POTASSIUM PEROXYMONOSULFATE

(Redirected from Oxone)

'Potassium peroxymonosulfate', KHSO5, is widely used as an oxidizing agent. It is the potassium acid salt of peroxymonosulfuric acid.
The potassium salt is marketed by two companies: Degussa under the tradename 'Caroat®' and DuPont under the tradename 'Oxone®', tradenames which are now part of standard chemistry vocabulary. It is a component of a 'triple salt' with the formula 2KHSO5·KHSO4·K2SO4. The standard electrode potential for this compound is -1.44 V with a half reaction generating the hydrogen sulfate.
::HSO4- + H2O → HSO5- + 2 H+ + 2 e-
Illustrative of the oxidation power of this salt is the conversion of an acridine to the corresponding acridine-N-oxide.[1]
:
acridine to acridine-N-oxide oxidation by Oxone


It will also oxidize a thioether to a sulfone with 2 equivalents.[2] With one equivalent the reaction converting sulfide to sulfoxide is much faster than that of sulfoxide to sulfone, so the reaction can conveniently be stopped at that stage if so desired.
:
sulfide to sulfone oxidation by oxone



Contents
References

References


1. Thomas W. Bell, Young-Moon Cho, Albert Firestone, Karin Healy, Jia Liu, Richard Ludwig, and Scott D. Rothenberger Organic Syntheses, Coll. Vol. 8, p.87; Vol. 69, p.226 Article
2. James R. McCarthy, Donald P. Matthews, and John P. Paolini Organic Syntheses, Coll. Vol. 9, p.446; Vol. 72, p.209 Article


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