From Wikipedia, the free encyclopedia
|Preferred IUPAC name
Methyl phenyl ketone
|3D model (Jmol)||Interactive image
|Molar mass||120.15 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|
EU classification (DSD)
|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 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.
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.
Precursor to resins
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. These modified resins are again found in coatings, inks, as well as 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. 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.
- C6H5CH(OH)CH3 → C6H5CH=CH2 + H2O
Acetophenone is used for the synthesis of many pharmaceuticals, for example: pyrrobutamine, dextropropoxyphene, trihexyphenidyl, pridinol, aspaminol, Cycrimine, Biperiden, Procyclidine, acifran, Amixetrine, Mesuximide, and Benmoxin. Allegedly also for phenylpropanolamine (note: in this case it is actually propiophenone not PhAc).
Mannich reaction with dimethylamine and formaldehyde was described. This is used to prepare 1-chloro-1-phenyl-3-dimethylaminopropane, which is used to prepare such antidepressants as Ansoxetine, fluoxetine, atomoxetine, and nisoxetine. Using diethylamine instead gives the diethyl analog.
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.
The LD50 is 815 mg/kg (oral, rats). 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.
- 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-FP001. ISBN 978-0-85404-182-4.
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- Burdock, George A. (2005), Fenaroli's Handbook of Flavor Ingredients (5th ed.), CRC Press, p. 15, ISBN 0-8493-3034-3
- "Inactive Ingredient Search for Approved Drug Products".
- "What's in a cigarette?". Archived from the original on 23 May 2006. Retrieved 2006-05-31.
- Sittig, Marshall (1988). Pharmaceutical Manufacturing Encyclopedia. pp. 39,177. ISBN 978-0-8155-1144-1.
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- Maxwell, Charles E. (1943). "β-Dimethylaminopropiophenone Hydrochloride". Org. Synth. 23: 30.
- Müller-Schwarze, D.; 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.
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- Bartholow, Roberts (1908). A Practical Treatise on Materia Medica and Therapeutics. Appleton & Co.
- Norman, Conolly (1887). "Cases illustrating the sedative effects of aceto-phenone". Journal of Mental Science. 32: 519.
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- CID 7410 from PubChem
- The Netherlands Center for Occupational Diseases (NCvB): toluene (Dutch)