Abstract
Soybean, safflower and linseed oils and their methyl esters were effectively hydroformylated with a rhodium and triphenylphosphine catalyst system. The product from safflower methyl esters, hydroformylated at 100 C and 1000 psi synthesis gas (H2 + CO), proved to be a mixture of formylstearate, formyloleate and diformylstearate. At 150 C and 15 00 psi synthesis gas the formyloleate was hydrogenated and the product formed was a mixture of mono- and diformylstearates. The unsaturated monoformyl fraction (100 C) was tentatively identified as a mixture consisting mainly of methyl 9(10)-formyl-cis-12-and methyl 12(13)-formyl-cis-9-octadecenoates. The saturated monoformyl fraction (150 C) was a more complex isomeric mixture of methyl formylstearate. The diformyl fractions from hydroformylated safflower and linseed esters were identified as mixtures consisting mainly of 9,12-(10,13)- and 10,12-(11,13)-diformyloctadecanoates. When hydroformlyation of polyunsaturated fats was interrupted,cis-unsaturated formyl oils resulted.
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Northern Marketing and Nutrition Research Division, ARS, USDA.
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Frankel, E.N., Thomas, F.L. Selective hydroformylation of polyunsaturated fats with a rhodium-triphenylphosphine catalyst. J Am Oil Chem Soc 49, 10–14 (1972). https://doi.org/10.1007/BF02545129
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DOI: https://doi.org/10.1007/BF02545129