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| Names | |||
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| Preferred IUPAC name 1-Phenylethanone[1] | |||
| Other names Acetophenone Phenylethanone Methyl phenyl ketone | |||
| Identifiers | |||
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3D model (JSmol) | |||
| Abbreviations | ACP | ||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| DrugBank |
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| ECHA InfoCard | 100.002.462 | ||
| EC Number |
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| KEGG |
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| RTECS number |
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| UNII | |||
| UN number | 1993 | ||
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| Properties | |||
| C8H8O | |||
| Molar mass | 120.151 g·mol−1 | ||
| Density | 1.028 g/cm3 | ||
| 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 | |||
| −72.05·10−6 cm3/mol | |||
| Hazards | |||
| GHS labelling: | |||
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| Warning | |||
| H302,H319 | |||
| P264,P270,P280,P301+P312,P305+P351+P338,P330,P337+P313,P501 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 77 °C (171 °F; 350 K) | ||
| Safety data sheet (SDS) | MSDS | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Acetophenone is theorganic compound with theformula C6H5C(O)CH3. It is the simplest aromaticketone. This colorless, viscous liquid is a precursor to usefulresins and fragrances.[2]
Acetophenone is formed as a byproduct of thecumene process, the industrial route for the synthesis ofphenol andacetone. In the Hock rearrangement ofisopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternaterearrangement 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.[2]
Acetophenone is also generated fromethylbenzene hydroperoxide. Ethylbenzene hydroperoxide is primarily converted to1-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.[2]
Commercially significantresins are produced from treatment of acetophenone withformaldehyde and abase. The resultingcopolymers are conventionally described with the formula[(C6H5COCH)x(CH2)x]n, resulting fromaldol condensation. These substances are components ofcoatings andinks. Modified acetophenone-formaldehyde resins are produced by the hydrogenation of the aforementioned ketone-containing resins. The resultingpolyol can be further crosslinked withdiisocyanates.[2] The modified resins are found in coatings, inks andadhesives.
Acetophenone is an ingredient in fragrances that resemblealmond,cherry,honeysuckle,jasmine, andstrawberry. It is used in chewing gum.[3] It is also listed as an approvedexcipient by the U.S. FDA.[4] More common as a fragrance is the closely related4-methylacetophenone.[5]
In instructional laboratories,[6] acetophenone is converted tostyrene in a two-step process that illustrates the reduction of carbonyls usingsodium borohydride and thedehydration of alcohols:
A similar two-step process is used industrially, but reduction step is performed byhydrogenation over acopper chromitecatalyst:[2]
Beingprochiral, acetophenone is also a popular test substrate for asymmetrichydrogenation experiments.
Acetophenone is used for the synthesis of many pharmaceuticals.[7][8]
Acetophenone occurs naturally in many foods includingapple,cheese,[9]apricot,banana,[10]beef, andcauliflower.
In the late 19th and early 20th centuries, acetophenone was used in medicine.[11] It was marketed as ahypnotic andanticonvulsant under brand name Hypnone. The typical dosage was 0.12 to 0.3 milliliters.[12] It was considered to have superior sedative effects to bothparaldehyde andchloral hydrate.[13] In humans, acetophenone is metabolized tobenzoic acid,carbonic acid, andacetone.[14]Hippuric acid occurs as an indirect metabolite and its quantity in urine may be used to confirm acetophenone exposure,[15] although other substances, liketoluene, also induce hippuric acid in urine.[16]
TheLD50 is 815 mg/kg (oral, rats).[2] Acetophenone is currently listed as a Group Dcarcinogen indicating that there is no evidence at present that it causes cancer in humans.
The names acetophenone and benzophenone are retained only for general nomenclature, but no substitution is allowed.
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