This popped up on one of the blogs I was reading. I wouldn't be surprised if it was already pretty familiar to the high-energy people here, but the
write up was pretty cool! And it was new to me...
You really should have done a google search of this forum before you made this post,
Hexanitrohexaazaisowurtzitane, also known as HNIW or alternatively as Cl-20, has been well described here. http://www.sciencemadness.org/talk/viewthread.php?tid=3410
This article may become significant if only for the first citation of the phrase "limb-to-chemist ratio".
Ha!
But in all seriousness, this PDF from China Lake offers some interesting reading. In it, they mention a viable route to CL-20 with environmental advantages over the
cholorotoluene/benzylamide/Pearlman's catalyst route, and in fact their new route looks like something a garage chemist might actually have a shot at
making.
Anyone want to explore the "limb-to-chemist ratio" of Hexaallylhexaazaisowurtzitane nitrolysis?quicksilver - 2-12-2011 at 14:14
CL-20 competes for one of the more expensive energetic materials in private and military industry (@ $1000 per KG in a plant-scale modality and much,
much more in a lab). In fact on a smaller scale is may be the most expensive secondary energetic material in comparative costs ever used (not lab
curiosities). In VERY high end mission critical operations CL-20 (and true ultra pure, consistent size single micron cobalt (and nickel) powder top
the charts of non-radio-active chemical expenditure in Dept. of defense chemical budgetary constraints. The smaller one attempts to synthesize CL-20,
the higher the cost rises! That was why TATB was used in MANY substitution papers & projects.
In comparison PLANT-SCALE synthesis of TATB could be mfg for roughly sixteen cents a pound. High quality HNS, HMX, etc would cost barely 20% more and
due to newer plant techniques, TNT would cost so little, it's till used.
Se: ISEE web site for cost containment of military, industrial energetic materials by yearly basis.AndersHoveland - 3-12-2011 at 01:40
this PDF from China Lake offers some interesting reading. In it, they mention a viable route to CL-20, and in fact their new route looks like
something a garage chemist might actually have a shot at making.
So to summarize,
1. allylamine is condensed with glyoxal to form [hexa]allyl- hexazaisowurtzitane. The reaction is apparently very problematic, and they only reported
33% yield. I think the reaction would be much more straight forward, and the yields much higher, if 3-phenylallylamine used instead, because of the
bulky benzene ring groups.
C6H5CH=CHCH2NH2
2. The allyl groups are isomerized by treating with potassium tert-butyloxide in DMSO solvent. No doubt sodium methoxide would work instead, as it is
base catalysed.
R2N-CH2-CH=CH2 --> R2N-CH=CH-CH3
3. The double bonds are simultaneously oxidized, then hydrolyzed off, by concentrated nitric acid, leaving the hexazaisowurtzitane cage nitrolysed.
