Potassium peroxymonosulfate

"Oxone" redirects here. Not to be confused with the gas ozone.

Not to be confused with Potassium persulfate.

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.

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)	Fisher Scientific SDS
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

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]

The Shi epoxidation

Oxone is used in the production of some organic periodinanes, notably the oxidation of 2-iodobenzoic acid to 2-iodoxybenzoic acid (IBX).^[14]

Oxidation of 2-iodobenzoic acid to IBX

Other uses

Oxone has been investigated for the delignification of wood.^[15]

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

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 from the original (PDF) on 2014-08-15. Retrieved 2012-01-26.
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. 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 978-3-527-30673-2.
6. Pool School. Trouble Free Pool. p. PT4. Retrieved November 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. Retrieved 2021-09-24.
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 from the original on 2011-09-29. Retrieved 2011-05-14.