Catalytic conversion of cellulose to levoglucosenone using propylsulfonic acid functionalized SBA-15 and H2SO4 in tetrahydrofuran

Oyola-Rivera, Oscar; He, Jiayue; Huber, George W.; Dumesic, James A.; Cardona-Martínez, Nelson

doi:10.1016/j.biombioe.2021.106315

Title: Catalytic conversion of cellulose to levoglucosenone using propylsulfonic acid functionalized SBA-15 and H₂SO₄ in tetrahydrofuran

Journal Article · Fri Nov 26 00:00:00 EST 2021 · Biomass and Bioenergy

DOI:https://doi.org/10.1016/j.biombioe.2021.106315· OSTI ID:1976888

Oyola-Rivera, Oscar ^[1]; He, Jiayue ^[2];

^[2]; Dumesic, James A. ^[2]; Cardona-Martínez, Nelson ^[1]

University of Puerto Rico, Mayaguez (Puerto Rico)
University of Wisconsin, Madison, WI (United States)

The catalytic conversion of cellulose to levoglucosenone (LGO) was studied using dilute sulfuric acid and propylsulfonic acid functionalized SBA-15 (PS-SBA-15) in tetrahydrofuran (THF). Here we show that the addition of small amounts of a liquid acid catalyst such as sulfuric acid complements the use of a solid acid catalyst for the conversion of cellulose. Sulfuric acid promotes the depolymerization of cellulose into levoglucosan (LGA). The main role of the solid Brønsted acid catalyst is to dehydrate the LGA into LGO. The addition of low concentrations of H₂SO₄ to PS-SBA-15 resulted in an increase in LGO yield of up to 37% (from 18% obtained using an equivalent amount of H₂SO₄ only). Our approach provides a novel alternative for a more environmentally friendly production of LGO.

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Research Organization:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE); National Science Foundation (NSF)

Grant/Contract Number:: EE0006878; HRD-1345156

OSTI ID:: 1976888

Alternate ID(s):: OSTI ID: 1832659

Journal Information:: Biomass and Bioenergy, Vol. 156, Issue C; ISSN 0961-9534

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (42)

Characterization of Large-Pore MCM-41 Molecular Sieves Obtained via Hydrothermal Restructuring Sayari, A.; Liu, P.; Kruk, M. Chemistry of Materials, Vol. 9, Issue 11 https://doi.org/10.1021/cm970128o	journal	November 1997
Rational Design of Mixed Solvent Systems for Acid-Catalyzed Biomass Conversion Processes Using a Combined Experimental, Molecular Dynamics and Machine Learning Approach Walker, Theodore W.; Chew, Alex K.; Van Lehn, Reid C. Topics in Catalysis, Vol. 63, Issue 7-8 https://doi.org/10.1007/s11244-020-01260-9	journal	April 2020
Hydrothermal Stability of Cerium Modified Cu-ZSM-5 Catalyst for Nitric Oxide Decomposition Zhang, Yanping; Flytzani-Stephanopoulos, Maria Journal of Catalysis, Vol. 164, Issue 1 https://doi.org/10.1006/jcat.1996.0369	journal	November 1996
Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels Climent, Maria J.; Corma, Avelino; Iborra, Sara Green Chemistry, Vol. 16, Issue 2 https://doi.org/10.1039/c3gc41492b	journal	January 2014
Advances in 5-hydroxymethylfurfural production from biomass in biphasic solvents Saha, Basudeb; Abu-Omar, Mahdi M. Green Chem., Vol. 16, Issue 1 https://doi.org/10.1039/C3GC41324A	journal	January 2014
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
Solvent Effects in Acid-Catalyzed Biomass Conversion Reactions Mellmer, Max A.; Sener, Canan; Gallo, Jean Marcel R. Angewandte Chemie International Edition, Vol. 53, Issue 44 https://doi.org/10.1002/anie.201408359	journal	September 2014
Dehydration of cellulose to levoglucosenone using polar aprotic solvents Cao, Fei; Schwartz, Thomas J.; McClelland, Daniel J. Energy & Environmental Science, Vol. 8, Issue 6 https://doi.org/10.1039/C5EE00353A	journal	January 2015
Direct Syntheses of Ordered SBA-15 Mesoporous Silica Containing Sulfonic Acid Groups Margolese, D.; Melero, J. A.; Christiansen, S. C. Chemistry of Materials, Vol. 12, Issue 8 https://doi.org/10.1021/cm0010304	journal	August 2000
Catalytic production of sugars and lignin from agricultural residues using dilute sulfuric acid in γ-valerolactone Oyola-Rivera, Oscar; González-Rosario, Alexa M.; Cardona-Martínez, Nelson Biomass and Bioenergy, Vol. 119 https://doi.org/10.1016/j.biombioe.2018.09.031	journal	December 2018
The E Factor: fifteen years on Sheldon, Roger A. Green Chemistry, Vol. 9, Issue 12 https://doi.org/10.1039/b713736m	journal	January 2007
A roadmap for conversion of lignocellulosic biomass to chemicals and fuels Wettstein, Stephanie G.; Alonso, David Martin; Gürbüz, Elif I. Current Opinion in Chemical Engineering, Vol. 1, Issue 3 https://doi.org/10.1016/j.coche.2012.04.002	journal	August 2012
Formation of Anhydro-sugars in the Primary Volatiles and Solid Residues from Cellulose Fast Pyrolysis in a Wire-Mesh Reactor Gong, Xun; Yu, Yun; Gao, Xiangpeng Energy & Fuels, Vol. 28, Issue 8 https://doi.org/10.1021/ef501112q	journal	July 2014
Catalytic conversion of lignocellulosic biomass to fine chemicals and fuels Zhou, Chun-Hui; Xia, Xi; Lin, Chun-Xiang Chemical Society Reviews, Vol. 40, Issue 11 https://doi.org/10.1039/c1cs15124j	journal	January 2011
Acid-Functionalized SBA-15-Type Periodic Mesoporous Organosilicas and Their Use in the Continuous Production of 5-Hydroxymethylfurfural Tucker, Mark H.; Crisci, Anthony J.; Wigington, Bethany N. ACS Catalysis, Vol. 2, Issue 9 https://doi.org/10.1021/cs300303v	journal	July 2012
Kinetics and Mechanism of Cellulose Pyrolysis Lin, Yu-Chuan; Cho, Joungmo; Tompsett, Geoffrey A. The Journal of Physical Chemistry C, Vol. 113, Issue 46 https://doi.org/10.1021/jp906702p	journal	October 2009
Advances in the Synthesis and Catalytic Applications of Organosulfonic-Functionalized Mesostructured Materials Melero, Juan A.; van Grieken, Rafael; Morales, Gabriel Chemical Reviews, Vol. 106, Issue 9 https://doi.org/10.1021/cr050994h	journal	September 2006
Catalytic Strategies for Levoglucosenone Production by Pyrolysis of Cellulose and Lignocellulosic Biomass Kudo, Shinji; Huang, Xin; Asano, Shusaku Energy & Fuels, Vol. 35, Issue 12 https://doi.org/10.1021/acs.energyfuels.1c01062	journal	May 2021
Relations between Pore Structure Parameters and Their Implications for Characterization of MCM-41 Using Gas Adsorption and X-ray Diffraction Kruk, Michal; Jaroniec, Mietek; Sayari, Abdelhamid Chemistry of Materials, Vol. 11, Issue 2 https://doi.org/10.1021/cm981006e	journal	February 1999
Catalytic dehydration of levoglucosan to levoglucosenone using Brønsted solid acid catalysts in tetrahydrofuran Oyola-Rivera, Oscar; He, Jiayue; Huber, George W. Green Chemistry, Vol. 21, Issue 18 https://doi.org/10.1039/C9GC01526D	journal	January 2019
Pyrolytic Sugars from Cellulosic Biomass Kuzhiyil, Najeeb; Dalluge, Dustin; Bai, Xianglan ChemSusChem, Vol. 5, Issue 11 https://doi.org/10.1002/cssc.201200341	journal	September 2012
Improvement of levoglucosenone selectivity in liquid phase conversion of cellulose-derived anhydrosugar over solid acid catalysts Huang, Xin; Kudo, Shinji; Asano, Shusaku Fuel Processing Technology, Vol. 212 https://doi.org/10.1016/j.fuproc.2020.106625	journal	February 2021
Insights into the Hydrothermal Stability of ZSM-5 under Relevant Biomass Conversion Reaction Conditions Gardner, David W.; Huo, Jiajie; Hoff, Thomas C. ACS Catalysis, Vol. 5, Issue 7 https://doi.org/10.1021/acscatal.5b00888	journal	June 2015
Conversion of biomass to selected chemical products Gallezot, Pierre Chem. Soc. Rev., Vol. 41, Issue 4 https://doi.org/10.1039/C1CS15147A	journal	January 2012
Production of levoglucosenone and 5-hydroxymethylfurfural from cellulose in polar aprotic solvent–water mixtures He, Jiayue; Liu, Mingjie; Huang, Kefeng Green Chemistry, Vol. 19, Issue 15 https://doi.org/10.1039/C7GC01688C	journal	January 2017
Total Synthesis of (+)-Chloriolide Ostermeier, Michael; Schobert, Rainer The Journal of Organic Chemistry, Vol. 79, Issue 9 https://doi.org/10.1021/jo500527g	journal	April 2014
Characterization of the Porous Structure of SBA-15 Kruk, Michal; Jaroniec, Mietek; Ko, Chang Hyun Chemistry of Materials, Vol. 12, Issue 7 https://doi.org/10.1021/cm000164e	journal	July 2000
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
Metrics to ‘green’ chemistry—which are the best? Constable, David J. C.; Curzons, Alan D.; Cunningham, Virginia L. Green Chem., Vol. 4, Issue 6 https://doi.org/10.1039/B206169B	journal	January 2002
Understanding the Stability in Water of Mesoporous SBA-15 and MCM-41 Galarneau, Anne; Nader, Mirella; Guenneau, Flavien The Journal of Physical Chemistry C, Vol. 111, Issue 23 https://doi.org/10.1021/jp068526e	journal	June 2007
Design, Synthesis, and Biological Evaluation of Levoglucosenone-Derived Ras Activation Inhibitors Müller, Christian; Gomez-Zurita Frau, Maria Antonia; Ballinari, Dario ChemMedChem, Vol. 4, Issue 4 https://doi.org/10.1002/cmdc.200800416	journal	April 2009
Efficient levoglucosenone production by catalytic pyrolysis of cellulose mixed with ionic liquid Kudo, Shinji; Zhou, Zhenwei; Norinaga, Koyo Green Chemistry, Vol. 13, Issue 11 https://doi.org/10.1039/c1gc15975e	journal	January 2011
Kinetics of Levoglucosenone Isomerization Krishna, Siddarth H.; Walker, Theodore W.; Dumesic, James A. ChemSusChem, Vol. 10, Issue 1 https://doi.org/10.1002/cssc.201601308	journal	December 2016
Biorefining: Heterogeneously Catalyzed Reactions of Carbohydrates for the Production of Furfural and Hydroxymethylfurfural Karinen, Reetta; Vilonen, Kati; Niemelä, Marita ChemSusChem, Vol. 4, Issue 8 https://doi.org/10.1002/cssc.201000375	journal	July 2011
Catalytic Fast Pyrolysis of Cellulose to Prepare Levoglucosenone Using Sulfated Zirconia Wang, Zhi; Lu, Qiang; Zhu, Xi-Feng ChemSusChem, Vol. 4, Issue 1 https://doi.org/10.1002/cssc.201000210	journal	November 2010
Hydrothermal stability and catalytic activity of mesoporous aluminum-containing SBA-15 Ooi, Yean-Sang; Zakaria, Ridzuan; Mohamed, Abdul Rahman Catalysis Communications, Vol. 5, Issue 8 https://doi.org/10.1016/j.catcom.2004.05.011	journal	August 2004
Selective production of levoglucosenone by catalytic pyrolysis of cellulose mixed with magnetic solid acid Qian, Le; Xu, Feixiang; Liu, Shijun Cellulose, Vol. 28, Issue 12 https://doi.org/10.1007/s10570-021-04010-6	journal	July 2021
Catalytic conversion of biomass to biofuels Alonso, David Martin; Bond, Jesse Q.; Dumesic, James A. Green Chemistry, Vol. 12, Issue 9, p. 1493-1513 https://doi.org/10.1039/c004654j	journal	January 2010
Recent Advances in the Preparation and Applications of Organo‐functionalized Porous Materials Yadav, Rekha; Baskaran, Thangaraj; Kaiprathu, Anjali Chemistry – An Asian Journal, Vol. 15, Issue 17 https://doi.org/10.1002/asia.202000651	journal	July 2020
Fundamentals of green chemistry: efficiency in reaction design Sheldon, Roger A. Chem. Soc. Rev., Vol. 41, Issue 4 https://doi.org/10.1039/C1CS15219J	journal	January 2012
Bifunctional Materials for the Catalytic Conversion of Cellulose into Soluble Renewable Biorefinery Feedstocks Reyes-Luyanda, Damian; Flores-Cruz, Josseant; Morales-Pérez, Pedro J. Topics in Catalysis, Vol. 55, Issue 3-4 https://doi.org/10.1007/s11244-012-9791-5	journal	April 2012
Improvement of the Kruk−Jaroniec−Sayari Method for Pore Size Analysis of Ordered Silicas with Cylindrical Mesopores Jaroniec, Mietek; Solovyov, Leonid A. Langmuir, Vol. 22, Issue 16 https://doi.org/10.1021/la0609571	journal	August 2006

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Related Subjects

09 BIOMASS FUELS
cellulose
levoglucosenone
levoglucosan
SBA-15
propylsulfonic acid

Title: Catalytic conversion of cellulose to levoglucosenone using propylsulfonic acid functionalized SBA-15 and H2SO4 in tetrahydrofuran

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References (42)

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Title: Catalytic conversion of cellulose to levoglucosenone using propylsulfonic acid functionalized SBA-15 and H₂SO₄ in tetrahydrofuran