Selective propane dehydrogenation with single-site CoII on SiO2 by a non-redox mechanism

Journal of Catalysis

Volumn 322, Issue , 2015, Pages 24-37

  Hu, Bo ^a,b   Bean Getsoian, Andrew ^a   Schweitzer, Neil M ^a,c   Das, Ujjal ^a   Kim, Hacksung ^a,c   Niklas, Jens ^a   Poluektov, Oleg ^a   Curtiss, Larry A ^a   Stair, Peter C ^a,c   Miller, Jeffrey T ^a   Hock, Adam S ^a,b  

^a ARGONNE NATIONAL LABORATORY   (United States)

^b ILLINOIS INSTITUTE OF TECHNOLOGY   (United States)

^c NORTHWESTERN UNIVERSITY   (United States)

Author keywords

Dehydrogenation; EXAFS; Lewis acid; Raman spectroscopy; Single site catalysis

Indexed keywords

ABSORPTION SPECTROSCOPY; CATALYST ACTIVITY; DEHYDROGENATION; PARAMAGNETIC RESONANCE; PROPANE; RAMAN SPECTROSCOPY; SILICA;

ABSORPTION FINE STRUCTURE; CATALYTIC PERFORMANCE; EXAFS; HYBRID DENSITY FUNCTIONAL THEORY; LEWIS ACID; PROPANE DEHYDROGENATION; SINGLE-SITE CATALYSIS; SPECTROSCOPIC CHARACTERIZATION;

DENSITY FUNCTIONAL THEORY;

EID: 84919400958     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2014.10.018     Document Type: Article

References (77)

1. Y. Li, S. Yu, X. Wu, J. Xiao, W. Shen, Z. Dong, and J. Gao Iron catalyzed asymmetric hydrogenation of ketones J. Am. Chem. Soc. 136 2014 4031 4039
2. V. Lyaskovskyy, A.I.O. Suarez, H. Lu, H. Jiang, X.P. Zhang, and B. de Bruin Mechanism of cobalt(II) porphyrin-catalyzed C-H amination with organic azides: radical nature and H-atom abstraction ability of the key cobalt(III)-nitrene intermediates J. Am. Chem. Soc. 133 2011 12264 12273
3. H. Lu, V. Subbarayan, J. Tao, and X.P. Zhang Cobalt(II)-catalyzed intermolecular benzylic C-H amination with 2,2,2-trichloroethoxycarbonyl azide (TrocN3) Organometallics 29 2009 389 393
4. W.I. Dzik, X. Xu, X.P. Zhang, J.N.H. Reek, and B. de Bruin 'Carbene radicals' in CoII(por)-catalyzed olefin cyclopropanation J. Am. Chem. Soc. 132 2010 10891 10902
5. M.R. Friedfeld, G.W. Margulieux, B.A. Schaefer, and P.J. Chirik Bis(phosphine)cobalt dialkyl complexes for directed catalytic alkene hydrogenation J. Am. Chem. Soc. 2014
6. R.P. Yu, J.M. Darmon, C. Milsmann, G.W. Margulieux, S.C.E. Stieber, S. DeBeer, and P.J. Chirik Catalytic hydrogenation activity and electronic structure determination of bis(arylimidazol-2-ylidene)pyridine cobalt alkyl and hydride complexes J. Am. Chem. Soc. 135 2013 13168 13184
7. K. Gao, and N. Yoshikai Low-valent cobalt catalysis: new opportunities for C-H functionalization Acc. Chem. Res. 47 2014 1208 1219
8. C.C. Hojilla Atienza, C. Milsmann, S.P. Semproni, Z.R. Turner, and P.J. Chirik Reversible carbon-carbon bond formation induced by oxidation and reduction at a redox-active cobalt complex Inorg. Chem. 52 2013 5403 5417
9. C.C.H. Atienza, T. Diao, K.J. Weller, S.A. Nye, K.M. Lewis, J.G.P. Delis, J.L. Boyer, A.K. Roy, and P.J. Chirik Bis(imino)pyridine cobalt-catalyzed dehydrogenative silylation of alkenes: scope, mechanism, and origins of selective allylsilane formation J. Am. Chem. Soc. 136 2014 12108 12118
10. J.V. Obligacion, and P.J. Chirik Bis(imino)pyridine cobalt-catalyzed alkene isomerization-hydroboration: a strategy for remote hydrofunctionalization with terminal selectivity J. Am. Chem. Soc. 135 2013 19107 19110
11. J.V. Obligacion, S.P. Semproni, and P.J. Chirik Cobalt-catalyzed C-H borylation J. Am. Chem. Soc. 136 2014 4133 4136
12. G. Hilt, A. Paul, and J. Treutwein Cobalt catalysis at the crossroads: cobalt-catalyzed alder-ene reaction versus [2 + 2] cycloaddition Org. Lett. 12 2010 1536 1539
13. Z. Yang, H. Yu, and Y. Fu Mechanistic study on ligand-controlled cobalt-catalyzed regioselectivity-switchable hydroarylation of styrenes Chem. - Eur. J. 19 2013 12093 12103
14. J.J.H.B. Sattler, J. Ruiz-Martinez, E. Santillan-Jimenez, and B.M. Weckhuysen Catalytic dehydrogenation of light alkanes on metals and metal oxides Chem. Rev. 2014
15. G.Q. Zhang, and S.K. Hanson Cobalt-catalyzed acceptorless alcohol dehydrogenation: synthesis of imines from alcohols and amines Org. Lett. 15 2013 650 653
16. G.Q. Zhang, B.L. Scott, and S.K. Hanson Mild and homogeneous cobalt-catalyzed hydrogenation of C=C, C=O, and C=N bonds Angew. Chem., Int. Ed. 51 2012 12102 12106
17. Z.B. Mo, D.K. Chen, X.B. Leng, and L. Deng Intramolecular C(sp(3))-H bond activation reactions of low-valent cobalt complexes with coordination unsaturation Organometallics 31 2012 7040 7043
18. S.Y. Yu, G.J. Yu, W. Li, and E. Iglesia Kinetics and reaction pathways for propane dehydrogenation and aromatization on Co/H-ZSM5 and H-ZSM5 J. Phys. Chem. B 106 2002 4714 4720
19. W. Li, S.Y. Yu, G.D. Meitzner, and E. Iglesia Structure and properties of cobalt-exchanged H-ZSM5 catalysts for dehydrogenation and dehydrocyclization of alkanes J. Phys. Chem. B 105 2001 1176 1184
20. J.A. Biscardi, and E. Iglesia Structure and function of metal cations in light alkane reactions catalyzed by modified H-ZSM5 Catal. Today 31 1996 207 231
21. J.A. Biscardi, and E. Iglesia Non-oxidative reactions of propane on Zn/Na-ZSM5 Phys. Chem. Chem. Phys. 1 1999 5753 5759
22. J.A. Biscardi, and E. Iglesia Reaction pathways and rate-determining steps in reactions of alkanes on H-ZSM5 and Zn/H-ZSM5 catalysts J. Catal. 182 1999 117 128
23. J.A. Biscardi, G.D. Meitzner, and E. Iglesia Structure and density of active Zn species in Zn/H-ZSM5 propane aromatization catalysts J. Catal. 179 1998 192 202
24. V. Dal Santo, M. Guidotti, R. Psaro, L. Marchese, F. Carniato, and C. Bisio Rational design of single-site heterogeneous catalysts: towards high chemo-, regio- and stereoselectivity Proc. R. Soc. A - Math. Phys. 468 2012 1904 1926
25. K.L. Fujdala, and T.D. Tilley Design and synthesis of heterogeneous catalysts: the thermolytic molecular precursor approach J. Catal. 216 2003 265 275
26. V. Vidal, A. Theolier, J. ThivolleCazat, J.M. Basset, and J. Corker Synthesis, characterization, and reactivity, in the C-H bond activation of cycloalkanes, of a silica-supported tantalum(III) monohydride complex: (SiO)(2)Ta-III-H J. Am. Chem. Soc. 118 1996 4595 4602
27. J.M. Basset, C. Coperet, D. Soulivong, M. Taoufik, and J.T. Cazat Metathesis of alkanes and related reactions Acc. Chem. Res. 43 2010 323 334
28. V. Dufaud, G.P. Niccolai, J. Thivollecazat, and J.M. Basset Surface organometallic chemistry of inorganic oxides - the synthesis and characterization of (Sio)Ta(=Chc(Ch3)(3))(Ch2c(Ch3)(3))(2) and (Sio)(2)Ta(=Chc(Ch3)(3))(Ch2c(Ch3)(3)) J. Am. Chem. Soc. 117 1995 4288 4294
29. L.A. Williams, N. Guo, A. Motta, M. Delferro, I.L. Fragala, J.T. Miller, and T.J. Marks Surface structural-chemical characterization of a single-site d(0) heterogeneous arene hydrogenation catalyst having 100% active sites Proc. Natl. Acad. Sci. USA 110 2013 413 418
30. E.A. Mamedov, and V.C. Corberan Oxidative dehydrogenation of lower alkanes on vanadium oxide-based catalysts - the present state-of-the-art and outlooks Appl. Catal. A - Gen. 127 1995 1 40
31. D.A. Ruddy, N.L. Ohler, A.T. Bell, and T.D. Tilley Thermolytic molecular precursor route to site-isolated vanadia-silica materials and their catalytic performance in methane selective oxidation J. Catal. 238 2006 277 285
32. 3 J. Catal. 134 1992 492 505
33. C. Coperet, M. Chabanas, R.P. Saint-Arroman, and J.M. Basset Homogeneous and heterogeneous catalysis: bridging the gap through surface organometallic chemistry Angew. Chem., Int. Ed. 42 2003 156 181
34. F. Blanc, J. Thivolle-Cazat, J.M. Basset, C. Coperet, A.S. Hock, Z.J. Tonzetich, A. Sinha, and R.R. Schrock Highly active, stable, and selective well-defined silica supported mo imido olefin metathesis catalysts J. Am. Chem. Soc. 129 2007 2007 5779 (vol. 129, pg 1044, 2007)
35. D. Gajan, and C. Coperet Silica-supported single-site catalysts: to be or not to be? A conjecture on silica surfaces New J. Chem. 35 2011 2403 2408
36. C. Coperet C-H bond activation and organometallic intermediates on isolated metal centers on oxide surfaces Chem. Rev. 110 2010 656 680
37. 2+ on silica catalyst ACS Catal. 4 2014 1091 1092
38. C. Chen, T.R. Dugan, W.W. Brennessel, D.J. Weix, and P.L. Holland Z-selective alkene isomerization by high-spin cobalt(II) complexes J. Am. Chem. Soc. 136 2014 945 955
39. 3 Proc. Indian Acad. Sci. 47 1958 329 334
40. H. Kim, K.M. Kosuda, R.P. Van Duyne, and P.C. Stair Resonance Raman and surface- and tip-enhanced Raman spectroscopy methods to study solid catalysts and heterogeneous catalytic reactions Chem. Soc. Rev. 39 2010 4820 4844
41. A.D. Becke Density-functional thermochemistry. 3. The role of exact exchange J. Chem. Phys. 98 1993 5648 5652
42. F.J. Feher, D.A. Newman, and J.F. Walzer Silsesquioxanes as models for silica surfaces J. Am. Chem. Soc. 111 1989 1741 1748
43. W. Gaussian 09 v. Revision D.01, Gaussian Inc., CT, 2009.
44. H.P. Hratchian, and H.B. Schlegel Using Hessian updating to increase the efficiency of a Hessian based predictor-corrector reaction path following method J. Chem. Theory Comput. 1 2005 61 69
45. A. Schafer, C. Huber, and R. Ahlrichs Fully optimized contracted Gaussian-basis sets of triple zeta valence quality for atoms Li to Kr J. Chem. Phys. 100 1994 5829 5835
46. G. Bunker Introduction to XAFS: A Practical Guide to X-ray Absorption Fine Structure Spectroscopy 2010 Cambridge University Press New York
47. G.J. Kruger, and E.C. Reynhardt Hexaamminecobalt(III) chloride Acta Crystallogr., Sect. B - Struct. Sci. 34 1978 915 917
48. S. Aizawa, S. Iida, K. Matsuda, and S. Funahashi Nitrogen-14 NMR study on solvent exchange of the octahedral cobalt(II) ion in neat 1,3-propanediamine and n-propylamine at various temperatures and pressures. Tetrahedral-octahedral equilibrium of the solvated cobalt(II) ion in n-propylamine as studied by EXAFS and electronic absorption spectroscopy Inorg. Chem. 35 1996 1338 1342
49. R.D. Shannon Revised effective ionic-radii and systematic studies of interatomic distances in halides and chalcogenides Acta Crystallogr. Sect. A 32 1976 751 767
50. J.S. Chen, R.H. Jones, S. Natarajan, M.B. Hursthouse, and J.M. Thomas A novel open-framework cobalt phosphate-containing a tetrahedrally coordinated cobalt(II) center - Copo4-Center-Dot-0.5 C2h10n2 Angew. Chem., Int. Ed. 33 1994 639 640
51. S. Dzwigaj, and M. Che Incorporation of Co(II) in dealuminated BEA zeolite at lattice tetrahedral sites evidenced by XRD, FTIR, diffuse reflectance UV-vis, EPR, and TPR J. Phys. Chem. B 110 2006 12490 12493
52. B.M. Weckhuysen, A.A. Verberckmoes, M.G. Uytterhoeven, F.E. Mabbs, D. Collison, E. de Boer, and R.A. Schoonheydt Electron spin resonance of high-spin cobalt in microporous crystalline cobalt-containing aluminophosphates J. Phys. Chem. B 104 1999 37 42
53. L.E. Iton, I. Choi, J.A. Desjardins, and V.A. Maroni Stabilization of Co(III) in aluminophosphate molecular-sieve frameworks Zeolites 9 1989 535 538
54. 3: an investigation of structure-activity relationships Catal. Today 131 2008 305 313
55. C.W. Tang, C.B. Wang, and S.H. Chien Characterization of cobalt oxides studied by FT-IR, Raman, TPR and TG-MS Thermochim. Acta 473 2008 68 73
56. B. Humbert, A. Burneau, J.P. Gallas, and J.C. Lavalley Origin of the Raman bands, D1 and D2, in high surface-area and vitreous silicas J. Non-Cryst. Solids 143 1992 75 83
57. G.F.F.A.G. Buekens Thermal cracking of propane. Kinetics and product distributions Ind. Eng. Chem. Process Des. Dev. 7 1968 435 447
58. R.Z. Ma, Z.P. Liu, K. Takada, K. Fukuda, Y. Ebina, Y. Bando, and T. Sasaki Tetrahedral Co(II) coordination in alpha-type cobalt hydroxide: Rietveld refinement and X-ray absorption spectroscopy Inorg. Chem. 45 2006 3964 3969
59. 2 materials. A XAFS study J. Am. Chem. Soc. 120 1998 2059 2070
60. L.T. Zhuravlev Concentration of hydroxyl-groups on the surface of amorphous silicas Langmuir 3 1987 316 318
61. X.B. Ji, M.C. Buzzeo, C.E. Banks, and R.G. Compton Electrochemical response of cobalt(II) in the presence of ammonia Electroanalysis 18 2006 44 52
62. T.W.S. Anthony Martin Newton Kinetics and mechanism of the thermal decomposition of hexaamminecobalt(III) and aquopentaamminecobalt(III) ions in acidic aqueous solution Can. J. Chem. 52 1974 2751 2759
63. D.M. Duggan, and D.N. Hendrickson Magnetic exchange interactions in transition-metal dimers. 4. High-spin cobalt(II)-2,2′,2″-triaminotriethylamine complexes with oxalate inner-sphere and cyanate, thiocyanate, chloride, and azide outer-sphere bridges Inorg. Chem. 14 1975 1944 1956
64. x with propene over cobalt-exchanged zeolites Chem. Commun. 2007 1930 1932
65. F. Geobaldo, B. Onida, P. Rivolo, F. Di Renzo, F. Fajula, and E. Garrone Nature and reactivity of Co species in a cobalt-containing beta zeolite: an FTIR study Catal. Today 70 2001 107 119
66. A. Goodrow, and A.T. Bell A theoretical investigation of the selective oxidation of methanol to formaldehyde on isolated vanadate species supported on silica J. Phys. Chem. C 111 2007 14753 14761
67. Y.-R. Luo Comprehensive Handbook of Chemical Bond Energies 2007 CRC Press Boca Raton, FL
68. S.P. Frank, and R. Hartley The Metal-Carbon Bond 1985 Wiley New York
69. A. Dedieu Transition Metal Hydrides 1991 VCH New York
70. R. Xu, M. Bittner, G. Klatt, and H. Koppel Influence of ligands on the dynamics of hydrogen elimination in cationic complexes of Co and Rh J. Phys. Chem. A 112 2008 13139 13148
71. S.M. Bellows, T.R. Cundari, and P.L. Holland Spin crossover during beta-hydride elimination in high-spin iron(II)- and cobalt(II)-alkyl complexes Organometallics 32 2013 4741 4751
72. R. Wischert, P. Laurent, C. Copéret, F. Delbecq, and P. Sautet γ-Alumina: the essential and unexpected role of water for the structure, stability, and reactivity of "defect" sites J. Am. Chem. Soc. 134 2012 14430 14449
73. M.P. Conley, V. Mougel, D.V. Peryshkov, W.P. Forrest, D. Gajan, A. Lesage, L. Emsley, C. Coperet, and R.R. Schrock A well-defined silica-supported tungsten oxo alkylidene is a highly active alkene metathesis catalyst J. Am. Chem. Soc. 135 2013 19068 19070
74. M. Delley, M. Conley, and C. Copéret Polymerization on CO-reduced Phillips catalyst initiates through the C-H bond activation of ethylene on Cr-O sites Catal. Lett. 144 2014 805 808
75. 3 catalysts Catal. Lett. 103 2005 143 148
76. M.F. Delley, F. Núñez-Zarur, M.P. Conley, A. Comas-Vives, G. Siddiqi, S. Norsic, V. Monteil, O.V. Safonova, and C. Copéret Proton transfers are key elementary steps in ethylene polymerization on isolated chromium(III) silicates Proc. Natl. Acad. Sci. 111 2014 11624 11629
77. M.P. Conley, M.F. Delley, G. Siddiqi, G. Lapadula, S. Norsic, V. Monteil, O.V. Safonova, and C. Copéret Polymerization of ethylene by silica-supported dinuclear CrIII sites through an initiation step involving C-H bond activation Angew. Chem., Int. Ed. 53 2014 1872 1876