Potassium peroxymonosulfate

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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
Hazards
MSDS Degussa Caroat Safety Data Sheet
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.

The potassium salt is marketed by two companies: Evonik (formerly 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

[edit] References

  1. ^ Thomas W. Bell, Young-Moon Cho, Albert Firestone, Karin Healy, Jia Liu, Richard Ludwig, and Scott D. Rothenberger (1993). "9-n-Butyl-1,2,3,4,5,6,7,8-Octahydroacridin-4-ol". Org. Synth.; Coll. Vol. 8: 87. 
  2. ^ James R. McCarthy, Donald P. Matthews, and John P. Paolini (1998). "Reaction of Sulfoxides with Diethylaminosulfur Trifluoride". Org. Synth.; Coll. Vol. 9: 446. 

[edit] External links

Applications
Technical