Furazans and furoxans

[Hex]

There seems to be a bit of interest in these compounds (see the MEDINA thread) although I guess they're probably not the most practical target for a garden shed experimentalist. There's a good paper in this years ICT conference on these materials (33rd ICT Conf. on Energetic Materials, 115(1-12), 2002) I suspect that the material discussed in the MEDINA thread in 4,4'-dinitro-3,3'-azofuroxan (DNAF, C4N8O8), perfect oxygen balance and vod of 10k/s. [O-][N+]1=C(\N=N/C2=[N+]([O-])ON=C2[N+]([O-])=O)C([N+]([O-])=O)=NO1 is the SMILES string for anyone who's got ChemWindow or similar. It begins to decompose at around 110 though, so it's probably not going to find any practical uses. The 4-4' diamino analogue isn't quite so powerful, but is a lot more stable. I've got a fair amount of material on these (too much to be arsed to type up and post), so if there's any specific questions....

[simply RED]

Is it really the most powerful explosive?
Which are other pretendents for explosive N1?

[hedm]

check <a href="http://www.pirotechnika.one.pl/hedm/DNAF.doc" target="_blank">http://www.pirotechnika.one.pl/hedm/DNAF.doc</a> to see structure of dinitroazofuroxan

[Alchemist]

Hello all,

just uploaded "new_energetic_materials" and "new_explosives" to the ftp.

There is some information on the above plus more!

[Mr Cool]

Hehe, DNAF looks fun! I bet it's a pain in the arse to make though (aren't all the good things?!).

Hmmm... question: what do you guys think about p-dichlorobenzene + NH3 --&gt; p-diaminobenzene, + HNO3 + H2SO4 --&gt; 1,4-diamino-2,3,5,6-tetranitrobenzene, + HN3 --&gt; 1,4-diaminobenzodifuroxan (and before some smart-arse points it out, I know that's not balanced...)?
The tetranitro- compound might very well be more powerful, but a hell of a lot more sensitive (fun though!). Do you think the difuroxan will even be detonatable without a booster? What about oxidising the amines to nitros, I've heard of alkaline KMnO4 being used to do that in some compounds. Then you'd have the same fuel/oxygen ratio as TeNB, and more gas.
Input? Have I just got carried away with a silly idea?

[simply RED]

I can;t download or see the files(new energetic mathereals and new explosives). It gives me permission denied.. :(
How to access these files?

[hedm]

there are 2 links:
<a href="http://www.pirotechnika.one.pl/hedm/explosives/new_energetic_materials.pdf" target="_blank">http://www.pirotechnika.one.pl/hedm/explosives/new_energetic_materials.pdf</a>
and
<a href="http://www.pirotechnika.one.pl/hedm/explosives/new_explosives.pdf" target="_blank">http://www.pirotechnika.one.pl/hedm/explosives/new_explosives.pdf</a>

(there is some information about thermally resistant explosives also)

hedm

[Hex]

Mr. C,
Probably a few problems with that - reckon you'd have problems trying to nitrate 1,4-diamino benzene directly, it's just too easily oxidised. Maybe nitrate first, aminate later, I don't know...you can see a synthesis for monoazido-pentanitrobenzene in US Pat 4600536, I haven't read it myself, but I guess it may have a few useful suggestions

[Mr Cool]

Eidt: sorry, stoopid mistake.

Anyways, I'll check out that patent, thanks.

<small>[ September 11, 2002, 12:50 PM: Message edited by: Mr Cool ]</small>

[Hystrix]

AFAIK linear benzodifuroxan compounds were not synthesized, their precursors (for example, 5-azido-6-nitro-benzofuroxan) decay in reaction conditions. By the way, dinitrofuroxan (DNFX) can be obtained by glyoxime nitration with 25% HNO3 in Et2O and cyclization with N2O5/CCl4. Summary yield of DNFX (calc. to glyoxime) is about 40%. DNFX is thermally unstable, it can be treated with NH3/CH2Cl2 at -20 degrees C. to form 3-nitro-4-aminofuroxan. I think this aminonitrofuroxan is precursor for said 4,4'-dinitro-3,3'-azofuroxan.

[fluoroantimonic]

This is the only thread i can find on this subject so I'll post it here.

I don't know if it is common knowledge or not, but Axt successfully synthesized DNAF along with AAAF almost from scratch in 2006. I have found where Microtek started the process but apparently stopped, other than that, nothing. I hope I UDTFSE to its full potential..

https://sciencemadness.org/talk/viewthread.php?tid=5813

It has a great many steps and each one has an average yield of 50% or so, so the total yield is terrible. But hey, it should be worth it for an explosive as ungodly as this!

I did a little calculating, the required raw materials to produce 220 grams of DNAF (or 420g DAAF if you stop there):

2.5 kg glyoxal
18 kg nitromethane
34 kg 32% HCl
8 kg NaOH
800g KOH
8.8 kg 50% H2O2
9.4 kg 98% H2SO4
5 kg ammonium persulfate
A shitload of time and money

That includes just about everything required but water and a few solvents for recrystallization, etc.

I think by far hardest to get of those ingredients is the nitromethane and the glyoxal, I'm not sure how they could be procured. There are alternative ways to both hydroxylammonium chloride and glyoxal, but all require much more design work.

Both the electrolysis of HNO3 and the hydrogenation of HNO2 possibly look like promising methods for hydroxylammonium chloride. Another plus is hydroxylammonium chloride can be used to easily produce nitrous oxide.

Oxidation of plain old ethylene glycol via copper catalyst at 650*C with air and water looks easy enough and has high yields of glyoxal with only a percent or two of other aldehydes contaminating it.

Someday, I will do this, maybe even larger scale... someday when I have the money. God, what would I do with 220 grams of 9800 m/s castable kick ass? Sure it might be far more effort than an equivalent amount of PETN or RDX but who cares? That much velocity is worth it in my opinion. And people say its too unstable, but to me 8 cm of a 2.5 kg weight is enough safety, after all it doesn't have to withstand small arms fire or anything. A large shaped charge with cast DNAF would be mind blowing.

[Emil]

Comparing the extra power this explosive creates, against the complexity (in all areas) of it's synthesis, to me is completely unbalancing.

Ok fair enough it has an extra 1000 or so m/s detonation velocity, but the amount of chemicals needed to synthesise just over 200g's of the stuff is bad waste. Lets be honest here, the extra damage you are going to create with a charge of this size, compared to the extra graft and money needed to be put in isn't worth it. 18kg of Nitromethane? 34kg of HCL??

Those alone are going to be expensive enough, not to mention you are doing this for only 200g of product! If you ever have this amount of disposable income at your hands then I'd say go for it, otherwise, open your eyes!

You have to love these tropical materials though. it's just a shame that the home experimenter will never be able to afford something like this on a regular scale.

[fluoroantimonic]

Of course its not practical, but since when has that stopped anyone? If I wanted cost effectiveness I'd just use a bunch of ANNM or maybe ETN. Its about being one of the very few people that has synthesized it outside of a professional lab, not to mention having a lack of any formal education above highschool. And being able to say you synthesized one of the most powerful usable explosives ever discovered. I think that might be worth the few hundred or maybe thousand dollars required. Of course I don't have that kind of money right now, but it the not too distant future I hope I will. And I don't have any other expensive hobbies, so much of my disposable income will probably go to chemistry/explosives. Also the is so much left to be desired from the synthesis (a decent yield) that it leaves a lot of room for improvement, and if I can get the chance to contribute to that even just a tiny bit, it would surely be worth the money. Just my opinion.

On another note, does anyone know anything about hydroxylamine picrate or 3,4 Diaminofurazan picrate? Just curios mostly. I'm sure there are plenty of other energetic ions one could attach to either. Azides might be interesting.

[Charles Owlen Picket]

High level, quality newer materials like MEDINA, etc are actually not noticed at the gram and ounce level..... Believe me; the weight needs to be in the 2-5 lbs range & in direct comparison to and equal amount of a standard similar (such as RDX) before one can watch an experiment somewhere in the woods or whatever and say "that's a superior material"!
There are people who have wasted a lot of time and money in experiments on a ounce level who have learned this lesson.

[Microtek]

That certainly depends on what kind of experiments you are going to perform. In my experience you can easily see the difference in plate dent and in the amount of spall when detonating 0.5 g charges of sensitive secondaries in contact with a witness plate.
If you simply put the charge into the ground and want to see what makes the bigger boom, then I quite agree with you.