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This latter cumene converts into cumene radical and feeds back into subsequent chain formations of cumene hydroperoxides. A pressure of 5 atm is used to ensure that the unstable peroxide is kept in liquid state. Cumene hydroperoxide undergoes a rearrangement reaction in an acidic medium (the Hock rearrangement) to give phenol and acetone. In ...
An excess of phenol is used to ensure full condensation and to limit the formation of byproducts, such as Dianin's compound. BPA is fairly cheap to produce, as the synthesis benefits from a high atom economy and large amounts of both starting materials are available from the cumene process. [7]
When 1-[14 C]-1-chlorobenzene was subjected to aqueous NaOH at 395 °C, ipso substitution product 1-[14 C]-phenol was formed in 54% yield, while cine substitution product 2-[14 C]-phenol was formed in 43% yield, indicating that an elimination-addition (benzyne) mechanism is predominant, with perhaps a small amount of product from addition ...
Cumene (isopropylbenzene) is an organic compound that contains a benzene ring with an isopropyl substituent. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C.
cumene – isopropylbenzene; a feedstock in the cumene process. phenol – hydroxybenzene; often made by the cumene process; acetone – dimethyl ketone; also often made by the cumene process; bisphenol A – a type of "double" phenol used in polymerization in epoxy resins and making a common type of polycarbonate
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Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone.In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate:
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