ethylamine-->nitroethane

[El_Zorro]

I've used TFSE, and everybody seems to like the idea of ethylamine-->nitroethane via oxidation, but nobody seems to have done anything about it.  It seems to me like this would be a kick ass synth, especially if all that's needed is ethylamine and a dichromate, or maybe a permanganate.  Does anyone have thoughts on this reaction?  I am thinking of performing a test synth using dichromate, or maybe permanganate, but I really have no idea of what the reaction conditions should be, and any help would be appreciated.

This has come up before, but it seems like as soon as someone is about to post the procedure for anything, the thread will end, as if everybody's keeping this a secret.  If this is a Hive secret, and y'all don't want me posting about it, then by all means, PM me , but if not, then please share your thoughts.
Who is that masked man?

[Rhodium]

When searching, you didn't find a single preparation of nitroalkanes from aminoalkanes? Not even a literature reference?

[Chemikaze]

I`m interested in this process too.But Antoncho once told me that it wouldnt be successfull?
He said that you`ll need anhydrous conditions,and even so there`s a little chance.He never backed up his words,so I guess it was just an assumption (as being a mother of all fuckups).
Also I did a search in Patent database and found "nill"
Anyway, how do you think it would look? Should we use some solvent (it better be anhydrous)?
Or should we do it like NaEtSO₄+NaNO₂ solventless,thoroughly mix oxidizer and amine?

When I die bury me upside down so the world can kiss my ass.

[Aurelius]

Post 355380

(Aurelius: "newest method", Chemistry Discourse)

[Aurelius]

Oh yeah, not to mention that Rhodium recent added all of this post to his web site.  if you'd just spend some time perusing what's there, you'd find 90%+ of the answers to your questions.  (b/c aurelius always does aurelius' own seaching  thanks Rhodium)

[Chemikaze]

Yes,Aurelius I`ve seen that post.That perbenzoic acid method isn`t what we are looking for,isn`t it:)
You give some references for permanganate method,this one is interesting Org Synth CV 5, 845, but i looked through others and did not find them to be of any use
.

This may be of some interest:
The oxidation of trimethylamine by OH radicals in aqueous solution, as studied by pulse radiolysis, ESR, and product analysis. The reactions of the alkylamine radical cation, the aminoalkyl radical, and the protonated aminoalkyl radical.
Das, S.; von Sonntag, C.
Z. Naturforsch. B, Anorg. Chem., Org. Chem. 41B(4): 505-13 (1986)


When I die bury me upside down so the world can kiss my ass.

[WHITE_DEVIL]

It seems that ozone will oxidise ammonia to nitrate under the right conditions

Ozone has an intensive influence on the nitrogen circuit.  At pH-values of more than 7, the toxic ammonia is oxidized to nitrate and at ph-values of around 7, the toxic ammonia is not oxidized, so bacterial oxidation is required.  But in any case the very toxic nitrite step will be oxidized by ozone to nitrate - this reaction being pH-value independent - so nitrite is oxidized to nitrate.  This is most important, as nitrite even in small traces is a poisonous compound for fish.  The decrease of nitrite and ammonia is the faster the higher the ozone content is.

er.. so basically maybe you could oxidise ethylamine to nitroethane using ozone. I'd imagine yields would be pretty high too. Ive seen it available in small aerosol cans for small aqauria and you can also buy ozone generators although they can be rather expensive.

http://homex.coolconnect.com/member3/bengtecktan/koi/ozone_facts.htm

[Aurelius]

was there a reason why this method was thrown out as a practical application?  any thoughts?