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Dibutyl azelate

Dibutyl azelate structure

Dibutyl azelate 

structure
  • CAS No:

    2917-73-9

  • Formula:

    C17H32O4

  • Chemical Name:

    Dibutyl azelate

  • Synonyms:

    Nonanedioic acid,1,9-dibutyl ester;Azelaic acid,dibutyl ester;Nonanedioic acid,dibutyl ester;Dibutyl azelate;Ergoplast AzDB;NSC 93294

Description

It is a high-boiling (336°C) liquid that is insoluble in water.

Dibutyl azelate Basic Attributes

300.43400

300.43

220-850-8

TSR57315NK

93294

DTXSID5044815

Liquid

2917139000

Characteristics

52.60000

4.40370

0.95g/cm3

107-108ºC

336 °C

152ºC

1.446

Insoluble in water

9.41E-05mmHg at 25°C

Wt/vol conversion: 12.26 mg/cu m is equiv to 1 ppm

Safety Information

P273, P501

H413

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.

H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]|P273, and P501|Aggregated GHS information provided by 12 companies from 1 notifications to the ECHA C&L Inventory.

Dibutyl azelate was identified, not quantified, in the air along the Niagara River near the Canadian/American border(1).

Toxicity

LD50 Mouse oral >12.8 g/kg|LD50 Mouse ip >12.8 g/kg|LD50 Guinea pig oral >10.0 g/kg

Dibutyl azelate's production and use as a plasticizer and contact lens constituent(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 2,700(SRC), determined from a structure estimation method(2), indicates that dibutyl azelate is expected to have slight mobility in soil(SRC). Volatilization of dibutyl azelate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3); however, adsorption may attenuate this process. Dibutyl azelate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3X10-4 mm Hg(SRC), determined from a fragment constant method(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2,700(SRC), determined from an estimation method(2), indicates that dibutyl 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 1.2X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 16 and 183 days, respectively if adsorption is ignored(SRC). The estimated volatilization half-life from a model pond is 600 days if adsorption is considered(5). A base-catalyzed second-order hydrolysis rate constant of 0.11 L/mole-sec(SRC) was estimated using a structure estimation method(6); this corresponds to half-lives of 2 years and 75 days at pH values of 7 and 8, respectively(6). According to a classification scheme(7), an estimated BCF of 590(SRC), from an estimated log Kow of 5.8(8,SRC) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is high(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibutyl azelate, which has an estimated vapor pressure of 3X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dibutyl 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 1 day(SRC), calculated from its estimated rate constant of 1.7X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Dibutyl azelate may also undergo direct photolysis in the environment since this compound contains a functional group that can absorb light greater than 290 nm(4).

The rate constant for the vapor-phase reaction of dibutyl azelate with photochemically-produced hydroxyl radicals has been estimated as 1.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.11 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 2 years and 75 days at pH values of 7 and 8, respectively(2). The expected hydrolysis products are butanol and azelaic acid. Dibutyl azelate may undergo photolysis in the environment since this compound contains a functional group that can absorb light greater than 290 nm(3).

An estimated BCF of 590 was calculated for dibutyl azelate(SRC), using an estimated log Kow of 5.8(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 high(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for dibutyl azelate can be estimated to be 2,700(SRC). According to a classification scheme(2), this estimated Koc value suggests that dibutyl azelate is expected to have slight mobility in soil(SRC).

The Henry's Law constant for dibutyl azelate is estimated as 1.2X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dibutyl azelate is expected to volatilize from water surfaces(2); however, adsorption may attenuate this process(SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 16 days if adsorption is ignored(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 183 days if adsorption is ignored(SRC). The estimated volatilization half-life of dibutyl azelate from a model pond is 600 days if adsorption is considered(3). Dibutyl azelate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC); however, adsorption may attenuate this process(SRC). Dibutyl azelate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3X10-4 mm Hg(SRC), determined from a fragment constant method(4).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 20,145 workers (7,808 of these are female) are potentially exposed to dibutyl azelate in the US(1). Occupational exposure to dibutyl azelate may occur through inhalation and dermal contact with this compound at workplaces where dibutyl azelate is produced or used(SRC). The general population may be exposed to dibutyl azelate through the use of consumer products, such as contact lenses, that contain this compound(SRC).

Dibutyl azelate Use and Manufacturing

Methods of Manufacturing

Esterification of butyl alcohol with azelaic acid

Uses

It is used as a component of contact lenses and as a plasticizer.

Production

(1977) AT LEAST 4.54X10+8 GRAMS|(1981) No Data

Nonanedioic acid, 1,9-dibutyl ester: ACTIVE

Computed Properties

Molecular Weight:300.4
XLogP3:4.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:16
Exact Mass:300.23005950
Monoisotopic Mass:300.23005950
Topological Polar Surface Area:52.6
Heavy Atom Count:21
Complexity:238
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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