Journal
RSC ADVANCES
Volume 5, Issue 35, Pages 27805-27813Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ra02057c
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Funding
- National Natural Science Foundation of China [21206057]
- Natural Science Foundation of Jiangsu Province, China [BK2012118, BK2012547]
- MOE SAFEA [B13025]
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In the present work, the influence of organic solvent on the mechanism of 5-hydroxymethylfurfural (HMF) preparation from glucose over CrCl3 and the role of Bronsted acid (N-methyl-2-pyrrolidone hydrogen sulfate ([NMP]HSO4), N-methyl-2-pyrrolidone bromide ([NMP]Br), N-methyl-2-pyrrolidone chlorine ([NMP]Cl), H2SO4, HBr and HCl) during the reaction were researched by a complementary computational and experimental study. It was found that dimethyl sulfoxide (DMSO) gave the lowest conversion of glucose by surrounding CrCl3, forming a six-coordinated structure (CrCl3-3DMSO). Glucose conversion in N, N-dimethylformamide (DMF) was not selective. N, N-Dimethylacetamide (DMA) and n-butyl alcohol exhibited superior selectivity towards HMF from glucose. Then the role of different Bronsted acids in DMA was expounded. On increasing the dosage of [NMP]HSO4, glucose conversion decreased. A computational study found that HSO4- could also combine with CrCl3, forming six-coordinate complexes. Addition of [NMP]Br and [NMP]Cl accelerated the generation of HMF significantly but didn't increase the yield. An experimental method preliminarily confirmed that they were mainly responsible for fructose dehydration to HMF. A subsequent computational study further verified that the two kinds of ILs had no effect on glucose isomerization.
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