Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Proceedings
Publication Acceptance Date: May 12, 1999
Publication Date: N/A
Technical Abstract: Meadowfoam a developing oilseed crop currently grown in the Pacific Northwestern United States is used to synthesize C-20 delta-lactones. Delta-lactones derived from Meadowfoam (limnanthes) unsaturated fatty acids, when treated with a series of glucamines in the presence of little or no solvent in the range of 50-90 C, underwent amidation reactions. The synthesis of a class of non-ionic surfactants, glucamides, will be discussed. The C-20 delta-lactones were easily converted to their corresponding 5-hydroxy fatty acid amides in modest yields (52-97%). A series of amidation reactions were studied, under a number of solvent and temperature conditions, and led to the conclusion that small amounts of the reaction products helped to increase the miscibility of the reactants. In cases of mixtures of delta- and gamma-lactones, the rate of ring opening for the delta-lactone was much faster then the gamma-lactone. The 5-hydroxy glucamides could then be separated from unreacted lactones and the 4-hydroxy glucamides. Previously synthesized glucamides have synergistic effects with common anionic surfactants, are readily biodegradable, and have a low irritation potential.