Isophorone

Isophorone
Isophorone
Chemical name	3,5,5-Trimethyl-2-cyclohexen-1-one
Other names	1,1,3-Trimethyl-3-cyclohexene-5-one Isoforone Isoacetophorone
Chemical formula	C9H14O
Molecular mass	138.21 g/mol
CAS number	[78-59-1]
Density	0.92 g/cm3
Melting point	-8.1 °C
Boiling point	215.2 °C
SMILES	O=C1CC(C)(C)CC(C)=C1
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.

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 acetone formed can react further with mesityl oxide in a Michael reaction to eventually obtain the six-membered ring of isophorone. The yield of the two compounds depends on the reaction conditions.

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History

The use of isophorone as a solvent resulted from the search for ways to dispose of or recycle acetone, which was 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.

References

de:Isophoron