Premium
Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes
Author(s) -
Fischer Dennis,
Gottfried Jennifer L.,
Klapötke Thomas M.,
Karaghiosoff Konstantin,
Stierstorfer Jörg,
Witkowski Tomasz G.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609267
Subject(s) - explosive material , methane , detonation , chemistry , diazo , nitrogen , thermal stability , inorganic chemistry , organic chemistry
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 (T dec =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 (V det (theor)=9304 m s −1 versus V det (exp)=9910 m s −1 ) in the range of that of CL‐20. Also, the thermal stability (T dec =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).