Ethylidene diacetate

Ethylidene diacetate is an organic compound with the formula (CH3CO2)2CHCH3. A colorless low-melting solid, it once served as a precursor to vinyl acetate.

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 InfoCard 100.008.001
UNII
Properties
C6H10O4
Molar mass 146.14
Appearance Colorless liquid
Density 1.07 g/cm3
Melting point 18.9 °C (66.0 °F; 292.0 K)
Boiling point 167–169 °C (333–336 °F; 440–442 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

A major industrial route involves the reaction of acetaldehyde and acetic anhydride in the presence of a ferric chloride catalyst:[1][2]

CH3CHO + (CH3CO)2O → (CH3CO2)2CHCH3

It can be converted to the valuable monomer vinyl acetate by thermal elimination of acetic acid:

(CH3CO2)2CHCH3 → CH3CO2CH=CH2 + CH3CO2H

References

  1. G. Roscher "Vinyl Esters" in Ullmann'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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