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Isophorone

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Isophorone
Isophorone
Names
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.024 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3Key: HJOVHMDZYOCNQW-UHFFFAOYSA-N
  • InChI=1/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3Key: HJOVHMDZYOCNQW-UHFFFAOYAC
SMILES
  • O=C1\C=C(/CC(C)(C)C1)C
Properties
Chemical formula C9H14O
Molar mass 138.21 g/mol
Density 0.92 g/cm
Melting point -8.1 °C
Boiling point 215.2 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

References

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