Hexanitrohexaazaisowurtzitane: Difference between revisions
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==Synthesis== |
==Synthesis== |
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First, [[benzylamine]] ('''1''') is condensed with [[glyoxal]] ('''2''') under acidic and dehydrating conditions to yield the first intermediate compound, hexanitrohexaazaisowurtzitane ('''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, yielding dibenzyltetraethanoylhexaazaisowurtzitane ('''4'''). Finally, compound '''4''' is then reacted with [[nitronium tetrafluoroborate]] and [[nitrosonium tetrafluoroborate]], resulting in HNIW. |
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[[File:Synthesis CL20.svg]] |
[[File:Synthesis CL20.svg]] |
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Revision as of 15:44, 26 July 2012
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| Names | |||
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| IUPAC name
2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane[citation needed]
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| Other names
CL-20
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| Identifiers | |||
3D model (JSmol)
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| Abbreviations | CL-20, HNIW | ||
| ChemSpider | |||
| ECHA InfoCard | 100.114.169 | ||
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| C 6N 12H 6O 12 | |||
| Molar mass | 438.1850 g mol-1 | ||
| Explosive data | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane, also called HNIW, and CL-20, is a nitroamine explosive with the formula C6H6N12O12, developed by the China Lake facility, primarily to be used in propellants. It has a better oxidizer-to-fuel ratio than conventional HMX or RDX. It produces 20% more energy than traditional HMX-based propellants, and is widely superior to conventional high-energy propellants and explosives.
While most development of CL-20 has been fielded by the Thiokol Corporation, the US Navy (through ONR) has also been interested in CL-20 for use in rocket propellants, such as for missiles, as it has lower observability characteristics (e.g., less visible smoke).[1]
CL-20 has not yet been fielded in any production weapons system, but is presently undergoing testing for stability, production capabilities, and other weapons characteristics.
Synthesis
First, benzylamine (1) is condensed with glyoxal (2) under acidic and dehydrating conditions to yield the first intermediate compound, hexanitrohexaazaisowurtzitane (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, yielding dibenzyltetraethanoylhexaazaisowurtzitane (4). Finally, compound 4 is then reacted with nitronium tetrafluoroborate and nitrosonium tetrafluoroborate, resulting in HNIW.
See also
- 2,4,6-Tris(trinitromethyl)-1,3,5-triazine
- 4,4’-Dinitro-3,3’-diazenofuroxan (DDF)
- Heptanitrocubane (HNC)
- HHTDD
- Octanitrocubane (ONC)
- Wurtzitane
References
- ^ Yirka, Bob (9 September 2011). "University chemists devise means to stabilize explosive CL-20". Physorg.com. Retrieved 8 July 2012.
- Bolton, Onas (September 12, 2011). "Improved Stability and Smart-Material Functionality Realized in an Energetic Cocrystal". Angewandte Chemie. 123 (38): 9122–9125. doi:10.1002/ange.201104164. Retrieved 8 July 2012.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - Ehrenberg, Rachel (22 October 2011). "Explosive Goes Boom, But Not Too Soon". Science News. 180 (9): 10. Retrieved 8 July 2012.