isophorone

Isophorone is a cyclic enone used as an industrial chemical and solvent. Its IUPAC name is 3,5,5-trimethylcyclohex-2-en-1-one, and its molecular formula is C9H14O. The molecule consists of a cyclohexene ring bearing a ketone at the 1-position and three methyl groups at the 3 and 5 positions.

Production and applications

Isophorone is produced commercially from acetone and formaldehyde through aldol-type condensations that lead to mesityl oxide–type intermediates, which are then converted to the enone by hydrogenation and cyclization. It is a principal feedstock for the production of isophorone diisocyanate (IPDI), a widely used monomer in polyurethane coatings and elastomers. In addition to its role as a chemical intermediate, isophorone is employed as a solvent in paints, coatings, inks, and cleaning formulations. It is also used as a building block in fragrance chemistry and various resin formulations.

Properties and safety

Isophorone is typically a colorless to pale yellow liquid with a distinct, sharp odor. It is sparingly soluble in water and readily miscible with many organic solvents. The substance is flammable and can irritate eyes, skin, and the respiratory tract on exposure. Handling requires adequate ventilation, appropriate personal protective equipment, and storage away from heat sources and oxidizers.

See also

Isophorone diisocyanate; mesityl oxide; polyurethane chemistry.