Technical Description
Benzene and propylene are compressed together to a pressure of 30 standard atmospheres at 250 °C (482 °F) in presence of a catalytic Lewis acid. Phosphoric acid is often favored over aluminium halides. Cumene is formed in the gas-phase Friedel-Crafts alkylation of benzene by propylene:
Cumene is oxidized in air which removes the tertiary benzylic hydrogen from cumene and hence forms a cumene radical:
This cumene radical then bonds with an oxygen molecule to give cumene hydroperoxide radical, which in turn forms cumene hydroperoxide (C6H5C(CH3)2-O-O-H) by abstracting benzylic hydrogen from another cumene molecule. 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 is then hydrolysed in an acidic medium (the Hock rearrangement) to give phenol and acetone. In the first step, the terminal hydroperoxy oxygen atom is protonated. This is followed by a step in which the phenyl group migrates from the benzyl carbon to the adjacent oxygen and a water molecule is lost, producing a resonance stabilized tertiary carbocation. The concerted mechanism of this step is similar to the mechanisms of the Baeyer-Villiger oxidation and also the oxidation step of hydroboration-oxidation. In 2009, an acidified bentonite clay was proven to be a more economical catalyst than sulfuric acid as the acid medium.
As shown below, the resulting carbocation is then attacked by water, a proton is then transferred from the hydroxy oxygen to the ether oxygen, and finally the ion falls apart into phenol and acetone.
The products are extracted by distillation.
Read more about this topic: Cumene Process
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