New Family of Surfactants from Biobased Materials

Abstract

β-C-Glycoside ketone derivatives of glucose, lactose, and maltose were converted to amines via a reductive amination using 5 wt % Rh/Al2O3 in ammoniacal methanol under 34 bar H2. The amines were isolated and then were used as the amine in the reductive amination of 2-undecanone that can be prepared from the seed oil of Cuphea. The resulting β-C-glycoside-2-aminoundecanes were characterized by MALDI-TOF mass spectrometry and 2D NMR. The critical micelle concentrations of the products as measured by isothermal calorimetry titration ranged from 1 to 5 mM, and the micelles carry a positive charge as measured by zeta potentials. The β-C-glycoside 2-aminoundecanes have antimicrobial activity against Bacillus subtilis, Pseudomonas aeruginosa, Erwinia amylovora, and Escherichia coli, with the C-glucoside derivative having the greatest activity with a minimum inhibitory concentration of 0.31 mM and a minimum bactericide concentration of 0.62 mM against the Gram positive organisms. Against the Gram negative Erwinia and Escherichia, the MIC is 0.62 mM. This work introduces a new family of sustainable surfactants with potential uses in personal care and cleaning products.