorb to suspended solids and sediment in water 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. Hydrolysis may be an important environmental fate process based on estimated hydrolysis half-lives of 29 and 294 days at pH 8 and 7, respectively. An estimated BCF of 62 suggests the potential for bioconcentration in aquatic organisms is moderate. Occupational exposure to bis(2-(2-but

Regulatory information

Regulatory Information · 3 items

Chemical: Hexanedioic acid, 1,6-bis[2-(2-butoxyethoxy)ethyl] ester

Hexanedioic acid, 1,6-bis[2-(2-butoxyethoxy)ethyl] ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanedioic acid, 1,6-bis[2-(2-butoxyethoxy)ethyl] ester 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: 25-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12122

Safety data

wgk
2
tsca
TSCA listed
rtecs
AU8420000
hs_code
29171900
Toxicity
LD50 oral in rat: 6gm/kg
safety_code
24/25
Storage Class
10 - Combustible liquids
REACH Registrations
Active
Hazardous Substances Data
141-17-3(Hazardous Substances Data)