Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes |
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| Authors: | Dr. Dennis Fischer Dr. Jennifer L. Gottfried Prof. Dr. Thomas M. Klapötke Prof. Dr. Konstantin Karaghiosoff Dr. Jörg Stierstorfer Dipl.‐Ing. Tomasz G. Witkowski |
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| Affiliation: | 1. http://hedm.cup.uni‐muenchen.de;2. Department of Chemistry, University of Munich (LMU), München, Germany;3. RDRL-WML-B, US Army Research Laboratory, Aberdeen Proving Ground, MD, USA |
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| Abstract: | Herein we present the preparation and characterization of three new bispyrazolyl‐based energetic compounds with great potential as explosive materials. The reaction of sodium 4‐amino‐3,5‐dinitropyrazolate ( 5 ) with dimethyl iodide yielded bis(4‐amino‐3,5‐dinitropyrazolyl)methane ( 6 ), which is a secondary explosive with high heat resistance (Tdec=310 °C). The oxidation of this compound afforded bis(3,4,5‐trinitropyrazolyl)methane ( 7 ), which is a combined nitrogen‐ and oxygen‐rich secondary explosive with very high theoretical and estimated experimental detonation performance (Vdet (theor)=9304 m s?1 versus Vdet(exp)=9910 m s?1) in the range of that of CL‐20. Also, the thermal stability (Tdec=205 °C) and sensitivities of 7 are auspicious. The reaction of 6 with in situ generated nitrous acid yielded the primary explosive bis(4‐diazo‐5‐nitro‐3‐oxopyrazolyl)methane ( 8 ), which showed superior properties to those of currently used diazodinitrophenol (DDNP). |
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| Keywords: | diazo compounds energetic materials nitrogen heterocycles pyrazoles X-ray diffraction |
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