In situ 13C solid-state NMR and ex situ GC-MS analysis of the products of tert-butyl alcohol dehydration on H-ZSM-5 zeolite catalyst

Chemistry - A European Journal

Volumn 2, Issue 2, 1996, Pages 157-167

  Stepanov, Alexander G ^a   Sidelnikov, Vladimir N ^a   Zamaraev, Kirill I ^a  

^a BORESKOV INSTITUTE OF CATALYSIS   (Russian Federation)

Author keywords

Alcohols; Cracking; Dehydrations; Isomerization; NMR spectroscopy

Indexed keywords

ADSORPTION STATE; BRANCHED HYDROCARBONS; HYDROCARBON PRODUCT; HZSM-5 ZEOLITES; LINEAR STRUCTURES; SHAPE SELECTIVITY; SIMPLE AROMATICS; TERT-BUTYL ALCOHOLS;

ALCOHOLS; BUTENES; CATALYSTS; CRACK INITIATION; CRACKS; ETHERS; ISOMERIZATION; ISOMERS; ISOTOPES; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARAFFINS; POSITIVE IONS;

DEHYDRATION;

EID: 0000832786     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020207     Document Type: Article

References (89)

1. J. Haber, J. Komorek-Hlodzik, T. Romotowski, Zeolites 1982, 2, 179-184.
2. M. T. Aronson, R. J. Gorte, W. E. Farneth, J. Catal. 1987, 105, 455-468.
3. C. Williams, M. A. Makarova, L. V. Malysheva, E. A. Paukshtis, E. P. Talsi, J. M. Thomas, K. I. Zamaraev, J. Catal. 1991, 127, 377-392
4. M. T. Aronson, R. J. Gorte, W. E. Farneth, D. White, J. Am. Chem. Soc. 1989, 111, 840-846.
5. A. G. Stepanov, K. I. Zamaraev, J. M. Thomas, Catal. Lett. 1992, 13, 407-422.
6. A. G. Stepanov, A. G. Maryasov, V. N. Romannikov, K. I. Zamaraev, Magn. Reson. Chem. 1994, 32, 16-23.
7. C. Williams, M. A. Makarova, L. V. Malysheva, E. A. Paukshtis, K. I. Zamaraev, J. M. Thomas, J. Chem. Soc. Faraday Trans. 1990, 86, 3473-3485.
8. M. A. Makarova, E. A. Paukshtis, C. Williams, J. M. Thomas, K. I. Zamaraev, J. Catal. 1994, 149, 36-51;
9. M. A. Makarova, C. Williams, K. I. Zamaraev, J. M. Thomas, J. Chem. Soc. Faraday Trans. 1994, 90, 2147-2153.
10. C. D. Chang, A. J. Silvestri, J. Catal. 1977, 47, 249.
11. E. G. Derouane, J. B. Nagy, P. Dejaifve, J. H. C. van Hoof, B. P. Spekman, J. C. Védrine, C. Naccache, J. Catal. 1978, 53, 40-55.
12. A. Brenner, P. H. Emmett, J. Catal. 1982, 75, 410-415.
13. V. N. Romannikov, V. N. Sidelnikov, K. G. Ione, React. Kinet. Catal. Lett. 1985, 27, 27-31.
14. E. A. Lombardo, R. Pierantozzi, W. K. Hall, J. Catal. 1988, 110, 171-183.
15. M. W. Anderson, J. Klinowski, J. Am. Chem. Soc. 1990, 112, 10-16;
16. M. W. Anderson, B. Sulikowski, P. J. Barrie, J. Klinowski, J. Phys. Chem. 1990, 94, 2730-2734.
17. J. L. White, N. D. Lazo, B. R. Richardson, J. F. Haw, J. Catal. 1990, 125, 260-263.
18. F. G. Oliver, E. J. Munson, J. F. Haw, J. Phys. Chem. 1992, 96, 8106-8111.
19. E. J. Munson, A. A. Kheir, N. D. Lazo, J. H. Haw, J. Phys. Chem. 1992, 96, 7740-7746.
20. S. N. Vereshchagin, N. N. Shishkina, A. G. Anshits, Kinet. Katal. 1991, 32, 1436-1440;
21. S. N. Vereshchagin, K. P. Dugaev, N. P. Kirik, N. N. Shishkina, A. G. Anshits, Catal. Today, 1995, 24, 349-356.
22. 13C NMR Spectroscopy, Methods and Applications in Organic Chemistry, Verlag Chemie, Weinheim, 1978.
23. C. E. Bronnimann, G. E. Maciel, J. Am. Chem. Soc. 1986, 108, 7154-7159.
24. A. E. Derome, Modern NMR Techniques for Chemistry Research, Pergamon Press, Oxford, 1987, pp. 259-268.
25. 13C]tBuOH, was used.
26. A. Pines, M. G. Gibby, J. S. Waugh, J. Chem. Phys. 1973, 59, 569-590.
27. R. K. Harris, Nuclear Magnetic Resonance Spectroscopy. A Physico-Chemical View, Pitman, London, 1983, pp. 17, 166.
28. A. G. Stepanov, M. V. Luzgin, V. N. Romannikov, K. I. Zamaraev, Catal. Lett. 1994, 24, 271-284.
29. To identify the isotropic chemical shifts δ for the broad signals the procedure of the variation of the speed of the sample rotation between 1.8-3.3 kHz was employed. The lines that corresponded to isotropic value of δ remained unshifted, while the positions of the spinning sidebands varied within δ = 15 depending on the rotation rate.
30. G. A. Olah, P. R. Cliffod, Y. Halpern, R. G. Johanson, J. Am. Chem. Soc. 1971, 93, 4219-4222.
31. G. A. Olah, G. Liang, J. Am. Chem. Soc. 1972, 94, 6434-6441.
32. D. Farcasiu, J. Chem. Soc. Chem. Commun. 1994, 1801-1802
33. E. J. Munson, T. Xu, J. F. Haw, J. Chem. Soc. Chem. Commun. 1993, 75-76;
34. T. Xu, J. Zhang, E. J. Munson, J. F. Haw, J. Chem. Soc. Chem. Commun. 1994, 2733-2735.
35. J. C. Rees, D. Whittaker, J. Chem. Soc. Perkin Trans. 1980, 2, 948.
36. J. F. Haw, B. R. Richardson, I. S. Oshio, N. D. Lazo, J. A. Speed, J. Am. Chem. Soc. 1989, 111, 2052-2058.
37. T. Xu, J. F. Haw, J. Am. Chem. Soc. 1994, 116, 7753-7759.
38. T. Xu, J. F. Haw, J. Am. Chem. Soc. 1994, 116, 10188-10195.
39. R. K. Harris, Nuclear Marnetic Resonance. A Physicochemical View, Pitman, London, 1983, p. 99.
40. L. J. Schwartz, E. Meirovitch, J. A. Ripmeester, J. H. Freed, J. Phys. Chem. 1983, 87, 4453-4461;
41. M. A. Keniry, Kintanar, R. L. Smith, H. S. Gutowski, E. Oldfield, Biochemistry 1984, 23, 288-298.
42. G. E. Maciel, D. W. Sindorf, V. J. Bartuska, J. Chromatogr. 1981, 205, 438;
43. G. R. Hays, A. D. H. Clague, R. Huis, G. Van der Velden, Appl. Surf. Sci. 1982, 10, 247-263.
44. L. M. Sverdlov, M. A. Kovner, E. P. Krainer, Vibrational Spectra of Poly-atomic Molecules, Nauka, Moscow, 1972 (in Russian).
45. J. P. van den Berg, J. P. Wolthuizen, A. D. H. Clague, G. R. Hays, R. Huis, J. H. C. van Hooff, J. Catal. 1983, 80, 130-138.
46. G. A. Olah, D. J. Donovan, J. Am. Chem. Soc. 1977, 99, 5026-5039.
47. A. G. Stepanov, V. N. Romannikov, K. I. Zamaraev, Catal. Lett. 1992, 13, 395-405.
48. G. A. Olah, Angew. Chem. Int. Ed. Engl. 1973, 12, 173-212.
49. M. Saunders, P. Vogel, E. L. Hagen, J. Rosenfeld, Acc. Chem. Res. 1973, 53-59.
50. B. V. Liengme, W. K. Hall, Trans. Faraday Soc. 1966, 62, 3229-3243.
51. N. D. Lazo, B. R. Richardson, P. D. Schettler, J. L. White, E. J. Munson, J. F. Haw, J. Phys. Chem. 1991, 95, 9420-9425.
52. A. G. Stepanov, K. I. Zamaraev, Catal. Lett. 1993, 19, 153-158.
53. J. Sommer, M. Hachoumy, F. Garin, D. Barthomeuf, J. Am. Chem. Soc. 1994, 116, 5491-5492;
54. J. Sommer, M. Hachoumy, F. Garin, D. Barthomeuf, J. Vedrine, ibid. 1995, 117, 1135-1136.
55. J. Engelhardt, W. K. Hall, J. Catal. 1995, 151, 1-9.
56. G. M. Kramer, G. B. McVicker, J. J. Ziemiak, J. Catal. 1985, 92, 355-363.
57. A. G. Stepanov, M. V. Luzgin, V. N. Romannikov, K. I. Zamaraev, J. Am. Chem. Soc. 1995, 117, 3615-3616.
58. G. A. Olah, E. B. Baker, J. C. Evans, W. S. Tolgyesi, J. S. McIntyre, I. J. Bastein, J. Am. Chem. Soc. 1964, 86, 1360-1373;
59. G. A. Olah, J. R. DeMember, A. Commeyras, J. L. Bribes, ibid. 1971, 93, 459-463.
60. L. J. Bellamy, Advances in Infrared Group Frequencies, Methuen, England, 1968.
61. V. Stubican, R. Roy, J. Am. Ceram. Soc. 1961, 44, 625-627.
62. V. B. Kazansky, I. N. Senchenya, J. Catal. 1989, 119, 108-126;
63. V. B. Kazansky, Acc. Chem. Res. 1991, 112, 379-383.
64. To substantiate this conclusion quantitatively a theoretical analysis is now in progress at our institute.
65. G. T. Kokotailo, S. L. Lawton, D. H. Olson, M. Meier, Nature (London) 1978, 272, 437-438;
66. E. M. Flanigen, J. M. Bennett, R. W. Grose, J. P. Cohen, R. L. Patton, R. M. Kirchner, J. V. Smith, ibid. 1978, 271, 512-516.
67. C. N. Satterfield, Heterogeneous Catalysis in Practice, Moscow, Mir, 1984, p. 202 (in Russian).
68. J. Datka, Zeolites, 1981, 1, 113-116;
69. J. Datka, in Catalysis on Zeolites (Eds: D. Kalló, Kh. M. Minachev), Akadémia Kiadó, Budapest, 1988, pp. 467-487.
70. J. Nováková, L. Kubelková, Z. Dolejšek, P. Jíru, Collect. Czech. Chem. Commun. 1979, 44, 3341-3345.
71. V. Bolis, J. C. Vedrine, J. P. Van de Berg, J. P. Wolthuizen, E. G. Derouane, J. Chem. Soc. Faraday Trans. 1, 1980, 76, 1606-1616.
72. H. Forster, J. Seebode, Proc. Int. Symp. Zeolite Catal., Siofok, Hungary, 1985, p. 413.
73. A. K. Ghosh, R. A. Kydd, J. Catal. 1986, 100, 185-195.
74. A. V. Demidov, A. A. Davydov, L. N. Kurina, Izv. Akad. Nauk. SSSR, Ser. Khim. 1989, 6, 1229-1233;
75. A. V. Demidov, T. A. Kazantseva, A. A. Davydov, Zh. Fiz. Khim. 1990, 64, 259-262.
76. E. A. Lombardo, J. M. Dereppe, G. Marcelin, W. K. Hall, J. Catal. 1988, 114, 167-175.
77. E. G. Derouane, J.-P. Gilson, J. B. Nagy, Zeolites 1982, 2, 42-46.
78. J.-P. Lange, A. Gutsze, J. Allgeier, H. G. Karge, Appl. Catal. 1988, 45, 345-356.
79. A. M. Butlerov, Zh. Russ. Fiz. Kkim. Obstch. 1877, 9, 38 (in Russian)
80. V. N. Ipatieff, H. Pines, J. Org. Chem. 1936, 1, 464;
81. H. Pines, The Chemistry of Catalytic Hydrocarbon Conversions, Academic Press, New York, 1981.
82. N. C. Deno, D. B. Boyd, J. D. Hodge, C. U. Pittman, Jr., J. O. Turner, J. Am. Chem. Soc. 1964, 86, 1745-1748.
83. V. N. Romannikov, V. M. Mastikhin, S. Hocevar, V. Drzaj, Zeolites, 1983, 3, 311-320.
84. T. A. Carpenter, J. Klinowski, D. T. B. Tennakoon, C. J. Smith, D. C. Edwards, J. Magn. Reson. 1986, 68, 561.
85. T. A. Brettell, R. L. Grob, Int. Laboratory 1986, 16, 30-44.
86. T. C. Farrar, E. D. Becker, Pulse and Fourier Transform NMR. Introduction to Theory and Methods, Academic Press, New York and London, 1971.
87. R. K. Harris, Nuclear Magnetic Resonance Spectroscopy. A Physico-Chemical View, Pitman, London, 1983, pp. 107-113.
88. M. W. Anderson, J. Klinowski, Chem. Phys. Lett. 1990, 172, 275-278.
89. A. G. Stepanov, V. N. Zudin, K. I. Zamaraev, Solid State NMR 1993, 2, 89-93.