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Potassium peroxymonosulfate

From Wikipedia, the free encyclopedia
(Redirected fromOxone)
"Oxone" redirects here. Not to be confused with the gasozone.
Not to be confused withPotassium persulfate.
Potassium peroxymonosulfate
Names
IUPAC name
Potassium peroxysulfate
Other names
Caroat
potassium monopersulfate
MPS
KMPS
potassium caroate
non-chlorine shock[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.030.158Edit this at Wikidata
UNII
  • InChI=1S/K.H2O5S/c;1-5-6(2,3)4/h;1H,(H,2,3,4)/q+1;/p-1 ☒N
    Key: OKBMCNHOEMXPTM-UHFFFAOYSA-M ☒N
  • InChI=1S/K.H2O4S/c;1-4-5(2)3/h;1H,(H,2,3)/q+1;/p-1
  • Key: GZHFEBOLZPYNER-UHFFFAOYSA-M
  • InChI=1/K.H2O5S/c;1-5-6(2,3)4/h;1H,(H,2,3,4)/q+1;/p-1
    Key: OKBMCNHOEMXPTM-REWHXWOFAJ
  • [K+].[O-]S(=O)(=O)OO
Properties
KHSO5
Molar mass152.2 g/mol (614.76 g/mol as triple salt)
AppearanceOff-white powder
Decomposes
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Oxidant, corrosive
NFPA 704 (fire diamond)
Safety data sheet (SDS)Fisher Scientific SDS
Related compounds
Related compounds
Potassium persulfate
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Potassium peroxymonosulfate is widely used as anoxidizing agent, for example, in pools and spas (usually referred to as monopersulfate or "MPS"). It is thepotassiumsalt ofperoxymonosulfuric acid. Potassium peroxymonosulfate per se is rarely encountered. It is often confused with the triple salt2KHSO5·KHSO4·K2SO4, known asOxone.

Thestandard electrode potential for potassium peroxymonosulfate is +1.81 V with ahalf reaction generating the hydrogen sulfate (pH = 0):[3]

HSO−5 + 2H+ + 2e− → HSO−4 + H2O

Oxone

[edit]

Potassium peroxymonosulfate per se is a relatively obscure salt, but its derivative called Oxone is of commercial value. Oxone refers to the triple salt2KHSO5·KHSO4·K2SO4. As such about one third by weight is potassium peroxymonosulfate. Oxone has a longer shelf life than does potassium peroxymonosulfate. A white, water-soluble solid, Oxone loses <1% of its oxidizing power per month.[4]

Oxone, which is commercially available, is produced from peroxysulfuric acid, which is generated in situ by combiningoleum andhydrogen peroxide. Careful neutralization of this solution with potassium hydroxide allows the crystallization of the triple salt.

Uses

[edit]

Cleaning

[edit]

Oxone is used widely for cleaning. It whitens dentures,[5] oxidizes organic contaminants in swimming pools,[6]and cleans chips for the manufacture of microelectronics.[5][7][8]

Organic oxidations

[edit]

Oxone is a versatile oxidant in organic synthesis. It oxidizesaldehydes tocarboxylic acids; in the presence of alcoholic solvents, theesters may be obtained.[9] Internalalkenes may be cleaved to twocarboxylic acids (see below), while terminal alkenes may beepoxidized.Sulfides givesulfones, tertiaryamines giveamine oxides, andphosphines givephosphine oxides.

Further illustrative of theoxidative power of this salt is the conversion of anacridine derivative to the corresponding acridine-N-oxide.[10]

Oxone oxidizessulfides tosulfoxides and then tosulfones.[11]

Oxone convertsketones todioxiranes, which are used for diverseoxidations in organic synthesis. The dominant reagentdimethyldioxirane (DMDO) forms upon treatment ofacetone with oxone. Dioxiranes are versatile, especially for theepoxidation ofolefins.[12] Dioxiranes are also oxidize other unsaturated functionality, heteroatoms, and alkane C-H bonds.[13]

The Shi epoxidation
The Shi epoxidation

Oxone is used in the production of some organicperiodinanes, notably the oxidation of2-iodobenzoic acid to2-iodoxybenzoic acid (IBX).[14]

Oxidation of 2-iodobenzoic acid to IBX
Oxidation of 2-iodobenzoic acid to IBX

Other uses

[edit]

Oxone has been investigated for thedelignification of wood.[15]

Ammonium,sodium, andpotassium salts ofHSO−5 are used in theplastics industry asradical initiators forpolymerization. They are also used asetchants,oxidative desizing agents for textile fabrics, and for decolorizing and deodorizing oils.

References

[edit]
  1. ^Wu, Mingsong; Xu, Xinyang; Xu, Xun (November 2014). "Algicidal and Bactericidal Effect of Potassium Monopersulfate Compound on Eutrophic Water".Applied Mechanics and Materials.707: 259.doi:10.4028/www.scientific.net/AMM.707.259.S2CID 98000605.
  2. ^"DuPont MSDS"(PDF). Archived fromthe original(PDF) on 2014-08-15. Retrieved2012-01-26.
  3. ^Spiro, M. (1979). "The standard potential of the peroxosulphate/sulphate couple".Electrochimica Acta.24 (3):313–314.doi:10.1016/0013-4686(79)85051-3.ISSN 0013-4686.
  4. ^Crandall, Jack K.; Shi, Yian; Burke, Christopher P.; Buckley, Benjamin R. (2001).Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd.doi:10.1002/047084289x.rp246.pub3.ISBN 978-0-470-84289-8.
  5. ^abHarald Jakob; Stefan Leininger; Thomas Lehmann; Sylvia Jacobi; Sven Gutewort. "Peroxo Compounds, Inorganic".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a19_177.pub2.ISBN 978-3-527-30673-2.
  6. ^Pool School. Trouble Free Pool. p. PT4. RetrievedNovember 30, 2018.
  7. ^Peroxy Compounds Human Health and Ecological Draft Risk Assessment DP 455445, 455446 (Report). United States Environmental Protection Agency. 2020-03-11. p. 9-10. Retrieved2021-09-24.
  8. ^Wacławek, Stanisław; Lutze, Holger V.; Grübel, Klaudiusz; Padil, Vinod V.T.; Černík, Miroslav; Dionysiou, Dionysios. D. (2017-12-15). "Peroxy Compounds Human Health and Ecological Draft Risk Assessment DP 455445, 455446".Chemical Engineering Journal.330:44–62.doi:10.1016/j.cej.2017.07.132.
  9. ^Benjamin R. Travis; Meenakshi Sivakumar; G. Olatunji Hollist & 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.
  10. ^Bell, Thomas W.; Cho, Young-Moon; Firestone, Albert; Healy, Karin; Liu, Jia; Ludwig, Richard; Rothenberger, Scott D. (1990). "9-n-Butyl-1,2,3,4,5,6,7,8-Octahydroacridin-4-ol".Organic Syntheses.69: 226.doi:10.15227/orgsyn.069.0226.
  11. ^McCarthy, James R.; Matthews, Donald P.; P. Paolini, John (1995). "Reaction of Sulfoxides with Diethylaminosulfur Trifluoride".Organic Syntheses.72: 209.doi:10.15227/orgsyn.072.0209.
  12. ^Adam, W.; Saha-Moller, C.; Zhao, C.-G. (2004). "Dioxirane Epoxidation of Alkenes".Org. React.61: 219.doi:10.1002/0471264180.or061.02.
  13. ^Adam, W.; Zhao, C.-G.; Jakka, K. (2007). "Dioxirane Oxidations of Compounds other than Alkenes".Org. Reactions.69: 1.doi:10.1002/0471264180.or069.01.
  14. ^Frigerio, M.; Santagostino, M.; Sputore, S. (1999). "A User-Friendly Entry to 2-Iodoxybenzoic Acid (IBX)".J. Org. Chem.64 (12):4537–4538.doi:10.1021/jo9824596.
  15. ^Springer, E. L.; McSweeny, J. D. (1993)."Treatment of softwood kraft pulps with peroxymonosulfate before oxygen delignification".TAPPI Journal.76 (8):194–199.ISSN 0734-1415. Archived fromthe original on 2011-09-29. Retrieved2011-05-14.
H, (pseudo)halogens
chalcogens
pnictogens
B, C group
transition metals
organic
Salts and covalent derivatives of thepersulfate ion
H2SO5
H2S2O8		He
LiBeBC(NH4)2S2O8OFNe
Na2S2O8MgAlSiP(SO5)2−
(S2O8)2−		ClAr
KHSO5
K2S2O8		CaScTiVCrMnFeCoNiCuZnGaGeAsSeBrKr
RbSrYZrNbMoTcRuRhPdC20H20N4AgS2O8CdInSnSbTeIXe
CsBa*LuHfTaWReOsIrPtAuHgTlPbBiPoAtRn
FrRa**LrRfDbSgBhHsMtDsRgCnNhFlMcLvTsOg
 
*LaCePrNdPmSmEuGdTbDyHoErTmYb
**AcThPaUNpPuAmCmBkCfEsFmMdNo
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