Crotonaldehyde is a chemical compound with the chemical formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common. This Tears liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. .
Production and reactivity
Crotonaldehyde is produced by the aldol condensation of
acetaldehyde:
- 2 CH3CHO → CH3CH=CHCHO + H2O
Crotonaldehyde is a multifunctional molecule that exhibits diverse reactivity. It is a prochiral dienophile.
Uses
It is a precursor to many fine chemicals. A prominent industrial example is the crossed aldol condensation with
diethyl ketone to give trimethylcyclohexenone, this can be easily converted to trimethylhydroquinone, which is a precursor to the
vitamin E.
Other derivatives include crotonic acid, 3-methoxybutanol and the food preservative
Sorbic acid. Condensation with two equivalents of
urea gives a
pyrimidine derivative that is employed as a controlled-release fertilizer.
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Safety
Crotonaldehyde is a potent irritant even at the ppm levels. It is not very toxic, with an of 174 mg/kg (rats, oral).[
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See also
External links
