Synthesis and Characterization of 2,2′‐Dinitramino‐5,5′‐bi(1‐oxa‐3,4‐diazole) and Derivatives as Economic and Highly Dense Energetic Materials
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.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Jul 21, 2017
- Source ID
- 10.1002/chem.201702191
Entities
People
- Jörg Stierstorfer
- Konstantin Karaghiosoff
- Thomas M. Klapötke
- Tobias S. Hermann
Organizations
- Ludwig-Maximilians-Universität München
- Office of Naval Research