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| Acetophenone | |
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| IUPAC name | 1-phenylethanone |
| Other names | Phenyl methyl ketone |
| Identifiers | |
| CAS number | 98-86-2 |
| SMILES |
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| InChI |
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| Properties | |
| Molecular formula | C8H8O |
| Molar mass | 120.15 g mol−1 |
| Density | 1.028 g/cm³ |
| Melting point |
19-20 °C |
| Boiling point |
202 °C |
| Hazards | |
| MSDS | External MSDS |
| NFPA 704 |
 2
0
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| Flash point | 77 °C |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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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
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Production
Acetophenone can be obtained by a variety of methods. In industry, acetophenone is recovered as a by-product of the phenol-acetone synthesis in the cumene oxidation process.1 It can also be obtained by the dry distillation of a mixture of the calcium salts of acetic and benzoic acids.
Uses
Flavors and fragrances
Acetophenone is used to create fragrances that resemble almond, cherry, honeysuckle, jasmine, and strawberry, and it occurs naturally in many foods. It is used in chewing gum. At one time it was used as a hypnotic under the name of "hypnone." 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.2
Derivatives
Hydrogenation of acetophenone gives 1-phenylethanol, which is used in perfumes.
Commercially significant resins are produced from treatment of acetophenone with variable amounts of 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.
Natural occurrence
Acetophenone occurs naturally in many foods including apple, cheese, apricot, banana, beef, and cauliflower.
References
- ^ a b c Hardo Siegel, Manfred Eggersdorfer “Ketones” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002, Wienheim. doi:10.1002/14356007.a15_077
- ^ "What's in a cigarette?". Retrieved on 2006-05-31.
