tertbutylhydroperoxid

tert-Butylhydroperoxide, often abbreviated as TBHP, is an organoperoxide compound with the chemical formula C4H10O2. It is a colorless liquid and is typically sold as a solution in water or organic solvents. TBHP is a widely used oxidizing agent in organic synthesis and as a polymerization initiator.

In organic chemistry, TBHP is employed in various transformations. A notable application is the Sharpless epoxidation, a stereoselective method for converting allylic alcohols into chiral epoxides. It is also used in the oxidation of sulfides to sulfoxides and sulfones, and in the conversion of amines to nitro compounds. TBHP can act as a source of oxygen atoms, enabling the formation of new oxygen-carbon bonds. Its reactivity is often modulated by the presence of metal catalysts.

As a polymerization initiator, TBHP can initiate free radical polymerization processes. It decomposes upon heating or in the presence of initiators to generate free radicals, which then add to monomer molecules, starting the polymerization chain. This property makes it useful in the production of various polymers.

TBHP is a relatively stable hydroperoxide compared to some others, but it is still a strong oxidant and can be hazardous if not handled properly. It is important to store and use TBHP with appropriate safety precautions, avoiding contact with incompatible materials and sources of ignition. Its commercial availability in various concentrations and formulations facilitates its use in both laboratory and industrial settings.