Hydroformylation of unsaturated fatty acids

When hydroformylation of unsaturated fatty materials is done with rhodium‐triphenyl phosphine (or phosphite) catalysts, a number of advantages become apparent compared to cobalt carbonyl‐catalyzed reactions. With rhodium, the reaction can be carried out (a) at pressures as low as 200 psi, (b) at each double bond location in a polyunsaturated fatty acid, and (c) in high yield and conversion. Solubilized catalyst can be recovered from distillation residue and readsorbed on spent catalyst support by thermal treatment in a rotary kiln. The reconstituted catalyst is more active than the original catalyst and can be recycled indefinitely at a relatively low cost. Recently developed supports for “homogeneous” catalysis may make catalyst recovery even more effective. Acetalation, oxidation with air to polycarboxylic acids and catalytic hydrogenation to hydroxymethyl compounds can be done easily and in high yield on mono‐, di‐ and triformyl derivatives alike. Other reactions investigated for monoformyl fatty esters include reductive amination to form aminomethyl derivatives and Tollen's condensation with formaldehyde to form geminal, bis ‐hydroxymethyl compounds. although the Northern Center has carried out some basic investigations on the hydroformylation reaction and on the chemistry of the hydroformylated products, there is a great deal more that can be done with regard to synthesis of new compounds and development of new applications.