Potassium peroxymonosulfate
{{Redirect-distinguish2|Oxone|the gas ozone}}
{{Distinguish|Potassium persulfate}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477163234
| ImageFile = KHSO5.png
| ImageSize =
| IUPACName = Potassium peroxysulfate
| OtherNames = Caroat
potassium monopersulfate
MPS
KMPS
potassium caroate
non-chlorine shock{{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 }}
| Section1 = {{Chembox Identifiers
| InChI = 1S/K.H2O4S/c;1-4-5(2)3/h;1H,(H,2,3)/q+1;/p-1
| InChIKey1 = GZHFEBOLZPYNER-UHFFFAOYSA-M
| InChI2 = 1/K.H2O5S/c;1-5-6(2,3)4/h;1H,(H,2,3,4)/q+1;/p-1
| InChIKey2 = OKBMCNHOEMXPTM-REWHXWOFAJ
| CASNo = 10058-23-8
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo3_Ref = {{cascite|correct|CAS}}
| CASNo2 = 37222-66-5
| CASNo2_Comment = (triple salt)
| CASNo3 = 70693-62-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 040ZB27861
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = HL6A2XXU5D
| UNII1_Comment = (triple salt)
| PubChem = 11804954
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8053100
| SMILES = [K+].[O-]S(=O)(=O)OO
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/K.H2O5S/c;1-5-6(2,3)4/h;1H,(H,2,3,4)/q+1;/p-1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = OKBMCNHOEMXPTM-UHFFFAOYSA-M
}}
| Section2 = {{Chembox Properties
| Formula = KHSO5
| MolarMass = 152.2{{nbsp}}g/mol (614.76{{nbsp}}g/mol as triple salt)
| Appearance = Off-white powder
| Solubility = Decomposes
| Density =
| MeltingPt =
| BoilingPt =
}}
| Section7 = {{Chembox Hazards
| ExternalSDS = [https://www.fishersci.com/store/msds?partNumber=AC211360010&vendorId=VN00032119&countryCode=US Fisher Scientific SDS]
| MainHazards = Oxidant, corrosive
| FlashPt =
| NFPA-H = 3
| NFPA-F = 0
| NFPA-R = 1
| NFPA-S =
}}
| Section8 = {{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunction =
| OtherFunction_label =
| OtherCompounds = 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 {{chem2|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 ({{nowrap|pH {{=}} 0}}):{{cite journal|first1=M.|last1=Spiro|title=The standard potential of the peroxosulphate/sulphate couple|journal=Electrochimica Acta|issn=0013-4686|pages=313–314|volume=24|issue=3|doi=10.1016/0013-4686(79)85051-3|year=1979}}
:{{chem2|HSO5− + 2H+ + 2e− → HSO4− + 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 {{chem2|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.{{Cite book|title=Encyclopedia of Reagents for Organic Synthesis|last1=Crandall|first1=Jack K.|last2=Shi|first2=Yian|last3=Burke|first3=Christopher P.|last4=Buckley|first4=Benjamin R.|date=2001|publisher=John Wiley & Sons, Ltd|isbn=978-0-470-84289-8|language=en|doi=10.1002/047084289x.rp246.pub3}}
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,{{Ullmann | title = Peroxo Compounds, Inorganic |author=Harald Jakob |author2=Stefan Leininger |author3=Thomas Lehmann |author4=Sylvia Jacobi |author5=Sven Gutewort | doi = 10.1002/14356007.a19_177.pub2}} oxidizes organic contaminants in swimming pools,{{cite book |title=Pool School |publisher=Trouble Free Pool |page=PT4 |url=https://books.google.com/books?id=WWBODwAAQBAJ&pg=PT4 |access-date=November 30, 2018}} and cleans chips for the manufacture of microelectronics.{{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}}{{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 }}
== 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.{{cite journal | doi = 10.1021/ol0340078 |author1=Benjamin R. Travis |author2=Meenakshi Sivakumar |author3=G. Olatunji Hollist |author4=Babak Borhan |name-list-style=amp | title = Facile Oxidation of Aldehydes to Acids and Esters with Oxone | year = 2003 | journal = Organic Letters | volume = 5 | pages = 1031–4 | pmid = 12659566 | issue = 7}} 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.{{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}}
File:Acridine oxidation by oxone, standardized.png
Oxone oxidizes sulfides to sulfoxides and then to sulfones.{{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}}
File:Oxidation of an organic sulfide by oxone.png
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.{{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}} Dioxiranes are also oxidize other unsaturated functionality, heteroatoms, and alkane C-H bonds.{{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}}
File:Shi Epoxidation Scheme.png
Oxone is used in the production of some organic periodinanes, notably the oxidation of 2-iodobenzoic acid to 2-iodoxybenzoic acid (IBX).{{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}}
==Other uses==
Oxone has been investigated for the delignification of wood.{{cite journal |title=Treatment of softwood kraft pulps with peroxymonosulfate before oxygen delignification |last=Springer |first=E. L. |last2=McSweeny |first2=J. D. |journal=TAPPI Journal |year=1993 |volume=76 |issue=8 |pages=194–199 |url=http://www.tappi.org/Bookstore/Technical-Papers/Journal-Articles/TAPPI-JOURNAL/Archives/1993/August/Treatment-of-softwood-kraft-pulps-with-peroxymonosulfate-before-oxygen-delignification-TAPPI-JOURNA.aspx |issn=0734-1415 |access-date=2011-05-14 |archive-url=https://web.archive.org/web/20110929012348/http://www.tappi.org/Bookstore/Technical-Papers/Journal-Articles/TAPPI-JOURNAL/Archives/1993/August/Treatment-of-softwood-kraft-pulps-with-peroxymonosulfate-before-oxygen-delignification-TAPPI-JOURNA.aspx |archive-date=2011-09-29 |url-status=dead }}
Ammonium, sodium, and potassium salts of {{chem2|HSO5-}} 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
{{reflist}}
{{Potassium compounds}}
{{Persulfates}}