Isophorone

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]

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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.

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.^[4]

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.

References

1. ^ Merck Index, 13th Edition, 5215.
2. ^ ^{a b} Chronic Toxicity Summary
3. ^ U.S. Patent 5,849,957 
4. ^ Isophorone history at Degussa