Oxone

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Oxone
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Names
IUPAC name
Potassium peroxysulfate-potassium sulfate-potassium bisulfate
Identifiers
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3D model (JSmol)
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  • InChI=1S/5K.2H2O5S.2H2O4S/c;;;;;2*1-5-6(2,3)4;2*1-5(2,3)4/h;;;;;2*1H,(H,2,3,4);2*(H2,1,2,3,4)/q5*+1;;;;/p-5
    Key: HJKYXKSLRZKNSI-UHFFFAOYSA-I
  • OS(=O)(=O)[O-].OS(=O)(=O)O[O-].OS(=O)(=O)O[O-].[O-]S(=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+]
Properties
H3K5O18S4
Molar mass 614.76 g/mol
Appearance white solid
Melting point 250 °C (482 °F; 523 K) (Decomposes)
25-30 % (w/v) at 22 °C
Hazards
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[2]
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
0
1
Safety data sheet (SDS) ECHA[1]
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).

Template:Chembox Footer/trackingTemplate:Short description

Oxone is the triple salt Page Module:Chem2/styles.css has no content.2KHSO5·KHSO4·K2SO4. For almost all applications, the active ingredient in this compound is potassium peroxymonosulfate, Page Module:Chem2/styles.css has no content.KHSO5.[3] The triple salt has a longer shelf-life than potassium peroxymonosulfate, but releases the same peroxymonosulfate anion upon dissolution.

One advantage of oxone from an industrial point of view is that its dangerous goods classification tends to be Corrosive (Class 8) rather than Oxidising (Class 5). This makes it easier and cheaper to transport compared to other persulfate salts.

Synthesis and structure

The triple salt is produced via peroxysulfuric acid, which is generated in situ from sulfuric acid (oleum) and hydrogen peroxide and with potassium hydroxide.[4] X-ray crystallography confirms the triple salt formulation, revealing hydrogen-bonding network that entraps the persulfate anion. The O-O distance is 1.458(2) Å, as found in H2O2.[5]

The purity of Oxone can be determined by iodometric titration. Heavy metal salts catalyze the decomposition of the title compound, based on reporting on its triple salt formulation.[3] An estimated 43-45% of it, by weight, of which 5.2% active oxygen is theoretically possible, and 4.7% was typically observed.[6] In 2012, a review was reporting the Page Module:Chem2/styles.css has no content.KHSO5 estimate to be "about 50% per mole" of triple salt.[3]) The stability advantage notwithstanding (see following), methods were developed to deliver a forms of the title compound that required smaller amounts in reactions, and this was achieved on large scale in 2002 via preparations of purified Page Module:Chem2/styles.css has no content.KHSO5·H2O.[3][7]Template:Update inline span

Uses

Underlying the uses of Oxone is the highly positive oxidation potential for peroxymonosulfate, which is +1.81 V.

Cleaning

Oxone-type products are used for oxidative processes that result in decomposition of organic contaminants, and therefore in cleaning, whitening, and disinfection.[8] For instance, it can be used to whiten materials used in dental health practices, to clean materials in the manufacture of microelectronics, and decontaminate recreational water pools.[4][8][9][10][11] Use of formulations containing the title compound in pool water quality management can interfere with determinations of chlorination assay, using a standard ferrous ammonium sulfate, N,N′-diethyl-p-phenylenediamine (FAS-DPD) method, if added reagents and steps are not followed to neutralise the KMPS (potassium monopersulfate / peroxymonosulfate).[12][13]Template:Better source

Preparative chemistry

Oxone is a versatile oxidant in organic chemistry.[14][3][15] It oxidizes terminal alkenes to epoxides. It converts internal alkenes into two equivalents of carboxylic acid. Oxone convert aldehydes to carboxylic acids. When such reactions are conducted in the presence of alcoholic solvents, the corresponding esters may be obtained.[16]

Oxone converts ketones to dioxiranes, which can be used for diverse oxidations in organic synthesis.[17] and in the oxidation of other unsaturated functionalities, heteroatoms, and even some alkane C-H bonds.[18]

The Shi epoxidation
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).[19][non-primary source needed]

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

Peroxymonosulfate-driven conversions can be used with sulfides and selenides to prepare sulfones and selenones, with anilines and amino sugars to provide nitro compounds, oximes to provide nitro compounds (in aqueous buffered conditions) or to return the parent carbonyl compounds (in the presence of alumina, with microwave heating), primary and secondary amines to provide hydroxylamines (using adsorbed Oxone) or N-nitrosation products (in the presence of sodium nitrite), pyridines and tertiary amines to provide amine oxides, and phosphorus(III) compounds to provide phosphono-compounds largely retaining configuration at phosphorus (with comparable outcomes when a sulfur or selenium atom replaces the phosphorus(III) lone pair).[3]

Examples of preparative scale oxidatives of these types are the conversion of an acridine derivative to the corresponding acridine-N-oxide,[20] and the synthesis of fluoromethyl phenyl sulfone, a reagent used in the synthesis of fluoroalkenes.[21]

File:Acridine oxidation by oxone, standardized.png
File:Oxidation of an organic sulfide by oxone.png

Further reading

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."Registration Dossier - ECHA". echa.europa.eu. Retrieved 24 November 2025.
  2. ^ Page Module:Citation/CS1/styles.css has no content.ChemicalBook.com Staff (2025-07-05). "Chemical Safety Data Sheet MSDS / SDS: potassium hydrogenperoxomonosulphate... CAS: 10058-23-8". ChemicalBook.com. Retrieved 3 November 2025.
  3. ^ a b c d e f Page Module:Citation/CS1/styles.css has no content.Crandall, Jack K.; Shi, Yian; Burke, Christopher P.; Buckley, Benjamin R. (14 September 2012) [2001]. Paquette, Leo A. (ed.). Encyclopedia of Reagents for Organic Synthesis. New York, NY: Wiley & Sons. doi:10.1002/047084289x.rp246.pub3. ISBN 9780470842898. Retrieved 3 November 2025..
  4. ^ a b Page Module:Citation/CS1/styles.css has no content.Jakob, Harald; Leininger, Stefan; Lehmann, Thomas; Jacobi, Sylvia & Gutewort, Sven (15 July 2007). "Peroxo Compounds, Inorganic". In Ley, Claudia (ed.). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim, Germany: Wiley-VCH. doi:10.1002/14356007.a19_177.pub2. ISBN 978-3-527-30673-2. Retrieved 3 November 2025.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  5. ^ Page Module:Citation/CS1/styles.css has no content.Ermer, Otto; Röbke, Christof (2003). "Crystal Structure and Chemical Stabilization of the Triple Salt (KHSO5)2⋅KHSO4⋅K2SO4". Helvetica Chimica Acta. 86 (8): 2908–2913. doi:10.1002/hlca.200390238.
  6. ^ Page Module:Citation/CS1/styles.css has no content.DuPont Staff (2008). "DuPont™ Oxone® Monopersulfate Compound / General Technical Attributes" (PDF). du Pont de Nemours. Wilmington, DE: E.I. du Pont de Nemours & Co. Retrieved 3 November 2025 – via Ataman Kimya A.Ş.(AtamanKimya.com).
  7. ^ Page Module:Citation/CS1/styles.css has no content.Travis, B. R.; Ciaramitaro, B. P. & Borhan, B. (30 September 2002). "Preparation of Purified KHSO5·H2O and nBu4NHSO5 from Oxone by Simple and Efficient Methods". Eur. J. Org. Chem.: 3429–3434. doi:10.1002/1099-0690(200210)2002:20<3429::AID-EJOC3429>3.0.CO;2-D. Retrieved 3 November 2025.{{cite journal}}: CS1 maint: multiple names: authors list (link) The article has been made available by an author, at this link.
  8. ^ a b Page Module:Citation/CS1/styles.css has no content.Laxness Staff (2025). "Products and Brands / Brands / Oxone™". Laxness.com. Cologne, Germany: LanXess AG. Retrieved 3 November 2025. Oxone™ powder contains the active component potassium peroxymonosulfate (KHSO5), also known as potassium monopersulfate. The oxidizing power of Oxone™ is derived from this peracid chemistry, making it one of the strongest oxidants available on the market. / Oxone™ is used worldwide in a variety of consumer and industrial applications. / Applications / Pool and spa / Water treatment / Pulp and paper / Home care / Electronics / Denture cleaners / Odor control / Disinfection.
  9. ^ Page Module:Citation/CS1/styles.css has no content.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.
  10. ^ Page Module:Citation/CS1/styles.css has no content.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.
  11. ^ Page Module:Citation/CS1/styles.css has no content.PHTA Recreational Water Quality Committee (June 11, 2019). "Tech Notes: Potassium Monopersulfate". Aqua Magazine (AquaMagazine.com). Madison, WI: AB Media Inc. Retrieved 3 November 2025. Potassium Monopersulfate (monopersulfate, KMPS or MPS) is a white, granular, free-flowing peroxygen that provides powerful non-chlorine oxidation for a wide variety of uses. It is the active ingredient in most nonchlorine oxidizers used for pool and spa/hot tub oxidation. / Most non-chlorine oxidizers contain 45% of the active ingredient potassium monopersulfate, but blended compositions are also commercially available...
  12. ^ Page Module:Citation/CS1/styles.css has no content.TFP Staff (Anon.) (November 30, 2018). "ABC's of Pool Water Chemistry". Pool School. Unknown location: Trouble Free Pool (TFP). Retrieved 3 November 2025. Potassium monopersulfate (a common non-chlorine shock) will show up on [ferrous ammonium sulfate, N,N′-diethyl-p-phenylenediamine,] FAS-DPD chlorine tests as [combined chlorine,] CC. See also the same content at the organisation's website, linked here.
  13. ^ For a literature starting point for the FAS-DPD test, see Page Module:Citation/CS1/styles.css has no content.Moberg, Ludvig & Karlberg, Bo (2000). "An Improved N,N′-diethyl-p-phenylenediamine (DPD) Method for the Determination of Free Chlorine Based on Multiple Wavelength Detection". Analytica Chimica Acta. 407 (1–2): 127–133. Bibcode:2000AcAC..407..127M. doi:10.1016/S0003-2670(99)00780-1. ISSN 0003-2670. Retrieved 3 November 2025.{{cite journal}}: CS1 maint: multiple names: authors list (link)[non-primary source needed]
  14. ^ Page Module:Citation/CS1/styles.css has no content.Hussain, Hidayat; Green, Ivan R.; Ahmed, Ishtiaq (2013). "Journey Describing Applications of Oxone in Synthetic Chemistry". Chemical Reviews. 113 (5): 3329–3371. Bibcode:2013ChRv..113.3329H. doi:10.1021/cr3004373. PMID 23451713.Page Module:Citation/CS1/styles.css has no content.Hussain, Hidayat; Green, Ivan R.; Ahmed, Ishtiaq (2018). "Addition and Correction to Journey Describing Applications of Oxone in Synthetic Chemistry". Chemical Reviews. 118 (7): 4114–4115. doi:10.1021/acs.chemrev.8b00117. PMID 29521500.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Mundy, B.P.; Ellerd, M.G. & Favaloro Jr., F.G. (2005). "Oxone®". Name Reactions and Reagents in Organic Synthesis (2nd ed.). Hoboken, NJ: John Wiley & Sons. p. 828. ISBN 9780471739869. Retrieved 3 November 2025.{{cite book}}: CS1 maint: multiple names: authors list (link)
  16. ^ Script error: No such module "Template wrapper".
  17. ^ Page Module:Citation/CS1/styles.css has no content.Adam, W.; Saha-Moller, C.; Zhao, C.-G. (2004). "Dioxirane Epoxidation of Alkenes". Org. React. 61: 219. doi:10.1002/0471264180.or061.02. ISBN 978-0-471-26418-7.
  18. ^ Page Module:Citation/CS1/styles.css has no content.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. ISBN 978-0-471-26418-7.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Frigerio, M.; Santagostino, M.; Sputore, S. (1999). "A User-Friendly Entry to 2-Iodoxybenzoic Acid (IBX)". J. Org. Chem. 64 (12): 4537–4538. Bibcode:1999JOrgC..64.4537F. doi:10.1021/jo9824596.[non-primary source needed]
  20. ^ Page Module:Citation/CS1/styles.css has no content.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.
  21. ^ Page Module:Citation/CS1/styles.css has no content.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.

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