Reaction of dichlorocarbene with fats and oils

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Abstract
Dichlorocarbene was generated in the presence of lard, olive, safflower, tung and menhaden oil. When solutions of fats or oils in ethyl trichloroacetate were mixed with sodium methoxide inn‐heptane at 2C, unsaturated components were transformed in high conversion to dichlorocyclopropane derivatives; fats were converted to methyl‐and‐ethyl esters (90%) or appeared as glycerides (10%). The proportion of dichlorocyclopropane rings was the same in the glycerides as in the ester products. The reactivity of safflower oil required metered addition of reactants at 25舑55C.Properties were measured on dichlorocyclo‐propanoid fatty esters freed from glycerides but containing saturated esters. Chlorine content ranged from 12舑33%. Compatibility with silicone oils was substantially improved. Viscosities and densities increased with chlorine content. Viscosity indices were 135,150,49,67 and 79 for products from lard, olive, safflower, tung and menhaden oil.Dichlorocarbene could be generated without alcoholysis of glycerides by decomposition of sodium trichloroacetate. This gave dichlorocyclopropanes from safflower oil unsaturates in 50% conversion, but failed with lard.Analyses were performed by TLC, argentation and GLC.

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