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Title: Bifunctional Catalysts for Upgrading of Biomass-Derived Oxygenates: A Review

Abstract

Deoxygenation is an important reaction in the conversion of biomass-derived oxygenates to fuels and chemicals. A key route for biomass refining involves the production of pyrolysis oil through rapid heating of the raw biomass feedstock. Pyrolysis oil as produced is highly oxygenated, so the feasibility of this approach depends in large part on the ability to selectively deoxygenate pyrolysis oil components to create a stream of high-value finished products. Identification of catalytic materials that are active and selective for deoxygenation of pyrolysis oil components has therefore represented a major research area. One catalyst is rarely capable of performing the different types of elementary reaction steps required to deoxygenate biomass-derived compounds. For this reason, considerable attention has been placed on bifunctional catalysts, where two different active materials are used to provide catalytic sites for diverse reaction steps. Here, we review recent trends in the development of catalysts, with a focus on catalysts for which a bifunctional effect has been proposed. We summarize recent studies of hydrodeoxygenation (HDO) of pyrolysis oil and model compounds for a range of materials, including supported metal and bimetallic catalysts as well as transition-metal oxides, sulfides, carbides, nitrides, and phosphides. Particular emphasis is placed on how catalystmore » structure can be related to performance via molecular-level mechanisms. Finally, these studies demonstrate the importance of catalyst bifunctionality, with each class of materials requiring hydrogenation and C-O scission sites to perform HDO at reasonable rates.« less

Authors:
 [1];  [2];  [1]
  1. Department of Chemical and Biological Engineering, University of Colorado—Boulder, UCB 596, Boulder, Colorado 80309, United States
  2. National Bioenergy Center, National Renewable Energy Laboratory, 15013 Denver West Pikeway, Golden, Colorado 80401, United States
Publication Date:
Research Org.:
National Renewable Energy Laboratory (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Sustainable Transportation. Bioenergy Technologies Office (BETO); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Sustainable Transportation Office. Bioenergy Technologies Office (BETO)
OSTI Identifier:
1326118
Alternate Identifier(s):
OSTI ID: 1313615
Report Number(s):
NREL/JA-5100-67033
Journal ID: ISSN 2155-5435
Grant/Contract Number:  
AC36-08-GO28308; AC36-08GO28308
Resource Type:
Published Article
Journal Name:
ACS Catalysis
Additional Journal Information:
Journal Name: ACS Catalysis Journal Volume: 6 Journal Issue: 8; Journal ID: ISSN 2155-5435
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; bifunctional; bimetallic; catalyst; hydrodeoxygenation; metal-metal oxide; tethered bifunctional catalysts

Citation Formats

Robinson, Allison M., Hensley, Jesse E., and Medlin, J. Will. Bifunctional Catalysts for Upgrading of Biomass-Derived Oxygenates: A Review. United States: N. p., 2016. Web. doi:10.1021/acscatal.6b00923.
Robinson, Allison M., Hensley, Jesse E., & Medlin, J. Will. Bifunctional Catalysts for Upgrading of Biomass-Derived Oxygenates: A Review. United States. https://doi.org/10.1021/acscatal.6b00923
Robinson, Allison M., Hensley, Jesse E., and Medlin, J. Will. Wed . "Bifunctional Catalysts for Upgrading of Biomass-Derived Oxygenates: A Review". United States. https://doi.org/10.1021/acscatal.6b00923.
@article{osti_1326118,
title = {Bifunctional Catalysts for Upgrading of Biomass-Derived Oxygenates: A Review},
author = {Robinson, Allison M. and Hensley, Jesse E. and Medlin, J. Will},
abstractNote = {Deoxygenation is an important reaction in the conversion of biomass-derived oxygenates to fuels and chemicals. A key route for biomass refining involves the production of pyrolysis oil through rapid heating of the raw biomass feedstock. Pyrolysis oil as produced is highly oxygenated, so the feasibility of this approach depends in large part on the ability to selectively deoxygenate pyrolysis oil components to create a stream of high-value finished products. Identification of catalytic materials that are active and selective for deoxygenation of pyrolysis oil components has therefore represented a major research area. One catalyst is rarely capable of performing the different types of elementary reaction steps required to deoxygenate biomass-derived compounds. For this reason, considerable attention has been placed on bifunctional catalysts, where two different active materials are used to provide catalytic sites for diverse reaction steps. Here, we review recent trends in the development of catalysts, with a focus on catalysts for which a bifunctional effect has been proposed. We summarize recent studies of hydrodeoxygenation (HDO) of pyrolysis oil and model compounds for a range of materials, including supported metal and bimetallic catalysts as well as transition-metal oxides, sulfides, carbides, nitrides, and phosphides. Particular emphasis is placed on how catalyst structure can be related to performance via molecular-level mechanisms. Finally, these studies demonstrate the importance of catalyst bifunctionality, with each class of materials requiring hydrogenation and C-O scission sites to perform HDO at reasonable rates.},
doi = {10.1021/acscatal.6b00923},
journal = {ACS Catalysis},
number = 8,
volume = 6,
place = {United States},
year = {2016},
month = {7}
}

Journal Article:
Free Publicly Available Full Text
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https://doi.org/10.1021/acscatal.6b00923

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  • Bui, Van Ngoc; Laurenti, Dorothée; Afanasiev, Pavel
  • Applied Catalysis B: Environmental, Vol. 101, Issue 3-4, p. 239-245
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Mono and Bifunctional Pathways of CO2/CH4Reforming over Pt and Rh Based Catalysts
journal, May 1998

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  • Journal of Catalysis, Vol. 176, Issue 1
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Hydrodeoxygenation of guaiacol over carbon-supported molybdenum nitride catalysts: Effects of nitriding methods and support properties
journal, October 2012


Size-Specific Chemistry on Bimetallic Surfaces: A Combined Experimental and Theoretical Study
journal, October 2007


Novel, uniform nanostructured catalytic membranes
journal, October 2006


Hydrogenolysis of 1,2-Propanediol for the Production of Biopropanols from Glycerol
journal, May 2010


Bifunctional nature of a SiO2-supported Ni2P catalyst for hydrotreating: EXAFS and FTIR studies
journal, April 2006


Condensation reactions of propanal over CexZr1−xO2 mixed oxide catalysts
journal, September 2010


Break-Up of Stepped Platinum Catalyst Surfaces by High CO Coverage
journal, February 2010


Bio-oils Hydrodeoxygenation: Adsorption of Phenolic Molecules on Oxidic Catalyst Supports
journal, August 2010

  • Popov, Andrey; Kondratieva, Elena; Goupil, Jean Michel
  • The Journal of Physical Chemistry C, Vol. 114, Issue 37
  • DOI: 10.1021/jp101949j

Reforming of Oxygenates for H 2 Production:  Correlating Reactivity of Ethylene Glycol and Ethanol on Pt(111) and Ni/Pt(111) with Surface d-Band Center
journal, February 2006

  • Skoplyak, Orest; Barteau, Mark A.; Chen, Jingguang G.
  • The Journal of Physical Chemistry B, Vol. 110, Issue 4
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Solid acid co-catalyst for the hydrogenolysis of glycerol to 1,3-propanediol over Ir-ReOx/SiO2
journal, August 2012


Comparison of H2 production from ethanol and ethylene glycol on M/Pt(111) (M=Ni, Fe, Ti) bimetallic surfaces
journal, September 2009


Coating Fine Nickel Particles with Al 2 O 3 Utilizing an Atomic Layer Deposition-Fluidized Bed Reactor (ALD-FBR)
journal, April 2004


A review of catalytic hydrodeoxygenation of lignin-derived phenols from biomass pyrolysis
journal, November 2012


Effect of nickel on the surface acidity of γ-alumina and alumina-supported nickel—molybdenum hydrotreating catalysts
journal, May 1989


Trapping Guests within a Nanoporous Metal–Organic Framework through Pressure-Induced Amorphization
journal, November 2011

  • Chapman, Karena W.; Sava, Dorina F.; Halder, Gregory J.
  • Journal of the American Chemical Society, Vol. 133, Issue 46
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Alkali-Stabilized Pt-OHx Species Catalyze Low-Temperature Water-Gas Shift Reactions
journal, September 2010


Catalytic hydrodeoxygenation
journal, June 2000


Gas-phase hydrodeoxygenation of guaiacol over Fe/SiO2 catalyst
journal, April 2012


Hydrodeoxygenation of Guaiacol over Carbon-Supported Metal Catalysts
journal, July 2013


Pathways for Carboxylic Acid Decomposition on Transition Metal Oxides
journal, August 1994


Mechanism of the hydrogenolysis of ethers over silica-supported rhodium catalyst modified with rhenium oxide
journal, June 2011


Effect of Surface Composition on Electronic Structure, Stability, and Electrocatalytic Properties of Pt-Transition Metal Alloys:  Pt-Skin versus Pt-Skeleton Surfaces
journal, July 2006

  • Stamenkovic, Vojislav R.; Mun, Bongjin Simon; Mayrhofer, Karl J. J.
  • Journal of the American Chemical Society, Vol. 128, Issue 27
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Heterogeneous catalysis with metal nitrides
journal, July 2013


Selective cyclohexanol production from the renewable lignin derived phenolic chemicals catalyzed by Ni/MgO
journal, November 2015


Experimental and Theoretical Insights into the Hydrogen-Efficient Direct Hydrodeoxygenation Mechanism of Phenol over Ru/TiO 2
journal, October 2015


Nanostructured molybdenum carbides supported on carbon nanotubes as efficient catalysts for one-step hydrodeoxygenation and isomerization of vegetable oils
journal, January 2011

  • Han, Junxing; Duan, Jinzhao; Chen, Ping
  • Green Chemistry, Vol. 13, Issue 9, p. 2561-2568
  • DOI: 10.1039/c1gc15421d

Vapor phase hydrodeoxygenation and hydrogenation of m -cresol on silica supported Ni, Pd and Pt catalysts
journal, October 2015


The Synergy of the Support Acid Function and the Metal Function in the Catalytic Hydrodeoxygenation of m-Cresol
journal, March 2012


The temperature and coverage dependences of adsorbed formic acid and its conversion to formate on platinum(111)
journal, February 1992

  • Columbia, M. R.; Crabtree, A. M.; Thiel, P. A.
  • Journal of the American Chemical Society, Vol. 114, Issue 4
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Selective Hydrogenolysis of Polyols and Cyclic Ethers over Bifunctional Surface Sites on Rhodium–Rhenium Catalysts
journal, August 2011

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  • Journal of the American Chemical Society, Vol. 133, Issue 32
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Coking- and Sintering-Resistant Palladium Catalysts Achieved Through Atomic Layer Deposition
journal, March 2012


The Promotional Effect of Gold in Catalysis by Palladium-Gold
journal, October 2005


Review of fast pyrolysis of biomass and product upgrading
journal, March 2012


Catalytic coupling of carboxylic acids by ketonization as a processing step in biomass conversion
journal, August 2009

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  • Journal of Catalysis, Vol. 266, Issue 1, p. 71-78
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Bimetallic effects in the hydrodeoxygenation of meta-cresol on γ-Al2O3 supported Pt–Ni and Pt–Co catalysts
journal, January 2012

  • Do, Phuong T. M.; Foster, Andrew J.; Chen, Jingguang
  • Green Chemistry, Vol. 14, Issue 5
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Demethoxylation of guaiacol and methoxybenzenes over carbon-supported Ru–Mn catalyst
journal, March 2016


Role of the Support and Reaction Conditions on the Vapor-Phase Deoxygenation of m -Cresol over Pt/C and Pt/TiO 2 Catalysts
journal, March 2016


New Catalysts for Hydroprocessing: Transition Metal Carbides and Nitrides
journal, November 1995

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  • The Journal of Physical Chemistry, Vol. 99, Issue 44
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Active Nonmetallic Au and Pt Species on Ceria-Based Water-Gas Shift Catalysts
journal, August 2003


Hydrogenation of phenol over supported platinum and palladium catalysts
journal, March 1993


Correlating Benzene Hydrogenation Activity with Binding Energies of Hydrogen and Benzene on Co-Based Bimetallic Catalysts
journal, August 2009


Multifunctional Heterogeneous Catalysts: SBA-15-Containing Primary Amines and Sulfonic Acids
journal, September 2006

  • Zeidan, Ryan K.; Hwang, Son-Jong; Davis, Mark E.
  • Angewandte Chemie International Edition, Vol. 45, Issue 38
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Gas-Phase Hydrogenation/Hydrogenolysis of Phenol over Supported Nickel Catalysts
journal, April 2000

  • Shin, Eun-Jae; Keane, Mark A.
  • Industrial & Engineering Chemistry Research, Vol. 39, Issue 4
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Preparation of Pt/Irx(IrO2)10−x bifunctional oxygen catalyst for unitized regenerative fuel cell
journal, July 2012


The critical role of water at the gold-titania interface in catalytic CO oxidation
journal, September 2014


Solid Nanoparticles that Catalyze Biofuel Upgrade Reactions at the Water/Oil Interface
journal, December 2009


Isobutanol and Methanol Synthesis on Copper Catalysts Supported on Modified Magnesium Oxide
journal, October 1997

  • Xu, Mingting; Gines, Marcelo J. L.; Hilmen, Anne-Mette
  • Journal of Catalysis, Vol. 171, Issue 1
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Directing reaction pathways by catalyst active-site selection using self-assembled monolayers
journal, September 2013

  • Pang, Simon H.; Schoenbaum, Carolyn A.; Schwartz, Daniel K.
  • Nature Communications, Vol. 4, Issue 1
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Reaction mechanism of the glycerol hydrogenolysis to 1,3-propanediol over Ir–ReOx/SiO2 catalyst
journal, June 2011


Platinum-Like Behavior of Tungsten Carbide in Surface Catalysis
journal, August 1973


Enhanced Hydrodeoxygenation of m -Cresol over Bimetallic Pt–Mo Catalysts through an Oxophilic Metal-Induced Tautomerization Pathway
journal, June 2016

  • Robinson, Allison; Ferguson, Glen Allen; Gallagher, James R.
  • ACS Catalysis, Vol. 6, Issue 7
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Catalytic upgrading of biomass fast pyrolysis vapors with titania and zirconia/titania based catalysts
journal, August 2010


Cooperative catalysis by silica-supported organic functional groups
journal, January 2008

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  • Chemical Society Reviews, Vol. 37, Issue 6
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Tungsten Monocarbide as Potential Replacement of Platinum for Methanol Electrooxidation
journal, October 2007

  • Weigert, Erich C.; Stottlemyer, Alan L.; Zellner, Michael B.
  • The Journal of Physical Chemistry C, Vol. 111, Issue 40
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Titania-Supported PdAu Bimetallic Catalysts Prepared from Dendrimer-Encapsulated Nanoparticle Precursors
journal, February 2005

  • Scott, Robert W. J.; Sivadinarayana, Chinta; Wilson, Orla M.
  • Journal of the American Chemical Society, Vol. 127, Issue 5
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Preparation and catalytic properties of transition metal carbides and nitrides
journal, June 1992


Deoxygenation of methyl laurate as a model compound to hydrocarbons on transition metal phosphide catalysts
journal, January 2014