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Dioctyladipat

Dioctyl Adipate

HCID 31271
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Grundinformationen

CAS
123-79-5
Standard-SMILES
CCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCC
InChIKey
NEHDRDVHPTWWFG-UHFFFAOYSA-N
Summenformel
C22H42O4
Durchschnittliche Molmasse
370,6 g/mol
Monoisotopische Masse
370,30830982

Überblick

Dioctyl hexanedioate is a carboxylic ester.

Namen und Bezeichner

Bevorzugter Name
Dioctyl Adipate
IUPAC
dioctyl hexanedioate
Lokaler Name
Dioctyladipat
Englischer Name
Dioctyl adipate
Summenformel
C22H42O4
Molmasse
370.57

Namen und Synonyme

Dioctyl adipate123-79-5Dioctyl hexanedioateDi-n-octyl adipateHexanedioic acid, dioctyl esterDicaprylyl adipateAdipic acid, dioctyl ester1,6-dioctyl hexanedioate2BD76YG9SINSC-16201DTXSID2021606FEMA NO. 4476
Weitere Namen anzeigen
DOADioctyladipatDioctyl hexadioate2,2-dioctylhexanedioateDioctyl adipate in stock FactoryERXINZHINSC16201Adiimoll DO
DEHA compoundRefChem:920377di-2-ethyl-hexyl adipateDTXCID701606204-652-9Hexanedioic acid, 1,6-dioctyl esterHexanedioic acid,1,6-dioctyl esterNSC 16201

Datenbank-Bezeichner

CAS
123-79-5
PubChem CID
31271
DTXSID
DTXSID2021606
ChEBI
CHEBI:168986
UNII
2BD76YG9SI
EC Number
204-652-9
Nikkaji
J45.961E

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
7,4
Polarare Oberfläche (TPSA)
52,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
21
Schwere Atome
26
Formalladung
0
Komplexität
296

Experimentelle und physikochemische Eigenschaften

FragrancesFragrance Ingredient (Hexanedioic acid, dioctyl ester) -> IFRA transparency List
OdorSLIGHT, AROMATIC SMELL
PlasticizersPlastics & Rubber -> Other Plasticizers
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 Einträge

1.2145X10+8 kmol/cu m @ 7.49 °C (280.65 K)

0.924-0.930 (20 °C)

Flavoring AgentsEU Flavoring substances
Viscosity1.89X10-2 Pa sec @ 7.49 °C (280.65 K)
Color/Form · 2 Einträge

COLORLESS OR VERY PALE AMBER LIQUID

Clear liquid

Solubility · 5 Einträge

INSOL IN WATER @ 25 °C; INSOL OR VERY SLIGHTLY SOL IN GLYCERINE & GLYCOLS; SOL IN MOST ORGANIC SOLVENTS

In water, 0.78 mg/l @ 22 °C

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 · 5 Einträge

This chemical does not meet GHS hazard criteria for 75.8% (135 of 178) of all reports.

Warning

H315 (24.2%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 178 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Hexanedioic acid, dioctyl ester

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

Hexanedioic acid, 1,6-dioctyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanedioic acid, 1,6-dioctyl 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)

Hexanedioic acid, dioctyl 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 SummaryAcute high-dose animal studies show moderate toxicity by IV route and mild toxicity by ingestion; A skin and eye irritant; Oral LD50 (rat) = 9110 mg/kg; [Sax]
Hazard Classes and CategoriesSkin Irrit. 2 (24.2%)
Skin, Eye, and Respiratory IrritationsAn eye and skin irritant.

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsExtracellular

Verwendung und Herstellung

Uses · 3 Einträge

Used as a low-temperature plasticizer for synthetic rubbers, nitrocellulose, and ethyl cellulose; [HSDB]

PRIMARY TYPE OF PLASTICIZER FOR USE WITH RESINS @ LOW TEMP. ... PLASTICIZER FOR SYNTHETIC RUBBERS, NITROCELLULOSE, & ETHYL CELLULOSE.

It is used as a plasticizer for synthetic rubbers, nitro cellulose and ethyl cellulose.

U.S. Exports(1984) 7.54X10+8 g /Adipic Acid Esters of Monohydric Alcohols/
U.S. Imports(1984) 1.60X10+9 g /Products chiefly used as plasticizers/
U.S. Production · 3 Einträge

2023: 550,000 - <700,000 lb

(1972) 6.08X10+8 G (SALES-INCL DIISOOCTYL)

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Consumer UsesProcessing aids not otherwise specified
Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing · 2 Einträge

ESTERIFICATION OF ADIPIC ACID WITH 1-OCTANOL; ESTER EXCHANGE OF LOWER DIALKYL ADIPATE WITH 1-OCTANOL WITH BASE CATALYSIS

Esterification of adipic acid with octanol.

Use Classification · 3 Einträge

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 4 Einträge

Zugehörige Reaktionen

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0.78 mg/L @ 22 °C (exp)

Practically insoluble or insoluble in water

Soluble (in ethanol)

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Boiling Point · 3 Einträge

Normal Boiling Point: 404.84 °C (687 K)

396.00 to 398.00 °C. @ 760.00 mm Hg

396-398 °C

DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.

Physikochemische Eigenschaften

Schmelzpunkt
-67.8 ℃ · -67.8℃
Siedepunkt
214 ℃ · 214℃
Dichte
0.922 · 0.922
FEMA
4476 · 4476 | DIOCTYL ADIPATE
Brechungsindex
1.4474 · 1.4474
Flammpunkt
196 ℃ · 196℃
Geruch (Odor)
Mild characteristic.
Geruchsart
fatty
JECFA Number
1968 · 1968
InChI
InChI=1S/C22H42O4/c1-3-5-7-9-11-15-19-25-21(23)17-13-14-18-22(24)26-20-16-12-10-8-6-4-2/h3-20H2,1-2H3
InChIKey
NEHDRDVHPTWWFG-UHFFFAOYSA-N
SMILES
C(OCCCCCCCC)(=O)CCCCC(OCCCCCCCC)=O
LogP
6.11 · 6.11
CAS Datenbank
123 · 123-79-5(CAS DataBase Reference)
NIST chemische Informationen
Hexanedioic acid, dioctyl ester(123-79-5)
EPA chemische Informationen
Dioctyl adipate (123-79-5)
Critical Temperature and PressureCritical temperature: 556.84 °C (830 K); Critical pressure: 1.13X10+6 Pa
Hazardous Reactivities and Incompatibilities...CAN REACT WITH OXIDIZING MATERIALS.

Sicherheit und Schutzausrüstung

Fire Fighting ProceduresFOAM, CARBON DIOXIDE, DRY CHEMICAL ...
Preventive Measures · 1 Eintrag

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 57,000(SRC), determined from a structure estimation method(2), indicates that di-n-octyl adipate is expected to be immobile in soil(SRC). Volatilization of di-n-octyl adipate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.34X10-7 atm-cu m/mole(3). Di-n-octyl adipate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.5X10-7 mm Hg(3). Based upon analogy to biodegradation screening studies for the structurally-similar bis(2-ethylhexyl) adipate(3), biodegradation is expected to be the major degradation process for di-n-octyl adipate in soil.

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 57,000(SRC), determined from an estimation method(2), indicates that di-n-octyl adipate is 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 4.34X10-7 atm-cu m/mole(5). Di-n-octyl adipate is expected to undergo hydrolysis producing octanol and adipic acid(SRC). Estimated hydrolysis half-lives are 5 years and 170 days at pH values of 7 and 8, respectively(5). Biodegradation is expected to be a major degradation process for di-n-octyl adipate in environmental waters(6). According to a classification scheme(4), a BCF of 27(5), 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-n-octyl adipate, which has a vapor pressure of 8.5X10-7 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase di-n-octyl 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 0.67 days(SRC), calculated from its rate constant of 2.4X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). Particulate-phase di-n-octyl adipate may be removed from the air by wet and dry deposition(SRC). Di-n-octyl adipate may undergo direct photolysis in the environment, since this compound contains a functional group that can absorb light >290 nm(4).

Effluent Concentrations · 1 Eintrag

Release to the air can occur during incineration of municipal refuse, industrial rubbish and waste products from plastic production and other processes that use dioctyl adipate plasticizers(1). Leachates from municipal and industrial landfills that contain plastics may contain dioctyl adipate(1). Dioctyl adipate has been detected in wastewater effluents from the pulp and paper industry and in sewage treatment effluents(2,3). Di-n-octyl adipate was detected in effluent irrigation samples collected from Glil-Yam, 15 km north of Tel-Aviv, Israel at a concentration of 1,500 ppb from a depth of 9-10 m(4).

Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc for di-n-octyl adipate can be estimated to be 57,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that di-n-octyl adipate is expected to be immobile in soil.

Artificial Pollution SourcesDi-n-octyl adipate's production and use as a plastizer for synthetic rubbers, nitro cellulose and ethyl cellulose(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 Eintrag

AEROBIC: In a semi-continuous activated sludge method used to simulate sewage treatment plant biodegradation, di-n-octyl adipate was observed to undergo primary degradation of 65-96% (at concns of 5 and 20 mg/l added/24 hr)(1); in a CO2 evolution study, di-n-octyl adipate was observed to biodegrade 94% over a 35-day incubation period which corresponds to a first-order half-life of 2.7 days(1).

Sediment/Soil ConcentrationsSEDIMENT: Dioctyl adipate (isomer not reported) was detected (concn not reported) in sediment collected from the Charles River in Boston in Sept 1973(1).
Environmental Bioconcentration · 1 Eintrag

A whole-fish BCF of 27 was observed for blue-gill fish exposed di-n-octyl adipate levels of 250 ug/l for a 28-day period(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1 Eintrag

The estimated Henry's Law constant for di-n-octyl adipate is 4.34X10-7 atm-cu m/mole(1). This estimated Henry's Law constant indicates that di-n-octyl adipate is not expected to volatilize from water surfaces(2). Di-n-octyl adipate's estimated Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Di-n-octyl adipate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.5X10-7 mm Hg(1).

Non-Human Toxicity Excerpts · 4 Einträge

NO ACUTE EFFECT HAS BEEN OBSERVED SOME HR AFTER ORAL ADMIN TO GUINEA PIGS OF DOSES ... EQUAL TO OR LESS THAN 14 ML/KG BODY WT. YET IN SUCCEEDING DAYS (3-21 DAYS) HALF OF ANIMALS DIED.

... DOSES OF 5 ML/KG /ADMIN TO GUINEA PIGS/ DID NOT CAUSE ANY MORTALITY, WHILE WITH 20 ML/KG, ALL ANIMALS ULTIMATELY SUCCUMBED IN ENSUING WEEKS. DEATH WAS PRECEDED BY PROGRESSIVE INFEEBLEMENT & MUSCULAR ATROPHY ... .

IN LONG-TERM TOXICITY TESTS, DAILY DOSES OF ADIPATE 0.61 MG/KG BODY WT HAVE NOT CAUSED ANY REACTION IN RATS AFTER NINETY DAYS.

Moderately toxic by intravenous route. Mildly toxic by ingestion. An eye and skin irritant.

Environmental Abiotic Degradation · 1 Eintrag

The rate constant for the vapor-phase reaction of di-n-octyl adipate with photochemically-produced hydroxyl radicals has been estimated as 2.4X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 0.67 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Di-n-octyl adipate is expected to undergo hydrolysis producing octanol and adipic acid(SRC). A base-catalyzed second-order hydrolysis rate constant of 4.7 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 5 years and 170 days at pH values of 7 and 8, respectively(2). Di-n-octyl adipate 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 Eintrag

Occupational exposure to di-n-octyl adipate may occur through inhalation of dust particles and dermal contact with this compound at workplaces where di-n-octyl adipate is produced or used. The general population may be exposed to di-n-octyl adipate via drinking water, and dermal contact with this compound and other products containing di-n-octyl adipate. (SRC)

Environmental Water Concentrations · 2 Einträge

DRINKING WATER: Di-n-octyl adipate was detected, not quantified, in 4 of 5 raw river water samples collected from a pilot plant in Evansville, IN(1). A dioctyl adipate (isomer not reported) conc of 20 ug/l was detected in a drinking water sample collected from Miami, FL(2).

SURFACE WATER: Dioctyl adipate (isomer not reported) was detected at levels ranging from 2 to 86 ppb in 7 of 204 samples collected from 14 heavily industrialized river basins in the US between Aug 1975 and Sept 1976(1).

Sicherheitsdaten

wgk
WGK 2
tsca
TSCA listed
hs_code
29171200
Speicherklasse
10 - Combustible liquids
Giftige Stoffe Daten
123-79-5(Hazardous Substances Data)
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2

All Other Chemical Product and Preparation Manufacturing

Hexanedioic acid, 1,6-dioctyl ester: ACTIVE

IN FRANCE & ITALY DIOCTYL ADIPATE IS PERMITTED AS A CONSTITUENT OF PLASTICS INTENDED FOR CONTACT WITH FOODSTUFFS.

IN ASSOC WITH PHTHALATES IT CONFERS EXCELLENT COLD RESISTANCE & BETTER FLEXIBILITY @ ALL TEMP TO VINYL RESINS (CHLORIDE, ACETATE-CHLORIDE, POLYVINYLIDENE CHLORIDE).

Anwendungen

VerwendenDioctyl adipate is used as a plasticizer for synthetic rubbers, nitrocellulose, and ethyl cellulose.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Adipinsure2-Ethylhexan-1-olOctan-1-ol