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One-step synthesis of N-methylaniline by hydroalkylation of nitrobenzene over oxide catalysts

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Abstract

The reaction of nitrobenzene hydroalkylation with methanol forming N-methylaniline as the main product has been studied. Alumina modified with copper and chromium compounds deposited by incipient wetness impregnation has been examined as the catalyst. It has been shown that the reductive alkylation of nitrobenzene with methanol is preferable to conduct at a temperature of 250°C, a feed weight hourly space velocity of 1 to 2 h−1, a methanol: nitrobenzene molar ratio of 3 to 4, and hydrogen: nitrobenzene molar ratio of 3–6. It has been found that promotion of the copper-containing catalyst with chromium leads to enhancement of the catalyst activity and facilitates an increase in selectivity for N-methylaniline.

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References

  1. P. S. Niphadkar, P. N. Joshi, H. R. Gurav, et al., J. Catal. Lett. 133, 175 (2009).

    Article  CAS  Google Scholar 

  2. V. D. Stytsenko, T. D. Khyu, and V. A. Vinokurov, Kinet. Katal. 46(3), 402 (2005).

    Article  Google Scholar 

  3. New Chemical Engineer’s Handbook: Raw Materials and Products in Organic and Inorganic Chemicals Industry, Ed. by Yu. V. Pokonova and V. I. Starkhov (NPO Professional, St. Petersburg, 2007), p. 988 [in Russian].

    Google Scholar 

  4. P. Sangeetha, P. Seetharamulu, K. Shanthi, et al., J. Mol. Catal. A: Chem. 273, 244 (2007).

    Article  CAS  Google Scholar 

  5. P. Sangeetha, K. Shanthi, K. S. Rama Rao, et al., Appl. Catal. A: Gen. 353, 160 (2009).

    Article  CAS  Google Scholar 

  6. Y. Xiang, X. Li, Ch. Lu, et al., Appl. Catal. A: Gen. 375, 289 (2010).

    Article  CAS  Google Scholar 

  7. N. Bouchenafa-Saïb, P. Grange, P. Verhasselt, et al., Appl. Catal. A: Gen. 286, 167 (2005).

    Article  Google Scholar 

  8. F. Zhao, Y. Ikushima, and M. Arai, J. Catal. 224, 479 (2004).

    Article  CAS  Google Scholar 

  9. Ch.-H. Li, Zh.-X. Yu, K.-F. Yao, et al., J. Mol. Catal. A: Chem. 226, 101 (2005).

    Article  CAS  Google Scholar 

  10. H. Liu, G. Lu, Y. Guo, et al., J. Colloid Interface Sci. 346, 486 (2010).

    Article  CAS  Google Scholar 

  11. X. Meng, H. Cheng, Y. Akiyama, et al., J. Catal. 264, 1 (2009).

    Article  CAS  Google Scholar 

  12. J. Relvas, R. Andrade, F. G. Freire, Catal. Today 133–135, 828 (2008).

    Article  Google Scholar 

  13. N. Mahata, A. F. Cunha, J. J. M. Órfão, and J. L. Figueiredo, Appl. Catal. A: Gen. 351, 204 (2008).

    Article  CAS  Google Scholar 

  14. Sh. Diao, W. Qian, G. Luo, et al., Appl. Catal. A: Gen. 286, 30 (2005).

    Article  CAS  Google Scholar 

  15. M. Vijayaraj and C. S. Gopinath, J. Catal. 226, 230 (2004).

    Article  CAS  Google Scholar 

  16. M. Vijayaraj, B. Murugan, Sh. Umbarkar, et al., J. Mol. Catal. A: Chem. 231, 169 (2005).

    Article  CAS  Google Scholar 

  17. K. Nishamol, K. S. Rahna, and S. Sugunan, J. Mol. Catal. A: Chem. 209, 89 (2004).

    Article  CAS  Google Scholar 

  18. A. C. Bayer, Ch. U. Pittman, L. Wang, et al., US Patent No. 5030759.

  19. N. Nagaraju and G. Kuriakose, New J. Chem. 27, 765 (2003).

    Article  CAS  Google Scholar 

  20. R. Luque, J. M. Campelo, D. Luna, et al., J. Mol. Catal. A: Chem. 269, 190 (2007).

    Article  CAS  Google Scholar 

  21. M. K. Starovoitov, Yu. D. Batrin, T. V. Rudakova, et al., RU Patent No. 2152382.

  22. B. N. Gorbunov, S. K. Slepov, S. V. Vlasov, et al., RU Patent, No. 2275353.

  23. Yu. D. Batrin, Yu. T. Nikolaev, and M. I. Yakushkin, RU Patent No. 2135460.

  24. M.-F. Luo, P. Fang, M. He, and Y. -L. Xie, J. Mol. Catal. A: Chem. 239, 243 (2005).

    Article  CAS  Google Scholar 

  25. R. Kam, C. Selomulya, R. Amal, and J. Scott, J. Catal. 273 73 (2010).

    Article  CAS  Google Scholar 

  26. W. Fu, Zh. Bao, W. Ding, et al., Catal. Commun. 12, 505 (2011).

    Article  CAS  Google Scholar 

  27. N. A. S. Amin, E. F. Tan, and Z. A. Manan, Appl. Catal. B: Environ. 43, 57 (2003).

    Article  CAS  Google Scholar 

  28. F.-W. Chang, W.-Y. Kuo, and H.-Ch. Yang, Appl. Catal. A: Gen. 288, 53 (2005).

    Article  CAS  Google Scholar 

  29. P. Mohanty, K. K. Pant, J. Parikh, and D. K. Sharma, Fuel Process. Technol. 92, 600 (2011).

    Article  CAS  Google Scholar 

  30. L. Zhang, Y. Zhao, H. Dai, et al., Catal. Today 131, 42 (2008).

    Article  CAS  Google Scholar 

  31. F. Ayari, M. Mhamdi, D. P. Debecker, et al., J. Mol. Catal. A: Chem. 339, 8 (2011).

    Article  CAS  Google Scholar 

  32. B. W. Wojciechowski, Can. J. Chem. Eng. 46, 48 (1968).

    Article  CAS  Google Scholar 

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Correspondence to M. V. Belova.

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Original Russian Text © M.V. Belova, O.A. Ponomareva, I.I. Ivanova, 2014, published in Neftekhimiya, 2014, Vol. 54, No. 6, pp. 448–454.

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Belova, M.V., Ponomareva, O.A. & Ivanova, I.I. One-step synthesis of N-methylaniline by hydroalkylation of nitrobenzene over oxide catalysts. Pet. Chem. 54, 438–444 (2014). https://doi.org/10.1134/S0965544114060024

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  • DOI: https://doi.org/10.1134/S0965544114060024

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