Skip to main content
SpringerLink
Log in

A simple approach for preparation of dinitronaphthalene compounds from the nitration reaction of 1-nitronaphthalene with NO2 as nitration reagent

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A simple method for the preparation of dinitronaphthalene from the nitration reaction of 1-nitronaphthalene with NO2 as nitration reagent under the mild conditions has been successfully developed in this work. The results indicated that Ni(CH3COO)2·4H2O catalyst shows better catalytic performances, and the conversion of 1-nitronaphthalene is 33.10 % with 34.10, 23.56, 19.30, and 3.56 % of the selectivity to 1,5-DNN, 1,3-DNN, 1,4-DNN, and 1,8-DNN, respectively, under the optimal reaction conditions. This is a mild, environmentally benign, and economical method for the preparation of dinitronaphthalene.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Scheme 2

Similar content being viewed by others

References

  1. E.C. Prolingheuer, J.M. Barnes, R. Kopp, E. Seggern, Rubber Plast. News 24, 221–239 (1992)

    Google Scholar 

  2. M.T. Allott, S.M. Singer, US 5599874A (1997)

  3. W.T. Smith, J. Am. Chem. Soc. 71(8), 2855–2856 (1949)

    Article  CAS  Google Scholar 

  4. H.H. Hodgson, A.P. Mahadevan, E.R. Ward, Org. Syn. 111, 52–52 (1960)

  5. G. Steinhoff, H.-J. Sturm, US3506725 (1970)

  6. X.F. Wang, B.H. Xu, X.M. Liu, G.Y. Lou, J. Yang, CN1194972A (1998)

  7. B. Gigante, A.O. Prazeres, M.J. Marcelo-Curto, A. Cornelis, P. Laszlo, J. Org. Chem. 60, 3445–3447 (1995)

    Article  CAS  Google Scholar 

  8. F. Durholz, A. Hamers, J. Heinen, US3998893 (1976)

  9. H.-P. Schal, V.Y. Popkova, B.M. Laskin, A.S. Malin, S.B. Volkova, US 6992230B2 (2006)

  10. M. Brandt, S. Klein, G. Wegener, US 20030171627A1 (2003)

  11. C. Steinlein, G. Wegener, WO 1999012887A1 (1999)

  12. G.C.B. Silva, P. Laszlo, A. Cornelis, D.O.B.M. Vidal, WO 1994019310A1 (1994)

  13. C. Guertler, M. Jautelat, M. Schelhaas, DE 19958389 A1 (2001)

  14. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Org. Prep. Proced. Int. 42, 95–102 (2010)

    Article  CAS  Google Scholar 

  15. M. Brandt, S. Klein, G. Wegener, CN 1442401A (2003)

  16. P. Liu, W. Xiong, X. Wang, K. Huang, F. Hao, L. Wang, H.A. Luo, Regioselective nitration of naphthalene over HZSM-5-supported phosphotungstic acid. Res. Chem. Intermed. (2013). doi:10.1007/s11164-014-1549-1

    Google Scholar 

  17. J.K. Cho, Y.-T. Kim, Y.G. Kim, Y.-S. Lee, S.-Y. Sung, K.-H. Chung, B.-S. Lee, Res. Chem. Intermed. 32, 759–766 (2006)

    Article  CAS  Google Scholar 

  18. H. Suzuki, S. Yonezawa, N. Nonoyama, T. Mori, J. Chem. Soc., Perkin Trans. 1, 2385–2389 (1996)

    Article  Google Scholar 

  19. X. Peng, W. Shi, CN 102827007A (2011)

  20. X. Peng, S. Han, H. Wang, C. Su, Z. Zhu, CN 102827007A (2012)

  21. H. Wang, X. Peng, C. Shi, X. Dong, Y. Tai, H. Liu, Res. Chem. Intermed. 40, 1495–1500 (2014)

    Article  Google Scholar 

  22. G.L. Squadrito, F.R. Fronczek, D.F. Church, W.A. Pryor, J. Org. Chem. 54(3), 548–552 (1989)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful for the financial support for this work by the National Natural Science Foundation of China (21276216), Specialized Research Fund for the Doctoral Program of Higher Education (20124301130001), Scientific Research Fund of Hunan Provincial Education Department (13A096) and Major Science and Technology Projects of Hunan Province (2012FJ1001).

Author information

Authors and Affiliations

  1. School of Chemical Engineering, Xiangtan University, Xiangtan, 411105, People’s Republic of China

    Kuiyi You, Zhongcang Zhou, Jian Jian, Renjie Deng, Pingle Liu, Qiuhong Ai & He’an Luo

  2. National and Local United Engineering Research Center for Chemical Process Simulation and Intensification, Xiangtan University, Xiangtan, 411105, People’s Republic of China

    Kuiyi You, Pingle Liu, Qiuhong Ai & He’an Luo

Authors
  1. Kuiyi You
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhongcang Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jian Jian
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Renjie Deng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Pingle Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Qiuhong Ai
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. He’an Luo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Kuiyi You or He’an Luo.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

You, K., Zhou, Z., Jian, J. et al. A simple approach for preparation of dinitronaphthalene compounds from the nitration reaction of 1-nitronaphthalene with NO2 as nitration reagent. Res Chem Intermed 41, 8307–8315 (2015). https://doi.org/10.1007/s11164-014-1893-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-014-1893-1

Keywords

Search

Navigation