Secondary products from high pressure hydrogenation of crambe oil

• Published in: Journal of the American Oil Chemists' Society
• Main Authors: Spencer, G. F., Nieschlag, H. J., Rothfus, J. A.
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 1974
• Subjects: Adkins; Sperm whale
• Online Access: http://dx.doi.org/10.1007/bf02635153; https://onlinelibrary.wiley.com/doi/full/10.1007/BF02635153

Abstract Hydrogenation of crambe oil, mainly an α,α’‐dierucoyl triglyceride, in the presence of cadmium promoted copper‐chromite provides long chain waxes being sought as sperm whale oil replacements. Gas liquid chromatography and gas chromatography‐mass spectrometry analyses of secondary products indicate, however, that reduction proceeds rather differently from Adkins‐type hydrogenations of triglycerides over copper‐chromium oxide catalysts. Monoand diunsaturated alkenes ranging from C 16 ‐C 24 , odd chain lengths included, constitute ca. 1% of the product. Esters of crambe acids with methyl, ethyl, n‐propyl, and isopropyl alcohols account for less than 5%. These alcohols and traces of 1,2‐propanediol from the hydrogenolysis of glycerol occur in either the head gas or the reaction mixture or both. In contrast to published results for Adkins‐type hydrogenations of triglycerides, n‐propyl alcohol is far more abundant than isopropyl alcohol or 1,2‐propanediol. Isopropyl esters of C‐18 acids are not present, and those of C‐22 acids constitute no more than 2% of the total esters. Low proportion of isopropyl esters and enrichment of C‐22 acids in the secondary products compared with C‐18 acids suggest that the acyl substituent at the β‐position of glycerol is eliminated during hydrogenation of crambe oil with a Cd−Cu−Cr catalyst.