Potassium peroxymonosulfate

Potassium peroxymonosulfate

IUPAC name	Potassium peroxysulfate
Other names	Potassium persulfate
Identifiers
CAS number	37222-66-5
SMILES	OS(O[O-])(=O)=O.[K+]
Properties
Molecular formula	KHSO₅
Molar mass	152.17
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Potassium peroxymonosulfate, KHSO₅, is widely used as an oxidizing agent. It is the potassium acid salt of peroxymonosulfuric acid.

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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]

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.

References

^ 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
^ James R. McCarthy, Donald P. Matthews, and John P. Paolini Organic Syntheses, Coll. Vol. 9, p.446; Vol. 72, p.209 Article

Categories: Persulfates | Peroxides | Potassium compounds | Acid salts