Hydrogenation of levoglucosenone to renewable chemicals

Krishna, Siddarth H.; McClelland, Daniel J.; Rashke, Quinn A.; Dumesic, James A.; Huber, George W.

doi:10.1039/C6GC03028A

Title: Hydrogenation of levoglucosenone to renewable chemicals

Abstract

Here, we have studied the hydrogenation of levoglucosenone (LGO) to dihydrolevoglucosenone (Cyrene), levoglucosanol (Lgol), and tetrahydrofurandimethanol (THFDM) and elucidated the reaction network over supported palladium catalysts. At low temperature (40 °C) over a Pd/Al₂O₃ catalyst, LGO is selectively hydrogenated to Cyrene. At intermediate temperatures (100 °C) over a Pd/Al₂O₃ catalyst, Cyrene is selectively hydrogenated to Lgol, with an excess of the exo-Lgol isomer produced over the endo-Lgol isomer. At higher temperatures (150 °C) over a bifunctional Pd/SiO₂–Al₂O₃ catalyst, Lgol is converted to THFDM in 58% selectivity, with 78% overall selectivity to 1,6-hexanediol precursors. The ratio of cis-THFDM relative to trans-THFDM is approximately 2.5, and this ratio is independent of the Lgol feed stereoisomer ratio. Finally, tetrahydropyran-2-methanol-5-ketone (THP2M5one) and tetrahydropyran-2-methanol-5-hydroxyl (THP2M5H) are side-products of Lgol hydrogenolysis, but neither of these species are precursors to THFDM.

Authors:

Krishna, Siddarth H. ^[1]; McClelland, Daniel J. ^[1]; Rashke, Quinn A. ^[1]; Dumesic, James A. ^[1];

^[1]

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

Publication Date:: Mon Dec 12 00:00:00 EST 2016

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:: 1477850

Grant/Contract Number:: EE0006878

Resource Type:: Accepted Manuscript

Journal Name:: Green Chemistry

Additional Journal Information:: Journal Volume: 19; Journal Issue: 5; Journal ID: ISSN 1463-9262

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Krishna, Siddarth H., McClelland, Daniel J., Rashke, Quinn A., Dumesic, James A., and Huber, George W. Hydrogenation of levoglucosenone to renewable chemicals.  United States: N. p., 2016. 
Web.  doi:10.1039/C6GC03028A.

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                    Krishna, Siddarth H., McClelland, Daniel J., Rashke, Quinn A., Dumesic, James A., & Huber, George W. Hydrogenation of levoglucosenone to renewable chemicals.  United States.  https://doi.org/10.1039/C6GC03028A

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                    Krishna, Siddarth H., McClelland, Daniel J., Rashke, Quinn A., Dumesic, James A., and Huber, George W. Mon .  
"Hydrogenation of levoglucosenone to renewable chemicals".  United States.  https://doi.org/10.1039/C6GC03028A.  https://www.osti.gov/servlets/purl/1477850.

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@article{osti_1477850,

  title        = {Hydrogenation of levoglucosenone to renewable chemicals},

  author       = {Krishna, Siddarth H. and McClelland, Daniel J. and Rashke, Quinn A. and Dumesic, James A. and Huber, George W.},

  abstractNote = {Here, we have studied the hydrogenation of levoglucosenone (LGO) to dihydrolevoglucosenone (Cyrene), levoglucosanol (Lgol), and tetrahydrofurandimethanol (THFDM) and elucidated the reaction network over supported palladium catalysts. At low temperature (40 °C) over a Pd/Al2O3 catalyst, LGO is selectively hydrogenated to Cyrene. At intermediate temperatures (100 °C) over a Pd/Al2O3 catalyst, Cyrene is selectively hydrogenated to Lgol, with an excess of the exo-Lgol isomer produced over the endo-Lgol isomer. At higher temperatures (150 °C) over a bifunctional Pd/SiO2–Al2O3 catalyst, Lgol is converted to THFDM in 58% selectivity, with 78% overall selectivity to 1,6-hexanediol precursors. The ratio of cis-THFDM relative to trans-THFDM is approximately 2.5, and this ratio is independent of the Lgol feed stereoisomer ratio. Finally, tetrahydropyran-2-methanol-5-ketone (THP2M5one) and tetrahydropyran-2-methanol-5-hydroxyl (THP2M5H) are side-products of Lgol hydrogenolysis, but neither of these species are precursors to THFDM.},

  doi          = {10.1039/C6GC03028A},

  journal      = {Green Chemistry},

  number       = 5,

  volume       = 19,

  place        = {United States},

  year         = {Mon Dec 12 00:00:00 EST 2016},

  month        = {Mon Dec 12 00:00:00 EST 2016}

}

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Bio-available Solvent Cyrene: Synthesis, Derivatization, and Applications
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Similar Records

Title: Hydrogenation of levoglucosenone to renewable chemicals

Abstract

Citation Formats

Selective heterogeneously catalyzed hydrogenations journal, September 1997

Emerging catalytic processes for the production of adipic acid journal, January 2013

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

Brønsted acidity of amorphous silica–alumina: The molecular rules of proton transfer journal, December 2011

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

The selective hydrogenation of biomass-derived 5-hydroxymethylfurfural using heterogeneous catalysts journal, January 2012

Effect of rhodium precursor and thermal treatment on the hydrogenation of 2-cyclohexenone on Rh/SiO 2 Catalysts journal, December 1999

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

Dihydrolevoglucosenone (Cyrene) As a Green Alternative to N,N -Dimethylformamide (DMF) in MOF Synthesis journal, October 2016

Synthesis of a simple chiral auxiliary derived from levoglucosenone and its application in a Diels–Alder reaction journal, March 2009

From 5-Hydroxymethylfurfural (HMF) to Polymer Precursors: Catalyst Screening Studies on the Conversion of 1,2,6-hexanetriol to 1,6-hexanediol journal, July 2012

Some reactions of levoglucosenone journal, June 1979

Upgrading biomass-derived furans via acid-catalysis/hydrogenation: the remarkable difference between water and methanol as the solvent journal, January 2015

Formation of acid sites in amorphous silica-alumina journal, January 2010

Selective Hydrogenolysis of Polyols and Cyclic Ethers over Bifunctional Surface Sites on Rhodium–Rhenium Catalysts journal, August 2011

Chemoselective hydrogenation of carbonyl compounds over heterogeneous catalysts journal, September 2005

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

On the selective acid-catalysed dehydration of 1,2,6-hexanetriol journal, January 2014

Catalyst studies on the ring opening of tetrahydrofuran–dimethanol to 1,2,6-hexanetriol journal, July 2013

Direct Synthesis of 1,6-Hexanediol from HMF over a Heterogeneous Pd/ZrP Catalyst using Formic Acid as Hydrogen Source journal, November 2013

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

Recent Catalytic Advances in the Chemistry of Substituted Furans from Carbohydrates and in the Ensuing Polymers journal, February 2004

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

Homogeneous catalysed hydrogenation of HMF journal, January 2018

Catalytic production of hexane-1,2,5,6-tetrol from bio-renewable levoglucosanol in water: effect of metal and acid sites on (stereo)-selectivity journal, January 2018

Cyrene as a bio-based solvent for HATU mediated amide coupling journal, January 2018

CNN pincer ruthenium complexes for efficient transfer hydrogenation of biomass-derived carbonyl compounds journal, January 2020

Catalytic hydrogenation of dihydrolevoglucosenone to levoglucosanol with a hydrotalcite/mixed oxide copper catalyst journal, January 2019

Tuning zirconia-supported metal catalysts for selective one-step hydrogenation of levoglucosenone journal, January 2019

Aerobic oxidation of C 4 –C 6 α,ω-diols to the diacids in base-free medium over zirconia-supported (bi)metallic catalysts journal, January 2019

Selective heterogeneously catalyzed hydrogenations
journal, September 1997

Emerging catalytic processes for the production of adipic acid
journal, January 2013

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

Brønsted acidity of amorphous silica–alumina: The molecular rules of proton transfer
journal, December 2011

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

The selective hydrogenation of biomass-derived 5-hydroxymethylfurfural using heterogeneous catalysts
journal, January 2012

Effect of rhodium precursor and thermal treatment on the hydrogenation of 2-cyclohexenone on Rh/SiO 2 Catalysts
journal, December 1999

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

Dihydrolevoglucosenone (Cyrene) As a Green Alternative to N,N -Dimethylformamide (DMF) in MOF Synthesis
journal, October 2016

Synthesis of a simple chiral auxiliary derived from levoglucosenone and its application in a Diels–Alder reaction
journal, March 2009

From 5-Hydroxymethylfurfural (HMF) to Polymer Precursors: Catalyst Screening Studies on the Conversion of 1,2,6-hexanetriol to 1,6-hexanediol
journal, July 2012

Some reactions of levoglucosenone
journal, June 1979

Upgrading biomass-derived furans via acid-catalysis/hydrogenation: the remarkable difference between water and methanol as the solvent
journal, January 2015

Formation of acid sites in amorphous silica-alumina
journal, January 2010

Selective Hydrogenolysis of Polyols and Cyclic Ethers over Bifunctional Surface Sites on Rhodium–Rhenium Catalysts
journal, August 2011

Chemoselective hydrogenation of carbonyl compounds over heterogeneous catalysts
journal, September 2005

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

On the selective acid-catalysed dehydration of 1,2,6-hexanetriol
journal, January 2014

Catalyst studies on the ring opening of tetrahydrofuran–dimethanol to 1,2,6-hexanetriol
journal, July 2013

Direct Synthesis of 1,6-Hexanediol from HMF over a Heterogeneous Pd/ZrP Catalyst using Formic Acid as Hydrogen Source
journal, November 2013

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

Recent Catalytic Advances in the Chemistry of Substituted Furans from Carbohydrates and in the Ensuing Polymers
journal, February 2004

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

Homogeneous catalysed hydrogenation of HMF
journal, January 2018

Catalytic production of hexane-1,2,5,6-tetrol from bio-renewable levoglucosanol in water: effect of metal and acid sites on (stereo)-selectivity
journal, January 2018

Cyrene as a bio-based solvent for HATU mediated amide coupling
journal, January 2018

CNN pincer ruthenium complexes for efficient transfer hydrogenation of biomass-derived carbonyl compounds
journal, January 2020

Catalytic hydrogenation of dihydrolevoglucosenone to levoglucosanol with a hydrotalcite/mixed oxide copper catalyst
journal, January 2019

Tuning zirconia-supported metal catalysts for selective one-step hydrogenation of levoglucosenone
journal, January 2019

Aerobic oxidation of C 4 –C 6 α,ω-diols to the diacids in base-free medium over zirconia-supported (bi)metallic catalysts
journal, January 2019