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アジピン酸ジエチル

Diethyl Adipate

HCID 8844
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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
141-28-6
標準SMILES
CCOC(=O)CCCCC(=O)OCC
InChIKey
VIZORQUEIQEFRT-UHFFFAOYSA-N
分子式
C10H18O4
平均分子量
202.25 g/mol
単同位体質量
202.12050906

概要

Diethyl adipate is a fatty acid ester.

名称と識別子

優先名称
Diethyl Adipate
IUPAC
diethyl hexanedioate
現地名
アジピン酸ジエチル
英語名
Diethyl adipate
分子式
C10H18O4
分子量
202.25

名称と別名

DIETHYL ADIPATE141-28-6Diethyl hexanedioateEthyl adipate1,6-Diethyl hexanedioateHexanedioic acid, diethyl esterAdipic acid, diethyl esterHexanedioic acid, 1,6-diethyl esterHexanedioic acid, diethyl-Diethylester kyseliny adipoveNSC 19160Ethyl delta-carboethoxyvalerate
名称をさらに表示
アジピン酸ジエチルアジピン酸エチルブタン-1,4-ジカルボン酸ジエチルジエチル=アジパートヘキサン二酸ジエチルジエチルアジペ-トアジピン酸ジエチル, 99%1,6-ジエチル ヘキサンジオアートDiethyl adipatateNSC 3363DiethyleadipateETHYL ADIPATE (DI)Diethyl adipate,99%
DUB DEAHSDB 5413AI3-00342EINECS 205-477-0Diethylester kyseliny adipove [Czech]BRN 17800357B19K45L6CNSC-19160

データベース識別子

CAS
141-28-6、68201-71-8
PubChem CID
8844
DTXSID
DTXSID2021999
ChEBI
CHEBI:34697
UNII
7B19K45L6C
EC Number
205-477-0
Nikkaji
J5.805J

物性

構造計算による物性補完中

XLogP
1.3
極性表面積
52.6 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
9
重原子数
14
形式電荷
0
複雑度
157

実験および物理化学的性質

Chemical ClassesOther Classes -> Esters, Other
CosmeticsCosmetic ingredients (Diethyl Adipate) -> CIR (Cosmetic Ingredient Review)
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Diethyl hexanedioate) -> IFRA transparency List
PlasticizersPlasticizer
Density1.0076 @ 20 °C
Flavoring AgentsEU Flavoring substances
Color/FormColorless liquid
Solubility · 2 件

Soluble in ethanol and ethyl ether

In water, 4230 mg/l @ 20 °C

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point245 °C
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.

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 100% (95 of 95) of all reports.

Not Classified

Aggregated GHS information provided per 95 reports by companies from 1 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 4 件

Chemical: Hexanedioic acid, 1,6-diethyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 10-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/16772

Hexanedioic acid, diethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Hazards SummaryOral LD50 (mouse) = 8100 mg/kg; [RTECS] An irritant; [MSDSonline]
Hazard Classes and CategoriesNot Classified

安全と保護具

Disposal Methods · 1 件

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.

毒性情報

Environmental Fate

化学と産業

用途と製造

Uses · 6 件

CIR ingredient: Diethyl Adipate

Used as plasticizer and chemical intermediate; [HSDB]

Plasticizer

CHEM INT FOR ADIPIC ACID ESTERS BY TRANSESTERIFICATION

PLASTICIZER FOR CELLULOSE POLYMERS, EG, CELLULOSE ACETATE

CHEM INT FOR CYCLOPENTANONE

U.S. Production · 2 件

(1979) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.

(1981) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.

Methods of ManufacturingESTERIFICATION OF ADIPIC ACID WITH ETHYL ALCOHOL
Use ClassificationFragrance Ingredients
General Manufacturing Information · 2 件

Hexanedioic acid, 1,6-diethyl ester: ACTIVE

Hexanedioic acid, diethyl-: INACTIVE

応用分野 · 5 件

用途有機合成原料。

説明Diethyl adipate (DEA) is a green organic solvent that can be used as a separating agent to extract various alcohols, such as methanol, ethanol and propanol, from aqueous solutions. DEA is also frequently employed in studies of saponification reactions with sodium hydroxide solutions during distillation processes.

使用Diethyl adipate is occasionally used in perfumery as a solvent fixative. Has been used in flavor compositions, mainly as a solvent, modifier, blender or fixative. It has not much of a distinct character, but acts mostly softening, mellowing upon an established flavor composition.

使用Diethyl adipate(DEA) is an organic solvent that can be used in organic synthesis, plasticizer, polymer and fragrance synthesis. DEA can also be used in the synthesis of hexanediol and oligoadipamide, which can be layered with perfluoropolyether networks for protective coating applications.

一般的な説明Diethyl adipate (DEA), a fatty ester, is processed from the esterification of adipic acid and ethanol. It can be used as a plasticizer.

関連反応

11 件
反応記録を作成
HRID 376496 の反応式
HRID 376496反応物としてuspto-grants-2000_02
HRID 381238 の反応式
HRID 381238反応物としてuspto-grants-2001_10
HRID 484923 の反応式
HRID 484923溶媒としてuspto-grants-1985_08
HRID 719851 の反応式
HRID 719851反応物としてuspto-grants-2006_11
HRID 816571 の反応式
HRID 816571反応物としてTest data from https://doi.org/10.1039/C8SC04228D
HRID 1125167 の反応式
HRID 1125167反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (7/10)
HRID 1283766 の反応式
HRID 1283766生成物としてuspto-grants-1976_08
HRID 1838515 の反応式
HRID 1838515反応物としてuspto-grants-2004_01
1 / 2 ページ

化合物ノート

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物理化学的性質

融点
-20 · -20--19 °C (lit.)
沸点
251 °C · 251 °C (lit.)
比重(密度)
1.009 g/mL · 1.009 g/mL at 25 °C (lit.)
屈折率
20 · n20/D 1.427(lit.)
闪点
230 °F · >230 °F
貯蔵温度
30 °C · Store below +30°C.
溶解性
0.1 g/l · <0.1g/l
外見
液体
色
無色透明
臭い (Odor)
Pleasant, rather powerful odor of vinousoily-slightly fruity character
由来生物
synthetic
水溶解度
水に不溶。
Merck
14 · 14,162
BRN
1780035 · 1780035
Henry's Law Constant
2.7 · 2.7×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
主な用途
フレーバーそして香料
化粧品成分の機能
香料スキンコンディショニング皮膚コンディショニング剤 - 保湿剤
InChI
1S/C10H18O4/c1-3-13-9(11)7-5-6-8-10(12)14-4-2/h3-8H2,1-2H3
InChIKey
VIZORQUEIQEFRT-UHFFFAOYSA-N
SMILES
CCOC(=O)CCCCC(=O)OCC
LogP
2.37 · 2.370 (est)
表面張力
32.7 mN/m · 32.7mN/m at 293.15K
CAS データベース
141 · 141-28-6(CAS DataBase Reference)
NISTの化学物質情報
Hexanedioic acid, diethyl ester(141-28-6)
EPAの化学物質情報
Hexanedioic acid, diethyl ester (141-28-6)

化学的性質

化学的特性Clear Colorless oily liquid. Soluble in ethanol and other organic solvents, insoluble in water.

· 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 45(SRC), determined from a water solubility of 4,230 mg/l at 20 °C(2) and a regression-derived equation(3), indicates that diethyl adipate is expected to have very high mobility in soil(SRC). Volatilization of diethyl adipate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.6X10-6 atm-cu m/mole(SRC), from a vapor pressure of 0.058 mm Hg(4) and its water solubility(2). Volatilization from dry soil surfaces is not expected to be an important environmental fate process based on the vapor pressure(4). Diethyl adipate was degraded to adipic acid using an activated sludge inoculum(5), suggesting biodegradation may be an important fate process in soils(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 45(SRC), determined from a water solubility of 4,230 mg/l at 20 °C(2) and a regression-derived equation(3), indicates that diethyl adipate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.6X10-6 atm-cu m/mole(SRC), from a vapor pressure of 0.058 mm Hg(4) and its water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 10 and 110 days, respectively(SRC). A base-catalyzed second-order hydrolysis rate constant of 0.12 L/mole-sec(SRC) was estimated using a structure estimation method(5); this corresponds to half-lives of 1.7 years and 64 days at pH values of 7 and 8, respectively(5). Diethyl adipate was degraded to adipic acid using an activated sludge inoculum(6), suggesting biodegradation may be an important fate process in water(SRC). According to a classification scheme(7), an estimated BCF of 6(SRC), from its water solubility and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethyl adipate, which has a vapor pressure of 0.058 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethyl 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 2 days(SRC), calculated from its estimated rate constant of 7.8X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Diethyl adipate may also undergo direct photolysis in the environment since this compound contains functional groups that can absorb light greater than 290 nm(4).

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Soil Adsorption/Mobility · 1 件

The Koc of diethyl adipate is estimated as 45(SRC), using a water solubility of 4,230 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diethyl adipate is expected to have very high mobility in soil(SRC).

Human Toxicity ExcerptsDIETHYL ADIPATE...IS OF RELATIVELY LOW TOXICITY.
Artificial Pollution SourcesDiethyl adipate's production and use as a plasticizer(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationDiethyl adipate was degraded to adipic acid using an activated sludge inoculum(1).
Environmental Bioconcentration · 1 件

An estimated BCF of 6 was calculated for diethyl adipate(SRC), using a water solubility of 4,230(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 diethyl adipate is estimated as 3.6X10-6 atm-cu m/mole(SRC) from its vapor pressure, 0.058 mm Hg(1), and water solubility, 4,230 mg/l(2). This Henry's Law constant indicates that diethyl adipate is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 10 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 110 days(SRC). Diethyl adipate's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC). Volatilization from dry soil surfaces is not expected to be an important environmental fate process for diethyl adipate(SRC) based on its vapor pressure(1).

Non-Human Toxicity Excerpts · 5 件

DERMAL IRRITATION SLIGHT. /FROM TABLE/

SINGLE IP DOSES OF DIETHYL ADIPATE GIVEN TO MALE MICE MATED WITH UNTREATED VIRGIN FEMALES PRODUCED DOSE-DEPENDENT ANTIFERTILITY & DOMINANT LETHAL MUTAGENIC EFFECTS, AS INDICATED BY REDUCED PERCENTAGE OF PREGNANCIES & INCR NUMBER OF EARLY FETAL DEATHS. MUTATIONAL EFFECTS OCCURRED MAINLY DURING POSTMEIOTIC STAGE OF SPERMATOGENESIS.

SEVEN ADIPATES INCL DIETHYL ADIPATE WERE EVALUATED FOR THEIR EMBRYONIC-FETAL TOXICITY & TERATOGENIC EFFECTS IN RATS. THE ADIPATES APPEAR TO BE LESS TERATOGENIC THAN PHTHALATES WHEN ADMIN DURING GESTATION IN EQUIVALENT FRACTIONS OF RESPECTIVE LD50 DOSES.

Alkyloxy adipates are slightly more toxic than the parent hydrocarbon esters. ... It is possible that the ether linkage increases its toxicity toward the hepatic system, or ethylene glycol may be formed metabolically, which might affect the renal and, to a lesser extent, the hepatic system. /Alkyloxy adipates/

Moderately toxic by intraperitoneal route. Experimental reproductive effects. Mutation data reported.

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of diethyl adipate with photochemically-produced hydroxyl radicals has been estimated as 7.8X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.12 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 1.7 years and 64 days at pH values of 7 and 8, respectively(2). Diethyl adipate may also undergo direct photolysis in the environment since this compound contains functional groups that can absorb light greater than 290 nm(3).

Probable Routes of Human ExposureOccupational exposure to diethyl adipate may occur through inhalation and dermal contact with this compound at workplaces where diethyl adipate is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 件

Diethyl adipate's production and use as a plasticizer may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.058 mm Hg at 25 °C indicates diethyl adipate will exist solely as a vapor in the ambient atmosphere. Vapor-phase diethyl 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 2 days. Diethyl adipate may undergo direct photolysis in the environment, but the kinetics of this reaction are unknown. If released to soil, diethyl adipate is expected to have very high mobility based upon an estimated Koc of 45. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 3.6X10-6 atm-cu m/mole. Volatilization from dry soil surfaces is not expected to be an important environmental fate process based on the vapor pressure of this compound. Diethyl adipate was degraded to adipic acid using an activated sludge inoculum in a single screening study. If released into water, diethyl adipate is not expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 10 and 110 days, respectively. Hydrolysis may be an important environmental fate process based on estimated hydrolysis half-lives of 64 days and 1.7 years at pH 8 and 7, respectively. An estimated BCF of 6 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to diethyl adipate may occur through inhalation and dermal contact with this compound at workplaces where diethyl adipate is produced or used. (SRC)

安全データ

wgk
2
tsca
TSCA listed
rtecs
AV1100000
hs_code
29171290
化審法
(2)-861, (2)-879
消防法
危-4-3-III
safety_code
24/25
ストレージクラス
10 - Combustible liquids
有毒物質データの
141-28-6(Hazardous Substances Data)

上流・下流製品情報

上流原料

アジピン酸エタノールシクロヘキサン硫酸水素

下流製品

シクロペンタノン-2-カルボン酸エチルキナクリドンN,N-DIPHENYLQUINACRIDONEPigment Red 1227-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-oneN,N'-ジメチルキナクリドン (D2687の精製品)アジピン酸 モノエチル2-ヒドロキシシクロペンタンカルボン酸エチル