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다이메틸 지방질

Dimethyladipate

HCID 12329
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
627-93-0
표준 SMILES
COC(=O)CCCCC(=O)OC
InChIKey
UDSFAEKRVUSQDD-UHFFFAOYSA-N
분자식
C8H14O4
평균 분자량
174.19 g/mol
단동위원소 질량
174.08920892

개요

Dimethyl adipate is a colorless liquid. (USCG, 1999)

이름 및 식별자

우선 이름
Dimethyladipate
IUPAC
dimethyl hexanedioate
현지명
다이메틸 지방질
영어명
Dimethyl adipate
분자식
C8H14O4
분자량
174.19

이름 및 동의어

DimethyladipateRefChem:134217Dimethyl adipate627-93-0Dimethyl hexanedioateAdipic acid dimethyl esterHEXANEDIOIC ACID, DIMETHYL ESTERAdipic acid, dimethyl ester1,6-DimethylhexanedioateDBE 61,6-dimethyl hexanedioatehexanedioic acid dimethyl ester
이름 더 보기
다이메틸아디페이트다이메틸지방질다이메틸지방질(DIMETHYLADIPATE)다이메틸 아디페이트다이메틸 헥세인다이오에이트메틸 아디페이트아디프산, 다이메틸아디프산, 다이메틸 에스터헥세인이산, 1,6-다이메틸 에스터헥세인이산, 다이메틸 에스터dbe-6Adipic acid-diDimethyladipatAKOS BBS-00004546Flexisolv DBE-LVPDBE 6 DIBASIC ESTERAdipic acid dimethyl
MFCD00008469DibasicestersDTXSID8025096Adipic acid-dimethyl esteradipinic acid dimethyl esterDiMethyl Hexanedioate--d4Hexanedioic acid, 1,6-dimethyl esterdimethyl hexane-1,6-dioate

데이터베이스 식별자

CAS
627-93-0
PubChem CID
12329
DTXSID
DTXSID8025096
ChEMBL
CHEMBL1566491
ChEBI
CHEBI:34715
UNII
BY71RX0R62
EC Number
211-020-6
Nikkaji
J518E

물성

구조 계산 물성보충 중

XLogP
1
극성 표면적
52.6 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
7
무거운 원자 수
12
형식 전하
0
복잡도
135

실험 및 물리화학적 성질

SolventsSolvents -> Esters (<C12)
Cosmetics · 2건

Cosmetic ingredients (Dimethyl Adipate) -> CIR (Cosmetic Ingredient Review)

Emollient; Plasticiser

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Dimethyl adipate) -> IFRA transparency List
LogP · 3건

log Kow= 1.03

1.030

1.03

PlasticizersPlasticizer
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 4건

1.063 (USCG, 1999) - Denser than water; will sink

1.0600 @ 20 °C/4 °C

1.062-1.066 (20 °C)

1.063

Color/FormLiquid
Solubility · 5건

Sol in alc, ether, acetic acid

In water, 600 mg/l, temp not specified.

Insoluble

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 64.2% (682 of 1062) of all reports.

Warning

H319 (32.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 1062 reports by companies from 11 notifications to the ECHA C&L Inventory.

유해성 정보

Regulatory Information · 4건

Chemical: Hexanedioic acid, dimethyl ester

Hexanedioic acid, 1,6-dimethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanedioic acid, 1,6-dimethyl 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: Dimethyl adipate (EC: 211-020-6)

Dimethyl adipate: Does not have an individual approval but may be used under an appropriate group standard

Health HazardsMay be harmful by inhalation, ingestion, or skin absorption. May cause irritation. (USCG, 1999)
Hazards SummaryMay cause irritation; [MSDSonline]
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
EPA Safer ChemicalChemical: Dimethyl adipate
Reactivity Profile · 1건

DIMETHYL ADIPATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

The metabolism of dibasic esters by rat nasal mucosal tissues was studied in-vitro. Homogenates of olfactory tissue from the ethmoturbinates and respiratory tissue from the nasoturbinates and maxilloturbinates of Crl:CDBR-rats were incubated with dimethyl succinate, dimethyl glutarate, or dimethyl adipate. Values of the reaction velocity at saturating substrate concentration (Vmax), the second order rate constant for binding and catalysis (V/K), the Michaelis constant (Km), and the dibasic ester concentration required to produce half maximal inhibition of the reaction rate (Ksi) were computed. The dibasic esters were hydrolyzed to their monomethyl esters by both the olfactory and respiratory mucosal homogenates. No diacid metabolites were detected. The rates of hydrolysis were always greater in the olfactory than in the respiratory homogenates. Vmaxs in olfactory tissue from male rats were 5 to 9 times higher than in respiratory tissue. In female rats, Vmaxs in the olfactory homogenates were 6 to 13 times those of the respiratory mucosa. V/Ks in male and female olfactory tissue were 4 to 11 and 6 to 10 times those in the corresponding respiratory tissue, respectively. When dimethyl glutarate was used as the substrate, V/Ks were similar for male and female olfactory tissue. In the case of dimethyl succinate and dimethyl adipate, V/K values for female olfactory tissue were 0.5 and 2 times those of the male tissues, respectively. The largest Km values in the olfactory tissues occurred when dimethyl adipate was used as the substrate, followed by dimethyl adipate and dimethyl glutarate in that order. The Ki values ranged from 24 to 46.5 millimolar. Female rats were pretreated with 1% bis-p-nitrophenyl phosphate, a carboxylesterase specific inhibitor. Bis-p-nitrophenyl phosphate decreased the rates of hydrolysis of dimethyl adipate, dimethyl glutarate, and dimethyl succinate in olfactory tissue by 79.8, 81, and 72%, respectively. The corresponding rates of hydrolysis in respiratory tissue were reduced by 87, 73, and 95%. The authors conclude that lesions induced in the nasal cavity of rodents by inhaled esters may be due to toxic acid metabolites.

Cellular LocationsCytoplasm

용도 및 제조

Uses · 5건

관련 반응

29건
반응 기록 만들기
HRID 65824 반응식
HRID 65824반응물로uspto-grants-1978_12
HRID 263216 반응식
HRID 263216생성물로uspto-grants-1979_05
HRID 330344 반응식
HRID 330344반응물로uspto-grants-1990_01
HRID 429503 반응식
HRID 429503반응물로uspto-grants-2001_11
HRID 476748 반응식
HRID 476748생성물로uspto-grants-1989_12
HRID 616621 반응식
HRID 616621반응물로uspto-grants-1978_02
HRID 883815 반응식
HRID 883815생성물로uspto-grants-2012_08
HRID 956776 반응식
HRID 956776반응물로Validation data from https://doi.org/10.1039/C8SC04228D
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Very slightly soluble in water

Soluble (in ethanol)

Flash Point · 3건

225 °F (USCG, 1999)

107 °C

225 °F

Boiling Point · 5건

228.2 to 230 °F at 14 mmHg (USCG, 1999)

115 °C @ 13 mm Hg

109.00 to 110.00 °C. @ 14.00 mm Hg

109-110 °C (14 mmHg)

228.2-230 °F at 14 mmHg

물리화학적 성질

녹는점
8 °C · 8 °C (lit.)
끓는 점
109 · 109-110 °C/14 mmHg (lit.)
밀도
1.062 g/mL · 1.062 g/mL at 20 °C (lit.)
증기압
0.2 mm · 0.2 mm Hg ( 20 °C)
굴절률
20 · n20/D 1.428(lit.)
FEMA
4472 · 4472 | DIMETHYL ADIPATE
인화점
225 °F · 225 °F
저장 조건
30 °C · Store below +30°C.
용해도
1 g/L · <1g/L
물리적 상태
액체
색상
투명한
냄새
100 %에서 · 100.00%에서. 순한 견과류
냄새 유형
견과류
폭발한계
0.81 · 0.81-8.1%(V)
수용성
알코올 및 에테르와 혼합 가능합니다. 물과 섞이지 않습니다.
Merck
14 · 14,162
JECFA Number
1964 · 1964
BRN
1707443 · 1707443
Henry's Law Constant
4.3 · 4.3×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
안정성
안정적인. 타기 쉬운. 강산화제, 산, 염기 환원제와 호환되지 않습니다.
화장품 원료 기능
용제가소제피부 컨디셔닝 - 보습제
InChI
1S/C8H14O4/c1-11-7(9)5-3-4-6-8(10)12-2/h3-6H2,1-2H3
InChIKey
UDSFAEKRVUSQDD-UHFFFAOYSA-N
SMILES
COC(=O)CCCCC(=O)OC
LogP
1.4 at · 1.4 at 22℃
NIST
Hexanedioic acid, dimethyl ester(627-93-0)
EPA
Dimethyl adipate (627-93-0)

화학적 성질

Dimethyl adipate is a colorless liquid. It is a fatty acid methyl ester.

Air and Water ReactionsFlammable. Hydrolyzed by strong mineral acids and strong alkalis.
Hazard Classes and CategoriesEye Irrit. 2A (32.4%)
Lower Explosive Limit (LEL) · 2건

0.81 % (USCG, 1999)

0.81%

Upper Explosive Limit (UEL) · 2건

8.1 % (USCG, 1999)

8.1%

안전 및 보호

Fire FightingFire Extinguishing Agents: Carbon dioxide, dry chemical, alcohol foam. (USCG, 1999)
First AidINHALATION: Call for medical aid. Remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Nonfire Spill ResponseNeutralizing Agents for Acids and Caustics: Data (USCG, 1999)
Disposal Methods · 1건

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.

Personal Protective Equipment (PPE)Self-contained breathing apparatus, rubber boots and heavy rubber gloves. (USCG, 1999)

독성 정보

Interactions · 1건

The potential developmental effects of inhalation of dibasic esters (DBE) were investigated in the rat. The DBE mixture consisted of 65.12% dimethyl-glutarate, 17.75% dimethyl-succinate and 16.83% dimethyl-adipate. Starting at Day seven of gestation, pregnant Crl:CD-BR-rats were exposed whole body to dibasic esters at 0.16, 0.4 or 1.0 mg/l for 6 hours/day. On Day 21 of gestation, female rats were euthanized, and the fetuses were examined for external, visceral and skeletal alterations. Feed consumption during the first 6 days and body weight were reduced in pregnant rats in the 0.4 and 1.0 mg/l groups. Perinasal staining and wet fur were seen in the 1.0 mg/l group. Adverse reproductive effects of dibasic esters exposure were not detected, and there was no effect on fetal weight. No significant differences were seen in the incidences of external, visceral and skeletal alterations in exposed and control fetuses. The authors conclude that dibasic esters is not a developmental toxicant by inhalation in the rat at concentrations as high as 1.0 mg/l.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a structure estimation method(2), indicates that dimethyl adipate is expected to have very high mobility in soil(SRC). Volatilization of dimethyl adipate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.77X10-7 atm-cum/mole(4), determined from a fragment constant estimation method(4). Dimethyl adipate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.06 mm Hg(3).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from an estimation method(2), indicates that dimethyl adipate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.77X10-7 atm-cu m/mole(7), developed using a fragment constant estimation method(7). According to a classification scheme(4), an estimated BCF of 1.2(SRC), from a log Kow of 1.03(6) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is low. Dimethyl adipate is expected to undergo hydrolysis producing hexanedioic acid and methanol(SRC). Estimated hydrolysis half-lives are 2 years and 60 days at pH values of 7 and 8, respectively(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethyl adipate, which has a vapor pressure of 0.06 mm Hg at 25 °C(3), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dimethyl 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 4 days(SRC), calculated from its rate constant of 4X10-12 cu cm/molecule-sec at 25 °C(2). Dimethyl adipate may undergo direct photolysis in the environment, since this compound contains a functional group that can absorb light >290 nm(4).

Adverse EffectsNeurotoxin - Acute solvent syndrome
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 · 1건

The Koc of dimethyl adipate is estimated as 11(SRC), using a log Kow of 1.03(3) and a regression-derived equation(1). According to a classification scheme(2), this estimated Koc value suggests that dimethyl adipate is expected to have very high mobility in soil.

Human Toxicity Excerpts · 1건

GENERAL TOXICITY OF /HIGHER-MOLECULAR-WT DIESTERS OF ADIPIC ACID/...IS SIMILAR IN MANY WAYS TO THAT OF PHTHALATE ESTERS &, IN SOME INSTANCES...MAY BE LESS. TOXICITY DATA ON ADIPATES...NOT QUITE AS EXTENSIVE AS FOR PHTHALATE ESTERS, & THUS CAUTION SHOULD BE TAKEN IN CONCLUDING THAT TOXIC EFFECTS...SIMILAR. /ADIPATE ESTERS/

Fish/Seafood ConcentrationsDimethyl adipate was found in fish from the Great Lakes(1). No data on the amount of dimethyl adipate in the fish and the identity of the lake from which the fish were taken was not given.
Artificial Pollution SourcesDimethyl adipate's production and use as a finish remover(1), may result in its release to the environment through various waste streams(SRC).
Sediment/Soil ConcentrationsSOIL: Dimethyl adipate was identified, not quantified in various buried Ah horizon soil samples collected from Alberta, Canada(1).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1건

An estimated BCF of 1.2 was calculated for dimethyl adipate(SRC), using a log Kow of 1.03(3) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1건

The Henry's Law constant for dimethyl adipate is estimated as 9.77X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dimethyl adipate is not expected to volatilize from water surfaces(2). Dimethyl adipate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Dimethyl adipate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.06 mm Hg (3).

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
AV1645000
독성
LD50 orally in Rabbit: 8191 mg/kg LD50 dermal Rabbit > 2250 mg/kg
HS 번호
29171290
safety_code
24/25
기존화학 물질
KE-18697
자연 발화 온도
680 °F
스토리지 클래스
10 - Combustible liquids
유해 물질 데이터
627-93-0(Hazardous Substances Data)

CIR ingredient: Dimethyl Adipate

Used as a plasticizer for cellulose type resins and a finish remover; [HSDB]

PLASTICIZER FOR CELLULOSE TYPE RESINS

Finish remover

Alternative solvent in remover formulas

U.S. Production2023: 8,500,000 - <10,000,000 lb
Consumer UsesDispersing agent
Industry UsesLubricating agent
Methods of Manufacturing · 3건

ESTERIFICATION OF ADIPIC ACID WITH METHANOL IN THE PRESENCE OF AN ACID CATALYST

BASF has further developed the hydroesterification of butadiene to give dimethyl adipate.

The first CO route to make adipic acid is a BASF process employing CO and methanol in a two-step process producing dimethyl adipate.

Household ProductsInformation on 56 consumer products that contain Dimethyl adipate in the following categories is provided:
Use Classification · 6건

EPA Safer Chemical Functional Use Classes -> Solvents

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Cosmetics -> Emollient; Plasticiser

General Manufacturing Information · 3건

Printing and Related Support Activities

Hexanedioic acid, 1,6-dimethyl ester: ACTIVE

A NUMBER OF POLYVINYL CHLORIDE PRODUCTS UTILIZE ONE OF THE HIGHER-MOLECULAR-WT DIESTERS OF ADIPIC ACID. /ADIPIC ACID ESTERS/

응용 분야 · 3건

개요Dimethyl adipate (DMA) is a colourless and flammable liquid. It is soluble in alcohol and ether but sparingly soluble in water. DMA is incompatible with strong oxidising agents, and on decomposition, it emits carbon monoxide, irritating and toxic fumes and gases, and carbon dioxide. DMA reacts with acids, alkalis, and strong oxidants. DMA is synthesised by the esterification of adipic acid. DMA is part of a dibasic ester (DBE) blend used as a major ingredient in several paint strippers, and the DBE blends used in paint stripping formulations contain a major portion (about 90%) of DMA. DMA is used as a chemical intermediate (polymers, agrochemicals), cellulose resins, a speciality solvent (inks, coatings, adhesives), and an emollient and can also be utilised as a paint remover and plasticiser.

용도Dimethyl adipate is used in cosmetics (in emollients and skin conditioning).It is used as a plasticizer for cellulose-type resins and a finish remover.It is also used in agrochemicals and dye as well as a precursor for the preparation of active pharmaceutical ingredients. Further, it serves as a polymer intermediate. In addition to this, it is employed as a solvent for paint stripping and resins.

일반 설명Colorless liquid.

제조 방법

생산 방법Dimethyl adipate is manufactured via esterification of adipic acid and methanol in the presence of an acid catalyst.

상·하류 제품 정보

상류 원료

아디핀산Monomethyl adipate디메틸에틸숙시네이트(1E,3E)-1,3-부타디엔-1,4-디카르복실산디메틸에스테르ADIPICSEMIALDEHYDEMETHYL에스테르D-Glucaric acidD-글루카르산1,4:6,3-디락톤2-메틸펜탄디오익산디메틸에스테르호모시트릭산-감마-락톤플루탈산디메틸에스테르6-옥소헥산산디메틸 세바케이트DIMETHYL PENTADECANEDIOATEDIMETHYL UNDECANEDIOATE

하류 제품

3-Ethyl-2-hydroxy-2-cyclopenten-1-one6-HYDROXYCAPROIC ACID