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chemoleo
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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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Madog
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cool!!!
yeah!!!!!
Most people outgrow their pyro tendencies, we are the ones who\'s tendencies outgrew us.
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chemoleo
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hehe .... ur enthusiasm is appreciated
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Blind Angel
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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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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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Blind Angel
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< sub > xxxx < /sub >
Withouth the space
/}/_//|//) /-\\/|//¬/=/_
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Basement Chemist
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<sub>awesome</sub>awesome!
I am curently hiding from the DEA...
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Madog
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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?
Most people outgrow their pyro tendencies, we are the ones who\'s tendencies outgrew us.
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chemoleo
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'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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AngelEyes
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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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chemoleo
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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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Nick F
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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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chemoleo
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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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Nick F
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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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chemoleo
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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? 
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Basement Chemist
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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
I am curently hiding from the DEA...
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chemoleo
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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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chemoleo
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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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chemoleo
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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
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d g joshi
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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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chemoleo
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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!!! 
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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vulture
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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]
One shouldn't accept or resort to the mutilation of science to appease the mentally impaired.
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chemoleo
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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!
PS sorry if I am too demanding but thats written into my genes
[Edited on 8-9-2003 by chemoleo]
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KABOOOM(pyrojustforfun)
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what happens to tertiary amines upon nitration?
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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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chemoleo
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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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