5-Hydroxy fatty acid amides from δ-lactones and alkyl glucamines

Abstract  δ-Lactones derived from unsaturated fatty acids are useful precursors to fatty amides due to their enhanced reactivity. Consequently, temperature-sensitive glucamines were easily converted to their 5-hydroxy fatty acid amides in high yield (52–97%) by reaction with C18 and C20 δ-lactones. High yields of amides (52–97%) were obtained with little or no solvent at 90°C in less than 24 h. C18 δ-lactones were more miscible in the glucamine than the C20 δ-lactones and thus increased reaction rates and yields of amides. In addition, amidation reactions run in the absence of catalyst gave good yields, whereas reactions in the presence of base catalysts completely inhibited the reaction. The 1-(N-alkyl-5-hydroxy fatty acid amido)-d-glucitols are expected to have useful properties as biodegradable components in detergents.