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Dioctyl azelate

Dioctyl azelate structure

Dioctyl azelate 

structure
  • CAS No:

    103-24-2

  • Formula:

    C25H48O4

  • Chemical Name:

    Dioctyl azelate

  • Synonyms:

    Nonanedioic acid,1,9-bis(2-ethylhexyl) ester;Azelaic acid,bis(2-ethylhexyl) ester;Nonanedioic acid,bis(2-ethylhexyl) ester;Azelaic acid di(2-ethylhexyl) ester;Bis(2-ethylhexyl) azelate;Dioctyl azelate;Plastolein 9058;Staflex DOX;Truflex DOX;Octyl azelate;Di-2-ethylhexyl azelate;Plastolein 9058DOZ;DOZ;Bis(2-ethylhexyl) nonanedioate;Sansocizer DOZ;Emery 2958;Emolien 2986;Nonanedioic acid di(2-ethylhexyl) ester;Dioctyl nonanedioate;Edenol 9058;29058-99-9

  • Categories:

    Catalyst and Auxiliary  >  Plastic Rubber Chemicals

Description

Liquid


Liquid

Dioctyl azelate Basic Attributes

412.64600

412.65

203-091-7

5D67SBH6QB

DTXSID3026697

Colorless liquid

2917139000

Characteristics

52.60000

7.23630

Liquid

0.915 g/cm3 @ Temp: 25 °C

-78 °C

237 °C @ Press: 5 Torr

184.6ºC

1.453

Insol in water; sol in ethanol, acetone, benzene

0mmHg at 25°C

Odorless

Safety Information

CM2000000

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.

Not Classified

INDOOR 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).

Toxicity

Di-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).

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).

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).

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.

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.

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).

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).

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).

Drug Information

THESE ESTERS HAVE VERY LOW ORDER OF TOXICITY. /AZELATE ESTERS/

Dioctyl azelate Use and Manufacturing

Methods of Manufacturing

REACTION OF AZELAIC ACID WITH 2-ETHYLHEXYL ALCOHOL IN THE PRESENCE OF AN ACID CATALYST

Uses

This product is an excellent cold-resistant plasticizer. It has good compatibility with polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polystyrene, polyvinyl acetate, cellulose acetate butyrate, nitrocellulose, ethyl cellulose, etc. Its viscosity is low, boiling point is high, plasticization efficiency is high, volatility and migration are small, and it has excellent heat resistance, light resistance, electrical insulation and viscosity stability to plasticized paste. Cold resistance is better than DOA. It is suitable for artificial leather, film, sheet, wire and cable sheath, plasticized paste, etc. It can give products good low temperature performance. This product can also be used alone or in combination with other plasticizers as a plasticizer for synthetic rubber such as nitrile rubber, styrene butadiene rubber, neoprene rubber, etc.


Functional fluids (closed systems)


Lubricants and greases

Production

1,000,000 - 10,000,000 lb|(1972) 5.15X10+9 G|(1975) PROBABLY GREATER THAN 1.36X10+6 G

Grade: 99% pure

All other chemical product and preparation 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/

Computed Properties

Molecular Weight:412.6
XLogP3:8.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:22
Exact Mass:412.35526001
Monoisotopic Mass:412.35526001
Topological Polar Surface Area:52.6
Heavy Atom Count:29
Complexity:358
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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