Catalytic carbon-carbon and carbon-hydrogen bond cleavage in lower alkanes. Low-temperature hydroxylations and hydroxycarbonylations with dioxygen as the oxidant

Journal of the American Chemical Society

Volumn 118, Issue 19, 1996, Pages 4574-4580

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

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE;

ARTICLE; DRUG DEGRADATION; HYDROXYLATION; OXIDATION; REACTION ANALYSIS; TEMPERATURE;

EID: 0029996718     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953670r     Document Type: Article

References (54)

1. Preliminary account of conversion of methane to acetic acid in aqueous medium: Lin, M.; Sen, A. Nature 1994, 368, 613.
2. (a) Nishiaguchi, T., Nakata, K., Takaki, K.; Fujiwara, Y. Chem. Lett. 1992, 1141.
3. (b) Goldstein, A. S.; Drago, R. S. J. Chem. Soc., Chem. Commun. 1991, 21.
4. (c) Kao, L.-C.; Hutson, A. C., Sen, A. J. Am. Chem. Soc. 1991, 113, 700. Examples at higher temperatures (∼200 °C):
5. (d) Vargaftik, M. N.; Stolarov, I. P.; Moiseev, I. I. J. Chem. Soc., Chem. Commun. 1990, 1049. (e) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Loffler, 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.
6. (d) Vargaftik, M. N.; Stolarov, I. P.; Moiseev, I. I. J. Chem. Soc., Chem. Commun. 1990, 1049. (e) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Loffler, 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.
7. (d) Vargaftik, M. N.; Stolarov, I. P.; Moiseev, I. I. J. Chem. Soc., Chem. Commun. 1990, 1049. (e) Periana, R. A.; Taube, D. J.; Evitt, E. R.; Loffler, 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.
8. (a) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647.
9. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015
10. (c) Chiang, H. J.; Liu, C.-S. J. Organomet. Chem. 1993, 458, 167.
11. (d) Gozin, M., Aizenberg, M.; Liou, S.-Y.; Weisman, A.; Ben-David, Y , Milstein, D. Nature 1994, 370, 42.
12. (e) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699.
13. (f) Rondon, D.; Chaudret, B.; He, X.-D., Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671.
14. (g) Hartwig, J F., Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717.
15. (h) Bunel, E.; Burger, B. J., Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976.
16. (i) Crabtree, R. H., Dion, R. P., Gibboni, D. J., McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc 1986, 108, 7222.
17. (j) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679.
18. (k) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471.
19. (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.
20. (b) Masters, C. D.; Root, D. H.; Attanasi, E. D. Science 1991, 253, 146.
21. (c) Starr, C.; Searl, M. F.; Alpert, S. Science 1992, 256, 981.
22. Recent reviews: (a) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (c) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (d) Fierro, J. L. G. Catal. Lett. 1993, 22, 67 (e) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183.
23. Recent reviews: (a) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (c) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (d) Fierro, J. L. G. Catal. Lett. 1993, 22, 67 (e) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183.
24. Recent reviews: (a) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (c) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (d) Fierro, J. L. G. Catal. Lett. 1993, 22, 67 (e) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183.
25. Recent reviews: (a) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (c) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (d) Fierro, J. L. G. Catal. Lett. 1993, 22, 67 (e) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183.
26. Recent reviews: (a) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (c) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (d) Fierro, J. L. G. Catal. Lett. 1993, 22, 67 (e) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183.
27. Chem. Eng. News 1994, July 4, 31.
28. (a) Methanol Production and Use; Cheng, W.-H.; Kung, H. H., Eds.; Marcel Dekker: New York, 1994.
29. (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.
30. (a) Acetic Acid and Its Derivatives; Agreda, V. H , Zoeller, J. R., Eds.; Marcel Dekker New, York, 1993.
31. (b) Wagner, F. S. In Kirk-Othmer Encyclopedia of Chemical Technology; Wiley: New York, 1978; Vol. 1, p 124.
32. Review. Forster, D. Adv. Organomet. Chem. 1979, 17, 255.
33. Unzelman, G. H. Oil Gas J. 1991, 89, 44, 62.
34. (a) Sen, A.; Lin, M.; Kao, L.-C.; Hutson, A. C. J. Am. Chem. Soc. 1992, 114, 6385.
35. (b) Luinstra, G. A., Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1993, 115, 3004.
36. (c) Kusch, L. A.; Lavrushko, V. V.; Misharin, Yu, S.; Moravsky, A. P.; Shilov, A. E. Nouv. J. Chim. 1983, 7, 729.
37. CRC Handbook of Chemistry and Physics; Lide, D. R., Ed.; CRC Press: Boca Raton, 1991, (a) p 9-121, (b) p 10-213, (c) p 9-114.
38. CRC Handbook of Chemistry and Physics; Lide, D. R., Ed.; CRC Press: Boca Raton, 1991, (a) p 9-121, (b) p 10-213, (c) p 9-114.
39. CRC Handbook of Chemistry and Physics; Lide, D. R., Ed.; CRC Press: Boca Raton, 1991, (a) p 9-121, (b) p 10-213, (c) p 9-114.
40. CRC Handbook of Chemistry and Physics; Lide, D. R., Ed.; CRC Press: Boca Raton, 1991, (a) p 9-121, (b) p 10-213, (c) p 9-114.
41. Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892.
42. Specific recent example: van Koppen, P. A. M.; Bowers, M. T.; Fisher, E. R.; Armentrout, P. B. J. Am. Chem. Soc. 1994, 116, 3780.
43. Review on fragmentation of alkoxy radicals: Kochi, J. K. In Free Radicals: Wiley New York, 1973; Vol. II. p 665.
44. Lin, M.; Sen, A. J. Am. Chem. Soc. 1992, 114, 7307.
45. Baker, E. C.; Hendriksen, D. E.; Eisenberg, R. J. Am. Chem. Soc. 1980, 102, 1020.
46. Hjortkjaer, J.; Jensen, V. W. Ind. Eng. Chem., Prod. Res. Dev. 1976, 15, 46.
47. Reviews: (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. (b) Mansuy, D.; Battioni, P. In Bioinorganic Catalysis; Reedijk, J., Ed.; Marcel Dekker: New York, 1993; p 395
48. Reviews: (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. (b) Mansuy, D.; Battioni, P. In Bioinorganic Catalysis; Reedijk, J., Ed.; Marcel Dekker: New York, 1993; p 395
49. Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
50. Representative examples: (a) Otake, M. Chemtech 1995, No. 9, 36. (b) Miyake, T.; Hamada, M.; Sasaki, Y.; Oguri, M. Appl. Catal. A: General 1995, 131, 33. (c) Teranishi, T.; Toshima, N. J. Chem. Soc., Dalton Trans. 1995, 979. (d) Wang, Y.; Otsuka, K. J. Catal. 1995, 155, 256. (e) Benvenuto, M. A.; Sen, A. J. Chem. Soc., Chem. Commun. 1993, 970.
51. Representative examples: (a) Otake, M. Chemtech 1995, No. 9, 36. (b) Miyake, T.; Hamada, M.; Sasaki, Y.; Oguri, M. Appl. Catal. A: General 1995, 131, 33. (c) Teranishi, T.; Toshima, N. J. Chem. Soc., Dalton Trans. 1995, 979. (d) Wang, Y.; Otsuka, K. J. Catal. 1995, 155, 256. (e) Benvenuto, M. A.; Sen, A. J. Chem. Soc., Chem. Commun. 1993, 970.
52. Representative examples: (a) Otake, M. Chemtech 1995, No. 9, 36. (b) Miyake, T.; Hamada, M.; Sasaki, Y.; Oguri, M. Appl. Catal. A: General 1995, 131, 33. (c) Teranishi, T.; Toshima, N. J. Chem. Soc., Dalton Trans. 1995, 979. (d) Wang, Y.; Otsuka, K. J. Catal. 1995, 155, 256. (e) Benvenuto, M. A.; Sen, A. J. Chem. Soc., Chem. Commun. 1993, 970.
53. Representative examples: (a) Otake, M. Chemtech 1995, No. 9, 36. (b) Miyake, T.; Hamada, M.; Sasaki, Y.; Oguri, M. Appl. Catal. A: General 1995, 131, 33. (c) Teranishi, T.; Toshima, N. J. Chem. Soc., Dalton Trans. 1995, 979. (d) Wang, Y.; Otsuka, K. J. Catal. 1995, 155, 256. (e) Benvenuto, M. A.; Sen, A. J. Chem. Soc., Chem. Commun. 1993, 970.
54. Representative examples: (a) Otake, M. Chemtech 1995, No. 9, 36. (b) Miyake, T.; Hamada, M.; Sasaki, Y.; Oguri, M. Appl. Catal. A: General 1995, 131, 33. (c) Teranishi, T.; Toshima, N. J. Chem. Soc., Dalton Trans. 1995, 979. (d) Wang, Y.; Otsuka, K. J. Catal. 1995, 155, 256. (e) Benvenuto, M. A.; Sen, A. J. Chem. Soc., Chem. Commun. 1993, 970.