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Efficient Preparation of Octyl α‐D‐Glucopyranoside Monohydrate: A Recirculation Procedure Involving Water Removal by Product Crystallisation
Author(s) -
Straathof A. J. J.,
van Bekkum H.,
Kieboom A. P. G.
Publication year - 1988
Publication title -
starch ‐ stärke
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.62
H-Index - 82
eISSN - 1521-379X
pISSN - 0038-9056
DOI - 10.1002/star.19880400608
Subject(s) - chemistry , yield (engineering) , ion exchange resin , petroleum ether , mother liquor , ion exchange , organic chemistry , solvent , sulfonic acid , crystallization , chromatography , nuclear chemistry , ion , materials science , extraction (chemistry) , metallurgy
D‐Glucose, suspended in 1‐octanol, was converted according to the Fischer ‐glycosidation using various macroporous sulfonic acid ionexchange resins as the catalyst. This resulted in an equilibrium mixture consisting of octyl D‐glucosides together with substantial amounts of reversion products. Octyl α‐D‐glucopyranoside monohydrate selectively crystallised from the equilibrium mixture upon the addition of petroleum ether (b. p. 40–65°C). The mother liquor was recirculated to the reactor and re‐equilibrated in the presence of additional D‐glucose and 1‐octanol. The ion‐exchange resin and petroleum ether were also recycled. This procedure allowed the one‐step preparation of crystalline octyl α‐D‐glucopyranoside monohydrate in a quantitative yield from D‐glucose and 1‐octanol without the use of toxic solvents or the formation of waste products.