Selective hydroformylation of polyunsaturated fats with a rhodium‐triphenylphosphine catalyst

Abstract

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 (H 2 + 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.