Amines from aldehydes derived from the ozonization of soybean esters

Abstract

AbstractInvestigations were carried out on reductive amination of caproaldehyde, pelargonaldehyde and azelaaldehydate esters, obtainable from ozonolysis of soybean oil products, with ammonia and hydrogen in the presence of nickel catalyst. A solvent system giving good yields of primary amine while suppressing amide formation was devised. Excess ammonia and homogeneous solutions suppressed secondary amine formation. Nonpolar solvents suppressed ammonolysis. Optimum conditions for reaction varied with the aldehyde.Excellent yields of hexylamine (91%), nonylamine (90%), methyl 9‐aminononanoate (92%) and butyl 9‐aminononanoate (93%) were obtained from caproaldehyde, pelargonaldehyde, methyl azelaaldehydate and butyl azelaaldehydate, respectively, when aminated in anhydrous ammonia and either cyclohexane or methyl cyclohexane.