Glucose Conversion to Furans in Alcohols Catalyzed by Lewis Acidic Beta Zeolites and Brønsted Acidic Resins

Mahmoud, Eyas

doi:10.1002/slct.201701815

Title: Glucose Conversion to Furans in Alcohols Catalyzed by Lewis Acidic Beta Zeolites and Brønsted Acidic Resins

Journal Article · Mon Nov 13 00:00:00 EST 2017 · Chemistry Select

DOI:https://doi.org/10.1002/slct.201701815· OSTI ID:1470090

Mahmoud, Eyas ^[1]

Univ. of South Carolina, Columbia, SC (United States). Dept. of Chemical Engineering

Abstract Glucose was converted to 5‐(hydroxymethyl)furfural (HMF) and the potential biodiesel additives 5‐(ethoxymethyl)furfural (EMF) and 5‐(isopropoxymethyl)furfural (IMF) by Lewis acidic zeolites and Brønsted acidic resins. The conversion occured by sequential isomerization and dehydration reactions in semiaqueous mixtures containing ethanol or isopropanol. Sn‐beta and Amberlyst® 15 catalyzed the conversion of glucose to HMF and IMF in 53% yield in isopropanol containing 7.5 weight % water. The yield of undetected byproducts including humins was 7%. The moderate yield is attributed to the increased selectivity of the isomerization reaction and the suppression of further reactions of HMF to byproducts such as levullinic acid, formic acid, and humins in the alcohols.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001004

OSTI ID:: 1470090

Alternate ID(s):: OSTI ID: 1408534

Journal Information:: Chemistry Select, Vol. 2, Issue 32; Related Information: CCEI partners with the University of Delaware (lead); Brookhaven National Laboratory; California Institute of Technology; Columbia University; University of Delaware; Lehigh University; University of Massachusetts, Amherst; Massachusetts Institute of Technology; University of Minnesota; Pacific Northwest National Laboratory; University of Pennsylvania; Princeton University; Rutgers University; ISSN 2365-6549

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 5 works

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References (34)

Direct, High-Yield Conversions of Cellulose into Biofuel and Platform Chemicals-On the Way to a Sustainable Biobased Economy Rüsch gen. Klaas, Mark; Schöne, Heralt ChemSusChem, Vol. 2, Issue 2 https://doi.org/10.1002/cssc.200800186	journal	February 2009
Al-Free Sn-Beta Zeolite as a Catalyst for the Selective Reduction of Carbonyl Compounds (Meerwein−Ponndorf−Verley Reaction) Corma, Avelino; Domine, Marcelo E.; Nemeth, Laszlo Journal of the American Chemical Society, Vol. 124, Issue 13, p. 3194-3195 https://doi.org/10.1021/ja012297m	journal	April 2002
“One-Pot” Synthesis of 5-(Hydroxymethyl)furfural from Carbohydrates using Tin-Beta Zeolite Nikolla, Eranda; Román-Leshkov, Yuriy; Moliner, Manuel ACS Catalysis, Vol. 1, Issue 4, p. 408-410 https://doi.org/10.1021/cs2000544	journal	April 2011
Engineered Synthetic Pathway for Isopropanol Production in Escherichia coli Hanai, T.; Atsumi, S.; Liao, J. C. Applied and Environmental Microbiology, Vol. 73, Issue 24, p. 7814-7818 https://doi.org/10.1128/AEM.01140-07	journal	October 2007
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 Pagán-Torres, Yomaira J.; Wang, Tianfu; Gallo, Jean Marcel R. ACS Catalysis, Vol. 2, Issue 6, p. 930-934 https://doi.org/10.1021/cs300192z	journal	April 2012
Continuous production of 5-hydroxymethylfurfural from fructose: a design case study Torres, Ana I.; Daoutidis, Prodromos; Tsapatsis, Michael Energy & Environmental Science, Vol. 3, Issue 10 https://doi.org/10.1039/c0ee00082e	journal	January 2010
Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources van Putten, Robert-Jan; van der Waal, Jan C.; de Jong, Ed Chemical Reviews, Vol. 113, Issue 3 https://doi.org/10.1021/cr300182k	journal	February 2013
Selective hydrolysis of cellulose into glucose over solid acid catalysts Onda, Ayumu; Ochi, Takafumi; Yanagisawa, Kazumichi Green Chemistry, Vol. 10, Issue 10 https://doi.org/10.1039/b808471h	journal	January 2008
Optimal design and operation of SMB bioreactor: production of high fructose syrup by isomerization of glucose Zhang, Yan; Hidajat, Kus; Ray, Ajay K. Biochemical Engineering Journal, Vol. 21, Issue 2, p. 111-121 https://doi.org/10.1016/j.bej.2004.05.007	journal	October 2004
Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering Huber, George W.; Iborra, Sara; Corma, Avelino Chemical Reviews, Vol. 106, Issue 9, p. 4044-4098 https://doi.org/10.1021/cr068360d	journal	September 2006
Elucidating the Roles of Zeolite H-BEA in Aqueous-Phase Fructose Dehydration and HMF Rehydration Kruger, Jacob S.; Choudhary, Vinit; Nikolakis, Vladimiros ACS Catalysis, Vol. 3, Issue 6 https://doi.org/10.1021/cs4002157	journal	April 2013
State of the art of Lewis acid-containing zeolites: lessons from fine chemistry to new biomass transformation processes Moliner, Manuel Dalton Trans., Vol. 43, Issue 11 https://doi.org/10.1039/C3DT52293H	journal	January 2014
Tin-containing silicates: structure-activity relations Osmundsen, C. M.; Holm, M. S.; Dahl, S. Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 468, Issue 2143, p. 2000-2016 https://doi.org/10.1098/rspa.2012.0047	journal	February 2012
Probing Lewis Acid Sites in Sn-Beta Zeolite Roy, Sounak; Bakhmutsky, Kevin; Mahmoud, Eyas ACS Catalysis, Vol. 3, Issue 4 https://doi.org/10.1021/cs300599z	journal	February 2013
Production of liquid biofuels from renewable resources Nigam, Poonam Singh; Singh, Anoop Progress in Energy and Combustion Science, Vol. 37, Issue 1 https://doi.org/10.1016/j.pecs.2010.01.003	journal	February 2011
Diels–Alder and Dehydration Reactions of Biomass-Derived Furan and Acrylic Acid for the Synthesis of Benzoic Acid Mahmoud, Eyas; Yu, Jingye; Gorte, Raymond J. ACS Catalysis, Vol. 5, Issue 11 https://doi.org/10.1021/acscatal.5b01892	journal	October 2015
High Performance Zeolite LTA Pervaporation Membranes on Ceramic Hollow Fibers by Dipcoating−Wiping Seed Deposition Wang, Zhengbao; Ge, Qinqin; Shao, Jia Journal of the American Chemical Society, Vol. 131, Issue 20 https://doi.org/10.1021/ja901626d	journal	May 2009
Sn-zeolite beta as a heterogeneous chemoselective catalyst for Baeyer–Villiger oxidations Corma, Avelino; Nemeth, Laszlo T.; Renz, Michael Nature, Vol. 412, Issue 6845 https://doi.org/10.1038/35086546	journal	July 2001
Efficient conversion of carbohydrates into 5-ethoxymethylfurfural in ethanol catalyzed by AlCl3 Liu, Bing; Zhang, Zehui; Huang, Kecheng Fuel, Vol. 113 https://doi.org/10.1016/j.fuel.2013.06.015	journal	November 2013
Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides Chheda, Juben N.; Román-Leshkov, Yuriy; Dumesic, James A. Green Chem., Vol. 9, Issue 4, p. 342-350 https://doi.org/10.1039/B611568C	journal	January 2007
Direct transformation of carbohydrates to the biofuel 5-ethoxymethylfurfural by solid acid catalysts Li, Hu; Saravanamurugan, Shunmugavel; Yang, Song Green Chemistry, Vol. 18, Issue 3 https://doi.org/10.1039/C5GC01043H	journal	January 2016
Water-resistant solid Lewis acid catalysts: Meerwein–Ponndorf–Verley and Oppenauer reactions catalyzed by tin-beta zeolite Corma, A. Journal of Catalysis, Vol. 215, Issue 2 https://doi.org/10.1016/S0021-9517(03)00014-9	journal	April 2003
Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water Moliner, M.; Roman-Leshkov, Y.; Davis, M. E. Proceedings of the National Academy of Sciences, Vol. 107, Issue 14, p. 6164-6168 https://doi.org/10.1073/pnas.1002358107	journal	March 2010
One-Pot Synthesis of 5-(Ethoxymethyl)furfural from Glucose Using Sn-BEA and Amberlyst Catalysts Lew, Christopher M.; Rajabbeigi, Nafiseh; Tsapatsis, Michael Industrial & Engineering Chemistry Research, Vol. 51, Issue 14 https://doi.org/10.1021/ie2025536	journal	March 2012
Catalytic dehydration of C ₆ carbohydrates for the production of hydroxymethylfurfural (HMF) as a versatile platform chemical Wang, Tianfu; Nolte, Michael W.; Shanks, Brent H. Green Chem., Vol. 16, Issue 2 https://doi.org/10.1039/C3GC41365A	journal	January 2014
5-Hydroxymethylfurfural (HMF) as a building block platform: Biological properties, synthesis and synthetic applications Rosatella, Andreia A.; Simeonov, Svilen P.; Frade, Raquel F. M. Green Chemistry, Vol. 13, Issue 4 https://doi.org/10.1039/c0gc00401d	journal	January 2011
A Continuous Flow Strategy for the Coupled Transfer Hydrogenation and Etherification of 5-(Hydroxymethyl)furfural using Lewis Acid Zeolites Lewis, Jennifer D.; Van de Vyver, Stijn; Crisci, Anthony J. ChemSusChem, Vol. 7, Issue 8 https://doi.org/10.1002/cssc.201402100	journal	July 2014
Sustainable Solvent Systems for Use in Tandem Carbohydrate Dehydration Hydrogenation Tucker, Mark H.; Alamillo, Ricardo; Crisci, Anthony J. ACS Sustainable Chemistry & Engineering, Vol. 1, Issue 5 https://doi.org/10.1021/sc400044d	journal	March 2013
Structural Characterization of Zeolite Beta Newsam, J. M.; Treacy, M. M. J.; Koetsier, W. T. Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 420, Issue 1859 https://doi.org/10.1098/rspa.1988.0131	journal	December 1988
Simple and Scalable Preparation of Highly Active Lewis Acidic Sn-β Hammond, Ceri; Conrad, Sabrina; Hermans, Ive Angewandte Chemie International Edition, Vol. 51, Issue 47 https://doi.org/10.1002/anie.201206193	journal	October 2012
Synthesis and pervaporation properties of NaA zeolite membranes prepared with vacuum-assisted method Huang, Aisheng; Yang, Weishen; Liu, Jie Separation and Purification Technology, Vol. 56, Issue 2 https://doi.org/10.1016/j.seppur.2007.01.020	journal	August 2007
The Production of 5-Hydroxymethylfurfural from Fructose in Isopropyl Alcohol: A Green and Efficient System Lai, Linke; Zhang, Yugen ChemSusChem, Vol. 4, Issue 12 https://doi.org/10.1002/cssc.201100489	journal	October 2011
Production and upgrading of 5-hydroxymethylfurfural using heterogeneous catalysts and biomass-derived solvents Gallo, Jean Marcel R.; Alonso, David Martin; Mellmer, Max A. Green Chem., Vol. 15, Issue 1 https://doi.org/10.1039/C2GC36536G	journal	January 2013
Conversion of glucose into furans in the presence of AlCl3 in an ethanol–water solvent system Yang, Yu; Hu, Changwei; Abu-Omar, Mahdi M. Bioresource Technology, Vol. 116 https://doi.org/10.1016/j.biortech.2012.03.126	journal	July 2012

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Title: Glucose Conversion to Furans in Alcohols Catalyzed by Lewis Acidic Beta Zeolites and Brønsted Acidic Resins

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