The Unique Synthesis of a Green Metal‐Free Primary Explosive: 3,3′‐azo‐5,5′‐diazido‐1,2,4‐triazole

Lei Cai‐jin; Yang Hong‐wei; Xiong Hua‐lin; Cheng Guang‐bin

摘要

Abstract > The unique synthesis of 3‐azido‐5‐amino‐1,2,4‐triazole ( 1 ) and a possible reaction process were described. The target compound 3,3′‐azo‐5,5′‐diazido‐1,2,4‐triazole ( 2 ) was obtained by further coupling reaction of compound 1 with potassium permanganate. Compound 2 was well characterized by NMR spectra, IR spectroscopy, elemental analysis, differential scanning calorimetry (DSC), and single crystal X‐ray diffraction. The sensitivities towards impact and friction of 2 were characterized by BAM Fallhammer and BAM Friction. Compound 2 exhibited good density (1.68?g?cm ?3 ), good thermal stability (193?°C), high heat of formation (1345.1?kJ?mol ?1 /5.468?kJ?g ?1 ), excellent detonation performance (26.7?GPa, 8345?m?s ?1 ) and acceptable sensitivity (IS=6?J, FS=72?N, EDS=0.224?J). Moreover, compound 2 was tested for its priming ability by detonating RDX. The result indicates that compound 2 could be used as a potential green metal‐free primary explosive. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> > 3-Azido-5-amino-1,2,4-三唑的独特合成（ 1 </ b> 描述了可能的反应过程。目标化合物3,3'-Azo-5,5'- diazido-1,2,4-三唑（ 2 </ b> 通过进一步偶联化合物的反应获得 1 </ b> 用高锰酸钾。化合物 2 </ b> 通过NMR光谱，IR光谱，元素分析，差示扫描量热法（DSC）和单晶X射线衍射的表征很好。对冲击和摩擦的敏感性 2 </ b> 被Bam Fallhammer和Bam摩擦为特征。化合物 2 </ b> 良好的密度（1.68？g？cm ？3 </ sup> ），良好的热稳定性（193°C），形成高的形成热量（1345.1 kJ？摩尔？1 </ sup> / 5.468?KJ？G. ？1 </ sup> ），出色的爆炸性能（26.7？GPA，8345？M？S. ？1 </ sup> ）和可接受的灵敏度（= 6？j，fs = 72？n，eds = 0.224？j）。此外，化合物 2 </ b> 通过爆炸RDx来测试其引发能力。结果表明化合物 2 </ b> 可用作潜在的绿色无金属初级炸药。 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-29946/'>《Propellants, Explosives, Pyrotechnics》</a> <b style="margin: 0 2px;">|</b><span>2020年第3期</span><b style="margin: 0 2px;">|</b><span>共6页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lei Cai‐jin&option=202" target="_blank" rel="nofollow">Lei Cai‐jin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yang Hong‐wei&option=202" target="_blank" rel="nofollow">Yang Hong‐wei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xiong Hua‐lin&option=202" target="_blank" rel="nofollow">Xiong Hua‐lin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Cheng Guang‐bin&option=202" target="_blank" rel="nofollow">Cheng Guang‐bin;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>School of Chemical EngineeringNanjing University of Science and TechnologyXiaolingwei 200 Nanjing Jiangsu P. R. China;</p> <p>School of Chemical EngineeringNanjing University of Science and TechnologyXiaolingwei 200 Nanjing Jiangsu P. R. China;</p> <p>School of Chemical EngineeringNanjing University of Science and TechnologyXiaolingwei 200 Nanjing Jiangsu P. R. China;</p> <p>School of Chemical EngineeringNanjing University of Science and TechnologyXiaolingwei 200 Nanjing Jiangsu P. R. China;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1837.html" title="爆炸物工业、火柴工业">爆炸物工业、火柴工业;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=high-nitrogen compound&option=203" rel="nofollow">high-nitrogen compound;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=azido&option=203" rel="nofollow">azido;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=detonation capacity&option=203" rel="nofollow">detonation capacity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=primary explosive&option=203" rel="nofollow">primary explosive;</a> </p> <div class="translation"> 机译：高氮化合物;Azido;爆炸能力;初级爆炸性; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704024626277.html">The Unique Synthesis of a Green Metal‐Free Primary Explosive: 3,3′‐azo‐5,5′‐diazido‐1,2,4‐triazole</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lei Cai‐jin&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Lei Cai‐jin,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yang Hong‐wei&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Yang Hong‐wei,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xiong Hua‐lin&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Xiong Hua‐lin,</a> <a href="/journal-foreign-29946/" target="_blank" rel="nofollow" class="tuijian_authcolor">Propellants, Explosives, Pyrotechnics .</a> <span>2020</span><span>,第3期</span> </span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：独特的绿色金属初级炸药的合成：3,3'-Azo-5,5'- diazido-1,2,4-三唑</span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704014187941.html">Synthesis and explosive properties of 5,5'-dinitro-3,3'-azo-1H-1,2,4-triazole (DNAT)</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Darren L.Naud&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Darren L.Naud,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Michael A.Hiskey&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Michael A.Hiskey,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Herbert H.Harry&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Herbert H.Harry </a> <a href="/journal-foreign-34275/" target="_blank" rel="nofollow" class="tuijian_authcolor">Journal of Energetic Materials .</a> <span>2003</span><span>,第1期</span> </span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：5,5'-二硝基-3,3'-偶氮-1H-1,2,4-三唑（DNAT）的合成及爆炸特性</span> </p> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/academic-journal-foreign_journal-the-american-chemical-society_thesis/0204111843044.html">Synthesis and Promising Properties of a New Family of High-Density Energetic Salts of 5-Nitro-3-trinitromethyl-1H-1,2,4-triazole and 5,5'-Bisdrinitromethyl)-3,3'-azo-1H-1,2,4-triazole</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Venugopal Thottempudi&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Venugopal Thottempudi,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jeanne M. 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class="tuijian_auth tuijian_authcolor"> . 张恒文</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李燕萍&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,李燕萍</a> <span> <a href="/journal-cn-11569/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 合成化学 </a> </span> <span> . 2015</span><span>,第007期</span> </span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/academic-journal-cn_chinese-journal-explosives-propellants_thesis/0201227175791.html">1,1'-二(硝氧甲基)-3,3'-二硝基-5,5'-联-1,2,4-三唑的合成及性能</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王子俊&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 王子俊</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=葛忠学&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,葛忠学</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=邱少君&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,邱少君</a> <span> <a href="/journal-cn-8327/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 火炸药学报 </a> </span> <span> . 2014</span><span>,第005期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-42822_thesis/020222864187.html">高氮1,1'-二羟基-5,5'-偶氮四唑-3,4-二氨基-1,2,4-三唑含能离子盐(DATr·AZO)：合成及性能研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张至斌&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 张至斌</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=ZHANG Zhi-bin&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,ZHANG Zhi-bin</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=殷昕&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,殷昕</a> <span> <a href="/conference-cn-42822/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 2016年第七届含能材料与钝感弹药技术学术研讨会 </a> <span> <span> . 2016</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020314610024.html">3,3',5,5'-四芳（烷）氧基-4,4'-联-1,2,4-三唑的合成与表征</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张丽娟&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 张丽娟</a> <span> . 2016</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061203484446.html">5,5’-二(三硝基甲基)-3,3’-H,H’-联-1,2,4-三唑及合成方法</a> <b>[P]</b> . <span> 中国专利： CN106632105B </span> <span> . 2019.09.17</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120109127988.html">5,5’‑二(三硝基甲基)‑3,3’‑H,H’‑联‑1,2,4‑三唑及合成方法</a> <b>[P]</b> . <span> 中国专利： CN106632105A </span> <span> . 2017-05-10</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130455337790.html">1,1'-DIGLYCIDYL-3,3'-DIETHYLBIS-(1,2,4-TRIAZOLE-5-ONE-4-YL)- -METHANE SHOWING ANTITUMOR ACTIVITY AND 3,3'-DIETHYLBIS-(1,2,4-TRIAZOLE-5-ONE-4-YL)-METHANE AS AN INTERMEDIATE COMPOUND FOR SYNTHESIS OF 1,1'-DIGLYCIDYL-3,3'-DIETHYLBIS-(1,2,4-TRIAZOLE-5-ONE-4-YL)- -METHANE</a> <b>[P]</b> . <span> 外国专利：  SU1658606A1 </span> <span> . 1997-07-20</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：1,1'-二乙二醇-3,3'-二乙基-（1,2,4-三唑-5-一-4-基）-甲氧基显示抗张活性和3,3'-二乙基-（1,2， 4-三唑-5-一-4-基）-甲烷作为合成1,1'-二糖基-3,3'-二乙基-（1,2,4-三唑-5-ONE-4-的中间体） YL）--甲烷 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130409006991.html">PROCESS FOR PREPARING 3,3'-DINITRO-5,5'-BIS(1<I>H</I>-1,2,4-TRIAZOLE)</a> <b>[P]</b> . <span> 外国专利：  WO2017013206A1 </span> <span> . 2017-01-26</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：制备3,3'-DINITRO-5,5'-BIS（1 <I> H </ I> -1,2,4-三唑）的过程 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130408449905.html">A method for the production of 3,3 '- dinitro - 5,5' - to (1h - 1,2,4 - triazole)</a> <b>[P]</b> . <span> 外国专利：  DE102015009297A1 </span> <span> . 2017-01-26</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：生产3,3'-二硝基-5,5'-到（1h-1,2,4-三唑）的方法 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" 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