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Potassium peroxymonosulfate
KHSO5.png
IUPAC name
Other names Caroat
Oxone
Identifiers
CAS number 10361-76-9 Yes check.svgY,
37222-66-5 (triple salt, see text)
Properties
Molecular formula KHSO5
Molar mass 192.27 g/mol
Appearance off-white powder
Hazards
MSDS Degussa Caroat MSDS
EU Index Not listed
Main hazards Oxidant
Related compounds
Related compounds Potassium persulfate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Potassium peroxymonosulfate (also known as 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. 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-

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.[1]

Illustrative of the oxidation power of this salt is the conversion of an acridine derivative to the corresponding acridine-N-oxide.[2]

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

It will also oxidize a thioether to a sulfone with 2 equivalents.[3] 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

  1. ^ 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: 1031. doi:10.1021/ol0340078.  
  2. ^ 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., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0087  ; Coll. Vol. 8: 87  
  3. ^ James R. McCarthy, Donald P. Matthews, and John P. Paolini (1998), "Reaction of Sulfoxides with Diethylaminosulfur Trifluoride", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv9p0446  ; Coll. Vol. 9: 446  

External links

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