Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: April 8, 2006
Publication Date: July 1, 2006
Citation: Zerkowski, J.A., Solaiman, D. 2006. Synthesis of polyfunctional fatty amines from sophorolipid-derived 17-hydroxyoleic acid. Journal of the American Oil Chemists' Society. 83:621-628. Interpretive Summary: Agricultural coproducts such as soy molasses and tallow are created in large amounts every year. We have used fermentation by yeasts to convert these biorenewable agricultural coproducts into sophorolipids (a type of biological surfactant). Sophorolipids contain novel fatty acids that are easily disconnected and separated from the parent molecules. In their own right, these fatty acids hold promise as abundant and versatile starting materials that can be employed in commercially significant settings. They do not, however, react easily with certain kinds of commonly used polymerization agents. We have used well-established methods of organic chemistry to widen the scope of the fatty acids' utility. Specifically, we have added one, two, or three reactive units called amino groups into the fatty acid in a variety of locations and orientations. These reactive groups will allow the modified fatty acid to find application in a number of technological situations, from building blocks for polymers or detergents to coatings or lubricants.
Technical Abstract: A series of mono- and diamines and one triamine have been prepared using methyl 17-hydroxyoleate as the common starting material. The 17-hydroxyoleate is an abundant bio-derived material obtained from acid alcoholysis of sophorolipids, which in turn are produced by fermentation of agricultural byproducts. Incorporation of the amino unit(s) can be selectively performed at either end of the chain or at its middle. The chief synthetic reactions employed are allylic bromination, Curtius rearrangement, and the Mitsunobu reaction. These fatty amines also possess functionality such as hydroxy groups, carboxylic acids, and C-C double bonds. The amines are isolated in protected form using a variety of protecting groups, the identities of which can be selected on the basis of the intended use of the amine. These novel compounds will be of interest in the preparation of highly functionalized polymers and surfactants, among other areas.