Potassium peroxymonosulfate

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Potassium peroxymonosulfate

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Template:Longitem	KHSO5
Molar mass	152.2g/mol (614.76g/mol as triple salt)
Appearance	Off-white powder
NFPA 704 (fire diamond)	Template:NFPA 704 diamond
Template:Longitem	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 Template:Chem2, known as Oxone.

The standard electrode potential for potassium peroxymonosulfate is +1.81 V with a half reaction generating the hydrogen sulfate (pH = 0):

Template:Chem2

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 Template:Chem2. 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.

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, oxidizes organic contaminants in swimming pools, and cleans chips for the manufacture of microelectronics.

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. 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.

File:Acridine oxidation by oxone, standardized.png

Oxone oxidizes sulfides to sulfoxides and then to sulfones.

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. Dioxiranes are also oxidize other unsaturated functionality, heteroatoms, and alkane C-H bonds.

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).

Oxidation of 2-iodobenzoic acid to IBX

Oxidation of 2-iodobenzoic acid to IBX

Other uses

Oxone has been investigated for the delignification of wood.

Ammonium, sodium, and potassium salts of Template:Chem2 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.