FOX-7的合成和反应机理研究

化学学报 ›› 2004, Vol. 62 ›› Issue (3): 295-301. 上一篇下一篇

研究论文

FOX-7的合成和反应机理研究

蔡华强, 舒远杰, 郁卫飞, 李金山, 程碧波

中国工程物理研究院化工材料研究所, 绵阳, 621900

投稿日期:2003-07-03 修回日期:2003-09-05 发布日期:2014-01-26
通讯作者: 蔡华强,E-mail:danluxiusan@hotmail.com E-mail:danluxiusan@hotmail.com
基金资助:
中国工程物理研究院基金(No.20020540)资助课题.

Study on Synthesis of FOX-7 and Its Reaction Mechanism

CAI Hua-Qiang, SHU Yuan-Jie, YU Wei-Fei, LI Jin-Shan, CHENG Bi-Bo

Institute of Chemical Materials, China Academy of Engineering Physics, Mianyang 621900

Received:2003-07-03 Revised:2003-09-05 Published:2014-01-26

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摘要/Abstract

以2-甲基咪唑为原料合成出1,1-二氨基-2,2-二硝基乙烯(FOX-7)并进行了结构表征,从中间体过滤母液中分离出副产物2-甲基-4(5)-硝基咪唑和仲班酸.直接合成的2-甲基-4(5)-硝基咪唑和仲班酸,最佳收率分别为67.3%和63.3%.首次提出了一个较为完整而详细的合成FOX-7的反应机理,硝基重排成亚硝酸酯是反应的关键步骤.FOX-7主要是通过2-甲基咪唑→2-甲基-4(5)-二氢-5-咪唑啉酮→2-(二硝基亚甲基)-5,5-二硝基-4-咪唑烷二酮→2-(二硝基亚甲基)-4,5-咪唑烷二酮→FOX-7步骤形成.论述了各中间体形成的详细过程并进行了证明,应用该机理解释了硝化过程中主产物和副产物的变化规律.

关键词: 1,1-二氨基-2,2-二硝基乙烯(FOX-7), 仲班酸, 2-甲基-4(5)-硝基咪唑, 反应机理

FOX-7 (1,1-diamino-2,2-dinitroethylene) was synthesized by amination of intermediates which were prepared by nitration of 2-methylimidazole and its structure was characterized. 2-Methyl-4(5)-nitroimidazole and parabanic acid were separated from the filtrate of the intermediates. 2-Methyl-4(5)-nitroimidazole and parabanic acid were also synthesized by nitration of 2-methylimidazole under different conditions with the yield being 67.3% and 63.3% respectively. The reaction mechanism of nitration was discussed and proved by theoretical analysis and experimental facts. An important step was rearrangement of nitro group. FOX-7 was formed mainly by the following steps: 2-methylimidazole → 2-methyl-4,5-dihydro-imidazol-5-one→ 2-(dinitromethylene)-5,5-dinitro-4-imidazolidinone→ 2-(dinitromethylene)-4(5)-imidazolidinedione→ FOX-7. The formation of the intermediates was discussed, analyzed and proved. Based on this mechanism the formation and yield of FOX-7 and different intermediates were explained.

Key words: FOX-7, parabanic acid, 2-methyl-4(5)-nitroimidazole, reaction mechanism

引用此文

蔡华强, 舒远杰, 郁卫飞, 李金山, 程碧波. FOX-7的合成和反应机理研究[J]. 化学学报, 2004, 62(3): 295-301.

CAI Hua-Qiang, SHU Yuan-Jie, YU Wei-Fei, LI Jin-Shan, CHENG Bi-Bo. Study on Synthesis of FOX-7 and Its Reaction Mechanism[J]. Acta Chimica Sinica, 2004, 62(3): 295-301.

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FOX-7的合成和反应机理研究

Study on Synthesis of FOX-7 and Its Reaction Mechanism

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