Potassium peroxymonosulfate

Template:Chembox new Potassium peroxymonosulfate, K H S O₅, 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

References

^ 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". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 87.
^ James R. McCarthy, Donald P. Matthews, and John P. Paolini (1998). "Reaction of Sulfoxides with Diethylaminosulfur Trifluoride". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 9, p. 446.

External links

Applications

DuPont Oxone® Monopersulfate Compound Applications
Potassium Monopersulfate – Article on precious metal extraction from distributor Green Controll

Technical

DuPont Oxone® Monopersulfate Compound Technical Information

[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". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 87.

[2] James R. McCarthy, Donald P. Matthews, and John P. Paolini (1998). "Reaction of Sulfoxides with Diethylaminosulfur Trifluoride". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 9, p. 446.

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