Stereoselective hydrogenation of model compounds and preparation of tailor‐made glycerides with chromium tricarbonyl complexes

Abstract

Abstract Studies on the mechanism of stereoselectivity of chromium tricarbonyl catalysts with model compounds provided the basis for the preparation of simulated fats. These synthetic fats were prepared by taking advantage of the unique property of chromium carbonyl complexes to catalyze hydrogenation of polyunsaturates to cis ‐monounsaturates. Oils simulating the composition of peanut oil were produced by hydrogenating soybean oil stereoselectively to an IV of 94. Simulated olive oil was made the same way from either soybean or safflower oil hydrogenated to an IV of 82–84. Stereoselective 1,4‐reduction of eleostearate in tung oil produced oils that had a high proportion of linoleate and that simulated safflower oil. The oleo‐disaturated glyceride structure of cocoa butter was also simulated by selectively hydrogenating linoleate in cottonseed oil stearines and in fractionated high‐palmitate stearines. Dilatometric and chromatographic studies showed that the cis ‐monoene‐disaturated glyceride is the major component (60–70%) in the synthetic cocoa butter.