| Title |
Effective synthesis, thermal properties and X-ray structure determination of 6,7,8,9-tetranitro-3,4-dihydro-2H-1,5-benzodioxepine (TNDX), a potential thermally stable high energy material |
| Authors |
Šarlauskas, Jonas |
| DOI |
10.22211/cejem/224883 |
| Full Text |
|
| Is Part of |
Central European journal of energetic materials.. Warszawa : Łukasiewicz Research Network – Institute of Industrial Organic Chemistry. 2026, vol. 23, Nr. 2, p. 153-169.. ISSN 1733-7178. eISSN 2353-1843 |
| Keywords [eng] |
6,7,8,9-tetranitro-3,4-dihydro-2H-1,5-benzodioxepine ; TNDX ; synthesis ; X-ray crystallography ; thermal analysis ; energetic materials |
| Abstract [eng] |
This work is dedicated to the investigation of the preparation, single crystal structure determination and physicochemical properties of fused O-heterocyclic 1,5-benzodioxepine completely nitrated in the aromatic ring. Efficient synthetic procedures are described for the precursor 3,4-dihydro-2H-1,5-benzodioxepine and its main polynitro derivatives: 7,8-dinitro-, 6,7,8-trinitro-, and 6,7,8,9-tetranitro-3,4-dihydro-2H-1,5-benzodioxepine (TNDX). The detailed structure of TNDX has been investigated by X-ray crystallography. This compound crystallizes from 2-butanone in the monoclinic space group P21/c. An experimental density of 1.805 g/cm3 was determined by X-ray crystal analysis and it was found to be in good agreement with the value obtained by computer calculations (1.799 g/cm3). Spectral analysis was performed using FT-IR, RAMAN, and NMR spectroscopy. The calculated oxygen balance (OB/CO2 = –53.31%) was very similar to the OB of known high-energy materials, including TATB (C6H6N6O6) and N-ethyltetryl (C8H7N5O8). Preliminary investigation suggests that TNDX (C9H6N4O10) may serve as a potential high-energy material, exhibiting generally favorable physicochemical properties. Thermogravimetric analysis revealed a decomposition temperature of 286 °C, exceeding that of the benchmark energetic compound RDX and approaching the thermal stability of the heat-resistant energetic material DATB (1,3-diamino-2,4,6-trinitrobenzene). Taken together, these results highlight that underexplored oxygen-containing fused cyclic aromatic polynitro compounds could be promising candidates for thermally stable energetic materials with the desirable physicochemical properties. |
| Published |
Warszawa : Łukasiewicz Research Network – Institute of Industrial Organic Chemistry |
| Type |
Journal article |
| Language |
English |
| Publication date |
2026 |
| CC license |
|
