Synthesis and Characterization of 2,2′‐Dinitramino‐5,5′‐bi(1‐oxa‐3,4‐diazole) and Derivatives as Economic and Highly Dense Energetic Materials
Year: 2017
Type: article
Abstract: 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.
Source: Chemistry - A European Journal
Institution: Ludwig-Maximilians-Universität München
Language: English
Subfield: Mechanics of Materials
Field: Engineering
Domain: Physical Sciences
Open Access status: bronze
Funder: Office of Naval Research
Awards: G3212964538, G5909962269, G8876996369
OpenAlex ID: W2736710529