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Title: Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural

Abstract

Sugars were converted to hydroxymethylfurfural (HMF) at high yield in ionic liquids without the addition of Bronsted acids. Very small amount of certain metal halides significantly reduced the fructose dehydration barrier in ionic liquids producing HMF at high yields. Most remarkably, glucose, a common sugar molecule, was selectively converted to HMF in good yield in ionic liquids containing a small amount of CrCl2. Thus CrCl2 is unique among metal chlorides tested for its effectiveness in both isomerizing glucose as well as dehydrating fructose. Only negligble amount of levulinic acid was formed in the reactions. The catalytic activity of metal chlorides for sugar conversion in ionic liquids is perhaps related to hydroxyl group of the sugar forming metal complexes with the unsaturated metal center.

Authors:
; ; ;
Publication Date:
Research Org.:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
910269
Report Number(s):
PNNL-SA-52130
Journal ID: ISSN 0193-4511; SCEHDK; TRN: US200723%%393
DOE Contract Number:  
AC05-76RL01830
Resource Type:
Journal Article
Journal Name:
Science, 316(5831):1597-1600
Additional Journal Information:
Journal Volume: 316; Journal Issue: 5831; Journal ID: ISSN 0193-4511
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; CATALYTIC EFFECTS; CHROMIUM CHLORIDES; ALDEHYDES; FURANS; SYNTHESIS; GLUCOSE; SACCHARIDES; SACCHAROSE

Citation Formats

Zhao, Haibo, Holladay, John E, Brown, Heather M, and Zhang, Z Conrad. Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural. United States: N. p., 2007. Web. doi:10.1126/science.1141199.
Zhao, Haibo, Holladay, John E, Brown, Heather M, & Zhang, Z Conrad. Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural. United States. https://doi.org/10.1126/science.1141199
Zhao, Haibo, Holladay, John E, Brown, Heather M, and Zhang, Z Conrad. Fri . "Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural". United States. https://doi.org/10.1126/science.1141199.
@article{osti_910269,
title = {Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural},
author = {Zhao, Haibo and Holladay, John E and Brown, Heather M and Zhang, Z Conrad},
abstractNote = {Sugars were converted to hydroxymethylfurfural (HMF) at high yield in ionic liquids without the addition of Bronsted acids. Very small amount of certain metal halides significantly reduced the fructose dehydration barrier in ionic liquids producing HMF at high yields. Most remarkably, glucose, a common sugar molecule, was selectively converted to HMF in good yield in ionic liquids containing a small amount of CrCl2. Thus CrCl2 is unique among metal chlorides tested for its effectiveness in both isomerizing glucose as well as dehydrating fructose. Only negligble amount of levulinic acid was formed in the reactions. The catalytic activity of metal chlorides for sugar conversion in ionic liquids is perhaps related to hydroxyl group of the sugar forming metal complexes with the unsaturated metal center.},
doi = {10.1126/science.1141199},
url = {https://www.osti.gov/biblio/910269}, journal = {Science, 316(5831):1597-1600},
issn = {0193-4511},
number = 5831,
volume = 316,
place = {United States},
year = {2007},
month = {6}
}