Potassium peroxymonosulfate

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Potassium peroxymonosulfate
Names
IUPAC name
Potassium peroxysulfate
Other names
Caroat
Oxone
potassium monopersulfate
MPS
Identifiers
ECHA InfoCard 100.030.158 Edit this at Wikidata
Properties
KHSO5
Molar mass 152.2 g/mol (614.76 as triple salt)
Appearance off-white powder
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Oxidant
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Potassium peroxymonosulfate (also known as MPS, potassium monopersulfate, and the trade names Caroat and Oxone) is widely used as an oxidizing agent. It is the potassium 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.[1] The standard electrode potential for this compound is −1.44 V with a half reaction generating the hydrogen sulfate.[citation needed]

HSO4− + H2O → HSO5− + 2 H+ + 2 e−

Reactions

Oxone is a versatile oxidant. It oxidizes aldehydes to carboxylic acids; in the presence of alcoholic solvents, the esters may be obtained. Internal alkenes may be cleaved to two carboxylic acids, while terminal alkenes may be epoxidized. Thioethers give sulfones, tertiary amines give amine oxides, and phosphines give phosphine oxides.[2]

Illustrative of the oxidation power of this salt is the conversion of an acridine derivative to the corresponding acridine-N-oxide.[3]

acridine-derivative to acridine-N-oxide-derivative oxidation by Oxone
acridine-derivative to acridine-N-oxide-derivative oxidation by Oxone

It will also oxidize a thioether to a sulfone with 2 equivalents.[4] 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
sulfide to sulfone oxidation by oxone

References

  1. ^ "Oxone". Spectral Database for Organic Compounds (SDBS). "National Institute of Advanced Industrial Science and Technology (AIST)".
  2. ^ Benjamin R. Travis, Meenakshi Sivakumar, G. Olatunji Hollist, and Babak Borhan (2003). "Facile Oxidation of Aldehydes to Acids and Esters with Oxone". Organic Letters. 5 (7): 1031. doi:10.1021/ol0340078. PMID 12659566.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ 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.
  4. ^ 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
Technical
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