Fatty acids, fatty alcohols, wax esters, and methyl esters fromCrambe abyssinicaandLunaria annuaseed oils

Abstract

Crambe abyssinica andLunaria annua, members of the Cruciferae family, have seed oil glycerides containing ca. 55舑65% of C22 and C24 unsaturated fatty acids. Fatty acids were prepared by saponification; fatty alcohols, by sodium reduction of glycerides; liquid wax esters, byp‐toluenesulfonic acid‐catalyzed reaction of fatty acids with fatty alcohols; and methyl esters, by reaction of fatty acids with diazomethane. Solid hydrogenated glyceride oils and wax esters were compared with several commercial waxes. Chemical and physical constants were determined for the seed oils and their derivatives. Position of unsaturation in theCrambe fatty acids was determined by gas chromatographic analysis of the permanganate‐periodate degradation products. The major dicarboxylic acid was brassylic (C13), proving the docosenoic acid to be erucic.

Industrial uses of high erucic oils

“…Liquid waxes can be prepared from the crambe glycerides by sodium reduction to unsaturated fatty alcohols and esterification of these alcohols with crambe acids. Hydrogenation of these liquid wax esters yields a product that melts slightly higher (66-68 C) but is somewhat softer than beeswax (30). Both the solid hydrogenated crambe glycerides and the hydrogenated wax esters have properties that are comparable to many commercial waxes.…”

“…Hydrogenation of Crambe oil yields a glyceride which contains saturated fatty acids and which melts at a higher temperature than the natural product. The hydrogenated triglyceride has a glossy surface and about the same melting point as beeswax (62-65 C), but it is much harder than beeswax (30,31). Liquid waxes can be prepared from the crambe glycerides by sodium reduction to unsaturated fatty alcohols and esterification of these alcohols with crambe acids.…”

Renewable feedstocks for lubricant production

“…This requires long-chain fatty alcohols that can be transesterifi ed with LCFAs to produce a mixture of C 40 -C 42 jojoba-type wax esters. Crambe and Limnanthes seed oils, two promising agricultural raw materials, as well as honesty (Lunaria annua L.), can be converted to liquid wax esters similar to those of sperm oil [275,310,311]. Synthetic wax esters and diesters were derived from Limnanthes and partially hydrogenated Crambe seed oils using a pTSA catalyst [307].…”

Synthetic Wax Esters and Diesters from Crambe and Limnanthes Seed Oils

“…Limnanthes, though somewhat less developed as a new crop, is especially well suited for early spring production in the Pacific Northwest (Miller et al, 1964). Miwa and Wolff (1963) made alcohols from crambe oil by sodium reduction of glycerides; esterification with the corresponding acids yielded wax esters. Earlier, Adkins and his colleagues (1954) demonstrated that catalytic hydrogenolysis was a preferred method of making fatty alcohols.…”