Production of hydrogen peroxide via aerobic oxidation of alcohols catalyzed by N-hydroxyphthalimide

Organic Process Research and Development

Volumn 4, Issue 2, 2000, Pages 94-97

  Iwahama, Takahiro ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034391117     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op990082f     Document Type: Article

References (29)

1. Hess, W. T. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Howe-Grant, M., Eds., John Wily and Sons: New York, 1995; Vol. 13, p 988.
2. (b) Strukul, G. Catalytic Oxidation with Hydrogen Peroxide as Oxidant; Kluwer: Dordrecht, 1992.
3. Hess, W. T. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Howe-Grant, M., Eds., John Wily and Sons: New York, 1995; Vol. 13, pp 986-988.
4. Gelbein, A. P. CHEMTECH 1998, 28, 1.
5. (b) Huckins, H. A. CHEMTECH 1999, 29, 2.
6. Hess, W. T. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Howe-Grant, M., Eds., John Wily and Sons: New York, 1995; Vol. 13, pp 967-976.
7. Hess, W. T. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Howe-Grant, M., Eds., John Wily and Sons: New York, 1995; Vol. 13, pp 976-977.
8. (b) Goor, G.; Kunkel, W. In Ullmann's Encyclopedia of Industrial Chemistry, 5th ed.; Elvers, B., Hawkins, S., Ravenscroft, M., Schulz, G., Eds., VCH: Weinheim, 1989; Vol. A 13, p 457.
9. Ishii, Y.; Nakayama, K.; Takeno, M.; Sakaguchi, S.; Iwahama, T.; Nishiyama, Y. J. Org. Chem. 1995, 60, 3934.
10. (b) Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520.
11. Yoshino, Y.; Hayashi, Y.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1997, 62, 6810.
12. Sakaguchi, S.; Kato, S.; Iwahama, T.; Ishii, Y. Bull. Chem. Soc. Jpn. 1998, 71, 1237.
13. (e) Iwahama, T.; Syojyo, K.; Sakaguchi, S.; Ishii, Y. Org. Process Res. Dev. 1998, 2, 255.
14. (f) Sakaguchi, S.; Takase, T.; Iwahama, T.; Ishii, Y. Chem. Commun. 1998, 2037 and references therein.
15. Iwahama, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 9059.
16. Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 1999, 727.
17. A part of NHPI was found to be converted into phthalimide during the reaction. After the evaporation of AcOEt, NHPI and phthalimide were isolated by filtration and then washed with cold ether. Treatment of the recovered phthalimide with hydroxylamine gave the NHPI in almost quantitative yield.
18. Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
19. Haber, F.; Weiss, J. Proc. R. Soc. London, Ser. A. 1934, 747, 332.
20. (b) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
21. 2: Goor, G.; Kunkel, W. In Ullmann's Encyclopedia of Industrial Chemistry, 5th ed.; Elvers, B., Hawkins, S., Ravenscroft, M., Schulz, G., Eds., VCH: Weinheim, 1989; Vol. A 13, pp 461-463.
22. 2 (71% conversion and 85% selectivity) comparable to those obtained by the Arco process. Thus, from the safety point of view, this oxidation method has great advantages in the chemical industry.
23. Landau, R.; Sullivan, G. A.; Brown, D. CHEMTECH 1979, 602.
24. Brown, N.; Roedel, M. J.; Anderson, A. W.; Schweitzer, C. E. J. Am. Chem. Soc. 1955, 77, 1756.
25. (b) Kharasch, M. S.; Sosnovsky, G. J. Org. Chem. 1958, 23, 1322.
26. De La Mare, H. E.; Kochi, J. K.; Rust, F. F. J. Am. Chem. Soc. 1963, 85, 1437.
27. Sauer, M. C. V.; Edwards, J. O. J. Phys. Chem. 1971, 75, 3377.
28. (e) Zhou, X.; Lee, Y. N. J. Phy. Chem. 1992, 96, 265.
29. Ricciuti, C.; Coleman, J. E.; Willits, C. O. Anal. Chem. 1955, 27, 405.