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Author: Subject: Synthesis Octanitrocubane
anonymous201
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[*] posted on 21-10-2011 at 08:59
Synthesis Octanitrocubane


It was looking in Google for Octanitrocubano's synthesis but i dont find nothing,as you can see the Molecular formula C8N8O16 is not dificult i thing syntheis lc-20 is much more dificult than OCN...

Some help please...

800px-Octanitrocubane_synthesis.png - 191kB
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quicksilver
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[*] posted on 21-10-2011 at 09:44


First of all you misspelled the material. It is Octanitrocubane.
C8(NO2)8)
The synthesis is considered a lab curiosity as it is even more expensive in completion than common precious metals.

Octanitrocubane was first synthesized by Philip Eaton (who was also the first to synthesize cubane in 1964) and Mao-Xi Zhang at the University of Chicago in 1999, with the structure proven by crystallographer Richard Gilardi of the United States Naval Research Laboratory.

It was Phil Eaton who had said is was more expensive than gold in a lecture series in 1999, so putting that price back, it's still ridiculous. It was in the same commercial class as CL20 - it's cost made it impractical for applications beyond serious research in cubane(s).

Common source material: Philip E. Eaton, Mao-Xi Zhang, Richard Gilardi, Nat Gelber, Sury Iyer, Rao Surapaneni (2001). "Octanitrocubane: A New Nitrocarbon". Propellants, Explosives, Pyrotechnics.
Astakhov AM, Stepanov RS, Babushkin AY (1998). "On the detonation parameters of octanitrocubane". Combustion Explosion and Shock Waves 34 (1): 85–87.

It's all over research libraries & most likely has a page or more of patents related.




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anonymous201
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[*] posted on 21-10-2011 at 09:55


Quote: Originally posted by quicksilver  
First of all you misspelled the material. It is Octanitrocubane.
C8(NO2)8)
The synthesis is considered a lab curiosity as it is even more expensive in completion than common precious metals.

Octanitrocubane was first synthesized by Philip Eaton (who was also the first to synthesize cubane in 1964) and Mao-Xi Zhang at the University of Chicago in 1999, with the structure proven by crystallographer Richard Gilardi of the United States Naval Research Laboratory.

It was Phil Eaton who had said is was more expensive than gold in a lecture series in 1999, so putting that price back, it's still ridiculous. It was in the same commercial class as CL20 - it's cost made it impractical for applications beyond serious research in cubane(s).

Common source material: Philip E. Eaton, Mao-Xi Zhang, Richard Gilardi, Nat Gelber, Sury Iyer, Rao Surapaneni (2001). "Octanitrocubane: A New Nitrocarbon". Propellants, Explosives, Pyrotechnics.
Astakhov AM, Stepanov RS, Babushkin AY (1998). "On the detonation parameters of octanitrocubane". Combustion Explosion and Shock Waves 34 (1): 85–87.

It's all over research libraries & most likely has a page or more of patents related.


Ok But why is so expensive to do it?
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fledarmus
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[*] posted on 21-10-2011 at 10:39


"More expensive than gold" isn't saying much for an organic research compound. Gold is only about $1650/oz (troy), which is about $53/g. If you are looking for libraries of compounds to test in medicinal chemistry research, they will run about $50 for 10mg delivered. We have gotten quotes for larger scale syntheses that run up to $10,000 for 10 g of material which weren't out of line.
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stygian
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[*] posted on 21-10-2011 at 10:41


This lengthy procedure probably has a pitiful small overall yield.

That's not to mention the reagents, thionyl chloride and especially phosgene are probably both controlled as chemical weapons, i dont know about the TMS azide, DMDO iirc is produced only as a very dilute solution, N2O4, NOCl, may not be things you can just buy, it probably has to be done with extreme refrigeration to prevent burning everything to CO2, and ozonation is probably a lengthy and inefficient procedure. Thats assuming you can even get the starting cubane-carboxylic acid.
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quicksilver
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[*] posted on 21-10-2011 at 10:52


The funny part was he made the comment in '99. If I'm correct it was hovering at about $300. However to be fair it may have been in context of a gram or in comparison to industrial energetics. The medical radiological materials are astoundingly expensive (that's probably one of the reasons why no one has ever made a completed element collection). :D



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Endimion17
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[*] posted on 21-10-2011 at 16:07


anonymous201, stick to the 3D software. I enjoy "synthesizing" weird compounds like this one for no extra cost in ChemSketch, for example. :)



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anonymous201
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[*] posted on 21-10-2011 at 16:11


Quote: Originally posted by Endimion17  
anonymous201, stick to the 3D software. I enjoy "synthesizing" weird compounds like this one for no extra cost in ChemSketch, for example. :)


What you mean?
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Endimion17
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[*] posted on 21-10-2011 at 16:26


I suggest googling ChemSketch... That's what I usually do when ... ah, I'm too tired for this. :(



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AndersHoveland
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[*] posted on 22-10-2011 at 01:49


This link has already been posted several times before, and I will post it again: https://sites.google.com/site/energeticscribble/comparison-w...

It is just a crude summary of the synthesis and available information about ONC. If you look carefully, it appears that acetone peroxide is one of the regents for the synthesis!

[Edited on 22-10-2011 by AndersHoveland]
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[*] posted on 22-10-2011 at 05:45


Andres, may you post your sources of experimentally observed detonation velocities of cubanes?
Thank you in advance.

[Edited on 22-10-2011 by simply RED]




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AndersHoveland
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[*] posted on 22-10-2011 at 06:09


I did not write any experimentally observed detonation velocities for any of the cubanes, including ONC.

The 10.1 km/sec value is only predicted for ONC at a density of 2.1 g/cm3, and such a density has never yet been obtained. The ONC that has been experimentally prepared only has a density of 1.979 g/cm3.
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simply RED
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[*] posted on 22-10-2011 at 08:57


A citation from your site:
"Although it has one less nitro group, heptanitrocubane has a higher observed detonation velocity than the current observations for ONC. "




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stygian
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[*] posted on 22-10-2011 at 10:40


Your 'acetone peroxide' is known as DiMethylDiOxirane , not the dimer or trimer commonly referred to as AP.
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[*] posted on 24-10-2011 at 00:00


To my mind, if the theoretically predicted properties of nitrocubanes are true, they are the energetic materials of the future. There is nothing else with such low sensitivity and thermal stability and having such power...



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AndersHoveland
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[*] posted on 8-12-2011 at 00:43


Quote:

We have investigated molecular, chemical, and explosive properties of a series of azacubane derivatives where nitro groups were substituted to all the carbon atoms in the ring. We have examined the trend of heats of formation, densities, C-J pressure, detonation velocities, and detonation energies of a series of nitroazacubanes starting from octanitrocubane to octaazacubane by replacing C-NO2 group to N atom. Solid phase heats of formation of nitroazacubanes were all the higher than that of octanitrocubane, and were increased by the amount of ca. 25 kcal/mol due to each replacement of C-NO2 group to N atom.

Our predictions showed that the explosive performance got better as more C-NO2 groups were replaced to N atom in a cubane skeleton. The predicted pressures and detonation velocities in most of nitroazacubanes were estimated to be comparable to or somewhat better, in most of series of molecules, than HNIW [alternatively referred to as CL-20], which is known to be one of the most powerful explosive molecules


http://acs.confex.com/acs/serm08/techprogram/P62992.HTM

[Edited on 8-12-2011 by AndersHoveland]
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Thraxx
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[*] posted on 24-10-2016 at 10:26


Hm,to clever for me,but only the last step-the oxidation of NO to NO2,,, could this be done by the R-salt and convert it with ozon into RDX?
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[*] posted on 31-10-2016 at 05:23


Quote: Originally posted by Thraxx  
Hm,to clever for me,but only the last step-the oxidation of NO to NO2,,, could this be done by the R-salt and convert it with ozon into RDX?

What last step oxidation of -N=O to -NO2?
Into the first diagram they go straight from -NH2 to -NO2 via dimethyldioxirane (DMDO)...
It is not written into extension but they use the rearrangement of -CO-N3 intoto -N=C=O ...
R-CO-N3 --> R-N=C=O + N2(g)
R-N=C=O + H2O --> R-NH2 + CO2(g)

The oxydation of -N=O to -NO2 will be easier.
I have never read of nitrosamine to nitramine conversion that way.
Only references for such reactions are to be found:
-for primary amines onto a tertiary carbon...thus a carbon linked to 3 carbons..
(CH3)3C-NH2 -oxydant-> (CH3)3C-NO2
Even KMnO4 is spoken about to perform the oxydation but probably less efficient than DMDO ((CH3)2C(O)2).
-for aromatic amine (anilines) via diazotation and nitrite anion with copper.




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Thraxx
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[*] posted on 31-10-2016 at 12:49


Sorry,I was patterned of other schematics publicated on page 53 here : http://theses.cz/id/8ugheo/PL_BP_07052014_MC_987.pdf
there is the last step other and there is written,that in the future should it be synthetised like tetramer of dinitroacetylene,which was yet not synthetised.I found it funny.

[Edited on 15-10-2016 by Thraxx]
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[*] posted on 31-10-2016 at 15:03


Quote: Originally posted by Thraxx  
Sorry,I was patterned of other schematics publicated on page 53 here : http://theses.cz/id/8ugheo/PL_BP_07052014_MC_987.pdf
there is the last step other and there is written,that in the future should it be synthetised like tetramer of dinitroacetylene,which was yet not synthetised.I found it funny.

[Edited on 15-10-2016 by Thraxx]

Dinitroacetylen (if it existed long enough) might just aswel trimerizes to hexanitrobenzene, dimerizes to tetranitrotetraedrane, multimerizes to higher multimers or polymerizes to higher 1D or 2D polymers...

[Edited on 31-10-2016 by PHILOU Zrealone]




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