A Green and Efficient Trinitration System for Aromatic Compounds with Bi(NO3)3·5H2O/[HMIM]ClO4 as Catalyst in HNO3/Ac2O

doi:10.1007/s40242-015-5087-1

高等学校化学研究 ›› 2015, Vol. 31 ›› Issue (5): 761-765.doi: 10.1007/s40242-015-5087-1

A Green and Efficient Trinitration System for Aromatic Compounds with Bi(NO₃)₃·5H₂O/[HMIM]ClO₄ as Catalyst in HNO₃/Ac₂O

SUN Weizhi¹, YU Shitao², XIAN Mo¹

1. CAS Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, P. R. China;
2. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. China

收稿日期:2015-03-11 修回日期:2015-05-12 出版日期:2015-10-01 发布日期:2015-06-29
通讯作者: XIAN Mo, E-mail: xianmo@qibebt.ac.cn E-mail:xianmo@qibebt.ac.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.21376255).

A Green and Efficient Trinitration System for Aromatic Compounds with Bi(NO₃)₃·5H₂O/[HMIM]ClO₄ as Catalyst in HNO₃/Ac₂O

SUN Weizhi¹, YU Shitao², XIAN Mo¹

1. CAS Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, P. R. China;
2. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. China

Received:2015-03-11 Revised:2015-05-12 Online:2015-10-01 Published:2015-06-29
Contact: XIAN Mo, E-mail: xianmo@qibebt.ac.cn E-mail:xianmo@qibebt.ac.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21376255).

摘要/Abstract

摘要：

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.

关键词: Green trinitration, Aromatic compound, Lewis acid, Ionic liquid, Acetyl nitrate

Abstract:

Key words: Green trinitration, Aromatic compound, Lewis acid, Ionic liquid, Acetyl nitrate

SUN Weizhi, YU Shitao, XIAN Mo. A Green and Efficient Trinitration System for Aromatic Compounds with Bi(NO₃)₃·5H₂O/[HMIM]ClO₄ as Catalyst in HNO₃/Ac₂O[J]. 高等学校化学研究, 2015, 31(5): 761-765.

SUN Weizhi, YU Shitao, XIAN Mo. A Green and Efficient Trinitration System for Aromatic Compounds with Bi(NO₃)₃·5H₂O/[HMIM]ClO₄ as Catalyst in HNO₃/Ac₂O[J]. Chemical Research in Chinese Universities, 2015, 31(5): 761-765.

参考文献

[1] Frank H. G., Stadelhofer J. W., Industrial Aromatic Chemistry, Springer, Verlag, 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, (17), 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), G26
[26] Waller F. J., Barrett A. G. M., Braddock D. C., McKinnell R. M., Ramprasad D., J. Chem. Soc., Perkin Trans. 1, 1999, (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

A Green and Efficient Trinitration System for Aromatic Compounds with Bi(NO₃)₃·5H₂O/[HMIM]ClO₄ as Catalyst in HNO₃/Ac₂O

A Green and Efficient Trinitration System for Aromatic Compounds with Bi(NO₃)₃·5H₂O/[HMIM]ClO₄ as Catalyst in HNO₃/Ac₂O

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	LUO Li, WANG Sen, WU Zhiwei, QIN Zhangfeng, DONG Mei, WANG Jianguo, FAN Weibin. Influence of the ZSM-5 Support Acidity on the Catalytic Performance of Pd/ZSM-5 in Lean Methane Oxidation[J]. 高等学校化学研究, 2022, 38(1): 229-236.
[2]	YU Fengli, CHI Yujie, GAO Chong, CHEN Ruirui, XIE Congxia, YU Shitao. Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids[J]. 高等学校化学研究, 2020, 36(5): 865-869.
[3]	ZHAO Qi, LIANG Xiaoxiao, YOU Yingxue, WANG Yuliang, DU Xinwei, LIU Baijun, HU Wei. Proton Conductivity Improvement Effect of Cellulose on SPEEKK Based PEM[J]. 高等学校化学研究, 2019, 35(5): 916-923.
[4]	GUAN Lianyue, LUO Qiang, LIANG Na, YU Wei. Determination of Lignans in Schisandra sphenanthera and Schisandra chinensis Using Ionic Liquid-based Ultrasonic-assisted Extraction and High-performance Liquid Chromatography[J]. 高等学校化学研究, 2018, 34(6): 887-892.
[5]	CHEN Siyan, GAO Zhenhai. Structure of a Mixture of Graphene Plates and Ionic Liquid 1-Octyl-3-methylimidazolium Hexafluoroborate[J]. 高等学校化学研究, 2018, 34(4): 598-603.
[6]	ZHANG Liangliang, XIN Xuelian, LU Yukun, SUN Daofeng. High-selectivity Detection of 2,4,6-Trinitrophenol Based on Fluorescent Mg-MOF-74 in Ethanol Solution[J]. 高等学校化学研究, 2018, 34(2): 175-179.
[7]	XU Chao, YIN Xuhan, ZHANG Chuan, CHEN Hongyue, HUANG He, HU Yi. Improving Catalytic Performance of Burkholderiacepacia Lipase by Chemical Modification with Functional Ionic Liquids[J]. 高等学校化学研究, 2018, 34(2): 279-284.
[8]	LI Hengjie, GAO Pengfei, XUE Xiaolu, ZHANG Hongxi, ZHAO Yongxiang. Fluorine Modified TAPO-5: Synthesis and Catalytic Performance in Cyclohexanone Ammoximation[J]. 高等学校化学研究, 2018, 34(2): 247-253.
[9]	WANG Jingyang, ZHANG Meng, XU Xiaodong, FENG Jing, WANG Yanli, ZHANG Milin, HAN Wei, CHEN Yitung, TIAN Guoxin. Synthesis and Characterization of [Cu(N-MeIm)₄(BF₄)₂] in Ionic Liquid[J]. 高等学校化学研究, 2018, 34(1): 8-12.
[10]	Ana Maria POPESCU, Kazimir YANUSHKEVICH, Vasile SOARE, Cristina DONATH, Elena Ionela NEACSU, Virgil CONSTANTIN. Recovery of Metals from Anodic Dissolution Slime of Waste from Electric and Electronic Equipment(WEEE) by Extraction in Ionic Liquids[J]. 高等学校化学研究, 2018, 34(1): 113-118.
[11]	LI Shuang, LI Shuni, ZHAI Quanguo, JIANG Yucheng, HU Mancheng. Phase Behavior of Ionic Liquids-Cesium Carbonate-Water Aqueous Two-phase Systems and Their Extraction of L-Tryptophan[J]. 高等学校化学研究, 2018, 34(1): 127-131.
[12]	BU Luxia, LIU Daying, WEI Zhen, MA Zhanlin. Physicochemical Properties of Bi-containing Ionic Liquid Analogs Based on Choline Chloride[J]. 高等学校化学研究, 2017, 33(6): 929-933.
[13]	TONG Jing, ZHENG Xu, TONG Jian, QU Ye, LIU Lu, LI Hui. Molar Surface Gibbs Energy of the Aqueous Solution of Ionic Liquid[C₄mim] [OAc][J]. 高等学校化学研究, 2017, 33(5): 828-832.
[14]	ZHANG Lifeng, DU Suqing, SONG Qiaolan, LIU Yi, GUO Shouwu. Fluorine-free Ionic Liquid Based on Thiocyanate Anion with Propylene Carbonate as Electrolytes for Supercapacitors:Effects of Concentration and Temperature[J]. 高等学校化学研究, 2017, 33(5): 779-784.
[15]	BIAN Min, TIAN Ling, YAO Cheng. An Improved Method of Simultaneous Determination of Four Bioactive Compounds in Evodiae Fructus Using Ionic Liquids as Mobile Phase Additives in High Performance Liquid Chromatography[J]. 高等学校化学研究, 2017, 33(4): 552-558.