Skip to main content
Log in

The Continuous Synthesis of 2-(2'-Hydroxy-5'-Methylphenyl)Benzotriazole over Cu/γ-Al2O3

  • Published:
Kinetics and Catalysis Aims and scope Submit manuscript

Abstract

The samples of 20% Cu/γ-Al2O3, 20% Co/γ-Al2O3 and 20% Ni/γ-Al2O3 were prepared as hydrogenation catalysts for continuous synthesis of 2-(2'-hydroxy-5'-methylphenyl)benzotriazole. The best yield (86.62%) was afforded by the 20% Cu/γ-Al2O3 catalyst. The characterizations results obtained for the 20% Cu/γ-Al2O3 sample confirmed that Cu particles are evenly distributed over the surface of γ-Al2O3. A reduction of acid sites in the catalyst favored the selectivity to 2-(2'-hydroxy-5'-methylphenyl)benzotriazole. Furthermore, the effect of Cu content, reaction temperature, hydrogen pressure and liquid hourly space velocity was studied. Finally, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole in 86.62% yield was attained under the optimized conditions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.

Similar content being viewed by others

REFERENCES

  1. Catalán, J., de Paz, J.L.G., Torres, R.M., and Tornero, J.D., J. Chem. Soc., Faraday Trans., 1997, vol. 93, p. 1691.

    Article  Google Scholar 

  2. Crawford, J.C., Prog. Polym. Sci., 1999, vol. 24, p. 7.

    Article  CAS  Google Scholar 

  3. Jpn. Patent 10 045 728, 1998.

  4. WO Patent 2 007 036 948, 2007.

  5. Jpn. Patent 2 004 099 448, 2004.

  6. Gostikin, V.P., Lefedova, O.V., Marochko, A.V., and Nemtseva, M.P., Kinet. Catal., 1998, vol. 39, p. 690.

    CAS  Google Scholar 

  7. Koutsimpelis, A.G., Screttas, C.G., and Igglessi-Markopoulou, O., Heterocycles, 2005, vol. 65, p. 1393.

    Article  CAS  Google Scholar 

  8. Jin, J., Wen, Z., Long, J., Wang, Y. M., Matsuura, T., and Meng, J.B., Synth. Commun., 2000, vol. 30, p. 829.

    Article  CAS  Google Scholar 

  9. Farkas, R., Torincsi, M., Kolonits, P., Fekete, J., Alonso, O.J., and Novak, L., Cent. Eur. J. Chem., 2010, vol. 8, p. 300.

    CAS  Google Scholar 

  10. Whitmore, W.F., and Revukas, A.J., J. Am. Chem. Soc., 1940, vol. 62, p. 1687.

    Article  CAS  Google Scholar 

  11. Rosevear, J., and Wilshire, J.F.K., Aust. J. Chem., 1982, vol. 35, p. 2089.

    Article  CAS  Google Scholar 

  12. Lefedova, O.V., and Nemtseva, M.P., Russ. J. Appl. Chem., 2012, vol. 85, p. 1128.

    Article  CAS  Google Scholar 

  13. Zuenko, M.A., Nemtseva, M.P., Lefedova, O.V., and Gladkova, E.V., Russ. J. Phys. Chem., 2006, vol. 80, p. 164.

    Article  CAS  Google Scholar 

  14. Lefedova, O.V., Nikolaev, V.N., and Nemtseva, M.P., Russ. J. Phys. Chem., 2003, vol. 77, p. 1059.

    Google Scholar 

  15. US Patent 3230194, 1966.

  16. Fr. Patent 2292708, 1976.

  17. Baik, W., Park, T.H., Kim, B.H., and Jun, Y.M., J. Org. Chem., 1995, vol. 60, p. 5683.

    Article  CAS  Google Scholar 

  18. FRG Patent 3 731 860, 1988.

  19. US Patent 3 018 269, 1962.

  20. CA Patent 1 154 779, 1983.

  21. EP Patent 380 839, 1990.

  22. FRG Patent 2 620 970, 1976.

  23. FRG Patent 2 455 155, 1975.

  24. Lefedova, O.V., Gostikin, V.P., and Ulitin, M.V., Russ. J. Phys. Chem., 2001, vol. 75, p. 1433.

    Google Scholar 

  25. Lefedova, O.V., Gostikin, V.P., and Nemtseva, M.P., Russ. J. Phys. Chem., 2001, vol. 75, p. 62.

    Google Scholar 

  26. Nemtseva, M.P. and Lefedova, O.V., Kinet. Catal., 1994, vol. 35, p. 547.

    CAS  Google Scholar 

  27. Wang, B.W., Fang, W.W., Si, L.L., Li, Y., Yan, X.L., Chen, L.G., and Wang, S.T., ACS Sustainable Chem. Eng., 2015, vol. 3, p. 1890.

    Article  CAS  Google Scholar 

  28. Nemtseva, M.P., Lefedova, O.V., Gostikin, V.P., and Zuenko, M.A., Russ. J. Phys. Chem., 2003, vol. 77, p. 917.

    Google Scholar 

  29. Wang, B.W., Si, L.L., Yuan, Y.Y., Li, Y., Chen, L.G., and Yan, X.L., RSC Adv., 2016, vol. 6, p. 16766.

    Article  CAS  Google Scholar 

  30. Si, L.L., Wang, B.W., Chen, S.P., Hou, J.R., Yan, X.L., Li, Y., and Chen, L.G., Catal. Commun., 2017, vol. 90, p. 35.

    Article  CAS  Google Scholar 

  31. Kong, X.J. and Chen, L.G., Catal. Commun., 2014, vol. 57, p. 45.

    Article  CAS  Google Scholar 

  32. Kong, X.J., Lai, W.C., Tian, J., Li, Y., Yan, X.L., and Chen, L., ChemCatChem., 2013, vol. 5, p. 2009.

    Article  CAS  Google Scholar 

  33. Kong, X.J. and Chen, L.G., Appl. Catal., A, 2014, vol. 476, p. 34.

  34. Mierczynski, P., Ciesielski, R., Zakrzewski, M., Dawid, B., Mosinska, M., Kedziora, A., Maniukiewicz, W., Dubkov, S., Gromov, D., Szynkowska, M., Witonska, I., Shtyka, O., and Maniecki, T., Kinet. Catal., 2018, vol. 59, p. 509.

    Article  CAS  Google Scholar 

  35. Srivastava, S., Jadeja, G.C., and Parikh, J., J. Mol. Catal. A: Chem., 2017, vol. 426, p. 244.

    Article  CAS  Google Scholar 

  36. Artyukha, E.A., Nuzhdin, A.L., Bukhtiyarova, G.A., Derevyannikova, E.A., Gerasimov, E.Y., Gladkii, A.Y., and Bukhtiyarov, V.I., Kinet. Catal., 2018, vol. 59, p. 593.

    Article  CAS  Google Scholar 

  37. Guo, H.T., Gao, R.X., Sun, M.M., Guo, H., Wang, B.W., and Chen, L.G., ChemSusChem, 2019, vol. 12, p. 487.

    Article  CAS  Google Scholar 

  38. Kumar, P.S., Korving, L., Keesman, K.J., van Loosdrecht, M.C.M., and Witkamp, G.J., Chem. Eng. J., 2019, vol. 358, p. 160.

    Article  Google Scholar 

  39. Markov, P.V., Mashkovsky, I.S., Bragina, G.O., Warna, J., Gerasimov, E.Y., Bukhtiyarov, V.I., Stakheev, A.Y., and Murzin, D.Y., Chem. Eng. J., 2019, vol. 358, p. 520.

    Article  CAS  Google Scholar 

  40. Wang, B.W., Si, L.L., Geng, J.Y., Su, Y.H., Li, Y., Yan, X.L., and Chen, L.G., Appl. Catal., B, 2017, vol. 204, p. 316.

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by the National Natural Science Foundation of China (grant no. 21 808 161).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to B. Wang or Y. Li.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yan, L., Si, L., Tao, Q. et al. The Continuous Synthesis of 2-(2'-Hydroxy-5'-Methylphenyl)Benzotriazole over Cu/γ-Al2O3. Kinet Catal 60, 635–641 (2019). https://doi.org/10.1134/S0023158419050124

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0023158419050124

Keywords:

Navigation