Hydroformylation of unsaturated fatty esters

Abstract

AbstractUnsaturated fatty esters and vegetable oils were hydroformylated with H2 and CO (3500–4600 psi) and Co2(CO)8 to give fatty aldehydes at 100–110 C and fatty alcohols at 175–190 C. Yields of distillable C19 oxo products varied from 42% to 84%. Distilled products contained from 50% to 90% branched isomers and from 4% to 16% linear isomers. The proportion of linear isomers increased at higher reaction temperatures and in the presence of tributylphosphine‐cobalt carbonyl complex. Linear and branched hydroxy products were separated by silicic acid column, thin‐layer, and gas‐liquid chromatography. The linear hydroxy product (from oleate and linoleate) was identified as methyl 19‐hydroxynonadecanoate by nuclear magnetic resonance and mass spectrometry. Isomeric branched products were analyzed by mass spectrometry as the diester derivatives. They were identified as a mixture of 5‐ to 13‐carbomethoxy methyl octadecanoate.