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フタル酸ビス(2-ブトキシエチル)

Bis(2-butoxyethyl) phthalate

HCID 8345
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
117-83-9
標準SMILES
CCCCOCCOC(=O)c1ccccc1C(=O)OCCOCCCC
InChIKey
CMCJNODIWQEOAI-UHFFFAOYSA-N
分子式
C20H30O6
平均分子量
366.4 g/mol
単同位体質量
366.20423868

概要

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.

名称と識別子

優先名称
Bis(2-butoxyethyl) phthalate
IUPAC
bis(2-butoxyethyl) benzene-1,2-dicarboxylate
現地名
フタル酸ビス(2-ブトキシエチル)
英語名
Bis(2-n-butoxyethyl)phthalate
分子式
C20H30O6
分子量
366.45

名称と別名

BIS(2-BUTOXYETHYL) PHTHALATEPalatinol KKesscoflex BCPKronisolKesscoflexPlasthall DBEPButyl glycol phthalateBis(2-butoxyethyl)phthalateDibutylglycol phthalateDibutoxyethyl phthalateDibutyl cellosolve phthalateDi(butoxyethyl)phthalate
名称をさらに表示
フタル酸ビス(2-ブトキシエチル)サンソサイザーC-1100ケスコフレックスBCPパラチノールKプラスタールDBEPビス(2-ブトキシエチル)=フタラートフタル酸ジ(2-ブトキシエチル)クロニソールブチルグリコールフタラートフタル酸ジ‐2‐N‐ブトキシエチル標準品フタル酸ビス (2-ブトキシエチル)1,2-ビス(2-ブトキシエチル) ベンゼン-1,2-ジカルボキシラートフタル酸ジ-2-n-ブトキシエチル標準品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

データベース識別子

CAS
117-83-9
PubChem CID
8345
DTXSID
DTXSID9047174
ChEMBL
CHEMBL3182679
ChEBI
CHEBI:79937
UNII
N3MI1R200O
EC Number
204-213-1
Nikkaji
J47.944F

物性

構造計算による物性

XLogP
4.4
極性表面積
71.1 Ų
水素結合供与体数
0
水素結合受容体数
6
回転可能結合数
16
重原子数
26
形式電荷
0
複雑度
348

実験および物理化学的性質

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

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 件

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.
Melting PointFP: -55 °C
Vapor Pressure0.00217 [mmHg]
Refractive IndexRefractive index = 1.486 at 20 °C/D.

物理化学的性質

融点
-54.9 °C · -54.9°C
沸点
270 °C · 270 °C / 22mmHg
比重(密度)
1.06 · 1.06
屈折率
20 · n20/D 1.486(lit.)
闪点
205 °C · 205 °C
貯蔵温度
Refrigerator
溶解性
クロロホルム(微量)、メタノール(微量)
外見
油
色
無色
水溶解度
0.3 g/L · <0.3g/L(20℃)
Henry's Law Constant
4.9 · 4.9×106 mol/(m3Pa) at 25℃, HSDB (2015)
LogP
4.52 · 4.520 (est)
CAS データベース
117 · 117-83-9(CAS DataBase Reference)
EPAの化学物質情報
Bis(2-butoxyethyl) phthalate (117-83-9)

化学的性質

化学的特性The empirical formula of dibutoxyethyl phthalate (DBEP) is C20H30O6. It is a colorless liquid, with a density of 1.063.It is soluble in organic solvents and fairly insoluble in water.

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 3 件

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.

危険有害性情報

Regulatory Information · 2 件

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 件

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 件

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 件

Bis(2-n-butoxyethyl) phthalate

D: Other compounds that may form peroxides

Kelly

Hazard Classes and CategoriesNot Classified

安全と保護具

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

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 件

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.

毒性情報

Environmental Fate · 3 件

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 件

/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 件

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 件

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 件

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 件

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 件

/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 件

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 件

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)

法規制情報

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

安全データ

tsca
TSCA listed
rtecs
TI0175000
毒性
LD50 orl-rat: 8380 mg/kg JIHTAB 30,63,48
hs_code
2917.39.7000
化審法
(3)-2962
消防法
危-4-4-III
有毒物質データの
117-83-9(Hazardous Substances Data)

化学と産業

用途と製造

Uses · 6 件

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 件

(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

応用分野

用途フタル酸ビス(2-ブトキシエチルは、軟質塩ビ全般に可塑剤として使用されます。 また分子内にエーテル結合を有するので、多くの樹脂材料、ゴム材料と相溶し、樹脂改質剤として使用されます。

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

調製方法

DBEP is formed by the esterification of glycol monobutyl ether with phthalic anhydride in the presence of a catalyst (sulfuric acid or p-toluenesulfonic acid) or noncatalytically at high temperature.

上流・下流製品情報

上流原料

フタル酸無水物ジエチレン グリコール モノ-n-ブチル エーテル

サプライヤー100 社

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補足説明

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

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化合物ノート

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