Acetophenone is the organic compound with the formula C6H5C(O)CH3 (also represented by the pseudoelement symbols PhAc or BzMe). It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances.
|Preferred IUPAC name
Methyl phenyl ketone
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||120.151 g·mol−1|
|Melting point||19–20 °C (66–68 °F; 292–293 K)|
|Boiling point||202 °C (396 °F; 475 K)|
|5.5 g/L at 25 °C|
12.2 g/L at 80 °C
|Safety data sheet||MSDS|
|GHS Signal word||Warning|
|P264, P270, P280, P301+312, P305+351+338, P330, P337+313, P501|
|NFPA 704 (fire diamond)|
|Flash point||77 °C (171 °F; 350 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Acetophenone is recovered as a by-product of the oxidation of ethylbenzene to ethylbenzene hydroperoxide. Ethylbenzene hydroperoxide is an intermediate in the commercial production of propylene oxide via the propylene oxide - styrene co-product process. Ethylbenzene hydroperoxide is primarily converted to 1-phenylethanol (α-methylbenzyl alcohol) in the process with a small amount of by-product acetophenone. Acetophenone is recovered or hydrogenated to 1-phenylethanol which is then dehydrated to produce styrene.
Precursor to resinsEdit
Commercially significant resins are produced from treatment of acetophenone with formaldehyde and a base. The resulting copolymers are conventionally described with the formula [(C6H5COCH)x(CH2)x]n, resulting from aldol condensation. These substances 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. The modified resins are found in coatings, inks and adhesives.
Acetophenone is an ingredient in fragrances that resemble almond, cherry, honeysuckle, jasmine, and strawberry. It is used in chewing gum. It is also listed as an approved excipient by the U.S. FDA.
- C6H5C(O)CH3 + H2 → C6H5CH(OH)CH3
Acetophenone occurs naturally in many foods including apple, cheese, apricot, banana, beef, and cauliflower. It is also a component of castoreum, the exudate from the castor sacs of the mature beaver.
In the late 19th and early 20th centuries, acetophenone was used in medicine. It was marketed as a hypnotic and anticonvulsant under brand name Hypnone. The typical dosage was 0.12 to 0.3 milliliters. It was considered to have superior sedative effects to both paraldehyde and chloral hydrate. In humans, acetophenone is metabolized to benzoic acid, carbonic acid, and acetone. Hippuric acid occurs as an indirect metabolite and its quantity in urine may be used to confirm acetophenone exposure, although other substances, like toluene, also induce hippuric acid in urine.
- Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 723. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
The names acetophenone and benzophenone are retained only for general nomenclature, but no substitution is allowed.
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