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Home > Encyclopedia > Dioctyl adipate

Dioctyl adipate

Dioctyl adipate structure

Dioctyl adipate 

structure
  • CAS No:

    123-79-5

  • Formula:

    C22H42O4

  • Chemical Name:

    Dioctyl adipate

  • Synonyms:

    Hexanedioic acid,1,6-dioctyl ester;Adipic acid,dioctyl ester;Hexanedioic acid,dioctyl ester;Dioctyl adipate;Di-n-octyl adipate;Octyl adipate;NSC 16201;Dicaprylyl adipate

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

COLOURLESS-TO-YELLOW LIQUID.


Liquid|Clear colourless liquid; Slight fatty aroma


Dioctyl hexanedioate is a carboxylic ester.

Dioctyl adipate Basic Attributes

370.56600

370.57

204-652-9

2BD76YG9SI

16201

DTXSID2021606

COLORLESS OR VERY PALE AMBER LIQUID|Clear liquid

Characteristics

52.60000

6.35420

Liquid

0.929 g/cm3

7.49 °C

214 °C

178.6ºC

1.4474

Solubility in water, g/100ml at 20°C: (none)

Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition so

8.50X10-7 mm Hg @ 20 deg C

Relative vapour density (air = 1): 12.8

Explosive limits , vol% in air: 0.3-2.8

SLIGHT, AROMATIC SMELL

4.34e-07 atm-m3/mole

6.73X10-8 J/kmol

Critical temperature: 556.84 °C (830 K); Critical pressure: 1.13X10+6 Pa

Safety Information

III

9

3082

3

S22-S24/25

Separated from strong oxidants and strong acids. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

H315

...CAN REACT WITH OXIDIZING MATERIALS.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 69 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

FOAM, CARBON DIOXIDE, DRY CHEMICAL ...

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.

An eye and skin irritant.

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).

SEDIMENT: Dioctyl adipate (isomer not reported) was detected (concn not reported) in sediment collected from the Charles River in Boston in Sept 1973(1).

Di-n-octyl adipate was detected by GC/MS, but not quantified, in weathered limestone samples collected from Sevilla, in southwestern Spain and Mechelen, in northern Belgium(1).

Toxicity

LD50 Rat oral 9110 mg/kg|LD50 Rat iv 900 mg/kg|LD50 Mouse oral 15 g/kg|LD50 Rabbit iv 540 mg/kg

Di-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).

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).

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).

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.

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.

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).

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).

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)

Drug Information

/SRP:/ Basic Treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Esters and related compounds/|/SRP:/ Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Consider drug therapy for pulmonary edema ... . Use propaparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

dioctyl hexanedioate

Dioctyl adipate Use and Manufacturing

Methods of Manufacturing

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.

Uses

Primary type of plasticizer for use with resins @ low temp. Plasticizer for synthetic rubbers, nitrocellulose, & ethyl cellulose.

Production

< 25,000 lb|(1972) 6.08X10+8 G (SALES-INCL DIISOOCTYL)|(1975) PROBABLY GREATER THAN 4.54X10+5 G

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).

Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:370.6
XLogP3:7.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:21
Exact Mass:370.30830982
Monoisotopic Mass:370.30830982
Topological Polar Surface Area:52.6
Heavy Atom Count:26
Complexity:296
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

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