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アゼライン酸ビス(2-エチルヘキシル)

Bis(2-ethylhexyl) azelate

HCID 7642
ノート反応
基本情報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
部分構造検索類似構造を探す

基本情報

CAS
103-24-2
標準SMILES
CCCCC(CC)COC(=O)CCCCCCCC(=O)OCC(CC)CCCC
InChIKey
ZDWGXBPVPXVXMQ-UHFFFAOYSA-N
分子式
C25H48O4
平均分子量
412.6 g/mol
単同位体質量
412.35526001

名称と識別子

優先名称
Bis(2-ethylhexyl) azelate
IUPAC
bis(2-ethylhexyl) nonanedioate
現地名
アゼライン酸ビス(2-エチルヘキシル)
英語名
AZELAIC ACID DI(2-ETHYLHEXYL) ESTER
分子式
C25H48O4
分子量
412.65

名称と別名

103-24-2Bis(2-ethylhexyl) azelatebis(2-ethylhexyl) nonanedioateAzelaic Acid Di(2-ethylhexyl) EsterTruflex DOXStaflex DOXPlastolein 9058Sansocizer DOZNonanedioic acid, bis(2-ethylhexyl) esterPlastolein 9058DOZEmery 2958Di(2-ethylhexyl) azelate
名称をさらに表示
アゼライン酸ビス(2-エチルヘキシル)プラストレイン9058アゼライン酸ジ(2-エチルヘキシル)スタフレックスDOXプラストレイン9058DOZノナン二酸ビス(2-エチルヘキシル)トルフレックスDOXジ(2-エチルヘキシル)ノナンジオアートアゼライン酸ジ-2-エチルヘキシルビス(2エチルヘキシル)アゼレートアゼライン酸ジ2エチルヘキシルアゼライン酸ジ-(2-エチルヘキシル)ビス(2-エチルヘキシル)=アゼラートノナン二酸ビス(2-エチルヘキシル)(DOZ)アゼライン酸ビス (2-エチルヘキシル)1,9-ビス(2-エチルヘキシル) ノナンジオアートDOZDIOCTYL AZELATEstaflexdoxtruflexdoxKodaflex DOZoctylazelate
DI-2-ETHYLHEXYL AZELATEEmolien 2986Plastolein 9058 DOZAzelaic acid, bis(2-ethylhexyl) esterUNII-5D67SBH6QBAzelaic acid, di(2-ethylhexyl)ester5D67SBH6QBMFCD00040496

データベース識別子

CAS
103-24-2
PubChem CID
7642
DTXSID
DTXSID3026697
ChEMBL
CHEMBL3183250
UNII
5D67SBH6QB
EC Number
203-091-7
Nikkaji
J47.118F

物性

構造計算による物性

XLogP
8.5
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
22
重原子数
29
形式電荷
0
複雑度
358

実験および物理化学的性質

OdorOdorless
PlasticizersPlastics & Rubber -> Other Plasticizers
Density0.915 @ 25 °C/4 °C
Color/FormColorless liquid
SolubilityInsol in water; sol in ethanol, acetone, benzene
Boiling Point237 °C @ 5 mm Hg
Melting Point-78 °C
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Refractive IndexIndex of refraction: 1.446 @ 25 °C/D
Physical Description · 2 件

Liquid

Colorless odorless liquid; [HSDB] Clear liquid with a mild odor; [HallStar MSDS]

Collision Cross Section222.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3026697]

物理化学的性質

融点
-67 °C · -67°C
沸点
282 °C · >282°C
比重(密度)
0 · 0,92 g/cm3
Pour Point
-76 · -76
屈折率
1.446 · 1.4460 (estimate)
闪点
211 °C · 211 °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
無色透明~淡黄色
水溶解度
0.1 mg/L · 0.1mg/L(25℃)
Henry's Law Constant
8.2 · 8.2×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
化粧品成分の機能
乳化安定剤皮膚コンディショニング剤 - 保湿剤ヘアコンディショニングスリップ修飾子皮膚コンディショニング - 保湿剤フィルム形成
LogP
9.213 · 9.213 (est)
CAS データベース
103 · 103-24-2(CAS DataBase Reference)
EPAの化学物質情報
Bis(2-ethylhexyl) azelate (103-24-2)

化学的性質

化学的特性It is a high-boiling point liquid (237°C at 5 mmHg) that is soluble in alcohol, acetone, and benzene and 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 · 5 件

This chemical does not meet GHS hazard criteria for 100% (76 of 76) of all reports.

Not Classified

Aggregated GHS information provided per 76 reports by companies from 1 notifications to the ECHA C&L Inventory.

Not Classified

Not Classified

危険有害性情報

Regulatory Information · 4 件

Chemical: Nonanedioic acid, bis(2-ethylhexyl) ester

Nonanedioic acid, 1,9-bis(2-ethylhexyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Nonanedioic acid, 1,9-bis(2-ethylhexyl) 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)

REACH registered substance: Bis(2-ethylhexyl) azelate (EC: 203-091-7)

Nonanedioic acid, bis(2-ethylhexyl) ester: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

A mild skin irritant; [RTECS] Azelate esters generally exhibit very low toxicity; External application to rabbit eyes scored 1 on a scale of 1-10 (10 being most severe) for degree of injury after 24 hours; [HSDB] May cause mild eye irritation; Inhalation may cause dizziness; [HallStar MSDS]

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 · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 300,000(SRC), determined from a structure estimation method(2), indicates that di-2-ethylhexyl azelate is expected to be immobile in soil(SRC). Volatilization of di-2-ethylhexyl azelate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, volatilization from moist soil surfaces is expected to be attenuated by adsorption. Di-2-ethylhexyl azelate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.8X10-6 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 300,000(SRC), determined from an estimation method(2), indicates that di-2-ethylhexyl azelate is 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 1.2X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 22 hours and 17 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 27 years, if adsorption is considered(8). Di-2-ethylhexyl azelate is expected to undergo hydrolysis producing 2-ethylhexanol and nonanedioic acid(SRC). An estimated hydrolysis rate constant of 0.07 L/mole-sec corresponds to half-lives of 3.2 years and 120 days at pH values of 7 and 8, respectively(9). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 9.6(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), di-2-ethylhexyl azelate, which has an estimated vapor pressure of 3.8X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase di-2-ethylhexyl azelate 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 13 hours(SRC), calculated from its rate constant of 3X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). Particulate-phase di-2-ethylhexyl azelate may be removed from the air by wet and dry deposition(SRC). Di-2-ethylhexyl azelate may undergo direct photolysis in the environment, since this compound contains a functional group that can absorb light >290 nm(4).

Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc for di-2-ethylhexyl azelate can be estimated to be 300,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that di-2-ethylhexyl azelate is expected to be immobile in soil.

Atmospheric ConcentrationsINDOOR AIR: Di-2-ethylhexyl azelate was detected in air samples collected from telephone office sites in Wichita, KS; Lubbock, TX; Newark, NJ; Stoughton, WI; Neenah, WI; Moberly, MO at a typical concentration of 10.0 ng/cu m(1).
Human Toxicity ExcerptsTHESE ESTERS HAVE VERY LOW ORDER OF TOXICITY. /AZELATE ESTERS/
Artificial Pollution SourcesDi-2-ethylhexyl azelate's production and use as a plasticizer for vinyls, a low-temperature plasticizer and also a base for synthetic lubricants(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 件

An estimated BCF of 3.2 was calculated for di-2-ethylhexyl azelate(SRC), using an estimated log Kow of 9.6(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 low.

Volatilization from Water/Soil · 1 件

The Henry's Law constant for di-2-ethylhexyl azelate is estimated as 1.2X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that di-2-ethylhexyl azelate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1m/sec, wind velocity of 3 m/sec)(2) is estimated as 22 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 17 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 27 years, if adsorption is considered(4). Di-2-ethylhexylazelate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC), however this process is expected to be attenuated by adsorption. Di-2-ethylhexyl azelate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.8X10-6 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity ExcerptsRATED 1 ON RABBIT EYES (SCALE 1-10, 10= MOST SEVERE INJURY OBSERVED AFTER 24 HR).
Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of di-2-ethylhexyl azelate with photochemically-produced hydroxyl radicals has been estimated as 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 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Di-2-ethylhexyl azelate is expected to undergo hydrolysis producing 2-ethylhexanol and nonanedioic acid(SRC). A base-catalyzed second-order hydrolysis rate constant of 0.07 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 3.2 years and 120 days at pH values of 7 and 8, respectively(2). Di-2-ethylhexyl azelate may undergo direct photolysis in the environment, since this compound contains a functional group that can absorb light >290 nm(3).

Probable Routes of Human Exposure · 1 件

NIOSH (NOES Survey 1981-1983) has statistically estimated that 17,011 workers (3,762 of these are female) are potentially exposed to di-2-ethylhexyl azelate in the US(1). Occupational exposure to di-2-ethylhexyl azelate may occur through inhalation and dermal contact with this compound at workplaces where di-2-ethylhexyl azelate is produced or used(SRC).

Environmental Water Concentrations · 1 件

DRINKING WATER: Di-2-ethylhexyl azelate was detected by GC/MS analysis, but not quantified, in 15 drinking water samples collected from Cincinnati, OH, Miami, FL, New Orleans, LA, Ottumwa, IA, Philadelphia, PA, and Seattle, WA; and also in 16 advanced waste treatment plant samples collected from Escondido, Lake Tahoe, Orange County, and Pomona (all in California), Dallas, TX, and Washington, D.C. (Blue Plains State)(1).

Environmental Fate/Exposure Summary · 1 件

Di-2-ethylhexyl azelate's production and use as a plasticizer for vinyls, a low-temperature plasticizer and also a base for synthetic lubricants may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 3.8X10-6 mm Hg at 25 °C indicates di-2-ethylhexyl azelate will exist in both the vapor and particulate phases. Vapor-phase di-2-ethylhexyl azelate 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 13 hours. Particulate-phase di-2-ethylhexyl azelate will be removed from the atmosphere by wet and dry deposition. Di-2-ethylhexyl azelate may undergo direct photolysis in the environment, since this compound contains a functional group that can absorb light >290 nm. If released to soil, di-2-ethylhexyl azelate is expected to be immobile based upon an estimated Koc of 300,000. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 1.2X10-4 atm-cu m/mole, however this process is expected to be attenuated by adsorption. If released into water, di-2-ethylhexyl azelate is 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 22 hours and 17 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 27 years, if adsorption is considered. Di-2-ethylhexyl azelate is expected to undergo hydrolysis producing 2-ethylhexanol and nonanedioic acid. An estimated hydrolysis rate constant of 0.07 L/mole-sec corresponds to half-lives of 3.2 years and 120 days at pH values of 7 and 8, respectively. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to di-2-ethylhexyl azelate may occur through inhalation and dermal contact with this compound at workplaces where di-2-ethylhexyl azelate is produced or used. (SRC)

安全データ

tsca
TSCA listed
rtecs
CM2000000
hs_code
29171390
化審法
(2)-879
消防法
危-4-4-III
有毒物質データの
103-24-2(Hazardous Substances Data)

化学と産業

用途と製造

Uses · 4 件

Used as plasticizer for cellulosics, polystyrene, and vinyl plastics and as a base for synthetic lubricants; [HSDB] Used to formulate metalworking fluid concentrates and lubricant additives-lubricants-greases; [ExPub: ECHA REACH Registrations] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]

Metal Machining [Category: Heat or Machine]

PLASTICIZER FOR CELLULOSICS, POLYSTYRENE & VINYL PLASTICS

Plasticizer for vinyls, especially used as low-temperature plasticizer; base for synthetic lubricants.

U.S. Production · 3 件

2023: 2,500,000 - <4,000,000 lb

(1972) 5.15X10+9 G

(1975) PROBABLY GREATER THAN 1.36X10+6 G

Consumer UsesPlasticizer
Industry UsesSolvent
Methods of ManufacturingREACTION OF AZELAIC ACID WITH 2-ETHYLHEXYL ALCOHOL IN THE PRESENCE OF AN ACID CATALYST
Formulations/PreparationsGrade: 99% pure
General Manufacturing Information · 3 件

Petroleum Lubricating Oil and Grease Manufacturing

Nonanedioic acid, 1,9-bis(2-ethylhexyl) ester: ACTIVE

PLASTICIZERS ARE MIXED INTO POLYMERS TO INCR FLEXIBILITY & WORKABILITY. ...AZELATE ESTERS ARE...COMMONLY USED, ESPECIALLY WHEN LOW-TEMP FLEXIBILITY IS DESIRED. /AZELATE ESTERS/

応用分野

用途塩ビ樹脂?合成ゴムの耐寒性可塑剤、合成潤滑油

使用It is used as a plasticizer.

調製方法

Di(2-ethylhexyl) azelate is manufactured by reacting 2- ethylhexanol with azelaic acid in the presence of an acid catalyst.

上流・下流製品情報

上流原料

2-エチル-1-ヘキサノールオゾンアゼライン酸

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