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Author: Subject: 5-ATZ(5-Aminotetrazole), the nitrotetrazolate ion and friends
Rosco Bodine
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[*] posted on 8-10-2013 at 18:09


Azole-Based Energetic Salts, Chemical Reviews, Gao and Shreeve

Attachment: Azole-Based Energetic Salts, Chemical Reviews.pdf (1.6MB)
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Boffis
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[*] posted on 9-10-2013 at 09:30


@ Rosco I posted this reference a year ago and picked out a few do-able syntheses in it but it didn't stir up any meaningful response. Its a great reference, full of data and interesting ideas but some of the statements about methods of synthesis are wrong and you need to refer to the original papers (many of which I have requested through the references section).

Hope you get a better response!
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Rosco Bodine
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[*] posted on 9-10-2013 at 17:46


@Boffis, are you talking about your post in another thread?
http://www.sciencemadness.org/talk/viewthread.php?tid=21743&...
I missed it but above is the article, since the reference was posted,
Dany sent me a link for the article, and then I reduced the file size enough for it to attach.

You were experimenting with the dicyandiamide, aka cyanoguanidine, so I thought the summary of interesting copper compounds I posted last week
http://www.sciencemadness.org/talk/viewthread.php?tid=8144&a...
may rouse your curiosity, with regards to the guanazole synthesis involving cyanoguanidine being boiled with hydrazine dihydrochloride. Given that in my improved hydrazine sulfate synthesis using pool hypochlorite and urea, there are modifications possible where the end product desired is not hydrazine sulfate, it had occurred to me that a modification might be chosen such as formation of methyl ethyl ketone azine, separating and hydrolyzing the azine with hydrochloric acid, and distilling off the MEK, leaving hydrazine dihydrochloride for use as a precursor for boiling with cyanoguanidine where the ultimate end product would be guanazole. It could of course also be possible to first obtain the hydrazine sulfate in the usual way and convert it to the hydrazine dihydrochloride using calcium chloride, filtering out the sulfate value and concentrating the filtrate in preparation for reaction with the cyanoguanidine.

Thereafter, the guanazole would be nitrosated by one method to the dinitrotriazole, or the nitrosation under Sandmeyer condition would provide the mixed result where half the product is dinitrotriazole and half the product is nitrotetrazole.

Cyanoguanidine is actually a slow time release nitrogen fertilizer which is sold as 66-0-0 and is stocked in 25kg bags but it is an obscure product probably not widely used or commonly found stocked because it is an expensive specialty product and special order ag product for professionals. One brand name is Guardian-DF for the cyanoguanidine crystals.
A bag of the stuff could set a golf course landscaper back a couple of hundred bucks easily, but hey golf is important :D

[Edited on 10-10-2013 by Rosco Bodine]
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[*] posted on 13-10-2013 at 22:42


http://www.youtube.com/watch?v=wu9Y1OCXXO0

Here's a vid of some of the NaCuNTZ i made. I think its behaviour in a detonator is the same as lead-azide. Difficult to detonate from a single spark. Since I have no visco at the moment I cant test a det with visco; only with a straw filled with blackpowder (but i cant get detonation, only some crackling.
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Rosco Bodine
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[*] posted on 17-10-2013 at 11:24


Here are a couple of additional articles. These look familiar so they may have been posted before, but I haven't found where so here they are.



Attachment: Insensitive high-performance replacements for RDX, Klapotke ADA466070[1].pdf (926kB)
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Attachment: Green Pyrotechnics, A Chemists Challenge, Klapotke.pdf (842kB)
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[Edited on 17-10-2013 by Rosco Bodine]
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DubaiAmateurRocketry
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[*] posted on 21-10-2013 at 07:45


Just curious, what is the toxicity or LD50 of tetrazole compounds ?

5 aminotetrazole for example ?




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DubaiAmateurRocketry
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[*] posted on 24-10-2013 at 12:27


Quote: Originally posted by Axt  
Nitrosation of diaminotetrazole. There was only five (prepared and isolated) structures in the scifinder database that had a string of 7 nitrogens, at least that I could see. Of which only two looked notably energetic, this being one and <a href="http://www.sciencemadness.org/talk/viewthread.php?tid=10555">this</a> the other.

Personally I wouldn't have a problem heating a small amout of Pb azide dispersed in a solvent to 100°C, unless it wanted to bump and splutter but that shouldn't be a problem with DMF. Patent SE154979 precipitates Pb(N3)2 from Pb(NO3)2 + NaN3 at 90°C, a more extreme example is US3345130 which precipitates it from molten KNO3/NaNO3 at 225°C!! (Pb(N3)2's decomposition temp is >300°C).

[Edited on 13-6-2008 by Axt]


It is possible to hang a nitro group there ?




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snooby
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[*] posted on 31-10-2013 at 12:34


We all know that a very important substance is Sodiumnitrotetrazole or NaNTZ! We can all make this easily from the acid salt of cuppernitrotetrazole. Just neutralize it with NaOH and distinguish the CuO leaves u a yellow solution of NaNTZ! Put a CuNO3 solution in it to get the NaCuNTZ....

But this is not the case. The obtained product (see my video http://www.youtube.com/watch?v=wu9Y1OCXXO0 ) is NOT suitable for using in detonators! It wont detonate simply by fuse! After reading a lot, I discoverd that this so called 'raw solution' of NaNTZ must be purificied. This can be done by evaporating the raw NanTZ solution and then extract the pure NaNTZ. BUT this proces is dangerous. After NaNTZ recrystalize from aceton it easily forms anhydrous NaNTZ wich is very very dangerous. There are some case where the stuff exploded without reason....

So, my idea: Slowly evaporate your raw NaNTZ solution, wich will give you the monohydrate of NaNTZ and some contamination. Then extract the NaNTZ with an excess of hot aceton. Instead of evaporating the stuf just pour it in distilled water. Then boil the water until the aceton is removed. Now you have the pure solution
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Davin
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[*] posted on 31-10-2013 at 17:34


Quote: Originally posted by snooby  


After NaNTZ recrystalize from aceton it easily forms anhydrous NaNTZ wich is very very dangerous. There are some case where the stuff exploded without reason....



Do you have a reference for this? I have never seen or heard of the the anhydrous coming out of acetone...
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[*] posted on 31-10-2013 at 18:41


Quote: Originally posted by Davin  
Quote: Originally posted by snooby  


After NaNTZ recrystalize from aceton it easily forms anhydrous NaNTZ wich is very very dangerous. There are some case where the stuff exploded without reason....



Do you have a reference for this? I have never seen or heard of the the anhydrous coming out of acetone...


Best reference until now :)

http://onlinelibrary.wiley.com/doi/10.1002/zaac.201300010/ab...

Dany.
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[*] posted on 31-10-2013 at 20:31


Thanks for the compliment Dany, I do believe that method of NaNT dihydrate synthesis to be the best one out there, with the addition rate and temperature control tuned perfectly to avoid microdetonations prior to the isolation in high yield of perfect crystals of the dihydrate. :D ;)

But what I was wondering about was if there was a NaNT reference somewhere indicating the loss of hydration waters of NaNT during recrystallization from acetone as snooby has mentioned. I have never came across any mention of this, and certainly have not had it occur myself.


snooby: If your NaNT solution is coming out yellow you have a temperature control or pH control issue.

[Edited on 1-11-2013 by Davin]
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[*] posted on 31-10-2013 at 20:43


Davin, i want to take advantage of your presence to see what are the progress in TKX-50? does the team plan to perform in depth studies on this important HEDM like cylinder expansion test? i would like to know how it will perform in metal acceleration ability and if the Dcj prdicted by EXPLO5.05 is realistic. I also would like to know the value of the constant (alpha, beta, kappa and tetha) used in the BKW EOS in EXPLO.05 for performing detonation performance calculation in your articles.

Dany.

[Edited on 1-11-2013 by Dany]
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snooby
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[*] posted on 1-11-2013 at 09:34


And what about my idea of putting the aceton/NaNTZ mix into water and let evaporate the aceton?? Then you avoid the step with working with the pure NaNTZ..?


Engager said......
And one more thing, BE AWARE that separation of NaNT from solution in acetone IS very dangerous, and i know people from sciencemadness forum who taken serious wounds and injuries during this process, when product spontaneously exploded during crystallization. This could be attributed to formation of very hazardous anhydrous salt, but that is not quite clear in conditions then that happened. So you must consider this proces as very dangerous and take appropriate safety measures/precautions. I'm persistently encourage you to leave separation of pure solid compound and use it only in form of pure AQUEOUS solulitons, prepared by separation of Cu salt and reaction with corresponding ammount of sodium hydroxide (and heat/filtering as written). Remember, clever people learn from mistakes of others, stupid learn on their own. Be smart and cautious, and you will be alive long enough and still be in good health to tell about your beautiful chemical adventures



Btw: a solution of NaNTZ SHOULD be yellowish.. right
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[*] posted on 2-11-2013 at 05:43


Okay today i did it again! I made a solution of (so called RAW) NaNTZ out of acid CuNTZ. You can use this solution to make AgNTZ yes, but no, it will not be pure. You can also make NaCuNTZ (the famous primer) from it, just by puting an solution of CuNO3 in some raw NaNTZ solution, boil it, cool it, filter it, done. See the youtube link for the raw NaCuNTZ! It is not suitable for detonators! In the video it looks like it is! But I need to put a flame against it for like 1 second, and that is just too long. In a det, it wont work, all because of the NaNTZ solution whas RAW.

://www.youtube.com/watch?v=wu9Y1OCXXO0

Today I boiled the raw NaNTZ solution on a waterbath, until cristals apeared. This is your NaNTZ, but with a lot of junk in it. I trew hot aceton over it and decanted the aceton, which turned yellowish. Evaporating the aceton can be dangerous because of anhydrous NaNTZ can form (I red this and also Enger confirmed it.) And btw,,, I had an accident with 200 mg, blowing my eardrums.

So after the aceton dissolved the NaNTZ, there still was a lot of undisolved stuff in my glass. This shows that the NaNTZ solution whas deffinitly not pure! All the stuff that doesnt dissolve is not NaNTZ, and this stuff makes the NaCUNTZ not suitable for detonators of course.

So then I putted the aceton into water, and let the aceton evaporate. After there were no signs of aceton I got a yellowish solution of Pure NaNTZ! I tested this and made some NaCUNTZ and AgNTZ with, wich shows clear colores. Its drying right now, and I will post the results of it! I think this is an safe method of making pure NaNTZ solution, amen
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[*] posted on 2-11-2013 at 14:04


Quote: Originally posted by Dany  
I also would like to know the value of the constant (alpha, beta, kappa and tetha) used in the BKW EOS in EXPLO.05 for performing detonation performance calculation in your articles.



version: alpha: beta: kappa:theta
5.03: 0.5:0.176:14.71:6620
5.04: 0.5:0.96:17.56:4950
At home right now and cannot find 5.05 or 6.01 yet. Will let you know.
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[*] posted on 2-11-2013 at 23:30


Davin, i'm very grateful to you for providing me this informations.

So the version 5.03 (i think this is the first version) of EXPLO5 uses the sets of constant of the well known BKWN which is published by M.Suceska. In his paper [1] M.Suceska compared the BKWN output to other well known BKW EOS variant (BKWR, BKWS and BKW TNT/RDX). Suceska found that BKWN give the best overall agreement between the calculated and experimental values of detonation parameters.

[1]M.Suceska, EXPLO5-Computer program for calculation of detonation parameters (in International Conference of ICT Held in Karlsruhe, Federal Republic of Germany on July 3-6, 2001. Energetic Materials: Ignition, Combustion and Detonation)

http://oai.dtic.mil/oai/oai?verb=getRecord&metadataPrefi...

Dany.




[Edited on 3-11-2013 by Dany]
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[*] posted on 4-11-2013 at 05:40


I only have experience with NH4NTZ, but my experience is similar to snoobys.

I made NH4CuNTZ, als well as NH4NiNTZ.

Both perform nicely, stunning - once you get em going ;)

They are both very stubborn to ignite via flame, almost impossible. The only viable setup for me was putting a thermite layer upon the copper salt - the nickel salt failed even with that.


Am I the only guy experiencing this problem?
Does somebody have an opinion on that?
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snooby
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[*] posted on 4-11-2013 at 05:53


@ Gargamel: The NaCUNTZ is very powerfull but not easy to use in detonators indeed! Not flamesensitive enough! Can you please explain which kind of thermite you are using!? And how you use it in a det? Must be a metal cap right?

The silversalt I made with my pure NaNTZ is very flamesensitive but also very impact-sensitive, so I dont want to use the silversalt! Also sent you a PM!

Gargamel: for the best peforming/most flamesensitive NaCUNTZ:

- Reflux the NaNTZ and CuNO3-solution! Or at least boil it. The liquid must get colorless, if not, you added to much CuNO3 for the amount of NANTZ. So dont put to much CuNO3 (its difficult to calculate the amount of NaNTZ in your solution right). Afterwards, cool it and filter it. Then washing with ethanol and water of course.

- Raw NaNTZ solution is not enough, make it pure by evaporate the solution (not to fast).Do this in different steps! So for example portions of 30 ml NaNTZ solution. Then youre sure you dont have to work with more then 1 gram at most. When Crystals appears, put boiling aceton in it. The decant the hot aceton and put it in distilled water. Do this with al your portions. Then boil the solution to evaporate the aceton. Then let the NaNTZ further evaporate leaving you a really pure solution of NaNTZ.

- use distilled water and in the last step, make sure your NaNTZ solution is PH 4

[Edited on 4-11-2013 by snooby]
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Gargamel
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[*] posted on 4-11-2013 at 09:48


Quote:

Can you please explain which kind of thermite you are using!? And how you use it in a det? Must be a metal cap right?


Simple iron oxide stuff. Only with pyro aluminium to make it sensitive. Maybe CuO or Bismuth based stuff would be better, but I don't like it anyway.
BP never worked.

I did not use it in any det, I find it useless. A primary should be fuse sensitive. The green primaries I tested aren't.


This whole thing was interesting for me because I wanted a primary insensitive to friction and ESD. And as far as I read myself through this whole thing, that applies only to the NH4 salts.





edit:
No metal cap, it was just a parallel wound paper tube, 6mm inner diameter, 1mm walls.
Confinement is not the issue here, like with mercury fulminate, HMTD and so on. If it ignites, DDT comes extremely fast, practically immediate. A small crumb maybe a millimeter long made a little crater in my working plate. Superb!
But before it went, I could push it around over the table with the flame of my little torch...

[Edited on 4-11-2013 by Gargamel]
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[*] posted on 4-11-2013 at 11:52


Witch synthesis did you use for your NH4NT? I'm interested in NH4CuNT as well, but I stumble upon the invest of bariumhydroxyde and such for the synth mentioned bij Engager, did you use the direct method with ammonia soln?
I've experience with AgNT, but I find it rather too sensitive to my tasting, its initiating propperties however are unbeatable IMO.

Quote:

Am I the only guy experiencing this problem?


Could it be something with purity of your reagents or purification steps in between synthesis?
I tried NaCuNT a long time ago and it was just like crackling when lit in a pile, in a cap it just didn’t do anything.
I always blamed myself for bad, or no purification of the 5-ATZ, CuNT, and NaNT between synthesis, after that I abandoned further research into it because reliability was a main factor.

Other thing that came to mind was too much energy dissipating thorough the mass before going high order.
I can’t remember if I tried loosely packed NaCuNT but it would need bigger confinement if it didn’t work I thought, raising scrapnell levels.
There is always a grey area around people going public with practical experience with this kind of stuff, even with lots of easy to prepare primairy’s and its synthesis to be found everywhere.

If thermite is a key factor to get it to work I would be very satisfied, giving up AgNT for thermite => NH4CuNT.




Hi,
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[*] posted on 5-11-2013 at 08:12


Today I did some tests on the sensivity of NaCUNTZ. Blows with a hammer were positive, about 25% less sensitive in comparisson with dextrinated lead-azide but friction-tests almost were al negative. This NaCUNTZ is relatively flame-sensitive but not reliable in a detonator.. So, with the positive hammertests, I am sure my NaCUNTZ is the right stuff, however it is yet not suitable in a det.. I think this was the last time I've made NaCUNTZ.. (btw also made the purple Nickel-salt with it, was even worse!).

The AgNTZ however (yellowish Crystals) are interesting for in detonators, but they are quite sensitive. So, then I would rather stay with the Azo-Clathrate from Mr. anonymious then with the AgNTZ.

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Rosco Bodine
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[*] posted on 5-11-2013 at 13:15


Well tickle me tweeters and bump my subwoofers :D
http://www.youtube.com/watch?v=O6kSEqnDoLE

<iframe sandbox width="640" height="480" src="//www.youtube.com/embed/O6kSEqnDoLE?rel=0" frameborder="0" allowfullscreen></iframe>
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DubaiAmateurRocketry
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[*] posted on 7-11-2013 at 11:17


Quote: Originally posted by AndersHoveland  
I think the most promisting energetic compound may be dinitromethyl tetrazole.
“Syntheis of 5-Dinitromethyltetrazole”, A. V. Shastin, B. L. Korsunskii, T. I. Godovikova, V. P. Lodygina. (2009) Russia

The structure of this compound has resemblance to another well-described insensitive energetic compound, diaminodinitroethylene (Fox-7).

Dinitromethyl tetrazole is somewhat acidic and can form salts.

Measurements of the explosive properties of dinitromethyl tetrazole have not been reported, but I think it would have an excellent combination of explosive performance and stability.

The aromatic nature of the ring would stabilize the nitrogen atoms, while the two NH groups be electron-donating toward the geminal nitro groups, stabilizing them. Many energetic tetrazole compounds have lower sensitivities than RDX, and Fox-7, which also contains the gem-dinitro functional group, is roughly twice as resistant to impact as HMX.


[img]http://www.sciencemadness.org/talk/files.php?pid=233635&aid=17226[/img]


This thing is actually interesting. I got the papers down there.

Quote: Originally posted by The_Davster  
http://onlinelibrary.wiley.com/doi/10.1002/prep.200900049/ab...

"Dinitromethyltetrazole and its salts: A comprehensive study"


Paper in the uploads

And in the paper, the Di-ammonium cation of the Dinitromethyltetrazole, is it possible to use the nitronium cation ?

http://onlinelibrary.wiley.com/doi/10.1002/poc.3197/abstract





Attachment: Synthesis of 5-Dinitromethyltetrazole.pdf (235kB)
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[Edited on 7-11-2013 by DubaiAmateurRocketry]

Attachment: phpFvHU8l (744kB)
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Rosco Bodine
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[*] posted on 13-11-2013 at 23:58


Here are some of the aforementioned DBX-1 related references attached along with a related patent

Attachment: Preparation of High Purity Sodium 5-Nitrotetrazolate (NaNT)-An Essential Precursor.pdf (697kB)
This file has been downloaded 894 times

http://www.navsea.navy.mil/nswc/indianhead/TEWPresentations/...

Attachment: DBX-1 A Lead Free Replacement for Lead Azide.pdf (393kB)
This file has been downloaded 1821 times

Attachment: US8440008 Cuprous Nitrotetrazolate - Fronabarger and Williams.pdf (579kB)
This file has been downloaded 964 times

Attachment: Williams-Mike-DBX-1-A_Potential_Drop-In_Replacemen.pdf (1.3MB)
This file has been downloaded 2126 times

Attached also is a google translation of a German patent and on page 12 of the pdf are examples of some other copper complexes of interest

Attachment: Patent DE102010036950A1 - New metal-tetrazole complex useful as initiating e.pdf (155kB)
This file has been downloaded 1152 times

Thanks to Dany and solo for the journal articles

[Edited on 15-11-2013 by Rosco Bodine]
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Rosco Bodine
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[*] posted on 15-11-2013 at 00:40


As was pointed out earlier in the thread there has already been worked out at LANL a method for isolation of 5-nitrotetrazole that is analytically pure

http://www.sciencemadness.org/talk/viewthread.php?tid=8144&a...

The method of Gilligan and Kamlet was patented in US4093623
http://www.sciencemadness.org/talk/viewthread.php?tid=8144&a...

quote: Ammonium nitrotetrazolate was prepared by diazotization of 5-aminotetrazole in the presence of excess nitrite followed by extraction as the tri-laurylamine salt and displacement by ammonia. Upon addition of stoichiometric amount of ammonium hydroxide, sodium nitrotetrazolate forms quantitatively and is analytically pure.

See US7498446 page 4 column 3 line 53 Attached

An idea was described previously for what may be an alternative method for conditions for the Sandmeyer reaction or for adjusting the reaction system thereafter to obtain a more easily filterable crystalline material, which in retrospect
may also be a useful intermediate for DBX-1.
http://www.sciencemadness.org/talk/viewthread.php?tid=8144&a...

It is possible that other low solubility salts of 5-nitrotetrazole may facilitate purification of the nitrotetrazole needed in pure form for successful preparation of cuprous nitrotetrazolate in the desired crystalline form. Or it may be found schemes for precipitating or decomposing the impurities and leaving the purified nitrotetrazole value in solution. Unreacted aminotetrazole impurity may be reduced by improvement of the nitrosation method.

Attachment: US7498446 Primary Explosives of Tetrazole Moiety.pdf (58kB)
This file has been downloaded 599 times

A spontaneous explosion of sodium nitrotetrazole dihydrate during drying has been reported. See page 8 of the attached document.

Attachment: ADA137898.pdf (1.1MB)
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To revisit the earlier aspect of an alternative route for isolation of the nitrotetrazole as a variation on the method of Gilligan and Kamlet see US4552598 attached

Attachment: US4552598 Ethylenediamine salt of 5-nitrotetrazole and preparation.pdf (767kB)
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Further refinement of the process for DBX-1 has been reported by Klapotke and others having parallel research.

Edit: Per request of the inventor presently involved in business negotiations related to the technology, a delay of discussion of some proprietary details of this technology is being effected. Respect for the inventors explains the edits and missing posts in this thread about process details for which discussion can wait awhile yet until the corporate attorneys are satisfied the art originators interests are secured. Putting a lid on this discussion for awhile until given the "all clear" to proceed with further discussion.

Sufficient to say the technology is in part originating from this forum. No more speculation about coincidental discussions and professional publications need be indulged about where the overlap occurs for amateur experimentalism and the formal literature and ongoing current research. For this forum we are already there and have been there awhile.

[Edited on 16-11-2013 by Rosco Bodine]
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