A green and efficient trinitration system for aromatic compounds with Bi(NO₃)₃·5H₂O/[HMIM]ClO₄ as catalyst in HNO₃/Ac₂O

Abstract

To investigate the green trinitration method of aromatic compounds, with Lewis acid/ionic liquid as catalyst and HNO₃/Ac₂O as nitration reagent, a Lewis acid/ionic liquid/HNO₃/Ac₂O system was established. In various combinations of Lewis acids and ionic liquids, Bi(NO₃)₃·5H₂O/[HMIM]ClO₄ proved to be a very efficient catalyst for the trinitration of activated aromatic compounds and reusable for 3 times. Reaction conditions for the trinitration were optimized and yields of the trinitro products were from mild to excellent. This sulfuric acid-free system has the advantages of strong trinitration ability, low environment pollution, low toxicity, low cost and high potential for industrial application.

Keywords

Green trinitration / Aromatic compound / Lewis acid / Ionic liquid / Acetyl nitrate

References

[1] Frank H. G., Stadelhofer J. W. Industrial Aromatic Chemistry, 1988

[2] Brei V. V., Prudius S. V., Melezhyk O. V. Appl. Catal. A, Gen., 2003, 239(1/2): 11.

[3] Peng F., Honghai X., Tang X., Kang C., Li L., Li Z. Chem. Res. Chinese Universities, 2012, 28(1): 47.

[4] Millar R. W., Arber A. W., Endsor R. M., Hamid J., Colclough M. E. J. Energ. Mater., 2011, 29(2): 88.

[5] Iranpoor N., Firouzabadi H., Heydari R., Shiri M. Synth. Commun., 2005, 35(2): 263.

[6] Crampton M. R., Cropper E. L., Gibbons L. M., Millar R. W. Green Chem., 2002, 4(3): 275.

[7] Yi W. B., Cai C. J. Energ. Mater., 2007, 25(2): 129.

[8] Sreedhar I., Singh M., Raghavan K. V. Catal. Sci. Technol., 2013, 3(10): 2499.

[9] Lancaster N. L., Llopis-Mestre V. Chem. Commun., 2003, 22: 2812.

[10] Wang P. C., Yao K., Zhu J., Liu X., Lu T. T., Lu M. Catal. Commun., 2013, 39: 90.

[11] Kuba M. G., Prins R., Pirngruber G. D. Appl. Catal. A, Gen., 2007, 333(1): 24.

[12] Tang B., Wei S. B., Peng X. H. Synth. Commun., 2014, 44(14): 2057.

[13] Waller F. J., Barrett A. G. M., Braddock D. C., Ramprasad D. Chem. Commun., 1997, 6613.

[14] Sun H. B., Hua R. M., Yin Y. W. J. Org. Chem., 2005, 70(22): 9071.

[15] Ravi P., Tewari S. P. Catal. Commun., 2012, 19: 37.

[16] Chowdhury S., Mohan R. S., Scott J. L. Tetrahedron, 2007, 63(11): 2363.

[17] Smith K., Liu S., El-Hiti G. A. Ind. Eng. Chem. Res., 2005, 44(23): 8611.

[18] Wang P. C., Lu M., Zhu J., Song Y. M., Xiong X. F. Catal. Commun., 2011, 14(1): 42.

[19] Aridoss G., Laali K. K. J. Org. Chem., 2011, 76(19): 8088.

[20] Jacoway J., Kumar G. G. K. S. N., Laali K. K. Tetrahedron Lett., 2012, 53(50): 6782.

[21] Dal E., Lancaster N. L. Org. Biomol. Chem., 2005, 3(4): 682.

[22] Song C. E., Shim W. H., Roh E. J., Choi J. H. Chem. Commun., 2000, 1695.

[23] Yadav J. S., Reddy B. V. S., Gayathri K. U., Prasad A. R. Synthesis, 2002, 2002(17): 2537.

[24] Wang S. J., Sun Z. Y., Nie J. Chin. J. Chem., 2008, 26(12): 2256.

[25] Braddock C. Green Chem., 2001, 3(2): 26.

[26] Waller F. J., Barrett A. G. M., Braddock D. C., McKinnell R. M., Ramprasad D. J. Chem. Soc., Perkin Trans., 1999, 1(8): 867.

[27] Briand G. G., Burford N. Chem. Rev., 1999, 99(9): 2601.

[28] Arduengo A. J., Dias H. V. R., Harlow R. L., Kline M. J. Am. Chem. Soc., 1992, 114(14): 5530.

[29] Earle M. J., Katdare S. P., Seddon K. R. Org. Lett., 2004, 6(5): 707.

[30] Straessler N. A. Synth. Commun., 2010, 40(17): 2513.