skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Maleic acid and aluminum chloride catalyzed conversion of glucose to 5-(hydroxymethyl) furfural and levulinic acid in aqueous media

Abstract

Maleic acid (MA) and AlCl3self-assemble into catalytic complexes (Al–(MA)2–(OH)2(aq)) with improved selectivity for converting glucose to HMF, and levulinic acid.

Authors:
 [1]; ORCiD logo [2];  [2];  [3];  [2];  [2];  [1]
  1. Laboratory of Renewable Resources Engineering and Department of Agricultural and Biological Engineering; Purdue University; West Lafayette; USA; The Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio)
  2. The Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio); Discovery Park; Purdue University; West Lafayette; USA
  3. Laboratory of Renewable Resources Engineering and Department of Agricultural and Biological Engineering; Purdue University; West Lafayette; USA; College of Engineering
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1388822
DOE Contract Number:  
SC000997
Resource Type:
Journal Article
Journal Name:
Green Chemistry
Additional Journal Information:
Journal Volume: 18; Journal Issue: 19; Related Information: C3Bio partners with Purdue University (lead); Argonne National Laboratory; National Renewable Energy Laboratory; Northeastern University; University of Tennessee; Journal ID: ISSN 1463-9262
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
catalysis (homogeneous), catalysis (heterogeneous), biofuels (including algae and biomass), bio-inspired, materials and chemistry by design, synthesis (self-assembly), synthesis (scalable processing)

Citation Formats

Zhang, Ximing, Murria, Priya, Jiang, Yuan, Xiao, Weihua, Kenttämaa, Hilkka I., Abu-Omar, Mahdi M., and Mosier, Nathan S. Maleic acid and aluminum chloride catalyzed conversion of glucose to 5-(hydroxymethyl) furfural and levulinic acid in aqueous media. United States: N. p., 2016. Web. doi:10.1039/C6GC01395C.
Zhang, Ximing, Murria, Priya, Jiang, Yuan, Xiao, Weihua, Kenttämaa, Hilkka I., Abu-Omar, Mahdi M., & Mosier, Nathan S. Maleic acid and aluminum chloride catalyzed conversion of glucose to 5-(hydroxymethyl) furfural and levulinic acid in aqueous media. United States. https://doi.org/10.1039/C6GC01395C
Zhang, Ximing, Murria, Priya, Jiang, Yuan, Xiao, Weihua, Kenttämaa, Hilkka I., Abu-Omar, Mahdi M., and Mosier, Nathan S. 2016. "Maleic acid and aluminum chloride catalyzed conversion of glucose to 5-(hydroxymethyl) furfural and levulinic acid in aqueous media". United States. https://doi.org/10.1039/C6GC01395C.
@article{osti_1388822,
title = {Maleic acid and aluminum chloride catalyzed conversion of glucose to 5-(hydroxymethyl) furfural and levulinic acid in aqueous media},
author = {Zhang, Ximing and Murria, Priya and Jiang, Yuan and Xiao, Weihua and Kenttämaa, Hilkka I. and Abu-Omar, Mahdi M. and Mosier, Nathan S.},
abstractNote = {Maleic acid (MA) and AlCl3self-assemble into catalytic complexes (Al–(MA)2–(OH)2(aq)) with improved selectivity for converting glucose to HMF, and levulinic acid.},
doi = {10.1039/C6GC01395C},
url = {https://www.osti.gov/biblio/1388822}, journal = {Green Chemistry},
issn = {1463-9262},
number = 19,
volume = 18,
place = {United States},
year = {Fri Jan 01 00:00:00 EST 2016},
month = {Fri Jan 01 00:00:00 EST 2016}
}

Works referenced in this record:

Selective Base-Catalyzed Isomerization of Glucose to Fructose
journal, November 2014


Kinetic and Mechanistic Study of Glucose Isomerization Using Homogeneous Organic Brønsted Base Catalysts in Water
journal, April 2015


Characterization of acid catalytic domains for cellulose hydrolysis and glucose degradation
journal, July 2002


Characterization of Dicarboxylic Acids for Cellulose Hydrolysis
journal, June 2001


Insights into the Interplay of Lewis and Brønsted Acid Catalysts in Glucose and Fructose Conversion to 5-(Hydroxymethyl)furfural and Levulinic Acid in Aqueous Media
journal, March 2013


A theoretical study of glucose mutarotation in aqueous solution
journal, June 2006


Stereochemical evidence for a cis-enediol intermediate in Mn-dependent aldose isomerases
journal, April 1969


Features of promising technologies for pretreatment of lignocellulosic biomass
journal, April 2005


Isotopic Exchange plus Substrate and Inhibition Kinetics of D-Xylose Isomerase Do Not Support a Proton-Transfer Mechanism
journal, February 1994


Comparison of Homogeneous and Heterogeneous Catalysts for Glucose-to-Fructose Isomerization in Aqueous Media
journal, September 2013


Insights into the Cr( iii ) catalyzed isomerization mechanism of glucose to fructose in the presence of water using ab initio molecular dynamics
journal, January 2014


Mechanistic Study of Glucose-to-Fructose Isomerization in Water Catalyzed by [Al(OH) 2 (aq)] +
journal, August 2015


SnCl 4 -catalyzed isomerization/dehydration of xylose and glucose to furanics in water
journal, January 2015


Acidities of Stable Simple Enols and Bond Dissociation Enthalpies of Their H−O Bonds in DMSO
journal, August 1997


Metalloenzyme-like catalyzed isomerizations of sugars by Lewis acid zeolites
journal, June 2012


Biomimetic Catalysis for Hemicellulose Hydrolysis in Corn Stover
journal, February 2007


Glucose–fructose isomerisation promoted by basic hybrid catalysts
journal, November 2012


Green Chemicals from d-glucose: Systematic Studies on Catalytic Effects of Inorganic Salts on the Chemo-Selectivity and Yield in Aqueous Solutions
journal, May 2010


Anomeric specificity and mechanism of two pentose isomerases
journal, March 1971


Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water
journal, March 2010


The effect of hydrochloric acid on the conversion of glucose to 5-hydroxymethylfurfural in AlCl3–H2O/THF biphasic medium
journal, September 2013


Kinetics of Maleic Acid and Aluminum Chloride Catalyzed Dehydration and Degradation of Glucose
journal, March 2015


Catalytic Glucose Isomerization by Porous Coordination Polymers with Open Metal Sites
journal, July 2014


Kinetic modeling analysis of maleic acid-catalyzed hemicellulose hydrolysis in corn stover
journal, December 2008


Free Energy Surface for Brønsted Acid-Catalyzed Glucose Ring-Opening in Aqueous Solution
journal, September 2013


Efficient Isomerization of Glucose to Fructose over Zeolites in Consecutive Reactions in Alcohol and Aqueous Media
journal, March 2013


Mechanism of Glucose Isomerization Using a Solid Lewis Acid Catalyst in Water
journal, October 2010