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Dimethyl adipate

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Dimethyl adipate
Names
Preferred IUPAC name Dimethyl hexanedioate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.019 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H14O4/c1-11-7(9)5-3-4-6-8(10)12-2/h3-6H2,1-2H3Key: UDSFAEKRVUSQDD-UHFFFAOYSA-N
SMILES
  • COC(=O)CCCCC(=O)OC
Properties
Chemical formula C8H14O4
Molar mass 174.196 g·mol
Appearance Colorless liquid
Density 1.06 g/cm (20 °C)
Melting point 10.3 °C (50.5 °F; 283.4 K)
Boiling point 227 °C (441 °F; 500 K)
Solubility in water < 1 g/L
Viscosity 2.5 cP @ 25°C
Hazards
Flash point 107 °C (225 °F; 380 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

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.

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.).

References

  1. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ 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.
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