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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: derekb.lowe@gmail.com Twitter: Dereklowe

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November 11, 2011

Things I Won't Work With: Hexanitrohexaazaisowurtzitane

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Posted by Derek

Let's start with the name. Quite a mouthful, isn't it? Believe me, that one's pretty chewy even for experienced organic chemists. We see lots of more complicated nomenclature, of course, but this one some features some speed bumps, that make you go back to make sure that you're reading it correctly. I'll take you through my own thoughts as an example.

You skip to the end in chemical names - Mark Twain would have felt about them the same way he felt about the German language. But this brings me up short, because very few chemists could walk up to the board and draw an isowurtzitane. And I am not among their number. I have a vague picture of these "wurtz" compounds being funky three-dimensional cage structures, and that much only from having probably read too many photochemistry papers over the years. So the only thing that "isowurtzitane" calls to mind is some complicated framework of fused rings, looking like one of those wire sculptures that unexpectedly fold up flat when you pull on them.

Moving on out, as you do in a systematic name, I see that this is a hexaaza variation, which makes the picture a bit fuzzier. That's a lot of nitrogens substituted for carbons, and the first thought is that this must be some weirdo condensation product of ammonia, some aldehyde, and who knows what. You can get some pretty funny-looking structures that way, like hexamethylenetetramine (which I've actually used a couple of times). I don't know where those nitrogens are, I think to myself, but I'll bet that's how they got there, because any other pattern would be a synthetic nightmare. So far, so good. But now comes the unexpected habanero.

Hexanitro? Say what? I'd call for all the chemists who've ever worked with a hexanitro compound to raise their hands, but that might be assuming too much about the limb-to-chemist ratio. Nitro groups, as even people who've never taken a chemistry class know, can lead to firey booms, and putting six of them on one molecule can only lead to such. And since there are six nitrogens and six nitro groups, the first assumption must be that these are all bonded to each other. I mean, come on, leaving the nitro groups attached to the carbons is for wimps. So that means that someone, somewhere, has perversely made a poly-N-nitro cage compound, as if they'd been dared to cram the most bond energy into the smallest space.
272px-CL-20.svg.png
That, as it happens, is exactly the case. Hexanitrohexaazaisowurtzitane, or CL-20, was developed as a highly energetic, compact, and efficient explosive. What makes it unusual is not that it blows up - go find me a small hexa-N-nitro compound that doesn't - but that it doesn't actually blow up immediately, early, and often. No, making things that go off when someone down the hall curses at the coffee machine, that's no problem. Making something like this that can actually be handled and stored is a real accomplishment.

Not that it's what you'd call a perfect compound in that regard - despite a lot of effort, it's still not quite ready to be hauled around in trucks. There's a recent report of a method to make a more stable form of it, by mixing it with TNT. Yes, this is an example of something that becomes less explosive as a one-to-one cocrystal with TNT. Although, as the authors point out, if you heat those crystals up the two components separate out, and you're left with crystals of pure CL-20 soaking in liquid TNT, a situation that will heighten your awareness of the fleeting nature of life.

Stabilized or not, I still won't get near it. For one thing, I'm a drug discovery chemist, and if you think a structure like this is going to be a drug, then you must be on some strong ones yourself. No, the thing about these compounds is that they can be handled as long as they're very pure and formulated just right. The side products from their synthesis, well, those might not be so nice. And if a batch gets contaminated, or doesn't come out so clean, well, that might not be so nice, either. Synthesizing polynitro compounds is no chocolate fondue party, either: if you picture a bunch of guys wheeling around drums of fuming nitric acid while singing the Anvil Chorus from Il Trovatore, you're not that far off the mark. You really have to beat the crap out of a molecule to get that many nitro groups on it, which means prolonged heating of things that you'd really rather not heat up at all.

No, I'll leave the can-you-top-this nitration chemistry to those that love it. You guys just go ahead and stuff as many energetic bonds as you can into the smallest tangles; I'll be over here in the bunker cheering you on, and jumping a foot in the air every time someone sneezes. I'm not cut out for hexanitro anything.

Addendum: it's an odd thing, but when you search for information on this compound, a significant number of the Google hits are for its environmental effects. This is an explosive, meant for munitions and destruction, but there are all kinds of studies on its effects on earthworms, fish, soil microorganisms, and so on. Steven Pinker must be right when he says that violence is getting tamer all the time.

Comments (67) + TrackBacks (0) | Category: Things I Won't Work With


COMMENTS

1. Quintus on November 11, 2011 10:35 AM writes...

They have obviously done all the ecological studies on this compound. Fish tox etal all has to be done before the compound gets produced commercially!

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2. Hap on November 11, 2011 11:00 AM writes...

"Limb-to-chemist ratio" is pretty good. Does it include fingers?

If you're going to make explosives on scale, their environmental hazards might be relevant, considering 1) all the trouble the DOD has over perchlorate and dioxin contamination, and 2) the unintended side effects the weapons might have (note - Vanity Fair link kills my browser and is probably not for the squeamish). Creating a moonscape on land you might want is undesirable, after all.

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3. Hasufin on November 11, 2011 11:01 AM writes...

Well, you've got to salute the dedication it takes to come up with a compound like that. Might be rude, though, I mean, showing off that you still have HANDS, unlike some of those chemists.

It's notable that it's being explored as a propellant, not an explosive. Granted, there's not all that much difference between the two, but that's one hell of a propellant.

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4. DLIB on November 11, 2011 11:03 AM writes...

Yep...lots of research being done for "high" energy metastable ( kinetically trapped ) compounds. We got asked to make some special calorimeters to measure these things for Livermore. Hopefully grab a signal before the calorimeter is shattered.

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5. David P on November 11, 2011 11:32 AM writes...

A hugely entertaining piece of writing, Derek!

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6. milkshake on November 11, 2011 12:16 PM writes...

As far as I remember, HNIW is the record-holder for detonation speed/pressure impulse among all practical high explosives. Apart from armor-piercing applications, they were interested in using HNIW as an oxidizer in solid propellant for missiles with low exhaust signature. I suppose if they make it in bulk for rocket propellant they will need to do the enviro impact.

HNIW is little highly shock sensitive (more than HMX), has several polymorphs that can crystallize at the same time during recrystallization, I think only the one with chunky prisms has the (relatively) manageable shock sensitivity. Formulating it with a binder must be a bitch because HNIW can blow up easily even as a wet slurry.

I like more the high-performance insensitive explosives like FOX-7, 1,1-dinitro-2,2-diaminoethylene, a more powerful cousin of TATB.
By the way, TATB is so insensitive that it is practically impossible to detonate it by accident and since old TATB from disassembled nuclear weapons cannot be recycled it is routinely disposed of by incineration in regular chemical waste furnaces.

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7. Chemjobber on November 11, 2011 12:55 PM writes...

The distinction from "explosive" is sometimes not entirely clear to me.

I assume there's some sort of technical term for "whoosh-yness" versus "boominess." :-)

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8. Tim McDaniel on November 11, 2011 1:17 PM writes...

Hooray! Another TIWWW!

"Nitro groups, as even people who've never taken a chemistry class know, can lead to firey booms": I only learned that from Things I Won't Work With. But now I know enough to flinch when I saw "Hexanitro", and to grin in antici-pation when I saw "hexaaza".

The Wikipedia article says that it was developed as rocket fuel. The distinction from "explosive" is sometimes not entirely clear to me.

Oh, and
http://www.physorg.com/news/2011-09-university-chemists-stabilize-explosive-cl-.html says that they stabilized it by mixing it with TNT, forming a cocrystal. And you can even separate them out again just by heating the mix ... except that the resulting CL-20 is then even more unstable than before.

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9. gippgig on November 11, 2011 1:23 PM writes...

Nitroglycerin is a drug.

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10. Pig Farmer on November 11, 2011 1:39 PM writes...

Just looking at that structure gives me the shakes! Nitrogen tri-iodide is the most explosive compound I've ever made, and I think I'll keep it that way!

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11. RB Woodweird on November 11, 2011 1:42 PM writes...

In 1988 I was attending a meeting at the convention center in Las Vegas when the ammonium perchlorate plant in Henderson, about 6 miles away, detonated. The shock wave rolled through the convention center, knocking rolling doors from their channels and dropping a few ceiling tiles. I could feel the pressure differential in my chest as the shock wave passed. Everyone looked around with a wtf face, because no body had ever experienced anything like it and no body knew what it could have been.

I have no desire to get any closer to high explosives than that.

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12. Simon on November 11, 2011 2:04 PM writes...

My personal favourites for nutty compounds you wouldn't want to duplicate are all those per-azide compounds and complexes made by those, er, brave people in Munich.

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13. RD on November 11, 2011 2:12 PM writes...

Are you sure that's not just a virtual compound? Virtual monstrosities aren't all that uncommon. Modelers dream them up all the time. We're not afraid of chiral carbons either.
You synthesis people are wimps.

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14. Lu on November 11, 2011 3:04 PM writes...

that might be assuming too much about the limb-to-chemist ratio

That. Is. Brilliant.

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15. MLBpitcher_and_MedicinalChemist on November 11, 2011 3:05 PM writes...

I'm surprised that an MLB player like Derek Lowe knows about this molecule.

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16. Nick K on November 11, 2011 3:39 PM writes...

I vaguely remember Phil Eaton et al. several years ago trying to make polynitro derivatives of cubane, the idea being that the strain energy of the cubane would give an added "zing" to the bang. Does anyone know what became of this work?

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17. HelicalZz on November 11, 2011 3:43 PM writes...

Hexa-whoosie-what's-its-name?

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18. HelicalZz on November 11, 2011 3:50 PM writes...

Hexa-whoosie-what's-its-name?

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19. cirby on November 11, 2011 4:06 PM writes...

The environmental study would be summed up very nicely as "this compound is designed to move the environment from right here to somewhere over there."

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20. Hap on November 11, 2011 4:07 PM writes...

16: Octanitrocubane here. Octanitrocubane apparently goes bang nicely (in a matter of speaking), but not as well as expected, and since it's hard to make, it probably won't be used as an explosive anytime soon.

BRSM has a piece on cubane referencing that article.

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21. Chemjobber on November 11, 2011 4:11 PM writes...

@16, Nick:

Google "octanitrocubane" and you'll get the Wikipedia page for it. Synthesized and reported in 2000.

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22. Nick K on November 11, 2011 5:17 PM writes...

Thanks Hap and CJ. I won't try to make it, if you were wondering...

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23. Mildweasel on November 11, 2011 5:54 PM writes...

If I'm reading it right the excess hydrogen makes this a propellent. This thing must have a ferocious impulse.

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24. Bunsen on November 11, 2011 6:18 PM writes...

That name, aside from being a mouthful and slightly terrifying, has quite an appealing meter. One that seems somewhat familiar, in fact. You all know the tune... Everybody now!

Um diddle diddle diddle um diddle boom!
Um diddle diddle diddle um diddle boom!
Hexanitrohexaazaisowurtzitaaane
Even though the synthesis
is something quite insaaane
If you hit it hard enough
You'll lose a window paaane
Hexanitrohexaazaisowurtzitaaane!

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25. Anonymous on November 11, 2011 6:35 PM writes...

I know this is off-topic, but seriously WTF?

"Penn state names Merck's CEO Ken Frazier head of investigative team in sex scandal."

Seriously, Google it. Isn't he supposed to be saving his company?!

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26. Stuff that I will not work with on November 11, 2011 7:12 PM writes...

Anything that can only be isolated in an argon matrix.

I wonder how much bioaccumulation of this compound would be necessary to make an organism detonate? The nitros would probably be inactivated by reductases, but then you would be left with a polyhydrazide...mmm...

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27. Anonymous on November 11, 2011 7:53 PM writes...

@25
SFChronicle reported it. I hope he's better at leading the investigation than he is at leading the company...

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28. Slurpy on November 11, 2011 7:59 PM writes...

@11 Chemjobber

The technical difference between "whooshiness" and "boominess" is whether the shockwave occurs faster than the speed of sound, i.e. deflagration versus detonation.

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29. Jeffrey Soreff on November 11, 2011 9:18 PM writes...

Wonderful column!
"Limb-to-chemist ratio" - Now that is a
_memorable_ phrase!

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30. Doug on November 12, 2011 7:17 AM writes...

Thank you for another in your most awesome 'things I won't work with' series. Stellar, as always.

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31. smurf on November 12, 2011 8:32 AM writes...

Hotzenplotzpumpernickelblitz

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32. Moiety on November 12, 2011 8:44 AM writes...

@ 8 Tim McDaniel

Think instead of detonation and deflagration. A detonation in the simplest of terms is one that is supersonic and its propogates by its shock compression. A deflagration is an explosion below supersonic that propogates though thermal activity. This can also be used as a definition of most fires. However they are also seen in ICE's and guns.

@ 11 RB Woodweird
To add the explosion is documentated on youtube. Look it up directly as well as BLEVE.

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33. Kevin on November 12, 2011 10:02 AM writes...

I did some technical support once for a couple of labs in the SW that test or develop explosives and propellants, both of which use DSC to study explosives. No surprise that both use very, very small sample size. They used the shape of the DSC exotherm, particularly the leading edge, to determine "boominess." In both places, the limb to chemist ratio was fully normal. (Great line that) It was a bit distracting to work next to a room full of C4 however.

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34. Anonymous BMS Researcher on November 12, 2011 10:32 AM writes...

I have sat through MANY a PowerPoint presentation at a working group meeting with SAR tables -- lots of structures with PK and EC90 numbers. How I wish I dared stick THAT structure in the middle of them to see how high people jumped!

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35. 122 on November 12, 2011 10:45 AM writes...

Is it commercially available; I am thinking of adding more "nitros" on to the carbons.

I am disappointed that N is only trivalent.

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36. Nick K on November 12, 2011 11:50 AM writes...

Five star rating to #24 for the lyrics!

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37. Anonymous on November 12, 2011 10:36 PM writes...

Let's push the envelope, so what's the ultimate explosive molecule to date? Just curious....I think it would be cool to compare PETN, nitroglycerin, tnt, NI3 with HNHNW (Hexanitrohexaazaisowurtzitane ) and others including some emulsion explosives. Cap sensitivity and other features such as storage stability and temp. and pressure of detonation when tested in the "pond".

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38. HFM on November 13, 2011 1:57 AM writes...

@34
Now you've got me tempted to play "spot the chemist" with my next presentation. "Before Johnson left, he synthesized this new fluorophore for us...if anyone wants to try it, I've got the bottle here..." (shake shake shake)

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39. Kevin on November 13, 2011 9:44 AM writes...

Did #24 use "2 Ladies" as the melody? 'Cause that's what comes to mind when I hum it...

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40. Dan on November 13, 2011 12:27 PM writes...

Kevin (39): I think he was going for "Supercalifragilisticexpialidocious". And quite well at that.

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41. Karl on November 13, 2011 2:39 PM writes...


The shortened name for the compound cl-20...
the cl stands for China Lake...a military
explosives (among other tings) facility.
As for all those tox. studies....Uncle Sam
has an Eco-friendly face these days, and is
worried about effluents and such.
One scary thing about this beastie is that
it is in semi-commercial scale production.
We are talking multi-kilo batches.
(I, once) cosidered making a gram or two.
It has a significant space in the US Patent
literature.

Karl

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42. Trottelreiner on November 13, 2011 6:00 PM writes...

Well, it might be the drugs I'm on(though that's only caffeine), but I'm not that sure there are no drugs that look like that. As already mentioned, there are some NO donors that look kinda, err, strange(think nitroprusside), so if this stuff released NO without depleting thiol groups like nitroglycerin, it might be interesting.

OTOH, those cagy structures are quite nice with channel blockers, like memantine or tetrodotoxine. So well, NO donor and ion channel(like calcium or potassium) blocking, well, could be something for the cardiovascular guys. Explosive blood pressure, you know.

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43. Demon Pit on November 13, 2011 6:29 PM writes...

I wonder if it could be used in a plutonium-implosion type nuclear device. Something with that much bang might be able to produce criticality with a smaller amount of fissile material. Pocket nukes, anyone?

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44. PharmaHeretic on November 13, 2011 9:25 PM writes...

Pfizer Inc. (PFE) and Bristol-Myers Squibb Co. (BMY)’s experimental drug apixaban wasn’t safer or more effective than a standard treatment in stopping blood clots in the legs and lungs of patients after hospitalization, a study found.

http://www.bloomberg.com/news/2011-11-13/pfizer-bristol-drug-doesn-t-cut-leg-clots-after-hospital-stay.html

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45. Matt B. on November 14, 2011 12:26 PM writes...

#3 I think it is a formulation issue, RDX is used as both a propellent and an explosive.

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46. John Schilling on November 14, 2011 2:52 PM writes...

#3, #45: Method of initiation also matters. C-4 plastic explosive is 90+% RDX, and as is widely known in certain circles will work quite nicely as an explosive or a camp stove fuel. Initiate with a shock, e.g. from a blasting cap, and it detonates. Initiate with an open flame, and it simply burns - there is no bulk transition to detonation.

And the RDX- and HMX-containing propellant compositions tend to be classified DOT 1.1, mass detonation hazard, indicating that regardless of formulation they will detonate if initiated with a suitable shock. Yes, I think it is silly to use such compositions in operational weapons, never mind transportation systems, but it has worked well enough so far. Cross fingers, while I still have all ten...

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47. Baratol Guy on November 14, 2011 9:24 PM writes...

#46
I've never heard of RDX being used as a camp fuel, although hexamine is a common one. Granted, nitrating hexamine will give you RDX, plasticizing that gives you C-4. I suppose RDX (or C-4) would be fun around the campfire, certainly it would give you bragging rights. Just don't try to fly home, since you'll have residue all over you.

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48. medchemistpast on November 15, 2011 5:53 AM writes...

#47

Ask any Marine about using C4 as a fuel. Well known "off label" use. Adds to the attractiveness of always having a pound or two about one's person, at least in some environments.

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49. medchemistpast on November 15, 2011 6:02 AM writes...

#47

Ask any Marine about using C4 as a fuel. Well known "off label" use. Adds to the attractiveness of always having a pound or two about one's person, at least in some environments.

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50. Anonymous on November 15, 2011 11:10 AM writes...

This thread took a very strange turn.......

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51. warlock on November 15, 2011 12:15 PM writes...

I have to comment in appreciation just for the back-to-back double whammy of "the unexpected habanero" followed by "the limb-to-chemist ratio." Brilliant.

Also, I seem to recall that the Mythbusters recently examined C4 as a fuel. I recall something about whether you can stomp out such a fire without (heh heh) modifying the limb-to-soldier ratio...

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52. Time for S'mores on November 15, 2011 4:09 PM writes...

Burning RDX produces a nice hot flame, around 2700 degrees kelvin. Roast marshmallows damn fast.

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53. G. on November 15, 2011 6:08 PM writes...

Hexa-nitro hexa-aza stuff with stoechiometric ratio C/O2 ? great ! have you heard about Hepta and Octa nitro-cubane ? best kaboom ever !
http://en.wikipedia.org/wiki/Octanitrocubane
http://en.wikipedia.org/wiki/Heptanitrocubane

G.

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54. aasdasd on November 16, 2011 5:37 AM writes...

HNIW for Things I Wont work with? Now that is a stretch. In terms of explosive compounds, this one is pretty tame in regards to risk.

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55. keiki on December 19, 2011 12:15 PM writes...

As someone who almost failed intro chemistry in college (but still finds chemistry mind bogglingly fascinating, if not also mind bogglingly obtuse), I love this section of your blog and I wish you'd write entries for it more often!

Also, I'm desperately in love with your writing style.

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56. Dyspeptic Curmudgeon on January 12, 2012 3:02 AM writes...

"I've got the bottle here..." (shake shake shake)"

So that's how a chemist adjusts the limb to chemist ratio...

Actually when I read the beginning of this I was reminded of when I tried to learn gaelic. Starting with para-dimethylaminobenzaldehyde.

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57. me on January 12, 2012 11:16 AM writes...

Heh.

As any chemist can tell you, it's EASY to create something that will go BOOM. The real trick is creating something that won't go BOOM until you want it to!

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58. fuelair on March 1, 2012 8:45 PM writes...

Dyspeptic Curmudgeon: may I assume you are a fan of the good (but sadly passed away) Dr. Asimov?

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59. joeylawn on April 10, 2012 11:18 PM writes...

Also, there's the hypothetical Octaazacubane, eight nitrogens arranged in a cube.

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60. AnonyMouse on May 22, 2012 10:44 AM writes...

"Nitrogen tri-iodide is the most explosive compound I've ever made" .... in High School ... Really probably shouldn't have kept it (wet) in the eye dropper bottle (for toilet seat application) as one still had to unscrew the dropper from the bottle ...

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61. Anonymous on July 29, 2012 9:42 PM writes...

While most chemicals are identified by there shape. I think a more remember-able name for this compound could be developed by the amount of nitrogen and oxygen atoms in it.

It has 12 Ns and 12 Os. Put them together and you learn everything you need to know about this chemical spelled out 12 times,

No No No No No No No No No No No No

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62. Cajun Scientist on March 24, 2013 8:40 AM writes...

Interesting you should say that. It's a bracing wintry morning (beginning of spring, actually, late March) in Denver, Colorado. Having nothing better to do, I googled various explosive molecules until I found myself in the Google Books preview of Jacqueline Akhavan's The Chemistry of Explosives (2nd ed.), on page 16 of which is a diagram of the steric structures of octanitrocubane and heptanitrocubane, the nitro groups shown with the nitrogens touching carbons in the cubane "cube", so that on the left you see O2N, on the right of the cube, NO2.

I showed this to my wife when she demanded to know what I was chortling at... her reaction was "wow... it says 'oh,no oh,no oh,no oh,no'!"

Obviously, she misread the O2N for "OH," but I couldn't help thinking this was the reaction of SOMEONE in the team informed they were actually going to synthesize enough of this stuff to see.

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63. Anonymous on March 26, 2013 10:02 AM writes...

well that's a amusing thing a explosive that gets more stable by combining it with another explosive.

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64. cr on August 4, 2013 4:05 AM writes...

"well that's a amusing thing a explosive that gets more stable by combining it with another explosive."

Not that unusual, Google 'gelignite' or 'blasting gelatin' for example...

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65. Anonymous on October 25, 2013 7:43 AM writes...

This work doesn't look all that surprising. It's simply an attempt to extend the ideas of trinitrotriazacyclohexane (RDX/hexogen) and tetranitrotetraazacyclooctane (HMX/octogen) to three dimensions to get more energy packed in there with a higher bdensity.
RDX and HMX themselves are quite stable high explosives. RDX is the main ingredient in C4 and semtex.
While RDX is moderately toxic (occasionally eaten by soldiers to induce temporary seizures to get them sent home), HMX is sufficiently non-toxic that it was actually disguised during WWII by mixing it with flour. The flour could be used to bake edible pancakes, that were still usable as explosives.
As a CxH2xN2xO2x compound, these can burn cleanly to N2, CO and H20 (not the 'clean' engine manufacturers use, but it leaves only gaseous products and carrying more O around (besides being hard to fit in there) is going to impact performance), and CL-20 contains even less hydrogen.

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66. Ryk E. Spoor on November 21, 2013 10:45 AM writes...


It may amuse you to know that in the current SBIR solicitation, there is a topic titled:

Environmentally Friendly Alternative Synthesis and Process to Manufacture Cost- Effective Hexanitrohexaazaisowurtzitane (CL-20)

with the following objective:

OBJECTIVE: Develop and demonstrate a viable alternate synthesis route for Hexanitrohexaazaisowurtzitane (CL-20) with efforts directed to lowering production costs for CL-20 bulk use.


(I write technical proposals in my day job and the SF/F books by night, so that's why I came across this little gem)

Thanks for Things I Won't Work With, BTW; it's one of the most amusing things I've ever read online!

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67. Explosives Chemist on February 3, 2014 3:03 PM writes...


Actually, CL-20 is a VERY well behaved explosive, if a bit hair-raising to synthesize. I was a synthetic chemist for the company that scaled production up to 1000lb scale. The trickier part is recrystallization to obtain the desired polymorph. Which we also did. Both I and everybody I worked with have not only all of our limbs, but all fingers and toes as well (thank you very much).

I also worked with formulating CL-20 as an explosive and propellant. The different polymorphs DONT have significantly different shock sensitivity, but particle size and purity have effect.

If you want something scary, look at the nitrogen tri-iodide. Now that's something even I wont work with!

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