Understanding Selective Hydrodeoxygenation of 1,2- and 1,3-Propanediols on Cu/Mo 2 C via Multiscale Modeling

You, Kyung-Eun; Ammal, Salai C.; Lin, Zhexi; Heyden, Andreas

doi:10.1021/acscatal.2c00261

Understanding Selective Hydrodeoxygenation of 1,2- and 1,3-Propanediols on Cu/Mo ₂ C via Multiscale Modeling

Journal Article · 04 April 2022 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.2c00261· OSTI ID:1982008

You, Kyung-Eun ^[1]; Ammal, Salai C. ^[1]; ^[2]; ^[1]

Department of Chemical Engineering, University of South Carolina, Columbia, South Carolina 29208, United States
Department of Chemical Engineering, Columbia University, New York, New York 10027, United States

Not provided.

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC02-05CH11231;

OSTI ID:: 1982008

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 8 Vol. 12; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (61)

Reaction Pathways of Biomass-Derived Oxygenates over Metals and Carbides: From Model Surfaces to Supported Catalysts Xiong, Ke; Yu, Weiting; Vlachos, Dionisios G. ChemCatChem, Vol. 7, Issue 9 https://doi.org/10.1002/cctc.201403067	journal	March 2015
Molybdenum Carbide as a Highly Selective Deoxygenation Catalyst for Converting Furfural to 2-Methylfuran Xiong, Ke; Lee, Wen-Sheng; Bhan, Aditya ChemSusChem, Vol. 7, Issue 8 https://doi.org/10.1002/cssc.201402033	journal	April 2014
From 5-Hydroxymethylfurfural (HMF) to Polymer Precursors: Catalyst Screening Studies on the Conversion of 1,2,6-hexanetriol to 1,6-hexanediol Buntara, Teddy; Noel, Sebastien; Phua, Pim Huat Topics in Catalysis, Vol. 55, Issue 7-10 https://doi.org/10.1007/s11244-012-9839-6	journal	July 2012
The molecular structure of 1,3-propanediol in the gas phase, an electron diffraction study Kinneging, A. J.; Mom, V.; Mijlhoff, F. C. Journal of Molecular Structure, Vol. 82, Issue 3-4 https://doi.org/10.1016/0022-2860(82)80042-2	journal	July 1982
Thermal desorption of gases Redhead, P. A. Vacuum, Vol. 12, Issue 4 https://doi.org/10.1016/0042-207X(62)90978-8	journal	July 1962
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
Hydrogen bonds and proton transfer in general-catalytic transition-state stabilization in enzyme catalysis Schowen, K. B.; Limbach, H. -H.; Denisov, G. S. Biochimica et Biophysica Acta (BBA) - Bioenergetics, Vol. 1458, Issue 1 https://doi.org/10.1016/S0005-2728(00)00059-1	journal	May 2000
Vapor-phase reaction of polyols over copper catalysts Sato, Satoshi; Akiyama, Masaki; Takahashi, Ryoji Applied Catalysis A: General, Vol. 347, Issue 2 https://doi.org/10.1016/j.apcata.2008.06.013	journal	September 2008
Dehydration–hydrogenation of glycerol into 1,2-propanediol at ambient hydrogen pressure Akiyama, Masaki; Sato, Satoshi; Takahashi, Ryoji Applied Catalysis A: General, Vol. 371, Issue 1-2 https://doi.org/10.1016/j.apcata.2009.09.029	journal	December 2009
A review of catalytic issues and process conditions for renewable hydrogen and alkanes by aqueous-phase reforming of oxygenated hydrocarbons over supported metal catalysts Davda, R. R.; Shabaker, J. W.; Huber, G. W. Applied Catalysis B: Environmental, Vol. 56, Issue 1-2, p. 171-186 https://doi.org/10.1016/j.apcatb.2004.04.027	journal	March 2005
Selective hydrodeoxygenation of lignin model compound (3,4-dimethoxybenzyl alcohol) by Pd/CNX catalyst Zhang, Haichuan; Liu, Yang; Fu, Shiyu International Journal of Biological Macromolecules, Vol. 169 https://doi.org/10.1016/j.ijbiomac.2020.12.092	journal	February 2021
Elementary steps of syngas reactions on Mo2C(001): Adsorption thermochemistry and bond dissociation Medford, Andrew J.; Vojvodic, Aleksandra; Studt, Felix Journal of Catalysis, Vol. 290 https://doi.org/10.1016/j.jcat.2012.03.007	journal	June 2012
Reaction paths for hydrodeoxygenation of furfuryl alcohol at TiO2/Pd interfaces Deo, Shyam; Medlin, Will; Nikolla, Eranda Journal of Catalysis, Vol. 377 https://doi.org/10.1016/j.jcat.2019.07.012	journal	September 2019
Understanding the effect of Mo2C support on the activity of Cu for the hydrodeoxygenation of glycerol You, Kyung-Eun; Ammal, Salai C.; Lin, Zhexi Journal of Catalysis, Vol. 388 https://doi.org/10.1016/j.jcat.2020.05.007	journal	August 2020
Study on hydrodeoxygenation mechanism of anisole over Ni (111) by first-principles calculation Zhu, Chen; Cao, Jing-Pei; Yang, Zhen Molecular Catalysis, Vol. 523 https://doi.org/10.1016/j.mcat.2021.111402	journal	May 2022
Deoxygenation of glycolaldehyde and furfural on Mo 2 C/Mo(100) McManus, Jesse R.; Vohs, John M. Surface Science, Vol. 630 https://doi.org/10.1016/j.susc.2014.06.019	journal	December 2014
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
A Review of U.S. Patents in the Field of Organic Process Development Published During October to November 2014 Turner, Keith Organic Process Research & Development, Vol. 19, Issue 5 https://doi.org/10.1021/acs.oprd.5b00086	journal	April 2015
A Mechanistic Study of Polyol Hydrodeoxygenation over a Bifunctional Pt-WO _x /TiO ₂ Catalyst Stephens, Kyle J.; Allgeier, Alan M.; Bell, Alysha L. ACS Catalysis, Vol. 10, Issue 21 https://doi.org/10.1021/acscatal.0c03475	journal	October 2020
Catalyst Design for Selective Hydrodeoxygenation of Glycerol to 1,3-Propanediol Miao, Gai; Shi, Lei; Zhou, Zhimin ACS Catalysis, Vol. 10, Issue 24 https://doi.org/10.1021/acscatal.0c04167	journal	December 2020
Molybdenum-Catalyzed Conversion of Diols and Biomass-Derived Polyols to Alkenes Using Isopropyl Alcohol as Reductant and Solvent Dethlefsen, Johannes R.; Lupp, Daniel; Teshome, Ayele ACS Catalysis, Vol. 5, Issue 6 https://doi.org/10.1021/acscatal.5b00427	journal	May 2015
Chemical Titration and Transient Kinetic Studies of Site Requirements in Mo ₂ C-Catalyzed Vapor Phase Anisole Hydrodeoxygenation Lee, Wen-Sheng; Kumar, Anurag; Wang, Zhenshu ACS Catalysis, Vol. 5, Issue 7 https://doi.org/10.1021/acscatal.5b00713	journal	June 2015
Catalytic Conversion of Biomass into Chemicals and Fuels over Magnetic Catalysts Liu, Bing; Zhang, Zehui ACS Catalysis, Vol. 6, Issue 1 https://doi.org/10.1021/acscatal.5b02094	journal	December 2015
Highly Dispersed Copper over β-Mo ₂ C as an Efficient and Stable Catalyst for the Reverse Water Gas Shift (RWGS) Reaction Zhang, Xiao; Zhu, Xiaobing; Lin, Lili ACS Catalysis, Vol. 7, Issue 1 https://doi.org/10.1021/acscatal.6b02991	journal	December 2016
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
Recent Advances in Thermo-, Photo-, and Electrocatalytic Glycerol Oxidation Dodekatos, Georgios; Schünemann, Stefan; Tüysüz, Harun ACS Catalysis, Vol. 8, Issue 7 https://doi.org/10.1021/acscatal.8b01317	journal	May 2018
1,2-Propanediol as a Surrogate Molecule of Glycerol for Mechanistic Studies of Selective Hydrodeoxygenation Reactions over Mo ₂ C and Cu/Mo ₂ C Surfaces Lin, Zhexi; Wan, Weiming; Chen, Jingguang G. ACS Sustainable Chemistry & Engineering, Vol. 7, Issue 9 https://doi.org/10.1021/acssuschemeng.9b01051	journal	April 2019
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
DFT Study of Furfural Conversion to Furan, Furfuryl Alcohol, and 2-Methylfuran on Pd(111) Vorotnikov, Vassili; Mpourmpakis, Giannis; Vlachos, Dionisios G. ACS Catalysis, Vol. 2, Issue 12 https://doi.org/10.1021/cs300395a	journal	October 2012
Comparison of Tungsten and Molybdenum Carbide Catalysts for the Hydrodeoxygenation of Oleic Acid Hollak, Stefan A. W.; Gosselink, Robert W.; van Es, Daan S. ACS Catalysis, Vol. 3, Issue 12 https://doi.org/10.1021/cs400744y	journal	November 2013
Formation of C–C and C–O Bonds and Oxygen Removal in Reactions of Alkanediols, Alkanols, and Alkanals on Copper Catalysts Sad, María E.; Neurock, Matthew; Iglesia, Enrique Journal of the American Chemical Society, Vol. 133, Issue 50 https://doi.org/10.1021/ja207551f	journal	December 2011
Glycolaldehyde as a Probe Molecule for Biomass Derivatives: Reaction of C—OH and C═O Functional Groups on Monolayer Ni Surfaces Yu, Weiting; Barteau, Mark A.; Chen, Jingguang G. Journal of the American Chemical Society, Vol. 133, Issue 50 https://doi.org/10.1021/ja208786f	journal	December 2011
Microkinetic Simulation of Temperature-Programmed Desorption Wang, Chia-Ching; Wu, Jyun-Yi; Jiang, Jyh-Chiang The Journal of Physical Chemistry C, Vol. 117, Issue 12 https://doi.org/10.1021/jp309394p	journal	March 2013
Conformational Stability and Intramolecular Hydrogen Bonding in 1,2-Ethanediol and 1,4-Butanediol Das, Prasanta; Das, Puspendu K.; Arunan, E. The Journal of Physical Chemistry A, Vol. 119, Issue 16 https://doi.org/10.1021/jp512686s	journal	April 2015
Controlling reaction pathways of selective C–O bond cleavage of glycerol Wan, Weiming; Ammal, Salai C.; Lin, Zhexi Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-07047-7	journal	November 2018
Catalytic Hydrodeoxygenation of Bio-oil Model Compounds over Pt/HY Catalyst Lee, Heejin; Kim, Hannah; Yu, Mi Jin Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep28765	journal	June 2016
Adsorption and reaction of methanol on supported palladium catalysts: microscopic-level studies from ultrahigh vacuum to ambient pressure conditions Bäumer, Marcus; Libuda, Jörg; Neyman, Konstantin M. Phys. Chem. Chem. Phys., Vol. 9, Issue 27 https://doi.org/10.1039/B700365J	journal	January 2007
Bridging the pressure and material gap in heterogeneous catalysis: cobalt Fischer–Tropsch catalysts from surface science to industrial application Oosterbeek, Heiko Phys. Chem. Chem. Phys., Vol. 9, Issue 27 https://doi.org/10.1039/B703003G	journal	January 2007
Stability of intermediates in the glycerol hydrogenolysis on transition metal catalysts from first principles Coll, David; Delbecq, Françoise; Aray, Yosslen Phys. Chem. Chem. Phys., Vol. 13, Issue 4 https://doi.org/10.1039/C0CP00858C	journal	January 2011
A computational analysis of intramolecularity in proton transfer reactions Karaman, Rafik; Pascal, Robert Organic & Biomolecular Chemistry, Vol. 8, Issue 22 https://doi.org/10.1039/c0ob00252f	journal	January 2010
Transformations of biomass-derived platform molecules: from high added-value chemicals to fuels via aqueous-phase processing Serrano-Ruiz, Juan Carlos; Luque, Rafael; Sepúlveda-Escribano, Antonio Chemical Society Reviews, Vol. 40, Issue 11, p. 5266-5281 https://doi.org/10.1039/c1cs15131b	journal	January 2011
Improved tangent estimate in the nudged elastic band method for finding minimum energy paths and saddle points Henkelman, Graeme; Jónsson, Hannes The Journal of Chemical Physics, Vol. 113, Issue 22 https://doi.org/10.1063/1.1323224	journal	December 2000
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
Optimization methods for finding minimum energy paths Sheppard, Daniel; Terrell, Rye; Henkelman, Graeme The Journal of Chemical Physics, Vol. 128, Issue 13 https://doi.org/10.1063/1.2841941	journal	April 2008
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Simplified method for calculating the energy of weakly interacting fragments Harris, J. Physical Review B, Vol. 31, Issue 4 https://doi.org/10.1103/PhysRevB.31.1770	journal	February 1985
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
Ab initio molecular-dynamics simulation of the liquid-metal–amorphous-semiconductor transition in germanium Kresse, G.; Hafner, J. Physical Review B, Vol. 49, Issue 20, p. 14251-14269 https://doi.org/10.1103/PhysRevB.49.14251	journal	May 1994
Projector augmented-wave method Blöchl, P. E. Physical Review B, Vol. 50, Issue 24, p. 17953-17979 https://doi.org/10.1103/PhysRevB.50.17953	journal	December 1994
Periodic boundary conditions in ab initio calculations Makov, G.; Payne, M. C. Physical Review B, Vol. 51, Issue 7 https://doi.org/10.1103/PhysRevB.51.4014	journal	February 1995
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
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
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Platinum-Like Behavior of Tungsten Carbide in Surface Catalysis Levy, R. B.; Boudart, M. Science, Vol. 181, Issue 4099 https://doi.org/10.1126/science.181.4099.547	journal	August 1973
Solving Index-1 DAEs in MATLAB and Simulink Shampine, Lawrence F.; Reichelt, Mark W.; Kierzenka, Jacek A. SIAM Review, Vol. 41, Issue 3 https://doi.org/10.1137/S003614459933425X	journal	January 1999
The MATLAB ODE Suite Shampine, Lawrence F.; Reichelt, Mark W. SIAM Journal on Scientific Computing, Vol. 18, Issue 1 https://doi.org/10.1137/S1064827594276424	journal	January 1997
Transition State Theory Pechukas, P. Annual Review of Physical Chemistry, Vol. 32, Issue 1 https://doi.org/10.1146/annurev.pc.32.100181.001111	journal	October 1981
Selective Conversion of Glycerol into 1,2-Propanediol at Ambient Hydrogen Pressure Sato, Satoshi; Akiyama, Masaki; Inui, Kanichiro Chemistry Letters, Vol. 38, Issue 6 https://doi.org/10.1246/cl.2009.560	journal	June 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

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