The first attempts to prepare ricinoleic acid were made by
Friedrich Krafft in 1888.[3]
Use
Sebacic acid ((CH2)8(CO2H)2), which is used in preparing certain
nylons, is produced by cleavage of ricinoleic acid. The coproduct is
2-octanol.[4][5] The mechanism of the base-induced cleavage is proposed to proceed by initial dehydrogenation of the secondary alcohol, affording the ketone. The resulting
α,β-unsaturated ketone undergoes
retroaldol reaction, resulting in lysis of the C-C bond.[6]
Lesquerolic acid, a similar chemical, which could be described as ricinoleic acid with -CH2-CH2- group inserted between carboxyl group and the double bond.
^Roger Adams, C. S. Marvel (1921). "Methyl-n-hexylcarbinol". Organic Syntheses. 1: 61.
doi:
10.15227/orgsyn.001.0061.
^Diamond, M. J.; Binder, R. G.; Applewhite, T. H. (1965). "Alkaline cleavage of hydroxy unsaturated fatty acids. I. Ricinoleic acid and lesquerolic acid". Journal of the American Oil Chemists' Society. 42 (10): 882–884.
doi:
10.1007/BF02541184.
S2CID85036911.