Modifying the double bond in fatty acids for new materials: oleo-chemistry versus linoleo-chemistry

Authors: Bantchev, Grigor; Biresaw, Girma

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: 12/21/2018
Publication Date: 5/7/2019
Citation: Bantchev, G.B., Biresaw, G. 2019. Modifying the double bond in fatty acids for new materials: oleo-chemistry versus linoleo-chemistry. American Oil Chemists' Society Annual Meeting & Expo. Program Book p. 63.

Interpretive Summary:

Technical Abstract: This presentation will be about some reactions explored in search of novel lipid-based materials, with an emphasis on the differences between the chemistries of oleic and linoleic fatty acids. Thiol-ene, H-phosphonate-ene, and the epoxide-ring opening reactions will be discussed and the differences in the products contrasted. The oleate chain has one double bond and, when it reacts, only two very similar isomers (four isomers, if we account for chirality) are produced. The linoleate chain has two double bonds which, upon reaction, yields a larger number of isomers with functional groups in close proximity. In some cases, these functional groups react with each other, leading to a variety of linoleate-based structures that are not predictable from studying the reaction of oleates. Examples of such linoleate-based structures include: tetrahydrofuran, furan, tetrahydrothiophene, 1,2-dithiane and others.