cryomancer
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NH2 -> NO2 Crazy idea
So here is a crazy idea for a Trinitrotoluene (TNT) synthesis. Its completely theoretical but i believe that it
should be explored for the sake of different reaction mechanisms.
The idea is based around the fact that amines can be oxidized to nitro groups. I first learned of this by watching
"Extractions&Ire, Making Sodium 5,5'-AzoTetrazole From 5-Atz" where he oxidized an amine group. It wasnt to a NO2 but he mentioned that KMnO4 has
that chemical ability.
With that being said, amines are fairly easy to get a hold of or synthesize and the idea was to oxidize
2,4,6-Triaminotoluene to TNT in one step after its formation. Through this method you should be able to skip the usage of valuable concentrated
sulfuric and nitric acid.
Thoughts?
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DraconicAcid
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I'm not sure how easily available that particular amine will be. I'd expect it to be easier to make the TNT the usual route.
I'd also worry that permanganate would also oxidize the methyl group to a carboxylic acid.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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cryomancer
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Quote: Originally posted by DraconicAcid  | I'm not sure how easily available that particular amine will be. I'd expect it to be easier to make the TNT the usual route.
I'd also worry that permanganate would also oxidize the methyl group to a carboxylic acid. |
Hmmm, didnt think about that. Im only in Organic Chem 1 so my knowladge is limited. A quick search did not produce a
synthesis for the amino compound. And this isnt just for 2,4,6-Triaminotoluene but it could be used for other amino compounds and turn them into nirto
compounds nor does KMnO4 have to be the oxidizing agent
[Edited on 27-11-2018 by cryomancer]
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nitro-genes
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My guess would be that the products formed would depend greatly on oxidizer used and pH during the reaction. Oxone is one of the more OTC reagents
being capable of amine to nitro conversion. Under neutral conditions (suitable for amine to nitro group conversion), the amine groups may already
hydrolyze. This method is used for example to produce phoroglucinol from 1,3,5 triamino benzene. The mechanism of amine->nitro coversion being
probably a radical reaction and 3 amino groups on one ring, a mix of azo compounds, tars, polymers from coupling reactions, quinones, schiffbases, or
even complete ring destruction seems far more likely is my uneducated guess. So, I don't think there are conditions possible to form TNT selectively,
could be wrong though...
Attachment: Oxidation of aromatic amines to nitrocompounds.pdf (731kB)
This file has been downloaded 766 times
[Edited on 28-11-2018 by nitro-genes]
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cryomancer
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^
Its funny, i found that exact article just before i posted this. May not be easily feasable but it might still have
some other uses. Thats the beauty of chemistry, finding the cheapest and easiest method of producing something most people would not want us to have,
amongst other things of course.
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Tdep
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I think that there's a method of making RDX through that method? Making the amine groups and then oxidising them to NO2? That's sort of similar to
what you are proposing. I could look it up but then i'll be distracted from my actual work for the next 3 hours....
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clearly_not_atara
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1,3,5-triaminobenzenes are very unstable. Maybe try chlorinating 2,4-dinitrotoluene and react with ammonia. Then you could oxidize that. Note that
ring-halogenation will be very difficult, but Cl2+AlCl3 should do it.
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cryomancer
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| Quote: Originally posted by clearly_not_atara | | 1,3,5-triaminobenzenes are very unstable. Maybe try chlorinating 2,4-dinitrotoluene and react with ammonia. Then you could oxidize that. Note that
ring-halogenation will be very difficult, but Cl2+AlCl3 should do it. |
Interesting work around, i have heard that getting that third NO2 group on the DNT is rather difficult and requires
super high concentrations of H2SO4 to get it to react, so going as far as Oleum. This being 98% Sulfuric acid with a but of SO3 added in.
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VSEPR_VOID
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Why not do a trail run with aniline first to test out if you can oxidize an aryl amine
Within cells interlinked
Within cells interlinked
Within cells interlinked
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