Hexanitrohexaazaisowurtzitane

Hexanitrohexaazaisowurtzitane, also called HNIW and CL-20, is a nitroamine explosive with the formula C6H6N12O12. The structure of CL-20 was first proposed in 1979 by Dalian Institute of Chemical Physics. In the 1980s, CL-20 was 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 releases 20% more energy than traditional HMX-based propellants, and is widely superior to conventional high-energy propellants and explosives.
Industrial production of CL-20 was achieved in China in 2011, and it was soon fielded in propellant of solid rockets. 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 such as less visible smoke.
CL-20 has not yet been fielded in any production weapons system, but is 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.(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.
Cocrystal product with HMX.
In August 2012, Onas Bolton et al. published results showing that a cocrystal of 2 parts CL-20 and 1 part HMX had similar safety properties to HMX, but with a greater firing power closer to CL-20.
Cocrystal product with TNT.
In August 2011, Adam Matzger and Onas Bolton published results showing that a cocrystal of CL-20 and TNT had twice the stability of CL-20—safe enough to transport, but when heated to 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.
CL-20 covalent chains and networks.
In 2017, K.P. Katin and M.M. Maslov designed one-dimensional covalent chains based on the CL-20 molecules. Such chains were constructed using CH2 molecular bridges for the covalent bonding between the isolated CL-20 fragments. It was theoretically predicted that their stability increased with efficient length growth. A year later, M.A. Gimaldinova and colleagues demonstrated the versatility of CH2 molecular bridges. It is shown that the use of CH2 bridges is the universal technique to connect both CL-20 fragments in the chain and the chains together to make a network (linear or zigzag). It is confirmed that the increase of the effective sizes and dimensionality of the CL-20 covalent systems leads to their thermodynamic stability growth. Therefore, the formation of CL-20 crystalline covalent solids seems to be energetically favorable, and CL-20 molecules are capable of forming not only molecular crystals but bulk covalent structures as well. Numerical calculations of CL-20 chains and networks' electronic characteristics revealed that they were wide-bandgap semiconductors.