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- Publisher
- Wiley
- Copyright
- © 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 2192-6506
- eISSN
- 2192-6506
- DOI
- 10.1002/cplu.201800318
- Publisher site
- See Article on Publisher Site
Abstract
Three isomeric dinitropyrazoles (DNPs) were synthesized starting from readily available 1H‐pyrazole by slightly improved methods than described in the literature. 3,4‐Dinitropyrazole (3), 1,3‐dinitropyrazole (4), and 3,5‐dinitropyrazole (5) were obtained and compared to each other with respect to thermal stability, crystallography, sensitivity and energetic performance. Two isomers (3 and 4) show high densities (1.79 and 1.76 g cm–3) and interesting thermal behavior as melt‐castable materials (3: Tmelt.=71 °C, Tdec.=285 °C; 5: Tmelt. = 68 °C, Tdec.=171 °C). Furthermore, eight salts (sodium, potassium, ammonium, hydrazinium, hydroxylammonium, guanidinium, aminoguanidinium and 3,6,7‐triamino‐[1,2,4]triazolo[4,3‐b][1,2,4]triazole (TATOT) of 3 and 5 were synthesized in order to tune performance and sensitivity values. These compounds were characterized using 1H, 13C, 14N, 15N NMR and IR spectroscopy as well as mass spectrometry, elemental analysis and thermal analysis through differential scanning calorimetry. Crystal structures of 14 compounds were obtained (3–7, 10–12 and 15–20) by low‐temperature single crystal X‐ray diffraction. Impact, friction and electrostatic discharge (ESD) values were also determined by standard methods. The sensitivity values range between 8.5 and 40 J for impact and 240 N and 360 N for friction and show mainly insensitive character. The energetic performances were determined using recalculated X‐ray densities, heats of formation and the EXPLO5 code and support the energetic character of the title compounds. The calculated energetic performances (VD: 6245–8610 m s−1; pCJ: 14.1–30.8 GPa) were compared to RDX ((O2NNCH2)3).
Journal
ChemPlusChem – Wiley
Published: Jan 1, 2018
Keywords: ; ; ; ;