Catalytic dehydration of levoglucosan to levoglucosenone using Brønsted solid acid catalysts in tetrahydrofuran

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

doi:10.1039/C9GC01526D

Title: Catalytic dehydration of levoglucosan to levoglucosenone using Brønsted solid acid catalysts in tetrahydrofuran

Abstract

We explored the production of levoglucosenone from levoglucosan using propylsulfonic acid functionalized silica; 59% selectivity was obtained at 100% conversion.

Authors:

^[1];

^[2];

^[1]

Department of Chemical Engineering, University of Puerto Rico, Mayagüez, Puerto Rico
Department of Chemical and Biological Engineering, University of Wisconsin, Madison, USA

Publication Date:: Mon Sep 16 00:00:00 EDT 2019

Sponsoring Org.:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

OSTI Identifier:: 1542540

Grant/Contract Number:: EE0006878

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Green Chemistry

Additional Journal Information:: Journal Name: Green Chemistry Journal Volume: 21 Journal Issue: 18; Journal ID: ISSN 1463-9262

Publisher:: Royal Society of Chemistry (RSC)

Country of Publication:: United Kingdom

Language:: English

Citation Formats


                    Oyola-Rivera, Oscar, He, Jiayue, Huber, George W., Dumesic, James A., and Cardona-Martínez, Nelson. Catalytic dehydration of levoglucosan to levoglucosenone using Brønsted solid acid catalysts in tetrahydrofuran.  United Kingdom: N. p., 2019. 
Web.  doi:10.1039/C9GC01526D.

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                    Oyola-Rivera, Oscar, He, Jiayue, Huber, George W., Dumesic, James A., & Cardona-Martínez, Nelson. Catalytic dehydration of levoglucosan to levoglucosenone using Brønsted solid acid catalysts in tetrahydrofuran.  United Kingdom.  https://doi.org/10.1039/C9GC01526D

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                    Oyola-Rivera, Oscar, He, Jiayue, Huber, George W., Dumesic, James A., and Cardona-Martínez, Nelson. Mon .  
"Catalytic dehydration of levoglucosan to levoglucosenone using Brønsted solid acid catalysts in tetrahydrofuran".  United Kingdom.  https://doi.org/10.1039/C9GC01526D.

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@article{osti_1542540,

  title        = {Catalytic dehydration of levoglucosan to levoglucosenone using Brønsted solid acid catalysts in tetrahydrofuran},

  author       = {Oyola-Rivera, Oscar and He, Jiayue and Huber, George W. and Dumesic, James A. and Cardona-Martínez, Nelson},

  abstractNote = {We explored the production of levoglucosenone from levoglucosan using propylsulfonic acid functionalized silica; 59% selectivity was obtained at 100% conversion.},

  doi          = {10.1039/C9GC01526D},

  journal      = {Green Chemistry},

  number       = 18,

  volume       = 21,

  place        = {United Kingdom},

  year         = {Mon Sep 16 00:00:00 EDT 2019},

  month        = {Mon Sep 16 00:00:00 EDT 2019}

}

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https://doi.org/10.1039/C9GC01526D

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Title: Catalytic dehydration of levoglucosan to levoglucosenone using Brønsted solid acid catalysts in tetrahydrofuran

Abstract

Citation Formats

Characterization of Large-Pore MCM-41 Molecular Sieves Obtained via Hydrothermal Restructuring journal, November 1997

Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels journal, January 2014

Solvent Effects in Acid-Catalyzed Biomass Conversion Reactions journal, September 2014

Dehydration of cellulose to levoglucosenone using polar aprotic solvents journal, January 2015

Direct Syntheses of Ordered SBA-15 Mesoporous Silica Containing Sulfonic Acid Groups journal, August 2000

Catalytic production of sugars and lignin from agricultural residues using dilute sulfuric acid in γ-valerolactone journal, December 2018

A roadmap for conversion of lignocellulosic biomass to chemicals and fuels journal, August 2012

Biomass feedstocks for renewable fuel production: a review of the impacts of feedstock and pretreatment on the yield and product distribution of fast pyrolysis bio-oils and vapors journal, January 2014

A new perspective in bio-refining: levoglucosenone and cleaner lignin from waste biorefinery hydrolysis lignin by selective conversion of residual saccharides journal, January 2016

Catalytic conversion of lignocellulosic biomass to fine chemicals and fuels journal, January 2011

Acid-Functionalized SBA-15-Type Periodic Mesoporous Organosilicas and Their Use in the Continuous Production of 5-Hydroxymethylfurfural journal, July 2012

Some reactions of levoglucosenone journal, June 1979

Stable complex formation with boric acid in pyrolysis of levoglucosan in acidic media journal, May 2008

Sulfonic acid functionalized mesoporous SBA-15 as catalyst for styrene carbonate synthesis from CO2 and styrene oxide at moderate reaction conditions journal, June 2015

Relations between Pore Structure Parameters and Their Implications for Characterization of MCM-41 Using Gas Adsorption and X-ray Diffraction journal, February 1999

Feasibility of broadening the feedstock choice for levoglucosenone production by acid pre-treatment of wood and catalytic pyrolysis of the obtained lignocellulose journal, September 2013

Yield of 1,6-anhydro-3,4-dideoxy-β-d-glycero-hex-3-enopyranos-2-ulose (levoglucosenone) on the acid-catalyzed pyrolysis of cellulose and 1,6-anhydro-β-d-glucopyranose (levoglucosan) journal, November 1975

Elucidating the Bimodal Acid−Base Behavior of the Water−Silica Interface from First Principles journal, December 2009

Production of levoglucosenone and 5-hydroxymethylfurfural from cellulose in polar aprotic solvent–water mixtures journal, January 2017

Sulfonic acid-functionalized periodic mesoporous organosilica journal, May 2003

Total Synthesis of (+)-Chloriolide journal, April 2014

Levoglucosenone (1,6-anhydro-3,4-dideoxy-.DELTA.3-.beta.-D-pyranosen-2-one). Major product of the acid-catalyzed pyrolysis of cellulose and related carbohydrates journal, January 1973

Characterization of the Porous Structure of SBA-15 journal, July 2000

Investigation of Ammonium Ion Removal from Aqueous Solutions Using Arene- and Propylsulfonic Acid Functionalized Mesoporous Silica Adsorbents journal, January 2014

Design, Synthesis, and Biological Evaluation of Levoglucosenone-Derived Ras Activation Inhibitors journal, April 2009

Catalytic Fast Pyrolysis of Cellulose to Prepare Levoglucosenone Using Sulfated Zirconia journal, November 2010

Aqueous-sensitive reaction sites in sulfonic acid-functionalized mesoporous silicas journal, March 2008

Catalytic conversion of biomass to biofuels journal, January 2010

Enhanced catalysis under flow conditions using SiliaBond functionalized silica gels journal, January 2011

Production of Levoglucosan by Pyrolysis of Carbohydrates. Pyrolysis in Hot Inert Gas Stream journal, March 1970

Improvement of the Kruk−Jaroniec−Sayari Method for Pore Size Analysis of Ordered Silicas with Cylindrical Mesopores journal, August 2006

Bifunctional Materials for the Catalytic Conversion of Cellulose into Soluble Renewable Biorefinery Feedstocks journal, April 2012

Characterization of Large-Pore MCM-41 Molecular Sieves Obtained via Hydrothermal Restructuring
journal, November 1997

Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels
journal, January 2014

Solvent Effects in Acid-Catalyzed Biomass Conversion Reactions
journal, September 2014

Dehydration of cellulose to levoglucosenone using polar aprotic solvents
journal, January 2015

Direct Syntheses of Ordered SBA-15 Mesoporous Silica Containing Sulfonic Acid Groups
journal, August 2000

Catalytic production of sugars and lignin from agricultural residues using dilute sulfuric acid in γ-valerolactone
journal, December 2018

A roadmap for conversion of lignocellulosic biomass to chemicals and fuels
journal, August 2012

Biomass feedstocks for renewable fuel production: a review of the impacts of feedstock and pretreatment on the yield and product distribution of fast pyrolysis bio-oils and vapors
journal, January 2014

A new perspective in bio-refining: levoglucosenone and cleaner lignin from waste biorefinery hydrolysis lignin by selective conversion of residual saccharides
journal, January 2016

Catalytic conversion of lignocellulosic biomass to fine chemicals and fuels
journal, January 2011

Acid-Functionalized SBA-15-Type Periodic Mesoporous Organosilicas and Their Use in the Continuous Production of 5-Hydroxymethylfurfural
journal, July 2012

Some reactions of levoglucosenone
journal, June 1979

Stable complex formation with boric acid in pyrolysis of levoglucosan in acidic media
journal, May 2008

Sulfonic acid functionalized mesoporous SBA-15 as catalyst for styrene carbonate synthesis from CO2 and styrene oxide at moderate reaction conditions
journal, June 2015

Relations between Pore Structure Parameters and Their Implications for Characterization of MCM-41 Using Gas Adsorption and X-ray Diffraction
journal, February 1999

Feasibility of broadening the feedstock choice for levoglucosenone production by acid pre-treatment of wood and catalytic pyrolysis of the obtained lignocellulose
journal, September 2013

Yield of 1,6-anhydro-3,4-dideoxy-β-d-glycero-hex-3-enopyranos-2-ulose (levoglucosenone) on the acid-catalyzed pyrolysis of cellulose and 1,6-anhydro-β-d-glucopyranose (levoglucosan)
journal, November 1975

Elucidating the Bimodal Acid−Base Behavior of the Water−Silica Interface from First Principles
journal, December 2009

Production of levoglucosenone and 5-hydroxymethylfurfural from cellulose in polar aprotic solvent–water mixtures
journal, January 2017

Sulfonic acid-functionalized periodic mesoporous organosilica
journal, May 2003

Total Synthesis of (+)-Chloriolide
journal, April 2014

Levoglucosenone (1,6-anhydro-3,4-dideoxy-.DELTA.3-.beta.-D-pyranosen-2-one). Major product of the acid-catalyzed pyrolysis of cellulose and related carbohydrates
journal, January 1973

Characterization of the Porous Structure of SBA-15
journal, July 2000

Investigation of Ammonium Ion Removal from Aqueous Solutions Using Arene- and Propylsulfonic Acid Functionalized Mesoporous Silica Adsorbents
journal, January 2014

Design, Synthesis, and Biological Evaluation of Levoglucosenone-Derived Ras Activation Inhibitors
journal, April 2009

Catalytic Fast Pyrolysis of Cellulose to Prepare Levoglucosenone Using Sulfated Zirconia
journal, November 2010

Aqueous-sensitive reaction sites in sulfonic acid-functionalized mesoporous silicas
journal, March 2008

Catalytic conversion of biomass to biofuels
journal, January 2010

Enhanced catalysis under flow conditions using SiliaBond functionalized silica gels
journal, January 2011

Production of Levoglucosan by Pyrolysis of Carbohydrates. Pyrolysis in Hot Inert Gas Stream
journal, March 1970

Improvement of the Kruk−Jaroniec−Sayari Method for Pore Size Analysis of Ordered Silicas with Cylindrical Mesopores
journal, August 2006

Bifunctional Materials for the Catalytic Conversion of Cellulose into Soluble Renewable Biorefinery Feedstocks
journal, April 2012