Sucrose ether‐ and ester‐linked surfactants

Several effective nonionic surface‐active agents in which a single sucrose moiety is the only solubilizing group were described. Alkylsucroses, prepared via sodium sucrate in dimethyl sulfoxide (DMSO) and higher alkyl bromides, are believed to be the first sugar‐based surfactants which are at least equivalent to the best anionics and nonionics in cloth detergency on the basis of laboratory data; they were also active lime‐soap disperstants. Another ether‐linked type, the (3‐alkoxy‐2‐hydroxypropyl) and (2‐hydroxyalkyl) sucroses, derived from glycidyl ethers or olefin oxides, although second in detergency to the first type, included exceptional nonionic lathering agents, t‐Dodecyl‐benzylsucrose, from dodecylbenzyl chloride, was also a rather active detergent and lime‐soap dispersant. Less active but easily prepared sucrose half‐esters from alkenylsuccinic anhydrides were described. One sucrose moiety in ether‐linked surfactants was an effective hydrophile for alkyl hydrophobes at least as large as hexadecyl, but tridecyl derivatives were superior in activity. Major importance was attached to the choice of solvent, catalyst, and time/temperature factors. Evidence was presented to show that sucrose derivatives were partially degraded by the alkaline conditions required in this work and that this degradation was both detrimental to detergeney and initially beneficial to lather in specific cases. An improved procedure involving the use of DMSO for the alkaline dehydrochlorination of higher alkoxychloropropanols to glycidyl ethers was described.