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Vol. 28 No. 3 (2016): Vol 28 Issue 3

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Regioselective Mononitration of Aromatic Compounds with N2O5 by Acidic Ionic Liquids via Continuous Flow Microreactor

https://doi.org/10.14233/ajchem.2016.19374
Jianhua Liu
School of Chemical and Engineering, Nanjing University of Science and Technology, Nanjing, P.R. China
Bindong Li
School of Chemical and Engineering, Nanjing University of Science and Technology, Nanjing, P.R. China
Huan Wang
School of Chemical and Engineering, Nanjing University of Science and Technology, Nanjing, P.R. China

Corresponding Author(s) : Bindong Li

libindong@mail.njust.edu.cn

Asian Journal of Chemistry, Vol. 28 No. 3 (2016): Vol 28 Issue 3

Abstract

We employed N2O5 as highly active nitrating reagents and a host of acidic ionic liquid as catalysts in these reactions which were conducted in a continuous flow microreactor. When we utilized PEG400-DAIL as catalysts, the conversion of toluene was increased to 95.5 % and the yield of mononitration product (o/p ratio reached 1.10) significantly improved to 99 %, meanwhile the reaction time was drastically shortened to 1/120 of the conventional reactor. Nitration in ionic liquids was surveyed using a host of aromatic substrates with similar reactivity. The ionic liquid recycling procedures had also been devised.

Keywords

Aromatic nitration Microreactor N2O5 Ionic liquid
Liu, J., Li, B., & Wang, H. (2015). Regioselective Mononitration of Aromatic Compounds with N2O5 by Acidic Ionic Liquids via Continuous Flow Microreactor. Asian Journal of Chemistry, 28(3), 513–516. https://doi.org/10.14233/ajchem.2016.19374
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References
  1. H.W. Yang, X.F. Qi, L. Wen, C. Lu and G. Cheng, Ind. Eng. Chem. Res., 50, 11440 (2011); doi:10.1021/ie201028d.
  2. S.J. Wang, S.J. Jiang and J. Nie, Adv. Synth. Catal., 351, 1939 (2009); doi:10.1002/adsc.200900243.
  3. G.A. Olah, S.J. Kuhn, S.H. Flood and J.C. Evans, J. Am. Chem. Soc., 84, 3687 (1962); doi:10.1021/ja00878a019.
  4. A.V. Aksenov, A.S. Lyakhovnenko, T.S. Perlova and I.V. Aksenova, Chem. Heterocycl. Compd., 47, 245 (2011); doi:10.1007/s10593-011-0748-6.
  5. K. Smith, S. Liu and G.A. El-Hiti, Ind. Eng. Chem. Res., 44, 8611 (2005); doi:10.1021/ie050047z.
  6. M.E. Kurz, L.T. Yang, E.P. Zahora and R.C. Adams, J. Org. Chem., 38, 2271 (1973); doi:10.1021/jo00953a001.
  7. S. Gong, L. Liu, J. Zhang and Q. Cui, Process Saf. Environ. Prot., 92, 577 (2013); doi:10.1016/j.psep.2013.03.005.
  8. J. Antes, D. Boskovic, H. Krause, S. Loebbecke, N. Lutz, T. Tuercke and W. Schweikert, Trans. IChemE, 81, 760 (2003); doi:10.1205/026387603322302931.
  9. J.M. Zaldivar, C. Barcons, H. Hernandez, E. Molga and T.J. Snee, Chem. Eng. Sci., 47, 2517 (1992); doi:10.1016/0009-2509(92)87086-6.
  10. R. Halder, A. Lawal and R. Damavarapu, Catal. Today, 125, 74 (2007); doi:10.1016/j.cattod.2007.04.002.
  11. K. Jahnisch, V. Hessel, H. Lowe and M. Baerns, Angew. Chem. Int. Ed., 43, 406 (2004); doi:10.1002/anie.200300577.
  12. R.W. Millar and S.P. Philbin, Tetrahedron, 53, 4371 (1997); doi:10.1016/S0040-4020(97)00093-8.
  13. R.R. Bak and A.J. Smallridge, Tetrahedron Lett., 42, 6767 (2001); doi:10.1016/S0040-4039(01)01378-8.
  14. K. Qiao, H. Hagiwara and C.J. Yokoyama, J. Mol. Catal. Chem., 246, 65 (2006); doi:10.1016/j.molcata.2005.07.031.
  15. K. Qiao and C. Yokoyama, Chem. Lett., 33, 808 (2004); doi:10.1246/cl.2004.808.
  16. G. Cheng, X. Duan, X. Qi and C. Lu, Catal. Commun., 10, 201 (2008); doi:10.1016/j.catcom.2008.08.019.
  17. P.-C. Wang and M. Lu, Tetrahedron Lett., 52, 1452 (2011); doi:10.1016/j.tetlet.2011.01.053.
  18. D. Fang, Q.R. Shi, J. Cheng, K. Gong and Z.-L. Liu, J. Appl. Catal. A, 345, 158 (2008); doi:10.1016/j.apcata.2008.04.037.
  19. K.-Q. Zhao, P. Hu, H.-B. Xu and L.-F. Zhang, Chin. Chem. Lett., 20, 479 (2009); doi:10.1002/cjoc.20020200513.
  20. X.-F. Chao, B.-D. Li and M. Wang, Chin. Chem. Lett., 25, 4 (2014).
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