Phosphonic acid modifiers for enhancing selective hydrodeoxygenation over Pt catalysts: The role of the catalyst support

Coan, Patrick D.; Griffin, Michael B.; Ciesielski, Peter N.; Medlin, J. Will

doi:10.1016/j.jcat.2019.03.011

Title: Phosphonic acid modifiers for enhancing selective hydrodeoxygenation over Pt catalysts: The role of the catalyst support

Journal Article · Tue Mar 26 00:00:00 EDT 2019 · Journal of Catalysis

DOI:https://doi.org/10.1016/j.jcat.2019.03.011· OSTI ID:1658629

Coan, Patrick D. ^[1]; Griffin, Michael B. ^[2]; Ciesielski, Peter N. ^[2]; Medlin, J. Will ^[1]

Univ. of Colorado, Boulder, CO (United States)
National Renewable Energy Lab. (NREL), Golden, CO (United States)

Bifunctional catalysts comprised of both noble metal and Bronsted acid sites are of growing interest for many reactions, such as the hydrodeoxygenation (HDO) of oxygenates produced by the deconstruction of lignocellulosic biomass. One method of preparing a bifunctional metal-acid catalyst is to modify the supporting material of a metal catalyst with acid-containing ligands, such as phosphonic acids (PAs), which provide tunable Bronsted acid sites at the metal-support interface. Here, we explore the potential for PA modification to improve HDO rates on Al₂O₃, TiO₂, CeO₂, and SiO₂-Al₂O₃ supports. PAs containing either alkyl or carboxylic acid (CA) tails were used to modify Pt catalysts on each support. PA modification improved HDO rates for the model compound benzyl alcohol when applied to Pt supported by Al₂O₃, TiO₂, and CeO₂, but had a negative effect on the HDO rate of Pt/SiO₂-Al₂O₃. Measurements of the relative strength of Bronsted acid sites present on the modified and unmodified catalysts suggested that PAs improved HDO when they provided new or stronger Bronsted acid sites. Additionally, the strength of the Bronsted acid sites provided by PA modifiers were tunable by altering the tail functionality, which affected the rates of HDO. These results suggest that PAs can be used to modify a variety of supports to prepare bifunctional acid-metal catalysts.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Univ. of Colorado, Boulder, CO (United States); National Renewable Energy Lab. (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Bioenergy Technologies Office; US Department of Education; USDOE Office of Energy Efficiency and Renewable Energy (EERE), Sustainable Transportation Office. Bioenergy Technologies Office

Grant/Contract Number:: SC0005239; AC36-08GO28308

OSTI ID:: 1658629

Alternate ID(s):: OSTI ID: 1507287

Report Number(s):: NREL/JA-5100-73660

Journal Information:: Journal of Catalysis, Vol. 372, Issue C; ISSN 0021-9517

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 20 works

Citation information provided by
Web of Science

References (47)

Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates Huber, George W.; Chheda, Juben N.; Barrett, Christopher J. Science, Vol. 308, Issue 5727, p. 1446-1450 https://doi.org/10.1126/science.1111166	journal	June 2005
Role of the Support and Reaction Conditions on the Vapor-Phase Deoxygenation of m -Cresol over Pt/C and Pt/TiO ₂ Catalysts Griffin, Michael B.; Ferguson, Glen A.; Ruddy, Daniel A. ACS Catalysis, Vol. 6, Issue 4 https://doi.org/10.1021/acscatal.5b02868	journal	March 2016
Catalytic routes for the conversion of biomass into liquid hydrocarbon transportation fuels Serrano-Ruiz, Juan Carlos; Dumesic, James A. Energy Environ. Sci., Vol. 4, Issue 1 https://doi.org/10.1039/C0EE00436G	journal	January 2011
Liquid-Phase Catalytic Processing of Biomass-Derived Oxygenated Hydrocarbons to Fuels and Chemicals Chheda, Juben N.; Huber, George W.; Dumesic, James A. Angewandte Chemie International Edition, Vol. 46, Issue 38, p. 7164-7183 https://doi.org/10.1002/anie.200604274	journal	September 2007
Multifunctional Heterogeneous Catalysts: SBA-15-Containing Primary Amines and Sulfonic Acids Zeidan, Ryan K.; Hwang, Son-Jong; Davis, Mark E. Angewandte Chemie International Edition, Vol. 45, Issue 38 https://doi.org/10.1002/anie.200602243	journal	September 2006
The effect of acid–base pairing on catalysis: An efficient acid–base functionalized catalyst for aldol condensation Zeidan, R.; Davis, M. Journal of Catalysis, Vol. 247, Issue 2 https://doi.org/10.1016/j.jcat.2007.02.005	journal	April 2007
Cooperative catalysis by silica-supported organic functional groups Margelefsky, Eric L.; Zeidan, Ryan K.; Davis, Mark E. Chemical Society Reviews, Vol. 37, Issue 6 https://doi.org/10.1039/b710334b	journal	January 2008
Enhancing Heterogeneous Catalysis through Cooperative Hybrid Organic–Inorganic Interfaces Notestein, Justin M.; Katz, Alexander Chemistry - A European Journal, Vol. 12, Issue 15 https://doi.org/10.1002/chem.200501152	journal	May 2006
Advancing catalytic fast pyrolysis through integrated multiscale modeling and experimentation: Challenges, progress, and perspectives Ciesielski, Peter N.; Pecha, M. Brennan; Bharadwaj, Vivek S. Wiley Interdisciplinary Reviews: Energy and Environment, Vol. 7, Issue 4 https://doi.org/10.1002/wene.297	journal	April 2018
Recent advances in heterogeneous catalysts for bio-oil upgrading via “ex situ catalytic fast pyrolysis”: catalyst development through the study of model compounds Ruddy, Daniel A.; Schaidle, Joshua A.; Ferrell III, Jack R. Green Chem., Vol. 16, Issue 2 https://doi.org/10.1039/C3GC41354C	journal	January 2014
Hydrodeoxygenation of lignin model compounds over a copper chromite catalyst Deutsch, Keenan L.; Shanks, Brent H. Applied Catalysis A: General, Vol. 447-448 https://doi.org/10.1016/j.apcata.2012.09.047	journal	December 2012
Bifunctional Catalysts for Upgrading of Biomass-Derived Oxygenates: A Review Robinson, Allison M.; Hensley, Jesse E.; Medlin, J. Will ACS Catalysis, Vol. 6, Issue 8 https://doi.org/10.1021/acscatal.6b00923	journal	July 2016
Furfuryl alcohol deoxygenation, decarbonylation, and ring-opening on Pt(111) Mark, Lesli O.; Jenkins, Alexander H.; Heinz, Hendrik Surface Science, Vol. 677 https://doi.org/10.1016/j.susc.2018.07.001	journal	November 2018
Experimental and Theoretical Insights into the Hydrogen-Efficient Direct Hydrodeoxygenation Mechanism of Phenol over Ru/TiO ₂ Nelson, Ryan C.; Baek, Byeongjin; Ruiz, Pamela ACS Catalysis, Vol. 5, Issue 11 https://doi.org/10.1021/acscatal.5b01554	journal	October 2015
Pathways for biomass-derived lignin to hydrocarbon fuels Laskar, Dhrubojyoti D.; Yang, Bin; Wang, Huamin Biofuels, Bioproducts and Biorefining, Vol. 7, Issue 5 https://doi.org/10.1002/bbb.1422	journal	July 2013
Conversion of Biomass into Chemicals over Metal Catalysts Besson, Michèle; Gallezot, Pierre; Pinel, Catherine Chemical Reviews, Vol. 114, Issue 3 https://doi.org/10.1021/cr4002269	journal	October 2013
Renewable Alkanes by Aqueous-Phase Reforming of Biomass-Derived Oxygenates Huber, George W.; Cortright, Randy D.; Dumesic, James A. Angewandte Chemie International Edition, Vol. 43, Issue 12, p. 1549-1551 https://doi.org/10.1002/anie.200353050	journal	March 2004
Inorganic Solid Acids and Their Use in Acid-Catalyzed Hydrocarbon Reactions Corma, A. Chemical Reviews, Vol. 95, Issue 3 https://doi.org/10.1021/cr00035a006	journal	May 1995
Phosphate modified ceria as a Brønsted acidic/redox multifunctional catalyst Nelson, Nicholas C.; Wang, Zhuoran; Naik, Pranjali Journal of Materials Chemistry A, Vol. 5, Issue 9 https://doi.org/10.1039/C6TA08703E	journal	January 2017
Enhancing Cooperativity in Bifunctional Acid–Pd Catalysts with Carboxylic Acid-Functionalized Organic Monolayers Coan, Patrick D.; Ellis, Lucas D.; Griffin, Michael B. The Journal of Physical Chemistry C, Vol. 122, Issue 12 https://doi.org/10.1021/acs.jpcc.7b12442	journal	March 2018
Control of interfacial acid–metal catalysis with organic monolayers Zhang, Jing; Ellis, Lucas D.; Wang, Bingwen Nature Catalysis, Vol. 1, Issue 2 https://doi.org/10.1038/s41929-017-0019-8	journal	January 2018
Phosphonic acid promotion of supported Pd catalysts for low temperature vanillin hydrodeoxygenation in ethanol Hao, Pengxiao; Schwartz, Daniel K.; Medlin, J. Will Applied Catalysis A: General, Vol. 561 https://doi.org/10.1016/j.apcata.2018.05.008	journal	July 2018
Controlling the Surface Reactivity of Titania via Electronic Tuning of Self-Assembled Monolayers Ellis, Lucas D.; Trottier, Ryan M.; Musgrave, Charles B. ACS Catalysis, Vol. 7, Issue 12 https://doi.org/10.1021/acscatal.7b02789	journal	November 2017
Self-Assembly of Carboxyalkylphosphonic Acids on Metal Oxide Powders Pawsey, Shane; Yach, Kimberly; Reven, Linda Langmuir, Vol. 18, Issue 13 https://doi.org/10.1021/la015749h	journal	June 2002
Phosphonate- and Carboxylate-Based Self-Assembled Monolayers for Organic Devices: A Theoretical Study of Surface Binding on Aluminum Oxide with Experimental Support Bauer, Thilo; Schmaltz, Thomas; Lenz, Thomas ACS Applied Materials & Interfaces, Vol. 5, Issue 13 https://doi.org/10.1021/am4008374	journal	June 2013
Infrared Spectra of Alkylphosphonic Acid Bound to Aluminium Surfaces Luschtinetz, Regina; Seifert, Gotthard; Jaehne, Evelin Macromolecular Symposia, Vol. 254, Issue 1 https://doi.org/10.1002/masy.200750837	journal	August 2007
Adsorption of phosphonic and ethylphosphonic acid on aluminum oxide surfaces Luschtinetz, Regina; Oliveira, Augusto F.; Frenzel, Johannes Surface Science, Vol. 602, Issue 7 https://doi.org/10.1016/j.susc.2008.01.035	journal	April 2008
Self-assembled Monolayers of Alkylphosphonic Acids on Aluminum Oxide Surfaces - A Theoretical Study Luschtinetz, Regina; Oliveira, Augusto F.; Duarte, Hélio A. Zeitschrift für anorganische und allgemeine Chemie, Vol. 636, Issue 8 https://doi.org/10.1002/zaac.201000016	journal	May 2010
Phosphonic acid adsorption at the TiO2 anatase (101) surface investigated by periodic hybrid HF-DFT computations Nilsing, Mattias; Lunell, Sten; Persson, Petter Surface Science, Vol. 582, Issue 1-3 https://doi.org/10.1016/j.susc.2005.02.044	journal	May 2005
Enhanced Hydrothermal Stability of γ-Al ₂ O ₃ Catalyst Supports with Alkyl Phosphonate Coatings Van Cleve, Tim; Underhill, Devon; Veiga Rodrigues, Mariana Langmuir, Vol. 34, Issue 12 https://doi.org/10.1021/acs.langmuir.8b00465	journal	March 2018
Use of DFT to achieve a rational understanding of acid?basic properties of ?-alumina surfaces Digne, M. Journal of Catalysis, Vol. 226, Issue 1 https://doi.org/10.1016/j.jcat.2004.04.020	journal	August 2004
OH Surface Density of SiO ₂ and TiO ₂ by Thermogravimetric Analysis Mueller, Roger; Kammler, Hendrik K.; Wegner, Karsten Langmuir, Vol. 19, Issue 1 https://doi.org/10.1021/la025785w	journal	January 2003
The effect of CeO ₂ on Pt/CeO ₂ /CNT catalyst for CO electrooxidation Yuan, H.; Guo, D.; Li, X. Fuel Cells, Vol. 9, Issue 2 https://doi.org/10.1002/fuce.200800100	journal	April 2009
Studies of the Hydrogen Held by Solids. VII. The Exchange of the Hydroxyl Groups of Alumina and Silica-Alumina Catalysts with Deuterated Methane Larson, John G.; Hall, W. Keith The Journal of Physical Chemistry, Vol. 69, Issue 9 https://doi.org/10.1021/j100893a044	journal	September 1965
Formation and Structure of Self-Assembled Monolayers Ulman, Abraham Chemical Reviews, Vol. 96, Issue 4, p. 1533-1554 https://doi.org/10.1021/cr9502357	journal	January 1996
An infrared study of pyridine adsorbed on acidic solids. Characterization of surface acidity Parry, E. Journal of Catalysis, Vol. 2, Issue 5 https://doi.org/10.1016/0021-9517(63)90102-7	journal	October 1963
Determination of Integrated Molar Extinction Coefficients for Infrared Absorption Bands of Pyridine Adsorbed on Solid Acid Catalysts Emeis, C. A. Journal of Catalysis, Vol. 141, Issue 2 https://doi.org/10.1006/jcat.1993.1145	journal	June 1993
Brønsted and Lewis acidity of modified montmorillonite clay catalysts determined by FT-IR spectroscopy Reddy, C. Ravindra; Bhat, Y. S.; Nagendrappa, G. Catalysis Today, Vol. 141, Issue 1-2 https://doi.org/10.1016/j.cattod.2008.04.004	journal	March 2009
Surface acidity of MCM-41 by in situ IR studies of pyridine adsorption Chakraborty, Basab; Viswanathan, B. Catalysis Today, Vol. 49, Issue 1-3 https://doi.org/10.1016/S0920-5861(98)00431-3	journal	February 1999
Quantitative Lewis/Brönsted Ratios Using DRIFTS Platon, Alexandru; Thomson, William J. Industrial & Engineering Chemistry Research, Vol. 42, Issue 24 https://doi.org/10.1021/ie030343g	journal	November 2003
Surface Reactions of Acetone on Al ₂ O ₃ , TiO ₂ , ZrO ₂ , and CeO ₂ : IR Spectroscopic Assessment of Impacts of the Surface Acid−Base Properties Zaki, M. I.; Hasan, M. A.; Pasupulety, L. Langmuir, Vol. 17, Issue 3 https://doi.org/10.1021/la000976p	journal	February 2001
Surface vacancies in close packed crystal structures Farragher, A. L. Advances in Colloid and Interface Science, Vol. 11, Issue 1 https://doi.org/10.1016/0001-8686(79)80002-0	journal	February 1979
Carbon monoxide — A low temperature infrared probe for the characterization of hydroxyl group properties on metal oxide surfaces Zaki, M. I.; Knözinger, H. Materials Chemistry and Physics, Vol. 17, Issue 1-2 https://doi.org/10.1016/0254-0584(87)90056-3	journal	April 1987
Hydrodeoxygenation of Phenol over Pd Catalysts. Effect of Support on Reaction Mechanism and Catalyst Deactivation de Souza, Priscilla M.; Rabelo-Neto, Raimundo C.; Borges, Luiz E. P. ACS Catalysis, Vol. 7, Issue 3 https://doi.org/10.1021/acscatal.6b02022	journal	February 2017
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
Structural and Electronic Properties of Selected Rutile and Anatase TiO ₂ Surfaces: An ab Initio Investigation Labat, Frédéric; Baranek, Philippe; Adamo, Carlo Journal of Chemical Theory and Computation, Vol. 4, Issue 2 https://doi.org/10.1021/ct700221w	journal	January 2008
Nanoscale surface study and reactions mechanism of 2-butanol over the γ-alumina (100) surface and nanochannel: A DFT study Dabbagh, Hossein A.; Zamani, Mehdi; Davis, Burtron H. Journal of Molecular Catalysis A: Chemical, Vol. 333, Issue 1-2 https://doi.org/10.1016/j.molcata.2010.09.016	journal	December 2010

Cited By (2)

Investigation of the effects of phosphorus on the selective hydrodeoxygenation of anisole over an Fe/SiO ₂ catalyst Wang, Shuyuan; Xu, Dan; Zhao, Jiaojiao Catalysis Science & Technology, Vol. 9, Issue 20 https://doi.org/10.1039/c9cy01415b	journal	January 2019
Role of tungsten modifiers in bimetallic catalysts for enhanced hydrodeoxygenation activity and selectivity Rasmussen, Mathew J.; Medlin, J. Will Catalysis Science & Technology, Vol. 10, Issue 2 https://doi.org/10.1039/c9cy02240f	journal	January 2020

Similar Records

Controlling Heterogeneous Catalysis with Organic Monolayers on Metal Oxides

Journal Article · Wed Oct 13 00:00:00 EDT 2021 · Accounts of Chemical Research · OSTI ID:1658629

Jenkins, Alexander H.; Medlin, J. Will

Enhancing Cooperativity in Bifunctional Acid–Pd Catalysts with Carboxylic Acid-Functionalized Organic Monolayers

Journal Article · Mon Mar 05 00:00:00 EST 2018 · Journal of Physical Chemistry. C · OSTI ID:1658629

Coan, Patrick D.; Ellis, Lucas D.; Griffin, Michael B.; +2 more

Investigating deposition sequence during synthesis of Pd/Al₂O₃ catalysts modified with organic monolayers

Journal Article · Mon Feb 21 00:00:00 EST 2022 · Catalysis Science and Technology · OSTI ID:1658629

Blanchette, Zachary; Zhang, Jing; Yazdi, Sadegh; +3 more

Related Subjects

09 BIOMASS FUELS
36 MATERIALS SCIENCE
Platinum
Hydrodeoxygenation
Phosphonic acids
Self-assembled monolayers
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
platinum
hydrodeoxygenation
phosphonic acids
self-assembled monolayers

Title: Phosphonic acid modifiers for enhancing selective hydrodeoxygenation over Pt catalysts: The role of the catalyst support

Citation Formats

References (47)

Cited By (2)

Similar Records

Related Subjects