Investigation of the reaction mechanism of the hydrodeoxygenation of propionic acid over a Rh(1 1 1) surface: A first principles study

Yang, Wenqiang; Solomon, Rajadurai Vijay; Mamun, Osman; Bond, Jesse Q.; Heyden, Andreas

doi:10.1016/j.jcat.2020.08.015

Title: Investigation of the reaction mechanism of the hydrodeoxygenation of propionic acid over a Rh(1 1 1) surface: A first principles study

Journal Article · 21 August 2020 · Journal of Catalysis

DOI: https://doi.org/10.1016/j.jcat.2020.08.015 · OSTI ID:1656889

Yang, Wenqiang ^[1]; Solomon, Rajadurai Vijay ^[2]; Mamun, Osman ^[2]; Bond, Jesse Q. ^[3];

^[2]

University of South Carolina, Columbia, SC (United States); University of South Carolina
University of South Carolina, Columbia, SC (United States)
Syracuse University, NY (United States)

Microkinetic models based on first principles calculations have been used to study the vapor and liquid phase hydrodeoxygenation of propionic acid on a Rh(111) surface. Calculations suggest that both decarboxylation and decarbonylation do not occur at an appreciable rate under all reaction environments. Propanol and propionaldehyde are the main products on this surface and they are produced at similar rates in both vapor and liquid phase environments. While a condensed phase can shift the reaction rate, the dominant pathways and selectivity towards the various products are hardly affected. At 473 K, the turnover frequency is increased by about a factor of 1.5 in liquid water relative to the gas phase. In liquid 1,4-dioxane, the turnover frequency is also slightly increased relative to the gas phase. Here, given the uncertainty in Rh cavity radius in the liquid phase calculations, computations with different cavity radii have been performed. With larger Rh cavity radius, the promotional effect of the solvents on the turnover frequency becomes more significant, while practically no changes are observed for a smaller cavity radius.

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Research Organization:: University of South Carolina, Columbia, SC (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; National Science Foundation

Grant/Contract Number:: SC0007167

OSTI ID:: 1656889

Journal Information:: Journal of Catalysis, Journal Name: Journal of Catalysis Vol. 391; ISSN 0021-9517

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (63)

Beyond Petrochemicals: The Renewable Chemicals Industry Vennestrøm, P. N. R.; Osmundsen, C. M.; Christensen, C. H. Angewandte Chemie International Edition, Vol. 50, Issue 45 https://doi.org/10.1002/anie.201102117	journal	October 2011
Combination of Cp*Rh ^III -Catalyzed C−H Activation and a Wagner-Meerwein-Type Rearrangement Wang, Xiaoming; Lerchen, Andreas; Gensch, Tobias Angewandte Chemie International Edition, Vol. 56, Issue 5 https://doi.org/10.1002/anie.201610117	journal	December 2016
Aqueous-Phase Hydrogenation of Acetic Acid over Transition Metal Catalysts Olcay, Hakan; Xu, Lijun; Xu, Ye ChemCatChem, Vol. 2, Issue 11 https://doi.org/10.1002/cctc.201000134	journal	August 2010
Finding the Rate-Determining Step in a Mechanism Campbell, Charles T. Journal of Catalysis, Vol. 204, Issue 2 https://doi.org/10.1006/jcat.2001.3396	journal	December 2001
Reaction Paths in the Hydrogenolysis of Acetic Acid to Ethanol over Pd(111), Re(0001), and PdRe Alloys Pallassana, Venkataraman; Neurock, Matthew Journal of Catalysis, Vol. 209, Issue 2 https://doi.org/10.1006/jcat.2002.3585	journal	July 2002
Transformation of Vegetable Oils into Hydrocarbons over Mesoporous-Alumina-Supported CoMo Catalysts Kubička, David; Šimáček, Pavel; Žilková, Naděžda Topics in Catalysis, Vol. 52, Issue 1-2 https://doi.org/10.1007/s11244-008-9145-5	journal	December 2008
Hydroprocessing of Bio-Oils and Oxygenates to Hydrocarbons. Understanding the Reaction Routes Donnis, Bjørn; Egeberg, Rasmus Gottschalck; Blom, Peder Topics in Catalysis, Vol. 52, Issue 3 https://doi.org/10.1007/s11244-008-9159-z	journal	January 2009
Catalytic Deoxygenation of C18 Fatty Acids Over Mesoporous Pd/C Catalyst for Synthesis of Biofuels Simakova, Irina; Rozmysłowicz, Bartosz; Simakova, Olga Topics in Catalysis, Vol. 54, Issue 8-9 https://doi.org/10.1007/s11244-011-9608-y	journal	January 2011
Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set Kresse, G.; Furthmüller, J. Computational Materials Science, Vol. 6, Issue 1, p. 15-50 https://doi.org/10.1016/0927-0256(96)00008-0	journal	July 1996
Processing biomass in conventional oil refineries: Production of high quality diesel by hydrotreating vegetable oils in heavy vacuum oil mixtures Huber, George W.; O’Connor, Paul; Corma, Avelino Applied Catalysis A: General, Vol. 329 https://doi.org/10.1016/j.apcata.2007.07.002	journal	October 2007
Catalytic hydroconversion of tricaprylin and caprylic acid as model reaction for biofuel production from triglycerides Boda, László; Onyestyák, György; Solt, Hanna Applied Catalysis A: General, Vol. 374, Issue 1-2 https://doi.org/10.1016/j.apcata.2009.12.005	journal	February 2010
Hydrodeoxygenation of oleic acid and canola oil over alumina-supported metal nitrides Monnier, Jacques; Sulimma, Hardi; Dalai, Ajay Applied Catalysis A: General, Vol. 382, Issue 2 https://doi.org/10.1016/j.apcata.2010.04.035	journal	July 2010
Catalytic deoxygenation of oleic acid in continuous gas flow for the production of diesel-like hydrocarbons Arend, Matthias; Nonnen, Thomas; Hoelderich, Wolfgang F. Applied Catalysis A: General, Vol. 399, Issue 1-2 https://doi.org/10.1016/j.apcata.2011.04.004	journal	May 2011
Gas-phase, catalytic hydrodeoxygenation of propanoic acid, over supported group VIII noble metals: Metal and support effects Lugo-José, Yuliana K.; Monnier, John R.; Williams, Christopher T. Applied Catalysis A: General, Vol. 469 https://doi.org/10.1016/j.apcata.2013.10.025	journal	January 2014
Influence of fatty acid composition of raw materials on biodiesel properties Ramos, María Jesús; Fernández, Carmen María; Casas, Abraham Bioresource Technology, Vol. 100, Issue 1 https://doi.org/10.1016/j.biortech.2008.06.039	journal	January 2009
Decarboxylation of fatty acids over Pd supported on mesoporous carbon Simakova, Irina; Simakova, Olga; Mäki-Arvela, Päivi Catalysis Today, Vol. 150, Issue 1-2 https://doi.org/10.1016/j.cattod.2009.07.064	journal	February 2010
Dependence of biodiesel fuel properties on the structure of fatty acid alkyl esters Knothe, Gerhard Fuel Processing Technology, Vol. 86, Issue 10 https://doi.org/10.1016/j.fuproc.2004.11.002	journal	June 2005
Design of solid acid catalysts for aqueous-phase dehydration of carbohydrates: The role of Lewis and Brønsted acid sites Weingarten, Ronen; Tompsett, Geoffrey A.; Conner, Wm Curtis Journal of Catalysis, Vol. 279, Issue 1, p. 174-182 https://doi.org/10.1016/j.jcat.2011.01.013	journal	April 2011
Microkinetic modeling of the decarboxylation and decarbonylation of propanoic acid over Pd(111) model surfaces based on parameters obtained from first principles Lu, Jianmin; Behtash, Sina; Faheem, Muhammad Journal of Catalysis, Vol. 305 https://doi.org/10.1016/j.jcat.2013.04.026	journal	September 2013
Theoretical investigation of the decarboxylation and decarbonylation mechanism of propanoic acid over a Ru(0 0 0 1) model surface Lu, Jianmin; Faheem, Muhammad; Behtash, Sina Journal of Catalysis, Vol. 324 https://doi.org/10.1016/j.jcat.2015.01.005	journal	April 2015
Examination of the key issues in microkinetics: CO oxidation on Rh(1 1 1) Guo, Chenxi; Mao, Yu; Yao, Zihao Journal of Catalysis, Vol. 379 https://doi.org/10.1016/j.jcat.2019.09.012	journal	November 2019
Investigation of solvent effects in the hydrodeoxygenation of levulinic acid to γ-valerolactone over Ru catalysts Mamun, Osman; Saleheen, Mohammad; Bond, Jesse Q. Journal of Catalysis, Vol. 379 https://doi.org/10.1016/j.jcat.2019.09.026	journal	November 2019
Unraveling the mechanism of the hydrodeoxygenation of propionic acid over a Pt (1 1 1) surface in vapor and liquid phases Yang, Wenqiang; Solomon, Rajadurai Vijay; Lu, Jianmin Journal of Catalysis, Vol. 381 https://doi.org/10.1016/j.jcat.2019.11.036	journal	January 2020
Computational Studies of Synthetically Relevant Homogeneous Organometallic Catalysis Involving Ni, Pd, Ir, and Rh: An Overview of Commonly Employed DFT Methods and Mechanistic Insights Sperger, Theresa; Sanhueza, Italo A.; Kalvet, Indrek Chemical Reviews, Vol. 115, Issue 17 https://doi.org/10.1021/acs.chemrev.5b00163	journal	July 2015
A Method for Obtaining Liquid–Solid Adsorption Rates from Molecular Dynamics Simulations: Applied to Methanol on Pt(111) in H ₂ O Zhang, Xiaohong; Savara, Aditya; Getman, Rachel B. Journal of Chemical Theory and Computation, Vol. 16, Issue 4 https://doi.org/10.1021/acs.jctc.9b01249	journal	March 2020
Modeling Flexible Molecules in Solution: A p K _a Case Study Haworth, Naomi L.; Wang, Qinrui; Coote, Michelle L. The Journal of Physical Chemistry A, Vol. 121, Issue 27 https://doi.org/10.1021/acs.jpca.7b04133	journal	June 2017
Solvation Effects in the Hydrodeoxygenation of Propanoic Acid over a Model Pd(211) Catalyst Behtash, Sina; Lu, Jianmin; Mamun, Osman The Journal of Physical Chemistry C, Vol. 120, Issue 5 https://doi.org/10.1021/acs.jpcc.5b10419	journal	February 2016
Computational Investigation of Aqueous Phase Effects on the Dehydrogenation and Dehydroxylation of Polyols over Pt(111) Saleheen, Mohammad; Zare, Mehdi; Faheem, Muhammad The Journal of Physical Chemistry C, Vol. 123, Issue 31 https://doi.org/10.1021/acs.jpcc.9b04994	journal	July 2019
Quantitative Studies of the Coverage Effects on Microkinetic Simulations for NO Oxidation on Pt(111) Ding, Yunxuan; Xu, Yarong; Song, Yihui The Journal of Physical Chemistry C, Vol. 123, Issue 45 https://doi.org/10.1021/acs.jpcc.9b08208	journal	October 2019
The Degree of Rate Control: A Powerful Tool for Catalysis Research Campbell, Charles T. ACS Catalysis, Vol. 7, Issue 4 https://doi.org/10.1021/acscatal.7b00115	journal	March 2017
Quantitative Determination of C–C Coupling Mechanisms and Detailed Analyses on the Activity and Selectivity for Fischer–Tropsch Synthesis on Co(0001): Microkinetic Modeling with Coverage Effects Yao, Zihao; Guo, Chenxi; Mao, Yu ACS Catalysis, Vol. 9, Issue 7 https://doi.org/10.1021/acscatal.9b01150	journal	May 2019
On the Mechanism of Stereoselection in Rh-Catalyzed Asymmetric Hydrogenation: A General Approach for Predicting the Sense of Enantioselectivity Gridnev, Ilya D.; Imamoto, Tsuneo Accounts of Chemical Research, Vol. 37, Issue 9 https://doi.org/10.1021/ar030156e	journal	September 2004
Direct Functionalization of Nitrogen Heterocycles via Rh-Catalyzed C−H Bond Activation Lewis, Jared C.; Bergman, Robert G.; Ellman, Jonathan A. Accounts of Chemical Research, Vol. 41, Issue 8 https://doi.org/10.1021/ar800042p	journal	August 2008
Rhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H Bond Activation Colby, Denise A.; Bergman, Robert G.; Ellman, Jonathan A. Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900005n	journal	February 2010
Catalytic Deoxygenation of Fatty Acids and Their Derivatives Mäki-Arvela, Päivi; Kubickova, Iva; Snåre, Mathias Energy & Fuels, Vol. 21, Issue 1, p. 30-41 https://doi.org/10.1021/ef060455v	journal	January 2007
Kinetics of Aqueous-Phase Hydrogenation of Organic Acids and Their Mixtures over Carbon Supported Ruthenium Catalyst Chen, Yuqing; Miller, Dennis J.; Jackson, James E. Industrial & Engineering Chemistry Research, Vol. 46, Issue 10 https://doi.org/10.1021/ie0614632	journal	May 2007
Influence of Hydrogen in Catalytic Deoxygenation of Fatty Acids and Their Derivatives over Pd/C Rozmysłowicz, Bartosz; Mäki-Arvela, Päivi; Tokarev, Anton Industrial & Engineering Chemistry Research, Vol. 51, Issue 26 https://doi.org/10.1021/ie202421x	journal	December 2011
Conductor-like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena Klamt, Andreas The Journal of Physical Chemistry, Vol. 99, Issue 7 https://doi.org/10.1021/j100007a062	journal	February 1995
Electronic and Steric Control of Regioselectivities in Rh(I)-Catalyzed (5 + 2) Cycloadditions: Experiment and Theory Liu, Peng; Sirois, Lauren E.; Cheong, Paul Ha-Yeon Journal of the American Chemical Society, Vol. 132, Issue 29 https://doi.org/10.1021/ja103253d	journal	July 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 23 https://doi.org/10.1021/ja9000097	journal	June 2009
Theoretical Investigation of the Reaction Mechanism of the Decarboxylation and Decarbonylation of Propanoic Acid on Pd(111) Model Surfaces Lu, Jianmin; Behtash, Sina; Heyden, Andreas The Journal of Physical Chemistry C, Vol. 116, Issue 27 https://doi.org/10.1021/jp301926t	journal	June 2012
New Implicit Solvation Scheme for Solid Surfaces Faheem, Muhammad; Suthirakun, Suwit; Heyden, Andreas The Journal of Physical Chemistry C, Vol. 116, Issue 42 https://doi.org/10.1021/jp308212h	journal	October 2012
Effect of Palladium Surface Structure on the Hydrodeoxygenation of Propanoic Acid: Identification of Active Sites Behtash, Sina; Lu, Jianmin; Williams, Christopher T. The Journal of Physical Chemistry C, Vol. 119, Issue 4 https://doi.org/10.1021/jp511618u	journal	January 2015
Refinement and Parametrization of COSMO-RS Klamt, Andreas; Jonas, Volker; Bürger, Thorsten The Journal of Physical Chemistry A, Vol. 102, Issue 26 https://doi.org/10.1021/jp980017s	journal	June 1998
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
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
Solvent effects on the hydrodeoxygenation of propanoic acid over Pd(111) model surfaces Behtash, Sina; Lu, Jianmin; Faheem, Muhammad Green Chem., Vol. 16, Issue 2 https://doi.org/10.1039/C3GC41368C	journal	January 2014
A DFT study of direct furfural conversion to 2-methylfuran on the Ru/Co ₃ O ₄ surface Dong, He; Zheng, Ying; Hu, P. Physical Chemistry Chemical Physics, Vol. 21, Issue 3 https://doi.org/10.1039/C8CP06545D	journal	January 2019
DFT study of furfural conversion on a Re/Pt bimetallic surface: synergetic effect on the promotion of hydrodeoxygenation Dong, He; Zheng, Ying; Hu, P. Physical Chemistry Chemical Physics, Vol. 21, Issue 16 https://doi.org/10.1039/C8CP07806H	journal	January 2019
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
Production of levulinic acid and gamma-valerolactone (GVL) from cellulose using GVL as a solvent in biphasic systems Wettstein, Stephanie G.; Alonso, David Martin; Chong, Yuxuan Energy & Environmental Science, Vol. 5, Issue 8, p. 8199-8203 https://doi.org/10.1039/c2ee22111j	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
Comparison of methods for finding saddle points without knowledge of the final states Olsen, R. A.; Kroes, G. J.; Henkelman, G. The Journal of Chemical Physics, Vol. 121, Issue 20 https://doi.org/10.1063/1.1809574	journal	November 2004
Efficient methods for finding transition states in chemical reactions: Comparison of improved dimer method and partitioned rational function optimization method Heyden, Andreas; Bell, Alexis T.; Keil, Frerich J. The Journal of Chemical Physics, Vol. 123, Issue 22 https://doi.org/10.1063/1.2104507	journal	December 2005
A dimer method for finding saddle points on high dimensional potential surfaces using only first derivatives Henkelman, Graeme; Jónsson, Hannes The Journal of Chemical Physics, Vol. 111, Issue 15 https://doi.org/10.1063/1.480097	journal	October 1999
Special points for Brillouin-zone integrations Monkhorst, Hendrik J.; Pack, James D. Physical Review B, Vol. 13, Issue 12, p. 5188-5192 https://doi.org/10.1103/PhysRevB.13.5188	journal	June 1976
Accurate and simple density functional for the electronic exchange energy: Generalized gradient approximation Perdew, John P.; Yue, Wang Physical Review B, Vol. 33, Issue 12 https://doi.org/10.1103/PhysRevB.33.8800	journal	June 1986
Accurate and simple analytic representation of the electron-gas correlation energy Perdew, John P.; Wang, Yue Physical Review B, Vol. 45, Issue 23, p. 13244-13249 https://doi.org/10.1103/PhysRevB.45.13244	journal	June 1992
Ab initiomolecular dynamics for liquid metals Kresse, G.; Hafner, J. Physical Review B, Vol. 47, Issue 1, p. 558-561 https://doi.org/10.1103/PhysRevB.47.558	journal	January 1993
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
Cellulosic Biofuels--Got Gasoline? Regalbuto, J. R. Science, Vol. 325, Issue 5942 https://doi.org/10.1126/science.1174581	journal	August 2009
An adsorption isotherm of multi-site occupancy model for homogeneous surface. Nitta, Tomoshige; Shigetomi, Takuo; Kuro-Oka, Masayuki Journal of Chemical Engineering of Japan, Vol. 17, Issue 1 https://doi.org/10.1252/jcej.17.39	journal	January 1984
Biomass as Renewable Energy: Worldwide Research Trends Perea-Moreno, Miguel-Angel; Samerón-Manzano, Esther; Perea-Moreno, Alberto-Jesus Sustainability, Vol. 11, Issue 3 https://doi.org/10.3390/su11030863	journal	February 2019

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Title: Investigation of the reaction mechanism of the hydrodeoxygenation of propionic acid over a Rh(1 1 1) surface: A first principles study

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