ROOH

ROOH is a generic notation used in organic chemistry to denote hydroperoxides, a class of organic peroxides. The formula is R-O-O-H, in which R is an alkyl or aryl group. Hydroperoxides are typically reactive intermediates and, depending on the substituent, may range from isolable compounds to unstable species that exist only in solution.

Formation and occurrence: Hydroperoxides form by autoxidation of hydrocarbons in the presence of oxygen, commonly via radical chain mechanisms. Lipid hydroperoxides (LOOH) arise from peroxidation of polyunsaturated fatty acids in biological membranes. Industrially, hydroperoxides such as cumene hydroperoxide are produced by air oxidation of the corresponding hydrocarbon and are used as precursors to phenol and acetone in the cumene process.

Properties: ROOH species are generally less stable than many other organic compounds and can be sensitive to heat, light, metal contaminants, and mechanical shock. Their decomposition is exothermic and can generate radical species, including alkoxyl and hydroxyl radicals, which can propagate further reactions and pose handling hazards. Stability varies with the nature of R; tertiary hydroperoxides, in particular, can be highly shock-sensitive.

Reactions and applications: In synthesis, hydroperoxides act as oxidants or radical initiators and can be reduced to the corresponding alcohols or further transformed into other oxidation products. Cumene hydroperoxide is a notable industrial example, cleaved to phenol and acetone. In polymer chemistry, ROOH derivatives serve as initiators for radical polymerization and related processes.

Safety: Handling ROOH requires caution due to potential explosive hazards and their sensitivity to heat, friction, and metal contaminants. They are typically stored at controlled temperatures, away from light and sources of shock, in compatible containers.