Syntheses of surfactants from oleochemical epoxides

Sugar-based surfactants were obtained in good yields (up to 100%) under mild conditions (70°C, methanol or mixtures of methanol and water) by ring-opening of terminal epoxides with aminopolyols, derived from glucose. Reaction of N-methyl glucamine with epoxides from even-numbered C4-C18 alpha-olefins or from terminal unsaturated fatty acid methyl esters leads to linear products, while corresponding reactions with N-dodecyl glucamine or glucamine yield surfactants with different Y-structures. Products obtained by conversion of omega-epoxy fatty acid methyl esters were saponificated with NaOH or hydrolyzed enzymatically to sodium salts or free acids respectively, which are amphoteric surfactants. Studies of the surfactants at different pH-values demonstrate different surface active properties in aqueous solutions. Critical micelle concentrations (c.m.c.) in a range between 2 and 500mg/l and surface tensions of 25-40mN/m were measured for several of the synthesized sugar-based surfactants. The ring-opening products are rather poor foamers, whereas some of the corresponding hydrobromides show good foaming properties.