Synthesis of Polyfunctional Fatty Amines from Sophorolipid-Derived 17-Hydroxy Oleic Acid

A series of mono- and diamines and one triamine have been prepared using methyl 17-hydroxy oleate as the common starting material. The 17-hydroxy oleate is an abundant bioderived material obtained from acid alcoholysis of sophorolipids, which in turn are produced by fermentation of agricultural by-products. Incorporation of the amino unit(s) can be selectively performed at either end of the chain or at its middle. The chief synthetic reactions used 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.