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Author: Subject: A less reviewed explosive with VoD 10km/s
DubaiAmateurRocketry
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[*] posted on 2-1-2016 at 17:11
A less reviewed explosive with VoD 10km/s


I see little information on DNAF on this forum 4,4'-Dinitro-3,3'-diazenofuroxan, AKA (4,4'-DiNitro-3,3'-diAzenoFuroxan)

From past forum posts, i see that there has been little confusion few members here thought this DNAF was synthesized by a notable member in the past Axt, however, the DNAF Axt synthesized was 3,3'-Dinitroazoxyfurazan, and hence the name 3,3'-DiNitroAzoxyFurazan

Link to Axt's DNAF(C4N8O7) synthesis: http://www.sciencemadness.org/talk/viewthread.php?tid=5813

The DNAF Axt synthesized has a high density of over 1.9 and a VoD of 9800, however The DNAF (C4N8O8) this post is about has a claimed density of 2.02 and a detonation velocity of 10km/s.

A short summery of DNAF and its synthesis can be found here on the defense science journal.

Direct download link: http://www.publications.drdo.gov.in/ojs/index.php/dsj/articl...

an abstract of the original paper reporting the synthesis of DNAF is here, however I am not sure how to get it, if anyone can find it that'd be great.

http://www.maik.ru/contents/danchem/danchem4-6_98v359cont.ht...

[Edited on 3-1-2016 by DubaiAmateurRocketry]
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[*] posted on 2-1-2016 at 17:38


It is my first time to know about this EM. Thx a lot.

will this link help you : Link
I am thinking to prepare it but I think it is a bit sensitive.

Did you try it before?


DNAF.png - 144kB

[Edited on 3-1-2016 by ecos]
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[*] posted on 2-1-2016 at 18:18
Did find these though


a patent ( I believe I've seen this posted somewhere )
https://translate.google.com/translate?hl=en&sl=zh-CN&am...

Synthesis of 3-Amino-4-nitrofurazan by an Improved Method , is a chinese paper
www.energetic-materials.org.cn/hnclen/ch/reader/create_pdf


Synthesis of Energetic Furazan Derivatives
https://dspace.iup.edu/bitstream/handle/2069/761/Bryan%20J.%...


Calculation of Thermochemical and Explosive Characteristics of Furoxanes
is also here
http://yadda.icm.edu.pl/baztech/element/bwmeta1.element.bazt...
or here
www.wydawnictwa.ipo.waw.pl/cejem/Number-3-4-2008/Zhukov.pdf




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DubaiAmateurRocketry
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[*] posted on 2-1-2016 at 18:48


Quote: Originally posted by ecos  
It is my first time to know about this EM. Thx a lot.

will this link help you : Link
I am thinking to prepare it but I think it is a bit sensitive.

Did you try it before?

[Edited on 3-1-2016 by ecos]


I have not yet tried synthesizing any of the compounds. Furazans is a very attractive class of energetic materials that I wish I had a hand on to play with, however, college is very busy and distracting hehe.

If you ever try synthesizing sensitive compounds such as DNAF, be sure to take a lot of precaution and in very low quantity.

[Edited on 3-1-2016 by DubaiAmateurRocketry]
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[*] posted on 3-1-2016 at 03:29


Unfortunately , I couldn't find any nitromethane in stores in my country :(
I will not be able to synthesis anything :( :'(
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[*] posted on 3-1-2016 at 08:26


Quote: Originally posted by ecos  
Unfortunately , I couldn't find any nitromethane in stores in my country :(
I will not be able to synthesis anything :( :'(


nitromethane should be easy to synthesize and purchase, furthermore, I don't think you have to have nitromethane to synthesize it. If i remember correctly, furazans has more than one method of synthesis and you can possibily start from glyoxime if you can find it.

Quote: Originally posted by franklyn  
a patent ( I believe I've seen this posted somewhere )
https://translate.google.com/translate?hl=en&sl=zh-CN&am...

Synthesis of 3-Amino-4-nitrofurazan by an Improved Method , is a chinese paper
www.energetic-materials.org.cn/hnclen/ch/reader/create_pdf


Synthesis of Energetic Furazan Derivatives
https://dspace.iup.edu/bitstream/handle/2069/761/Bryan%20J.%...


Calculation of Thermochemical and Explosive Characteristics of Furoxanes
is also here
http://yadda.icm.edu.pl/baztech/element/bwmeta1.element.bazt...
or here
www.wydawnictwa.ipo.waw.pl/cejem/Number-3-4-2008/Zhukov.pdf


Thanks a lot for these Franklyn, however I cannot open the Chinese paper you posted.
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[*] posted on 3-1-2016 at 09:35


www.energetic-materials.org.cn/hnclen/ch/reader/create_pdf.a...

www.google.com/#q=Synthesis+of+3-Amino-4-nitrofurazan+by+an+...




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[*] posted on 3-1-2016 at 10:09


Question: DubaiAmateurRocketry was an account shared by several different people in the past. This led to some confusion at times.

Is this still the case, or can we expect that posts under this screen name originate from a single author now and going forward?




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[*] posted on 3-1-2016 at 10:26


Thank you franklyn.

And yes you can assume posts from this account originate from a single author now on. It is still technically shared however the others no longer use this forum.
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[*] posted on 5-1-2016 at 05:51


There is a wikipedia link for it but its accronym is DDF and not DNAF
4,4'-Dinitro-3,3'-diazenofuroxan

It is a perfect OB, aromatic, hydrogen-less molecule...as such it is indeed very powerfull...

[Edited on 5-1-2016 by PHILOU Zrealone]




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[*] posted on 5-1-2016 at 08:19


Quote: Originally posted by DubaiAmateurRocketry  
I see little information on DNAF on this forum 4,4'-Dinitro-3,3'-diazenofuroxan, AKA (4,4'-DiNitro-3,3'-diAzenoFuroxan)

The lack of popularity comes from the great difficulty involved in the manufacture of furoxans in an amateur setting.

Those who are genuinely interested in the chemistry behind these complex molecules soon find there are much safer ways to tinker with advanced areas of chemistry without constantly dealing with intermediates that could kill you at any moment. For all others, there are simpler ways to make powerfully destructive materials with much less time, effort, and expense. Thus, those with the particular tenacity required reach the cutting edge of amateur EM are rare, and as such amateur work on furoxans is very limited.

Kudos are deserved to those who do make these amateur breakthroughs in exotic EMs, but take it from someone in the industry that the experimental EM world is full of pulverized glass and scarred hoods, and is readily disfiguring to those underprepared for the inevitable.




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[*] posted on 10-1-2016 at 07:39


DAR,

The synthesis of 4,4'-dinitro-3,3'-azofuroxan or 4,4'-Dinitro-3,3'-diazenofuroxan (DNAF) is a lengthy multi-step procedure. I've detailed the synthesis of DNAF in the following scheme:

dGPmTQV.png - 17kB

The most important precursor for the synthesis of DNAF is 4-amino-3-azidocarbonylfuroxan (3), synthesized from Diethyl furoxandicarboxylate (2) which in turn can be obtained from Ethyl acetoacetate (1). Procedure on how (2) can be obtained from (1) can be found in reference [1].

Compound (3) can undergo an oxidative coupling in the presence of KMnO4 to generate (4). A Curtius rearrangement is obtained when (4) is heated in Dioxane in the presence of water. This rearrangement led the formation of the corresponding diamino derivative (5) in 69% yield. The final step is the oxidation of the diamino to the corresponding dinitro and this by using harsh condition [2]: 85% concentration of hydrogen peroxide in 96% sulfuric acid all this in the presence of sodium tungstate. The oxidation step as seen in the scheme above is inefficient due to the low yield of this reaction (26%).

As claimed in [2], the detonation velocity and pressure of DNAF (at 1.97 g/cm3) are D= 9.70 km/s, P= 470 kbar. The single crystal density of DNAF is 2.002 g/cm3 (obtained from X-ray diffraction data). At this density the detonation velocity will reach 10 km/s.

DNAF and other furazan/furoxan derivatives were investigated as ingredient in composite propellant formulation, for more information see the attached file below.


References:

[1] Snyder, H. R., & Boyer, N. E. (1955). The Synthesis of Furoxans from Aryl Methyl Ketones and Nitric Acid1. Journal of the American Chemical Society, 77(16), 4233-4238. doi: 10.1021/ja01621a021

[2] Makhova, N. N., & Kulikov, A. S. (2013). Advances in the chemistry of monocyclic amino- and nitrofuroxans. Russian Chemical Reviews, 82(11), 1007.

Dany.

Attachment: Propellants formulations.pdf (284kB)
This file has been downloaded 224 times

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[*] posted on 12-1-2016 at 01:45


Quote: Originally posted by DubaiAmateurRocketry  
Quote: Originally posted by ecos  
Unfortunately , I couldn't find any nitromethane in stores in my country :(
I will not be able to synthesis anything :( :'(


nitromethane should be easy to synthesize and purchase, furthermore, I don't think you have to have nitromethane to synthesize it. If i remember correctly, furazans has more than one method of synthesis and you can possibily start from glyoxime if you can find it.


I would need NM to synthesis Hydroxylamine Hydrochloride!
do you know simple route to synthesis NM ? I think i need to nitrate propane and then filter. This is not a simple task.
NM is not sold in all countries. I also don't know where to get glyoxime !
so sad :(

[Edited on 12-1-2016 by ecos]
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[*] posted on 12-1-2016 at 04:42


Quote: Originally posted by ecos  
Quote: Originally posted by DubaiAmateurRocketry  
Quote: Originally posted by ecos  
Unfortunately , I couldn't find any nitromethane in stores in my country :(
I will not be able to synthesis anything :( :'(


nitromethane should be easy to synthesize and purchase, furthermore, I don't think you have to have nitromethane to synthesize it. If i remember correctly, furazans has more than one method of synthesis and you can possibily start from glyoxime if you can find it.


I would need NM to synthesis Hydroxylamine Hydrochloride!
do you know simple route to synthesis NM ? I think i need to nitrate propane and then filter. This is not a simple task.
NM is not sold in all countries. I also don't know where to get glyoxime !
so sad :(

[Edited on 12-1-2016 by ecos]


https://en.wikipedia.org/wiki/Nitromethane#Laboratory_method...

This is a fairly simple method.

Both starting materials are not exotic and it is a fairly straightforward single step synthesis. Make sure to find out how to clean any side products such as salt out of nitromethane if they are soluble. I have not yet checked and ill look into it later when I get back.
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[*] posted on 13-1-2016 at 02:27


You could also synthesize HO-NH3*HCl directly (NaNO2, sulfite, SO2, hydrochloric acid and acetone) (see OrgSyn: http://www.orgsyn.org/demo.aspx?prep=CV1P0318).

The main problem here would be the practicalities of SO2 production (at least for me, but that is mostly because I would like to start from elemental sulfur). A good small-scale solution might be to generate it from HCl and sulfite.

[Edited on 13-1-2016 by Microtek]
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[*] posted on 13-1-2016 at 05:55


I have performed the orgsyn procedure on a smaller scale with good results. SO2 is easy to generate; just add acid to a sulfite, bisulfite, or metabisulfite salt. The main drawback is that this prep requires bucket-sized labware for small amounts of hydroxylamine, something like 20g per liter of reaction space.

I also tried modifying the procedure to use metabisulfite rather than bisulfite since metabisulfite acts like bisulfite + SO2 in solution, and I thought maybe the SO2 addition step could be skipped this way. However, there was no product at the end, so I resulted in bubbling SO2 for a few hours.

The procedure is a pain in the ass, but unless you can get your hands on chloroacetic acid, it's the next best thing.




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[*] posted on 13-1-2016 at 13:35


Nitromethane has been discussed many times into the forum.
I would go for known processes:
CH3-I or CH3-Br in DMF with AgNO2 or LiNO2/urea (NaNO2) in aceton.
Heating over 200°C and below 400°C of exces butane, propane or even better ethane bubbled into 69% HNO3 with condensation of nitromethane.

Or new unexplored ones:
Maybe heating of an exces acetic acid or acetonitrile with concentrated HNO3...the resulting nitrated compounds should decarboxylate.

Maybe heating of 1,1,1-trichlorethane with HNO3 and basic hydrolysis.

Maybe nitration of malonic acid or ester...and di-decarboxylation.


For Hydroxylamine there is also reduction of NaNO2 with Zn and aceton see into the reference section requested documents 9 by PHILOU Zrealone

The document is given by solo a little above my post into the link...


[Edited on 13-1-2016 by PHILOU Zrealone]




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