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Benzofuroxan (Benzo[1,2-c]1,2,5-oxadiazole N-oxide) Derivatives as Potential Energetic Materials: Studies on Their Synthesis and Properties

Šarlauskas J., Anusevičius Z., Misiunas A.

Central European Journal of Energetic Materials

2012

Vol. 9, nr 4

365-386

The objective of this work was to prepare benzofuroxan derivatives as new, dense, potentially energetic materials and to investigate their properties, with the main focus being on 5,6-dinitrobenzofuroxan (5,6-DNBF). 5,6-DNBF was prepared by a 3-step reaction sequence: a) 1-azido-3-nitrobenzene was synthesized by diazotation of 3-nitroaniline with sodium nitrite and subsequent reaction with sodium azide in acetic/sulfuric mixed acids; b) it was nitrated with HNO3/H2SO4 to 1-azido-2,4,5-trinitrobenzene; c) thermal cyclization of the latter compound in a polar solvent gave the desired 5,6-DNBF (m.p. 177 °C). It was fully characterized by UV/VIS, FT-IR and NMR spectroscopy, mass spectrometry and single crystal X-ray diffraction. The density of the compound (X-ray) was found to be comparatively high (1.88 g/cm3), and to be superior to the previously known, isomeric energetic material ? 4,6-dinitrobenzofuroxan (4,6-DNBF) (1.76 g/cm3). Furthermore, the synthesis of some other benzofuroxan derivatives, potentially interesting as high energy, density materials (HEDMs), has been carried out. The densities of the compounds obtained were calculated using ACD Labs software (version 4.0). Based on the results obtained, it could be concluded that 5,6-DNBF is one of the densest nitro derivatives of the benzofuroxan series, comparable to CL-14, CL-17, CL-18, and thus could have potential applications as an HEDM.

High Energy Density Materials (HEDM): Overview, Theory and Synthetic Efforts at FOI

Östmark H., Wallin S., Goede P.

Central European Journal of Energetic Materials

2007

Vol. 4, nr 1-2

83-108

This paper presents a literature overview of HEDM. A number of potential HEDMs with performances theoretically up to more than 10 times HMX have been identified, ranging from ionic all-nitrogen compounds like N5 - and N5 + with suitable counter ions (N5 +N5 - gives a performance of ~1.6 times HMX) to polymeric nitrogen (10 times HMX) and metallic hydrogen. In between there are for example metastable nitrogen "clusters" (Nx, x𕛔 to 60). Calculations show that N4 has approximately 3.2 times the performance of HMX. Both metallic hydrogen and polymeric nitrogen are high-pressure compounds (several Mbar) and thus probably hard to synthesize in larger amounts. The nitrogen clusters offer an interesting alternative or complement in that they are all "normal" chemical compounds and they all have high heat of explosion, and probably also high density (2.0-2.7 g/cm3). This overview covers conventional chemistry, novel chemistry (all-nitrogen compounds, new oxidizers in the form of NxOy compounds) and exotic physics (eg. metallic hydrogen, cold fusion and anti-matter). The time in which these concepts can be realised ranges from near future to many years ahead and some may possibly never be made at all or perhaps only in lab scale. The overview is complemented with theoretical and experimental results from our institute in our effort to synthesize new all nitrogen compounds, e.g. pentazolate ion (N5 -) and tetraazatetrahedrane (N4(Td)).