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Selective hydroformylation of polyunsaturated fats with a rhodium‐triphenylphosphine catalyst
Author(s) -
Frankel E. N.,
Thomas F. L.
Publication year - 1972
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/bf02545129
Subject(s) - rhodium , triphenylphosphine , hydroformylation , linseed oil , catalysis , chemistry , fraction (chemistry) , organic chemistry , polyunsaturated fatty acid , medicinal chemistry , fatty acid
Soybean, safflower and linseed oils and their methyl esters were effectively hydroformylated with a rhodium and triphenylphosphine catalyst system. The product from safflower methyl esters, hydroformylated at 100 C and 1000 psi synthesis gas (H 2 + CO), proved to be a mixture of formylstearate, formyloleate and diformylstearate. At 150 C and 15 00 psi synthesis gas the formyloleate was hydrogenated and the product formed was a mixture of mono‐ and diformylstearates. The unsaturated monoformyl fraction (100 C) was tentatively identified as a mixture consisting mainly of methyl 9(10)‐formyl‐ cis ‐12‐and methyl 12(13)‐formyl‐ cis ‐9‐octadecenoates. The saturated monoformyl fraction (150 C) was a more complex isomeric mixture of methyl formylstearate. The diformyl fractions from hydroformylated safflower and linseed esters were identified as mixtures consisting mainly of 9,12‐(10,13)‐ and 10,12‐(11,13)‐diformyloctadecanoates. When hydroformlyation of polyunsaturated fats was interrupted, cis ‐unsaturated formyl oils resulted.