Sulfoxides and sulfones as solvents for the manufacture of alkyl polyglycosides without added catalyst

Abstract

Sulfoxides and sulfones as solvents have been used for the glycosidation of various carbohydrates with decanol in the absence of an added catalyst. The production of decyl-D-xylosides has been studied in dimethylsulfoxide and the importance of parameters such as pressure and temperature on the reaction time has been pointed out. Organic acids produced by carbohydrate caramelization highly influenced the glycosidation kinetics. Other sulfur containing solvents were also effective. A decanol–sulfolane biphasic reaction medium has been designed for the production of decyl-D-xylosides in short reaction times and yields up to 83%. Sulfolane has been easily recovered by liquid–liquid separation and reused in the next three glycosidation reactions without any yield decrease.