Homogeneous Catalysis of the Reppe Reaction with Iron Pentacarbonyl: The Production of Propionaldehyde and 1-Propanol from Ethylene

Article abstract of DOI:10.1021/ja00258a029

The Reppe hydroformylation of ethylene to produce propionaldehyde and 1-propanol in basic solutions containing Fe(CO)5 as a catalyst has been studied under carefully controlled conditions at temperatures ranging from 110 to 140 deg C.Propionaldehyde is the principal product formed when NaOH is used as the base.The rate of reaction is found to increase with ethylene concentration and is second order with respect to Fe(CO)5.The reaction is inhibited by CO.The increase in reaction rate with temperature corresponds to an activation energy of 31 kcal/mol.Infrared spectra indicate that HFe(CO)4^- and Fe(CO)5 are present in the solution phase under reaction conditions.The experimental results are shown to be consistent with a mechanism in which the rate-determining step involves a binuclear iron carbonyl derivative.The substitution of (C2H5)3N for NaOH facilitates the reduction of propionaldehyde to form 1-propanol but results in a slower rate for the overall reaction.