A solid acid catalyst at the threshold of superacid strength: NMR, calorimetry, and density functional theory studies of silica-supported aluminum chloride

Journal of the American Chemical Society

Volumn 119, Issue 50, 1997, Pages 12231-12239

  Xu, Teng ^a   Kob, Nick ^b   Drago, Russell S ^b   Nicholas, John B ^c   Haw, James F ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b University of Florida ^*  (United States)

^c PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM CHLORIDE; SILICON DIOXIDE; ZEOLITE;

ARTICLE; CALCULATION; CALORIMETRY; CATALYST; CHEMICAL STRUCTURE; ENERGY TRANSFER; ISOMERISM; OLIGOMERIZATION; PH; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0031576662     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970850n     Document Type: Article

References (64)

1. Corma, A. Chem. Rev. 1995, 95, 559-614.
2. Farneth, W. E.; Gorte, R. J. Chem. Rev. 1995, 95, 615-635.
3. van Santen, R. A.; Kramer, G. J. Chem. Rev. 1995, 95, 637-660.
4. Armor, J. N. Environmental Catalysis; Armor, J. N., Ed.; American Chemical Society: Washington, DC, 1994.
5. Cusumano, J. A. Chemtech 1992, 22, 482-489.
6. Bell, A. T.; Manzer, L. E.; Chen, N. Y.; Weekman, V. W.; Hegedus, L. L.; Pereira, C. J. Chem. Eng. Prog. 1995, 91, 26-34.
7. Tanabe, K.; Misono, M.; Ono, Y.; Hattori, H. New Solid Acids and Bases Their Catalytic Properties; Elsevier: Amsterdam, 1989; Vol. 51.
8. Haw, J. F.; Nicholas, J. B.; Xu, T.; Beck, L. W.; Ferguson, D. B. Acc. Chem. Res. 1996, 29, 259-267.
9. Drago, R. S.; Dias, S. C.; Torrealba, M.; de Lima, L. J. Am. Chem. Soc. 1997, 119, 4444-4452.
10. Kustov, L. M.; Kazansky, V. B.; Figuearas, F.; Tichit, D. J. Catal. 1994, 150, 143-149.
11. Adeeva, V.; de Haan, J. W.; Janchen, J.; Lei, G. D.; Schunemann, V.; van de Ven, L. J. M.; Sachtler, W. M. H.; van Santen, R. A. J. Catal. 1995, 151, 364-372.
12. Farcasiu, D.; Ghenciu, A.; Li, J.-Q. J. Catal. 1996, 158, 116-127.
13. Drago, R. S.; Kob, N. J. Phys. Chem. 1997, 101, 3360-3364.
14. Xu, T.; Barich, D. H.; Torres, P. D.; Haw, J. F. J. Am. Chem. Soc. 1997, 119, 406-414.
15. Farcasiu, D. Acc. Chem. Res. 1982, 15, 46-51.
16. Drago, R. S.; Getty, E. E. U.S. Patent No. 4,719,190, 1988.
17. Drago, R. S.; Getty, E. E. J. Am. Chem. Soc. 1988, 110, 3311-3312.
18. Drago, R. S.; Getty, E. E. U.S. Patent No. 4,929,80, 1990.
19. Getty, E. E.; Drago, R. S. Inorg. Chem. 1990, 29, 1186-1192.
20. Drago, R. S.; Petrosius, S. C.; Chronister, C. W. Inorg. Chem. 1994, 33, 367-372.
21. Drago, R. S.; Petrosius, S. C.; Kaufman, P. B. J. Mol. Catal. 1994, 89, 317-328.
22. Drago, R. S.; Petrosius, S. C.; Kaufman, P. B. New J. Chem. 1994, 18, 937-939.
23. Lim, Y. Y.; Drago, R. S., Babich, M. W.; Wong, N.; Doan, P. E. J Am. Chem. Soc. 1987, 109, 169-174.
24. Chronister, C. W.; Drago, R. S. J. Am. Chem. Soc. 1993, 115, 4793-4798.
25. Munson, E. J.; Murray, D. K.; Haw, J. F. J. Catal. 1993, 141, 733-736.
26. Xu, T.; Haw, J. F. Topics Catal. 1997, 4, 109-118.
27. Johnson, B. G.; Frisch, M. J. J. Chem. Phys. 1994, 100, 7429-7442.
28. Johnson, B. G.; Frisch, M. J. Chem. Phys. Lett. 1993, 216, 133-140.
29. Andzelm, J. In Density Functional Methods in Chemistry; Labanowski, J., Andzelm, J., Eds.; Springer-Verlag: New York, 1991; p 155.
30. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University: New York, 1989.
31. Labanowski, J.; Andzelm, J. Density Functional Methods in Chemistry; Labanowski, J., Andzelm, J., Eds.; Springer-Verlag: New York, 1991.
32. Slater, J. C. Phys. Rev. 1937, 51, 846-851.
33. Vosko, S. J.; Wilk, L.; Nussair, M. Can. J. Phys. 1980, 58, 1200-1211.
34. Johnson, B. G.; Gill, P. M.; Pople, J. A. J. Chem. Phys. 1993, 98, 5612-5626.
35. Stave, M. S.; Nicholas, J. B. J. Phys. Chem. 1993, 97, 9630-9641.
36. Stave, M. S.; Nicholas, J. B. J. Phys. Chem. 1995, 99, 15046-15061.
37. Ziegler, T. Chem. Rev. 1991, 91, 651-667.
38. Jones, R. O.; Gunnarsson, O. Rev. Mod. Phys. 1989, 61, 689-746.
39. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560-571.
40. Dixon, D. A. In Density Functional Methods in Chemistry; Labanowski, J., Andzelm J., Eds.; Springer-Verlag: New York, 1991.
41. Frisch, M. J.; Trucks, G. W.; Schlegal, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; T. Keith; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.2.; Frisch, M. J., Trucks, G. W., Schlegal, H. B., Gill, P. M. W., Johnson, B. G., Robb, M. A., Cheeseman, J. R., Keith, T., Petersson, G. A., Montgomery, J. A., Raghavachari, K., Al-Laham, M. A., Zakrzewski, V. G., Ortiz, J. V., Foresman, J. B., Cioslowski, J., Stefanov, B. B., Nanayakkara, A., Challacombe, M., Peng, C. Y., Ayala, P. Y., Chen, W., Wong, M. W., Andres, J. L., Replogle, E. S., Gomperts, R., Martin, R. L., Fox, D. J., Binkley, J. S., Defrees, D. J., Baker, J., Stewart, J. P., Head-Gordon, M., Gonzalez, C., Pople, J. A., Eds.; Gaussian, Inc.: Pittsburgh, PA, 1995.
42. Sato, S.; Maciel, G. E. J. Mol. Catal. A 1995, 101, 153-161.
43. Beck, L. W.; White, J. L.; Haw, J. F. J. Am. Chem. Soc. 1994, 116, 9657-9661.
44. Beck, L. W.; Haw, J. F. J. Phys. Chem. 1995, 99, 1076-1079.
45. Lunsford, J. H.; Rothwell, W. P.; Shen, W. J. Am. Chem. Soc. 1985, 107, 1540-1547.
46. Chu, P.-J.; Mallmann, A. d.; Lunsford, J. H. J. Phys. Chem. 1991, 95, 7362-7368.
47. Maciel, G. E.; Haw, J. F.; Chuang, I.-S.; Hawkins, B. L.; Early, T. E.; McKay, D. R.; Petrakis, L. J. Am. Chem. Soc. 1983, 105, 5529-5535.
48. Haw, J. F.; Chuang, I.-S.; Hawkins, B. L.; Maciel, G. E. J. Am. Chem. Soc. 1983, 105, 7206-7207.
49. Xu, T.; Munson, E. J.; Haw, J. F. J. Am. Chem. Soc. 1994, 116, 1962-1972.
50. Bosácek, V.; Kubelková, L.; Nováková, J. In Catalysis and Adsoption by Zeolites; Öhlmann, G., Ed.; Elsevier Science: Amsterdam, 1991.
51. Biaglow, A. I.; Gone, R. J.; Kokotailo, G. T.; White, D. J. Catal. 1994, 148, 779-786.
52. Xu, T.; Torres, P. D.; Beck, L. W.; Haw, J. F. J. Am. Chem. Soc. 1995, 117, 8027-8028.
53. Breitmeier, E.; Haas, G.; Voelter, W. Atlas of Carbon-13 NMR Data; Heyden & Son Ltd.: London, 1979.
54. McClelland, R. A.; Reynolds, W. F. Can. J. Chem. 1976, 54, 718-725.
55. Olah, G. A.; White, A. M. J. Am. Chem. Soc. 1968, 90, 1884-1889.
56. Krivdin, L. B.; Zinchenko, S. V.; Kalabin, G. A.; Facelli, J. C.; Tufro, M. F.; Contreras, R. H.; Denisov, A. Y.; Gavrilyuk, O. A.; Mamatyuk, V. I. J. Chem. Soc., Faraday Trans. 1992, 88, 2459-2463.
57. White, J. L.; Beck, L. W.; Haw, J. F. J. Am. Chem. Soc. 1992, 114, 6182-6189.
58. Haw, J. F.; Richardson, B. R.; Oshiro, I. S.; Lazo, N. L.; Speed, J. A. J. Am. Chem. Soc. 1989, 111, 2052-2058.
59. Xu, T.; Haw, J. F. J. Am. Chem. Soc. 1994, 116, 7753-7759.
60. Opella, S. J. J. Am. Chem. Soc. 1979, 101, 5854-5856.
61. Nicholas, J. B.; Winans, R. E.; Harrison, R. J.; Iton, L. E.; Curtiss, L. A.; Hopfinger, A. J. J. Phys. Chem. 1992, 96, 10247-10257.
62. Brand, H. V.; Curtiss, L. A.; Iton, L. E. J. Phys. Chem. 1993, 97, 12773-12782.
63. In the earlier work we used the numerical DFT program DMol. The local exchange correlation functional of von Barth and Hedin was used, although this functional should give results very close to those given by the SVWN functional used in the current study. The basis set (DNP+) used in the earlier work was also by necessity different, although it is comparable to DZVP2 in size. The most important difference is that in the earlier study only the inner three or four atoms of the acid site (≡Si-O-Al≡ or ≡Si-OH-Al≡) were allowed to optimize, whereas all other atoms were fixed in crystal positions. This limited relaxation led to an artificially greater estimate of the acidity, which is remedied in the current work.
64. Beck, L. W.; Xu, T.; Nicholas, J. B.; Haw, J. F. J. Am. Chem. Soc. 1995, 117, 11594-11595.