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Alcohols from ozonolysis products of unsaturated fatty esters
Author(s) -
Pryde E. H.,
Thierfelder C. M.,
Cowan J. C.
Publication year - 1976
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/bf02635955
Subject(s) - ozonolysis , chemistry , catalysis , organic chemistry , hydrolysis , alkyl , yield (engineering) , solvent , noble metal , catalytic hydrogenation , metal , materials science , metallurgy
1‐Nonanol and alkyl 9‐hydroxynonanoates were more readily prepared by hydrogenation of the respective isolated aldehydes than by direct hydrogenation of products from reductive ozonolysis of oleate esters. Hydrogenation with nickel catalysts and aprotic solvents reduced the isolated aldehydes in good yield with a minimum of side reactions. Although the noble metal catalyst and hydroxylic solvent systems frequently used in similar reductions were also effective, they required a promoter that fortuitously catalyzed hydrolysis of acetals that formed during hydrogenation. Direct hydrogenation of the ozonolysis products resulted in side reactions and a mixture of products difficult to separate.