Hydroperoxiden

Hydroperoxides are a class of organic compounds that contain the hydroperoxy functional group (-OOH) bonded to a carbon atom. The general formula is ROOH, where R is an alkyl or aryl group. They are a subset of organic peroxides and occur in both industrial chemistry and biological systems.

In terms of structure and properties, the O–O bond in hydroperoxides is relatively weak, making ROOH compounds reactive and often unstable. Their stability depends on the nature of the substituent R. Hydroperoxides can decompose exothermically, and the rate of decomposition can be accelerated by heat, light, trace metals, or mechanical stress. Many hydroperoxides are liquids at room temperature, but stability varies with the specific molecule.

Industrial formation and sources include partial oxidation of hydrocarbons. A well-known example is cumene hydroperoxide, produced by oxidation of cumene and subsequently used to produce phenol and acetone in the cumene process. Another important class comprises organic hydroperoxides such as tert-butyl hydroperoxide, which are widely used as radical initiators in polymerization and various oxidation reactions. In laboratory settings, hydroperoxides are prepared and employed as reagents for initiating radical chains.

Reactivity and mechanism are dominated by radical processes. Hydroperoxides can decompose to generate radical species such as alkoxyl radicals (RO•) and hydroxy radicals (HO•) under thermal or catalytic conditions, enabling polymerization or oxidation of substrates. In biology, lipid hydroperoxides arise from lipid peroxidation and can propagate oxidative damage, later breaking down into reactive aldehydes and other products.

Safety and handling are important considerations. Many hydroperoxides are shock-sensitive or thermally unstable and can pose explosion or fire hazards. They require careful storage, temperature control, and incompatibility precautions to minimize accidental decomposition.

Examples include tert-butyl hydroperoxide and cumene hydroperoxide.