Alkyl polyglucosides were synthesized by solvent-free glycosidation using ultrasonic emulsification. We examined glycosidation conditions of fatty alcohol with glucose hydrate and anhydrous glucose in the presence of p-toluenesulfonic acid. Glucose was emulsified in a molar excess of fatty alcohol for 20 minutes with a ultra-sonicator at room temperature and converted in a stirred reactor to more than 95% polyglucoside within 2.5~3.5 hr under 20~30 mmHg at 110℃ with a three-fold molar ratio of fatty alcohol to glucose in the presence of 1mol% p-toluenesulfonic acid. It was possible to obtain a polyglucoside mixture of HLB 13 consisting of 65% monoglucoside and 35% oligoglucoside with less than 1% of fatty alcohol.

Glycoside fatty acid esters were synthesized by lipase-catalyzed glycosylation of fatty acids with methyl glycoside in solvent and solvent free process. Optimum condition of solvent process using 2-methyl-2-propanol were : moral ratio of methyl glycoside to fatty acid 1:3: initial concentration of methyl glycoside 50g/l:enzyme(immodilized lipase Novozym 435 from Candidia antarctica) content 1%(w/v) : desiccant content 9%(w/v); reaction temperature 60℃: reaction time 10hrs. The yield of 99% was obtained. Solvent-free process was carried out in total absence of solvent at 70℃ under reduced pressure, 5-20mmHg. To give meximum yield of 99% at the optimum condition of molar ratio of methyl glycoside to fatty acid 1:3, enzyme content 10%(w/w), and reaction time 10hrs. The glycosylation reactivity of different glycosylation agents were sequent to Methyl-β-D-fructofuranoside. Methyl-β-D-glucopyranoside. Methyl-β-D-fructofuranosi de, and Methyl-α-D-glucopyranoside.