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Title: Hydrotreatment of pyrolysis bio-oil: A review

Journal Article · · Fuel Processing Technology
 [1];  [2];  [3];  [3];  [4];  [5];  [1]
  1. Washington State University, Pullman, WA (United States)
  2. University of Tabriz (Iran)
  3. Laval University, Quebec (Canada)
  4. Curtin University, Perth, WA (United States)
  5. Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Fast pyrolysis converts >60 wt% of lignocellulosic materials into bio-oil. The two-step bio-oil hydrotreatment concept has had a major impact in the development of bio-oil hydro-treatment. In the first step, known as stabilization, the carbonyl and carboxyl functional groups are transformed into alcohols between 373 and 573 K, in the presence of noble metals (Pt, Ru and Pd) supported on carbon and metal oxides. In the second step, between 623 and 673 K, cracking and hydro-deoxygenation occur using Ru, Ni or sulfided CoMo catalysts. Transition metal phosphides and carbides are also active. The first section is devoted to summarizing the current understanding of bio-oil composition. The second section is an overview of bio-oil hydrotreatment processing parameters. Many of the bio-oil hydrotreatment studies in the literature are based on model compound results, which are reviewed in the third section. Section four is devoted to review studies with bio-oil fractions and the nature of polymerization and cross linked reactions responsible for catalyst deactivation. Furthermore, the progress in the development of new catalysts is discussed in section five. The review ends with a discussion on future prospects and challenges to hydrotreat pyrolysis bio-oils.

Research Organization:
Washington State University, Pullman, WA (United States)
Sponsoring Organization:
USDOE
Grant/Contract Number:
EE0008505
OSTI ID:
2571306
Journal Information:
Fuel Processing Technology, Journal Name: Fuel Processing Technology Vol. 195; ISSN 0378-3820
Publisher:
ElsevierCopyright Statement
Country of Publication:
United States
Language:
English

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Influence of Surfactants on the Synthesis of MoS 2 Catalysts and Their Activities in the Hydrodeoxygenation of 4-Methylphenol journal June 2014
Kinetics of Phenanthrene Hydrogenation System over CoMo/Al2O3 Catalyst journal July 2014
One Step Bio-Oil Upgrading through Hydrotreatment, Esterification, and Cracking journal July 2009
Hydrotreatment of Fast Pyrolysis Oil Using Heterogeneous Noble-Metal Catalysts
  • Wildschut, Jelle; Mahfud, Farchad H.; Venderbosch, Robbie H.
  • Industrial & Engineering Chemistry Research, Vol. 48, Issue 23, p. 10324-10334 https://doi.org/10.1021/ie9006003
journal December 2009
Catalytic Hydrocracking of Pyrolytic Lignin to Liquid Fuel in Supercritical Ethanol journal March 2010
New Catalysts for Hydroprocessing: Transition Metal Carbides and Nitrides journal November 1995
The temperature and coverage dependences of adsorbed formic acid and its conversion to formate on platinum(111) journal February 1992
Ni-Catalyzed Cleavage of Aryl Ethers in the Aqueous Phase journal December 2012
Titanium Nitride-Nickel Nanocomposite as Heterogeneous Catalyst for the Hydrogenolysis of Aryl Ethers
  • Molinari, Valerio; Giordano, Cristina; Antonietti, Markus
  • Journal of the American Chemical Society, Vol. 136, Issue 5, p. 1758-1761 https://doi.org/10.1021/ja4119412
journal January 2014
Nonmetal Catalyzed Hydrogenation of Carbonyl Compounds journal October 2014
Kinetic and Mechanistic Assessment of Alkanol/Alkanal Decarbonylation and Deoxygenation Pathways on Metal Catalysts journal September 2015
Tunability of the Adsorbate Binding on Bimetallic Alloy Nanoparticles for the Optimization of Catalytic Hydrogenation journal April 2017
Adsorption of Phenol and p-Nitrophenol from Aqueous Solutions on Metal–Organic Frameworks: Effect of Hydrogen Bonding journal March 2014
Desulfurization Reactions on Ni 2 P(001) and α-Mo 2 C(001) Surfaces:  Complex Role of P and C Sites journal March 2005
Bio-oils Hydrodeoxygenation: Adsorption of Phenolic Molecules on Oxidic Catalyst Supports journal August 2010
Adsorption and Diffusion of Oxygen Atoms on a Pt(211) Stepped Surface journal May 2013
From Heterolytic to Homolytic H 2 Dissociation on Nanostructured MgO(001) Films As a Function of the Metal Support journal May 2013
Carbon−Oxygen Bond Strength in Diphenyl Ether and Phenyl Vinyl Ether:  An Experimental and Computational Study journal July 1997
Dissociation of hydrogen on metal surfaces journal November 1991
Hydrogen Adsorption on Pd- and Ru-Doped C60 Fullerene at an Ambient Temperature journal April 2011
Catalytic Hydrogenation of Carboxylic Acid Esters, Amides, and Nitriles with Homogeneous Catalysts journal January 2014
Hydroprocessing Bio-Oil and Products Separation for Coke Production journal March 2013
Atmospheric Hydrodeoxygenation of Guaiacol over Alumina-, Zirconia-, and Silica-Supported Nickel Phosphide Catalysts journal February 2013
Hydrodeoxygenation of Lignin-Derived Phenolic Monomers and Dimers to Alkane Fuels over Bifunctional Zeolite-Supported Metal Catalysts journal January 2014
Catalytic Properties of Molybdenum Carbide, Nitride and Phosphide: A Theoretical Study journal December 2003
Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates journal June 2007
Catalyst support effects on hydrogen spillover journal January 2017
Towards the computational design of solid catalysts journal April 2009
Heterogeneous reduction of carbon dioxide by hydride-terminated silicon nanocrystals journal August 2016
The critical role of heterogeneous catalysis in lignocellulosic biomass conversion journal January 2009
Hydrodeoxygenation of bio-derived phenols to hydrocarbons using RANEY® Ni and Nafion/SiO2 catalysts journal January 2010
A new 3D mesoporous carbon replicated from commercial silica as a catalyst support for direct conversion of cellulose into ethylene glycol journal January 2010
Heteropoly acids as efficient acid catalysts in the one-step conversion of cellulose to sugar alcohols journal January 2011
Production of green aromatics and olefins by catalytic fast pyrolysis of wood sawdust journal January 2011
Renewable gasoline from aqueous phase hydrodeoxygenation of aqueous sugar solutions prepared by hydrolysis of maple wood journal January 2011
One-pot catalytic hydrocracking of raw woody biomass into chemicals over supported carbide catalysts: simultaneous conversion of cellulose, hemicellulose and lignin journal January 2012
A DFT study of furan hydrogenation and ring opening on Pd(111) journal January 2014
Depolymerization of organosolv lignin to aromatic compounds over Cu-doped porous metal oxides journal January 2014
Tungsten carbides as selective deoxygenation catalysts: experimental and computational studies of converting C3 oxygenates to propene journal January 2014
One-pot selective conversion of furfural into 1,5-pentanediol over a Pd-added Ir–ReO x /SiO 2 bifunctional catalyst journal January 2014
Recent advances in heterogeneous catalysts for bio-oil upgrading via “ex situ catalytic fast pyrolysis”: catalyst development through the study of model compounds journal January 2014
A review and perspective of recent bio-oil hydrotreating research journal January 2014
Highly efficient, NiAu-catalyzed hydrogenolysis of lignin into phenolic chemicals journal January 2014
Hydrodeoxygenation of vanillin as a bio-oil model over carbonaceous microspheres-supported Pd catalysts in the aqueous phase and Pickering emulsions journal January 2014
Role of water in metal catalyst performance for ketone hydrogenation: a joint experimental and theoretical study on levulinic acid conversion into gamma-valerolactone journal January 2014
Heterogeneous catalysis for sustainable biodiesel production via esterification and transesterification journal January 2014
Catalytic hydrotreatment of pyrolytic lignins to give alkylphenolics and aromatics using a supported Ru catalyst journal January 2014
TiO2-supported heteropoly acid catalysts for dehydration of methanol to dimethyl ether: relevance of dispersion and support interaction journal January 2015
Direct catalytic conversion of cellulose to liquid straight-chain alkanes journal January 2015
Effects of hydrogen and water on the activity and selectivity of acetic acid hydrogenation on ruthenium journal January 2014
Hydrogenolysis of cellulose to valuable chemicals over activated carbon supported mono- and bimetallic nickel/tungsten catalysts journal January 2014
Biofuels from liquid phase pyrolysis oil: a two-step hydrodeoxygenation (HDO) process journal January 2015
Heterogeneous and homogeneous catalysis for the hydrogenation of carboxylic acid derivatives: history, advances and future directions journal January 2015
Selective hydrodeoxygenation of bio-oil derived products: ketones to olefins journal January 2015
Dehydration of cellulose to levoglucosenone using polar aprotic solvents journal January 2015
From microcrystalline cellulose to hard- and softwood-based feedstocks: their hydrogenolysis to polyols over a highly efficient ruthenium–tungsten catalyst journal January 2015
Vapour phase hydrodeoxygenation of anisole over ruthenium and nickel supported mesoporous aluminosilicate journal January 2016
Low temperature hydrogenation of pyrolytic lignin over Ru/TiO 2 : 2D HSQC and 13 C NMR study of reactants and products journal January 2016
Intramolecular dehydration of biomass-derived sugar alcohols in high-temperature water journal January 2017
Ni-based bimetallic heterogeneous catalysts for energy and environmental applications journal January 2016
Metal nanoparticles supported on WO3 nanosheets for highly selective hydrogenolysis of cellulose to ethylene glycol journal January 2017
Cleavage of the lignin β-O-4 ether bond via a dehydroxylation–hydrogenation strategy over a NiMo sulfide catalyst journal January 2016
Insights into the mechanism of ethanol synthesis and ethyl acetate inhibition from acetic acid hydrogenation over Cu 2 In(100): a DFT study journal January 2017
A mechanistic model of fast pyrolysis of hemicellulose journal January 2018
Low temperature aqueous phase hydrogenation of the light oxygenate fraction of bio-oil over supported ruthenium catalysts journal January 2017
Ni 3 P as a high-performance catalytic phase for the hydrodeoxygenation of phenolic compounds journal January 2018
Cu–Pd bimetallic nanoalloy anchored on a N-rich porous organic polymer for high-performance hydrodeoxygenation of biomass-derived vanillin journal January 2018
Synergistic effect of Mo–W carbides on selective hydrodeoxygenation of guaiacol to oxygen-free aromatic hydrocarbons journal January 2019
Efficient hydro-deoxygenation of lignin derived phenolic compounds over bifunctional catalysts with optimized acid/metal interactions journal January 2018
Water-assisted selective hydrodeoxygenation of phenol to benzene over the Ru composite catalyst in the biphasic process journal January 2019
Facile synthesis of hydrophobic MoS2 and its activity and stability in the hydrodeoxygenation reaction journal January 2019
Low temperature hydrodeoxygenation of guaiacol into cyclohexane over Ni/SiO 2 catalyst combined with Hβ zeolite journal January 2019
Acetone hydrogenation over co-precipitated Ni/Al2O3, Co/Al2O3 and Fe/Al2O3 catalysts
  • Narayanan, Sankarasubbier; Unnikrishnan, Ramachandranpillai
  • Journal of the Chemical Society, Faraday Transactions, Vol. 94, Issue 8 https://doi.org/10.1039/a708124c
journal January 1998
Glycerol hydrogenolysis on heterogeneous catalysts journal January 2004
The nature of the active site in heterogeneous metal catalysis journal January 2008
Production of hydrogen, alkanes and polyols by aqueous phase processing of wood-derived pyrolysis oils journal January 2009
Catalytic conversion of biomass to biofuels journal January 2010
Highly selective and efficient hydrogenation of carboxylic acids to alcohols using titania supported Pt catalysts journal January 2010
Direct catalytic conversion of furfural to 1,5-pentanediol by hydrogenolysis of the furan ring under mild conditions over Pt/Co2AlO4 catalyst journal January 2011
Hydrodeoxygenation of pyrolysis oil fractions: process understanding and quality assessment through co-processing in refinery units journal January 2011
Hydrogenolysis of lignosulfonate into phenols over heterogeneous nickel catalysts journal April 2012
Temperature-controlled phase-transfer catalysis for ethylene glycol production from cellulose journal January 2012
Unraveling the Fischer–Tropsch mechanism: a combined DFT and microkinetic investigation of C–C bond formation on Ru journal January 2012
Bimetallic catalysts for upgrading of biomass to fuels and chemicals journal January 2012
Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation–hydrogenolysis process journal January 2013
Bimetallic effects in the hydrodeoxygenation of meta-cresol on γ-Al2O3 supported Pt–Ni and Pt–Co catalysts journal January 2012
Bio-oil upgrading at ambient pressure and temperature using zero valent metals journal January 2012
An efficient cleavage of the aryl ether C–O bond in supercritical carbon dioxide–water journal January 2013
Effective hydrodeoxygenation of biomass-derived oxygenates into unsaturated hydrocarbons by MoO3 using low H2 pressures journal January 2013
Catalytic cleavage of lignin β-O-4 link mimics using copper on alumina and magnesia–alumina journal January 2013
High-pressure fast-pyrolysis, fast-hydropyrolysis and catalytic hydrodeoxygenation of cellulose: production of liquid fuel from biomass journal January 2014
Density-functional theory studies of acetone and propanal hydrogenation on Pt(111) journal May 2002
The structure of small nickel clusters. II. Ni16–Ni28 journal May 1995
Density functional theory in surface chemistry and catalysis journal January 2011
Mechanistic Comparison of Heterogeneous and Homogeneous Hydrogenation* journal June 1969
Direct carbon-carbon coupling of furanics with acetic acid over Brønsted zeolites journal September 2016
Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates journal June 2005
Selective Phenol Hydrogenation to Cyclohexanone Over a Dual Supported Pd–Lewis Acid Catalyst journal November 2009
Renewable Chemical Commodity Feedstocks from Integrated Catalytic Processing of Pyrolysis Oils journal November 2010
Coking- and Sintering-Resistant Palladium Catalysts Achieved Through Atomic Layer Deposition journal March 2012
Platinum-Like Behavior of Tungsten Carbide in Surface Catalysis journal August 1973
Hydrogenolysis of Furfural into 1,5-Pentanediol by Employing Ni-M (M = Y or La) Composite Catalysts journal May 2017
Hydrodeoxygenation of model compounds and catalytic systems for pyrolysis bio-oils upgrading journal January 2012
Hydrodeoxygenation of Phenolic Compounds by Sulfided (Co)Mo/Al 2 O 3 Catalysts, a Combined Experimental and Theoretical Study journal April 2013
Hollow MFI Zeolite Supported Pt Catalysts for Highly Selective and Stable Hydrodeoxygenation of Guaiacol to Cycloalkanes journal March 2019
Continuous-flow Heck synthesis of 4-methoxybiphenyl and methyl 4-methoxycinnamate in supercritical carbon dioxide expanded solvent solutions journal December 2013

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