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:
-
- 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)
- The Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio); Discovery Park; Purdue University; West Lafayette; USA
- 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}
}
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Works referenced in this record:
Selective Base-Catalyzed Isomerization of Glucose to Fructose
journal, November 2014
- Liu, Chi; Carraher, Jack M.; Swedberg, Jordan L.
- ACS Catalysis, Vol. 4, Issue 12
Kinetic and Mechanistic Study of Glucose Isomerization Using Homogeneous Organic Brønsted Base Catalysts in Water
journal, April 2015
- Carraher, Jack M.; Fleitman, Chelsea N.; Tessonnier, Jean-Philippe
- ACS Catalysis, Vol. 5, Issue 6
Production of 5-Hydroxymethylfurfural from Glucose Using a Combination of Lewis and Brønsted Acid Catalysts in Water in a Biphasic Reactor with an Alkylphenol Solvent
journal, April 2012
- Pagán-Torres, Yomaira J.; Wang, Tianfu; Gallo, Jean Marcel R.
- ACS Catalysis, Vol. 2, Issue 6, p. 930-934
Microwave assisted conversion of carbohydrates and biopolymers to 5-hydroxymethylfurfural with aluminium chloride catalyst in water
journal, January 2011
- De, Sudipta; Dutta, Saikat; Saha, Basudeb
- Green Chemistry, Vol. 13, Issue 10
Characterization of acid catalytic domains for cellulose hydrolysis and glucose degradation
journal, July 2002
- Mosier, Nathan S.; Ladisch, Christine M.; Ladisch, Michael R.
- Biotechnology and Bioengineering, Vol. 79, Issue 6
Reaction media dominated product selectivity in the isomerization of glucose by chromium trichloride: From aqueous to non-aqueous systems
journal, October 2014
- Jia, Songyan; Liu, Kairui; Xu, Zhanwei
- Catalysis Today, Vol. 234
Characterization of Dicarboxylic Acids for Cellulose Hydrolysis
journal, June 2001
- Mosier, N. S.; Sarikaya, A.; Ladisch, C. M.
- Biotechnology Progress, Vol. 17, Issue 3
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
- Choudhary, Vinit; Mushrif, Samir H.; Ho, Christopher
- Journal of the American Chemical Society, Vol. 135, Issue 10
A theoretical study of glucose mutarotation in aqueous solution
journal, June 2006
- Silva, Alexander M.; da Silva, Edilson C.; da Silva, Clarissa O.
- Carbohydrate Research, Vol. 341, Issue 8
Stereochemical evidence for a cis-enediol intermediate in Mn-dependent aldose isomerases
journal, April 1969
- Rose, Irwin A.; O'Connell, Edward L.; Mortlock, Robert P.
- Biochimica et Biophysica Acta (BBA) - Enzymology, Vol. 178, Issue 2
Metal Ion Roles and the Movement of Hydrogen during Reaction Catalyzed by D-Xylose Isomerase: A Joint X-Ray and Neutron Diffraction Study
journal, June 2010
- Kovalevsky, Andrey Y.; Hanson, Leif; Fisher, S. Zoe
- Structure, Vol. 18, Issue 6, p. 688-699
Features of promising technologies for pretreatment of lignocellulosic biomass
journal, April 2005
- Mosier, Nathan; Wyman, Charles; Dale, Bruce
- Bioresource Technology, Vol. 96, Issue 6, p. 673-686
Isotopic Exchange plus Substrate and Inhibition Kinetics of D-Xylose Isomerase Do Not Support a Proton-Transfer Mechanism
journal, February 1994
- Allen, Karen N.; Lavie, Arnon; Farber, Gregory K.
- Biochemistry, Vol. 33, Issue 6
Structure–performance correlations of Mg–Al hydrotalcite catalysts for the isomerization of glucose into fructose
journal, July 2015
- Delidovich, Irina; Palkovits, Regina
- Journal of Catalysis, Vol. 327
Comparison of Homogeneous and Heterogeneous Catalysts for Glucose-to-Fructose Isomerization in Aqueous Media
journal, September 2013
- Choudhary, Vinit; Pinar, Ana B.; Lobo, Raul F.
- ChemSusChem, Vol. 6, Issue 12
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
- Mushrif, Samir H.; Varghese, Jithin J.; Vlachos, Dionisios G.
- Phys. Chem. Chem. Phys., Vol. 16, Issue 36
Mechanistic Study of Glucose-to-Fructose Isomerization in Water Catalyzed by [Al(OH) 2 (aq)] +
journal, August 2015
- Tang, Jinqiang; Guo, Xiawei; Zhu, Liangfang
- ACS Catalysis, Vol. 5, Issue 9
SnCl 4 -catalyzed isomerization/dehydration of xylose and glucose to furanics in water
journal, January 2015
- Enslow, Kristopher R.; Bell, Alexis T.
- Catalysis Science & Technology, Vol. 5, Issue 5
Catalytic activity and stability of hydrophobic Mg–Al hydrotalcites in the continuous aqueous-phase isomerization of glucose into fructose
journal, January 2014
- Delidovich, I.; Palkovits, R.
- Catal. Sci. Technol., Vol. 4, Issue 12
Acidities of Stable Simple Enols and Bond Dissociation Enthalpies of Their H−O Bonds in DMSO
journal, August 1997
- Bordwell, F. G.; Zhang, Shizhong; Eventova, Irina
- The Journal of Organic Chemistry, Vol. 62, Issue 16
Metalloenzyme-like catalyzed isomerizations of sugars by Lewis acid zeolites
journal, June 2012
- Bermejo-Deval, R.; Assary, R. S.; Nikolla, E.
- Proceedings of the National Academy of Sciences, Vol. 109, Issue 25
Biomimetic Catalysis for Hemicellulose Hydrolysis in Corn Stover
journal, February 2007
- Lu, Y.; Mosier, N. S.
- Biotechnology Progress, Vol. 23, Issue 1
Glucose–fructose isomerisation promoted by basic hybrid catalysts
journal, November 2012
- Souza, Rodrigo O. L.; Fabiano, Demian Patrick; Feche, Cyril
- Catalysis Today, Vol. 195, Issue 1
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
- Rasrendra, C. B.; Makertihartha, I. G. B. N.; Adisasmito, S.
- Topics in Catalysis, Vol. 53, Issue 15-18
Anomeric specificity and mechanism of two pentose isomerases
journal, March 1971
- Schray, Keith J.; Rose, Irwin A.
- Biochemistry, Vol. 10, Issue 6
Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water
journal, March 2010
- Moliner, M.; Roman-Leshkov, Y.; Davis, M. E.
- Proceedings of the National Academy of Sciences, Vol. 107, Issue 14, p. 6164-6168
The effect of hydrochloric acid on the conversion of glucose to 5-hydroxymethylfurfural in AlCl3–H2O/THF biphasic medium
journal, September 2013
- Yang, Yu; Hu, Changwei; Abu-Omar, Mahdi M.
- Journal of Molecular Catalysis A: Chemical, Vol. 376
Conversion of carbohydrates and lignocellulosic biomass into 5-hydroxymethylfurfural using AlCl3·6H2O catalyst in a biphasic solvent system
journal, January 2012
- Yang, Yu; Hu, Chang-wei; Abu-Omar, Mahdi M.
- Green Chem., Vol. 14, Issue 2, p. 509-513
Kinetics of Maleic Acid and Aluminum Chloride Catalyzed Dehydration and Degradation of Glucose
journal, March 2015
- Zhang, Ximing; Hewetson, Barron B.; Mosier, Nathan S.
- Energy & Fuels, Vol. 29, Issue 4
Catalytic Glucose Isomerization by Porous Coordination Polymers with Open Metal Sites
journal, July 2014
- Akiyama, George; Matsuda, Ryotaro; Sato, Hiroshi
- Chemistry - An Asian Journal, Vol. 9, Issue 10
Production of γ-valerolactone from biomass-derived compounds using formic acid as a hydrogen source over supported metal catalysts in water solvent
journal, January 2014
- Son, Pham Anh; Nishimura, Shun; Ebitani, Kohki
- RSC Advances, Vol. 4, Issue 21
Kinetic modeling analysis of maleic acid-catalyzed hemicellulose hydrolysis in corn stover
journal, December 2008
- Lu, Yulin; Mosier, Nathan S.
- Biotechnology and Bioengineering, Vol. 101, Issue 6
Free Energy Surface for Brønsted Acid-Catalyzed Glucose Ring-Opening in Aqueous Solution
journal, September 2013
- Qian, Xianghong
- The Journal of Physical Chemistry B, Vol. 117, Issue 39
Efficient Isomerization of Glucose to Fructose over Zeolites in Consecutive Reactions in Alcohol and Aqueous Media
journal, March 2013
- Saravanamurugan, Shunmugavel; Paniagua, Marta; Melero, Juan A.
- Journal of the American Chemical Society, Vol. 135, Issue 14
Mechanistic Imperatives for Aldose−Ketose Isomerization in Water: Specific, General Base- and Metal Ion-Catalyzed Isomerization of Glyceraldehyde with Proton and Hydride Transfer
journal, February 2001
- Nagorski, R. W.; Richard, John P.
- Journal of the American Chemical Society, Vol. 123, Issue 5
Mechanism of Glucose Isomerization Using a Solid Lewis Acid Catalyst in Water
journal, October 2010
- Román-Leshkov, Yuriy; Moliner, Manuel; Labinger, Jay A.
- Angewandte Chemie International Edition, Vol. 49, Issue 47, p. 8954-8957