Hexanitrohexaazaisowurtzitane

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Hexanitrohexaazaisowurtzitane
Names
IUPAC name
2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane
Other names
2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane
CL-20
HNIW
Octahydro-1,3,4,7,8,10-hexanitro-5,2,6-(iminomethenimino)-1H-imidazo[4,5-b]pyrazine
Properties
C6H6N12O12
C6N6H6(NO2)6
Molar mass 438.1850 g/mol
Appearance Yellow solid[1]
Odor Odorless
Density 2.044 g/cm3
Melting point 230–260[2] °C (446–500 °F; 503–533 K) (decomposition)
Boiling point 244 °C (471 °F; 517 K) (decomposes)[3]
Insoluble
Hazards
Safety data sheet None
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hexanitrohexaazaisowurtzitane, also called HNIW and CL-20, is a nitroamine explosive with the formula C6H6N12O12.

Properties

Chemical

HNIW will form cocrystal products with HMX[4] and TNT[5]. The cocrystal product with TNT has twice the stability of CL-20—safe enough to transport, but when heated to 136 °C the cocrystal may separate into liquid TNT and a crystal form of CL-20 with structural defects that is somewhat less stable than CL-20.

HNIW detonates releasing carbon dioxide, water and nitrogen gases.

Physical

HNIW is a yellowish solid, soluble in organic solvents.[6]

Explosive

CL-20 has a better oxidizer-to-fuel ratio than conventional HMX or RDX. It releases 20% more energy than traditional HMX-based propellants, and is widely superior to conventional high-energy propellants and explosives. HNIW has a very high detonation velocity, of 9.38 km/s. It has an OB of -11%.

Availability

This compound is not sold and currently is still under research.

Preparation

Synthesis of CL-20

First, benzylamine (1) is condensed with glyoxal (2) under acidic and dehydrating conditions, using acetonitrile as solvent to yield the first intermediate compound (3). Four benzyl groups selectively undergo hydrogenolysis using palladium on carbon and hydrogen. The amino groups are then acetylated during the same step using acetic anhydride as the solvent. (4). Finally, compound 4 is reacted with nitronium tetrafluoroborate and nitrosonium tetrafluoroborate, resulting in HNIW.[7]

Projects

  • Rocket propellant
  • Explosive material
  • Shaped charges

Handling

Safety

There is limited information regarding the toxicity of this compound. Studies so far have shown to possess a similar toxicity to other nitroamine compounds.

Storage

Best to use it as soon as possible, rather than store it.

Disposal

Controlled incineration or detonation is sufficient.

References

  1. Latypov, Nikolaj V.; Wellmar, Ulf; Goede, Patrick; Bellamy, Anthony J.; Organic Process Research and Development; vol. 4; nb. 3; (2000); p. 156 - 158
  2. Nielsen, Arnold T.; Chafin, Andrew P.; Christian, Stephen L.; Moore, Donald W.; Nadler, Melvin P.; Nissan, Robin A.; Vanderah, David J.; Gilardi, Richard D.; George, Clifford F.; Flippen-Anderson, Judith L.; Tetrahedron; vol. 54; nb. 39; (1998); p. 11793 - 11812
  3. Zhang, Chaoyang; Yang, Zongwei; Zhou, Xiaoqing; Zhang, Chenghua; Ma, Yu; Xu, Jinjiang; Zhang, Qi; Nie, Fude; Li, Hongzhen; Crystal Growth and Design; vol. 14; nb. 8; (2014); p. 3923 - 3928
  4. https://pubs.acs.org/doi/10.1021/cg3010882
  5. https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201104164
  6. Latypov, Nikolaj V.; Wellmar, Ulf; Goede, Patrick; Bellamy, Anthony J.; Organic Process Research and Development; vol. 4; nb. 3; (2000); p. 156 - 158
  7. https://link.springer.com/article/10.1007%2Fs10573-005-0014-2

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