Copper(II) complexes of arylhydrazones of β-diketones immobilized on Zn-Al layered double hydroxides as effective recyclable catalysts for peroxidative oxidation of alkanes

Applied Catalysis A: General

Volumn 439-440, Issue , 2012, Pages 15-23

  Mac Leod, Tatiana C O ^a   Kopylovich, Maximilian N ^a   Guedes Da Silva, M Fátima C ^a,b   Mahmudov, Kamran T ^a,c   Pombeiro, Armando J L ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b UNIVERSIDADE LUSÓFONA DE HUMANIDADES E TECNOLOGIAS   (Portugal)

^c BAKU STATE UNIVERSITY   (Azerbaijan)

Author keywords

Alkane oxidation; Cu II complexes of arylhydrazones of diketones; Immobilization of catalysts; Layered double hydroxides; Recycling of catalysts

Indexed keywords

ALKANE OXIDATION; COPPER COMPLEXES; DIFFERENTIAL THERMALS; DIKETONES; FUNCTIONALIZED; HETEROGENIZED CATALYSTS; LAYERED DOUBLE HYDROXIDES; N-HEPTANES; N-HEXANE; N-OCTANES; N-PENTANE; PEROXIDATIVE OXIDATION; RECYCLABLE CATALYST; RECYCLING OF CATALYSTS; THERMOGRAVIMETRIC; ZN-AL LAYERED DOUBLE HYDROXIDES;

BUTANE; CATALYSTS; COMPLEXATION; HEXANE; KETONES; RECYCLING; SODIUM; SYNTHESIS (CHEMICAL); X RAY POWDER DIFFRACTION; ZINC;

COPPER COMPOUNDS;

EID: 84865117588     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2012.06.032     Document Type: Article

References (85)

1. Structure and Bonding. Series Editor: D.M.P Mingos. Editorial Board: P. Day, T.J. Meyer, H.W. Roesky, J.-P. Sauvage, Layered Double Hydroxides. Volume Editors: X. Duan, D.G. Evans, vol. 119, 2005.
2. A. De Roy, C. Forano, K. El Malki, and J.P. Besse M.L. Ocelli, H.E. Robson, Expanded Clays and other Microporous Solids 1992 Van Nostrand Reinhold New York 108 169
3. A.I. Khan, and D. O'Hare J. Mater. Chem. 12 2002 3191 3198
4. P.S. Braterman, Z.P. Xu, and F. Yarberry S.M. Auerbach, K.A. Carrado, P.K. Dutta, Handbook of Layered Materials 2004 Wiley New York cap. 8
5. S. Carlino Solid State Ionics 98 1997 73 84
6. M. Meyn, K. Beneke, and G. Lagaly Inorg. Chem. 29 1990 5201 5207
7. V. Rives, and M.A. Ulibarri Coord. Chem. Rev. 181 1999 61 120
8. A. Vaccari Appl. Clay Sci. 14 1999 161 198
9. G. Centi, and S. Perathoner Microporous Mesoporous Mater. 107 2008 3 15
10. B. Sels, D. De Vos, M. Buntinx, F. Pierard, A. Kirsch-De Mesmaeker, and P. Jacobs Nature 400 1999 855 857
11. M. Mokhtar, T.S. Saleh, and S.N. Basahel J. Mol. Catal. A: Chem. 353 2012 122 131
12. A.I. Khan, A. Ragavan, B. Fong, C. Markland, M. O'Brien, T.G. Dunbar, G.R. Williams, and D. O'Hare Ind. Eng. Chem. Res. 48 2009 10196 10205
13. Y. Kuang, L. Zhao, S. Zhang, F. Zhang, M. Dong, and S. Xu Materials 3 2010 5220 5235
14. M.N. Kopylovich, K.T. Mahmudov, M.F.C. Guedes da Silva, M.L. Kuznetsov, P.J. Figiel, Y.Y. Karabach, K.V. Luzyanin, and A.J.L. Pombeiro Inorg. Chem. 50 2011 918 931
15. M.N. Kopylovich, A.C.C. Nunes, K.T. Mahmudov, M. Haukka, T.C.O. Mac Leod, L.M.D.R.S. Martins, M.L. Kuznetsov, and A.J.L. Pombeiro Dalton Trans. 40 2011 2822 2836
16. A.E. Shilov, and G.B. Shul'pin Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes 2000 Kluwer Boston
17. G.B. Shul'pin Mini-Rev. Org. Chem. 6 2009 95 104
18. A.E. Shilov, and G.B. Shul'pin Chem. Rev. 97 1997 2879 2932
19. J.A. Labinger, and J.E. Bercaw Nature 417 2002 507 514
20. A.A. Fokin, and P.R. Schreiner Chem. Rev. 102 2002 1551 1593
21. R.H. Crabtree J. Organomet. Chem. 689 2004 4083 4091
22. K.M. Parida, M. Sahoo, and S. Singha J. Mol. Catal. A: Chem. 329 2010 7 12
23. S.H. Lau, V. Caps, K.W. Yeung, K.Y. Wong, and S.C. Tsang Microporous Mesoporous Mater. 32 1999 279 285
24. N.M.F. Carvalho, A. Horn Jr., and O.A.C. Antunes Appl. Catal. A: Gen. 305 2006 140 145
25. J.M. Vincent, S.B. Barbry, C. Pierre, and J.B. Verlhac J. Chem. Soc. Dalton Trans. 1999 1913 1914
26. K.T. Mahmudov, M.N. Kopylovich, M.F.C. Guedes da Silva, P.J. Figiel, Y.Y. Karabach, and A.J.L. Pombeiro J. Mol. Catal. A: Chem. 318 2010 44 50
27. M.N. Kopylovich, K.T. Mahmudov, M. Haukka, P.J. Figiel, A. Mizar, M.F.C. Guedes da Silva, and A.J.L. Pombeiro Eur. J. Inorg. Chem. 2011 4175 4181
28. A.M. Kirillov, M.N. Kopylovich, M.V. Kirillova, M. Haukka, M.F.C. Guedes da Silva, and A.J.L. Pombeiro Angew. Chem. Int. Ed. 44 2005 4345 4349
29. A.M. Kirillov, M.N. Kopylovich, M.V. Kirillova, E.Y. Karabach, M. Haukka, M.F.C. Guedes da Silva, and A.J.L. Pombeiro Adv. Synth. Catal. 348 2006 159 174
30. C. Di Nicola, Y.Y. Karabach, A.M. Kirillov, M. Monari, L. Pandolfo, C. Pettinari, and A.J.L. Pombeiro Inorg. Chem. 46 2007 221 230
31. Y.Y. Karabach, A.M. Kirillov, M. Haukka, M.N. Kopylovich, and A.J.L. Pombeiro J. Inorg. Biochem. 102 2008 1190 1194
32. M.V. Kirillova, A.M. Kirillov, M.F.C. Guedes da Silva, and A.J.L. Pombeiro Eur. J. Inorg. Chem. 2008 3423 3427
33. A. Sakthivel, and P. Selvam J. Catal. 211 2002 134 143
34. G. Lü, R. Zhao, G. Qian, Y. Qi, X. Wang, and J. Suo Catal. Lett. 97 2004 115 118
35. G. Huang, Y. Guo, H. Zhou, S. Zhao, S. Liu, A. Wang, and J. Wei J. Mol. Catal. A: Chem. 273 2007 144 148
36. E.G. Derouane, V. Parmon, F. Lemos, F. Ramôa Ribeiro, Sustainable Strategies for the Upgrading of Natural Gas: Fundamentals, Challenges and Opportunities. vol. 191 2005 Springer Dordrecht
37. E.G. Derouane, J. Haber, F. Lemos, F. Ramôa Ribeiro, M. Guinet, Catalytic Activation and Functionalization of Light Alkanes, NATO ASI Series vol. 44 1998 Kluwer Academic Publisher Dordrecht
38. R.A. Sheldon, I.W.C.E. Arends, and U. Hanefeld Green Chemistry & Catalysis 2007 Wiley-VCH Weinheim
39. S. Bhattacharjee, K.-E. Jeong, S.-Y. Jeong, and W.-S. Ahn New J. Chem. 34 2010 156 162
40. B.M. Choudary, T. Ramani, H. Maheswaran, L. Prashant, K.V.S. Ranganath, and K.V. Kumar Adv. Synth. Catal. 348 2006 493 498
41. B. Monteiro, S. Gago, S.S. Balula, A.A. Valente, I.S. Gonalves, and M. Pillinger J. Mol. Catal. A 312 2009 23 30
42. E. Kafunkova, C. Taviot-Gueho, P. Bezdicka, M. Klementova, P. Kovar, P. Kubat, J. Mosinger, M. Pospsil, and K. Lang Chem. Mater. 22 2010 2481 2490
43. J. Inacio, C. Taviot-Guého, S. Morlat-Thérias, M. de Roy, and J. Besse J. Mater. Chem. 11 2001 640 643
44. K.T. Mahmudov, A.M. Maharramov, R.A. Aliyeva, I.A. Aliyev, M.N. Kopylovich, and A.J.L. Pombeiro Anal. Lett. 43 2010 2923 2938
45. Bruker APEX2 & SAINT. Bruker 2004 AXS Inc. Madison, Wisconsin, USA
46. G.M. Sheldrick Acta Crystallogr. Sect. A 46 1990 467 473
47. G.M. Sheldrick Acta Crystallogr. Sect. A 64 2008 112 122
48. L.J. Farrugia J. Appl. Crystallogr. 32 1999 837 838
49. G.B. Shul'pin J. Mol. Catal. A: Chem. 189 2002 39 66
50. G.B. Shul'pin Comptes Rendus Chimie 6 2003 163 178
51. T.C.O. Mac Leod, M.V. Kirillova, A.J.L. Pombeiro, M.A. Schiavon, and M.D. Assis Appl. Catal. A: Gen. 372 2010 191 198
52. G.B. Shul'pin, T. Sooknoi, V.B. Romakh, G. Süss-Fink, and L.S. Shul'pina Tetrahedron Lett. 47 2006 3071 3075
53. S. Das, G.W. Brudvig, and R.H. Crabtree Chem. Commun. 2008 413 424
54. G.B. Shul'pin, G.V. Nizova, Y.N. Kozlov, V.S. Arutyunov, A.C.M. Santos, A.C.T. Ferreira, and D. Mandelli J. Organomet. Chem. 690 2005 4498 4504
55. M.N. Kopylovich, K.T. Mahmudov, M.F.C.G. Silva, L.M.D.R.S. Martins, M.L. Kuznetsov, T.F.S. Silva, J.J.R.F. Silva, and A.J.L. Pombeiro J. Phys. Org. Chem. 24 2011 764 773
56. L. Hickey, J.L. Kloprogge, and R.L. Frost J. Mater. Sci. 35 2000 4347 4355
57. F.M. Labajos, V. Rives, and M.A. Ulibarri J. Mater. Sci. 27 1992 1546 1552
58. M. Halma, K.A.D.F. Castro, C. Taviot-Gueho, V. Prevot, C. Forano, F. Wypych, and S. Nakagaki J. Catal. 257 2008 233 243
59. J.H. Lee, S.W. Rhee, and D. Jung Bull. Korean Chem. Soc. 26 2005 248 252
60. H. Chai, Y. Lin, D.G. Evans, and D. Li Ind. Eng. Chem. Res. 47 2008 2855 2860
61. J. Ritz, H. Fuchs, H. Kieczka, and W.C. Moran Caprolactam Ullmann's Encyclopedia of Industrial Chemistry 6th ed. 2002 Wiley-VCH Weinheim, Germany
62. G.B. Shul'pin, J. Gradinaru, and Y.N. Kozlov Org. Biomol. Chem. 1 2003 3611 3617
63. A.M. Kirillov, M.V. Kirillova, L.S. Shul'pina, P.J. Figiel, K.R. Gruenwald, M.F.C. Guedes da Silva, M. Haukka, A.J.L. Pombeiro, and G.B. Shul'pin J. Mol. Catal. A: Chem. 350 2011 26 34
64. G.B. Shul'pin, Y.N. Kozlov, L.S. Shul'pina, A.R. Kudinov, and D. Mandelli Inorg. Chem. 48 2009 10480 10482
65. G.B. Shul'pin, Y.N. Kozlov, L.S. Shul'pina, and P.V. Petrovskiy Appl. Organometal. Chem. 24 2010 464 472
66. G.B. Shul'pin Org. Biomol. Chem. 8 2010 4217 4228
67. M.N. Kopylovich, M.J. Gajewska, K.T. Mahmudov, M.V. Kirillova, P.J. Figiel, M.F.C. Guedes da Silva, B. Gil-Hernández, J. Sanchiz, A.J.L. Pombeiro, New. J. Chem. 36, http://dx.doi.org/10.1039/C2NJ40210F, in press.
68. F. Wypych, A. Bail, M. Halma, and S. Nakagaki J. Catal. 234 2005 431 437
69. M.S. Sadjadi, A. Ebadi, and K. Zare Reac. Kinet. Mech. Catal. 99 2010 119 124
70. R.D. Bach Z.Z. Rappoport, The Chemistry of Peroxides vol. 2 2006 Wiley New York
71. J.M. Thomas, and R. Raja Chem. Commun. 2001 675 687
72. M. Halma, K.A.D. Freitas Castro, V. Prévot, C. Forano, F. Wypych, and S. Nakagaki J. Mol. Catal. A Chem. 310 2009 42 50
73. K.A.D.F. Castro, A. Bail, P.B. Groszewicz, G.S. Machado, W.H. Schreiner, F. Wypych, and S. Nakagaki Appl. Catal. A: Gen. 386 2010 51 59
74. B.L. Caetano, L.A. Rocha, E. Molina, Z.N. Rocha, G. Ricci, P.S. Calefi, O.J. de Lima, C. Mello, E.J. Nassar, and K.J. Ciuffi Appl. Catal. A: Gen. 311 2006 122 134
75. S. Bhattacharjee, and J.A. Anderson Catal. Lett. 95 2004 119 125
76. V. Kesavan, D. Dhar, Y. Koltypin, N. Perkas, O. Palchik, A. Gedanken, and S. Chandersekaran Pure Appl. Chem. 73 2001 85 91
77. J.A.L. Silva, J.J.R.F. Silva, and A.J.L. Pombeiro Coord. Chem. Rev. 255 2011 2232 2248
78. M.L. Kuznetsov, and A.J.L. Pombeiro Inorg. Chem. 48 2009 307 318
79. M. Costas, M.P. Mehn, M.P. Jensen, and L. Que Jr. Chem. Rev. 104 2004 939 986
80. G.V. Nizova, B. Krebs, G. Suss-Fink, S. Schindler, L. Westerheide, L.G. Cuervo, and G.B. Shul'pin Tetrahedron 58 2002 9231 9237
81. G. Suss-Fink, L. Gonzalez, and G.B. Shul'pin Appl. Cat. A: Gen. 217 2001 111 117
82. G.B. Shul'pin, H. Stoeckli-Evans, D. Mandelli, Y.N. Kozlov, A.T. Vallina, C.B. Woitiski, R.S. Jimenez, and W.A. Carvalho J. Mol. Catal. A: Chem. 219 2004 255 264
83. G.B. Shul'pin, M.V. Kirillova, Y.N. Kozlov, L.S. Shul'pina, A.R. Kudinov, and A.J.L. Pombeiro J. Catal. 277 2011 164 172
84. M.V. Kirillova, Y.N. Kozlov, L.S. Shul'pina, O.Y. Lyakin, A.M. Kirillov, E.P. Talsi, A.J.L. Pombeiro, and G.B. Shul'pin J. Catal. 268 2009 26 38
85. M.V. Kirillova, M.L. Kuznetsov, V.B. Romakh, L.S. Shul'pina, J.J.R. Frausto da Silva, A.J.L. Pombeiro, and G.B. Shul'pin J. Catal. 267 2009 140 157