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One‐Pot Deoxygenation of Fructose to Furfuryl Alcohol by Sequential Dehydration and Decarbonylation
Author(s) -
Dai Jinhang,
Fu Xing,
Zhu Liangfang,
Tang Jinqiang,
Guo Xiawei,
Hu Changwei
Publication year - 2016
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.201501292
Subject(s) - decarbonylation , chemistry , furfuryl alcohol , deoxygenation , dehydration , fructose , organic chemistry , dehydration reaction , catalysis , formic acid , medicinal chemistry , biochemistry
Fructose was deoxygenated to furfuryl alcohol (FFA) by tandem dehydration and decarbonylation in one pot over the AlCl 3 ⋅ 6 H 2 O/Pd(OAc) 2 catalyst combination to give a high FFA yield of 40.6 %. AlCl 3 ⋅ 6 H 2 O behaves as an effective Lewis acid to catalyze the dehydration of fructose to 5‐hydroxymethylfurfural (HMF), and subsequently, Pd(OAc) 2 catalyzes the removal of a CO moiety from HMF to produce FFA selectively. The hydroxyl group on the HMF intermediate was stabilized by poly(1‐vinyl‐2‐pyrrolidinone) through an intermolecular hydrogen bond, which accelerated the dehydration of fructose and inhibited the hydrogenation of HMF by formic acid. The decarbonylation of HMF was promoted and the unwanted decomposition of fructose was inhibited through the use of 4 Å molecular sieves. This research highlights a “one‐pot” catalytic system to transform renewable carbohydrates into fine chemicals by tandem dehydration and decarbonylation reactions without the separation or purification of HMF.