Synthesis of sucrose-based surfactants through regioselective sulfonation of acylsucrose and the nucleophilic opening of a sucrose cyclic sulfate

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-40±O-sulfosucrose and 6-O-acyl-10-O-sulfosucrose, while sulfonation of 10-O-acylsucrose a€orded a mixture of 10-O-acyl-60-O-sulfosucrose and 10-O-acyl-6O-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 regiospeci®c 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 di€erent fatty amines. All the newly synthesized sucrose-based surfactants displayed excellent surface-active properties. # 1998 Elsevier Science Ltd. All rights reserved