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Author: Subject: 2,6-dinitro-4-diazoresorcinol
dave321
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[*] posted on 3-12-2012 at 13:16
2,6-dinitro-4-diazoresorcinol


hi all,

how would one synthesise the above material ?
it is a precursor to making strontium diazinate, a material proposed for lead free (flat d80-1 type )bullet hits
(which usually use lead styphnate)

i have read all the posts on lead styphnate but a succesful preparation eludes me.

stontium diazinate may be easier.
is it a matter of nitrating resorcinol followed by diazotisation?
thanks
d321
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kristofvagyok
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[*] posted on 4-12-2012 at 14:00


Why is a stontium salt better than a lead salt? Same toxic and not that less sensitive, the only difference is the color of the flameball when you blow up yourself.

Some lead picrate:


The synthesis of styphnic acid is really easy, if you cant prepare that I don't think that you should make diazonium salts.

Also: from styphnic acid you first have to reduce it to 2,4-dinitro-6-amino-resorcinol and then make the diasotation to get the title comound. The problem is: aromatic diazonium compounds like that are not so stable, especially when they form salts with heavier elements like Sr.




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dave321
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[*] posted on 4-12-2012 at 14:29


reason for strontium vs lead is the percieved lower toxicity of the strontium salt, rightly or wrongly.

could you post a suggested synth of the diazonium salt ?

it cant be any worse than handling fulminates and only in small scale.

i am trained in lab procedures although not an organic chemist by profession.

my experience is largely with pyro compositions, and i know primaries are not in the same league or ball park

appreciate any help.
see below for patent info
http://osdir.com/patents/Explosive-charges/Pyrotechnic-body-...

d321
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Adas
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[*] posted on 5-12-2012 at 09:34


Wikipedia says that Sr is not toxic, it may be even benefical (against osteoporosis). Only the radioactive isotopes are dangerous. But you can as well make strontium styphnate :D



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Boffis
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[*] posted on 5-12-2012 at 11:51


The compound you want should be available from styphnic acid.

Styphnic acid can be reduced to the dinitro-monoamino compound by precisely the sample method as used to produce picramic acid discussed elsewhere on this site but 2 possible isomers are possible (2 amino 4,6 dintroresorcinol and 4 amino 2,6 dinitro resorcinol, the later is the one you require but how you seperate them or indeed which on predominates I don't know). This compound can be diazotises under cold fairly acid conditions and the cold solution rendered strong alkaline to turn the diazonium cation in the the anionic diazonate ion. A soluble strontium salt is them added to the solution to precipitate the required salt. I don't know how soluble the strontium salt will be.
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dave321
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[*] posted on 8-12-2012 at 14:27


thanks for the info
d321
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AndersHoveland
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[*] posted on 9-12-2012 at 03:48


Quote: Originally posted by Boffis  
2 possible isomers are possible (2 amino 4,6 dintroresorcinol and 4 amino 2,6 dinitro resorcinol, the later is the one you require but how you seperate them or indeed which on predominates I don't know).

I do not think it would matter much whether they are separated.
Either would form diazo compounds.

https://www.sciencemadness.org/whisper/viewthread.php?tid=48...

Styphinic acid can be produced by the action of nitric acid on 3-nitrophenol. An old text states that the reaction proceeds through the transient formation of tetranitro phenol, the nitro group in the 2-position being very reactive, and hydrolysing with water to be replaced with a hydroxyl group.

[Edited on 9-12-2012 by AndersHoveland]




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PHILOU Zrealone
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[*] posted on 10-12-2012 at 12:23


Quote: Originally posted by AndersHoveland  

Styphinic acid can be produced by the action of nitric acid on 3-nitrophenol. An old text states that the reaction proceeds through the transient formation of tetranitro phenol, the nitro group in the 2-position being very reactive, and hydrolysing with water to be replaced with a hydroxyl group.


Actually, it is the nitro of position 3 and not 2 that is hydrolysed...because it is in the neightbourghood with two NO2 (one in position 2 and one on position 4); as such it is very prone to nitro-nitrite rearrangement and hydrolysis.
Thus 2,3,4,6-tetranitrophenol turns easily into 2,4,6-trinitroresorcinol.

Also about isomers...
2-amino-4,6-dinitroresorcinol
4-amino-2,6-dinitroresorcinol (equal to 6-amino-2,4-dinitroresorcinol)
are possible

And
2-amino-4,6-dinitroresorcinol will give two isomers upon diazotation because the diazonium is hold between two hydroxy groups.

Thus in fine, if one doesn't serparate the initial molecular mix before diazotation; he will end up with 3 isomeric cyclic diazoniums...

To add a bit to the complexity...there exists also uncyclic diazoniums isomers based on para-quinon structures. As an example 2,4-dinitro-para-aminophenol upon diazotation afwords a stable diazonium salt while the OH group is at the oposite side of the aromatic ring.

[Edited on 11-12-2012 by PHILOU Zrealone]




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