hydroperoxid

Hydroperoxide, also known as hydroperoxid, refers to an organic compound that contains the hydroperoxy functional group (-OOH). The general formula is ROOH, where R is an alkyl, aryl, or other substituent. Hydroperoxides are a subset of peroxides and are key intermediates in oxidation chemistry.

Formation and occurrence: Hydroperoxides form by the addition of oxygen to hydrocarbons in the presence of radicals or catalysts, a process called autoxidation. They are important intermediates in lipid peroxidation in biological systems and can arise in various industrial oxidation processes. They can also be produced by oxidation of alcohols, alkenes, or through other synthetic routes.

Reactivity and properties: Most hydroperoxides are reactive and can be thermally unstable. They often decompose by homolysis to generate radicals, for example ROOH → RO• + OH•, a feature exploited in radical polymerization and certain oxidation reactions. They may also undergo acid- or metal-catalyzed rearrangements or be reduced to yield alcohols (ROH) or carbonyl compounds.

Industrial relevance: Cumene hydroperoxide is a major industrial hydroperoxide used to produce phenol and acetone via an acid-catalyzed cleavage. tert-Butyl hydroperoxide (TBHP) is widely used as an oxidant in organic synthesis and in polymerization and related processes.

Safety considerations: Hydroperoxides can be sensitive to heat, light, friction, or metal catalysts and may detonate when concentrated. They require careful handling, stabilized storage, and routine testing for peroxides in solvents to prevent hazardous buildup.