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Ethylidene diacetate

Ethylidene diacetate is an organic compound with the formula (CH<sub>3</sub>CO<sub>2</sub>)<sub>2</sub>CHCH<sub>3</sub>. It is a colorless liquid with a sweet, fruity odor. 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:

CH<sub>3</sub>CHO + (CH<sub>3</sub>CO)<sub>2</sub>O → (CH<sub>3</sub>CO<sub>2</sub>)<sub>2</sub>CHCH<sub>3</sub>

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

(CH<sub>3</sub>CO<sub>2</sub>)<sub>2</sub>CHCH<sub>3</sub> → CH<sub>3</sub>CO<sub>2</sub>CH=CH<sub>2</sub> + CH<sub>3</sub>CO<sub>2</sub>H

References