Mardec
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Reducing a nitrate group of PETN
Hey, sorry for starting a new thread as a first post. But I just got a great idea, as so I think..
It involves reducing a nitrate group of PETN. Yes only one.
Somewhat like picric acid to picramic acid. But this is done with a nitro group in stead of a nitrate group.
Anorganic nitrates can be reduced to ammonium with zink or aluminum (devarda's alloy).
But I don't know much about reducing organic nitrates. With Na2S maybe?
The main problem will be reducing only one in stead of all 4 nitrate groups.
But if it works you will get a molecule like the nitrated tris (there is a topic about this) but with an extra methylene group between the center
carbon and the amine group.
This will hopefully make a strong enough base for my idea.
The idea was basicly then just adding a perchlorate group from HClO4 to the amine group. Or picric/styphnate acid.
And so hopefully getting an even better explosive. Quite exotic even.
But this is all pure speculation and theory. Would this have a slight chance of working? My organic chemistry isn't that great as I would like it to
be. But I am working on that.
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Axt
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No, if it were to bear any analogy to picric to picramic you would end up with an oxyamine -O-NH2 though this doesnt happen either. Reduction of a
nitrate group (or denitration) with sulphides or any other common reduction agents yields the parent alcohol.
See US patents 3709920, 3714199 & 3714200 for synthesis of methylenebis(oxyamine).
[Edited on 29-5-2007 by Axt]
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quicksilver
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There is a "PEN" utilizing a tri-nitrated product. This occurs in the straight production of PETN; some of the end product material is PEN. Apparently
due to variances in the manufacturing process.
In Legard's books there has been a few experiments devoted to what he calls Pentaerythritol Trinitrate. He makes reference to the Rhom & Haas
Company's patent (1968). It seems there IS existing material out there regarding this issue. And so what if it's your first post? It seems like an
interesting subject....
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Mardec
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Quicksilver goddammit you are right, when I read your post I remembered reading something about PEtrinitrate. It even is listen om Megalomania's lab
(roguesci) as Petrin.
Interesting, the only thing that will need to be done then is Turning that OH group in a NH2 group.
I think this will be possible with, HBr. That will make water and PEBromoTriNitrate.
Letting this react with NaNH2 will give NaBr and PEAminoTriNitrate. And here is the molecule I want :-).
Is this route possible? If I am making serious mistakes please tell me, I am eager to learn.
But making the trinitrate ester isn't possible the way megalomania says. I don't have the necessairy chemicals..
Btw, what would this yield= Petrin + perchloric acid? Will it just make PETN and PETPerchlorate? :s (if it is even possible?) or will it make
PETrinitratePerchlorate?
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Axt
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I really dont think it worth persuing acid salts of nitrate esters, in view of the instability of the others such as those derived from
tris(hydroxymethyl)aminomethane and ethanolamine. The monoamine perchlorate also has around same oxygen balance as PETN and probably similar
performance. It would be better to target the tetraamine and derivatives of that.
Pentaerythrityl tetrabromide: http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV4...
[Edited on 30-5-2007 by Axt]
Attachment: The amino-derivatives of pentaerythritol. Part I. Preparation - J. Chem. Soc., 1938, 1588 - 1595.pdf (991kB)
This file has been downloaded 1067 times
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Mardec
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Thanks for the tips Axt. You are probably right about the whole one aminegroup idea.
I Was just thinking (hoping) that maybe these hybride (nitrate and perchlorate) ester might give off more power without the loss of stability.
And thanks for the very interesting document.
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quicksilver
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I don't have good source material for much of this issue but I do know where to start to find it.....first dig up Legard's book (Preperitory Manual of
Explosives) but get the 3rd edition as it has MUCH better sourcing and track his documentation. What I heard was that the product was found in most
all batches of PETN. There are possibly very simple reasons for it's existence. I know that it is still a functional energetic material and actually
may be the bulk of PETN made with solid nitrates.
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Bolt
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The subject of PETriN came up at RS recently. Attached is this reference:
Organic Acid Esters of Pentaerythritol Trinitrate
N. S. Marans, D. E. Elrick, R. F. Preckel
J. Am. Chem. Soc.; 1954; 76(5); 1304-1306.
The article describes the nitration of pentaerythritol monoacetate and then the controlled saponification of the resulting molecule. The 'controlled
hydrolysis' transforms the acetyl group back to a hydroxyl group; however, the nitric esters remain unaffected.
Attachment: organic_acid_esters_of_pentaerythritol_trinitrate.pdf (447kB)
This file has been downloaded 1270 times
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