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Bis(2-butoxyethyl) phthalate

HCID 8345
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Grundinformationen

CAS
117-83-9
Standard-SMILES
CCCCOCCOC(=O)c1ccccc1C(=O)OCCOCCCC
InChIKey
CMCJNODIWQEOAI-UHFFFAOYSA-N
Summenformel
C20H30O6
Durchschnittliche Molmasse
366,4 g/mol
Monoisotopische Masse
366,20423868

Überblick

Bis(2-butoxyethyl)phthalate is a phthalate ester obtained by the formal condensation of both the carboxy groups of phthalic acid with two molecules of 2-butoxyethanol. It has a role as a xenobiotic. It is a phthalate ester and a diester. It is functionally related to a 2-butoxyethanol.

Namen und Bezeichner

Bevorzugter Name
Bis(2-butoxyethyl) phthalate
IUPAC
bis(2-butoxyethyl) benzene-1,2-dicarboxylate
Englischer Name
Bis(2-n-butoxyethyl)phthalate
Summenformel
C20H30O6
Molmasse
366.45

Namen und Synonyme

BIS(2-BUTOXYETHYL) PHTHALATEPalatinol KKesscoflex BCPKronisolKesscoflexPlasthall DBEPButyl glycol phthalateBis(2-butoxyethyl)phthalateDibutylglycol phthalateDibutoxyethyl phthalateDibutyl cellosolve phthalateDi(butoxyethyl)phthalate
Weitere Namen anzeigen
DBEPNSC 4840palatinolkStaflex DBEPPlasthall 200plasthalldbepkesscoflexbcp
N-Butyl glycol phthalateKronisol (VAN)dibutoxyethylphthalatePhthalic acid dibutoxy ethyl esterDibutylcellosolve ftalatDi(butoxyethyl) phthalate1,2-Benzenedicarboxylic acid, 1,2-bis(2-butoxyethyl) esterPhthalic acid, bis(2-butoxyethyl) ester

Datenbank-Bezeichner

CAS
117-83-9
PubChem CID
8345
DTXSID
DTXSID9047174
ChEMBL
CHEMBL3182679
ChEBI
CHEBI:79937

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,4
Polarare Oberfläche (TPSA)
71,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
16
Schwere Atome
26
Formalladung
0
Komplexität
348

Experimentelle und physikochemische Eigenschaften

PolymersPlastics & Rubber -> Phthalate Esters
Density1.06 at 20 °C
Viscosity42 mPa sec at 20 °C.
Color/FormColorless liquid
Solubility · 3 Einträge

Phthalate esters are soluble to various extents in many common organic solvents and oils, but have a relatively low solubility in water. /Phthalate esters/

Soluble in organic solvents

In water, 300 mg/L, temp not specified

Flash Point · 2 Einträge

407 °F; 208 °C (CLOSED CUP)

407 °F (208 °C) (Open cup)

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point270 °C
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 3 Einträge

This chemical does not meet GHS hazard criteria for 98.3% (114 of 116) of all reports.

Not Classified

Aggregated GHS information provided per 116 reports by companies from 3 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: 1,2-Benzenedicarboxylic acid, bis(2-butoxyethyl) ester

1,2-Benzenedicarboxylic acid, bis(2-butoxyethyl) ester: 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.

Fire PotentialCombustible
Hazards SummaryLike dioctyl phthalate, it may cause CNS depression and mild liver toxicity after ingestion of large amounts; [HSDB] May cause irritation; [MSDSonline] See PHTHALATE ESTERS.
FDA RequirementsDi(butoxyethyl) phthalate is an indirect food additive for use only as a component of adhesives.
Special Reports · 5 Einträge

Nat'l Research Council Canada; Phthalate Esters in the Aquatic Environment (1980) NRCC No. 17583

USEPA; Ambient Water Quality Criteria Doc: Phthalate Esters (1980) EPA 440/5-80-067

Woodward KN (ed); Phthalate Esters: Toxicity and Metabolism (1988)

Phthalate Esters; Environ Health Perspect 45: 1-210 (1982)

For more Special Reports (Complete) data for BIS(2-BUTOXYETHYL) PHTHALATE (6 total), please visit the HSDB record page.

NFPA Hazard Classification · 3 Einträge

Chemie und Industrie

Verwendung und Herstellung

Uses · 6 Einträge

Used as plasticizer for polyvinyl chloride, polyvinyl acetate, cellulosic, and other resins; Also used as a softener and processing aid for chloroprene rubber, nitrile-butadiene rubber, and styrene-butadiene rubber; [HSDB]

... Plasticizers for cellulosic resins and some vinyl ester resins.

Plasticizer for polyvinyl chloride, polyvinyl acetate, and other resins

PLASTICIZER, EG, FOR CELLULOSIC, VINYL & ACRYLIC RESINS

SOFTENER & PROCESSING AID FOR CHLOROPRENE RUBBER

For more Uses (Complete) data for BIS(2-BUTOXYETHYL) PHTHALATE (6 total), please visit the HSDB record page.

U.S. Production · 3 Einträge

(1979) PROBABLY GREATER THAN 2.27X10+6 G

(1981) PROBABLY GREATER THAN 2.27X10+6 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5391]

Methods of ManufacturingEthylene glycol monobutyl ether + phthalic anhydride (esterification)
General Manufacturing Information1,2-Benzenedicarboxylic acid, 1,2-bis(2-butoxyethyl) ester: ACTIVE

Anwendungen

VerwendenIt is used as a plasticizer for polyvinyl chloride, polyvinyl acetate, and other resins.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

PhthalsureanhydridDiethylene glycol monobutyl ether

Anbieter100 Anbieter

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
UNII
N3MI1R200O
EC Number
204-213-1
Nikkaji
J47.944F
Melting Point
FP: -55 °C
Vapor Pressure0.00217 [mmHg]
Refractive IndexRefractive index = 1.486 at 20 °C/D.

Physikochemische Eigenschaften

Schmelzpunkt
-54.9 °C · -54.9°C
Siedepunkt
270 °C · 270 °C / 22mmHg
Dichte
1.06 · 1.06
Brechungsindex
20 · n20/D 1.486(lit.)
Flammpunkt
205 °C · 205 °C
storage temp.
Refrigerator
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand
Oil
Farbe
Colourless
Wasserlöslichkeit
0.3 g/L · <0.3g/L(20 ºC)
Henry's Law Constant
4.9 · 4.9×106 mol/(m3Pa) at 25℃, HSDB (2015)
LogP
4.52 · 4.520 (est)
CAS Datenbank
117 · 117-83-9(CAS DataBase Reference)
EPA chemische Informationen
Bis(2-butoxyethyl) phthalate (117-83-9)

1 - Materials that, under emergency conditions, can cause significant irritation.

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.

Peroxide Forming Chemical · 3 Einträge

Bis(2-n-butoxyethyl) phthalate

D: Other compounds that may form peroxides

Kelly

Hazard Classes and CategoriesNot Classified

Sicherheit und Schutzausrüstung

Fire Fighting ProceduresAlcohol foam. Water or foam may cause frothing.
Disposal Methods · 1 Eintrag

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.

Preventive Measures · 1 Eintrag

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a structure estimation method(2), indicates that bis(2-butoxyethyl) phthalate is expected to have moderate mobility in soil(SRC). Volatilization of bis(2-butoxyethyl) phthalate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Bis(2-butoxyethyl) phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.2X10-3 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation studies using a series of commercial phthalate esters and acclimated inoculum have demonstrated that in general, phthalate esters may be susceptible to biodegradation(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a structure estimation method(2), indicates that bis(2-butoxyethyl) phthalate is 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 2.0X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 27(SRC), from an estimated log Kow of 4.06(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 1.3 years and 49 days at pHs 7 and 8, respectively(8). Biodegradation studies using a series of commercial phthalate esters and acclimated inoculum have demonstrated that, in general, phthalate esters may be susceptible to biodegradation(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(2-butoxyethyl) phthalate, which has an estimated vapor pressure of 2.2X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase bis(2-butoxyethyl) phthalate 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 9.1 hours(SRC), calculated from its rate constant of 4.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase bis(2-butoxyethyl) phthalate may be removed from the air by wet or dry deposition(SRC). Bis(2-butoxyethyl) phthalate does contain chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ecotoxicity Excerpts · 1 Eintrag

/AQUATIC SPECIES/ Inhibitory effect of 18 phthalic acid esters (1-200 ug/mL) on Tetrahymena pyriformis was investigated. Cytostatic toxicity occurred with those having alkyl chain C1-C8 in alcohol moiety. Dibutoxyethyl phthalate was moderately toxic.

Effluent ConcentrationsBis(2-butoxyethyl) phthalate was not detected in 4 domestic sewages, 6 domestic sewages with storm runoff and small industrial effluent and 2 domestic sewage with storm runoff and large industrial effluent(1).
Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc of bis(2-butoxyethyl) phthalate can be estimated to be 170(SRC). According to a classification scheme(2), this estimated Koc value suggests that bis(2-butoxyethyl) phthalate is expected to have moderate mobility in soil.

Artificial Pollution SourcesBis(2-butoxyethyl) phthalate's production and use as a plasticizer for polyvinyl chloride, polyvinyl acetate, and other resins(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 Eintrag

AEROBIC: Bis(2-butoxyethyl) phthalate, present at 3,000 ppm, exhibited a biodegradation half-life of 10 days at 30 °C using the soil microbe Pseudomonas acidovorans 256-1, in media containing 6,000 ppm phthalate esters(1). Biodegradation studies using a series of commercial phthalate esters and acclimated inoculum have demonstrated that in general, phthalate esters may be susceptible to biodegradation(2). A proposed pathway is via enzymatic ester hydrolysis to form the monoester and corresponding alcohol; further enzymatic degradation of the monoester proceeds via phthalic acid to procatechuate, ultimately yielding acetyl CoA and succinate(3).

Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 27 was calculated in fish for bis(2-butoxyethyl) phthalate(SRC), using an estimated log Kow of 4.06(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for bis(2-butoxyethyl) phthalate is estimated as 2.0X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bis(2-butoxyethyl) phthalate is expected to be essentially nonvolatile from water surfaces(2). Bis(2-butoxyethyl) phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.2X10-3 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5 Einträge

/LABORATORY ANIMALS: Acute Exposure/ Rats inhaling 290 ppm over a 6-hr period showed no adverse effects.

/LABORATORY ANIMALS: Acute Exposure/ Application of DBEP to rabbit skin causes slight irritation. Instillation of 500 mg into rabbit eyes causes mild irritation.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... Relatively well tolerated when fed in diet of rats for 30 day period at ... up to 0.5 g/kg/day. At higher levels, such as 1.7 g/kg/day, some reduced growth, appetite, and histological changes were noted.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Dibutoxyethyl /phthalate/ ... injected into the yolk at 2.5 to 3 days of incubation was associated with cranial bifida and anophthalmia /in chick embryos/.

For more Non-Human Toxicity Excerpts (Complete) data for BIS(2-BUTOXYETHYL) PHTHALATE (9 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 Eintrag

The rate constant for the vapor-phase reaction of bis(2-butoxyethyl) phthalate with photochemically-produced hydroxyl radicals has been estimated as 4.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9.1 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.16 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 1.3 years and 49 days at pH values of 7 and 8, respectively(2). Bis(2-butoxyethyl) phthalate does contain chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human Exposure · 1 Eintrag

Occupational exposure to bis(2-butoxyethyl) phthalate may occur through inhalation of aerosols and dermal contact with this compound at workplaces where bis(2-butoxyethyl) phthalate is produced or used. Use data indicate that the general population may be exposed to bis(2-butoxyethyl) phthalate via products containing this compound. (SRC)

Regulatorische Informationen

FDA RequirementsDi(butoxyethyl) phthalate is an indirect food additive for use only as a component of adhesives.

Sicherheitsdaten

tsca
TSCA listed
hs_code
2917.39.7000
RTECS-Nr.
TI0175000
Toxizität
LD50 orl-rat: 8380 mg/kg JIHTAB 30,63,48
Giftige Stoffe Daten
117-83-9(Hazardous Substances Data)
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Ergänzende Hinweise

DefinitionChEBI: A phthalate ester obtained by the formal condensation of both the carboxy groups of phthalic acid with two molecules of 2-butoxyethanol.