Potassium peroxymonosulfate

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Potassium peroxymonosulfate - Wikipedia

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Potassium peroxymonosulfate
Names

IUPAC name Potassium peroxysulfate
Other names Caroat potassium monopersulfate MPS KMPS potassium caroate non-chlorine shock^[1]
Identifiers
CAS Number	10058-23-8^Y 37222-66-5 (triple salt)^Y 70693-62-8^Y
3D model (JSmol)	Interactive image
ChemSpider	8053100^N
ECHA InfoCard	100.030.158
PubChem CID	11804954
UNII	040ZB27861^Y HL6A2XXU5D (triple salt)^Y
CompTox Dashboard (EPA)	DTXSID1034840
InChI 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
SMILES [K+].[O-]S(=O)(=O)OO
Properties
Chemical formula	KHSO₅
Molar mass	152.2 g/mol (614.76 g/mol as triple salt)
Appearance	Off-white powder
Solubility in water	Decomposes
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Oxidant, corrosive
NFPA 704 (fire diamond)	^[2] 3 0 1
Safety data sheet (SDS)	Degussa Caroat MSDS
Related compounds
Related compounds	Potassium persulfate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Potassium peroxymonosulfate is widely used as an oxidizing agent, for example, in pools and spas (usually referred to as monopersulfate or "MPS"). It is the potassium salt of peroxymonosulfuric acid. Potassium peroxymonosulfate per se is rarely encountered. It is often confused with the triple salt 2KHSO₅·KHSO₄·K₂SO₄, known as Oxone.

The standard electrode potential for potassium peroxymonosulfate is +1.81 V with a half reaction generating the hydrogen sulfate (pH = 0):^[3]

HSO−5 + 2H⁺ + 2e⁻ → HSO−4 + H₂O

Oxone

Potassium peroxymonosulfate per se is a relatively obscure salt, but its derivative called Oxone is of commercial value. Oxone refers to the triple salt 2KHSO₅·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 combining oleum and hydrogen peroxide. Careful neutralization of this solution with potassium hydroxide allows the crystallization of the triple salt.

Uses

Cleaning

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

Oxone is a versatile oxidant in organic synthesis. It oxidizes aldehydes to carboxylic acids; in the presence of alcoholic solvents, the esters may be obtained.^[9] Internal alkenes may be cleaved to two carboxylic acids (see below), while terminal alkenes may be epoxidized. Sulfides give sulfones, tertiary amines give amine oxides, and phosphines give phosphine oxides.

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

Oxone oxidizes sulfides to sulfoxides and then to sulfones.^[11]

Oxone converts ketones to dioxiranes, which are used for diverse oxidations in organic synthesis. The dominant reagent dimethyldioxirane (DMDO) forms upon treatment of acetone with oxone. Dioxiranes are versatile, especially for the epoxidation of olefins.^[12] Dioxiranes are also oxidize other unsaturated functionality, heteroatoms, and alkane C-H bonds.^[13]

Other uses

Oxone has been investigated for the delignification of wood.^[14]

Ammonium, sodium, and potassium salts of H are used in the plastics industry as radical initiators for polymerization. They are also used as etchants, oxidative desizing agents for textile fabrics, and for decolorizing and deodorizing oils.

References

^ 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.
^ "DuPont MSDS" (PDF). Archived from the original (PDF) on 2014-08-15. Retrieved 2012-01-26.
^ 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.
^ 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.
^ ^a ^b Harald 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 978-3527306732.
^ Pool School. Trouble Free Pool. p. PT4. Retrieved November 30, 2018.
^ Peroxy Compounds Human Health and Ecological Draft Risk Assessment DP 455445, 455446 (Report). United States Environmental Protection Agency. 2020-03-11. p. 9-10. Retrieved 2021-09-24.
^ 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.
^ 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.
^ 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.
^ 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.
^ Adam, W.; Saha-Moller, C.; Zhao, C.-G. (2004). "Dioxirane Epoxidation of Alkenes". Org. React. 61: 219. doi:10.1002/0471264180.or061.02.
^ 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.
^ 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 from the original on 2011-09-29. Retrieved 2011-05-14.

v t e Potassium compounds
H, (pseudo)halogens	KF KHF₂ KH KCl KClO KClO₃ KClO₄ KBr KBrO₃ KI KIO₃ KIO₄ KAt KCN KCNO KOCN KSCN
chalcogens	K₂O KOH K₂O₂ KO₂ KO₃ K₂S KHS K₂SO₃ KHSO₃ K₂SO₄ KHSO₄ KHSO₅ K₂S₂O₃ K₂S₂O₅ K₂S₂O₇ K₂S₂O₈ K₂Se K₂SeO₃ K₂SeO₄ K₂Te K₂TeO₃ K₂TeO₄ K₂Po
pnictogens	K₃N KNH₂ KN₃ KNO₂ KNO₃ K₃P KH₂PO₃ K₃PO₄ K₂HPO₄ KH₂PO₄ KPF₆ KAsO₂ K₃AsO₄ K₂HAsO₄ KH₂AsO₄
B, C group	B₄K₂O₇ K₂CO₃ KHCO₃ K₂SiO₃ K₂SiF₆ K₂Al₂O₄ K₂Al₂B₂O₇
transition metals	K₂PtCl₄ K₂Pt(CN)₄ K₂TiF₆ K₂PtCl₆ K₂ReCl₆ K ₂ReF ₆ KAsF₆ K₂ReBr₆ K ₂ReI ₆ K₂ZrF₆ K₄Fe(CN)₆ K₃Fe(CN)₆ K₃Fe(C₂O₄)₃ K₂FeO₄ K₂MnO₄ KMnO₄ K₃CrO₄ K₂CrO₄ K₃CrO₈ KCrO₃Cl K₂Cr₂O₇ K₂Cr₃O₁₀ K₂Cr₄O₁₃ K₄Mo₂Cl₈
organic	KHCO₂ KCH₃CO₂ KCF₃CO₂ K₂C₂O₄ KHC₂O₄ KC₁₂H₂₃O₂ KC₁₈H₃₅O₂ C₃H₂K₂O₄ C₄H₆KO₄ C₅H₇KO₄

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