Acetophenone

Chembox new
Name = Acetophenone
ImageFileL1 = Acetophenone-2D-skeletal.png ImageSizeL1 = 120 px
ImageFileR1 = Acetophenone-3D-balls.png ImageSizeR1 = 120 px
IUPACName = 1-phenylethanone
OtherNames = Phenyl methyl ketone
Section1 = Chembox Identifiers
CASNo = 98-86-2
SMILES = O=C(C)C1=CC=CC=C1
InChI=1/C8H8O/c1-7(9) 8-5-3-2-4-6-8/h2-6H,1H3
Section2 = Chembox Properties
C=8|H=8|O=1
Density = 1.028 g/cm³
MeltingPt = 19-20 °C
BoilingPt = 202 °C
Section7 = Chembox Hazards
FlashPt = 77 °C
NFPA-F = 2
NFPA-R =

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.Hardo Siegel, Manfred Eggersdorfer “Ketones” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002, Wienheim. DOI|10.1002/14356007.a15_077]

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. 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. [cite web
url =http://quitsmoking.about.com/cs/nicotineinhaler/a/cigingredients.htm
title =What's in a cigarette?
accessdate =2006-05-31]

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. 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

* [http://quitsmoking.about.com/cs/nicotineinhaler/g/term_4add.htm Acetophenone]
* [http://ptcl.chem.ox.ac.uk/MSDS/AC/acetophenone.html Safety data for acetophenone]