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 surfa ctants is described. Direct sulfonation of 6-O-acylsucrose using the p yridine-sulfur trioxide complex led to a mixture of the regioisomeric monosulfates, 6-O-acyl-4'-O-sulfosucrose and 6-O-acyl-1'-O-sulfosucros e, while sulfonation of 1'-O-acylsucrose afforded a mixture of 1'-O-ac yl-6'-O-sulfosucrose and 1'-O-acyl-6-O-sulfosucrose. The ratio of regi oisomers ranged from 4.7:1.0 to 7.5:1.0, depending on reaction time an d the size of the fatty acyl chain. The regiospecific synthesis of 6-O -acyl-4-O-sulfosucrose derivatives was accomplished by nucleophilic su bstitution of the sucrose 4,6-cyclic sulfate using various fatty acids . The amphoteric 6-alkylamino-6-deoxy-4-O-sulfosucrose surfactants wer e also synthesized by nucleophilic substitution of the sucrose cyclic sulfate by different fatty amines. All the newly synthesized sucrose-b ased surfactants displayed excellent surface-active properties. (C) 19 98 Elsevier Science Ltd. All rights reserved.