Isophorone

Chembox new
Name = Isophorone
Reference = ["Merck Index", 13th Edition, 5215.]
ImageFile = Isophorone.png ImageName = Isophorone
IUPACName = 3,5,5-Trimethyl-2-cyclohexen-1-one
OtherNames = 1,1,3-Trimethyl-3-cyclohexene-5-one
Isoforone
Isoacetophorone
Section1 = Chembox Identifiers
CASNo = 78-59-1
PubChem = 6544
SMILES = O=C1CC(C)(C)CC(C)=C1
Section2 = Chembox Properties
Formula = C₉H₁₄O
MolarMass = 138.21 g/mol
Density = 0.92 g/cm³
MeltingPt = -8.1 °C
BoilingPt = 215.2 °C

Isophorone is an α,β-Unsaturated cyclic ketone, a colorless to yellowish liquid with characteristic smell, that is used as a solvent and as an intermediate in organic synthesis. Isophorone also occurs naturally in cranberries. [http://www.oehha.ca.gov/air/chronic_rels/pdf/isophorone.pdf Chronic Toxicity Summary] ]

Production

Isophorone can be manufactured by catalyzed self-condensation of acetone. [ US patent|5849957]
Mesityl oxide is the initial product of the self-aldol condensation of acetone. The acetone formed can react further with mesityl oxide via a Michael reaction and subsequent intramolecular aldol condensation to eventually obtain the six-membered ring of isophorone. This is an example of the Robinson annulation. The yield of the two compounds depends on the reaction conditions.

History

The use of isophorone as a solvent resulted from the search for ways to dispose of or recycle acetone, which is a waste product of phenol synthesis by the Hock method. [ [http://www.degussa-history.com/geschichte/en/inventions/isophorone/ Isophorone history at Degussa] ]

Uses

Isophorone is used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings and pesticides. It is also used as a chemical intermediate and as an ingredient in wood preservatives and floor sealants.

References