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Dimethyl adipate

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Dimethyl adipate
Names
Preferred IUPAC name
Dimethyl hexanedioate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.019 Edit this at Wikidata
UNII
  • InChI=1S/C8H14O4/c1-11-7(9)5-3-4-6-8(10)12-2/h3-6H2,1-2H3
    Key: UDSFAEKRVUSQDD-UHFFFAOYSA-N
  • COC(=O)CCCCC(=O)OC
Properties
C8H14O4
Molar mass 174.196 g·mol−1
Appearance Colorless liquid[1]
Density 1.06 g/cm3 (20 °C)[1]
Melting point 10.3 °C (50.5 °F; 283.4 K)[1]
Boiling point 227 °C (441 °F; 500 K)[1]
< 1 g/L[1]
Viscosity 2.5 cP @ 25°C
Hazards
Flash point 107 °C (225 °F; 380 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dimethyl adipate is the organic compound with the formula (CH2CH2CO2CH3)2. It is a colorless oily liquid. Although the main commercial interest in adipates is related to the production of nylons, this diester is used as a plasticizer, a solvent for paint stripping and resins, and a pigment dispersant.[2][3]

Preparation

[edit]

Dimethyl adipate is prepared by esterification of adipic acid with methanol. Less conventional routes include the hydroesterification of butadiene and the carbonylation of 1,4-dimethoxy-2-butene.[2]

It reacts with concentrated ammonia to give the diamide (CH2CH2C(O)NH2)2.

Toxicity

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Esters of adipic acid exhibit low acute toxicities in animal models. The LD50 of this dimethyl ester is estimated at 1800 mg/kg (rat, i.p.).[2]

References

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  1. ^ a b c d e f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b c Musser, M. T. (2005). "Adipic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_269. ISBN 3527306730.
  3. ^ "Dimethyl Adipate". chemicalland21.com.