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Dinitroglycoluril

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Dinitroglycoluril
Names
IUPAC name 3,6-dinitro-1,3a,4,6a-tetrahydroimidazoimidazole-2,5-dione
Other names DNGU
1,4-dinitroglycoluril
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.054.239 Edit this at Wikidata
EC Number
  • 259-683-0
MeSH 1,4-dinitroglycoluril
PubChem CID
UN number 0489
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H4N6O6/c11-3-5-1-2(8(3)10(15)16)6-4(12)7(1)9(13)14/h1-2H,(H,5,11)(H,6,12)Key: YZTLXSKKFIMAKY-UHFFFAOYSA-N
SMILES
  • C12C(NC(=O)N1(=O))N(C(=O)N2)(=O)
Properties
Chemical formula C4H4N6O6
Molar mass 232.112 g·mol
Density 1.94 g/cm
Boiling point 252.87 °C (explosive decomposition)
Thermochemistry
Std molar
entropy (S298) 		128.4 J/(mol·K)
Std enthalpy of
formation (ΔfH298) 		-74 kcal/mol
Explosive data
Detonation velocity 8450 m/s
Related compounds
Related compounds Glycoluril
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Dinitroglycoluril (DNGU) is a high explosive 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.

Preparation and decomposition

Dinitroglycoluril can be created by nitrating glycoluril with concentrated nitric acid.

C4H6N4O2 + 2 HNO3 → C4H4N6O6 + 2 H2O

The activation energy required to begin decomposition of dinitroglycoluril is 165 kJ/mol. 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.

Sensitivity

The 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.

References

  1. ^ 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.
  2. ^ 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.
  3. 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.
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