Polyhydroxy fatty acids and their derivatives from plant oils |
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Authors: | B Dahlke S Hellbardt M Paetow W H Zech |
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Affiliation: | (1) Harburger Fettchemie Brinckman & Mergell GMBH, Seehafenstrasse 2, D-21079 Hamburg, Germany |
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Abstract: | A novel process for the industrial production of hydroxylated fatty acids involves epoxidation of plant oils and their derivatives,
followed by catalytic epoxy ring opening in the presence of water or other hydrogen donors, such as alcohols, diols, and amines.
Depending on the starting material, epoxidation followed by opening of the oxirane ring leads to fatty acids that contain
vicinal diol groups or to other substituted hydroxylated fatty acid derivatives. As an example for the preparation of a substituted
hydroxylated fatty acid derivative, the reaction of epoxidized rapeseed oil with monobutylamine as hydrogen donor is described.
Apart from the intended formation of hydroxyl groups with vicinal aminoalkyl groups, partial aminolysis of the ester compound
was also observed. Another example describes the reaction of epoxidized rapeseed oil with different molar proportions of 1,4-butanediol
as hydrogen donor. Depending on the molar proportion of the hydrogen donor, interesterification, or intermolecular ether formation
were observed as side reactions. The properties of various technical hydroxylated fatty acids and their derivatives, prepared
according to this novel process, are given, and potential applications of these products are suggested. |
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Keywords: | 9 10-Dihydroxy stearic acid dihydroxy tetrahydrofuran octadecanoic acid estolides hydroxylated fatty acid derivatives hydroxylated fatty acids hydroxylated triglycerides polyhydroxy fatty acids |
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