Synthesis and characterization of 5-substituted 1,2,4-triazole-3-methyl nitrate as potential high-performance energetic plasticizers

摘要

This paper, the synthesis and characterization of azido functionalized compounds, based on 5-amino-3-hydroxymethyL-1,2,4-triazole, for potential use as an energetic plasticizers is described. The azide group has a high positive heat of formation and it produces environmentally friendly nitrogen gas, the high oxygen content of the-ONO_2 group in nitrate esters provides an easily overoxidized potential and reduces the melting point of compounds. Therefore, the combination of an azide group and a nitrate group is beneficial to improve the performance of the triazole compounds. 5-azido-1,2,4-triazole-3-methyl nitrate as possible high-performance energetic plasticizers have been synthesized and characterized, and its physical and chemical properties have been explored. The energetic material was full characterized by IR, DSC and multinuclear NMR spectroscopy. 5-azido-1,2,4-triazole-3-methyl nitrate was additionally characterized by single crystal X-ray diffractometry. Energetic performance was calculated by using EXPL05 v6.01 based on calculated heats of formation (Gaussian 09) and experimentally determined densities at room temperature. The impact and friction sensitivities were measured via standard BAM method. As a vital property of energetic materials, melting point determines the casting approach of explosives. According to the experimental results and computational analysis, the newly designed energetic materials have a good melting point and excellent detonation properties. Hence, the introduction of nitrate groups into high energy materials may be an effective pathway for designing and synthesizing potential energetic plasticizers.