Cumene process
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Cumene process is an industrial process for developing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process.
This process converts two relatively cheap starting materials, benzene and propylene, into two more valuable ones, phenol and acetone. Other reactants required are oxygen from air and small amounts of a radical initiator. Most of the worldwide production of phenol and acetone is now based on this method.
The overall chemical process is summarised below.
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[edit] 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 to give phenol and acetone. In the first step, the terminal hydorperoxy 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[1] and also the oxidation step of hydroboration-oxidation.[2]
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.
[edit] References
- ^ Streitwieser, A; Heathcock, C.H. (1992). "30". Introduction to Organic Chemistry. Kosower, E.M. (4th ed.). New York: MacMillan. pp. 1018. ISBN 0-02-418170-6.
- ^ K.P.C., Vollhardt; N.E. Schore (2003). "22". Organic Chemistry: Structure and Function (4th ed.). New York: Freeman. pp. 988. ISBN 0716743744.
[edit] See also
- Chemical synthesis
- Dow process
- Friedel Crafts alkylation
- Baeyer-Villiger oxidation
- Concerted reaction
- Raschig process (also produces phenol)
[edit] External links
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