Steric Effect and Evolution of Surface Species in the Hydrodeoxygenation of Bio-Oil Model Compounds over Pt/HBEA

Foo, Guo Shiou; Rogers, Allyson K.; Yung, Matthew M.; Sievers, Carsten

doi:10.1021/acscatal.5b02684

Steric Effect and Evolution of Surface Species in the Hydrodeoxygenation of Bio-Oil Model Compounds over Pt/HBEA

Journal Article · Mon Jan 11 00:00:00 EST 2016 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.5b02684· OSTI ID:1240241

Foo, Guo Shiou ^[1]; Rogers, Allyson K. ^[1]; Yung, Matthew M. ^[2]; Sievers, Carsten ^[1]

Georgia Inst. of Technology, Atlanta, GA (United States). School of Chemical & Biomolecular Engineering
National Renewable Energy Lab. (NREL), Golden, CO (United States)

The hydrodeoxygenation of various bio-oil model compounds (anisole, m-cresol and guaiacol) over Pt/HBEA and the evolution of surface species is investigated. Depending on the functional group, different surface species are formed when the compounds are adsorbed in the presence of Lewis acid sites. For anisole, the methoxy group is decomposed to form phenate species. The methyl and methoxy group remains intact on m-cresol and guaiacol to form cresolate and methoxy phenate species, respectively. The position of these functional groups have a strong influence in the degree of hydrodeoxygenation due to steric hindrance. Based on operando transmission FTIR spectroscopy, a timeline for the formation of polynuclear aromatics and catalyst deactivation is constructed, which is also dependent on the substituents. The slow deactivation rate and low carbon content on Pt/HBEA is discussed.

View Accepted Manuscript (DOE)

Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 1240241

Report Number(s):: NREL/JA--5100-65969

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 2 Vol. 6; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (85)

Highly Selective Catalytic Conversion of Phenolic Bio-Oil to Alkanes Zhao, Chen; Kou, Yuan; Lemonidou, Angeliki A. Angewandte Chemie International Edition, Vol. 48, Issue 22, p. 3987-3990 https://doi.org/10.1002/anie.200900404	journal	May 2009
Upgrading Pyrolysis Oil over Ni/HZSM-5 by Cascade Reactions Zhao, Chen; Lercher, Johannes A. Angewandte Chemie International Edition, Vol. 51, Issue 24 https://doi.org/10.1002/anie.201108306	journal	January 2012
Kinetic, Spectroscopic, and Theoretical Assessment of Associative and Dissociative Methanol Dehydration Routes in Zeolites Jones, Andrew J.; Iglesia, Enrique Angewandte Chemie International Edition, Vol. 53, Issue 45 https://doi.org/10.1002/anie.201406823	journal	September 2014
Selective Hydrodeoxygenation of Lignin-Derived Phenolic Monomers and Dimers to Cycloalkanes on Pd/C and HZSM-5 Catalysts Zhao, Chen; Lercher, Johannes A. ChemCatChem, Vol. 4, Issue 1 https://doi.org/10.1002/cctc.201100273	journal	November 2011
Hierarchical ZSM-5 Zeolites in Shape-Selective Xylene Isomerization: Role of Mesoporosity and Acid Site Speciation Fernandez, Christian; Stan, Irina; Gilson, Jean-Pierre Chemistry - A European Journal, Vol. 16, Issue 21 https://doi.org/10.1002/chem.200903426	journal	April 2010
A DFT-Based Investigation of Hydrogen Abstraction Reactions from Methylated Polycyclic Aromatic Hydrocarbons Hemelsoet, Karen; Van Speybroeck, Veronique; Waroquier, Michel ChemPhysChem, Vol. 9, Issue 16 https://doi.org/10.1002/cphc.200800475	journal	November 2008
Hydrodeoxygenation of Guaiacol over Ceria-Zirconia Catalysts Schimming, Sarah M.; LaMont, Onaje D.; König, Michael ChemSusChem, Vol. 8, Issue 12 https://doi.org/10.1002/cssc.201500317	journal	June 2015
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
Selective Hydrodeoxygenation of Guaiacol Catalyzed by Platinum Supported on Magnesium Oxide Nimmanwudipong, Tarit; Aydin, Ceren; Lu, Jing Catalysis Letters, Vol. 142, Issue 10 https://doi.org/10.1007/s10562-012-0884-3	journal	August 2012
Stability of Pt/γ-Al2O3 Catalysts in Model Biomass Solutions Ravenelle, Ryan M.; Copeland, John R.; Van Pelt, Adam H. Topics in Catalysis, Vol. 55, Issue 3-4 https://doi.org/10.1007/s11244-012-9785-3	journal	March 2012
The Effect of Adsorbed Molecule Gas-Phase Deprotonation Enthalpy on Ion Exchange in Sodium Exchanged Zeolites: An In Situ FTIR Investigation Murphy, Brian; Davis, Mark E.; Xu, Bingjun Topics in Catalysis, Vol. 58, Issue 7-9 https://doi.org/10.1007/s11244-015-0383-z	journal	April 2015
Acidic properties of supported niobium oxide catalysts: An infrared spectroscopy investigation Datka, J. Journal of Catalysis, Vol. 135, Issue 1 https://doi.org/10.1016/0021-9517(92)90279-Q	journal	May 1992
Influence of water in the deactivation of a sulfided NiMo/γ-Al2O3 catalyst during hydrodeoxygenation Laurent, E.; Delmon, B. Journal of Catalysis, Vol. 146, Issue 1 https://doi.org/10.1016/0021-9517(94)90032-9	journal	March 1994
Study of the hydrodeoxygenation of carbonyl, car☐ylic and guaiacyl groups over sulfided CoMo/γ-Al2O3 and NiMo/γ-Al2O3 catalysts Laurent, Etienne; Delmon, Bernard Applied Catalysis A: General, Vol. 109, Issue 1 https://doi.org/10.1016/0926-860X(94)85004-6	journal	February 1994
Aromatic and Heteroaromatic Rings Colthup, Norman B.; Daly, Lawrence H.; Wiberley, Stephen E. Introduction to Infrared and Raman Spectroscopy https://doi.org/10.1016/B978-0-08-091740-5.50011-9	book	January 1990
Catalytic combustion of diesel soot over metal oxide catalysts Neri, Giovanni; Bonaccorsi, Lucio; Donato, Andrea Applied Catalysis B: Environmental, Vol. 11, Issue 2 https://doi.org/10.1016/S0926-3373(96)00045-8	journal	February 1997
Mechanisms of catalyst deactivation Bartholomew, Calvin H. Applied Catalysis A: General, Vol. 212, Issue 1-2 https://doi.org/10.1016/S0926-860X(00)00843-7	journal	April 2001
Alkylation of phenol with tert-butyl alcohol catalysed by zeolite Hβ Zhang, Kui; Huang, Changhua; Zhang, Huaibin Applied Catalysis A: General, Vol. 166, Issue 1 https://doi.org/10.1016/S0926-860X(97)00244-5	journal	January 1998
Catalytic hydrodeoxygenation Furimsky, Edward Applied Catalysis A: General, Vol. 199, Issue 2, p. 147-190 https://doi.org/10.1016/S0926-860X(99)00555-4	journal	June 2000
Simulation of FCC catalyst regeneration in a riser regenerator Bai, D.; Zhu, J-X.; Jin, Y. Chemical Engineering Journal, Vol. 71, Issue 2 https://doi.org/10.1016/S1385-8947(98)00110-7	journal	December 1998
Realumination of dealuminated HZSM-5 zeolites by acid treatment: a reexamination Omegna, Anna; Haouas, Mohamed; Kogelbauer, Andreas Microporous and Mesoporous Materials, Vol. 46, Issue 2-3 https://doi.org/10.1016/S1387-1811(01)00281-5	journal	August 2001
Preparation of nanosized micro/mesoporous composites via simultaneous synthesis of Beta/MCM-48 phases Prokešová, P.; Mintova, S.; Čejka, J. Microporous and Mesoporous Materials, Vol. 64, Issue 1-3 https://doi.org/10.1016/S1387-1811(03)00464-5	journal	October 2003
IR study on methanol-to-olefin reaction over zeolites with different pore structures and acidities Park, Ji Won; Seo, Gon Applied Catalysis A: General, Vol. 356, Issue 2 https://doi.org/10.1016/j.apcata.2009.01.001	journal	March 2009
Bio-oil upgrading over platinum catalysts using in situ generated hydrogen Fisk, Courtney A.; Morgan, Tonya; Ji, Yaying Applied Catalysis A: General, Vol. 358, Issue 2 https://doi.org/10.1016/j.apcata.2009.02.006	journal	May 2009
Deoxygenation of vegetable oils over sulfided Ni, Mo and NiMo catalysts Kubička, David; Kaluža, Luděk Applied Catalysis A: General, Vol. 372, Issue 2 https://doi.org/10.1016/j.apcata.2009.10.034	journal	January 2010
Alkali-treatment of template-containing MCM-22 zeolite and its application in alkylation and transalkylation reactions Liu, Kefeng; Xie, Sujuan; Wei, Huijuan Applied Catalysis A: General, Vol. 468 https://doi.org/10.1016/j.apcata.2013.09.009	journal	November 2013
Anisole hydrodeoxygenation over Ni–Cu bimetallic catalysts: The effect of Ni/Cu ratio on selectivity Khromova, Sofia A.; Smirnov, Andrey A.; Bulavchenko, Olga A. Applied Catalysis A: General, Vol. 470 https://doi.org/10.1016/j.apcata.2013.10.046	journal	January 2014
Hydrodeoxygenation of guaiacol with CoMo catalysts. Part I: Promoting effect of cobalt on HDO selectivity and activity Bui, Van Ngoc; Laurenti, Dorothée; Afanasiev, Pavel Applied Catalysis B: Environmental, Vol. 101, Issue 3-4, p. 239-245 https://doi.org/10.1016/j.apcatb.2010.10.025	journal	January 2011
Hydrodeoxygenation of guaiacol Bui, Van Ngoc; Laurenti, Dorothée; Delichère, Pierre Applied Catalysis B: Environmental, Vol. 101, Issue 3-4 https://doi.org/10.1016/j.apcatb.2010.10.031	journal	January 2011
Gas-phase hydrodeoxygenation of guaiacol over Fe/SiO2 catalyst Olcese, R. N.; Bettahar, M.; Petitjean, D. Applied Catalysis B: Environmental, Vol. 115-116 https://doi.org/10.1016/j.apcatb.2011.12.005	journal	April 2012
A review of catalytic hydrodeoxygenation of lignin-derived phenols from biomass pyrolysis Bu, Quan; Lei, Hanwu; Zacher, Alan H. Bioresource Technology, Vol. 124 https://doi.org/10.1016/j.biortech.2012.08.089	journal	November 2012
Noble metal catalyzed aqueous phase hydrogenation and hydrodeoxygenation of lignin-derived pyrolysis oil and related model compounds Mu, Wei; Ben, Haoxi; Du, Xiaotang Bioresource Technology, Vol. 173 https://doi.org/10.1016/j.biortech.2014.09.067	journal	December 2014
Kinetics and adsorption comparative study on the photocatalytic degradation of o-, m- and p-cresol Melián, E. Pulido; Díaz, O. González; Araña, J. Catalysis Today, Vol. 129, Issue 1-2 https://doi.org/10.1016/j.cattod.2007.08.003	journal	November 2007
Hydrodeoxygenation of guaiacol on noble metal catalysts Gutierrez, A.; Kaila, R. K.; Honkela, M. L. Catalysis Today, Vol. 147, Issue 3-4 https://doi.org/10.1016/j.cattod.2008.10.037	journal	October 2009
IR study of the interaction of phenol with oxides and sulfided CoMo catalysts for bio-fuel hydrodeoxygenation Popov, Andrey; Kondratieva, Elena; Gilson, Jean-Pierre Catalysis Today, Vol. 172, Issue 1 https://doi.org/10.1016/j.cattod.2011.02.010	journal	August 2011
Characterization of spent and regenerated catalysts recovered from a residue hydrotreating bench-scale reactor Torres-Mancera, Pablo; Rayo, Patricia; Ancheyta, Jorge Fuel, Vol. 149 https://doi.org/10.1016/j.fuel.2014.08.059	journal	June 2015
A mechanistic approach to phenol methylation on Cu1−xCoxFe2O4: FTIR study Mathew, T.; Vijayaraj, M.; Pai, S. Journal of Catalysis, Vol. 227, Issue 1 https://doi.org/10.1016/j.jcat.2004.07.005	journal	October 2004
Kinetics and mechanism of hydrogenation of furfural on Cu/SiO2 catalysts Sitthisa, Surapas; Sooknoi, Tawan; Ma, Yuguang Journal of Catalysis, Vol. 277, Issue 1 https://doi.org/10.1016/j.jcat.2010.10.005	journal	January 2011
Bifunctional transalkylation and hydrodeoxygenation of anisole over a Pt/HBeta catalyst Zhu, Xinli; Lobban, Lance L.; Mallinson, Richard G. Journal of Catalysis, Vol. 281, Issue 1 https://doi.org/10.1016/j.jcat.2011.03.030	journal	July 2011
Determination of the Au active site and surface active species via operando transmission FTIR and isotopic transient experiments on 2.3wt.% Au/TiO2 for the WGS reaction Wang, Jun; Kispersky, Vincent F.; Nicholas Delgass, W. Journal of Catalysis, Vol. 289 https://doi.org/10.1016/j.jcat.2012.02.008	journal	May 2012
Hydrodeoxygenation of m-cresol over gallium-modified beta zeolite catalysts Ausavasukhi, Artit; Huang, Yi; To, Anh T. Journal of Catalysis, Vol. 290 https://doi.org/10.1016/j.jcat.2012.03.003	journal	June 2012
Bio-oil hydrodeoxygenation: Adsorption of phenolic compounds on sulfided (Co)Mo catalysts Popov, Andrey; Kondratieva, Elena; Mariey, Laurence Journal of Catalysis, Vol. 297 https://doi.org/10.1016/j.jcat.2012.10.005	journal	January 2013
A comparative study of glycerol dehydration catalyzed by micro/mesoporous MFI zeolites Possato, Luiz Gustavo; Diniz, Rosiane N.; Garetto, Teresita Journal of Catalysis, Vol. 300 https://doi.org/10.1016/j.jcat.2013.01.003	journal	April 2013
Carbon-supported bimetallic Pd–Fe catalysts for vapor-phase hydrodeoxygenation of guaiacol Sun, Junming; Karim, Ayman M.; Zhang, He Journal of Catalysis, Vol. 306 https://doi.org/10.1016/j.jcat.2013.05.020	journal	October 2013
Highly selective bimetallic FeMoP catalyst for C–O bond cleavage of aryl ethers Rensel, Dallas J.; Rouvimov, Sergei; Gin, Megan E. Journal of Catalysis, Vol. 305 https://doi.org/10.1016/j.jcat.2013.05.026	journal	September 2013
Kinetics and mechanism of m-cresol hydrodeoxygenation on a Pt/SiO2 catalyst Nie, Lei; Resasco, Daniel E. Journal of Catalysis, Vol. 317 https://doi.org/10.1016/j.jcat.2014.05.024	journal	August 2014
Selective vapor-phase hydrodeoxygenation of anisole to benzene on molybdenum carbide catalysts Lee, Wen-Sheng; Wang, Zhenshu; Wu, Ryan J. Journal of Catalysis, Vol. 319 https://doi.org/10.1016/j.jcat.2014.07.025	journal	November 2014
Molecular structure, spectroscopic studies (FTIR, FT-Raman and NMR) and HOMO–LUMO analysis of 6-chloro-o-cresol and 4-chloro-3-methyl phenol by density functional theoretical study Krishnakumar, V.; Kumar, M.; Prabavathi, N. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 97 https://doi.org/10.1016/j.saa.2012.05.070	journal	November 2012
Kinetics of Upgrading of Anisole with Hydrogen Catalyzed by Platinum Supported on Alumina Saidi, Majid; Rostami, Parisa; Rahimpour, Hamid Reza Energy & Fuels, Vol. 29, Issue 8 https://doi.org/10.1021/acs.energyfuels.5b00297	journal	July 2015
Investigation of Coke Deposits on Al-MCM-41 Rozwadowski, M.; Lezanska, M.; Wloch, J. Chemistry of Materials, Vol. 13, Issue 5 https://doi.org/10.1021/cm001147s	journal	May 2001
Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering Huber, George W.; Iborra, Sara; Corma, Avelino Chemical Reviews, Vol. 106, Issue 9, p. 4044-4098 https://doi.org/10.1021/cr068360d	journal	September 2006
Hydrogen Spillover. Facts and Fiction Prins, R. Chemical Reviews, Vol. 112, Issue 5 https://doi.org/10.1021/cr200346z	journal	February 2012
Aqueous Phase Hydroalkylation and Hydrodeoxygenation of Phenol by Dual Functional Catalysts Comprised of Pd/C and H/La-BEA Zhao, Chen; Song, Wenji; Lercher, Johannes A. ACS Catalysis, Vol. 2, Issue 12 https://doi.org/10.1021/cs300418a	journal	November 2012
Stability of Pt/γ-Al ₂ O ₃ Catalysts in Lignin and Lignin Model Compound Solutions under Liquid Phase Reforming Reaction Conditions Jongerius, Anna L.; Copeland, John R.; Foo, Guo Shiou ACS Catalysis, Vol. 3, Issue 3 https://doi.org/10.1021/cs300684y	journal	February 2013
Role of Lewis and Brønsted Acid Sites in the Dehydration of Glycerol over Niobia Foo, Guo Shiou; Wei, Daniel; Sholl, David S. ACS Catalysis, Vol. 4, Issue 9 https://doi.org/10.1021/cs5006376	journal	August 2014
Effects of Carbohydrates on the Hydrodeoxygenation of Lignin-Derived Phenolic Compounds Dwiatmoko, Adid Adep; Lee, Sangheon; Ham, Hyung Chul ACS Catalysis, Vol. 5, Issue 1 https://doi.org/10.1021/cs501567x	journal	November 2014
Theoretical Investigation of the Reaction Mechanism of the Guaiacol Hydrogenation over a Pt(111) Catalyst Lu, Jianmin; Behtash, Sina; Mamun, Osman ACS Catalysis, Vol. 5, Issue 4 https://doi.org/10.1021/cs5016244	journal	March 2015
Role of Keto Intermediates in the Hydrodeoxygenation of Phenol over Pd on Oxophilic Supports de Souza, Priscilla M.; Rabelo-Neto, Raimundo C.; Borges, Luiz E. P. ACS Catalysis, Vol. 5, Issue 2 https://doi.org/10.1021/cs501853t	journal	January 2015
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
Historical Developments in Hydroprocessing Bio-oils Elliott, Douglas C. Energy & Fuels, Vol. 21, Issue 3, p. 1792-1815 https://doi.org/10.1021/ef070044u	journal	May 2007
Catalytic Hydrodeoxygenation of Guaiacol on Rh-Based and Sulfided CoMo and NiMo Catalysts Lin, Yu-Chuan; Li, Chia-Liang; Wan, Hou-Peng Energy & Fuels, Vol. 25, Issue 3 https://doi.org/10.1021/ef101521z	journal	March 2011
Anisole and Guaiacol Hydrodeoxygenation over Monolithic Pt–Sn Catalysts González-Borja, Miguel Ángel; Resasco, Daniel E. Energy & Fuels, Vol. 25, Issue 9 https://doi.org/10.1021/ef200728r	journal	September 2011
Design of a High-Pressure Flow-Reactor System for Catalytic Hydrodeoxygenation: Guaiacol Conversion Catalyzed by Platinum Supported on MgO Nimmanwudipong, Tarit; Runnebaum, Ron C.; Brodwater, Kevin Energy & Fuels, Vol. 28, Issue 2 https://doi.org/10.1021/ef4020026	journal	January 2014
Efficient Conversion of m -Cresol to Aromatics on a Bifunctional Pt/HBeta Catalyst Zhu, Xinli; Nie, Lei; Lobban, Lance L. Energy & Fuels, Vol. 28, Issue 6 https://doi.org/10.1021/ef500768r	journal	June 2014
Coke Deposition on Ni/HZSM-5 in Bio-oil Hydrodeoxygenation Processing Li, Yu; Zhang, Changsen; Liu, Yonggang Energy & Fuels, Vol. 29, Issue 3 https://doi.org/10.1021/ef5024669	journal	March 2015
Upgrading Process of 4-Methylanisole as a Lignin-Derived Bio-Oil Catalyzed by Pt/γ-Al ₂ O ₃ : Kinetic Investigation and Reaction Network Development Saidi, Majid; Rahimpour, Mohammad Reza; Raeissi, Sona Energy & Fuels, Vol. 29, Issue 5 https://doi.org/10.1021/ef5029284	journal	April 2015
Controlling the Water Content of Biomass Fast Pyrolysis Oil Westerhof, Roel J. M.; Kuipers, Norbert J. M.; Kersten, Sascha R. A. Industrial & Engineering Chemistry Research, Vol. 46, Issue 26 https://doi.org/10.1021/ie070684k	journal	December 2007
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
The Determination of Pore Volume and Area Distributions in Porous Substances. I. Computations from Nitrogen Isotherms Barrett, Elliott P.; Joyner, Leslie G.; Halenda, Paul P. Journal of the American Chemical Society, Vol. 73, Issue 1 https://doi.org/10.1021/ja01145a126	journal	January 1951
Adsorption of Gases in Multimolecular Layers Brunauer, Stephen; Emmett, P. H.; Teller, Edward Journal of the American Chemical Society, Vol. 60, Issue 2, p. 309-319 https://doi.org/10.1021/ja01269a023	journal	February 1938
Catalytic Hydrodeoxygenation of Methyl-Substituted Phenols: Correlations of Kinetic Parameters with Molecular Properties Massoth, F. E.; Politzer, P.; Concha, M. C. The Journal of Physical Chemistry B, Vol. 110, Issue 29 https://doi.org/10.1021/jp057332g	journal	July 2006
Surface Transport Processes and Sticking Probability of Aromatic Molecules in HZSM-5 Reitmeier, S. J.; Mukti, R. R.; Jentys, A. The Journal of Physical Chemistry C, Vol. 112, Issue 7 https://doi.org/10.1021/jp077339t	journal	February 2008
Bio-oils Hydrodeoxygenation: Adsorption of Phenolic Molecules on Oxidic Catalyst Supports Popov, Andrey; Kondratieva, Elena; Goupil, Jean Michel The Journal of Physical Chemistry C, Vol. 114, Issue 37 https://doi.org/10.1021/jp101949j	journal	August 2010
Stability of Zeolites in Hot Liquid Water Ravenelle, Ryan M.; Schüβler, Florian; D’Amico, Andrew The Journal of Physical Chemistry C, Vol. 114, Issue 46 https://doi.org/10.1021/jp104639e	journal	November 2010
Steaming of Zeolite BEA and Its Effect on Acidity: A Comparative NMR and IR Spectroscopic Study Maier, Sarah M.; Jentys, Andreas; Lercher, Johannes A. The Journal of Physical Chemistry C, Vol. 115, Issue 16 https://doi.org/10.1021/jp108338g	journal	April 2011
Surface Interactions of Glycerol with Acidic and Basic Metal Oxides Copeland, John R.; Santillan, Ivan A.; Schimming, Sarah McNew The Journal of Physical Chemistry C, Vol. 117, Issue 41 https://doi.org/10.1021/jp4078695	journal	October 2013
Conversion of Methanol to Hydrocarbons: Spectroscopic Characterization of Carbonaceous Species Formed over H-ZSM-5 Palumbo, Luisa; Bonino, Francesca; Beato, Pablo The Journal of Physical Chemistry C, Vol. 112, Issue 26 https://doi.org/10.1021/jp800762v	journal	June 2008
Surface Interactions of C ₂ and C ₃ Polyols with γ-Al ₂ O ₃ and the Role of Coadsorbed Water Copeland, John R.; Shi, Xue-Rong; Sholl, David S. Langmuir, Vol. 29, Issue 2 https://doi.org/10.1021/la304074x	journal	December 2012
Maximizing the catalytic function of hydrogen spillover in platinum-encapsulated aluminosilicates with controlled nanostructures Im, Juhwan; Shin, Hyeyoung; Jang, Haeyoun Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms4370	journal	February 2014
Hydrodeoxygenation of bio-derived phenols to hydrocarbons using RANEY® Ni and Nafion/SiO₂ catalysts Zhao, Chen; Kou, Yuan; Lemonidou, Angeliki A. Chemical Communications, Vol. 46, Issue 3, p. 412-414 https://doi.org/10.1039/B916822B	journal	January 2010
Upgrading of lignin-derived bio-oils by catalytic hydrodeoxygenation Saidi, Majid; Samimi, Fereshteh; Karimipourfard, Dornaz Energy Environ. Sci., Vol. 7, Issue 1 https://doi.org/10.1039/C3EE43081B	journal	January 2014
Insights into the catalytic activity and surface modification of MoO ₃ during the hydrodeoxygenation of lignin-derived model compounds into aromatic hydrocarbons under low hydrogen pressures Prasomsri, Teerawit; Shetty, Manish; Murugappan, Karthick Energy Environ. Sci., Vol. 7, Issue 8 https://doi.org/10.1039/C4EE00890A	journal	January 2014
Insights in the hydrotreatment of fast pyrolysis oil using a ruthenium on carbon catalyst Wildschut, Jelle; Iqbal, Muhammad; Mahfud, Farchad H. Energy & Environmental Science, Vol. 3, Issue 7 https://doi.org/10.1039/b923170f	journal	January 2010
Effective hydrodeoxygenation of biomass-derived oxygenates into unsaturated hydrocarbons by MoO₃ using low H₂ pressures Prasomsri, Teerawit; Nimmanwudipong, Tarit; Román-Leshkov, Yuriy Energy & Environmental Science, Vol. 6, Issue 6, p. 1732-1738 https://doi.org/10.1039/c3ee24360e	journal	January 2013
Coordinatively Unsaturated Al3+ Centers as Binding Sites for Active Catalyst Phases of Platinum on -Al2O3 Kwak, J. H.; Hu, J.; Mei, D. Science, Vol. 325, Issue 5948 https://doi.org/10.1126/science.1176745	journal	September 2009

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