Surface Reactions of Dicyclohexylmethane on Pt(111)

Journal of Physical Chemistry C

Volumn 119, Issue 35, 2015, Pages 20299-20311

  Gleichweit, Christoph ^a   Amende, Max ^a   Höfert, Oliver ^a   Xu, Tao ^a   Späth, Florian ^a   Brückner, Nicole ^a   Wasserscheid, Peter ^a,b   Libuda, Jörg ^a   Steinrück, Hans Peter ^a   Papp, Christian ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; DESORPTION; HYDROGEN; HYDROGEN STORAGE; MOLECULES; PLATINUM; SURFACE REACTIONS; TEMPERATURE PROGRAMMED DESORPTION; X RAY ABSORPTION;

DIPHENYLMETHANE; HYDROGEN CARRIERS; HYDROGEN DESORPTION; INFRARED REFLECTION ABSORPTION SPECTROSCOPY; METHYLCYCLOHEXANE; METHYLENE GROUPS; MOLECULAR FRAGMENTS; NEAR EDGE X-RAY ABSORPTION FINE STRUCTURES;

X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 84940864640     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/acs.jpcc.5b06178     Document Type: Article

References (59)

1. Stanislaus, A.; Cooper, B. H. Aromatic Hydrogenation Catalysis: A Review Catal. Rev.: Sci. Eng. 1994, 36, 75-123 10.1080/01614949408013921
2. Satterfield, C. N. Heterogeneous Catalysis in Industrial Practice; Krieger: Malabar, FL, 1996.
3. Moser, M.; Sadler, C. C., Reforming-Industrial. In Encyclopedia of Catalysis; Horvath, I. T., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2002.
4. Scherer, G. W. H.; Newson, E. Analysis of the Seasonal Energy Storage of Hydrogen in Liquid Organic Hydrides Int. J. Hydrogen Energy 1998, 23, 19-25 10.1016/S0360-3199(97)00018-9
5. Zhao, H. Y.; Oyama, S. T.; Naeemi, E. D. Hydrogen Storage by Using Heterocyclic Compounds: The Hydrogenation of 2-Methylthiophene Catal. Today 2010, 149, 172-184 10.1016/j.cattod.2009.02.039
6. Crabtree, R. H. Hydrogen Storage in Liquid Organic Heterocycles Energy Environ. Sci. 2008, 1, 134-138 10.1039/b805644g
7. Teichmann, D.; Arlt, W.; Wasserscheid, P.; Freymann, R. A Future Energy Supply Based on Liquid Organic Hydrogen Carriers (Lohc) Energy Environ. Sci. 2011, 4, 2767-2773 10.1039/c1ee01454d
8. Brückner, N.; Obesser, K.; Bösmann, A.; Teichmann, D.; Arlt, W.; Dungs, J.; Wasserscheid, P. Evaluation of Industrially Applied Heat-Transfer Fluids as Liquid Organic Hydrogen Carrier Systems ChemSusChem 2014, 7, 229-235 10.1002/cssc.201300426
9. Teichmann, D.; Stark, K.; Muller, K.; Zottl, G.; Wasserscheid, P.; Arlt, W. Energy Storage in Residential and Commercial Buildings Via Liquid Organic Hydrogen Carriers (Lohc) Energy Environ. Sci. 2012, 5, 9044-9054 10.1039/c2ee22070a
10. Teichmann, D.; Arlt, W.; Wasserscheid, P. Liquid Organic Hydrogen Carriers as an Efficient Vector for the Transport and Storage of Renewable Energy Int. J. Hydrogen Energy 2012, 37, 18118 10.1016/j.ijhydene.2012.08.066
11. Amende, M. et al. Dehydrogenation Mechanism of Liquid Organic Hydrogen Carriers: Dodecahydro-N-Ethylcarbazole on Pd(111) Chem.-Eur. J. 2013, 19, 10854-10865 10.1002/chem.201301323
12. Sobota, M. et al. Dehydrogenation of Dodecahydro-N-Ethylcarbazole on Pd/Al2o3 Model Catalysts Chem.-Eur. J. 2011, 17, 11542-11552 10.1002/chem.201101311
13. Amende, M. et al. Size and Structure Effects Controlling the Stability of the Liquid Organic Hydrogen Carrier Dodecahydro- N -Ethylcarbazole During Dehydrogenation over Pt Model Catalysts J. Phys. Chem. Lett. 2014, 5, 1498-1504 10.1021/jz500157r
14. Amende, M. et al. Model Catalytic Studies of Liquid Organic Hydrogen Carriers: Dehydrogenation and Decomposition Mechanisms of Dodecahydro-N-Ethylcarbazole on Pt(111) ACS Catal. 2014, 4, 657-665 10.1021/cs400946x
15. Gleichweit, C. et al. Alkyl Chain Length-Dependent Surface Reaction of Dodecahydro-N-Alkylcarbazoles on Pt Model Catalysts J. Chem. Phys. 2014, 140, 204711 10.1063/1.4875921
16. Gleichweit, C. et al. Dehydrogenation of Dodecahydro-N-Ethylcarbazole on Pt(111) ChemSusChem 2013, 6, 974-977 10.1002/cssc.201300263
17. Okada, Y.; Sasaki, E.; Watanabe, E.; Hyodo, S.; Nishijima, H. Development of Dehydrogenation Catalyst for Hydrogen Generation in Organic Chemical Hydride Method Int. J. Hydrogen Energy 2006, 31, 1348-1356 10.1016/j.ijhydene.2005.11.014
18. Zhang, R. et al. Integrated X-Ray Photoelectron Spectroscopy and Dft Characterization of Benzene Adsorption on Pt(111), Pt(355) and Pt(322) Surfaces Phys. Chem. Chem. Phys. 2013, 15, 20662-20671 10.1039/c3cp53127a
19. Campbell, J. M.; Seimanides, S.; Campbell, C. T. Probing Ensemble Effects in Surface-Reactions 0.2. Benzene Adsorption on Clean and Bismuth-Covered Pt(111) J. Phys. Chem. 1989, 93, 815-826 10.1021/j100339a057
20. Abon, M.; Bertolini, J. C.; Billy, J.; Massardier, J.; Tardy, B. Adsorption States of Benzene and Toluene on Pt(111)-a Vibrational Eels, Delta-Phi, Aes and Tds Study Surf. Sci. 1985, 162, 395-401 10.1016/0039-6028(85)90926-4
21. Land, D. P.; Erley, W.; Ibach, H. Hreels Investigation of the Orientation and Dehydrogenation of Cyclohexane on Pt[111] Surf. Sci. 1993, 289, 237-246 10.1016/0039-6028(93)90656-5
22. Bussell, M. E.; Henn, F. C.; Campbell, C. T. A Bptds and Hreels Study of the Interaction of Cyclohexane with the Pt(111) Surface J. Phys. Chem. 1992, 96, 5978-5982 10.1021/j100193a061
23. Newton, M. A.; Campbell, C. T. Applications of Bptds in the Kinetics and Mechanisms of Hydrocarbon Conversion Reactions on Pt(111): Methylcyclohexane Dehydrogenation Z. Phys. Chem. 1997, 198, 169-187 10.1524/zpch.1997.198.Part-1-2.169
24. Rodriguez, J. A.; Campbell, C. T. Probing Ensemble Effects in Surface-Reactions 0.3. Cyclohexane Adsorption on Clean and Bismuth-Covered Pt(111) J. Phys. Chem. 1989, 93, 826-835 10.1021/j100339a058
25. Li, G.; Yada, K.; Kanezashi, M.; Yoshioka, T.; Tsuru, T. Methylcyclohexane Dehydrogenation in Catalytic Membrane Reactors for Efficient Hydrogen Production Ind. Eng. Chem. Res. 2013, 52, 13325-13332 10.1021/ie401306q
26. Kreuder, H.; Müller, C.; Meier, J.; Gerhards, U.; Dittmeyer, R.; Pfeifer, P. Catalyst Development for the Dehydrogenation of Mch in a Microstructured Membrane Reactor-for Heat Storage by a Liquid Organic Reaction Cycle Catal. Today 2014, 242, 211 10.1016/j.cattod.2014.06.029
27. Emori, H.; Kawamura, T.; Ishikawa, T.; Takamura, T. Carbon-Hydride Energy Storage System. Hitachi Review 2013, 62, 192-198.
28. Xu, C.; Koel, B. E.; Newton, M. A.; Frei, N. A.; Campbell, C. T. Dehydrogenation of Methylcyclohexane on Pt(111) J. Phys. Chem. 1995, 99, 16670-16675 10.1021/j100045a029
29. Domagala, M. E.; Campbell, C. T. Identification of Adsorbed Benzyl on Pt(111) Using D2-Btpds Langmuir 1994, 10, 2636-2639 10.1021/la00020a023
30. Steinrück, H. P.; Fuhrmann, T.; Papp, C.; Tränkenschuh, B.; Denecke, R. A Detailed Analysis of Vibrational Excitations in X-Ray Photoelectron Spectra of Adsorbed Small Hydrocarbons J. Chem. Phys. 2006, 125, 204706 10.1063/1.2397678
31. Avery, N. R. Identification of a Novel [Small Pi]+[Sigma] Bonded [Small Eta]7-Benzyl Species from Toluene Adsorption on Pt(111) at 350 K J. Chem. Soc., Chem. Commun. 1988, 153-154 10.1039/c39880000153
32. Johnson, A. L.; Muetterties, E. L.; Stöhr, J. Orientation of Complex Molecules Chemisorbed on Metal Surfaces: Near-Edge X-Ray Absorption Studies J. Am. Chem. Soc. 1983, 105, 7183-7185 10.1021/ja00362a034
33. Yang, M.; Chou, K. C.; Somorjai, G. A. The Structures and Reactions of Linear and Cyclic C6 Hydrocarbons Adsorbed on the Pt(111) Crystal Surface Studied by Sum Frequency Generation Vibrational Spectroscopy: Pressure, Temperature, and H2 Coadsorption Effects J. Phys. Chem. B 2004, 108, 14766-14779 10.1021/jp048238n
34. Hähner, G. Near Edge X-Ray Absorption Fine Structure Spectroscopy as a Tool to Probe Electronic and Structural Properties of Thin Organic Films and Liquids Chem. Soc. Rev. 2006, 35, 1244-1255 10.1039/b509853j
35. Hitchcock, A. P.; Newbury, D. C.; Ishii, I.; Stöhr, J.; Horsley, J. A.; Redwing, R. D.; Johnson, A. L.; Sette, F. Carbon K-Shell Excitation of Gaseous and Condensed Cyclic Hydrocarbons: C3h6, C4h8, C5h8, C5h10, C6h10, C6h12, and C8h8 J. Chem. Phys. 1986, 85, 4849-4862 10.1063/1.451719
36. Püttner, R.; Kolczewski, C.; Martins, M.; Schlachter, A. S.; Snell, G.; Sant'Anna, M.; Viefhaus, J.; Hermann, K.; Kaindl, G. The C 1s Nexafs Spectrum of Benzene Below Threshold: Rydberg or Valence Character of the Unoccupied Σ-Type Orbitals Chem. Phys. Lett. 2004, 393, 361-366 10.1016/j.cplett.2004.06.053
37. Joseph, Y.; Wuhn, M.; Niklewski, A.; Ranke, W.; Weiss, W.; Woll, C.; Schlogl, R. Interaction of Ethylbenzene and Styrene with Iron Oxide Model Catalyst Films at Low Coverages: A Nexafs Study Phys. Chem. Chem. Phys. 2000, 2, 5314-5319 10.1039/b006332k
38. Hitchcock, A. P.; Ishii, I. Carbon K-Shell Excitation Spectra of Linear and Branched Alkanes J. Electron Spectrosc. Relat. Phenom. 1987, 42, 11-26 10.1016/0368-2048(87)85002-8
39. Horsley, J. A.; Stöhr, J.; Hitchcock, A. P.; Newbury, D. C.; Johnson, A. L.; Sette, F. Resonances in the K Shell Excitation Spectra of Benzene and Pyridine: Gas Phase, Solid, and Chemisorbed States J. Chem. Phys. 1985, 83, 6099 10.1063/1.449601
40. Domagala, M. E.; Campbell, C. T. The Chemistry of Bibenzyl on Pt(111) as Probed with Bptds Surf. Sci. 1994, 301, 151-164 10.1016/0039-6028(94)91296-3
41. Chesters, M. A.; Gardner, P. The Infrared Spectrum of Cyclohexane Adsorbed on Pt(111) Spectrochim. Acta, Part A 1990, 46, 1011-1016 10.1016/0584-8539(90)80018-T
42. Chesters, M. A.; Parker, S. F.; Raval, R. Cyclohexane Adsorption on Cu(111) Studied by Infrared and Electron Energy Loss Spectroscopy J. Electron Spectrosc. Relat. Phenom. 1986, 39, 155-162 10.1016/0368-2048(86)85043-5
43. Wiberg, K. B.; Shrake, A. A Vibrational Study of Cyclohexane and Some of Its Isotopic Derivatives-I. Raman and Infrared Spectra and Assignments of Cyclohexaae and Cyclohexane-D12 Spectrochim. Acta, Part A 1971, 27, 1139-1151 10.1016/0584-8539(71)80196-4
44. Manner, W. L.; Girolami, G. S.; Nuzzo, R. G. Sequential Dehydrogenation of Unsaturated Cyclic C5 and C6 Hydrocarbons on Pt(111) J. Phys. Chem. B 1998, 102, 10295-10306 10.1021/jp9830272
45. Hoffmann, F. M. Infrared Reflection-Absorption Spectroscopy of Adsorbed Molecules Surf. Sci. Rep. 1983, 3 (107) 109-192 10.1016/0167-5729(83)90001-8
46. Poelsema, B.; Lenz, K.; Comsa, G. The Dissociative Adsorption of Hydrogen on Defect-'Free' Pt(111) J. Phys.: Condens. Matter 2010, 22, 304006 10.1088/0953-8984/22/30/304006
47. Denecke, R.; Kinne, M.; Whelan, C. M.; Steinrück, H.-P. In-Situ Core-Level Photoelectron Spectroscopy of Adsorbates on Surfaces Involving a Molecular Beam-General Setup and First Experiments Surf. Rev. Lett. 2002, 9, 797 10.1142/S0218625X0200297X
48. Kinne, M.; Fuhrmann, T.; Zhu, J. F.; Whelan, C. M.; Denecke, R.; Steinrück, H.-P. Kinetics of the Co Oxidation Reaction on Pt(111) Studied by in Situ High-Resolution X-Ray Photoelectron Spectroscopy J. Chem. Phys. 2004, 120, 7113-7122 10.1063/1.1669378
49. McEwen, J. S.; Payne, S. H.; Kreuzer, H. J.; Kinne, M.; Denecke, R.; Steinrück, H. P. Adsorption and Desorption of Co on Pt(111): A Comprehensive Analysis Surf. Sci. 2003, 545, 47-69 10.1016/j.susc.2003.08.040
50. Tränkenschuh, B.; Fritsche, N.; Fuhrmann, T.; Papp, C.; Zhu, J. F.; Denecke, R.; Steinrück, H.-P. A Site-Selective in Situ Study of Co Adsorption and Desorption on Pt(355) J. Chem. Phys. 2006, 124, 074712 10.1063/1.2168441
51. Trankenschuh, B.; Papp, C.; Fuhrmann, T.; Denecke, R.; Steinruck, H. P. The Dissimilar Twins-a Comparative, Site-Selective in Situ Study of Co Adsorption and Desorption on Pt(322) and Pt(355) Surf. Sci. 2007, 601, 1108-1117 10.1016/j.susc.2006.12.004
52. Stöhr, J. Nexafs Spectroscopy; Springer: Berlin, 1992; p 158.
53. Held, G.; Uremović, S.; Stellwag, C.; Menzel, D. A Low-Energy Electron Diffraction Data Acquisition System for Very Low Electron Doses Based Upon a Slow Scan Charge Coupled Device Camera Rev. Sci. Instrum. 1996, 67, 378-383 10.1063/1.1146599
54. Braun, W.; Steinrück, H. P.; Held, G. The Surface Geometry of Carbonmonoxide and Hydrogen Co-Adsorbed on Ni{1 1 1} Surf. Sci. 2005, 574, 193-204 10.1016/j.susc.2004.10.029
55. Feulner, P.; Menzel, D. Simple Ways to Improve "Flash Desorption" Measurements from Single Crystal Surfaces J. Vac. Sci. Technol. 1980, 17, 662-663 10.1116/1.570537
56. Desikusumastuti, A.; Staudt, T.; Happel, M.; Laurin, M.; Libuda, J. Adsorption and Reaction of No2 on Ordered Alumina Films and Mixed Baria-Alumina Nanoparticles: Cooperative Versus Non-Cooperative Reaction Mechanisms J. Catal. 2008, 260, 315-328 10.1016/j.jcat.2008.09.020
57. Kleyn, A. W. Molecular Beams and Chemical Dynamics at Surfaces Chem. Soc. Rev. 2003, 32, 87-95 10.1039/b105760j
58. Libuda, J.; Freund, H. J. Molecular Beam Experiments on Model Catalysts Surf. Sci. Rep. 2005, 57, 157-298 10.1016/j.surfrep.2005.03.002
59. Libuda, J.; Freund, H. J. Reaction Kinetics on Complex Model Catalysts under Single Scattering Conditions J. Phys. Chem. B 2002, 106, 4901-4915 10.1021/jp014055e