Kinetics of Levoglucosenone Isomerization

doi:https://doi.org/10.1002/cssc.201601308

Title: Kinetics of Levoglucosenone Isomerization

Abstract

In this paper, we studied the acid-catalyzed isomerization of levoglucosenone (LGO) to 5-hydroxymethylfurfural (HMF) and developed a reaction kinetics model that describes the experimental data across a range of conditions (100–150 °C, 50–100 mm H ₂SO ₄, 50–150 mm LGO). LGO and its hydrated derivative exist in equilibrium under these reaction conditions. Thermal and catalytic degradation of HMF are the major sources of carbon loss. Within the range of conditions studied, higher temperatures and shorter reaction times favor the production of HMF. The yields of HMF and levulinic acid decrease monotonically as tetrahydrofuran is added to the aqueous solvent system, indicating that water plays a role in the LGO isomerization reaction. Initial-rate analyses show that HMF is produced solely from LGO rather than from the hydrated derivative of LGO. Finally, the results of this study are consistent with a mechanism for LGO isomerization that proceeds through hydration of the anhydro bridge, followed by ring rearrangement analogous to the isomerization of glucose to fructose.

Authors:

Krishna, Siddarth H. ^[1]; Walker, Theodore W. ^[1]; Dumesic, James A. ^[1];

^[1]

Univ. of Wisconsin, Madison, WI (United States). Department of Chemical and Biological Engineering

Publication Date:: 2016-12-15

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

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

Contributing Org.:: University of Wisconsin-Madison Department of Chemistry

OSTI Identifier:: 1477849

Grant/Contract Number:: EE0006878

Resource Type:: Journal Article: Accepted Manuscript

Journal Name:: ChemSusChem

Additional Journal Information:: Journal Volume: 10; Journal Issue: 1; Journal ID: ISSN 1864-5631

Publisher:: ChemPubSoc Europe

Country of Publication:: United States

Language:: English

Subject:: 59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 5-hydroxymethylfurfural; biomass; isomerization; kinetics; levoglucosenone

Citation Formats


                    Krishna, Siddarth H., Walker, Theodore W., Dumesic, James A., and Huber, George W. Kinetics of Levoglucosenone Isomerization.  United States: N. p., 2016. 
        Web.  doi:10.1002/cssc.201601308.

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                    Krishna, Siddarth H., Walker, Theodore W., Dumesic, James A., & Huber, George W. Kinetics of Levoglucosenone Isomerization.  United States.  https://doi.org/10.1002/cssc.201601308

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                    Krishna, Siddarth H., Walker, Theodore W., Dumesic, James A., and Huber, George W. Thu .  
        "Kinetics of Levoglucosenone Isomerization".  United States.  https://doi.org/10.1002/cssc.201601308.  https://www.osti.gov/servlets/purl/1477849.

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@article{osti_1477849,

  title        = {Kinetics of Levoglucosenone Isomerization},

  author       = {Krishna, Siddarth H. and Walker, Theodore W. and Dumesic, James A. and Huber, George W.},

  abstractNote = {In this paper, we studied the acid-catalyzed isomerization of levoglucosenone (LGO) to 5-hydroxymethylfurfural (HMF) and developed a reaction kinetics model that describes the experimental data across a range of conditions (100–150 °C, 50–100 mm H2SO4, 50–150 mm LGO). LGO and its hydrated derivative exist in equilibrium under these reaction conditions. Thermal and catalytic degradation of HMF are the major sources of carbon loss. Within the range of conditions studied, higher temperatures and shorter reaction times favor the production of HMF. The yields of HMF and levulinic acid decrease monotonically as tetrahydrofuran is added to the aqueous solvent system, indicating that water plays a role in the LGO isomerization reaction. Initial-rate analyses show that HMF is produced solely from LGO rather than from the hydrated derivative of LGO. Finally, the results of this study are consistent with a mechanism for LGO isomerization that proceeds through hydration of the anhydro bridge, followed by ring rearrangement analogous to the isomerization of glucose to fructose.},

  doi          = {10.1002/cssc.201601308},

  url          = {https://www.osti.gov/biblio/1477849},
  journal      = {ChemSusChem},

  issn         = {1864-5631},

  number       = 1,

  volume       = 10,

  place        = {United States},

  year         = {2016},

  month        = {12}

}

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Katalytische Flüssigphasenumwandlung oxygenierter Kohlenwasserstoffe aus Biomasse zu Treibstoffen und Rohstoffen für die Chemiewirtschaft
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Works referencing / citing this record:

New catalytic strategies for α,ω-diols production from lignocellulosic biomass
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Bouxin, Florent P.; Clark, James H.; Fan, Jiajun
Green Chemistry, Vol. 21, Issue 6
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Enzymatic reduction of levoglucosenone by an alkene reductase (OYE 2.6): a sustainable metal- and dihydrogen-free access to the bio-based solvent Cyrene®
journal, January 2018

Mouterde, Louis M. M.; Allais, Florent; Stewart, Jon D.
Green Chemistry, Vol. 20, Issue 24
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journal (1)

Title: Kinetics of Levoglucosenone Isomerization

Abstract

Citation Formats

Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates journal, June 2007

Kinetics of Non-catalyzed Decomposition of Glucose in High-temperature Liquid Water journal, December 2008

Liquid-Phase Catalytic Processing of Biomass-Derived Oxygenated Hydrocarbons to Fuels and Chemicals journal, September 2007

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

Hydrochloric acid-catalyzed levulinic acid formation from cellulose: data and kinetic model to maximize yields journal, March 2011

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

Caprolactam from Renewable Resources: Catalytic Conversion of 5-Hydroxymethylfurfural into Caprolactone journal, June 2011

Caprolactam from Renewable Resources: Catalytic Conversion of 5-Hydroxymethylfurfural into Caprolactone journal, June 2011

Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering journal, September 2006

A kinetic study on the decomposition of 5-hydroxymethylfurfural into levulinic acid journal, January 2006

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

Some reactions of levoglucosenone journal, June 1979

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

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

Production of liquid hydrocarbon fuels by catalytic conversion of biomass-derived levulinic acid journal, January 2011

Catalytic Isomerization of Biomass-Derived Aldoses: A Review journal, March 2016

Kinetics and Reaction Engineering of Levulinic Acid Production from Aqueous Glucose Solutions journal, June 2012

Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents journal, January 2014

Synthesis of 1,6-hexanediol from HMF over double-layered catalysts of Pd/SiO 2 + Ir–ReO x /SiO 2 in a fixed-bed reactor journal, January 2016

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

Kinetic Study on the Acid-Catalyzed Hydrolysis of Cellulose to Levulinic Acid journal, March 2007

Catalytic Conversion of Fructose, Glucose, and Sucrose to 5-(Hydroxymethyl)furfural and Levulinic and Formic Acids in γ-Valerolactone As a Green Solvent journal, April 2014

Catalytic pyrolysis of cellulose in sulfolane with some acidic catalysts journal, April 2007

A two-step approach for the catalytic conversion of glucose to 2,5-dimethylfuran in ionic liquids journal, January 2010

Katalytische Flüssigphasenumwandlung oxygenierter Kohlenwasserstoffe aus Biomasse zu Treibstoffen und Rohstoffen für die Chemiewirtschaft journal, September 2007

3-Deoxy-glucosone is an Intermediate in the Formation of Furfurals from D-Glucose. journal, June 2011

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

New catalytic strategies for α,ω-diols production from lignocellulosic biomass journal, January 2017

Bio-available Solvent Cyrene: Synthesis, Derivatization, and Applications journal, August 2018

Novel hybrid process for the conversion of microcrystalline cellulose to value-added chemicals: part 3: detailed reaction pathway journal, January 2019

Combining steam distillation with microwave-assisted pyrolysis to maximise direct production of levoglucosenone from agricultural wastes journal, January 2019

Enzymatic reduction of levoglucosenone by an alkene reductase (OYE 2.6): a sustainable metal- and dihydrogen-free access to the bio-based solvent Cyrene® journal, January 2018

Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates
journal, June 2007

Kinetics of Non-catalyzed Decomposition of Glucose in High-temperature Liquid Water
journal, December 2008

Liquid-Phase Catalytic Processing of Biomass-Derived Oxygenated Hydrocarbons to Fuels and Chemicals
journal, September 2007

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

Hydrochloric acid-catalyzed levulinic acid formation from cellulose: data and kinetic model to maximize yields
journal, March 2011

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

Caprolactam from Renewable Resources: Catalytic Conversion of 5-Hydroxymethylfurfural into Caprolactone
journal, June 2011

Caprolactam from Renewable Resources: Catalytic Conversion of 5-Hydroxymethylfurfural into Caprolactone
journal, June 2011

Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering
journal, September 2006

A kinetic study on the decomposition of 5-hydroxymethylfurfural into levulinic acid
journal, January 2006

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

Some reactions of levoglucosenone
journal, June 1979

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

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

Production of liquid hydrocarbon fuels by catalytic conversion of biomass-derived levulinic acid
journal, January 2011

Catalytic Isomerization of Biomass-Derived Aldoses: A Review
journal, March 2016

Kinetics and Reaction Engineering of Levulinic Acid Production from Aqueous Glucose Solutions
journal, June 2012

Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents
journal, January 2014

Synthesis of 1,6-hexanediol from HMF over double-layered catalysts of Pd/SiO ₂ + Ir–ReO _x /SiO ₂ in a fixed-bed reactor
journal, January 2016

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

Kinetic Study on the Acid-Catalyzed Hydrolysis of Cellulose to Levulinic Acid
journal, March 2007

Catalytic Conversion of Fructose, Glucose, and Sucrose to 5-(Hydroxymethyl)furfural and Levulinic and Formic Acids in γ-Valerolactone As a Green Solvent
journal, April 2014

Catalytic pyrolysis of cellulose in sulfolane with some acidic catalysts
journal, April 2007

A two-step approach for the catalytic conversion of glucose to 2,5-dimethylfuran in ionic liquids
journal, January 2010

Katalytische Flüssigphasenumwandlung oxygenierter Kohlenwasserstoffe aus Biomasse zu Treibstoffen und Rohstoffen für die Chemiewirtschaft
journal, September 2007

3-Deoxy-glucosone is an Intermediate in the Formation of Furfurals from D-Glucose.
journal, June 2011

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

New catalytic strategies for α,ω-diols production from lignocellulosic biomass
journal, January 2017

Bio-available Solvent Cyrene: Synthesis, Derivatization, and Applications
journal, August 2018

Novel hybrid process for the conversion of microcrystalline cellulose to value-added chemicals: part 3: detailed reaction pathway
journal, January 2019

Combining steam distillation with microwave-assisted pyrolysis to maximise direct production of levoglucosenone from agricultural wastes
journal, January 2019

Enzymatic reduction of levoglucosenone by an alkene reductase (OYE 2.6): a sustainable metal- and dihydrogen-free access to the bio-based solvent Cyrene®
journal, January 2018