Premium
A novel technique for the preparation of secondary fatty amides II: The preparation of ricinoleamide from castor oil
Author(s) -
Piazza George J.,
Bistline Raymond G.,
Bilyk Alexander,
Feairheller Stephen H.,
Haas Michael J.
Publication year - 1993
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02641011
Subject(s) - ricinoleic acid , castor oil , amide , chemistry , organic chemistry , butylamine , fatty acid , glycerol , triethylenetetramine , amine gas treating
The butyl amide of ricinoleic acid (N‐ n ‐butyl‐12‐hydroxy‐(9 Z )‐octadecenamide) was prepared from a neat mixture of castor oil and n ‐butylamine (fatty ester/amine molar ratio, 1:1.3). No catalyst was required. The identity and purity of the amide was assessed by thin‐layer chromatography and confirmed by elemental analysis and by infrared and C 13 nuclear magnetic resonance spectroscopy. High product yields were achieved at 45 and 65°C in 48 and 20 h, respectively. The reaction was inhibited by the addition of trimethylpentane and dioxane, but not by water. An attempt was made to prepare the amide from methyl ricinoleate, 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 primarily of the glycerol esters of hydroxylated fatty acids indicates that the described procedure has industrial utility.