Skip to main content
SpringerLink
Log in

Studies on Deactivation of Iron Oxide Catalyst in Solvent-Free N-Benzylation of Aniline with Benzyl Chloride

  • Published:
Kinetics and Catalysis Aims and scope Submit manuscript

Abstract

Nano-α-Fe2O3 prepared using acid pickling waste as precursor was found to be an effective catalyst for benzylation aniline with benzyl chloride. However, the formation of a green solution was observed during the solvent-free benzylation. A yellow-green single crystal as a byproduct was recovered from the green reaction mixture and characterized by X-ray single crystal diffraction, 1H NMR, FT-IR and elemental analysis. The results showed that this single crystal was a composite structural complex constructed by [(C6H6–CH2)2NH–C6H6]FeCl4 and [(C6H6–CH2)2NH–C6H6]Cl in equimolar ratio. The formation of the complex led to the deactivation and non-reusability of α-Fe2O3 catalyst for catalyzing solvent-free N-benzylation of aniline with benzyl chloride. The forming mechanism of the crystal was also discussed.

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

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.

Similar content being viewed by others

REFERENCES

  1. Ju, Y. and Varma, R.S., Green Chem., 2004, vol. 6, p. 219.

    Article  CAS  Google Scholar 

  2. Dolle, R.E., Bourdonnec, B.L., Goodman, A.J., Morales, G.A., Thomas, C.J., and Zhang, W.J., Comb. Chem., 2009, vol. 11, p. 739.

    Article  CAS  Google Scholar 

  3. Insaf, S.S. and Witiak, D.T., Synthesis, 1999, vol. 1999, p. 435.

    Article  Google Scholar 

  4. Hamid, M.H.S.A., Allen, C.L., Lamb, G.W., Maxwell, A.C., Maytum, H.C., Watson, A.J.A., and Williams, J.M.J., J. Am. Chem. Soc., 2009, vol. 131, p. 1766.

    Article  CAS  Google Scholar 

  5. Yin, M., He, S., Yu, Z., Wu, K., Wang, L., and Sun, C., Chin. J. Catal., 2013, vol. 34, p. 1534.

    Article  CAS  Google Scholar 

  6. Artamkina, G.A., Ermolina, M.V., and Beletskaya, I.P., Mendeleev Commun., 2003, vol. 13, p. 158.

    Article  Google Scholar 

  7. Fujita, K., Li, Z., Ozeki, N., and Yamaguchi, R., Tetrahedron Lett., 2003, vol. 44, p. 2687.

    Article  CAS  Google Scholar 

  8. Xu, H. and Wolf, C., Chem. Commun., 2009, p. 1715.

  9. Wang, D. and Ding, K., Chem. Commun., 2009, p. 1891.

  10. Gupta, M., Paul, S., and Gupta, R., Chin. J. Catal., 2014, vol. 35, p. 444.

    Article  CAS  Google Scholar 

  11. Xu, H. and Wolf, C., Chem. Commun., 2009, p. 3035.

  12. Tang, H., Wang, H., Lu, B., Zhao, J., and Cai, Q., Mol. Catal., 2017, vol. 431, p. 27.

    Article  CAS  Google Scholar 

  13. Li, X., You, X., Lu, B., Wu, X., Zhao, J., and Cai, Q., Ind. Eng. Chem. Res., 2014, vol. 53, p. 20085.

    Article  CAS  Google Scholar 

Download references

Funding

This research was funded by National Natural Science Foundation of China (grant no. 21 671 050).

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Harbin Normal University, 150025, Harbin, China

    C. Ding, H. Wang, B. Lu, J. Zhao & Q. Cai

Authors
  1. C. Ding
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. H. Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. Lu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. J. Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Q. Cai
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to B. Lu or Q. Cai.

Additional information

Abbreviations: DPA, N-dibenzyl phenyl aminium chloride.

SUPPORTING INFORMATION

SUPPORTING INFORMATION

Table S1.   Selected bond lengths (Å) and bond angles (º) of DPA
Full size table

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ding, C., Wang, H., Lu, B. et al. Studies on Deactivation of Iron Oxide Catalyst in Solvent-Free N-Benzylation of Aniline with Benzyl Chloride. Kinet Catal 61, 768–774 (2020). https://doi.org/10.1134/S0023158420050031

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0023158420050031

Keywords:

Search

Navigation