Direct carbon-carbon coupling of furanics with acetic acid over Bronsted zeolites

Gumidyala, Abhishek; Wang, Bin; Crossley, Steven

doi:10.1126/sciadv.1601072

Title: Direct carbon-carbon coupling of furanics with acetic acid over Bronsted zeolites

Journal Article · Fri Sep 16 00:00:00 EDT 2016 · Science Advances

DOI: https://doi.org/10.1126/sciadv.1601072 · OSTI ID:1437643

Gumidyala, Abhishek ^[1]; Wang, Bin ^[2]; Crossley, Steven ^[2]

Univ. of Oklahoma, Norman, OK (United States). School of Chemical, Biological and Materials Engineering; University of Oklahoma
Univ. of Oklahoma, Norman, OK (United States). School of Chemical, Biological and Materials Engineering

Effective carbon-carbon coupling of acetic acid to form larger products while minimizing CO₂ emissions is critical to achieving a step change in efficiency for the production of transportation fuels from sustainable biomass. Here, we report the direct acylation of methylfuran with acetic acid in the presence ofwater, all ofwhich can be readily produced from biomass. This direct coupling limits unwanted polymerization of furanics while producing acetyl methylfuran. Reaction kinetics and density functional theory calculations illustrate that the calculated apparent barrier for the dehydration of the acid to form surface acyl species is similar to the experimentally measured barrier, implying that this step plays a significant role in determining the net reaction rate. Water inhibits the overall rate, but selectivity to acylated products is not affected.We show that furanic species effectively stabilize the charge of the transition state, therefore lowering the overall activation barrier. These results demonstrate a promising new route to C–C bond–forming reactions for the production of higher-value products from biomass.

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Research Organization:: Univ. of Oklahoma, Norman, OK (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: EE0006287; SC0004600

OSTI ID:: 1437643

Journal Information:: Science Advances, Journal Name: Science Advances Journal Issue: 9 Vol. 2; ISSN 2375-2548

Publisher:: AAASCopyright Statement

Country of Publication:: United States

Language:: English

References (60)

Decoupling HZSM-5 Catalyst Activity from Deactivation during Upgrading of Pyrolysis Oil Vapors Wan, Shaolong; Waters, Christopher; Stevens, Adam ChemSusChem, Vol. 8, Issue 3 https://doi.org/10.1002/cssc.201402861	journal	December 2014
One-step hydrogenation–esterification of furfural and acetic acid over bifunctional Pd catalysts for bio-oil upgrading Yu, Wanjin; Tang, Yang; Mo, Liuye Bioresource Technology, Vol. 102, Issue 17 https://doi.org/10.1016/j.biortech.2011.06.015	journal	September 2011
The effect of torrefaction on the chemistry of fast-pyrolysis bio-oil Meng, Jiajia; Park, Junyeong; Tilotta, David Bioresource Technology, Vol. 111 https://doi.org/10.1016/j.biortech.2012.01.159	journal	May 2012
Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid Padro, C. Journal of Catalysis, Vol. 226, Issue 2 https://doi.org/10.1016/j.jcat.2004.05.030	journal	September 2004
Selective ketonization of acetic acid over HZSM-5: The importance of acyl species and the influence of water Gumidyala, Abhishek; Sooknoi, Tawan; Crossley, Steven Journal of Catalysis, Vol. 340 https://doi.org/10.1016/j.jcat.2016.04.017	journal	August 2016
Update 1 of: Use of Solid Catalysts in Friedel−Crafts Acylation Reactions Sartori, Giovanni; Maggi, Raimondo Chemical Reviews, Vol. 111, Issue 5 https://doi.org/10.1021/cr100375z	journal	May 2011
Overview of Applications of Biomass Fast Pyrolysis Oil Czernik, S.; Bridgwater, A. V. Energy & Fuels, Vol. 18, Issue 2, p. 590-598 https://doi.org/10.1021/ef034067u	journal	March 2004
Acidity of Biomass Fast Pyrolysis Bio-oils Oasmaa, Anja; Elliott, Douglas C.; Korhonen, Jaana Energy & Fuels, Vol. 24, Issue 12 https://doi.org/10.1021/ef100935r	journal	December 2010
Degree of Rate Control: How Much the Energies of Intermediates and Transition States Control Rates Stegelmann, Carsten; Andreasen, Anders; Campbell, Charles T. Journal of the American Chemical Society, Vol. 131, Issue 37 https://doi.org/10.1021/ja9065199	journal	September 2009
Catalytic conversion of lignocellulosic biomass to fine chemicals and fuels Zhou, Chun-Hui; Xia, Xi; Lin, Chun-Xiang Chemical Society Reviews, Vol. 40, Issue 11 https://doi.org/10.1039/c1cs15124j	journal	January 2011
Conversion of biomass to selected chemical products Gallezot, Pierre Chem. Soc. Rev., Vol. 41, Issue 4 https://doi.org/10.1039/c1cs15147a	journal	January 2012
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/physrevlett.77.3865	journal	October 1996
Insights into Current Limitations of Density Functional Theory Cohen, A. J.; Mori-Sanchez, P.; Yang, W. Science, Vol. 321, Issue 5890 https://doi.org/10.1126/science.1158722	journal	August 2008
CC Coupling for Biomass-Derived Furanics Upgrading to Chemicals and Fuels Bui, Tuong V.; Crossley, Steven; Resasco, Daniel E. Chemicals and Fuels from Bio‐Based Building Blocks https://doi.org/10.1002/9783527698202.ch17	book	February 2016
Biofuels and Biomass-To-Liquid Fuels in the Biorefinery: Catalytic Conversion of Lignocellulosic Biomass using Porous Materials Stöcker, Michael Angewandte Chemie International Edition, Vol. 47, Issue 48 https://doi.org/10.1002/anie.200801476	journal	October 2008
Lignocellulose conversion: an introduction to chemistry, process and economics Lange, Jean-Paul Biofuels, Bioproducts and Biorefining, Vol. 1, Issue 1, p. 39-48 https://doi.org/10.1002/bbb.7	journal	January 2007
Green Gasoline by Catalytic Fast Pyrolysis of Solid Biomass Derived Compounds Carlson, Torren R.; Vispute, Tushar P.; Huber, George W. ChemSusChem, Vol. 1, Issue 5 https://doi.org/10.1002/cssc.200800018	journal	May 2008
Decoupling HZSM-5 Catalyst Activity from Deactivation during Upgrading of Pyrolysis Oil Vapors Wan, Shaolong; Waters, Christopher; Stevens, Adam ChemSusChem, Vol. 8, Issue 3 https://doi.org/10.1002/cssc.201402861	journal	December 2014
Mild hydrotreating of biomass pyrolysis oils to produce a suitable refinery feedstock French, Richard J.; Hrdlicka, Jason; Baldwin, Robert Environmental Progress & Sustainable Energy, Vol. 29, Issue 2 https://doi.org/10.1002/ep.10419	journal	February 2010
Effect of the damping function in dispersion corrected density functional theory Grimme, Stefan; Ehrlich, Stephan; Goerigk, Lars Journal of Computational Chemistry, Vol. 32, Issue 7 https://doi.org/10.1002/jcc.21759	journal	March 2011
Reactions of Carboxylic Acids on Oxides Pestman, R.; Koster, R. M.; van Duijne, A. Journal of Catalysis, Vol. 168, Issue 2 https://doi.org/10.1006/jcat.1997.1624	journal	June 1997
Zeolite-Induced Selectivity in the Conversion of the Lower Aliphatic Carboxylic Acids Vervecken, M.; Servotte, Y.; Wydoodt, M. Chemical Reactions in Organic and Inorganic Constrained Systems https://doi.org/10.1007/978-94-009-4582-1_8	book	January 1986
Phenol alkylation with methanol: effect of sodium content and ammonia selective poisoning of an HY zeolite Garc�a, L.; Giannetto, G.; Goldwasser, M. R. Catalysis Letters, Vol. 37, Issue 1-2 https://doi.org/10.1007/BF00813529	journal	January 1996
Hydrodeoxygenation of Furfural Over Supported Metal Catalysts: A Comparative Study of Cu, Pd and Ni Sitthisa, Surapas; Resasco, Daniel E. Catalysis Letters, Vol. 141, Issue 6 https://doi.org/10.1007/s10562-011-0581-7	journal	March 2011
Fast pyrolysis processes for biomass Bridgwater, A. Renewable and Sustainable Energy Reviews, Vol. 4, Issue 1 https://doi.org/10.1016/S1364-0321(99)00007-6	journal	March 2000
One-step hydrogenation–esterification of furfural and acetic acid over bifunctional Pd catalysts for bio-oil upgrading Yu, Wanjin; Tang, Yang; Mo, Liuye Bioresource Technology, Vol. 102, Issue 17 https://doi.org/10.1016/j.biortech.2011.06.015	journal	September 2011
The effect of torrefaction on the chemistry of fast-pyrolysis bio-oil Meng, Jiajia; Park, Junyeong; Tilotta, David Bioresource Technology, Vol. 111 https://doi.org/10.1016/j.biortech.2012.01.159	journal	May 2012
Periodic, vdW-corrected density functional theory investigation of the effect of Al siting in H-ZSM-5 on chemisorption properties and site-specific acidity Ghorbanpour, Arian; Rimer, Jeffrey D.; Grabow, Lars C. Catalysis Communications, Vol. 52 https://doi.org/10.1016/j.catcom.2014.04.005	journal	July 2014
Implementation of concepts derived from model compound studies in the separation and conversion of bio-oil to fuel Resasco, Daniel E.; Crossley, Steven P. Catalysis Today, Vol. 257 https://doi.org/10.1016/j.cattod.2014.06.037	journal	November 2015
Review of biomass pyrolysis oil properties and upgrading research Zhang, Qi; Chang, Jie; Wang, Tiejun Energy Conversion and Management, Vol. 48, Issue 1, p. 87-92 https://doi.org/10.1016/j.enconman.2006.05.010	journal	January 2007
Torrefaction of wood Prins, Mark J.; Ptasinski, Krzysztof J.; Janssen, Frans J. J. G. Journal of Analytical and Applied Pyrolysis, Vol. 77, Issue 1 https://doi.org/10.1016/j.jaap.2006.01.001	journal	August 2006
Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid Padro, C. Journal of Catalysis, Vol. 226, Issue 2 https://doi.org/10.1016/j.jcat.2004.05.030	journal	September 2004
Selective conversion of furfural to methylfuran over silica-supported NiFe bimetallic catalysts Sitthisa, Surapas; An, Wei; Resasco, Daniel E. Journal of Catalysis, Vol. 284, Issue 1 https://doi.org/10.1016/j.jcat.2011.09.005	journal	November 2011
Aqueous-phase ketonization of acetic acid over Ru/TiO2/carbon catalysts Pham, Tu Nguyet; Shi, Dachuan; Sooknoi, Tawan Journal of Catalysis, Vol. 295 https://doi.org/10.1016/j.jcat.2012.08.012	journal	November 2012
Selective ketonization of acetic acid over HZSM-5: The importance of acyl species and the influence of water Gumidyala, Abhishek; Sooknoi, Tawan; Crossley, Steven Journal of Catalysis, Vol. 340 https://doi.org/10.1016/j.jcat.2016.04.017	journal	August 2016
Update 1 of: Use of Solid Catalysts in Friedel−Crafts Acylation Reactions Sartori, Giovanni; Maggi, Raimondo Chemical Reviews, Vol. 111, Issue 5 https://doi.org/10.1021/cr100375z	journal	May 2011
Chemistry of Furan Conversion into Aromatics and Olefins over HZSM-5: A Model Biomass Conversion Reaction Cheng, Yu-Ting; Huber, George W. ACS Catalysis, Vol. 1, Issue 6 https://doi.org/10.1021/cs200103j	journal	May 2011
Ketonization of Carboxylic Acids: Mechanisms, Catalysts, and Implications for Biomass Conversion Pham, Tu N.; Sooknoi, Tawan; Crossley, Steven P. ACS Catalysis, Vol. 3, Issue 11 https://doi.org/10.1021/cs400501h	journal	October 2013
Overview of Applications of Biomass Fast Pyrolysis Oil Czernik, S.; Bridgwater, A. V. Energy & Fuels, Vol. 18, Issue 2, p. 590-598 https://doi.org/10.1021/ef034067u	journal	March 2004
Acidity of Biomass Fast Pyrolysis Bio-oils Oasmaa, Anja; Elliott, Douglas C.; Korhonen, Jaana Energy & Fuels, Vol. 24, Issue 12 https://doi.org/10.1021/ef100935r	journal	December 2010
Catalytic Hydroprocessing of Chemical Models for Bio-oil Elliott, Douglas C.; Hart, Todd R. Energy & Fuels, Vol. 23, Issue 2, p. 631-637 https://doi.org/10.1021/ef8007773	journal	February 2009
Degree of Rate Control: How Much the Energies of Intermediates and Transition States Control Rates Stegelmann, Carsten; Andreasen, Anders; Campbell, Charles T. Journal of the American Chemical Society, Vol. 131, Issue 23 https://doi.org/10.1021/ja9000097	journal	June 2009
Vapour phase acylation of furan and pyrrole over zeolites Ram Reddy, P.; Subrahmanyam, M.; Kulkarni, S. J. Catalysis Letters, Vol. 54, Issue 1-2, p. 95-100 https://doi.org/10.1023/A:1019015619247	journal	August 1998
Conversion of biomass to selected chemical products Gallezot, Pierre Chem. Soc. Rev., Vol. 41, Issue 4 https://doi.org/10.1039/C1CS15147A	journal	January 2012
Zeolite-catalysed C–C bond forming reactions for biomass conversion to fuels and chemicals Resasco, Daniel E.; Wang, Bin; Crossley, Steven Catalysis Science & Technology, Vol. 6, Issue 8 https://doi.org/10.1039/C5CY02271A	journal	January 2016
Catalytic conversion of biomass to biofuels Alonso, David Martin; Bond, Jesse Q.; Dumesic, James A. Green Chemistry, Vol. 12, Issue 9, p. 1493-1513 https://doi.org/10.1039/c004654j	journal	January 2010
Catalytic conversion of lignocellulosic biomass to fine chemicals and fuels Zhou, Chun-Hui; Xia, Xi; Lin, Chun-Xiang Chemical Society Reviews, Vol. 40, Issue 11 https://doi.org/10.1039/c1cs15124j	journal	January 2011
Conversion of biomass to selected chemical products Gallezot, Pierre Chem. Soc. Rev., Vol. 41, Issue 4 https://doi.org/10.1039/c1cs15147a	journal	January 2012
A climbing image nudged elastic band method for finding saddle points and minimum energy paths Henkelman, Graeme; Uberuaga, Blas P.; Jónsson, Hannes The Journal of Chemical Physics, Vol. 113, Issue 22, p. 9901-9904 https://doi.org/10.1063/1.1329672	journal	December 2000
Hybrid functionals based on a screened Coulomb potential Heyd, Jochen; Scuseria, Gustavo E.; Ernzerhof, Matthias The Journal of Chemical Physics, Vol. 118, Issue 18 https://doi.org/10.1063/1.1564060	journal	May 2003
Erratum: “Hybrid functionals based on a screened Coulomb potential” [J. Chem. Phys. 118, 8207 (2003)] Heyd, Jochen; Scuseria, Gustavo E.; Ernzerhof, Matthias The Journal of Chemical Physics, Vol. 124, Issue 21 https://doi.org/10.1063/1.2204597	journal	June 2006
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Projector augmented-wave method Blöchl, P. E. Physical Review B, Vol. 50, Issue 24, p. 17953-17979 https://doi.org/10.1103/PhysRevB.50.17953	journal	December 1994
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
From ultrasoft pseudopotentials to the projector augmented-wave method Kresse, G.; Joubert, D. Physical Review B, Vol. 59, Issue 3, p. 1758-1775 https://doi.org/10.1103/PhysRevB.59.1758	journal	January 1999
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
High-temperature (350 K) orthorhombic framework structure of zeolite H-ZSM-5 van Koningsveld, H. Acta Crystallographica Section B Structural Science, Vol. 46, Issue 6 https://doi.org/10.1107/S0108768190007522	journal	December 1990
Insights into Current Limitations of Density Functional Theory Cohen, A. J.; Mori-Sanchez, P.; Yang, W. Science, Vol. 321, Issue 5890 https://doi.org/10.1126/science.1158722	journal	August 2008
Advances in Friedel-Crafts Acylation Reactions Sartori, Giovanni; Maggi, Raimondo CRC Press https://doi.org/10.1201/9781420067934	reference-book	January 2009

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Title: Direct carbon-carbon coupling of furanics with acetic acid over Bronsted zeolites

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