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N-METHYL-D-GLUCOSE AMINE SYNTHESIS OVER NI BASED CATALYSTS

Степан Петрович Михайлов, Mikhail G. Sulman, Valentina G. Matveeva, А. И. Сидоров, Valentin Yu. Doluda

Abstract

N-methyl-D-glucose amine is an amine formed by reduction of glucosylamine or glucose oxime. N-alkylated glucamines are prepared from D-glucose and relevant alkylamines. Here synthesis of N-methyl-D-glucose amine by consecutive condensation of D-glucose with methylamine in ethanol media followed by reduction over Ni containing hyper crosslinked polystyrene is reported. In typical synthesis 50 g sample of D-glucose monohydrate was added to 150 ml of ethanol (96 wt.%) and stirred under 600 rpm for 30 minutes. Suspension was heated up to 95 0C and methyl amine was bubbled through reaction mixture for half an hour to perform synthesis of N-methyl-D-glucose imine. After reaction end suspension was bubbled with nitrogen to evacuate excess of methylamine. Then 50 ml of ethanol was evaporated from reaction mixture. Reactor was cooled and 10 g of Ni (25 wt%) in hypercrosslinked polystyrene was added to reaction mixture. Reactor was flashed with hydrogen, heated to 140 0C, overall pressure was maintained us at 40 Bar. Hydrogenation was provided for 3 hours, than reactor was flashed with nitrogen. Additional 50 ml of ethanol was evaporated from reaction media. Than reactor was cooled to ambient temperature and N-methyl-D-glucose was crystallized at 40C. N-methyl-D-glucose amine yield was up to 90%. Influence of reaction temperature, reagents concentration, water concentration, hydrogen pressure, catalyst concentration were evaluated in study.

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DOI resolver: doi.org/10.5593/sgem2020/4.1/s17.016

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