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One‐Pot Transformation of Carbohydrates into Valuable Furan Derivatives via 5‐Hydroxymethylfurfural
Author(s) -
Wrigstedt Pauli,
Keskiväli Juha,
PereaBuceta Jesús E.,
Repo Timo
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201701106
Subject(s) - chemistry , furan , cellobiose , organic chemistry , hydroxymethylfurfural , inulin , aldol condensation , lignocellulosic biomass , substrate (aquarium) , cellulose , fructose , methyl isobutyl ketone , catalysis , ketone , furfural , cellulase , biochemistry , oceanography , geology
5‐Hydroxymethylfurfural (HMF) is a pivotal chemical in the utilization of biomass as a chemical feedstock. For this approach the vast majority of methods require access to pure HMF from biomass before its utilization, which incorporates one or more purification steps that obstruct industrial implementation. We describe an operationally simple and versatile method that encompasses both the dehydration of several carbohydrate substrates into HMF and subsequently its direct conversion into various high value‐added furan derivatives in a one‐pot process. To that end, we selected the aldol condensation of HMF with methyl isobutyl ketone (MIBK) as a model reaction. With the optimized conditions of solvent and base catalyst in hand, the one‐pot dehydration of fructose and the condensation sequence with various ketones afforded the products in good overall yields over two steps. The scope of the process was expanded to more complex carbohydrates, such as glucose, lactose, sucrose, cellobiose, and inulin. Moreover, by fine‐tuning the reaction conditions, the one‐pot methodology in which we used inulin as the substrate was highly efficient if applied to various other important reactions, such as oxidation, reduction, and Cannizzaro and Baylis–Hillman reactions, which rendered the corresponding furan derivatives in high overall yields.