Sciencemadness Discussion Board

Can an organic nitrite be oxidized to nitrate ?

franklyn - 23-3-2013 at 06:39

utilizing an appropriate oxidizer ,
perhaps H2O2 and a catalyst , or even ozone.
Just as 2 NaONO + O2 => 2 NaONO2 is

.

vmelkon - 24-3-2013 at 07:56

My guess is, probably not. An oxidizer like H2O2 or O3 would most likely change the rest of the molecule in question.

http://en.wikipedia.org/wiki/Ozonolysis

[Edited on 24-3-2013 by vmelkon]

ElectroWin - 24-3-2013 at 10:30

nitrites in foods do oxidize to nitrates, i hear. what is the mechanism for that?

woelen - 24-3-2013 at 11:04

Nitrites in food are inorganic, ionic, containing the ion NO2(-). Nitrite ion is fairly easily oxidized by oxygen from air to nitrate ion. This reaction is not immediate, but if you keep a solution of e.g. NaNO2 in contact with air, then after a few days quite a lot of the nitrite is oxidized to nitrate. The solid salts are more resistant to oxidation.

franklyn - 1-4-2013 at 08:02


This notion has been suggested before in this forum

www.sciencemadness.org/talk/viewthread.php?tid=6395&goto...

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AJKOER - 3-4-2013 at 17:34

I recall reading where the action of H2O2, in a particular instance, on an organic nitrite resulted in an oxynitrite, and not a nitrate.

I may be able to find the reference (biochemistry).
[EDIT] Found something (see "The decomposition of peroxynitrite does not yield nitroxyl anion and singlet oxygen", link: www.pnas.org/content/97/15/8216.full.pdf ). To quote:

"Fresh solutions of peroxynitrite were prepared
before use by reacting nitrite with acidified hydrogen peroxide
at room temperature in a quenched-flow system. This system was
optimized as we described recently (16) to produce high yields of
ONOO2 with known contaminations by residual nitrite, nitrate,
and H2O2. "
------------------------------------------------------------

To answer your question: Can an organic nitrite be oxidized to nitrate? Consider HOCl prepared in situ from NaOCl and Acetic acid (just my speculation). Another possibility (less likely), use one of the more stable organic hypochlorites, which have been reported as behaving like anhydrous Hypochlorous acid.

Basis: Inorganic chemistry in aqueous solutions:

HOCl + [NO2]- --> HCl + [NO3]-


[Edited on 4-4-2013 by AJKOER]