Ethylidene diacetate

Ethylidene diacetate

Names
Preferred IUPAC name Ethane-1,1-diyl diacetate
Other names 1,1-Diacetoxyethane 1,1-Ethanediol diacetate
Identifiers
CAS Number	542-10-9  Y
3D model (JSmol)	Interactive image
ChemSpider	21106538
ECHA InfoCard	100.008.001
PubChem CID	222536
UNII	KL1S8V6W25  Y
CompTox Dashboard (EPA)	DTXSID1027188
InChI 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
SMILES CC(OC(=O)C)OC(=O)C
Properties
Chemical formula	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

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

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. Roscher, Günter (2000). "Vinyl Esters". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a27_419. ISBN   978-3-527-30385-4.
2. GB Patent 238825A 'Process of Manufacture of Acetic Anhydride and Aldehyde'