anonymous201
Harmless
Posts: 31
Registered: 21-10-2011
Location: Spain
Member Is Offline
Mood: No Mood
|
|
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...
|
|
|
quicksilver
International Hazard
Posts: 1820
Registered: 7-9-2005
Location: Inches from the keyboard....
Member Is Offline
Mood: ~-=SWINGS=-~
|
|
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.
|
|
|
anonymous201
Harmless
Posts: 31
Registered: 21-10-2011
Location: Spain
Member Is Offline
Mood: No Mood
|
|
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?
|
|
|
fledarmus
Hazard to Others
Posts: 187
Registered: 23-6-2011
Member Is Offline
Mood: No Mood
|
|
"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.
|
|
|
stygian
Hazard to Others
Posts: 242
Registered: 19-9-2004
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
quicksilver
International Hazard
Posts: 1820
Registered: 7-9-2005
Location: Inches from the keyboard....
Member Is Offline
Mood: ~-=SWINGS=-~
|
|
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). 
|
|
|
Endimion17
International Hazard
Posts: 1468
Registered: 17-7-2011
Location: shores of a solar sea
Member Is Offline
Mood: speeding through time at the rate of 1 second per second
|
|
anonymous201, stick to the 3D software. I enjoy "synthesizing" weird compounds like this one for no extra cost in ChemSketch, for example. 
|
|
|
anonymous201
Harmless
Posts: 31
Registered: 21-10-2011
Location: Spain
Member Is Offline
Mood: No Mood
|
|
| 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?
|
|
|
Endimion17
International Hazard
Posts: 1468
Registered: 17-7-2011
Location: shores of a solar sea
Member Is Offline
Mood: speeding through time at the rate of 1 second per second
|
|
I suggest googling ChemSketch... That's what I usually do when ... ah, I'm too tired for this. 
|
|
|
AndersHoveland
Hazard to Other Members, due to repeated speculation and posting of untested highly dangerous procedures!
Posts: 1986
Registered: 2-3-2011
Member Is Offline
Mood: No Mood
|
|
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]
|
|
|
simply RED
Hazard to Others
Posts: 206
Registered: 18-8-2005
Location: noitacoL
Member Is Offline
Mood: booM
|
|
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]
When logic and proportion have fallen sloppy dead...
|
|
|
AndersHoveland
Hazard to Other Members, due to repeated speculation and posting of untested highly dangerous procedures!
Posts: 1986
Registered: 2-3-2011
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
simply RED
Hazard to Others
Posts: 206
Registered: 18-8-2005
Location: noitacoL
Member Is Offline
Mood: booM
|
|
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. "
When logic and proportion have fallen sloppy dead...
|
|
|
stygian
Hazard to Others
Posts: 242
Registered: 19-9-2004
Member Is Offline
Mood: No Mood
|
|
Your 'acetone peroxide' is known as DiMethylDiOxirane , not the dimer or trimer commonly referred to as AP.
|
|
|
simply RED
Hazard to Others
Posts: 206
Registered: 18-8-2005
Location: noitacoL
Member Is Offline
Mood: booM
|
|
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...
When logic and proportion have fallen sloppy dead...
|
|
|
AndersHoveland
Hazard to Other Members, due to repeated speculation and posting of untested highly dangerous procedures!
Posts: 1986
Registered: 2-3-2011
Member Is Offline
Mood: No Mood
|
|
| 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]
|
|
|
Thraxx
Hazard to Self
Posts: 71
Registered: 15-10-2016
Member Is Offline
Mood: No Mood
|
|
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?
|
|
|
PHILOU Zrealone
International Hazard
Posts: 2893
Registered: 20-5-2002
Location: Brussel
Member Is Offline
Mood: Bis-diazo-dinitro-hydroquinonic
|
|
| 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.
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
|
|
|
Thraxx
Hazard to Self
Posts: 71
Registered: 15-10-2016
Member Is Offline
Mood: No Mood
|
|
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]
|
|
|
PHILOU Zrealone
International Hazard
Posts: 2893
Registered: 20-5-2002
Location: Brussel
Member Is Offline
Mood: Bis-diazo-dinitro-hydroquinonic
|
|
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]
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
