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Amines from aldehydes derived from the ozonization of soybean esters
Author(s) -
Anders D. E.,
Pryde E. H.,
Cowan J. C.
Publication year - 1965
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02541167
Subject(s) - chemistry , anhydrous , cyclohexane , amine gas treating , organic chemistry , ammonia , aldehyde , solvent , catalysis , soybean oil , ozonolysis , amide , amination , reductive amination , food science
Investigations 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.