Tris(nitromethyl)amin, The Way from NTA

[Abigail]

An interesting compound is tris(nitromethyl)amine and the simple way from NTA (nitrilotriacetic acid, N(CH2-COOH)3 ) and HNO3. I think that's a quite good idea, somewhat dangerous but I believe that is correct. The synthesis will produce some
nitrogen oxides and you need somewhat more HNO3.

Tris(nitromethyl)amine (TNMA):


Prepare a mixture of 100 ml 35% HNO3 in a 1000 ml beaker, place the beaker in a salt/ice bad and 15 g of powdered NTA is stirred in small portions to the HNO3.

Place the flask to a stirrer and the mixture is stirred over a period of 30 minutes. The temperatureshould not rise above 40°C!

Drop 27 ml of 96% H2SO4 to the mixture, 56 ml of 70% HNO3 is added in around 10 ml portions over 60 minutes, another 66 ml of 96% H2SO4 is dropped in and the mixture is stirred for several minutes. The reaction is complete when no nitrogen oxides will bubble off.

Cool the mixture, 100 ml of 99% H2SO4 is dropped in and the flask is standing for any time.

(I`m not sure but I believe TNMA is a liquid and a synthesis with concetrated HNO3 is sufficient.)

When the TNMA will not form a layer, the liquid is extracted with several portions of methylene chloride and anhydrous magnesium sulfate, the magnesium sulfate is removed by filtering and the methylene chloride and water is expelled on an evaporating pan.

The remainders of acid are removed by washing the liquid with with 5% sodium carbonate solution and dried over sodium chloride.


Seems possible, does anyone think that is correct ?

[nbk2000]

Where did you get this process from?

A source is required to determine validity.

If you made it up yourself, what's your basis for doing so?

[atlas#11]

This sounds like a pretty good compound to me, the synthesis seems like it would work. Perhaps thers a way to get nitrillotriacetic acid from detergent? Probably in small quantities, no where near practical as a source. 100g is avalible from alfa aesar at about 16 bucks.

1,3,5-(NO2)3-2-(N3)-C6H2, tnma is a nitrophenyl azide. Am I looking for the right compound?

"Even the weakest of the investigated organic explosives (TNMA) is more powerful than AgN3 or Pb(N3)2, if the acoustic level is interpret as somewhat proportional to the detonation power."

Sounds like its abit more work than I'm willing to put into something that "sounds" more powerful than silver azide. Have you any experience with this compound? It sounds neat, as do dnta and tnta, but I don't want to mess with carconogens when I can make silver acetyelide in about fifteen minutes and be happy with it. Also, where did you get this procedure? Google only gives me a few pdf's on specrto analysis and such of the compound.

[nbk2000]

It sounds neat, as do dnta and tnta,...


Acronyms should always be CAPITALIZED to make them stand out.

Observe:


It sounds neat, as do DNTA and TNTA,...


Further errors:


Perhaps thers a way to get nitrillotriacetic acid from detergent?


Shouldn't that be:


Perhaps there's a way to get nitrilotriacetic acid from detergent?


Grammar is important when you're dealing with technical subject matter that can KILL YOU!

You start getting sloppy with the little things and you'll end up as sloppy little things all over the floor, walls, and ceiling. :)

For instance, what the hell does this mean?


When the TNMA will not form a layer,


Does that mean IN CASE the TNMA does NOT seperate into a distinct layer, that you extract it?

Or does it mean that it NEVER forms a seperate layer, requiring extraction?

[The_Duke]

On first glance, the procedure posted above will not lead to the desired compound nor will it even form a nitro compound… The (COOH) group will not be completely cleaved and the carboxyl group will most likely remain intact (as I don't see decarboxylation being likely to happen), therefore only a nitrate ester (Tris(carboxymethyl)amine trinitrate?) seems possible with this rxn. This procedure could even prove dangerous so be carfull.

[nbk2000]

I'm still waiting on either citation of source, or claim of originality.

Even more importantly, what is this used for? Google doesn't find it.

Is it an explosive, propellant, chemical weapon, or precursor for any of the former?

[Abigail]

Oh, i meant it is not known if the TNMA will form a separate layer. I`ve never made it but i would guess there are only two possibilities to obtain this compound. I don`t want give insufficient suggestions or something like crap. Why should i need a validity to bring up some nice stuff to the forum ?
I would not recommend the process with three substituents of concentrated HNO3/H2SO4 and a carboxylic acid, you want to destroy it ?
By the way, i would not trust what google told. I could not found anywhat about this.
I will thinking some days, a useful process to make NTA seems interested. You can get NTA from most of the chem suppliers, somewhat expensive - around $170 per pound.

[FUTI]

trinitriloacetic acid is known to decompose in acidic conditions (H2SO4) giving iminodiacetic acid so I guess yuo will have much problems to solve with that one but if it makes you happy go away. Still...no reference of properies of that compound, posible use etc from you Abigail even after NBK asked you. Do you really want to piss us of by forcing us to use SciFinder or what? This is science forum...we chit-chat here about science but you happens to be too misterious.

[nbk2000]

Your next post, Abigail, had better be to state of what use this chemical is, in very clear and concise detail, or it's the end of your existance here.

Posting just any old random chemical synth is pointless. There are other places for such things, like Sciencemadness.

Here, at RS.org, we deal only in those things useful as weapons.

Oh, and I'm getting the distinct impression that the process you posted is something you cooked up yourself, not from any published source. Such 1+1 chemistry results in an immediate banning.

[Alexires]

Abigail - You have answered your own question.

Why would one need to validate a sythesis for an unknown chemical on an Explosives and Weapons forum?

Let's see.

If your sythesis is shit, we die.

If the product is an evaporated chemical weapon, we die.

Hell, it might just be some combination of chemicals that no one has ever mixed together before and forms an increadibly powerful and sensitive explosive that we will be the last to see (until some other idiot tries it) and we die.

What the hell is it, what the hell does it do, and why the hell should I trust your "synthesis"?

[megalomania]

This sounds like a novel high explosive compound of little importance if indeed that synthesis is correct. Owing to the simplicity of that reaction, tris(nitromethyl)amine would have been around for awhile. It is not unprecedented that a nitro group can replace a carboxyl group. I could not spare the time today, but I will run a scifinder search to satisfy my curiosity on Wednesday.

[megalomania]

The compound in question is more properly named 1-nitro-N,N-bis(nitromethyl)-methanamine using IUPAC nomenclature, not that swissified version you used, which I gather is part of the problem in finding out what this stuff is. The CAS# is 60583-48-4. It is indeed an explosive, and it is of little known value. SciFinder lists but one reference, a Japanese patent that uses 1-nitro-N,N-bis(nitromethyl)-methanamine in admixture with a few other explosives. Since there are no preparation references, I gather this is an old one, as in one must use Belstein to locate its 19th century origins.

Owing to the fact there has been but one blip on the radar in over 50 years, it is apparent both industry and the military have abandoned it utterly and completely. Attached is the molecular structure for everyone’s edification.