Dinitroglycoluril
{{Chembox
| Name = Dinitroglycoluril
| ImageFile = Dinitroglycoluril.svg
| OtherNames = DNGU
1,4-dinitroglycoluril
| IUPACName = 3,6-dinitro-1,3a,4,6a-tetrahydroimidazo[4,5-d]imidazole-2,5-dione
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| CASNo = 55510-04-8
| CASNo_Ref = {{Cascite|correct|CAS}}
| PubChem = 62101
| ChemSpiderID = 55937
| EC_number = 259-683-0
| UNNumber = 0489
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| MeSHName = 1,4-dinitroglycoluril
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| SMILES = C12C(NC(=O)N1[N+](=O)[O-])N(C(=O)N2)[N+](=O)[O-]
| 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)
| InChIKey = YZTLXSKKFIMAKY-UHFFFAOYSA-N
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| Section2 = {{Chembox Properties
| C = 4 | H = 4 | N = 6 | O = 6
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| BoilingPt = 252.87 °C (explosive decomposition)
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| Section3 = {{Chembox Structure
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| Section4 = {{Chembox Thermochemistry
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| Section6 = {{Chembox Explosive
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| Section7 = {{Chembox Hazards
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| Section8 = {{Chembox Related
| OtherFunction =
| OtherCompounds = Glycoluril
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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.{{Cite journal |last1=Boileau |first1=J. |last2=Wimmer |first2=E. |last3=Gilardi |first3=R. |last4=Stinecipher |first4=M. M. |last5=Gallo |first5=R. |last6=Pierrot |first6=M. |date=1988-04-15 |title=Structure of 1,4-dinitroglycoluril |url=http://scripts.iucr.org/cgi-bin/paper?S0108270187012204 |journal=Acta Crystallographica Section C Crystal Structure Communications |volume=44 |issue=4 |pages=696–699 |doi=10.1107/S0108270187012204|doi-access=free }}
:{{chem2|C4H6N4O2 + 2 HNO3 -> C4H4N6O6 + 2 H2O}}
The activation energy required to begin decomposition of dinitroglycoluril is 165 kJ/mol.{{Cite journal |last1=Khire |first1=V |last2=Talawar |first2=M |last3=Prabhakaran |first3=K |last4=Mukundan |first4=T |last5=Kurian |first5=E |date=2005-03-17 |title=Spectro-thermal decomposition study of 1,4-dinitroglycoluril (DINGU) |url=https://linkinghub.elsevier.com/retrieve/pii/S030438940400648X |journal=Journal of Hazardous Materials |language=en |volume=119 |issue=1–3 |pages=63–68 |doi=10.1016/j.jhazmat.2004.12.020|pmid=15752849 }} 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.