Isophorone

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Isophorone^[1]

IUPAC name	3,5,5-Trimethyl-2-cyclohexen-1-one
Other names	1,1,3-Trimethyl-3-cyclohexene-5-one Isoforone Isoacetophorone
Identifiers
CAS number	[78-59-1]
SMILES	O=C1CC(C)(C)CC(C)=C1
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
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Isophorone is an organic compound, 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.^[2]

1 Production
2 History
3 Uses
4 References

[edit] Production

Isophorone can be manufactured by catalyzed self-condensation of acetone.^[3] 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.

[edit] 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.^[4]

[edit] Uses

Isophorone is used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings and pesticides.^[2] It is also used as a chemical intermediate and as an ingredient in wood preservatives and floor sealants.