English
往期目录
新闻公告
More
化学进展 2009, Vol. 21 Issue (12): 2635-2641 前一篇   后一篇

• 综述与评论 •

钝化芳环的硝化研究进展*

刘金强; 钱超; 陈新志**   

  1. (浙江大学化工所 杭州 310027)
  • 收稿日期:2008-12-19 修回日期:2009-01-01 出版日期:2009-12-24 发布日期:2009-12-01
  • 通讯作者: 陈新志 E-mail:xzchen@zju.edu.cn
  • 基金资助:

    20776127;国家科技支撑计划课题资助项目（2007BAI34B07）;国家自然科学基金

下载PDF ( 2884 ) 引用
导出

Nitration of Deactivated Aromatic Compounds

Liu Jinqiang; Qian Chao; Chen Xinzhi**   

  1. (Institute of  Chemical Engineeing, Zhejiang University, Hangzhou 310027, China)
  • Received:2008-12-19 Revised:2009-01-01 Online:2009-12-24 Published:2009-12-01
  • Contact: Chen Xinzhi E-mail:xzchen@zju.edu.cn

芳香族化合物的硝化反应是工业生产中重要的单元反应，钝化芳环的硝化反应在医药、农药、染料和炸药合成中有重要地位。本文从硝化试剂角度综述了近年来钝化芳环的硝化反应的进展，包括硝酸盐/硫酸、硝酸酯、硝酸、氮氧化物等硝化方法。简要评述了这些方法的特点，并展望了硝化方法的研究方向。其中，硝酸盐/硫酸体系具有较强的硝化能力，对于钝化芳环，可以在温和条件下以高收率得到硝化产物，在实验室制备或工业应用中具有较高的应用价值；其他硝化方法由于各种原因暂时不能对钝化程度较高的芳环进行硝化，还需进一步研究具有较高活性的硝化体系。

关键词： 硝化, 钝化芳环, 硝酸盐, 硝酸酯, 硝酸, 氮氧化物

The nitration of aromatics is an important reaction in chemical industry, and the nitration of deactivated aromatics plays a key role in the synthesis of medicines, pesticides, dyes and explosives. In this paper, the latest progress of the nitration of deactivated aromatic compounds is reviewed in the point of view of nitrating agents, including nitrate-sulfuric acid, nitrate ester, nitric acid and nitrogen oxides. Their specific features, merits and demerits are outlined and the perspectives of the nitration are prospected. Among them, nitrate-sulfuric acid system with higher nitrating activity can get high yields at mild condition in the nitration of deactivated aromatic compounds and could be used in the laboratory and industrial applications. And for other nitrating methods, the nitration of high degree deactivated aromatics is, so far, not satisfying for different reasons and more efforts are needed for developing new agents with higher nitrating activity.

 Contents
1 Introduction
2 Nitrate/sulfuric acid as nitration agent
2.1 Nitrate/sulfuric acid as nitration agent
2.2 Supported nitrate as nitration agent
3 Nitrate ester as nitration agent
3.1 Ethylene glycol dinitrate as nitration agent
3.2 Trifluoroacetyl nitrate as nitration agent
3.3 Nitration with acetyl nitrate catalyzed by ionic liquid
4 Nitric acid as nitration agent
4.1 Catalyzed by solid acid
4.2 Catalyzed by BrÖnsted acid ionic liquid
4.3 Catalyzed by Ln perfluorooctanesulfonate and perfluorooctanesulfonic acid
4.4 Catalyzed by Lewis acid
5 Nitrogen oxides as nitration agent
5.1 NO2/O2 as nitration agent
5.2 N2O5 as nitration agent
5.3 NO2/O3 as nitration agent
5.4 N2O4 as nitration agent
6 Conclusion

Key words: nitration, deactivated aromatic compounds, nitrates, nitrate esters, nitric acid, nitrogen oxides

中图分类号: 

()

[ 1 ] 　Rahaman M, Mandal B P , Ghosh P. AICHE J , 2007 , 53 ( 9) : 2476 —2480
[ 2 ] 　Moodie R B , Payne M A , Schofield K. J . Chem. Soc. Perkin Trans. 2 , 1985 , (9) : 1457 —1464
[ 3 ] 　Majumdar M P , Kudav N A. Indian J . Chem. Sec. B2Org. Chem. Inc. Med. Chem. , 1976 , 14 (12) : 1012 —1013
[ 4 ] 　Sura T P , Ramana M, Kudav N A. Synth. Commun. , 1988 , 18 (16P17) : 2161 —2165
[ 5 ] 　Mundla S R. Tetrahedron Lett . , 2000 , 41 (22) : 4277 —4279
[ 6 ] 　Almog J , Klein A , Sokol A , et al . Tetrahedron Lett . , 2006 , 47 (49) : 8651 —8652
[ 7 ] 　Ramana M, Malik S S , Parihar J A. Tetrahedron Lett . , 2004 , 45 (47) : 8681 —8683
[ 8 ] 　Oxley J C , Smith J L , Moran J S , et al . Tetrahedron Lett . , 2008 , 49 (28) : 4449 —4451
[ 9 ] 　Hajipour A R , Zarei A , Khazdooz L , et al . Synth. Commun. , 2005 , 35 (17) : 2237 —2241
[10 ] 　Yadav J S , Meshram H M. Pure & Appl . Chem. , 2001 , 73 (1) : 199 —203
[11 ] 　Meshram H M, Ganesh Y, Madhavi A V , et al . Synth. Commun. , 2003 , 33 (14) : 2497 —2503
[12 ] 　Zolfigol M A , Mirjalili B F , Bamoniri A , et al . Bull . Kor. Chem. Soc. , 2004 , 25 (9) : 1414 —1416
[13 ] 　Shokrolahi A , Zali A , Keshavarz M H. Chin. Chem. Lett . , 2007 , 18 (9) : 1064 —1066
[14 ] 　Botvay A , Mathe A , Poppl L. Polymer , 1999 , 40 (17) : 4965 — 4970
[15 ] 　Smith K, Gibbins T, Millar R W, et al . J . Chem. Soc. Perkin Trans. 1 , 2000 , (16) : 2753 —2758
[16 ] 　吕春绪(Lv C X) , 彭新华( Peng X H) . 火炸药学报(Chinese Journal of Explosives & Propellants) , 2001 , (01) : 11 —12
[17 ] 　Smith K, Liu S F , El2Hiti GA. Ind. & Eng. Chem. Res. , 2005 , 44 (23) : 8611 —8615
[18 ] 　Dal E , Lancaster N L. Org. & Biomol . Chem. , 2005 , 3 ( 4) : 682 —686
[19 ] 　Wang S , Sun Z, Nie J . Chin. J . Chem. , 2008 , 26 (12) : 2256 — 2260
[20 ] 　Bharadwaj S K, Hussain S , Kar M, et al . Appl . Catal . A2Gen. , 2008 , 343 (1P2) : 62 —67
[21 ] 　Hajipour A R , Ruoho A E. Tetrahedron Lett . , 2005 , 46 ( 48) : 8307 —8310
[22 ] 　Olah G A , Orlinkov A , Oxyzoglou A B , et al . J . Org. Chem. , 1995 , 60 (22) : 7348 —7350
[23 ] 　Olah GA , Orlinkov A V , Ramaiah P , et al . Russ. Chem. Bull . , 1998 , 47 (5) : 924 —927
[24 ] 　Qiao K, Yokoyama C. Chem. Lett . , 2004 , 33 (7) : 808 —809
[25 ] 　Fang D , Shi Q R , Cheng J , et al . Appl . Catal . A2Gen. , 2008 , 345 (2) : 158 —163
[26 ] 　岳彩波(Yue C B) , 魏运洋(Wei Y Y) , 吕敏杰(Lv MJ ) . 含能材料(Chinese Journal of Energetic Materials) , 2007 , 15 (2) : 118 — 121 , 127
[27 ] 　Yi WB , Cai C. Synth. Commun. , 2006 , 36 (20) : 2957 —2961
[28 ] 　Yi WB , Cai C. J . Energetic Materials , 2007 , 25 (2) : 129 —139
[29 ] 　方东(Fang D) , 施群荣(Shi Q R) , 巩凯(Gong K) 等. 含能材料 (Chinese Journal of Energetic Materials) , 2008 , 16 (1) : 103 —112
[30 ] 　Frost C G, Hartley J P , Griffin D. Tetrahedron Lett . , 2002 , 43 (27) : 4789 —4791
[31 ] 　Peng X H , Suzuki H , Lu C X. Tetrahedron Lett . , 2001 , 42 (26) : 4357 —4359
[32 ] 　Peng X H , Suzuki H. Org. Lett . , 2001 , 3 (22) : 3431 —3434
[33 ] 　Peng X H , Fukui N , Mizuta M, et al . Org. & Biomol . Chem. , 2003 , 1 (13) : 2326 —2335
[34 ] 　Cho J K, Kim YT, Kim Y G, et al . Res. Chem. Intermed. , 2006 , 32 (8) : 759 —766
[35 ] 　Bakke J M, Hegbom I. Acta Chimica Scandinavica , 1994 , 48 (2) : 181 —182
[36 ] 　Bakke J M, Ranes E. J . Chem. Soc.2Perkin Trans. 2 , 1997 , (10) : 1919 —1923
[37 ] 　蔡春(Cai C) , 吕春绪(Lv C X) . 火炸药学报(Chinese Journal of Explosives & Propellants) , 2000 , (1) : 25 —27
[38 ] 　Bak R R , Smallridge A J . Tetrahedron Lett . , 2001 , 42 ( 38) : 6767 —6769
[39 ] 　Hill A J , Millar R W, Sandall J . Org. Biomol . Chem. , 2004 , 2 (1) : 90 —92
[40 ] 　Suzuki H , Kozai I , Murashima T. J . Chem. Res. (S) , 1993 , (4) : 156 —157
[41 ] 　Suzuki H , Iwaya M, Mori T. Tetrahedron Lett . , 1997 , 38 (32) : 5647 —5650
[42 ] 　Zolfigol M A , Ghaemi E , Madrakian E. Synlett , 2003 , (2) : 191 — 194
[43 ] 　Iranpoor N , Firouzabadi H , Heydari R , et al . Synth. Commun. , 2005 , 35 (2) : 263 —270
[1] 李帅, 朱娜, 程扬健, 陈缔. NH3选择性催化还原NOx的铜基小孔分子筛耐硫性能及再生研究[J]. 化学进展, 2023, 35(5): 771-779.
[2] 贾斌, 刘晓磊, 刘志明. 贵金属催化剂上氢气选择性催化还原NOx[J]. 化学进展, 2022, 34(8): 1678-1687.
[3] 王晓晗, 刘彩霞, 宋春风, 马德刚, 李振国, 刘庆岭. 金属有机骨架材料在氨低温催化还原氮氧化物反应中的应用[J]. 化学进展, 2020, 32(12): 1917-1929.
[4] 王海潮, 唐明金, 谭照峰, 彭超, 陆克定. 硝酰氯的大气化学[J]. 化学进展, 2020, 32(10): 1535-1546.
[5] 顾芳婷, 胡敏*, 郑竞, 郭松. 大气颗粒物中有机硝酸酯的研究进展[J]. 化学进展, 2017, 29(9): 962-969.
[6] 李盼盼, 于锋, 朱明远, 汤常金, 代斌, 董林. 选择性氧化还原脱硝催化剂[J]. 化学进展, 2016, 28(10): 1578-1590.
[7] 吴德礼*, 傅旻瑜, 马鲁铭. 生物及化学反硝化过程中N2O的产生与控制[J]. 化学进展, 2012, (10): 2054-2061.
[8] 孙亮 许悠佳 曹青青 胡冰清 王超 荆国华. 氧化锰基催化剂低温NH3选择性还原NOx反应及其机理*[J]. 化学进展, 2010, 22(10): 1882-1900.
[9] 郭丽红,刘咏,孟明. 稀燃NOx储存－还原催化剂*[J]. 化学进展, 2009, 21(05): 964-970.
[10] 马涛,王睿. NOx的催化分解研究*[J]. 化学进展, 2008, 20(06): 798-810.
[11] 王云海,罗云敬,钟儒刚. 过氧亚硝酸根对蛋白质损伤的研究进展*[J]. 化学进展, 2007, 19(06): 893-901.
[12] 高平章,卢乃浩,高中洪. 蛋白质酪氨酸硝化检测方法*[J]. 化学进展, 2007, 19(04): 590-597.
[13] 池泉,黄开勋. 蛋白质酪氨酸硝化的研究*[J]. 化学进展, 2006, 18(0708): 1019-1025.
[14] 刘晓智 陆世维 . 硒催化CO/H2O还原芳烃硝化物制苯胺及其衍生物的反应[J]. 化学进展, 2006, 18(05): 550-555.
[15] 李海玲 徐辉碧 高中洪 . 微量元素铁与蛋白质酪氨酸硝化[J]. 化学进展, 2006, 18(05): 622-626.
阅读次数
全文


摘要

钝化芳环的硝化研究进展*