Dinitroglycoluril

Dinitroglycoluril
Names
	IUPAC name 3,6-dinitro-1,3a,4,6a-tetrahydroimidazo[4,5-d]imidazole-2,5-dione
	Other names DNGU; 1,4-dinitroglycoluril
Identifiers
CAS Number	55510-04-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	55937;
ECHA InfoCard	100.054.239
EC Number	259-683-0;
MeSH	1,4-dinitroglycoluril
PubChem CID	62101;
UN number	0489
CompTox Dashboard (EPA)	DTXSID70970862 ;
	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[N+](=O)[O-])N(C(=O)N2)[N+](=O)[O-];
Properties
Chemical formula	C4H4N6O6
Molar mass	232.112 g·mol−1
Density	1.94 g/cm3
Boiling point	252.87 °C (explosive decomposition)
Thermochemistry
Std molar; entropy (S⦵298)	128.4 J/(mol·K)
Std enthalpy of; formation (ΔfH⦵298)	-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 [77 °F], 100 kPa). Infobox references

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]

Preparation and decomposition

Dinitroglycoluril 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

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.^[2]

References

^ ^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.

[:0-1] 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.

[Khire-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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