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Homogeneous catalytic hydrogenation of unsaturated fats: Iron Pentacarbonyl
Author(s) -
Frankel E. N.,
Peters Helen M.,
Jones E. P.,
Dutton H. J.
Publication year - 1964
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/bf03024644
Subject(s) - isomerization , chemistry , degree of unsaturation , linolenate , catalysis , double bond , stearate , organic chemistry , homogeneous catalysis , iron pentacarbonyl , conjugated system , homogeneous , hydroformylation , rhodium , fatty acid , physics , thermodynamics , polymer
Iron pentacarbonyl is an effective homogeneous catalyst for the reduction of polyunsaturated fats. Hydrogenation of soybean oil and its methyl esters has been achieved at 180C, hydrogen pressures of 100‐1,000 psi, and 0.05舑0.5 molar concentrations of catalyst. Analyses of partially reduced products show considerable isomerization of double bonds, reduction of linolenate and linoleate with little or no increase in stearate, and accumulation of cis,trans‐ and trans, trans‐conjugated dienes, and isolated trans monoenes. The unreduced trienes include diene conjugated fatty esters. The nonconjugated dienes contain large amounts of trans and nonalkali conjugatable unsaturation. Considerable scattering of double bonds is evident in different fractions between the C 4 and C 16 positions. Complex formation between iron carbonyl and unsaturated fats is also indicated. The course of the homogeneous hydrogenation catalyzed by iron pentacarbonyl appears similar to the heterogeneous catalytic reaction. Metal carbonyls are well known for their isomerizing effects and their ability to form stable complexes with olefins. These homogeneous complexes provide suitable model systems to study the mechanism of catalytic hydrogenation of fats.