Acetophenone
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| Names | |||
|---|---|---|---|
| IUPAC name
1-phenylethanone | |||
| Other names
Methyl phenyl ketone; Phenylethanone; Acetophenone | |||
| Identifiers | |||
98-86-2  | |||
| Abbreviations | ACP | ||
| ChEBI | CHEBI:27632 | ||
| ChEMBL | ChEMBL274467 | ||
| ChemSpider | 7132 | ||
| DrugBank | DB04619 | ||
| Jmol 3D model | Interactive image Interactive image | ||
| KEGG | C07113 | ||
| PubChem | 7410 | ||
| UNII | RK493WHV10 | ||
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| Properties | |||
| C8H8O | |||
| Molar mass | 120.15 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 | |||
| Hazards | |||
| Safety data sheet | MSDS | ||
| EU classification (DSD) |
 Xn | ||
| NFPA 704 | |||
| 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). | |||
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| Infobox references | |||
Acetophenone is the organic compound with the formula C6H5C(O)CH3 (also represented by the letters PhAc or BzMe), is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances.[1]
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 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.[1] These modified resins are again found in coatings, inks, as well as adhesives.
Use in pharmaceutical and related areas
Acetophenone is used for the synthesis of many pharmaceuticals, for example:
Dextropropoxyphene, fluoxetine, atomoxetine, nisoxetine, trihexyphenidyl, Cycrimine, Biperiden, Procyclidine and acifran.
Allegedly also for phenylpropanolamine.[2][3] (note: in this case it is actually propiophenone not PhAc)
Another use can be in the synthesis of benzoylacetone.[4]
Niche uses
Acetophenone is an ingredient in fragrances that resemble almond, cherry, honeysuckle, jasmine, and strawberry. It is used in chewing gum.[5] It is also listed as an approved excipient by the U.S. FDA.[6] 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.[7]
Laboratory reagent
In instructional laboratories, acetophenone is converted to styrene in a two-step process that illustrates the reduction of carbonyls and the dehydration of alcohols:
- 4 C6H5C(O)CH3 + NaBH4 + 4 H2O → 4 C6H5CH(OH)CH3 + NaOH + B(OH)3 → C6H5CH=CH2
A similar process is used industrially but the hydrogenation step to 1-phenylethanol is done over a copper catalyst.[1]
- C6H5CH(OH)CH3 → C6H5CH=CH2 + H2O
Being prochiral, acetophenone is also a popular test substrate for asymmetric hydrogenation experiments.
Natural occurrence
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.[8]
Pharmacology
In the late 19th and early 20th centuries, acetophenone was used in medicine.[9] It was marketed as a hypnotic and anticonvulsant under brand name Hypnone. The typical dosage was 0.12 to 0.3 milliliters.[10] It was considered to have superior sedative effects to both paraldehyde and chloral hydrate.[11] In humans, acetophenone is metabolized to benzoic acid, carbonic acid, and acetone.[12] Hippuric acid occurs as an indirect metabolite and its quantity in urine may be used to confirm acetophenone exposure.[13]
Toxicity
The LD50 is 815 mg/kg (oral, rats).[1] Acetophenone is currently listed as a Group D carcinogen (Not Classifiable as to Human Carcinogenicity), indicating that it does not produce carcinogenic effects in humans, although no studies on humans have ever been conducted on acetophenones' carcinogenic potential. Studies have shown that acetophenone causes chromosomal damage in hamsters.[13]
References
- 1 2 3 4 5 Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002, Wienheim. doi:10.1002/14356007.a15_077
- ↑ Sittig, Marshall (1988). Pharmaceutical Manufacturing Encyclopedia. pp. 39,177. ISBN 978-0-8155-1144-1.
- ↑ Gadamasetti, Kumar; Tamim Braish (2007). Process Chemistry in the Pharmaceutical Industry, Volume 2. pp. 142–145. ISBN 978-0-8493-9051-7.
- ↑ http://www.prepchem.com/synthesis-of-benzoylacetone/
- ↑ Burdock, George A. (2005), Fenaroli's Handbook of Flavor Ingredients (5th ed.), CRC Press, p. 15, ISBN 0-8493-3034-3
- ↑ http://www.accessdata.fda.gov/scripts/cder/iig/index.cfm
- ↑ "What's in a cigarette?". Archived from the original on 23 May 2006. Retrieved 2006-05-31.
- ↑ Müller-Schwarze, D and Houlihan, P.W. (April 1991). "Pheromonal activity of single castoreum constituents in beaver, Castor canadensis". Journal of Chemical Ecology 17 (4): 715–34. doi:10.1007/BF00994195. PMID 24258917.
- ↑ The Merck Index, 12th Edition
- ↑ Bartholow, Roberts (1908). A Practical Treatise On Materia Medica And Therapeutics. Appleton & Co.
- ↑ Norman, Conolly "Cases illustrating the sedative effects of aceto-phenone." Journal of Mental Science, Vol 32, p 519. 1887.
- ↑ "Hypnone - The new hypnotic". J Am Med Assoc. 5 (632). 1885. doi:10.1001/jama.1885.02391220016006.
- 1 2 CID 7410 from PubChem
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