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Benign oxidants and single-site solid catalysts for the solvent-free selective oxidation of toluene

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Two types of single-site heterogeneous catalysts have been designed so as to facilitate either the side-chain oxidation or ring-hydroxylation of toluene in O2 (solvent-free) or by employing aqueous (H2O2) or organic (cumene hydroperoxide) hydroperoxides in high yield. The use of H2O2 and cumene hydroperoxide in particular, facilitates the ring-hydroxylation of toluene when zeolite-encapsulated metal complexes, such as perhalogenated or tetra-nitro-substituted phthalocyanines, are used as catalysts. Nanoporous, redox molecular sieves, display a higher tendency for the side-chain oxidation of toluene with air as an oxidant, with benzoic acid as the predominant product.

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References

  1. J.M. Thomas R. Raja G. Sankar B.F.G. Johnson D.W. Lewis (2001) Chem. Eur. J. 7 2973 Occurrence Handle1:STN:280:DC%2BD3MvkvFCjtQ%3D%3D Occurrence Handle10.1002/1521-3765(20010716)7:14<2972::AID-CHEM2972>3.0.CO;2-Z

    Article  CAS  Google Scholar 

  2. J.M. Thomas, R. Raja, Chem. Commun. (2001) 675.

  3. J.M. Thomas R. Raja G. Sankar R.G. Bell (2001) Acc. Chem. Res. 34 191 Occurrence Handle1:CAS:528:DC%2BD3MXlvVOisw%3D%3D Occurrence Handle10.1021/ar970020e

    Article  CAS  Google Scholar 

  4. R. Raja and J.M. Thomas, Chem. Commun. (1998) 1841.

  5. J.M. Thomas R. Raja G. Sankar R.G. Bell (1999) Nature 398 227 Occurrence Handle1:CAS:528:DyaK1MXitVGlur8%3D Occurrence Handle10.1038/18417

    Article  CAS  Google Scholar 

  6. J.M. Thomas G. Sankar J.M. Thomas (1999) J. Am. Chem. Soc. 121 11926 Occurrence Handle10.1021/ja9935052

    Article  Google Scholar 

  7. R. Raja P. Ratnasamy (1996) Appl. Catal. A 143 145 Occurrence Handle1:CAS:528:DyaK28XkslCnsrk%3D Occurrence Handle10.1016/0926-860X(96)00077-4

    Article  CAS  Google Scholar 

  8. R. Raja P. Ratnasamy (1997) Catal. Lett. 48 1 Occurrence Handle1:CAS:528:DyaK2sXnsFWhtr0%3D Occurrence Handle10.1023/A:1019054415786

    Article  CAS  Google Scholar 

  9. R. Raja P. Ratnasamy (1997) J. Catal. 170 244 Occurrence Handle1:CAS:528:DyaK2sXmt1aiur4%3D Occurrence Handle10.1006/jcat.1997.1749

    Article  CAS  Google Scholar 

  10. R. Raja C.R. Jacob P. Ratnasamy (1999) Catal. Today 49 171 Occurrence Handle1:CAS:528:DyaK1MXps1Knsw%3D%3D Occurrence Handle10.1016/S0920-5861(98)00421-0

    Article  CAS  Google Scholar 

  11. J.M. Thomas R. Raja D.W. Lewis (2005) Angew. Chem. Int. Ed. Engl. 44 6456 Occurrence Handle1:CAS:528:DC%2BD2MXhtFOqurrJ Occurrence Handle10.1002/anie.200462473

    Article  CAS  Google Scholar 

  12. J.M. Thomas R. Raja (2005) Proc. Natl. Acad. Sci. USA 102 13732 Occurrence Handle1:CAS:528:DC%2BD2MXhtVOqsb3M Occurrence Handle10.1073/pnas.0506907102

    Article  CAS  Google Scholar 

  13. Y. Ishii and S. Sakaguchi, Modern Oxidation Methods, J.-E. Bäckvall (ed.) , (Wiley-VCH, Germany, 2004) p. 119 and references therein.

  14. E. Grochowski, T. Boleslawska and J. Jurezak, Synthesis (1977) 718.

  15. Y. Ishii K. Nakayama M. Takeno S. Sakaguchi T. Iwahama Y. Nishiyama (1995) J. Org. Chem. 60 3934 Occurrence Handle1:CAS:528:DyaK2MXmt12rsb0%3D Occurrence Handle10.1021/jo00118a002

    Article  CAS  Google Scholar 

  16. G.W. Parshall S.D. Ittel (1992) Homogeneous Catalysis EditionNumber2 Wiley New York

    Google Scholar 

  17. C.N. Satterfield (1991) Heterogeneous Catalysis in Industrial Practice McGraw-Hill New York

    Google Scholar 

  18. J. Murzat (1992) Chem. Rev. 92 113 Occurrence Handle10.1021/cr00009a005

    Article  Google Scholar 

  19. L. Fieser M. Fieser (1956) Organic Chemistry EditionNumber3 Reinhold New York

    Google Scholar 

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Raja, R., Thomas, J.M. & Dreyer, V. Benign oxidants and single-site solid catalysts for the solvent-free selective oxidation of toluene. Catal Lett 110, 179–183 (2006). https://doi.org/10.1007/s10562-006-0106-y

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  • DOI: https://doi.org/10.1007/s10562-006-0106-y

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