Sciencemadness Discussion Board

Another caged nitramine

Engager - 3-8-2008 at 11:07

Hi all, recently i got some interesting information about compound shown on picture below. It's very powerfull exposive, even more then CL-20 and HMX. Only drawback it is hydrolized by water on boiling and looses one nitrogroup.

Properties of compound: Melting point 205C (with decomp.) explodes at 210C. Crystall density 2.07 g/cm3, heat of explosion 5.84 megajoules/kg. Sensitivity to impact is on HMX level 21cm with 2.5 kg weight (HMX - 26 cm). Detonation velocity 9800 m/sec, detonation pressure 46.1 GPa, throwing ability is 118% of HMX (HNIW - 108%).

Compound can be made in completely referenced route starting from glyoxal and formamide. Using the following route:

Any oppinions?

Engager - 3-8-2008 at 11:43

Boyer and coworkers reported the synthesis of cis-syn-cis-2,6-dioxo-1,3,4,5,7,8-hexanitrodecahydro- 1H,5H-diimidazo[4,5-b:40,50-e]pyrazine (16) and cissyn- cis-2,6-dioxo-1,4,7,8-tetranitrodecahydro-1H,5Hdiimidazo[ 4,5-b:40,50-e]pyrazine (17) by nitration of the parent dihydrochloride salt with 20% N2O5/HNO3 or Ac2O/HNO3, respectively. Compound 16 which has a crystaldensity of 2.07 g/ml,the highestdensity recorded for a C, H, N, O explosive, decomposes explosively at 210 8C and is decomposed easily with water. Compound 16 is probably the most powerful explosive synthesized to date.

Axt - 3-8-2008 at 12:12

I wouldn't call it a caged structure, tricyclic.

I attached this previously, J. Org. Chem. vol. 56, pp. 3413-3419 (1991).

If you do a search for HHTDD you'll pull up a bit more information.

Chinese Journal of Structural Chemistry, vol. 22, pp. 223-227 (2003) gives measured velocity of 9019m/s @ 1.862g/cm3, 9546 @ 1.995 and extrapolated to 9800 @ 2.07 (TMD).

I aquired the needed precursors; glyoxal, formamide and P2O5 though never went through with it.

Why do you say its hydrolised losing one nitro group? One would expect the two dinitrourea moieties to hydrolyse yielding 4 primary nitramine groups, releasing CO2.

[Edited on 4-8-2008 by Axt]

Ritter - 3-8-2008 at 12:58

These compounds are very similar to tetranitroglycouril. The attached graphic comes from a 1984 SNPE patent: It too is made from glyoxal & formamide. It doesn't take much imagination to get from there to the more elaborate structures you've shown.

[Edited on 3-8-2008 by Ritter]

Tetranitroglycouril.jpg - 3kB

Engager - 7-4-2009 at 18:33

Synth of this compound was successful, description can be found in this topic:

[Edited on 8-4-2009 by Engager]