| Potassium peroxymonosulfate | |
|---|---|
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| IUPAC name |
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| Other names | Caroat Oxone |
| Identifiers | |
| CAS number | , 37222-66-5 (triple salt, see text) |
| Properties | |
| Molecular formula | KHSO5 |
| Molar mass | 192.27 g/mol |
| Appearance | off-white powder |
| Hazards | |
| MSDS | Degussa Caroat MSDS |
| EU Index | Not listed |
| Main hazards | Oxidant |
| Related compounds | |
| Related compounds | Potassium persulfate |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Potassium peroxymonosulfate (also known as Oxone) is widely used as an oxidizing agent. It is the potassium salt of peroxymonosulfuric acid.
The potassium salt is marketed by two companies: Evonik (formerly Degussa) under the tradename Caroat and DuPont under the tradename Oxone, tradenames which are now part of standard chemistry vocabulary. It is a component of a triple salt with the formula 2KHSO5·KHSO4·K2SO4. The standard electrode potential for this compound is -1.44 V with a half reaction generating the hydrogen sulfate.
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- HSO4- + H2O → HSO5- + 2 H+ + 2 e-
Reactions
Oxone is a versatile oxidant. It oxidizes aldehydes to carboxylic acids; in the presence of alcoholic solvents, the esters may be obtained. Internal alkenes may be cleaved to two carboxylic acids, while terminal alkenes may be epoxidized. Thioethers give sulfones, tertiary amines give amine oxides, and phosphines give phosphine oxides.[1]
Illustrative of the oxidation power of this salt is the conversion of an acridine derivative to the corresponding acridine-N-oxide.[2]
It will also oxidize a thioether to a sulfone with 2 equivalents.[3] With one equivalent the reaction converting sulfide to sulfoxide is much faster than that of sulfoxide to sulfone, so the reaction can conveniently be stopped at that stage if so desired.
References
- ^ Benjamin R. Travis, Meenakshi Sivakumar, G. Olatunji Hollist, and Babak Borhan (2003). "Facile Oxidation of Aldehydes to Acids and Esters with Oxone". Organic Letters 5: 1031. doi:.
- ^ Thomas W. Bell, Young-Moon Cho, Albert Firestone, Karin Healy, Jia Liu, Richard Ludwig, and Scott D. Rothenberger (1993), "9-n-Butyl-1,2,3,4,5,6,7,8-Octahydroacridin-4-ol", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0087; Coll. Vol. 8: 87
- ^ James R. McCarthy, Donald P. Matthews, and John P. Paolini (1998), "Reaction of Sulfoxides with Diethylaminosulfur Trifluoride", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv9p0446; Coll. Vol. 9: 446
External links
- Applications
- DuPont Oxone Monopersulfate Compound Applications
- Potassium Monopersulfate – Article on precious metal extraction from distributor Green Controll
- Technical
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