Derivatives of long chain fatty acids as lubricant components

Soaps ofcis-9,10-epiminostearic acid have been synthesized and tested as components of lubricating greases. The lithium, sodium and potassium soaps were obtained by the reaction ofβ-iodocarbamates with the proper alkali metal hydroxides in the ring closure step of the iodine isocyanate (INCO) procedure for the synthesis of internal aziridines. The soaps of other metals, namely barium, lead, aluminum and indium, were prepared from the alkali metal epiminostearates by metathetical reactions. As a result of this method of preparation, the aluminum and the indium soaps were isolated as the dicarboxylates rather than as the tricarboxylates. For the purpose of comparison a sample of lithium 9,10-epiminostearate was also prepared from theβ-chlorocarbamate obtained by the addition of dichlorourethane (DCU) to methyl oleate. Since DCU addition is nonstereospecific, the soap obtained in this preparation was a mixture ofcis- andtrans-aziridines. Evaluation of the metal soaps as grease thickeners was made. The lithium derivative showed considerable promise as thickener having additional desirable properties. Presented at the AOCS-ISF World Congress, Chicago, September 1970. E. Market. Nutr. Res. Div. ARS, USDA.