Acetophenone

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19-20 °C

202 °C

Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances.[1]

Contents

Production

Acetophenone can be obtained by a variety of methods. In industry, acetophenone is recovered as a by-product of the oxidation of ethylbenzene, which mainly gives ethylbenzene hydroperoxide for use in the production of propylene oxide.[1]

Uses

Precursor to resins

Commercially significant resins are produced from treatment of acetophenone with formaldehyde and base. The resulting polymers are conventionally described with the formula [(C6H5C(O)CH]x(CH2)x}n, resulting from aldol condensation. These materials are components of coatings and inks. Modified acetophenone-formaldehyde resins are produced by the hydrogenation of the aforementioned ketone-containing resins. The resulting polyol can be further crosslinked with diisocyanates.[1] These modified resins are again found in coatings, inks, as well as adhesives.

Precursor to styrene

In instructional laboratories, acetophenone is converted to styrene in a two step process that illustrates the reduction of carbonyls and the dehydration of alcohols:

A similar process is used industrially but the hydrogenation step to 1-phenylethanol is done over a copper catalyst.[1]

Use in pharmaceutical and related areas

Acetophenone is a raw material for the synthesis of some pharmaceuticals[2] [3] and is also listed as an approved excipient by the U.S. FDA.[4] In a 1994 report released by five top cigarette companies in the U.S., acetophenone was listed as one of the 599 additives to cigarettes.[5]

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