Formation of carboxylic acids from small alkanes in zeolite H-ZSM-5

Chemistry - A European Journal

Volumn 6, Issue 13, 2000, Pages 2368-2376

  Luzgin, Mikhail V ^a   Stepanov, Alexander G ^a   Sassi, Alain ^b   Sommer, Jean ^b  

^a BORESKOV INSTITUTE OF CATALYSIS   (Russian Federation)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Alkanes; Carbon monoxide; Carboxylic acids; NMR spectroscopy; Zeolites

Indexed keywords

ALKANE; CARBOXYLIC ACID DERIVATIVE; ZEOLITE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; GAS CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TEMPERATURE;

EID: 0034601023     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000703)6:13<2368::AID-CHEM2368>3.0.CO;2-H     Document Type: Article

References (60)

1. a) H. S. Bloch, H. Pines, L. Schmerling, J. Am. Chem. Soc. 1946, 68, 153;
2. b) G. A. Olah, A. Molnar, Hydrocarbon Chemistry, Wiley, New York, 1995.
3. H. Hogeveen, G. F. Bickel, J. Chem. Soc. Chem. Commun. 1967, 635-636.
4. a) G. A. Olah, J. Lukas, J. Am. Chem. Soc. 1967, 89, 4739-4744;
5. b) G. A. Olah, G. K. S. Prakash, J. Sommer, Superacids, Wiley, New York, 1985.
6. S. Delavarenne, M. Simon, M. Fauconet, J. Sommer, J. Am. Chem. Soc. 1989, 111, 383-384.
7. S. Delavarenne, M. Simon, M. Fauconet, J. Sommer, J. Chem. Soc. Chem. Commun. 1989, 1049-1050.
8. a) J. Sommer, J. Bukala, Acc. Chem. Res. 1993, 26, 370-376;
9. b) J. Sommer, J. Bukala, M. Hachoumy, R. Jost, J. Am. Chem. Soc. 1997, 119, 3274-3279;
10. c) J. Sommer, M. Hachoumy, J. C. Culmann, J. Bukala, New J. Chem. 1997, 21, 939.
11. H. Koch, Brennstoff-Chemie 1955, 36, 321-328.
12. H. Bahrmann, in New Syntheses with Carbon Monoxide (Ed.: J. Falbe), Springer, Berlin, 1980, p. 372.
13. a) A. G. Stepanov, M. V. Luzgin, V. N. Romannikov, K. I. Zamaraev, J. Am. Chem. Soc. 1995, 115, 3615-3616;
14. b) A. G. Stepanov, M. V. Luzgin, V. N. Romannikov, V. N. Sidelnikov, K. I. Zamaraev, J. Catal. 1996, 116, 411-421.
15. J. Sommer, M. Hachoumy, F. Garin, J. Am. Chem. Soc. 1995, 117, 1135-1136.
16. a) J. Sommer, D. Habermacher, M. Hachoumy, R. Jost, A. Reynaud, Appl. Catal. 1996, 146, 193-205;
17. b) J. Sommer, R. Jost, M. Hachoumy, Catal. Today 1997, 38, 309;
18. c) A. G. Stepanov, H. Ernst, D. Freude, Catal. Lett. 1998, 54, 1-4.
19. J. Engelhardt, W. K. Hall, J. Catal. 1995, 151, 1-9.
20. J. Sommer, D. Habermacher, R. Jost, A. Sassi, A. G. Stepanov, M. V. Luzgin, D. Freude, H. Ernst, J. Martens, J. Catal. 1999, 181, 265-270.
21. F. C. Jentoft, B. C. Gates, Topics in Catalysis 1997, 4, 1-13.
22. B. W. Wojciechowski, A. Corma, Catalytic Cracking: Catalysts, Chemistry and Kinetics; Dekker, New York, 1986.
23. A. G. Stepanov, V. N. Sidelnikov, K. I. Zamaraev, Chem. Eur. J. 1996, 2, 157-167.
24. 13C NMR Spectroscopy, Methods and Applications in Organic Chemistry, Verlag Chemie, Weinheim, 1978, p. 159.
25. M. W. Anderson, J. Klinowski, J. Am. Chem. Soc. 1990, 112, 10-16.
26. E. J. Munson, N. D. Lazo, M. E. Moellenhoff, J. F. Haw, J. Am. Chem. Soc. 1991, 113, 2783-2784.
27. M. V. Luzgin, V. N. Romannikov, A. G. Stepanov, K. I. Zamaraev, J. Am. Chem. Soc. 1996, 118, 10890-10891.
28. [9, 18-20] and Figure 1b.
29. 3). See: F. A. Bovey, NMR Data Tables for Organic Compounds, Vol. 1, Wiley, New York, 1967.
30. a) V. M. Mastikhin, O. B. Lapina, React. Kinet. Catal. Lett. 1979, 11, 353-358;
31. b) K. F. M. G. J. Sholle, A. P. M. Kentgens, W. S. Veeman, P. Frenken, G. P. M. van der Velden, J. Phys. Chem. 1984, 88, 5-8;
32. c) M. Hunger, D. Freude, H. Pfeifer, J. Chem. Soc. Faraday Trans. 1991, 87, 657-662.
33. W. O. Haag, R. M. Dessau, in Proceedings 8th Intern. Congress on Catalysis, Berlin, 1984, 2, p. 305, Dechema, Franfkurt am Main.
34. D. H. Marr, Org. Magn. Reson. 1981, 15, 22.
35. J. Bendiera, Y. Ben Taarit, Appl. Catal. 1990, 62, 309-316.
36. Y. Souma, H. Sano, J. Iyoda, J. Org. Chem. 1973, 38, 2016-2020.
37. Y. W. Bizreh, B. C. Gates, J. Catal. 1984, 88, 240-243.
38. C. Stefanadis, B. C. Gates, W. O. Haag, J. Mol. Catal. 1991, 67, 363-367.
39. A. Corma, P. J. Miguel, A. V. Orchilles, J. Catal. 1994, 145, 171-180.
40. G. A. Olah, Angew. Chem. 1973, 85, 183-225; Angew. Chem. Int. Ed. Engl. 1973, 12, 173-212.
41. G. A. Olah, Angew. Chem. 1973, 85, 183-225; Angew. Chem. Int. Ed. Engl. 1973, 12, 173-212.
42. 298 of pentanoic (or isopentanoic) acid, see: D. R. Stull, E. F. Westrum, G. C. Sinke, The Chemical Thermodynamics of Organic Compounds, Wiley, New York, 1969;
43. 298 of pentanoic (or isopentanoic) acid, see: D. R. Stull, E. F. Westrum, G. C. Sinke, The Chemical Thermodynamics of Organic Compounds, Wiley, New York, 1969;
44. 298 of pentanoic (or isopentanoic) acid, see: D. R. Stull, E. F. Westrum, G. C. Sinke, The Chemical Thermodynamics of Organic Compounds, Wiley, New York, 1969;
45. 4(g). The thermodynamic parameters of IBA was taken from: J. Konicek, I. Wadsö, Acta Chem. Scand. 1970, 24, 2612-2616; I. B. Rabinovich, B. V. Lebedev, T. I. Melenteva, Visokomol. Soed. 1967, A9, 1699-1705 (in Russian); D. R. Stull, E. F. Westrum, G. C. Sinke, The Chemical Thermodynamics of Organic Compounds; Wiley, New York, 1969.
46. 4(g). The thermodynamic parameters of IBA was taken from: J. Konicek, I. Wadsö, Acta Chem. Scand. 1970, 24, 2612-2616; I. B. Rabinovich, B. V. Lebedev, T. I. Melenteva, Visokomol. Soed. 1967, A9, 1699-1705 (in Russian); D. R. Stull, E. F. Westrum, G. C. Sinke, The Chemical Thermodynamics of Organic Compounds; Wiley, New York, 1969.
47. 4(g). The thermodynamic parameters of IBA was taken from: J. Konicek, I. Wadsö, Acta Chem. Scand. 1970, 24, 2612-2616; I. B. Rabinovich, B. V. Lebedev, T. I. Melenteva, Visokomol. Soed. 1967, A9, 1699-1705 (in Russian); D. R. Stull, E. F. Westrum, G. C. Sinke, The Chemical Thermodynamics of Organic Compounds; Wiley, New York, 1969.
48. T. M. Duncan, R. W. Vaughan, J. Catal. 1981, 67, 49-70.
49. N. D. Lazo, D. K. Murray, M. L. Kieke, J. F. Haw, J. Am. Chem. Soc. 1992, 114, 8552-8559.
50. P. J. F. de Rege, J. A. Gladysz, I. T. Horvárth, Science 1997, 276, 776.
51. E. G. Derouane, S. B. Abdul Hamid, I. I. Ivanova, N. Blom, P. E. Hojlund-Nielsen, J. Mol. Catal. 1994, 86, 371-400.
52. F. G. Oliver, E. J. Munson, J. F. Haw, J. Phys. Chem. 1992, 96, 8106-8111.
53. S. Rajadurai, A. Selvanathan, V. M. Selvi, Mater. Chem. Phys. 1985, 12, 483-489.
54. Y. Takemura, A. Nakamura, H. Taguchi, Ind. Eng.Chem. Prod. Res. Dev. 1985, 24, 213-215.
55. 13C CP/MAS NMR spectra more strongly bound and less mobile species (e.g. carboxylic acids, aromatics) prevail. See, for example: J. F. Haw, B. R. Richardson, I. S. Oshio, N. D. Lazo, J. A. Speed, J. Am. Chem. Soc. 1989, 111, 2052-2058; ref. [9].
56. M. Saunders, P. Vogel, E. L. Hagen, J. Rosenfeld, Acc. Chem. Res. 1973, 6, 53.
57. P. C. Myhre, C. S. Yannoni, J. Am. Chem. Soc. 1981, 103, 230-232.
58. A. G. Stepanov, M. V. Luzgin, V. N. Romannikov, K. I. Zamaraev, Catal. Lett. 1994, 24, 271-284.
59. V. N. Romannikov, V. M. Mastikhin, S. Hočevar, B. Držaj, Zeolites 1983, 3, 311-320.
60. R. K. Harris in Nuclear Magnetic Resonance Spectroscopy. A Physicochemical View, Pitman, London, 1983, p. 107.