|Table of Contents|

Synthesis of 2,3,5,6-Tetraamineopyridine Hydrochloride

《南京理工大学学报》(自然科学版)[ISSN:1005-9830/CN:32-1397/N]

Issue:
2012年05期
Page:
898-
Research Field:
Publishing date:

Info

Title:
Synthesis of 2,3,5,6-Tetraamineopyridine Hydrochloride
Author(s):
WANG Peng-cheng1LIU Xiang1LU Ming1XIONG Xian-feng2
1. School of Chemical Engineering,NUST,Nanjing 210094,China;2. Xi爷an Modern Chemistry Research Institute,Xi′an 710065,China
Keywords:
nitropyridinesaminopyridinesnitrificationcatalytic hydrogenation
PACS:
TJ55;O6
DOI:
-
Abstract:
In order to study the synthetic technology of 2, 3, 5, 6-tetraaminopyridine, 2, 6-diaminopyridine is nitrated into 2,6-diamino-3,5-dinitropyridine which is reduced into 2,3,5,6-tet-raaminopyridine. The super-acid system is much better than the mixed acid. Under 30益temperatureand 3 h reaction time,the yield increases to 90%. The experiment results show that the Raney Nicatalytic hydrogenation is better reduction method than the hydrazine hydrate and Fe powder. Whenthe reaction solvent is ethanol,the reaction temperature is 50℃,the reaction pressure is 1. 0 ~1. 5MPa,and the amount of catalyst is 10%(mass percent in nitropyridine compounds),the yield of 2,3,5,6-tetraaminopyridine hydrochloric acid is 89%. The Raney Ni can be recycled for four timesafter treated with of sodium hydroxide solution.

References:

[1]Richard A,Hollins L H. Aminonitropyridines and theirN-Oxides[J]. J Heterocyclic Chem,1996,33:895-904.
[2] 王艳红,宋元军,黄玉东,等. 一个简易的2,6-二氨基-3,5-二硝基吡啶-1-氧化物的合成方法[J]. 有机化学,2009,29(5):780-783.Wang Yanhong,Song Yuanjun,Huang Yudong,et al. Asimple method for preparing 2, 6-diamino-3, 5-dinitropyridine-1-oxide[J]. Chin J Org Chem,2009,29(5):780-783.
[3] 黄玉东,王艳红,王保启,等. 一种制备2,3,5,6-四氨基吡啶盐酸盐的方法[ P]. CN:200810064682,2008-10-22.
[4] Doetze J. Design, synthesis and properties of a novelrigid rod polymer,“PIPD冶or“ M5冶:high modulus andtenacity fibres with substantial compressive strength[J]. Polymer,1998,39(24):5981-5986.
[5] 李金山,黄奕刚,董海山. 多硝基吡啶的密度泛函理论研究[J]. 含能材料,2003,11(4):177-181.Li Jinshan, Huang Yigang, Dong Haishan. Densityfunctional theory study on polynitropyridine[J]. Chin JEnergetic Mater,2003,11(4):177-181.
[6] 李金山,黄奕刚,董海山. 多硝基吡啶及其氮氧化物性能的理论预测[J]. 含能材料,2004,12( A2):576-579.Li Jinshan,Huang Yigang,Dong Haishan. Theory studyon polynitropyridine and its nitrogen oxides[J]. Chin JEnergetic Mater,2004,12(A2):576-579.
[7] Ritter H,Licht H H. Synthesis and reactions of dinitratedamino and diaminopyridines [ J]. J Heterocycl Chem,1995,32:585-590.
[8] Hollins R A,Merwin L M,Nissan R A,et al. Aminoni-tropyridines and their N-oxides[J]. J Heteocycl Chem,1996,33:895-904.
[9] Ritter H,Licht H H. 2,4,6-trinitropyridine and relatedcompounds, synthesis and characterization [ J ].Propellants Explosives Pyrotechnics,1988,13:25-29.
[10] 成健,姚其正,刘祖亮. 2,6-二氨基-3,5-二硝基吡啶-1-氧化物的合成新方法[J]. 有机化学. 2008,28(11):1943-1947.Cheng Jian,Yao Qizheng,Liu Zuliang. Novel synthesisof 2,6-diamino-3,5-dinitropyridine-1-oxide[J]. Chin JOrg Chem,2008,28:1943-1947.
[11] Williams R L, Cohen S A. The chemistry of arylte-traamines域. The synthesis of 2,3,5,6-tetraamineopyridine[J]. J Heterocyclic Chem,1971,8:841-843.
[12] 安国成,詹家荣. 2,3,5,6-四氨基吡啶的制备方法[P]. CN:200610030027,2006-12-27.
[13] 成健,姚其正,刘祖亮. 2,6-二氨基-3,5-二硝基吡啶-1-氧化物的合成新方法[J]. 含能材料,2009,17 (2):167-168.Cheng Jian,Yao Qizheng,Liu,Zuliang. Synthesis of 2,6-diamino-3, 5-dinitropyridine-1-oxide [ J ]. Chin JEnergetic Mater,2009,17(2):167-168.
[14] 成健,刘祖亮,姚其正,等. 2,6-二氨基(4-氨基)吡啶的二硝化反应[J]. 火炸药学报,2009,32(3):9-11.Cheng Jian,Liu,Zuliang,Yao Qizheng,et al. Dinitrationof 2, 6-diamino ( 4-amino ) pyridines [ J ]. Chin JExplosives and Propellants,2009,32(3):9-11.
[15] Leslie W,Deady M. Studies on the mechanism of thenitraminopyridine rearrangement [ J ]. Tetrahedron,1979,35:2895-2900.
[16] 蔡可迎,魏贤勇. 水中氢氧化氧铁催化水合肼还原芳香族硝基化合物[J]. 河北师范大学学报(自然科学版),2007,31(5):633-634.Cai Keying,Wei Xianyong. Reduction of aromatic nitrocompounds with hydrazine hydrate catalyzed by ironoxide hydroxide in water[J]. J Hebei Normal University(Natural Science Edition),2007,31(5):633-634.
[17] 徐善利,陈宏博,李树德. 催化加氢还原芳香硝基化合物制备芳胺的技术进展[ J]. 精细石油化工,2006,23(4):58-60.Xu Shanli, Chen Hongbo, Li Shude. Progress inpreparation of aromatic amine from aromatic nitrocompounds by catalytic hydrogenation [ J]. SpecialityPetrochemicals,2006,23(4):58-60.

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Last Update: 2012-11-26