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Effect of Different Ionic Liquids on 5‐Hydroxymethylfurfural Preparation from Glucose in DMA over AlCl 3 : Experimental and Theoretical Study
Author(s) -
Yang Yan,
Liu Wentao,
Wang Ningning,
Wang Haijun,
Li Wei,
Song Zhanxin
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500030
Subject(s) - chemistry , ionic liquid , yield (engineering) , fructose , bromide , organic chemistry , medicinal chemistry , nuclear chemistry , catalysis , materials science , metallurgy
In this work, effect of different ionic liquids (ILs) on 5‐hydroxymethylfurfural (HMF) preparation from glucose in N , N ‐dimethylacetamide (DMA) over AlCl 3 was revealed by a combined experimental and computational study. ILs used as cocatalysts in this work included N ‐methyl‐2‐pyrrolidone hydrogen sulfate ([NMP]HSO 4 ), N ‐methyl‐2‐pyrrolidone methyl sulfate ([NMP]CH 3 SO 3 ), N ‐methyl‐2‐pyrrolidone chlorine ([NMP]Cl) and N ‐methyl‐2‐pyrrolidone bromide ([NMP]Br) which were endowed with the same cation but different anions. According to the conclusion that fructose was intermediate product from glucose to HMF, we found fructose was transformed to more by‐products by [NMP]HSO 4 , making HMF yield decline significantly when glucose was treated as substrate. Neither glucose nor fructose could be converted by [NMP]CH 3 SO 3 efficiently, leading to its no influence on glucose conversion to HMF. [NMP]Br had a higher selectivity for HMF from fructose than [NMP]Cl and AlCl 3 . Besides, Al 3+ preferred to combine with Br − , slightly decreasing both the overall free energy barrier for glucose isomerization and activation barrier for H‐shift at 393.15 K. So a high HMF yield of 57% was obtained from glucose catalyzed by AlCl 3 together with [NMP]Br under mild conditions.