Sciencemadness Discussion Board

TKX-50: A highly powerful explosive with good thermal properties

plante1999 - 4-8-2013 at 03:17

Which program is required to read the file on windows?

Dany - 4-8-2013 at 03:30

TKX-50 is a new, dense high nitrogen high positive enthalpy compounds synthesized by Prof. Thomas Klapotke team in Germany. with detonation performance similar to epsilon CL-20 and thermal stability close to TNT, TKX-50 is a potential candidate for future energetic materials.

Dany

this is a direct link
http://www.chtf.stuba.sk/~szolcsanyi/education/files/Chemia%...

[Edited on 4-8-2013 by Dany]

[Edited on 4-8-2013 by Dany]

Funkerman23 - 4-8-2013 at 03:33

I think he means to view the file you linked to in your post. My computer didn't recognize the file either.

[Edited on 4-8-2013 by Funkerman23]

plante1999 - 4-8-2013 at 03:57

Thanks for fixing the file.

Solomon - 5-8-2013 at 18:38

DDTO is even more powerful than octantirocubane and TKX-50 read about it here: https://sites.google.com/site/ecpreparation/dtto .

Davin - 5-8-2013 at 22:23

DTTO has never been prepared, and the routes towards 1,2,3,4-tetrazine-1,3-dioxides are likely difficult to scale.

TKX50 is easy to scale. Check out this paper
http://pubs.rsc.org/en/Content/ArticleLanding/2012/JM/c2jm33...

Dany - 5-8-2013 at 23:55

Hello Solomon,

DTTO and iso-DTTO are two interesrting energetic molecule. In fact, until today they are debate about the predicted crystallin density of the two molecule. Old reference, predict a crystallin density between 2-2.3 g/cm3. Recent theoretical calculation done by POLITZER et al. (using DFT method) predict a density of about 1.9 g/cm3 for both molecule significally less than 2g/cm3. The predicted detonation velocity and pressure shows that DTTO and iso-DTTO performance is close to epsilon CL-20. what is interesting in DTTO and iso-DTTO is that the two system are less sensitive to impact than HMX and CL-20.

you may be interested in reading the following paper:

http://www.wydawnictwa.ipo.waw.pl/cejem/vol-10-1-2013/Politz...

Solomon - 6-8-2013 at 19:43

Has anyone here ever synthesized TKX50?

Fantasma4500 - 30-9-2013 at 09:06

i doubt that solomon, although axt made glyoxime, and then used it for synthesizing something out from that, which was very powerful, i recall the VoD of being +9000 m/s

correction: axt did make it, i forgot to read everything written.. sorry
(:

[Edited on 30-9-2013 by Antiswat]

AndersHoveland - 30-9-2013 at 23:12

TKX50 has a calculated detonation velocity of 9698 m/s, and has a resistance to impact almost comparable to TNT. TKX-50 not only safer in storage and more thermally stable than HMX, but it has explosive force.

TKX50 consists of two tetrazole rings, forming an anion, and being part of a hydroxylamine salt, with the structure
[-]ON4C-CN4O[-] * 2 NH3OH[+]

While TKX50 was synthesized from oxalohydroximoyl diazide, one wonders if there is another route, perhaps from oxalamidine (oxalamidine is analogous to the oxalic derivative of acetamidine, NH2C(=NH)-C(=NH)NH2 ).

There is plenty of information elsewhere on this, but basically ammonalysis of the oxalamidine with hydrazine hydrate, followed by diazotization with nitrous acid, and then cyclization to the tetrazole in boiling solution. The tetrazole can then be oxidized to the 2N-oxide by either HOF, formed in solution, or, much more practical, by peroxysulfate. I think the tetrazole ring would be able to be oxidized without severing the carbon-carbon bond. Certainly the nitrogens in the tetrazole ring are very electron-withdrawing. This in fact has a charge-shielding effect on 5-methyltetrazole, such that it cannot be directly nitrated (on the methyl group). However, this may likely form an isomer of TKX50. In TKX50, the oxygens are on nitrogen atoms adjacent to the carbon atom, but when, for example, 5-nitrotetrazole is oxidized, nitroetrazole-2-oxide is formed, with the oxygen atom on a nitrogen atom further away from the carbon.

oxalohydroximoyl diazide was synthesized from oxalohydroximoyl dichloride and NaN3. oxalohydroximoyl dichloride has the structure HON=CCl-CCl=NOH

I would be very careful with this, since phosgene oxime, Cl2C=NOH, is known to be a very toxic nettle agent.

not sure how one would go about preparing it, but if its chemistry is anything like phosgene oxime, I am assuming it would start from 1,2-nitroethane (itself formed by exposure of C2H4 with NO2 in the absence of air), next chlorination with hypochlorite solution, then finally reduction with Sn+HCl. Again, do not attempt this without the proper safety precautions, skin exposure could possibly be deadly, much less inhalation.

I have presented a short overview of possible synthesis routes, but this is very complicated, and do not have time to go into details in such a short post. All of this has already been discussed in other places in this forum, however.

[Edited on 1-10-2013 by AndersHoveland]

Davin - 31-10-2013 at 20:43

Quote: Originally posted by AndersHoveland  


oxalohydroximoyl diazide was synthesized from oxalohydroximoyl dichloride and NaN3. oxalohydroximoyl dichloride has the structure HON=CCl-CCl=NOH
...

not sure how one would go about preparing it,


glyoxime and chlorine.

DubaiAmateurRocketry - 17-11-2013 at 11:35

Quote: Originally posted by Davin  
DTTO has never been prepared, and the routes towards 1,2,3,4-tetrazine-1,3-dioxides are likely difficult to scale.

TKX50 is easy to scale. Check out this paper
http://pubs.rsc.org/en/Content/ArticleLanding/2012/JM/c2jm33...


Quote: Originally posted by Dany  
Hello Solomon,

DTTO and iso-DTTO are two interesrting energetic molecule. In fact, until today they are debate about the predicted crystallin density of the two molecule. Old reference, predict a crystallin density between 2-2.3 g/cm3. Recent theoretical calculation done by POLITZER et al. (using DFT method) predict a density of about 1.9 g/cm3 for both molecule significally less than 2g/cm3. The predicted detonation velocity and pressure shows that DTTO and iso-DTTO performance is close to epsilon CL-20. what is interesting in DTTO and iso-DTTO is that the two system are less sensitive to impact than HMX and CL-20.

you may be interested in reading the following paper:

http://www.wydawnictwa.ipo.waw.pl/cejem/vol-10-1-2013/Politz...


Inspired by some similar reactions I saw today, I wonder if these are possible.



The question mark should be N,N-dibromo-2-methyl-propan-2-amine Maybe ? and something else ... that could make the NO2 with NO ? never learned about that.

I think DTTN might need the C=C backbone from the beginning, I do think the 2nd reaction of the upper reaction would work. Using triazene then changing it to tetrazine might be too hard or impossible.



What are your thoughts ?


[Edited on 17-11-2013 by DubaiAmateurRocketry]

Davin - 17-11-2013 at 12:06

Quote: Originally posted by DubaiAmateurRocketry  

Inspired by some similar reactions I saw today, I wonder if these are possible.




Oh how I wish. So many lost weeks trying to get a tBu azoxy on FOX7.... Eventually I just gave up.

Dany - 17-11-2013 at 12:16

Old theoretical study mention that DTTO and iso-DTTO possess high detonation performance (Dcj> 10 km/s & Pcj> 50 GPa). However, as you saw in the POLITZER paper (http://www.wydawnictwa.ipo.waw.pl/cejem/vol-10-1-2013/Politz...) the the newly recalculated properties of the aftermentioned compound is somewhat disappointing. the crystal density of DTTO and iso-DTTO is similar to HMX (1.90 g/cm3) and a Dcj= 9.70-9.71, Pcj= 431-432 kbar. CL-20 is superior to these molecule in term of density and Pcj. with these properties it is better to find other HEDM molecules that can be superior to CL-20 or at least be equal. TKX-50 is one of these rare synthesized molecule that possess high detonation performance with reduced sensitivity (close to TNT sensitivity).

Dany.

DubaiAmateurRocketry - 17-11-2013 at 12:36

Quote: Originally posted by Dany  
Old theoretical study mention that DTTO and iso-DTTO possess high detonation performance (Dcj> 10 km/s & Pcj> 50 GPa). However, as you saw in the POLITZER paper (http://www.wydawnictwa.ipo.waw.pl/cejem/vol-10-1-2013/Politz...) the the newly recalculated properties of the aftermentioned compound is somewhat disappointing. the crystal density of DTTO and iso-DTTO is similar to HMX (1.90 g/cm3) and a Dcj= 9.70-9.71, Pcj= 431-432 kbar. CL-20 is superior to these molecule in term of density and Pcj. with these properties it is better to find other HEDM molecules that can be superior to CL-20 or at least be equal. TKX-50 is one of these rare synthesized molecule that possess high detonation performance with reduced sensitivity (close to TNT sensitivity).

Dany.


DTTO also have very high VOD, 9700 is not that bad. any ways i hope dtto could be made and its density somehow becomes the 2nd exception of that equation :)

can the oxygen stablizing dtto be applied to tetrazoles ?

[Edited on 17-11-2013 by DubaiAmateurRocketry]

Dany - 17-11-2013 at 12:44

Detonation velocity should not be taken alone as an indicative of the power of an explosive materials for more information see:

http://www.sciencemadness.org/talk/viewthread.php?tid=25538&...

Dany.

Davin - 17-11-2013 at 13:44

Quote: Originally posted by DubaiAmateurRocketry  


can the oxygen stablizing dtto be applied to tetrazoles ?


Thermally: no
Impact and friction:yes

http://onlinelibrary.wiley.com/doi/10.1002/chem.201102064/ab...

Dany - 17-11-2013 at 14:19

One crazy idea is to make the azoxy derivative of the famous, very sensitive 1,1′-Azobis(tetrazole). This molecule with a rare N10 chain deserve a thread in the future.

http://pubs.acs.org/doi/abs/10.1021/ic200071q

Dany.



[Edited on 17-11-2013 by Dany]

DubaiAmateurRocketry - 18-11-2013 at 03:26

Quote: Originally posted by Davin  

Oh how I wish. So many lost weeks trying to get a tBu azoxy on FOX7.... Eventually I just gave up.


what about going to the nitrosonium version first ?

http://www.sciencemadness.org/talk/viewthread.php?tid=27329

[Edited on 18-11-2013 by DubaiAmateurRocketry]

[Edited on 18-11-2013 by DubaiAmateurRocketry]

DubaiAmateurRocketry - 20-11-2013 at 11:51

Any ways back to TKX-50, Is it still possible to doubble protonate the tetrazole n oxide and make salts out of it ? like 5 amino tetrazolium n oxide nitrate ?
Quote: Originally posted by Dany  
One crazy idea is to make the azoxy derivative of the famous, very sensitive 1,1′-Azobis(tetrazole). This molecule with a rare N10 chain deserve a thread in the future.

http://pubs.acs.org/doi/abs/10.1021/ic200071q

Dany.



[Edited on 17-11-2013 by Dany]


what about adding N oxide to the azobistetrazole

[Edited on 21-11-2013 by DubaiAmateurRocketry]

Mr.Greeenix - 8-9-2015 at 11:57

here is the patent for TKX50

https://www.google.com.ar/patents/CA2839188A1?cl=en&hl=d...