Notes

Synthesis of Azoxybenzenes by Selective Oxidation of Anilines on Titanium Silicate Molecular Sieves

  • Song Yuwan ,
  • Feng Shaojing ,
  • Han Wei ,
  • Xiao Yaping
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  • School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023

Received date: 2018-08-28

  Revised date: 2018-11-13

  Online published: 2018-11-30

Supported by

Project supported by the National Natural Science Foundation of China (Nos.21776139,21302099),the Natural Science Foundation of Jiangsu Province (No.BK20161553),the Natural Science Foundation of Jiangsu Provincial Colleges and Universities (No.16KJB150019).

Abstract

A convenient method for improving the conversion and selectivity of aniline to azoxybenzene by adjusting the ratio of silicon to titanium of TS-1 is reported. Over TS-1 (80), aryl anilines are transformed into the corresponding azoxybenzenes in good yields with H2O2 as the oxidant. The effect of different reaction parameters like molar ratio of H2O2 to aniline, solvent and the activity in catalyst recycling has been studied.

Cite this article

Song Yuwan , Feng Shaojing , Han Wei , Xiao Yaping . Synthesis of Azoxybenzenes by Selective Oxidation of Anilines on Titanium Silicate Molecular Sieves[J]. Chinese Journal of Organic Chemistry, 2019 , 39(4) : 1181 -1186 . DOI: 10.6023/cjoc201808032

References

[1] Suresh, S.; Joseph, R.; Jayachandran, B.; Pol, A. V.; Vinod, M. P.; Sudalai, A.; Sonawane, H. R.; Ravindranathan, T. Tetrahedron Lett. 1995, 51, 11305.
[2] Hwu, J. R.; Das, A. R.; Yang, C. W.; Jiannjyh Huang, A.; Hsu, M. H. Org. Lett. 2005, 7, 3211.
[3] Liu, Y.; Liu, B.; Guo, A.; Dong, Z.; Jin, S.; Lu, Y. Molecules 2011, 16, 3563.
[4] Kluge, R.; Schulz, M.; Liebsch, S. Tetrahedron Lett. 1996, 52, 5773.
[5] Rezaeifard, A.; Jafarpour, M.; Naseri, M. A.; Shariati, R. Dyes Pigm. 2008, 76, 840.
[6] Yang, F.; Wang, Z.; Zhang, X.; Jiang, L.; Li, Y.; Wang, L. ChemCatChem 2015, 7, 3450.
[7] Barak, G.; Sasson, Y. J. Org. Chem. 1989, 54, 3484.
[8] (a) Sonawane, H. R.; Pol, A. V.; Moghe, P. P.; Biswas, S. S.; Shariati, R. Chem. Commun. 1994, 25, 1215.
(b) Gontier, S.; Tuel, A. J. Catal. 1995, 157, 124.
(c) Chang, C. F.; Liu, S. T. J. Mol. Catal. A:Chem. 2009, 299, 121.
(d) Das, D. R.; Talukdar, A. K. ChemistrySelect 2017, 2, 8983.
[9] Ghosh, S.; Acharyya, S. S.; Sasaki, T.; Bal, R. Green Chem. 2015, 17, 1867.
[10] Acharyya, S. S.; Ghosh, S.; Bal, R. ACS Sustainable Chem. Eng. 2014, 2, 584.
[11] Yang, L.; Shi, G.; Ke, X.; Shena, R.; Zhang, L. CrystEngComm 2014, 16, 1620.
[12] For aniline forming polyaniline during the oxidation process, see:(a) Yu, L.; Huang, Y.; Wei, Z.; Ding, Y.; Su, C.; Xu, Q. ChemInform 2016, 47, 8677.
(b) Yu, L.; Han, Z. Mater. Lett. 2016, 184, 312.
(c) Yu, L.; Han, Z.; Ding, Y. Org. Process Res. Dev. 2016, 20, 2124.
(d) Wang, Q.; Jing, X.; Han, J.; Yu, L.; Xu, Q. Mater. Lett. 2018, 215, 65.
(e) Liu, Y.; Tang, D.; Cao, K.; Yu, L.; Han, J.; Xu, Q. J. Catal. 2018, 360, 250.
[13] For an example of the molar ratios of silicon to titanium affecting the selectivity of oxidation of aromatic compounds, see:Mukherjee, P.; Bhaumik, A.; Kumar, R. Ind. Eng. Chem. Res. 2007, 46, 8657.
[14] Barbera, D.; Cavani, F.; D'Alessandro, T.; Fornasari, G.; Guidetti, S.; Aloise, A.; Giordano, G.; Piumetti, M.; Bonelli, B.; Zanzottera, C. J. Catal. 2010, 275, 158.
[15] Zuo, Y.; Wang, X.; Guo, X. Ind. Eng. Chem. Res. 2011, 50, 8485.
[16] Ahmed, M. H. M.; Muraza, O.; Jamil, A. K.; Shafei, E. N.; Yamani, Z. H.; Choi, K. H. Energy Fuels 2017, 31, 5482.
[17] Voutyritsa, E.; Theodorou, A.; Kokotou, M. G.; Kokotos, C. G. Green Chem. 2017, 19, 1291.
[18] Chen, Y. F.; Chen, J.; Lin, L. J.; Chuang, G. J. J. Org. Chem. 2017, 82, 11626.
[19] Long, Z.; Wang, Z.; Zhou, D.; Wan, D.; You, J. Org. Lett. 2017, 19.
[20] Stowell, J. C.; Lau, C. M. J. Org. Chem. 2002, 51, 1614.

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