Potassium peroxymonosulfate

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Potassium peroxymonosulfate
KHSO5.png
Identifiers
CAS number 10361-76-9 YesY
37222-66-5 (triple salt, see text)
PubChem 11804954
ChemSpider 8053100 N
Jmol-3D images Image 1
Properties
Molecular formula KHSO5
Molar mass 152.2 g/mol (614.76 as triple salt)
Appearance off-white powder
Solubility in water decomposes
Hazards
MSDS Degussa Caroat MSDS
EU Index Not listed
Main hazards Oxidant, Corrosive
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Related compounds
Related compounds Potassium persulfate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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 four companies: Arch Pool Chemicals(a subsidiary of Lonza Pharma Group) Evonik (formerly Degussa) under the tradename Caroat, DuPont under the tradename Oxone, and Hangzhou Focus Chemical Co., Ltd tradenames which are now part of standard chemistry vocabulary. It is a component of a triple salt with the formula 2KHSO5·KHSO4·K2SO4.[2] The standard electrode potential for this compound is +1.44 V with a half reaction generating the hydrogen sulfate.[citation needed]

HSO5 + 2 H+ + 2 e → HSO4 + H2O

Reactions[edit]

MPS 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.[3]

Illustrative of the oxidation power of this salt is the conversion of an acridine derivative to the corresponding acridine-N-oxide.[4]

Acridine oxidation by oxone, standardized.png

MPS will also oxidize a thioether to a sulfone with 2 equivalents.[5] 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.

Oxidation of an oragnic sulfide by oxone.png

Oxone is also used for oxidation of benzylalcohols, benzylbromides and aromatics in acetonitrile-water solvent mixture at reflux. The conversion of secondary benzylbromide to acetophenone is achieved by using oxone at rt. It is an alternative to metal mediated oxidants like KMnO4, K2Cr2O7, OsO4 etc.[6]


Chemical education


Oxidative clevage of olefin can be performed by oxone at reflux.[7]


Chemical education

Uses[edit]

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.[8] 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.[9]

References[edit]

  1. ^ "DuPont MSDS". 
  2. ^ "Oxone". Spectral Database for Organic Compounds (SDBS). "National Institute of Advanced Industrial Science and Technology (AIST)". 
  3. ^ 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. 
  4. ^ 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 
  5. ^ James R. McCarthy, Donald P. Matthews, and John P. Paolini (1998), Reaction of Sulfoxides with Diethylaminosulfur Trifluoride, Org. Synth. ; Coll. Vol. 9: 446 
  6. ^ Oxidation of benzyl alcohols, benzyl halides, and alkylbenzenes with oxone, K. N. Parida et al, http://www.sciencedirect.com/science/article/pii/S0040402012014068
  7. ^ Oxidation cascade with oxone: cleavage of olefins to carboxylic acids, K. N. Parida et al http://www.sciencedirect.com/science/article/pii/S0040402014000842
  8. ^ "Benefits of Using a Non-Chlorine Shock Oxidizer Powered by DuPont™ Oxone®." Dupont.com. Accessed July 2011.
  9. ^ "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[edit]

Applications
Technical