Isophorone
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| Isophorone[1] | |
|---|---|
 |
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| 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 is also occurs naturally in cranberries.[2]
Contents |
[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 in a Michael reaction to eventually obtain the six-membered ring of isophorone. 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 was 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.
[edit] References
- ^ Merck Index, 13th Edition, 5215.
- ^ a b Chronic Toxicity Summary
- ^ U.S. Patent 5849957
- ^ Isophorone history at Degussa
