A highly catalytic bimetallic system for the low-temperature selective oxidation of methane and lower alkanes with dioxygen as the oxidant

Journal of the American Chemical Society

Volumn 119, Issue 26, 1997, Pages 6048-6053

  Lin, Minren ^a   Hogan, Terrence ^a   Sen, Ayusman ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; BUTANE; CARBON MONOXIDE; COPPER CHLORIDE; ETHANE; METAL; METHANE; METHANOL; OXYGEN; PALLADIUM; TRIFLUOROACETIC ACID;

ARTICLE; CATALYSIS; CATALYST; LOW TEMPERATURE; OXIDATION; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 0030788464     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964371k     Document Type: Article

References (61)

1. (a) Axelrod, M. G.; Gaffney, A. M.; Pitchai, R.; Sofranko, J. A. In Natural Gas Conversion II; Curry-Hyde, H. E.; Howe, R. F., Eds.; Elsevier: Amsterdam, 1994; p 93.
2. (b) Masters, C. D.; Root, D. H.; Attanasi, E. D. Science 1991, 253, 146.
3. (c) Starr, C.; Searl, M. F.; Alpert, S. Science 1992, 250, 981.
4. Recent reviews: (a) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995.
5. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987.
6. (c) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325.
7. (d) Fierro, J. L. G. Catal. Lett. 1993, 22, 67.
8. (e) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catal. (London) 1992, 9, 183.
9. Chem. Eng. News 1996, April 8, p 17.
10. (a) Cheng, W.-H.; Kung, H. H., Eds.; Methanol Production and Use; Marcel Dekker: New York, 1994.
11. (b) Wade, L. E.; Gengelbach, R. B.; Trumbley, J. L.; Hallbauer, W. L. In Kirk-Othmer Encyclopedia of Chemical Technology; Wiley: New York, 1981; Vol. 15, p 398.
12. Lin, M.; Hogan, T. E.; Sen, A. J. Am. Chem. Soc. 1996, 118, 4574.
13. Examples of noncatalytic C-C cleavage by metal species under mild conditions: (a) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647.
14. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015.
15. (c) Chiang, H. J.; Liu, C.-S. J. Organomet. Chem. 1993, 458, 167.
16. (d) Gozin, M.; Aizenberg, M.; Liou, S.-Y.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1994, 370, 42.
17. (e) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699.
18. (f) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671.
19. (g) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717.
20. (h) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976.
21. (i) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222.
22. (j) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679.
23. (k) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471.
24. Unzelman, G. H. Oil Gas J. 1991, 89, 44, 62.
25. (a) Yamanaka, I.; Soma, M.; Otsuka, K. Chem. Lett. 1996, 565.
26. (b) Nishiguchi, T.; Nakata, K.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1992, 1141.
27. (c) Goldstein, A. S.; Drago, R. S. J. Chem. Soc., Chem. Commun. 1991, 21.
28. (d) Kao, L.-C.; Hutson, A. C.; Sen, A. J. Am. Chem. Soc. 1991, 113, 700. Examples at higher temperatures (∼200°C):
29. (e) Vargaftik, M. N.; Stolarov, I. P.; Moiseev, I. I. J. Chem. Soc., Chem. Commun. 1990, 1049.
30. (f) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. Also: Snyder, J. C.; Grosse, A. V. U.S. Patent 2,493,038, 1950
31. (f) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Löffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340. Also: Snyder, J. C.; Grosse, A. V. U.S. Patent 2,493,038, 1950
32. . (9) Lin, M.; Sen, A. J. Am. Chem. Soc. 1992, 114, 7307.
33. Sen, A.; Lin, M. U.S. Patent 5,393,922, 1995.
34. Hogan, T.; Simpson, R.; Lin, M.; Sen, A. Catal. Lett. 1996, 40, 95.
35. Reviews on monooxygenases and their synthetic analogs: (a) Valentine, J. S. in Bioinorganic Chemistry; Bertini, I., Gray, H. B., Lippard, S. J., Valentine, J. S., Eds.; University Science Books: Mill Valley, CA, 1994; p 253.
36. (b) Que, L. in Bioinorganic Catalysis; Reedijk, J., Ed.; Marcel Dekker: New York, 1993; p 347.
37. (c) Mansuy, D.; Battioni, P. In Bioinorganic Catalysis; Reedijk, J., Ed.; Marcel Dekker: New York, 1993; p 395.
38. (d) Groh, S. E.; Nelson, M. J. In Selective Hydrocarbon Activation; Davies, J. A., Watson, P. L., Liebman, J. F., Greenberg, A., Eds.; VCH: New York, 1990; p 305.
39. (e) Ortiz de Montellano, P. R. In Cytochrome P-450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1986; p 217.
40. (f) Groves, J. T. J. Chem. Ed. 1985, 62, 928.
41. (g) Guegerich, F. P.; Macdonald, T. L. Acc. Chem. Res. 1984, 17, 9.
42. Gosser, L. W. U.S. Patent 4,681,751, 1987.
43. (a) Jagner, S.; Håkansson, M. Inorg. Chem. 1990, 29, 5241.
44. (b) Busch, M. A.; Franklin, T. C. Inorg. Chem. 1979, 18, 521.
45. (c) Scott, A. F.; Wilkening, L. L.; Rubin, B. Inorg. Chem. 1969, 8, 2533.
46. Lunsford, J. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 970.
47. Reviews: (a) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic: New York, 1981; p 35, 171, 329.
48. (b) Edwards, J. O.; Curci R. In Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Strukul, G., Ed.; Kluwer Academic: Dordrecht, 1992; p 97.
49. Sawyer, D. T.; Sobkowiak, A.; Matsushita, T. Acc. Chem. Res. 1996, 29, 409.
50. CRC Handbook of Chemistry and Physics; Lide, D. R., Ed.; CRC Press: Boca Raton, 1991; pp 9-114.
51. Bakac, A.; Espenson, J. H. J. Chem. Soc., Chem. Commun. 1991, 1497.
52. Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892.
53. (a) Acetic Acid and Its Derivatives; Agreda, V. H., Zoeller, J. R., Eds.; Marcel Dekker: New York, 1993.
54. (b) Wagner, F. S. In Kirk-Othmer Encyclopedia of Chemical Technology; Wiley: New York, 1978; Vol. 1, p 124.
55. (c) Forster, D. Adv. Organomet. Chem. 1979, 17, 255.
56. Hjortkjaer, J.; Jensen, V. W. Ind. Eng. Chem., Prod. Res. Dev. 1976, 15, 46.
57. Representative examples: (a) Otake, M. Chemtech 1995, 36.
58. (b) Miyake, T.; Hamada, M.; Sasaki, Y.; Oguri, M. Appl. Catal. A: General 1995, 131, 33.
59. (c) Teranishi, T.; Toshima, N. J. Chem. Soc., Dalton Trans. 1995, 979.
60. (d) Wang, Y.; Otsuka, K. J. Catal 1995, 155, 256.
61. (e) Benvenuto, M. A.; Sen, A. J. Chem. Soc., Chem. Commun. 1993, 970.