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Title: Omega-functionalized fatty acids, alcohols, and ethers via olefin metathesis

item Zerkowski, Jonathan
item Solaiman, Daniel

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 1/5/2012
Publication Date: 7/1/2012
Citation: Zerkowski, J.A., Solaiman, D. 2012. Omega-functionalized fatty acids, alcohols, and ethers via olefin metathesis. Journal of the American Oil Chemists' Society. 89(7):1325-1332.

Interpretive Summary: This paper reports the preparation of new derivatives of agriculture-derived fats and oils. These new molecules possess altered shape and reactivity compared to naturally-occurring fats and oils, and they therefore represent new tools, or building blocks, for the preparation of polymers, coatings, lubricants, and nanomaterials. The starting point for making them is a fatty acid derived from a bio-detergent known as a sophorolipid, which is itself made by yeasts working upon agricultural byproducts such as soy molasses. Using known chemical reactions, we have modified this fatty acid to contain a site where other chemical groups can be attached to it in a new geometry. Alternatively, the shape of the fatty acid can just be made longer. The result is that these newly prepared compounds could be used to impart special new properties to materials, such as by making stronger/tougher plastics or UV-resistant ones or thin films that stick to metal surfaces.

Technical Abstract: Methyl 17-hydroxy stearate was converted to methyl octadec-16-enoate using copper sulfate adsorbed on silica gel. This compound, possessing unsaturation at the opposite end of the chain from the carboxylate, served as a useful substrate for the olefin metathesis reaction. As a result, several fatty acids with novel functional groups at the far end were prepared: A glyceryl ether attached at the 18-carbon, an aromatic fatty acid from eugenol, and a ferrocenyl fatty acid. By employing the omega-1 fatty alcohol, other groups were introduced: the terminal fluoride, bromide, and iodide were prepared, as was a thiol derivative. The penultimate and omega olefins reported here should serve as building blocks that allow fatty acids to make a greater contribute to a range of emerging technological areas.