Potassium peroxymonosulfate

Potassium peroxymonosulfate
IUPAC name

Potassium peroxysulfate
Other names

Caroat
Oxone
potassium monopersulfate
MPS
Identifiers
CAS number 10361-76-9 Y, 
37222-66-5 (triple salt, see text)
PubChem 61462
ChemSpider 55384 Y
Jmol-3D images Image 1
Properties
Molecular formula KHSO5
Molar mass 152.2 g/mol (614.76 as triple salt)
Appearance off-white powder
Hazards
MSDS Degussa Caroat MSDS
EU Index Not listed
Main hazards Oxidant
Related compounds
Related compounds Potassium persulfate
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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 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.

HSO5− + 2 H+ + 2 e− → HSO4− + H2O

Contents

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]


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.


Uses

Potassium peroxymonosulfate can be used in swimming pools to keep the water clear, thus allowing chlorine in pools to work to sanitize the water rather than clarify the water, resulting in less chlorine needed to keep pools clean.[5] One of the drawbacks of using potassium peroxymonosulfate in pools is it can cause the common DPD #3 water test for combined chlorine to read incorrectly high.[6]

References

  1. ^ "Oxone". Spectral Database for Organic Compounds (SDBS). "National Institute of Advanced Industrial Science and Technology (AIST)". http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_frame_disp.cgi?sdbsno=21455. 
  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): 1031–4. doi:10.1021/ol0340078. PMID 12659566. 
  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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0087 ; Coll. Vol. 8: 87 
  4. ^ 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 
  5. ^ "Benefits of Using a Non-Chlorine Shock Oxidizer Powered by DuPont™ Oxone®." Dupont.com. Accessed July 2011.
  6. ^ "How to accurately measure chlorine levels in water shocked with potassium monopersulfate". Tech note from water test maker Taylor Technologies, originally appeared in Aquatics International. Accessed November 2011

External links

Applications
Technical