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Author: Subject: Nitration of Tris????
chemoleo
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[*] posted on 28-8-2003 at 18:18
Nitration of Tris????


Ok, silly question
Its quite easy to get hold of Tris buffer as a solid, which is (HOCH2)3CNH2, so similar to pentaerythritol except one methoxy group substituted with NH2.
Thus I wondered -- would there be any point in nitrating this? theoretically one would obtain the trinitrate, and the nitrate salt of this. surely though, the amine group would get oxidised ?!? Anyway, the point is, do you think its worth trying this? what happens to tertiary amines upon nitration?
If theory holds (which I doubt), I reckon this should make quite an interesting energetic compound :)
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[*] posted on 28-8-2003 at 18:35


cool!!!

yeah!!!!!




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chemoleo
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[*] posted on 28-8-2003 at 18:45


hehe .... ur enthusiasm is appreciated :)
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Blind Angel
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[*] posted on 28-8-2003 at 19:12


Will it make (O<sub>2</sub>NOCH<sub>2</sub>;)<sub>3</sub>CNH<sub>2</sub> or (O<sub>2</sub>NCH<sub>2</sub>;)<sub>3</sub>CNH<sub>2</sub> ?



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chemoleo
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[*] posted on 28-8-2003 at 19:18


ok, assuming that the NH2 group doesnt get oxidised/whatever, you should get (just like NG/PETN/ETN) [(O2NOCH2)3CNH3]+ [NO3]- i.e. the nitrate salt of the nitrated version of Tris.

btw blindangel how do u do the subscript?
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[*] posted on 28-8-2003 at 19:28


< sub > xxxx < /sub >
Withouth the space




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[*] posted on 29-8-2003 at 03:58


<sub>awesome</sub>awesome!



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[*] posted on 29-8-2003 at 06:26


i have a PDF somehwere where it describes the nitration of urea to nitrourea with mixed acids.(whee)

i would think that it wouldnt oxidise real easily.

where is this stuff available?




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chemoleo
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[*] posted on 29-8-2003 at 06:34


'that stuff' is one of the most commonly used buffers anywhere... next to phosphate buffer maybe. So I imagine any lab will have it, and ordering it via someone who works in a lab won't ever raise eyebrows. I dont know whether you can get it as a household item or whatever - personally there is no need for it for me as I happen to get hold of it easily out of a lab...
I guess any chemistry supplier/pharmacy will have it, in bulk.
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[*] posted on 29-8-2003 at 07:04


Given that it's not easy to acquire pentaerythritol (in the UK, anyway), and one of the precursors, acetaldehyde, is a watched chemical, is it possible to prepare pentaerythritol from this Tris stuff? If the only difference is that one has an amine and the other a methoxy group, can't you 'swap the amine for a methoxy'? (over simplification, I know, but you get the idea). Maybe with formic acid or something?

Sorry if I am well off base here...it was just a thought.
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[*] posted on 29-8-2003 at 07:23


doubt it will be easy. you are talking of creating a new C-C bond. Also, the remaining CH2OH are fairly reactive themselves, so they would need to be protected to work on the NH2 specifically.
Anyway, thats why I thought Tris-trinitrate might make a nice compound if it works, and possibly a nice replacement for PETN...as it is easy to get hold of Tris
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[*] posted on 29-8-2003 at 07:23


I can't see a way to make it into PE, but that doesn't mean it can't be done...

Shouldn't be too hard to make a kinda nitramine version of NIBGTN, I'm quite sure that if you used the common PETN synth (95% HNO3 etc) that you'd end up with the nitramine rather than the nitrate salt.
C(CH<sub>2</sub>ONO<sub>2</sub>;)<sub>3</sub>NHNO<sub>2</sub>. Good OB...

[Edited on 29-8-2003 by Nick F]
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[*] posted on 29-8-2003 at 07:31


good point.
thats what I tought, too, to nitrate it as with PETN.
wow, that final compound should indeed be quite interesting!
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[*] posted on 29-8-2003 at 09:04


Hey, just think - oxidise it (like ammonia to hydrazine) and then nitrate it to (O<sub>2</sub>NOCH<sub>2</sub>;)<sub>3</sub>C-N(NO<sub>2</sub>;)-N(NO<sub>2</sub>;)-C(CH<sub>2</sub>ONO<sub>2</sub>;)<sub>3</sub>

Probably not possible though...

[Edited on 29-8-2003 by Nick F]




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[*] posted on 29-8-2003 at 16:46


ok I think due to the scarce number of replies someone got to try it....!
i wont in the near future as I am away from my lab.... although i got tons of Tris buffer around me! anyone requires a little sample? :D
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[*] posted on 29-8-2003 at 18:07


lol dont send it to anyone in america because thanks to these new security measures to keep us safe from the evil terrorists, all powder is taken out of the mail... there go my coke shipments



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[*] posted on 1-9-2003 at 07:24


ok, the offer stands nonetheless :)
anyone in the UK who wants to try it with a few grams of Tris?? Its not a regulated substance or anything, so you would most definitely not get into trouble even if the police etc did find it :)
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[*] posted on 1-9-2003 at 10:32


sorry, not as far as I am aware. It is a very common laboratory reagent (especially in biological/biochemical labs), used as a buffer.
It is nontoxic, and not a regulated chemical. Chemical supplies should ship it without questions asked, and I am sure pharmacies would stock it (alternatively you could order it).
The IS name is Tris(hydroxymethyl)aminomethane, or TRIS Buffer.
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[*] posted on 1-9-2003 at 13:45
nitration of triethanolamine


yo, another idea.

Triethanolamine is (HOCH2CH2)3N. So three hydroxyls.
Is it possible to nitrate this, so that
(O2NOCH2CH2)3N is produced??
Anyone tried this?

This time it is truly easy to get hold of triethanolamine, photographics suppliers have this.

PS Thought of making another thread, but dont want to clog it with random nitration ideas :D
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[*] posted on 2-9-2003 at 03:48


hi i doubt it willbe that easy
:P
-------------------------------------

Please refrain from posting crap like this.

[Edited on 2-9-2003 by vulture]
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[*] posted on 3-9-2003 at 17:37


tho my gut feeling says u are right, why exactly wouldnt you get it? I bet, if you were able to make triethanolamine trinitrate, people would be quite impressed by its power!!! :P
the same goes for Tris-trinitrate!

Edit: Oops, didnt see vultures moderating Edit! Still I reckon its a valid question, right?

[Edited on 4-9-2003 by chemoleo]
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[*] posted on 4-9-2003 at 06:40


I don't like people who say stuff just to say something without backing it up.
That's all.

No problems with your question Chemoleo.

BTW, does someone know a character called "froot" from south africa. I still have something to settle with this person.

[Edited on 4-9-2003 by vulture]




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[*] posted on 4-9-2003 at 19:44


yeah, anyway... I am surprised that noone can really say for sure what you'd get if you nitrated Tris - I would have thought this is a standard question for all the chemists out there!
Sure, *probably* one'd get the nitramine or something, but has noone got any definitve data/answers on this??? With today's government-funded research, someone's bound to have tried it! Comeon bring it, i would really like to know! :P

PS sorry if I am too demanding :) but thats written into my genes ;)

[Edited on 8-9-2003 by chemoleo]
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cool.gif posted on 10-9-2003 at 14:07


Quote:

what happens to tertiary amines upon nitration?

tris(methylol)methylamine isn't a tertiary amine. it's not related to the kind of C attached to it but is related to number of carbons attached. it's a primary amine and you can't get its nitramine by adding it to nitric acid. I suggest making its aqueous solution,then adding acetic acid filter the acetate salt then distill, hoping to get it's amide. dissolve the amide in CH2Cl2. add to mixed H2SO4 & HNO3/nitrate salt. separate the upper layer after reaction stops. let the CH2Cl2 evaporate away, to the left crystals add warm water. after hydrolysis, you have tris(nitratomethyl)methylnitramine crystals settling in dilute actic acid. filter. wash with water, let dry.

trinitratoethylamine isn't very powerful (due to its low OB), there are many ester nitrates easier to make while being more powerful.
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[*] posted on 10-9-2003 at 19:17


hmm, good point, sorry. obviously I meant an amine attached to a tertiary carbon atom - is that the correct definition? Anyway - I don't see why an amide would be formed once mixed with with acetic acid.
Also, a nitro-ester would be formed most definitely, not the nitro form. just like with PETN.
You sound like you got this synthesis suggestion from somehwere - where? In other words, is
(O2NOCH2)3CC2H5NH2 a well known substance? it is somewhat different to the one I imagined to obtain from Tris, so bear that in mind (i.e. in terms of low OB)
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