Dinitroglycoluril (DNGU) is a high explosive[1] chemical compound with the formula C4H4N6O6. Dinitroglycoluril is of growing interest due to its stability, ability to mix with oxygen positive explosives to form composites, and it is a precursor to tetranitroglycoluril.[2]
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| Names | |
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| IUPAC name
3,6-dinitro-1,3a,4,6a-tetrahydroimidazo[4,5-d]imidazole-2,5-dione
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| Other names
DNGU
1,4-dinitroglycoluril | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.054.239 |
| EC Number |
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| MeSH | 1,4-dinitroglycoluril |
PubChem CID
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| UN number | 0489 |
CompTox Dashboard (EPA)
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| Properties | |
| C4H4N6O6 | |
| Molar mass | 232.112 g·mol−1 |
| Density | 1.94 g/cm3[1] |
| Boiling point | 252.87 °C (explosive decomposition) |
| Thermochemistry | |
Std molar
entropy (S⦵298) |
128.4 J/(mol·K)[1] |
Std enthalpy of
formation (ΔfH⦵298) |
-74 kcal/mol[2] |
| Explosive data | |
| Detonation velocity | 8450 m/s[1] |
| Related compounds | |
Related compounds
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Glycoluril |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and decomposition
editDinitroglycoluril can be created by nitrating glycoluril with concentrated nitric acid.[3]
- C4H6N4O2 + 2 HNO3 → C4H4N6O6 + 2 H2O
The activation energy required to begin decomposition of dinitroglycoluril is 165 kJ/mol.[2] When dinitroglycoluril is heated to 243 °C in an inert atmosphere, the two nitrate groups break off and the two central carbon atoms form a double bond.[1]
Sensitivity
editThe impact sensitivity of dinitroglycoluril was determined using the Bruceton-staircase procedure, which found a h50 of 88 cm. Friction sensitivity was determined by a Julius-Peters apparatus, which found a sensitivity of 25 kg.[2]
References
edit- ^ a b c d e Zhao, Feng-Qi; Rong-Zu, Hu; Chen, Pei; Luo, Yang; Gao, Sheng-Li; Song, Ji-Rong; Shi, Qi-Zhen (2010-08-26). "Kinetics and mechanism of the exothermic first-stage decomposition reaction of dinitroglycoluril". Chinese Journal of Chemistry. 22 (7): 649–652. doi:10.1002/cjoc.20040220707.
- ^ a b c d Khire, V; Talawar, M; Prabhakaran, K; Mukundan, T; Kurian, E (2005-03-17). "Spectro-thermal decomposition study of 1,4-dinitroglycoluril (DINGU)". Journal of Hazardous Materials. 119 (1–3): 63–68. doi:10.1016/j.jhazmat.2004.12.020. PMID 15752849.
- ^ Boileau, J.; Wimmer, E.; Gilardi, R.; Stinecipher, M. M.; Gallo, R.; Pierrot, M. (1988-04-15). "Structure of 1,4-dinitroglycoluril". Acta Crystallographica Section C Crystal Structure Communications. 44 (4): 696–699. doi:10.1107/S0108270187012204.