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Crotonaldehyde

Crotonaldehyde

Crotonic aldehyde β-Methacrolein β-Methyl acrolein 2-butenal Propylene aldehyde soluble in chloroform miscible in benzene |NFPA-H = 4 |NFPA-F = 3 |NFPA-R = 2 |NFPA-S = - 1375 ppm (rat, 30 min) 519 ppm (mouse, 2 hr) 1500 ppm (rat, 30 min)

cis-3-hexenal

(E,E)-2,4-Decadienal

Crotonaldehyde is a chemical compound with the 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 lachrymatory 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. soybean oils.

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. It is a Michael acceptor. Addition of methylmagnesium chloride produces 3-penten-2-ol.

Uses

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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.

Safety

Crotonaldehyde is a potent irritant even at the ppm levels. It is not very toxic, with an of 174 mg/kg (rats, oral).

References

References

  1. ''[[Merck Index]]'', 11th Edition, '''2599'''
  2. {{PGCH. 0157
  3. {{IDLH. 123739. Crotonaldehyde
  4. R. P. Schulz. (2005). "Crotonaldehyde and Crotonic Acid".
  5. Longley Jr., R. I... (1954). "3,4-Dihydro-2-methoxy-4-methyl-2H-pyran". Org. Synth..
  6. Coburn, E. R.. (1947). "3-Penten-2-ol". Org. Synth..
  7. (2009). "Fertilizers, 2. Types".
  8. (6 December 2022). "100 Years of Vitamin E: From Discovery to Commercialization". European Journal of Organic Chemistry.
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alkenals crotyl-compounds lachrymatory-agents hazardous-materials iarc-group-2b-carcinogens
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