Isophorone

Isophorone
IUPAC name 3,5,5-Trimethyl-2-cyclohexene-1-one
Other names 1,1,3-Trimethyl-3-cyclohexene-5-one Isoforone Isoacetophorone
Identifiers
CAS number	78-59-1 Y
PubChem	6544
ChemSpider	6296 Y
KEGG	C14743 Y
Jmol-3D images	Image 1
SMILES O=C1\C=C(/CC(C)(C)C1)C
InChI InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3 Y Key: HJOVHMDZYOCNQW-UHFFFAOYSA-N Y InChI=1/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3 Key: HJOVHMDZYOCNQW-UHFFFAOYAC
Properties
Molecular formula	C9H14O
Molar mass	138.21 g/mol
Density	0.92 g/cm3
Melting point	-8.1 °C
Boiling point	215.2 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

Production

Isophorone can be manufactured by catalyzed self-condensation of acetone. Mesityl oxide is the initial product of the self-aldol condensation of acetone. The mesityl oxide formed can react further with acetone 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.

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.

See also

• Phorone