Reaction pathways of furfural, furfuryl alcohol and 2-methylfuran on Cu(111) and NiCu bimetallic surfaces

Xiong, Ke; Wan, Weiming; Chen, Jingguang G.

doi:10.1016/j.susc.2016.02.011

Title: Reaction pathways of furfural, furfuryl alcohol and 2-methylfuran on Cu(111) and NiCu bimetallic surfaces

Journal Article · Tue Feb 23 00:00:00 EST 2016 · Surface Science

DOI:https://doi.org/10.1016/j.susc.2016.02.011· OSTI ID:1338591

Xiong, Ke ^[1]; Wan, Weiming ^[2]; Chen, Jingguang G. ^[3]

Univ. of Delaware, Newark, DE (United States). Dept. of Chemical and Biomolecular Engineering
Columbia Univ., New York, NY (United States). Dept. of Chemical Engineering
Columbia Univ., New York, NY (United States). Dept. of Chemical Engineering; Brookhaven National Lab. (BNL), Upton, NY (United States). Dept. of Chemistry

Hydrodeoxygenation (HDO) is an important reaction for converting biomass-derived furfural to value-added 2-methylfuran, which is a promising fuel additive. In this work, the HDO of furfural to produce 2-methylfuran occurred on the NiCu bimetallic surfaces prepared on either Ni(111) or Cu(111). The reaction pathways of furfural were investigated on Cu(111) and Ni/Cu(111) surfaces using density functional theory (DFT) calculations, temperature programmed desorption (TPD) and high resolution electron energy loss spectroscopy (HREELS) experiments. These studies provided mechanistic insights into the effects of bimetallic formation on enhancing the HDO activity. Specifically, furfural weakly adsorbed on Cu(111), while it strongly adsorbed on Ni/Cu(111) through an η²(C,O) configuration which led to the HDO of furfural on Ni/Cu(111). Lastly, the ability to dissociate H₂ on Ni/Cu(111) is also an important factor for enhancing the HDO activity over Cu(111).

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Research Organization:: Brookhaven National Lab. (BNL), Upton, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0012704; AC02-98CH10886; 13-038

OSTI ID:: 1338591

Alternate ID(s):: OSTI ID: 1359910

Report Number(s):: BNL-112731-2016-JA

Journal Information:: Surface Science, Vol. 652, Issue C; ISSN 0039-6028

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 59 works

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References (30)

Conversion of Biorenewable Feedstocks: New Challenges in Heterogeneous Catalysis Shanks, Brent H. Industrial & Engineering Chemistry Research, Vol. 49, Issue 21 https://doi.org/10.1021/ie100487r	journal	November 2010
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
Chemical Routes for the Transformation of Biomass into Chemicals Corma, Avelino; Iborra, Sara; Velty, Alexandra Chemical Reviews, Vol. 107, Issue 6, p. 2411-2502 https://doi.org/10.1021/cr050989d	journal	June 2007
Recent Advances in Hydrotreating of Pyrolysis Bio-Oil and Its Oxygen-Containing Model Compounds Wang, Huamin; Male, Jonathan; Wang, Yong ACS Catalysis, Vol. 3, Issue 5 https://doi.org/10.1021/cs400069z	journal	April 2013
Selective Hydrodeoxygenation of Biomass-Derived Oxygenates to Unsaturated Hydrocarbons using Molybdenum Carbide Catalysts Ren, Hui; Yu, Weiting; Salciccioli, Michael ChemSusChem, Vol. 6, Issue 5 https://doi.org/10.1002/cssc.201200991	journal	April 2013
Furfural-A Promising Platform for Lignocellulosic Biofuels Lange, Jean-Paul; van der Heide, Evert; van Buijtenen, Jeroen ChemSusChem, Vol. 5, Issue 1 https://doi.org/10.1002/cssc.201100648	journal	December 2011
Production of 2-Methylfuran by Vapor-Phase Hydrogenation of Furfural Burnett, L. W.; Johns, I. B.; Holdren, R. F. Industrial & Engineering Chemistry, Vol. 40, Issue 3 https://doi.org/10.1021/ie50459a034	journal	March 1948
Reactions of Furan Compounds. XI. Side Chain Reactions of Furfural and Furfuryl Alcohol over Nickel-Copper and Iron-Copper Catalysts ¹ Lukes, Robert M.; Wilson, Christopher L. Journal of the American Chemical Society, Vol. 73, Issue 10 https://doi.org/10.1021/ja01154a093	journal	October 1951
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
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 conversion of furfural to methylfuran over silica-supported NiFe bimetallic catalysts Sitthisa, Surapas; An, Wei; Resasco, Daniel E. Journal of Catalysis, Vol. 284, Issue 1 https://doi.org/10.1016/j.jcat.2011.09.005	journal	November 2011
Selective deoxygenation of aldehydes and alcohols on molybdenum carbide (Mo 2 C) surfaces Xiong, Ke; Yu, Weiting; Chen, Jingguang G. Applied Surface Science, Vol. 323 https://doi.org/10.1016/j.apsusc.2014.06.100	journal	December 2014
Vapor phase hydrodeoxygenation of furfural to 2-methylfuran on molybdenum carbide catalysts Lee, Wen-Sheng; Wang, Zhenshu; Zheng, Weiqing Catalysis Science & Technology, Vol. 4, Issue 8 https://doi.org/10.1039/c4cy00286e	journal	January 2014
Acid and base characteristics of molybdenum carbide catalysts Bej, Shyamal K.; Bennett, Christopher A.; Thompson, Levi T. Applied Catalysis A: General, Vol. 250, Issue 2 https://doi.org/10.1016/S0926-860X(02)00664-6	journal	September 2003
Catalytic Reduction of Biomass-Derived Furanic Compounds with Hydrogen Nakagawa, Yoshinao; Tamura, Masazumi; Tomishige, Keiichi ACS Catalysis, Vol. 3, Issue 12 https://doi.org/10.1021/cs400616p	journal	October 2013
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
Theoretical and experimental studies of the adsorption geometry and reaction pathways of furfural over FeNi bimetallic model surfaces and supported catalysts Yu, Weiting; Xiong, Ke; Ji, Na Journal of Catalysis, Vol. 317 https://doi.org/10.1016/j.jcat.2014.06.025	journal	August 2014
Development of NiCu Catalysts for Aqueous-Phase Hydrodeoxygenation Dickinson, Jacob G.; Savage, Phillip E. ACS Catalysis, Vol. 4, Issue 8 https://doi.org/10.1021/cs500562u	journal	July 2014
Stability and activity of Pt and Ni catalysts for hydrodeoxygenation in supercritical water Dickinson, Jacob G.; Savage, Phillip E. Journal of Molecular Catalysis A: Chemical, Vol. 388-389 https://doi.org/10.1016/j.molcata.2013.08.003	journal	July 2014
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
Monolayer bimetallic surfaces: Experimental and theoretical studies of trends in electronic and chemical properties Chen, Jingguang G.; Menning, Carl A.; Zellner, Michael B. Surface Science Reports, Vol. 63, Issue 5 https://doi.org/10.1016/j.surfrep.2008.02.001	journal	May 2008
Elastic Scattering Corrections in AES and XPS. II. Estimating Attenuation Lengths and Conditions Required for their Valid Use in Overlayer/Substrate Experiments Cumpson, P. J.; Seah, M. P. Surface and Interface Analysis, Vol. 25, Issue 6 https://doi.org/10.1002/(SICI)1096-9918(199706)25:6<430::AID-SIA254>3.0.CO;2-7	journal	June 1997
Reaction Pathways of Propanal and 1-Propanol on Fe/Ni(111) and Cu/Ni(111) Bimetallic Surfaces Myint, MyatNoeZin; Yan, Yushan; Chen, Jingguang G. The Journal of Physical Chemistry C, Vol. 118, Issue 21 https://doi.org/10.1021/jp501208q	journal	May 2014
The growth of thin Cu layers on Ni(111) studied by CO titration and photoelectron spectroscopy Koschel, H.; Held, G.; Steinrück, H. -P Surface Science, Vol. 453, Issue 1-3 https://doi.org/10.1016/S0039-6028(00)00349-6	journal	May 2000
A vibrational and TDS study of the adsorption of pyrrole, furan and thiophene on Cu(100): Evidence for π-bonded and inclined species Sexton, B. A. Surface Science, Vol. 163, Issue 1 https://doi.org/10.1016/0039-6028(85)90851-9	journal	November 1985
Adsorption and Reaction of Furfural and Furfuryl Alcohol on Pd(111): Unique Reaction Pathways for Multifunctional Reagents Pang, Simon H.; Medlin, J. Will ACS Catalysis, Vol. 1, Issue 10 https://doi.org/10.1021/cs200226h	journal	August 2011
The structure of CO on Ni(111) Netzer, Falko P.; Madey, Theodore E. The Journal of Chemical Physics, Vol. 76, Issue 1 https://doi.org/10.1063/1.442674	journal	January 1982
Vibrational properties of levulinic acid and furan derivatives: Raman spectroscopy and theoretical calculations Kim, Taejin; Assary, Rajeev S.; Curtiss, Larry A. Journal of Raman Spectroscopy, Vol. 42, Issue 12 https://doi.org/10.1002/jrs.2951	journal	May 2011
Oxidative coupling and ring opening of furan on silver(110): formation of maleic anhydride, benzene, and bifuran Crew, William W.; Madix, Robert J. Journal of the American Chemical Society, Vol. 115, Issue 2 https://doi.org/10.1021/ja00055a050	journal	January 1993
Deoxygenation of Biomass-Derived Oxygenates: Reaction of Furfural on Zn-Modified Pt(111) Shi, Daming; Vohs, John M. ACS Catalysis, Vol. 5, Issue 4 https://doi.org/10.1021/acscatal.5b00038	journal	March 2015

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Lignocellulosic Biomass Transformations via Greener Oxidative Pretreatment Processes: Access to Energy and Value-Added Chemicals Den, Walter; Sharma, Virender K.; Lee, Mengshan Frontiers in Chemistry, Vol. 6 https://doi.org/10.3389/fchem.2018.00141	journal	April 2018
Ring‐Opening Reaction of Furfural and Tetrahydrofurfuryl Alcohol on Hydrogen‐Predosed Iridium(1 1 1) and Cobalt/Iridium(1 1 1) Surfaces Wan, Weiming; Jenness, Glen R.; Xiong, Ke ChemCatChem, Vol. 9, Issue 9 https://doi.org/10.1002/cctc.201601646	journal	March 2017
Spectroscopic characterization of a highly selective NiCu ₃ /C hydrodeoxygenation catalyst Goulas, Konstantinos A.; Lee, Jennifer D.; Zheng, Weiqing Catalysis Science & Technology, Vol. 8, Issue 23 https://doi.org/10.1039/c8cy01280f	journal	January 2018

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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NiCu bimetallic
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Title: Reaction pathways of furfural, furfuryl alcohol and 2-methylfuran on Cu(111) and NiCu bimetallic surfaces

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