A NOVEL TECHNIQUE FOR THE PREPARATION OF SECONDARY FATTY AMIDES II - THE PREPARATION OF RICINOLEAMIDE FROM CASTOR-OIL

The butyl amide of ricinoleic acid (N-n-butyl-12-hydroxy-(9Z)-octadece namide) was prepared from a neat mixture of castor oil and n-butylamin e (fatty ester/amine molar ratio, 1:1.3). No catalyst was required. Th e identity and purity of the amide was assessed by thin-layer chromato graphy and confirmed by elemental analysis and by infrared and C-13 nu clear magnetic resonance spectroscopy. High product yields were achiev ed at 45 and 65-degrees-C in 48 and 20 h, respectively. The reaction w as inhibited by the addition of trimethylpentane and dioxane, but not by water. An attempt was made to prepare the amide from methyl ricinol eate, rather than castor oil; even after 10 d only partial conversion was achieved. Attempts to prepare the amide from methyl-n-butylamine, rather than n-butylamine, were also unsuccessful. The ease with which secondary fatty amides can be produced from an oil that consists prima rily of the glycerol esters of hydroxylated fatty acids indicates that the described procedure has industrial utility.