摘要含硝胺（—NHNO2）基氮杂环类化合物具有高密度、高能量、高稳定性等优点，其 密度、生成热、爆压和爆度、以及冲击波等性能都令人满意，它们的性能甚至可以超 越 RDX 和 HMX。为新型炸药及含能材料的研究指引了一个新的方向。68427

二硝基甘胍及其衍生物则是氮杂环类化合物中各项性能都很突出的代表，本课题 主要探究二硝基甘胍衍生物的最佳合成路线。主要合成思路是：首先通过二硝基甘胍 与乙酸酐在加热条件下发生取代反应，得到双乙酰基二硝基甘胍；最后在硝化体系中 硝化得到最终产品二硝基甘胍衍生物。优化了反应条件并通过 IR、HNMR 和 MS 对所有 反应产物进行表征。

毕业论文关键词: 高能量密度材料 ;二硝基甘胍衍生物 ; N-酰化反应 ;硝化反应

Title Synthesis of Octahydro-2,5-bis(nitroimino)imidazo[4,5-d]   imidazole derivatives

Abstract

Nitrogen heterocyclic compounds have the advantages of high density, high energy, high stability, etc. The performances of density, the heat of formation, detonation pressure and critical degree, and shock wave are satisfying and, even many of them may be superior to that of RDX and HMX. The studies of them can direct us a new way of the discovery of new explosives and energy materials.

Octahydro-2,5-bis(nitroimino)imidazo[4,5-d]imidazole and its derivatives are excellent nitrogen-rich heterocyclic compounds. The main synthetic route is as follows: octahydro-2,5-bis(nitroimino)imidazo[4,5-d]imidazole firstly reacts with (AcO)2O to get bis-acetyl substituted octahydro-2,5-bis(nitroimino)imidazo[4,5-d]imidazole; and then nitrification occurred to obtain the target compound. The reaction conditions such as reaction time, reaction temperature and the mole ratio of the reagents were optimized and all the compounds were characterized by IR, NMR and MS.

Key words high energy density materials ;octahydro-2,5-bis(nitroimino)imidazo[4,5-d]imidazole derivatives; N-acylating reaction; nitration reaction

目 次

1. 绪论 1

1.1 研究背景 1

1.2 氮杂环类含能材料 4

1.3  二硝基甘胍衍生物 7

1.4 本课题研究的目的和意义 8

1.5 本课题研究的内容 8

2. 合成路线设计 8

2.1  二硝基甘胍的合成 8

2.2  双乙酰基二硝基甘胍的合成以及硝化路线 9

2.3  硝基胍为原料合成双乙酰基二硝基甘胍 10

3. 实验部分 11

3.1 实验仪器和药品 11

3.2 实验步骤及结果讨论 11

3.2.1  双乙酰基二硝基甘胍的合成 11

3.2.2  双乙酰基二硝基甘胍的硝化 14