Highly efficient conversion of terpenoid biomass to jet-fuel range cycloalkanes in a biphasic tandem catalytic process

doi:https://doi.org/10.1039/C7GC00710H

Title: Highly efficient conversion of terpenoid biomass to jet-fuel range cycloalkanes in a biphasic tandem catalytic process

Abstract

The demand for bio-jet fuels to reduce carbon emissions is increasing substantially in the aviation sector, while the scarcity of high-density jet fuel components limits the use of bio-jet fuels in high-performance aircrafts compared with conventional jet fuels. In this paper, we report a novel biphasic tandem catalytic process (biTCP) for synthesizing cycloalkanes from renewable terpenoid biomass, such as 1,8-cineole. Multistep tandem reactions, including C–O ring opening by hydrolysis, dehydration, and hydrogenation, were carried out in the “one-pot” biTCP. 1,8-Cineole was efficiently converted to p-menthane at high yields (>99%) in the biTCP under mild reaction conditions. Finally, the catalytic reaction mechanism is discussed.

Authors:

^[1]; Li, Teng ^[2]; Tang, Kan ^[2]; Zhou, Xinpei ^[1]; Lu, Mi ^[1]; Ounkham, Whalmany L. ^[1]; Spain, Stephen M. ^[1]; Frost, Brian J. ^[1];

^[2]

Univ. of Nevada, Reno, NV (United States)
Washington State Univ., Pullman, WA (United States)

Publication Date:: 2017-06-12

Research Org.:: Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Sponsoring Org.:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B)

OSTI Identifier:: 1394368

DOE Contract Number:: AC05-00OR22725

Resource Type:: Journal Article

Journal Name:: Green Chemistry

Additional Journal Information:: Journal Volume: 19; Journal Issue: 15; 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


                    Yang, Xiaokun, Li, Teng, Tang, Kan, Zhou, Xinpei, Lu, Mi, Ounkham, Whalmany L., Spain, Stephen M., Frost, Brian J., and Lin, Hongfei. Highly efficient conversion of terpenoid biomass to jet-fuel range cycloalkanes in a biphasic tandem catalytic process.  United States: N. p., 2017. 
        Web.  doi:10.1039/C7GC00710H.

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                    Yang, Xiaokun, Li, Teng, Tang, Kan, Zhou, Xinpei, Lu, Mi, Ounkham, Whalmany L., Spain, Stephen M., Frost, Brian J., & Lin, Hongfei. Highly efficient conversion of terpenoid biomass to jet-fuel range cycloalkanes in a biphasic tandem catalytic process.  United States.  https://doi.org/10.1039/C7GC00710H

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                    Yang, Xiaokun, Li, Teng, Tang, Kan, Zhou, Xinpei, Lu, Mi, Ounkham, Whalmany L., Spain, Stephen M., Frost, Brian J., and Lin, Hongfei. Mon .  
        "Highly efficient conversion of terpenoid biomass to jet-fuel range cycloalkanes in a biphasic tandem catalytic process".  United States.  https://doi.org/10.1039/C7GC00710H.

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@article{osti_1394368,

  title        = {Highly efficient conversion of terpenoid biomass to jet-fuel range cycloalkanes in a biphasic tandem catalytic process},

  author       = {Yang, Xiaokun and Li, Teng and Tang, Kan and Zhou, Xinpei and Lu, Mi and Ounkham, Whalmany L. and Spain, Stephen M. and Frost, Brian J. and Lin, Hongfei},

  abstractNote = {The demand for bio-jet fuels to reduce carbon emissions is increasing substantially in the aviation sector, while the scarcity of high-density jet fuel components limits the use of bio-jet fuels in high-performance aircrafts compared with conventional jet fuels. In this paper, we report a novel biphasic tandem catalytic process (biTCP) for synthesizing cycloalkanes from renewable terpenoid biomass, such as 1,8-cineole. Multistep tandem reactions, including C–O ring opening by hydrolysis, dehydration, and hydrogenation, were carried out in the “one-pot” biTCP. 1,8-Cineole was efficiently converted to p-menthane at high yields (>99%) in the biTCP under mild reaction conditions. Finally, the catalytic reaction mechanism is discussed.},

  doi          = {10.1039/C7GC00710H},

  url          = {https://www.osti.gov/biblio/1394368},
  journal      = {Green Chemistry},

  issn         = {1463-9262},

  number       = 15,

  volume       = 19,

  place        = {United States},

  year         = {2017},

  month        = {6}

}

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Title: Highly efficient conversion of terpenoid biomass to jet-fuel range cycloalkanes in a biphasic tandem catalytic process

Abstract

Citation Formats

Catalytic Conversion of Biomass to Monofunctional Hydrocarbons and Targeted Liquid-Fuel Classes journal, October 2008

Efficient conversion of pure and mixed terpene feedstocks to high density fuels journal, July 2012

Conversion of Hemicellulose to Furfural and Levulinic Acid using Biphasic Reactors with Alkylphenol Solvents journal, January 2012

Metabolic engineering for isoprenoid-based biofuel production journal, July 2015

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Transformation of α-limonene into p-cymene over oxide catalysts: A green chemistry approach journal, March 2014

Catalytic conversion wood syngas to synthetic aviation turbine fuels over a multifunctional catalyst journal, January 2013

Functional group dependence of the acid catalyzed ring opening of biomass derived furan rings: an experimental and theoretical study journal, January 2013

Technoeconomic analysis of jet fuel production from hydrolysis, decarboxylation, and reforming of camelina oil journal, April 2015

Recent Developments in High-Energy Density Liquid Hydrocarbon Fuels journal, May 1999

Identification and microbial production of a terpene-based advanced biofuel journal, September 2011

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Opportunities for Bio-Based Solvents Created as Petrochemical and Fuel Products Transition towards Renewable Resources journal, July 2015

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The hydrodeoxygenation of bioderived furans into alkanes journal, April 2013

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Aqueous biphasic catalysis: Where the reaction takes place journal, July 1998

Microbial engineering for the production of advanced biofuels journal, August 2012

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Conversion of furfural into cyclopentanone over Ni–Cu bimetallic catalysts journal, January 2013

Aqueous-biphasic hydroformylation of alkenes promoted by “weak” surfactants journal, January 2009

Dissociation constant of aqueous trifluoroacetic acid by cryoscopy and conductivity journal, July 1981

High-energy fuels and materials from plants journal, April 1987

Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes journal, May 2011

Pd/NbOPO 4 Multifunctional Catalyst for the Direct Production of Liquid Alkanes from Aldol Adducts of Furans journal, July 2014

Biphasic Suzuki coupling reactions of aryl or benzyl bromides employing cobalt-containing phosphine ligand coordinated palladium complex journal, April 2005

Oligomerisation of isobutene with silica supported ionic liquid catalysts journal, January 2012

Gas solubilities (hydrogen, helium, nitrogen, carbon monoxide, oxygen, argon, carbon dioxide) in organic liquids at 293.2 K journal, April 1989

Industrial Aqueous Biphasic Catalysis: Status and Directions journal, March 1998

Catalytic conversion of hemicellulosic biomass to lactic acid in pH neutral aqueous phase media journal, January 2015

Bio-jet fuel conversion technologies journal, January 2016

Integrated Catalytic Process for Biomass Conversion and Upgrading to C 12 Furoin and Alkane Fuel journal, March 2014

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

Optimizing carbon efficiency of jet fuel range alkanes from cellulose co-fed with polyethylene via catalytically combined processes journal, August 2016

Low-temperature, solvent-free dehydration of cineoles with heterogeneous acid catalysts for the production of high-density biofuels: Low-temperature, solvent-free dehydration of cineoles journal, April 2014

Scale of biomass production from new woody crops for salinity control in dryland agriculture in Australia journal, January 2007

Catalytic hydrothermal deoxygenation of palmitic acid journal, January 2010

Synthesis of Jet-Fuel Range Cycloalkanes from the Mixtures of Cyclopentanone and Butanal journal, November 2015

Synthesis of 2,5-Hexanedione from Biomass Resources Using a Highly Efficient Biphasic System journal, May 2016

High-Density Renewable Fuels Based on the Selective Dimerization of Pinenes journal, January 2010

Synthesis of renewable jet and diesel fuels from 2-ethyl-1-hexene journal, January 2010

Synthesis of renewable diesel with the 2-methylfuran, butanal and acetone derived from lignocellulose journal, April 2013

The conversion of 1,8-cineole sourced from renewable Eucalyptus oil to p-cymene over a palladium doped γ-Al2O3 catalyst journal, December 2011

Catalytic Conversion of Biomass to Monofunctional Hydrocarbons and Targeted Liquid-Fuel Classes
journal, October 2008

Efficient conversion of pure and mixed terpene feedstocks to high density fuels
journal, July 2012

Conversion of Hemicellulose to Furfural and Levulinic Acid using Biphasic Reactors with Alkylphenol Solvents
journal, January 2012

Metabolic engineering for isoprenoid-based biofuel production
journal, July 2015

Eucalypts as a biofuel feedstock
journal, November 2011

Transformation of α-limonene into p-cymene over oxide catalysts: A green chemistry approach
journal, March 2014

Catalytic conversion wood syngas to synthetic aviation turbine fuels over a multifunctional catalyst
journal, January 2013

Functional group dependence of the acid catalyzed ring opening of biomass derived furan rings: an experimental and theoretical study
journal, January 2013

Technoeconomic analysis of jet fuel production from hydrolysis, decarboxylation, and reforming of camelina oil
journal, April 2015

Recent Developments in High-Energy Density Liquid Hydrocarbon Fuels
journal, May 1999

Identification and microbial production of a terpene-based advanced biofuel
journal, September 2011

Rapid Ether and Alcohol C–O Bond Hydrogenolysis Catalyzed by Tandem High-Valent Metal Triflate + Supported Pd Catalysts
journal, December 2013

Opportunities for Bio-Based Solvents Created as Petrochemical and Fuel Products Transition towards Renewable Resources
journal, July 2015

Catalytic Upgrading of Extractives to Chemicals: Monoterpenes to “EXICALS”
journal, April 2015

A techno-economic review of hydroprocessed renewable esters and fatty acids for jet fuel production
journal, January 2013

The hydrodeoxygenation of bioderived furans into alkanes
journal, April 2013

Production of renewable jet fuel range alkanes and aromatics via integrated catalytic processes of intact biomass
journal, November 2015

Aqueous biphasic catalysis: Where the reaction takes place
journal, July 1998

Microbial engineering for the production of advanced biofuels
journal, August 2012

Rapid nanoparticle-catalyzed hydrogenations in triphasic millireactors with facile catalyst recovery
journal, January 2014

Synthesis of renewable high-density fuels using cyclopentanone derived from lignocellulose
journal, January 2014

High yield conversion of cellulosic biomass into 5-hydroxymethylfurfural and a study of the reaction kinetics of cellulose to HMF conversion in a biphasic system
journal, January 2016

Renewable gasoline from aqueous phase hydrodeoxygenation of aqueous sugar solutions prepared by hydrolysis of maple wood
journal, January 2011

Bulk and fine chemicals via aqueous biphasic catalysis
journal, July 1999

Charged Defect Formation Energies in TiO<sub>2</sub> Using the Supercell Approximation
journal, October 2006

From lignin to cycloparaffins and aromatics: Directional synthesis of jet and diesel fuel range biofuels using biomass
journal, May 2015

Enhancement of jet fuel range alkanes from co-feeding of lignocellulosic biomass with plastics via tandem catalytic conversions
journal, July 2016

Terpenoid biomaterials
journal, May 2008

Preparation of trifluoroacetic acid-immobilized Fe3O4@SiO2–APTES nanocatalyst for synthesis of quinolines
journal, October 2015

Trifluoroacetic acid: Uses and recent applications in organic synthesis
journal, December 2013

Oligomerization of Ethylene Catalyzed by Iron and Cobalt in Organoaluminate Dialkylimidazolium Ionic Liquids
journal, May 2010

An experimental flow reactor study of the combustion kinetics of terpenoid jet fuel compounds: Farnesane, p-menthane and p-cymene
journal, January 2017

Chemical Routes for the Transformation of Biomass into Chemicals
journal, June 2007

Conversion of furfural into cyclopentanone over Ni–Cu bimetallic catalysts
journal, January 2013

Aqueous-biphasic hydroformylation of alkenes promoted by “weak” surfactants
journal, January 2009

Dissociation constant of aqueous trifluoroacetic acid by cryoscopy and conductivity
journal, July 1981

High-energy fuels and materials from plants
journal, April 1987

Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes
journal, May 2011

Pd/NbOPO ₄ Multifunctional Catalyst for the Direct Production of Liquid Alkanes from Aldol Adducts of Furans
journal, July 2014

Biphasic Suzuki coupling reactions of aryl or benzyl bromides employing cobalt-containing phosphine ligand coordinated palladium complex
journal, April 2005

Oligomerisation of isobutene with silica supported ionic liquid catalysts
journal, January 2012

Gas solubilities (hydrogen, helium, nitrogen, carbon monoxide, oxygen, argon, carbon dioxide) in organic liquids at 293.2 K
journal, April 1989

Industrial Aqueous Biphasic Catalysis: Status and Directions
journal, March 1998

Catalytic conversion of hemicellulosic biomass to lactic acid in pH neutral aqueous phase media
journal, January 2015

Bio-jet fuel conversion technologies
journal, January 2016

Integrated Catalytic Process for Biomass Conversion and Upgrading to C ₁₂ Furoin and Alkane Fuel
journal, March 2014

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

Optimizing carbon efficiency of jet fuel range alkanes from cellulose co-fed with polyethylene via catalytically combined processes
journal, August 2016

Low-temperature, solvent-free dehydration of cineoles with heterogeneous acid catalysts for the production of high-density biofuels: Low-temperature, solvent-free dehydration of cineoles
journal, April 2014

Scale of biomass production from new woody crops for salinity control in dryland agriculture in Australia
journal, January 2007

Catalytic hydrothermal deoxygenation of palmitic acid
journal, January 2010

Synthesis of Jet-Fuel Range Cycloalkanes from the Mixtures of Cyclopentanone and Butanal
journal, November 2015

Synthesis of 2,5-Hexanedione from Biomass Resources Using a Highly Efficient Biphasic System
journal, May 2016

High-Density Renewable Fuels Based on the Selective Dimerization of Pinenes
journal, January 2010

Synthesis of renewable jet and diesel fuels from 2-ethyl-1-hexene
journal, January 2010

Synthesis of renewable diesel with the 2-methylfuran, butanal and acetone derived from lignocellulose
journal, April 2013

The conversion of 1,8-cineole sourced from renewable Eucalyptus oil to p-cymene over a palladium doped γ-Al2O3 catalyst
journal, December 2011