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The synthesis of silicon oleochemicals by hydrosilylation of unsaturated fatty acid derivatives
Author(s) -
Behr Arno,
Naendrup Franz,
Obst Dietmar
Publication year - 2002
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/1438-9312(200203)104:3<161::aid-ejlt161>3.0.co;2-n
Subject(s) - hydrosilylation , chemistry , yield (engineering) , organic chemistry , linolenate , catalysis , adduct , solvent , homogeneous , double bond , fatty acid , materials science , physics , metallurgy , thermodynamics
The hydrosilylation of fatty acid esters with terminal or internal double bonds catalysed by H 2 PtCl 6 is described. The reaction was carried out with good yields at ambient pressure under mild conditions. Methyl undec‐10‐enoate was reacted with chloro‐ or alkoxyhydrosilanes giving moderate to good yields (41—77%) and even its reaction with alkylhydrosilanes produced low yields (below 20%). Under optimised conditions the hydrosilylation of methyl linoleate gave only with reactive chlorohydrosilanes acceptable yields, between 25 to 83%, of regioisomers. The hydrosilylation of methyl α‐linolenate with dimethylchlorosilane gave a mixture of regioisomeric 1:1‐ and 2:1‐hydrosilylation adducts in a total yield of 40%. The hydrosilylation of ethyl oleate did not proceed at all under our conditions. In the case of methyl undec‐10‐enoate a biphasic solvent system permitted the simple separation and reuse of the homogeneous catalyst.