Dimethyl adipate

Dimethyl adipate
Names
Preferred IUPAC name
Dimethyl hexanedioate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.019
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).
Infobox references

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]

Preparation

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

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]

Uses

Dimethyl adipic acid is used in cosmetics as an emollients and for skin conditioning. It is also used in agrochemicals and dyes, as well as a precursor for the production of pharmaceutical active ingredients and as a component of dibasic esters.[3][4]

References

  1. 1 2 3 4 5 6 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 3 Musser, M. T. (2005). "Adipic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_269. ISBN 3527306730.
  3. ↑ T.S.S. Dikshith (2016), [, p. 196, at Google Books Handbook of Chemicals and Safety], CRC Press, p. 196, ISBN 978-1-4398-2061-2 {{citation}}: Check |url= value (help)
  4. ↑ Dimethyl adipate, 99% at AlfaAesar, accessed on {{{Datum}}} (PDF) (JavaScript required).
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