Synthesis and Characterization of 2,2′-Dinitramino-5,5′-bi(1-oxa-3,4-diazole) and Derivatives as Economic and Highly Dense Energetic Materials

5 years ago

Synthesis and Characterization of 2,2′-Dinitramino-5,5′-bi(1-oxa-3,4-diazole) and Derivatives as Economic and Highly Dense Energetic Materials

Jörg Stierstorfer, Konstantin Karaghiosoff, Thomas M. Klapötke, Tobias S. Hermann

2,2′-Dinitramino-5,5′-bi(1-oxa-3,4-diazole) (2) is a new highly energetic material with superior calculated detonation performance in comparison to cyclo-1,3,5-trimethylene-2,4,6-trinitramine (RDX) and penta-erythritoltetranitrate (PETN) and can be prepared by an economical and practical two-step synthesis. The starting material 2,2′-diamino-5,5′-bi(1-oxa-3,4-diazole) (1) is synthesized by the reaction of oxalyl dihydrazide with cyanogen bromide. Nitration of 1 yields the title compound in perfect yield and purity. The combination of its high density of 1.986 g cm−3, the positive heat of formation (+190 kJ mol−1), and a slightly positive oxygen balance (+6.2 %) results in ideal calculated detonation parameters (e.g. detonation velocity 9296 m s−1). The sensitivities toward impact and friction can be adjusted by deprotonation and formation of corresponding nitrogen-rich salts, for example, ammonium (3), hydroxylammonium (4), and guanidinium (5) salts. A new highly energetic material, 2,2′-dinitramino-5,5′-bi(1-oxa-3,4-diazole), was prepared by an economical and practical two-step synthesis. The combination of its high density of 1.986 g cm−3, the positive heat of formation (+190 kJ mol−1), and a slightly positive oxygen balance (+6.2 %) resulted in ideal calculated detonation parameters (e.g. detonation velocity 9296 m s−1).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702191