Dinitroglycoluril

Last updated
Dinitroglycoluril
Dinitroglycoluril.svg
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.054.239 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 259-683-0
MeSH 1,4-dinitroglycoluril
PubChem CID
UN number 0489
  • 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
  • C12C(NC(=O)N1[N+](=O)[O-])N(C(=O)N2)[N+](=O)[O-]
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
(S298)
128.4 J/(mol·K) [1]
-74 kcal/mol [2]
Explosive data
Detonation velocity 8450 m/s [1]
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).

Dinitroglycoluril (DNGU) is a high explosive [1] chemical compound with the formula C 4 H 4 N 6 O 6. 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]

Contents

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]

Related Research Articles

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<span class="mw-page-title-main">Silver nitrate</span> Chemical compound

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3
. It is a versatile precursor to many other silver compounds, such as those used in photography. It is far less sensitive to light than the halides. It was once called lunar caustic because silver was called luna by ancient alchemists who associated silver with the moon. In solid silver nitrate, the silver ions are three-coordinated in a trigonal planar arrangement.

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<span class="mw-page-title-main">Silver acetylide</span> Chemical compound

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<span class="mw-page-title-main">Erythritol tetranitrate</span> Chemical compound

Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN, though it is thought to be slightly more sensitive to friction and impact.

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<span class="mw-page-title-main">Nitrate ester</span> Chemical group (–ONO2)

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References

  1. 1 2 3 4 5 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. 1 2 3 4 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 .