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Ethylidene diacetate

From Wikipedia, the free encyclopedia
Ethylidene diacetate
Names
Preferred IUPAC name
Ethane-1,1-diyl diacetate
Other names
1,1-Diacetoxyethane
1,1-Ethanediol diacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.008.001Edit this at Wikidata
UNII
  • InChI=1S/C6H10O4/c1-4(7)9-6(3)10-5(2)8/h6H,1-3H3
    Key: ACKALUBLCWJVNB-UHFFFAOYSA-N
  • InChI=1/C6H10O4/c1-4(7)9-6(3)10-5(2)8/h6H,1-3H3
    Key: ACKALUBLCWJVNB-UHFFFAOYAU
  • CC(OC(=O)C)OC(=O)C
Properties
C6H10O4
Molar mass146.14
AppearanceColorless liquid
Density1.07 g/cm3
Melting point18.9 °C (66.0 °F; 292.0 K)
Boiling point167–169 °C (333–336 °F; 440–442 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Ethylidene diacetate is anorganic compound with theformula (CH3CO2)2CHCH3. A colorless low-melting solid, it once served as a precursor tovinyl acetate.

Preparation

[edit]

A major industrial route involves the reaction ofacetaldehyde andacetic anhydride in the presence of aferric chloride catalyst:[1][2]

CH3CHO + (CH3CO)2O → (CH3CO2)2CHCH3

It can be converted to the valuable monomervinyl acetate by thermal elimination ofacetic acid:

(CH3CO2)2CHCH3 → CH3CO2CH=CH2 + CH3CO2H

References

[edit]
  1. ^G. Roscher "Vinyl Esters" inUllmann's Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.doi:10.1002/14356007.a27_419
  2. ^GB Patent 238825A 'Process of Manufacture of Acetic Anhydride and Aldehyde'
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