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Progress in Chemistry 2009, Vol. 21 Issue (12): 2635-2641 Previous Articles   Next Articles

• Review •

Nitration of Deactivated Aromatic Compounds

Liu Jinqiang; Qian Chao; Chen Xinzhi**   

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

CLC Number: 

[ 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
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