Direct liquid-phase sulfonation of methane to methanesulfonic acid by SO3 in the presence of a metal peroxide

Angewandte Chemie - International Edition

Volumn 42, Issue 9, 2003, Pages 1019-1021

  Mukhopadhyay, Sudip ^a   Bell, Alexis T ^a  

^a University of California   (United States)

Author keywords

Alkaline earth metals; C H activation; Methane activation; Peroxides; Sulfonation

Indexed keywords

ACIDITY; CALCIUM COMPOUNDS; PHASE COMPOSITION; SULFONATION;

LIQUID PHASE SULFONATION;

METHANE;

CALCIUM; MESYLIC ACID; METAL; METHANE; PEROXIDE; RADICAL; SULFITE; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; LIQUID;

EID: 0037416413     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390260     Document Type: Article

References (31)

1. a) C. L. Hill, Activation and Functionalization of Alkanes, Wiley, New York, 1989;
2. b) M. G. Axelrod, A. M. Gaffney, R. Pitchai, J. A. Sofranko, Natural Gas Conversion II, Elsevier, Amsterdam, 1994, p. 93;
3. c) C. Starr, M. F. Searl, S. Alpert, Science 1992, 256, 981;
4. d) A. E. Shilov, Activation of Saturated Hydrocarbons by Transition Metal Complexes (Ed.: D. Reidel), Dordrecht, 1984;
5. e) G. A. Olah, A. Molnar, Hydrocarbon Chemistry, Wiley, New York, 1995;
6. f) M. Lin, A. Sen, Nature 1994, 368, 613;
7. g) A. Sen, Acc. Chem. Res. 1998, 31, 550;
8. h) J. A. Labinger, Fuel Process. Technol. 1995, 42, 325;
9. i) R. H. Crabtree, Chem. Rev. 1995, 95, 987;
10. j) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879;
11. k) G. Dyker, Angew. Chem. 1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698;
12. k) G. Dyker, Angew. Chem. 1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698;
13. l) H. D. Gesser, N. R. Hunter, Catal. Today 1998, 42, 183;
14. m) J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507.
15. a) M. Asadullah, T. Kitamura, Y. Fujiwara, Angew. Chem. 2000, 112, 2609; Angew. Chem. Int. Ed. 2000, 39, 2475;
16. a) M. Asadullah, T. Kitamura, Y. Fujiwara, Angew. Chem. 2000, 112, 2609; Angew. Chem. Int. Ed. 2000, 39, 2475;
17. b) E. G. Chepaikin, A. P. Bezruchenko, A. A. Leshcheva, G, N. Boyko, I. V. Kuzmenkov, E. H. Grigoryan, A. E. Shilov, J. Mol. Catal. A 2001, 169, 89;
18. c) R. A. Periana, D. J. Taube, E. R. Evitt, D. G. Loffer, P. R. Wentrcek, G. Voss, T. Masuda, Science 1993, 259, 340;
19. d) R. A. Periana, D. J. Taube, S. Gamble, H. Taube, T. Satoh, H. Fujii, Science 1998, 280, 560;
20. e) R. A. Periana, O. Mirinov, D. J. Taube, S. Gamble, Chem. Commun. 2002, 2376.
21. a) Ullmann's Encyclopedia of Industrial Chemistry, Vol. A25, VCH, Weinheim, 1994, pp. 503-506;
22. b) F. M. Beringer, R. A. Falk, J. Am. Chem. Soc. 1959, 81, 2997;
23. c) H. A. Young, J. Am. Chem. Soc. 1937, 59, 811;
24. d) R. C. Murray, J. Chem. Soc. 1933, 739.
25. N. Basickes, T. E. Hogan, A. Sen, J. Am. Chem. Soc. 1996, 118, 13111.
26. a) L. J. Lobree, A. T. Bell, Ind. Eng. Chem. Res. 2001, 40, 736;
27. b) S. Mukhopadhyay, A. T. Bell, Ind. Eng. Chem. Res. 2002, 41, 5901.
28. Sulfur Trioxide and Oleum: Storage and Handling, Dupont Corporation, Wilmington, DE.
29. Y. Ishii, K, Matsunaka, S. Sakaguchi, J. Am. Chem. Soc. 2000, 122, 7390.
30. 2O and methanol, contained in a capillary placed adjacent to the NMR tube containing the sample, were used as the lock and references. The corresponding chemical shift for MSA was δ = 2.82 ppm to 3.02 ppm, depending on the concentration of MSA in the mixture.
31. 3 (0.1 g) were also added to fuming sulfuric acid (5.67 g).