{{distinguish|text=the gas ozone}} {{Chembox | Verifiedfields = | Watchedfields = | verifiedrevid = | ImageFile = <div style="font-size: 150%">{{chem2|2(K+HSO5-)*K+HSO4-*(K+)2SO4(2-)}}</div> | ImageSize = | IUPACName = Potassium peroxysulfate-potassium sulfate-potassium bisulfate | OtherNames = | Section1 = {{Chembox Identifiers | CASNo = 70693-62-8 | CASNo1 = 37222-66-5 | EC_number = 274-778-7 | EC_number1 = 609-357-2 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = HL6A2XXU5D | PubChem = 15793144 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 26943821 | StdInChI=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 | StdInChIKey = HJKYXKSLRZKNSI-UHFFFAOYSA-I | SMILES = OS(=O)(=O)[O-].OS(=O)(=O)O[O-].OS(=O)(=O)O[O-].[O-]S(=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+] }} | Section2 = {{Chembox Properties | Formula = | K=5|H=3|S=4|O=18 | MolarMass = 614.76{{nbsp}}g/mol | Appearance = white solid | Solubility = 25-30 % (w/v) at 22 °C | Density = | MeltingPtC = 250 | MeltingPt_notes = (Decomposes) | BoilingPt = }} | Section7 = {{Chembox Hazards | ExternalSDS = ECHA<ref>{{cite web |title=Registration Dossier - ECHA |url=https://echa.europa.eu/registration-dossier/-/registered-dossier/15990/2/1 |website=echa.europa.eu |access-date=24 November 2025}}</ref> | MainHazards = Oxidant, corrosive | GHSPictograms = {{GHS05}} {{GHS07}} | GHSSignalWord = Danger | HPhrases = {{HPhrases|H302|H314|H412}} | PPhrases = {{PPhrases|P280|P301+P330+P331|P303+P361+P353|P305+P351+P338|P310|P273}} | FlashPt = | NFPA-H = 3 | NFPA-F = 0 | NFPA-R = 1 | NFPA-S = | NFPA_ref = <ref name=MPSmsds>{{cite web| author = ChemicalBook.com Staff | date = 2025-07-05 | title = Chemical Safety Data Sheet MSDS / SDS: potassium hydrogenperoxomonosulphate... CAS: 10058-23-8 | work = ChemicalBook.com | url = https://www.chemicalbook.com/msds/potassium-hydrogenperoxomonosulphate.htm | access-date = 3 November 2025}}</ref> }} | Section8 = {{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = | OtherFunction_label = | OtherCompounds = Potassium persulfate }} }} '''Oxone''' is the triple salt {{chem2|2KHSO5*KHSO4*K2SO4}}. For almost all applications, the active ingredient in this compound is potassium peroxymonosulfate, {{chem2|KHSO5}}.<ref name = ErosCrandall/> 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.<ref name = Ullmann1/> 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 H<sub>2</sub>O<sub>2</sub>.<ref>{{cite journal |last1=Ermer |first1=Otto |last2=Röbke |first2=Christof |title=Crystal Structure and Chemical Stabilization of the Triple Salt (KHSO<sub>5</sub>)<sub>2</sub>⋅KHSO<sub>4</sub>⋅K<sub>2</sub>SO<sub>4</sub> |journal=Helvetica Chimica Acta |date=2003 |volume=86 |issue=8 |pages=2908–2913 |doi=10.1002/hlca.200390238}}</ref>
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.<ref name = ErosCrandall>{{Cite book|title=Encyclopedia of Reagents for Organic Synthesis| editor = Paquette, Leo A. | last1=Crandall|first1=Jack K.|last2=Shi|first2=Yian|last3=Burke|first3=Christopher P.|last4=Buckley|first4=Benjamin R.|date = 14 September 2012|orig-date=2001|location = New York, NY | publisher=Wiley & Sons|isbn=9780470842898|language=en|doi=10.1002/047084289x.rp246.pub3 | url = https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rp246.pub3 | access-date = 3 November 2025 | url-access=subscription}}.</ref> An estimated 43-45% of it, by weight, of which 5.2% active oxygen is theoretically possible, and 4.7% was typically observed.<ref name=DuPontdeNemours>{{cite web | author = DuPont Staff | date = 2008 | title = DuPont™ Oxone® Monopersulfate Compound / General Technical Attributes | work = du Pont de Nemours | url = https://atamankimya.com/Assets/Documents/OXONE_Ataman_Kimya_20201212_185848.pdf | access-date = 3 November 2025 | location = Wilmington, DE | publisher = E.I. du Pont de Nemours & Co. | via = Ataman Kimya A.Ş.(AtamanKimya.com) | quote = }}</ref> In 2012, a review was reporting the {{chem2|KHSO5}} estimate to be "about 50% per mole" of triple salt.<ref name = ErosCrandall/>) 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 {{chem2|KHSO5·H2O}}.<ref name = ErosCrandall/><ref>{{cite journal | author = Travis, B. R.; Ciaramitaro, B. P. & Borhan, B. | date = 30 September 2002 | title = Preparation of Purified KHSO<sub>5</sub>·H<sub>2</sub>O and ''n''Bu<sub>4</sub>NHSO<sub>5</sub> from Oxone by Simple and Efficient Methods | journal = Eur. J. Org. Chem. | pages = 3429–3434 | url = https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/1099-0690%28200210%292002%3A20%3C3429%3A%3AAID-EJOC3429%3E3.0.CO%3B2-D | access-date = 3 November 2025 | url-access = subscription | doi = 10.1002/1099-0690(200210)2002:20<3429::AID-EJOC3429>3.0.CO;2-D}} The article has been made available by an author, at [https://www.chemistry.msu.edu/_assets/_files/borhan_research_group/publications/2002/EJOC.pdf this link].</ref>{{update after|2025|11|4}}
== 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.<ref name=Laxness>{{cite web | author = Laxness Staff | date = 2025 | title = Products and Brands / Brands / Oxone™ | work = Laxness.com | url = https://lanxess.com/en/products-and-brands/brands/oxone | access-date = 3 November 2025 | location = Cologne, Germany | publisher = LanXess AG | via = | quote = <small>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.</small>}}</ref> 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.<ref name = Ullmann1>{{cite encyclopedia | editor = Ley, Claudia | author=Jakob, Harald; Leininger, Stefan; Lehmann, Thomas; Jacobi, Sylvia & Gutewort, Sven | date = 15 July 2007 | chapter = Peroxo Compounds, Inorganic | title = Ullmann's Encyclopedia of Industrial Chemistry | location = Weinheim, Germany | publisher = Wiley-VCH | url = https://onlinelibrary.wiley.com/doi/10.1002/14356007.a19_177.pub2 | access-date = 3 November 2025 | url-access=subscription | doi = 10.1002/14356007.a19_177.pub2 | isbn=978-3-527-30673-2 }}</ref><ref name=Laxness/><ref>{{cite report | publisher=United States Environmental Protection Agency |date=2020-03-11 |title=Peroxy Compounds Human Health and Ecological Draft Risk Assessment DP 455445, 455446 |url=https://www.regulations.gov/search?filter=EPA-HQ-OPP-2017-0354-0006 |page=9-10 |access-date=2021-09-24}}</ref><ref>{{cite journal|first1=Stanisław |last1=Wacławek |first2=Holger V. |last2=Lutze |first3=Klaudiusz |last3= Grübel |first4=Vinod V.T. |last4=Padil |first5=Miroslav |last5=Černík |first6=Dionysios. D. |last6=Dionysiou |title=Peroxy Compounds Human Health and Ecological Draft Risk Assessment DP 455445, 455446 |journal = Chemical Engineering Journal |volume = 330 |pages = 44–62 |doi = 10.1016/j.cej.2017.07.132|date = 2017-12-15 }}</ref><ref name=AquaMag>{{cite web| author = PHTA Recreational Water Quality Committee | date = June 11, 2019 | title = Tech Notes: Potassium Monopersulfate | work = Aqua Magazine (AquaMagazine.com) | url = https://www.aquamagazine.com/service/article/15121932/tech-notes-potassium-monopersulfate | access-date = 3 November 2025 | location = Madison, WI | publisher = AB Media Inc. | quote = 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...}}</ref> 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).<ref name=Pool>{{cite book | author = TFP Staff (Anon.) | date = November 30, 2018 | title=Pool School | chapter = ABC's of Pool Water Chemistry | location = Unknown location | publisher=Trouble Free Pool (TFP) | chapter-url=https://books.google.com/books?id=WWBODwAAQBAJ&pg=PT4 |access-date=3 November 2025 | quote = 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, [https://www.troublefreepool.com/blog/2018/12/12/abcs-of-pool-water-chemistry/ linked here].</ref><ref>For a literature starting point for the FAS-DPD test, see {{cite journal | author = Moberg, Ludvig & Karlberg, Bo | date = 2000 | title = An Improved N,N′-diethyl-p-phenylenediamine (DPD) Method for the Determination of Free Chlorine Based on Multiple Wavelength Detection | journal = Analytica Chimica Acta | volume = 407 | issue = 1–2 | pages = 127–133 | issn = 0003-2670 | url = https://www.sciencedirect.com/science/article/pii/S0003267099007801 | access-date = 3 November 2025 | doi = 10.1016/S0003-2670(99)00780-1 | bibcode = 2000AcAC..407..127M | url-access = subscription }}{{primary source inline|date=November 2025}}</ref>{{better source|date=November 2025}}
=== Preparative chemistry=== Oxone is a versatile oxidant in organic chemistry.<ref>{{cite journal |last1=Hussain |first1=Hidayat |last2=Green |first2=Ivan R. |last3=Ahmed |first3=Ishtiaq |title=Journey Describing Applications of Oxone in Synthetic Chemistry |journal=Chemical Reviews |date=2013 |volume=113 |issue=5 |pages=3329–3371 |doi=10.1021/cr3004373 |pmid=23451713 |bibcode=2013ChRv..113.3329H }}{{cite journal |last1=Hussain |first1=Hidayat |last2=Green |first2=Ivan R. |last3=Ahmed |first3=Ishtiaq |title=Addition and Correction to Journey Describing Applications of Oxone in Synthetic Chemistry |journal=Chemical Reviews |date=2018 |volume=118 |issue=7 |pages=4114–4115 |doi=10.1021/acs.chemrev.8b00117 |pmid=29521500 }}</ref><ref name = ErosCrandall/><ref>{{cite book | author = Mundy, B.P.; Ellerd, M.G. & Favaloro Jr., F.G. | date = 2005 | title = Name Reactions and Reagents in Organic Synthesis | edition = 2nd | chapter = Oxone® | page = 828 | location = Hoboken, NJ | publisher = John Wiley & Sons | isbn = 9780471739869 | url = https://books.google.com/books?id=ahRrPTfeqPEC | access-date = 3 November 2025 | url-access = | doi = }}</ref> 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.<ref>{{March6th|page=1769}}</ref>
Oxone converts ketones to dioxiranes, which can be used for diverse oxidations in organic synthesis.<ref name=Adam>{{cite journal|title=Dioxirane Epoxidation of Alkenes|last1=Adam|first1=W.|last2=Saha-Moller|first2=C.|last3=Zhao|first3=C.-G.|journal=Org. React.|year=2004|volume=61|page=219|doi=10.1002/0471264180.or061.02 |isbn=978-0-471-26418-7 }}</ref> and in the oxidation of other unsaturated functionalities, heteroatoms, and even some alkane C-H bonds.<ref name=Adam2>{{cite journal|title=Dioxirane Oxidations of Compounds other than Alkenes|last1=Adam|first1=W.|last2=Zhao|first2=C.-G.|last3=Jakka|first3=K.|journal=Org. Reactions|year=2007|volume=69|page=1|doi=10.1002/0471264180.or069.01 |isbn=978-0-471-26418-7 }}</ref>
center|300px|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).<ref>{{cite journal |author1=Frigerio, M. |author2=Santagostino, M. |author3=Sputore, S. | title = A User-Friendly Entry to 2-Iodoxybenzoic Acid (IBX)| journal = J. Org. Chem. | year = 1999 | volume = 64 |issue=12 | pages = 4537–4538 | doi = 10.1021/jo9824596 |bibcode=1999JOrgC..64.4537F }}{{primary source inline|date=November 2025}}</ref>{{primary source inline|date=November 2025}}
center|300px|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).<ref name = ErosCrandall/>
Examples of preparative scale oxidatives of these types are the conversion of an acridine derivative to the corresponding acridine-N-oxide,<ref>{{OrgSynth |first1=Thomas W. |last1=Bell |first2=Young-Moon |last2=Cho |first3= Albert |last3=Firestone |first4=Karin |last4=Healy |first5=Jia |last5=Liu |first6=Richard |last6=Ludwig |first7=Scott D. |last7=Rothenberger | year= 1990| volume= 69|page=226|doi=10.15227/orgsyn.069.0226|title = 9-n-Butyl-1,2,3,4,5,6,7,8-Octahydroacridin-4-ol}}</ref> and the synthesis of fluoromethyl phenyl sulfone, a reagent used in the synthesis of fluoroalkenes.<ref>{{OrgSynth |year=1995|volume=72|page=209|doi= 10.15227/orgsyn.072.0209|first1=James R.|last1=McCarthy|first2=Donald P.|last2=Matthews|first3=John|last3=P. Paolini | title = Reaction of Sulfoxides with Diethylaminosulfur Trifluoride}}</ref>
center|350px center|270px
==Further reading== <!--For modern/contemporary sources not yet fully utilised with regard to the content that they could provide for the article.-->
* {{cite journal |last1=Wu |first1=Mingsong |last2=Xu |first2=Xinyang |last3=Xu |first3=Xun |date=November 2014 |title=Algicidal and Bactericidal Effect of Potassium Monopersulfate Compound on Eutrophic Water |journal=Applied Mechanics and Materials |volume=707 |page=259|doi=10.4028/www.scientific.net/AMM.707.259 |s2cid=98000605 | url = https://www.scientific.net/AMM.707.259 | access-date = 3 November 2025 | url-access = subscription}}{{Primary source inline|date=November 2025}}{{Better source|date=November 2025}}
* {{Cite book|title=Encyclopedia of Reagents for Organic Synthesis| editor = Paquette, Leo A. | last1=Crandall|first1=Jack K.|last2=Shi|first2=Yian|last3=Burke|first3=Christopher P.|last4=Buckley|first4=Benjamin R.|date = 14 September 2012|orig-date=2001|location = New York, NY | publisher=Wiley & Sons|isbn=9780470842898|language=en|doi=10.1002/047084289x.rp246.pub3 | url = https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rp246.pub3 | access-date = 3 November 2025 | url-access=subscription}} The original 1995 print publication of this chapter by Crandall was vol. 3, on pages 295ff.
* {{cite web | author = DuPont Staff | date = 2008 | title = DuPont™ Oxone® Monopersulfate Compound / General Technical Attributes | work = du Pont de Nemours | url = https://atamankimya.com/Assets/Documents/OXONE_Ataman_Kimya_20201212_185848.pdf | access-date = 3 November 2025 | location = Wilmington, DE | publisher = E.I. du Pont de Nemours & Co. | via = Ataman Kimya A.Ş.(AtamanKimya.com)}}
* {{cite encyclopedia | editor = Ley, Claudia | author=Jakob, Harald; Leininger, Stefan; Lehmann, Thomas; Jacobi, Sylvia & Gutewort, Sven | date = 15 July 2007 | chapter = Peroxo Compounds, Inorganic | title = Ullmann's Encyclopedia of Industrial Chemistry | location = Weinheim, Germany | publisher = Wiley-VCH | url = https://onlinelibrary.wiley.com/doi/10.1002/14356007.a19_177.pub2 | access-date = 3 November 2025 | url-access=subscription | doi = 10.1002/14356007.a19_177.pub2 | isbn=978-3-527-30673-2 }}
* {{cite book | author = Mundy, B.P.; Ellerd, M.G. & Favaloro Jr., F.G. | date = 2005 | title = Name Reactions and Reagents in Organic Synthesis | edition = 2nd | chapter = Oxone® | page = 828 | location = Hoboken, NJ | publisher = John Wiley & Sons | isbn = 9780471739869 | url = https://books.google.com/books?id=ahRrPTfeqPEC | access-date = 3 November 2025 | url-access = | doi = }}
* {{cite journal | author = Page, P.C.B.; Barros, D.; Buckley, B.R.; Ardakani, A. & Marples, B.A. | date = 2004 | title = Organocatalysis of Asymmetric Epoxidation Mediated by Iminium Salts under Nonaqueous Conditions | journal = J. Org. Chem. | volume = 69 | issue = 10 | pages = 3595–3597 | url = https://pubs.acs.org/doi/pdf/10.1021/jo035820j | access-date = 3 November 2025 | url-access = subscription | doi = 10.1021/jo035820j | pmid = 15132582 }} Presents an organic-soluble form of Oxone®, tetraphenylphosphonium peroxymonosulfate (Ph<sub>4</sub>PHSO<sub>5</sub>), and its successful deployment in the asymmetric epoxidation using peroxymonosulfate-generated oxaziridinium salts.
* {{cite journal | author = Travis, B. R.; Ciaramitaro, B. P. & Borhan, B. | date = 30 September 2002 | title = Preparation of Purified KHSO<sub>5</sub>·H<sub>2</sub>O and ''n''Bu<sub>4</sub>NHSO<sub>5</sub> from Oxone by Simple and Efficient Methods | journal = Eur. J. Org. Chem. | pages = 3429–3434 | url = https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/1099-0690%28200210%292002%3A20%3C3429%3A%3AAID-EJOC3429%3E3.0.CO%3B2-D | access-date = 3 November 2025 | url-access = subscription | doi = 10.1002/1099-0690(200210)2002:20<3429::AID-EJOC3429>3.0.CO;2-D}} The article has been made available by an author, at [https://www.chemistry.msu.edu/_assets/_files/borhan_research_group/publications/2002/EJOC.pdf this link].
== References == {{reflist}}
{{Potassium compounds}} {{Persulfates}}
Category:Persulfates Category:Potassium compounds Category:Oxidizing agents