Potassium peroxymonosulfate is widely used as an

oxidizing agent An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxi ...

. It is the

potassium Potassium is the chemical element with the symbol K (from Neo-Latin ''kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmosph ...

salt Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quant ...

of peroxymonosulfuric acid. Usually potassium peroxymonosulfate refers to the triple salt known as oxone. The

standard electrode potential In electrochemistry, standard electrode potential E^\ominus, or E^\ominus_, is a measure of the reducing power of any element or compound. The IUPAC "Gold Book" defines it as: ''"the value of the standard emf (electromotive force) of a cell in wh ...

for potassium peroxymonosulfate is +1.81 V with a

half reaction A half reaction (or half-cell reaction) is either the oxidation or reduction reaction component of a redox reaction. A half reaction is obtained by considering the change in oxidation states of individual substances involved in the redox reaction. ...

generating the hydrogen sulfate (): ::HSO₅⁻ + 2 H⁺ + 2 e⁻ → 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 2KHSO₅·KHSO₄·K₂SO₄. Oxone has a longer shelflife than does potassium peroxymonosulfate. A white, water-soluble solid, oxone loses <1% of its oxidizing power per month.

Production

Oxone is produced from peroxysulfuric acid, which is generated in situ by combining oleum and

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%� ...

. Careful neutralization of this solution with potassium hydroxide allows the crystallization of the triple salt.

Uses:lab use +chemistry research

Cleaning

Oxone is used widely for cleaning. It whitens dentures, disinfects swimming pools, and cleans chips for the manufacture of microelectronics.

Organic chemistry

Oxone is a versatile oxidant in organic synthesis. It oxidizes

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...

s to carboxylic acids; in the presence of alcoholic solvents, the

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

s may be obtained. Internal

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

s may be cleaved to two carboxylic acids (see below), while terminal alkenes may be epoxidized. Sulfides give

sulfone In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl () functional group attached to two carbon atoms. The central hexavalent sulfur atom is double-bonded to each of two oxygen atoms and has a single bond to each of ...

s, tertiary

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen Hydrogen is the chemical element wi ...

s give

amine oxide In chemistry, an amine oxide, also known as an amine ''N''-oxide or simply ''N''-oxide, is a chemical compound that contains the functional group , a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substituent-grou ...

s, and

phosphine Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...

s give phosphine oxides. Further illustrative of the oxidative power of this salt is the conversion of an

acridine Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups re ...

derivative to the corresponding acridine-

N-oxide In chemistry, an amine oxide, also known as an amine ''N''-oxide or simply ''N''-oxide, is a chemical compound that contains the functional group , a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substituent-grou ...

Acridine oxidation by oxone, standardized

Oxone oxidizes sulfides to sulfoxides and then to

Oxidation of an organic sulfide by oxone

Oxone converts ketones to

dioxirane In chemistry, dioxirane is a compound with formula , whose molecule consists of a ring with one carbon and two oxygen atoms, and two hydrogen atoms attached to the carbon. It is a heterocyclic compound, the smallest cyclic organic peroxide. Th ...

s. The synthesis of

dimethyldioxirane Dimethyldioxirane (DMDO), also referred to as Murray's reagent in reference to Robert W. Murray, is a dioxirane derived from acetone and can be considered as a monomer of acetone peroxide. It is a powerful yet selective oxidizing agent which fi ...

(DMDO) from

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

is representative. Dioxiranes are versatile oxidising agents and may be used for the

epoxidation In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale ...

of olefins. In particular, if the starting ketone is

chiral Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from i ...

then the epoxide may be generated enantioselectively, which forms the basis of the

Shi epoxidation The Shi epoxidation is a chemical reaction described as the asymmetric epoxidation of alkenes with oxone (potassium peroxymonosulfate) and a fructose-derived catalyst (1). This reaction is thought to proceed via a dioxirane intermediate, generated ...

References

{{Reflist Persulfates Potassium compounds Oxidizing agents