Selective synthesis of amphiphilic hydroxyalkylethers of disaccharides over solid basic catalysts: Influence of the superficial hydrophilic–lipophilic balance of the catalyst

The direct etherification of three disaccharidic polyols, sucrose, trehalose and isomalt®, with 1,2-epoxydodecane was studied. The catalytic activity of various solid basic catalysts, differing by their superficial hydrophilic–lipophilic properties, was investigated. Disaccharide hydroxyalkylethers yields greater than 90% were obtained in a DMSO–water mixture in the presence of the recoverable PS–NOH solid catalyst. The regioselectivity of the reaction was fully investigated by HPLC and NMR.

In this work, we report the etherification of three disaccharidic polyols, namely sucrose, trehalose and isomalt, with fatty 1,2-epoxydodecane over different solid basic catalysts. We show that the activity of the solid catalysts is closely linked to their superficial hydrophilic–lipophilic properties. The selectivity into monoether derivatives, the reaction regioselectivity as well as the surfactant properties of the newly prepared amphiphilic molecules are discussed. Figure optionsDownload as PowerPoint slide