Synthesis of Sucrose-Based Surfactants Through Regioselective Sulfonation of Acylsucrose and the Nucleophilic Opening of a Sucrose Cyclic Sulfate

Abstract

Synthesis of a new class of anionic and amphoteric sucrose-based surfactants is described. Direct sulfonation of 6-O-acylsucrose using the pyridine–sulfur trioxide complex led to a mixture of the regioisomeric monosulfates, 6-O-acyl-4′–O-sulfosucrose and 6-O-acyl-1′-O-sulfosucrose, while sulfonation of 1′-O-acylsucrose afforded a mixture of 1′-O-acyl-6′-O-sulfosucrose and 1′-O-acyl-6-O-sulfosucrose. The ratio of regioisomers ranged from 4.7:1.0 to 7.5:1.0, depending on reaction time and the size of the fatty acyl chain. The regiospecific synthesis of 6-O-acyl-4-O-sulfosucrose derivatives was accomplished by nucleophilic substitution of the sucrose 4,6-cyclic sulfate using various fatty acids. The amphoteric 6-alkylamino-6-deoxy-4-O-sulfosucrose surfactants were also synthesized by nucleophilic substitution of the sucrose cyclic sulfate by different fatty amines. All the newly synthesized sucrose-based surfactants displayed excellent surface-active properties.