Catalytic One‐Pot Conversion of Renewable Platform Chemicals to Hydrocarbon and Ether Biofuels through Tandem Hf(OTf) 4 +Pd/C Catalysis
Abstract
Abstract Efficient conversion of renewable biomass platform chemicals into high‐quality fuels remains challenging. A one‐pot catalytic approach has been developed to synthesize various structurally defined biofuels by using Hf(OTf) 4 and Pd/C for selective tandem catalysis and 2‐methylfuran (2‐MF) as a renewable feedstock. 2‐MF first undergoes Lewis acid‐catalyzed hydroxyalkylation/alkylation (HAA) condensation with carbonyl compounds to afford intermediates containing the targeted carbon skeletons of hydrocarbon or ether products, and these intermediates then undergo hydrogenation or hydrodeoxygenation to afford the target products, catalyzed by metal triflate+Pd/C in the same pot. The present process can produce structurally defined alkanes and cyclic ethers under mild conditions.
- Authors:
-
- School of Physical Science and Technology ShanghaiTech University 393 Middle Huaxia Road, Pudong District Shanghai 201210 China, University of Chinese Academy of Sciences Beijing 100049 China
- Department of Chemistry Northwestern University 2145 Sheridan Road Evanston IL, 60208 USA
- School of Physical Science and Technology ShanghaiTech University 393 Middle Huaxia Road, Pudong District Shanghai 201210 China
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1570034
- Grant/Contract Number:
- AC0206CH11357
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- ChemSusChem
- Additional Journal Information:
- Journal Name: ChemSusChem Journal Volume: 12 Journal Issue: 24; Journal ID: ISSN 1864-5631
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Liu, Dong‐Huang, Marks, Tobin J., and Li, Zhi. Catalytic One‐Pot Conversion of Renewable Platform Chemicals to Hydrocarbon and Ether Biofuels through Tandem Hf(OTf) 4 +Pd/C Catalysis. Germany: N. p., 2019.
Web. doi:10.1002/cssc.201902137.
Liu, Dong‐Huang, Marks, Tobin J., & Li, Zhi. Catalytic One‐Pot Conversion of Renewable Platform Chemicals to Hydrocarbon and Ether Biofuels through Tandem Hf(OTf) 4 +Pd/C Catalysis. Germany. https://doi.org/10.1002/cssc.201902137
Liu, Dong‐Huang, Marks, Tobin J., and Li, Zhi. Thu .
"Catalytic One‐Pot Conversion of Renewable Platform Chemicals to Hydrocarbon and Ether Biofuels through Tandem Hf(OTf) 4 +Pd/C Catalysis". Germany. https://doi.org/10.1002/cssc.201902137.
@article{osti_1570034,
title = {Catalytic One‐Pot Conversion of Renewable Platform Chemicals to Hydrocarbon and Ether Biofuels through Tandem Hf(OTf) 4 +Pd/C Catalysis},
author = {Liu, Dong‐Huang and Marks, Tobin J. and Li, Zhi},
abstractNote = {Abstract Efficient conversion of renewable biomass platform chemicals into high‐quality fuels remains challenging. A one‐pot catalytic approach has been developed to synthesize various structurally defined biofuels by using Hf(OTf) 4 and Pd/C for selective tandem catalysis and 2‐methylfuran (2‐MF) as a renewable feedstock. 2‐MF first undergoes Lewis acid‐catalyzed hydroxyalkylation/alkylation (HAA) condensation with carbonyl compounds to afford intermediates containing the targeted carbon skeletons of hydrocarbon or ether products, and these intermediates then undergo hydrogenation or hydrodeoxygenation to afford the target products, catalyzed by metal triflate+Pd/C in the same pot. The present process can produce structurally defined alkanes and cyclic ethers under mild conditions.},
doi = {10.1002/cssc.201902137},
journal = {ChemSusChem},
number = 24,
volume = 12,
place = {Germany},
year = {Thu Oct 10 00:00:00 EDT 2019},
month = {Thu Oct 10 00:00:00 EDT 2019}
}
https://doi.org/10.1002/cssc.201902137
Web of Science
Works referenced in this record:
Synthetic Strategies of Marine Polycyclic Ethers via Intramolecular Allylations: Linear and Convergent Approaches
journal, May 2005
- Kadota, Isao; Yamamoto, Yoshinori
- Accounts of Chemical Research, Vol. 38, Issue 5
An integrated strategy for catalytic co-production of jet fuel range alkenes, tetrahydrofurfuryl alcohol, and 1,2-pentanediol from lignocellulosic biomass
journal, January 2017
- Byun, Jaewon; Han, Jeehoon
- Green Chem., Vol. 19, Issue 21
CO 2 -Catalysed aldol condensation of 5-hydroxymethylfurfural and acetone to a jet fuel precursor
journal, January 2016
- Lee, Roland; Vanderveen, Jesse R.; Champagne, Pascale
- Green Chemistry, Vol. 18, Issue 19
Synthesis of Diesel and Jet Fuel Range Alkanes with Furfural and Angelica Lactone
journal, August 2017
- Xu, Jilei; Li, Ning; Yang, Xiaofeng
- ACS Catalysis, Vol. 7, Issue 9
Conversion of Fructose and Xylose into Platform Chemicals Using Organo-Functionalized Mesoporous Material
journal, October 2018
- Kalita, Pranjal; Datta, Prantu; Baruah, Pranjal K.
- ChemistrySelect, Vol. 3, Issue 39
High-Quality Diesel from Hexose- and Pentose-Derived Biomass Platform Molecules
journal, October 2011
- Corma, Avelino; de la Torre, Olalla; Renz, Michael
- ChemSusChem, Vol. 4, Issue 11
Cu (OTf)<SUB>2</SUB> catalysed reactions of furan and thiophene with α,β-unsaturated ketones
journal, May 2000
- Bulbule, Vivek J.; Deshpande, Vishnu H.; Bedekar, Ashutosh V.
- Journal of Chemical Research, Vol. 2000, Issue 5
Alkanes from Bioderived Furans by using Metal Triflates and Palladium-Catalyzed Hydrodeoxygenation of Cyclic Ethers
journal, November 2015
- Song, Hai-Jie; Deng, Jin; Cui, Min-Shu
- ChemSusChem, Vol. 8, Issue 24
Highly selective rearrangement of furfuryl alcohol to cyclopentanone
journal, July 2014
- Hronec, Milan; Fulajtárova, Katarína; Soták, Tomáš
- Applied Catalysis B: Environmental, Vol. 154-155
Simple Chemical Transformation of Lignocellulosic Biomass into Furans for Fuels and Chemicals
journal, February 2009
- Binder, Joseph B.; Raines, Ronald T.
- Journal of the American Chemical Society, Vol. 131, Issue 5, p. 1979-1985
Production of High-Quality Diesel from Biomass Waste Products
journal, January 2011
- Corma, Avelino; de la Torre, Olalla; Renz, Michael
- Angewandte Chemie International Edition, Vol. 50, Issue 10
Rapid Ether and Alcohol C–O Bond Hydrogenolysis Catalyzed by Tandem High-Valent Metal Triflate + Supported Pd Catalysts
journal, December 2013
- Li, Zhi; Assary, Rajeev S.; Atesin, Abdurrahman C.
- Journal of the American Chemical Society, Vol. 136, Issue 1
Catalytic Transformation of Lignin for the Production of Chemicals and Fuels
journal, October 2015
- Li, Changzhi; Zhao, Xiaochen; Wang, Aiqin
- Chemical Reviews, Vol. 115, Issue 21, p. 11559-11624
Lignosulfonate-based acidic resin for the synthesis of renewable diesel and jet fuel range alkanes with 2-methylfuran and furfural
journal, January 2015
- Li, Shanshan; Li, Ning; Li, Guangyi
- Green Chemistry, Vol. 17, Issue 6
Microbial Engineering for Aldehyde Synthesis
journal, January 2015
- Kunjapur, Aditya M.; Prather, Kristala L. J.
- Applied and Environmental Microbiology, Vol. 81, Issue 6
Conversion of biomass to selected chemical products
journal, January 2012
- Gallezot, Pierre
- Chem. Soc. Rev., Vol. 41, Issue 4
The hydrodeoxygenation of bioderived furans into alkanes
journal, April 2013
- Sutton, Andrew D.; Waldie, Fraser D.; Wu, Ruilian
- Nature Chemistry, Vol. 5, Issue 5, p. 428-432
Hydroisomerization, hydrocracking and dehydrocyclization of n-pentane and n-hexane using mono- and bimetallic catalysts promoted with fluorine
journal, July 2001
- Ali, Abdel-Ghaffar A.; Ali, Laila I.; Aboul-Fotouh, Sameh M.
- Applied Catalysis A: General, Vol. 215, Issue 1-2
Thermodynamic Strategies for C–O Bond Formation and Cleavage via Tandem Catalysis
journal, April 2016
- Lohr, Tracy L.; Li, Zhi; Marks, Tobin J.
- Accounts of Chemical Research, Vol. 49, Issue 5
Synthesis of High-Quality Diesel with Furfural and 2-Methylfuran from Hemicellulose
journal, August 2012
- Li, Guangyi; Li, Ning; Wang, Zhiqiang
- ChemSusChem, Vol. 5, Issue 10
Dehydroisomerization of n-Butane over Pt–ZSM5 (I): Effect of the Metal Loading and Acid Site Concentration
journal, August 1999
- Pirngruber, G. D.; Seshan, K.; Lercher, J. A.
- Journal of Catalysis, Vol. 186, Issue 1
Hydroisomerization and hydrocracking. 2. Product distributions from n-decane and n-dodecane
journal, December 1981
- Steijns, Matt; Froment, Gilbert; Jacobs, Peter
- Industrial & Engineering Chemistry Product Research and Development, Vol. 20, Issue 4
Catalytic Conversion of Carbohydrates to Initial Platform Chemicals: Chemistry and Sustainability
journal, November 2017
- Mika, László T.; Cséfalvay, Edit; Németh, Áron
- Chemical Reviews, Vol. 118, Issue 2
Polymer electrolytes for lithium polymer batteries
journal, January 2016
- Long, Lizhen; Wang, Shuanjin; Xiao, Min
- Journal of Materials Chemistry A, Vol. 4, Issue 26
Integration of chemical catalysis with extractive fermentation to produce fuels
journal, November 2012
- Anbarasan, Pazhamalai; Baer, Zachary C.; Sreekumar, Sanil
- Nature, Vol. 491, Issue 7423, p. 235-239
Oxidative Decarboxylation of Levulinic Acid by Cupric Oxides
journal, November 2010
- Gong, Yan; Lin, Lu; Shi, Jianbin
- Molecules, Vol. 15, Issue 11
Pd/NbOPO 4 Multifunctional Catalyst for the Direct Production of Liquid Alkanes from Aldol Adducts of Furans
journal, July 2014
- Xia, Qi-Neng; Cuan, Qian; Liu, Xiao-Hui
- Angewandte Chemie, Vol. 126, Issue 37
Production of High-Quality Diesel from Biomass Waste Products
journal, January 2011
- Corma, Avelino; de la Torre, Olalla; Renz, Michael
- Angewandte Chemie, Vol. 123, Issue 10
Solvent-Free Synthesis of C 10 and C 11 Branched Alkanes from Furfural and Methyl Isobutyl Ketone
journal, June 2013
- Yang, Jinfan; Li, Ning; Li, Guangyi
- ChemSusChem, Vol. 6, Issue 7
Catalytic conversion of biomass to biofuels
journal, January 2010
- Alonso, David Martin; Bond, Jesse Q.; Dumesic, James A.
- Green Chemistry, Vol. 12, Issue 9, p. 1493-1513
Production of high quality diesel from cellulose and hemicellulose by the Sylvan process: catalysts and process variables
journal, January 2012
- Corma, Avelino; de la Torre, Olalla; Renz, Michael
- Energy & Environmental Science, Vol. 5, Issue 4
Metal/Acid Bifunctional Catalysis and Intimacy Criterion for Ethylcyclohexane Hydroconversion: When Proximity Does Not Matter
journal, May 2018
- Gutierrez-Acebo, Ester; Leroux, Charles; Chizallet, Céline
- ACS Catalysis, Vol. 8, Issue 7
Selective One-Pot Production of High-Grade Diesel-Range Alkanes from Furfural and 2-Methylfuran over Pd/NbOPO 4
journal, November 2016
- Xia, Qineng; Xia, Yinjiang; Xi, Jinxu
- ChemSusChem, Vol. 10, Issue 4
Diesel and Alkane Fuels From Biomass by Organocatalysis and Metal-Acid Tandem Catalysis
journal, August 2013
- Liu, Dajiang; Chen, Eugene Y. -X.
- ChemSusChem, Vol. 6, Issue 12
Synthesis of ketones from biomass-derived feedstock
journal, January 2017
- Meng, Qinglei; Hou, Minqiang; Liu, Huizhen
- Nature Communications, Vol. 8, Issue 1
Pot economy and one-pot synthesis
journal, January 2016
- Hayashi, Yujiro
- Chemical Science, Vol. 7, Issue 2
High Ion Conducting Solid Composite Electrolytes with Enhanced Interfacial Compatibility for Lithium Metal Batteries
journal, February 2019
- Feng, Haoyu; Ma, Cheng; Dai, Kuan
- ChemElectroChem, Vol. 6, Issue 3
Efficient and selective hydrogenation of biomass-derived furfural to cyclopentanone using Ru catalysts
journal, January 2015
- Fang, Ruiqi; Liu, Hongli; Luque, Rafael
- Green Chemistry, Vol. 17, Issue 8
Die Lithium-Sauerstoff-Batterie mit etherbasierten Elektrolyten
journal, July 2011
- Freunberger, Stefan A.; Chen, Yuhui; Drewett, Nicholas E.
- Angewandte Chemie, Vol. 123, Issue 37
Advanced Biofuels and Beyond: Chemistry Solutions for Propulsion and Production
journal, April 2017
- Leitner, Walter; Klankermayer, Jürgen; Pischinger, Stefan
- Angewandte Chemie International Edition, Vol. 56, Issue 20
Interfacial Chemistry Regulation via a Skin-Grafting Strategy Enables High-Performance Lithium-Metal Batteries
journal, October 2017
- Gao, Yue; Zhao, Yuming; Li, Yuguang C.
- Journal of the American Chemical Society, Vol. 139, Issue 43
An overview of biorefinery-derived platform chemicals from a cellulose and hemicellulose biorefinery
journal, July 2018
- Takkellapati, Sudhakar; Li, Tao; Gonzalez, Michael A.
- Clean Technologies and Environmental Policy, Vol. 20, Issue 7
Conversion of levulinic acid to 2-butanone by acetoacetate decarboxylase from Clostridium acetobutylicum
journal, April 2013
- Min, Kyoungseon; Kim, Seil; Yum, Taewoo
- Applied Microbiology and Biotechnology, Vol. 97, Issue 12
Catalytic Tandem Reaction for the Production of Jet and Diesel Fuel Range Alkanes
journal, April 2018
- Li, Hu; Gui, Zhenyou; Yang, Song
- Energy Technology, Vol. 6, Issue 6
The Conversion of Starch and Sugars into Branched C 10 and C 11 Hydrocarbons
journal, July 2016
- Sutton, Andrew D.; Kim, Jin K.; Wu, Ruilian
- ChemSusChem, Vol. 9, Issue 17
Contribution of Different NbOx Species in the Hydrodeoxygenation of 2,5-Dimethyltetrahydrofuran to Hexane
journal, August 2018
- Xue, Fei; Ma, Di; Tong, Tao
- ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 10
Structure of the polymer electrolyte poly(ethylene oxide)6:LiAsF6
journal, April 1999
- MacGlashan, Graham S.; Andreev, Yuri G.; Bruce, Peter G.
- Nature, Vol. 398, Issue 6730
Pd/NbOPO 4 Multifunctional Catalyst for the Direct Production of Liquid Alkanes from Aldol Adducts of Furans
journal, July 2014
- Xia, Qi-Neng; Cuan, Qian; Liu, Xiao-Hui
- Angewandte Chemie International Edition, Vol. 53, Issue 37
Challenges in the development of advanced Li-ion batteries: a review
journal, January 2011
- Etacheri, Vinodkumar; Marom, Rotem; Elazari, Ran
- Energy & Environmental Science, Vol. 4, Issue 9
Selective Conversion of Furfural to Cyclopentanone with CuZnAl Catalysts
journal, September 2014
- Guo, Jianhua; Xu, Guangyue; Han, Zheng
- ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 10
Production of Fuels and Chemicals from Biomass: Condensation Reactions and Beyond
journal, July 2016
- Wu, Lipeng; Moteki, Takahiko; Gokhale, Amit A.
- Chem, Vol. 1, Issue 1
Catalytic Upgrading of 5-Hydroxymethylfurfural to Drop-in Biofuels by Solid Base and Bifunctional Metal-Acid Catalysts
journal, November 2015
- Bohre, Ashish; Saha, Basudeb; Abu-Omar, Mahdi M.
- ChemSusChem, Vol. 8, Issue 23
Hydroisomerization and hydrocracking of n-alkanes. 1. Ideal hydroisomerization PtHY catalysts
journal, September 1986
- Giannetto, Giuseppe E.; Perot, Guy R.; Guisnet, Michel R.
- Industrial & Engineering Chemistry Product Research and Development, Vol. 25, Issue 3
Highly Selective and Efficient Rearrangement of Biomass-Derived Furfural to Cyclopentanone over Interface-Active Ru/Carbon Nanotubes Catalyst in Water
journal, November 2016
- Liu, Yanhua; Chen, Zhihao; Wang, Xiaofeng
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 1
The roles of Lewis acidic additives in organotransition metal catalysis
journal, January 2019
- Becica, Joseph; Dobereiner, Graham E.
- Organic & Biomolecular Chemistry, Vol. 17, Issue 8
Tailor-Made Fuels from Biomass for Homogeneous Low-Temperature Diesel Combustion
journal, October 2011
- Janssen, Andreas J.; Kremer, Florian W.; Baron, Jan H.
- Energy & Fuels, Vol. 25, Issue 10
Screening Pathways for the Production of Next Generation Biofuels
journal, December 2015
- Ulonska, Kirsten; Voll, Anna; Marquardt, Wolfgang
- Energy & Fuels, Vol. 30, Issue 1
Hydroisomerization and Hydrocracking of Alkanes
journal, September 1996
- Alvarez, F.; Ribeiro, F. R.; Perot, G.
- Journal of Catalysis, Vol. 162, Issue 2
Carbon-Increasing Catalytic Strategies for Upgrading Biomass into Energy-Intensive Fuels and Chemicals
journal, December 2017
- Li, Hu; Riisager, Anders; Saravanamurugan, Shunmugavel
- ACS Catalysis, Vol. 8, Issue 1
Novel Strategies for the Production of Fuels, Lubricants, and Chemicals from Biomass
journal, September 2017
- Shylesh, Sankaranarayanapillai; Gokhale, Amit A.; Ho, Christopher R.
- Accounts of Chemical Research, Vol. 50, Issue 10
Synthese, motorische Verbrennung, Emissionen: Chemische Aspekte des Kraftstoffdesigns
journal, April 2017
- Leitner, Walter; Klankermayer, Jürgen; Pischinger, Stefan
- Angewandte Chemie, Vol. 129, Issue 20
Catalytic Hydrocracking-Mechanisms and Versatility of the Process
journal, February 2012
- Weitkamp, Jens
- ChemCatChem, Vol. 4, Issue 3
Recent advances in catalytic transformation of biomass-derived 5-hydroxymethylfurfural into the innovative fuels and chemicals
journal, July 2017
- Hu, Lei; Lin, Lu; Wu, Zhen
- Renewable and Sustainable Energy Reviews, Vol. 74
Expanding the biomass derived chemical space
journal, January 2017
- Brun, Nicolas; Hesemann, Peter; Esposito, Davide
- Chemical Science, Vol. 8, Issue 7
Upgrading Furfurals to Drop-in Biofuels: An Overview
journal, June 2015
- Bohre, Ashish; Dutta, Saikat; Saha, Basudeb
- ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 7
Hydrodeoxygenation of Furylmethane Oxygenates to Jet and Diesel Range Fuels: Probing the Reaction Network with Supported Palladium Catalyst and Hafnium Triflate Promoter
journal, July 2017
- Dutta, Saikat; Saha, Basudeb
- ACS Catalysis, Vol. 7, Issue 8
Cu(OTf)2 Catalyzed Synthesis of Bis(5-methyl-2-furyl)methanes by Condensation of 2-Methylfuran with Carbonyl Compounds under Solvent Free Conditions
journal, July 2011
- Muthyala, Manoj Kumar; Rao, V. Kameswara; Kumar, Anil
- Chinese Journal of Chemistry, Vol. 29, Issue 7
One-step production of long-chain hydrocarbons from waste-biomass-derived chemicals using bi-functional heterogeneous catalysts
journal, January 2014
- Wen, Cun; Barrow, Elizabeth; Hattrick-Simpers, Jason
- Physical Chemistry Chemical Physics, Vol. 16, Issue 7
One-step Pd/C and Eu(OTf) 3 catalyzed hydrodeoxygenation of branched C 11 and C 12 biomass-based furans to the corresponding alkanes
journal, March 2017
- Keskiväli, Juha; Wrigstedt, Pauli; Lagerblom, Kalle
- Applied Catalysis A: General, Vol. 534
Potential of oxymethylenether-diesel blends for ultra-low emission engines
journal, December 2017
- Omari, Ahmad; Heuser, Benedikt; Pischinger, Stefan
- Fuel, Vol. 209
The Lithium-Oxygen Battery with Ether-Based Electrolytes
journal, July 2011
- Freunberger, Stefan A.; Chen, Yuhui; Drewett, Nicholas E.
- Angewandte Chemie International Edition, Vol. 50, Issue 37, p. 8609-8613
Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines
journal, January 2016
- Cabrero-Antonino, Jose R.; Alberico, Elisabetta; Junge, Kathrin
- Chemical Science, Vol. 7, Issue 5
Selective Hydrogenation of Furan-Containing Condensation Products as a Source of Biomass-Derived Diesel Additives
journal, August 2014
- Balakrishnan, Madhesan; Sacia, Eric R.; Bell, Alexis T.
- ChemSusChem, Vol. 7, Issue 10
Tetrahydrofuran-Containing Macrolides: A Fascinating Gift from the Deep Sea
journal, March 2013
- Lorente, Adriana; Lamariano-Merketegi, Janire; Albericio, Fernando
- Chemical Reviews, Vol. 113, Issue 7
Selective conversion of furfural to cyclopentanol over cobalt catalysts in one step
journal, June 2017
- Ma, Yan-Fu; Wang, Hao; Xu, Guang-Yue
- Chinese Chemical Letters, Vol. 28, Issue 6
Conversion of Biomass into Chemicals over Metal Catalysts
journal, October 2013
- Besson, Michèle; Gallezot, Pierre; Pinel, Catherine
- Chemical Reviews, Vol. 114, Issue 3