研究简报

苯胺基于钛硅分子筛的选择性氧化合成氧化偶氮苯

  • 宋玉婉 ,
  • 冯韶静 ,
  • 韩维 ,
  • 肖亚平
展开
  • 南京师范大学化学与材料科学学院 南京 210023

收稿日期: 2018-08-28

  修回日期: 2018-11-13

  网络出版日期: 2018-11-30

基金资助

国家自然科学基金(Nos.21776139,21302099)、江苏省自然科学基金(No.BK20161553)、江苏省高效自然科学基金(No.16KJB150019)资助项目.

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

  • Song Yuwan ,
  • Feng Shaojing ,
  • Han Wei ,
  • Xiao Yaping
Expand
  • 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).

摘要

报道了一种通过调节TS-1的硅钛摩尔比来提高苯胺高效、高选择性转化为相应氧化偶氮苯的方法.在TS-1的硅钛摩尔比为80时,以H2O2为氧化剂,芳基苯胺以良好的产率以及高选择性转化为相应的氧化偶氮苯类化合物.还研究了H2O2摩尔比、溶剂、催化剂回收率等反应参数对反应的影响.

关键词: 苯胺; 氧化; 氧化偶氮苯; H2O2

本文引用格式

宋玉婉 , 冯韶静 , 韩维 , 肖亚平 . 苯胺基于钛硅分子筛的选择性氧化合成氧化偶氮苯[J]. 有机化学, 2019 , 39(4) : 1181 -1186 . DOI: 10.6023/cjoc201808032

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.

参考文献

[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.

文章导航

/

〈 〉