Acetophenone

[2] Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone.

In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate: The cumene process is conducted on such a large scale that even the small amount of acetophenone by-product can be recovered in commercially useful quantities.

Ethylbenzene hydroperoxide is primarily converted to 1-phenylethanol (α-methylbenzyl alcohol) in the process with a small amount of by-product acetophenone.

[4] In instructional laboratories,[5] acetophenone is converted to styrene in a two-step process that illustrates the reduction of carbonyls using sodium borohydride and the dehydration of alcohols: A similar two-step process is used industrially, but reduction step is performed by hydrogenation over a copper chromite catalyst:[2] Being prochiral, acetophenone is also a popular test substrate for asymmetric hydrogenation experiments.

[6][7] Acetophenone occurs naturally in many foods including apple, cheese, apricot, banana, beef, and cauliflower.

[2] Acetophenone is currently listed as a Group D carcinogen indicating that there is no evidence at present that it causes cancer in humans.

Skeletal formula of the acetophenone molecule
Skeletal formula of the acetophenone molecule
Ball-and-stick model of the acetophenone molecule
Ball-and-stick model of the acetophenone molecule
Space-filling model of the acetophenone molecule
Space-filling model of the acetophenone molecule
sample of acetophenone
sample of acetophenone
NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code