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Selective Conversion of 5‐Hydroxymethylfuraldehyde Using Cp*Ir Catalysts in Aqueous Formate Buffer Solution
Author(s) -
Wu WeiPeng,
Xu YongJian,
Zhu Rui,
Cui MinShu,
Li XingLong,
Deng Jin,
Fu Yao
Publication year - 2016
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201501625
Subject(s) - aqueous solution , catalysis , formate , buffer (optical fiber) , chemistry , inorganic chemistry , heterogeneous catalysis , chemical engineering , organic chemistry , telecommunications , computer science , engineering
Abstract The highly selective hydrogenation/hydrolytic ring‐opening reaction of 5‐hydroxymethylfuraldehyde (5‐HMF) was catalyzed by homogeneous Cp*Ir III half‐sandwich complexes to produce 1‐hydroxy‐2,5‐hexanedione (HHD). Adjustment of pH was found to regulate the distribution of products and reaction selectivity, and full conversion of 5‐HMF to HHD with 99 % selectivity was achieved at pH 2.5. A mechanistic study revealed that the hydrolysis/ring‐opening reaction of 2,5‐bis‐(hydroxymethyl)furan is the important intermediate reaction step. In addition, an isolated yield of 85 % for HHD was obtained in a 10 g‐scale experiment, and the reaction with fructose as the starting material also led to a 98 % GC yield (71.9 % to fructose) of HHD owing to the excellent tolerance of the catalyst under acidic conditions.