Question

Write short note on Industrial production of phenol by Dow process and Cumene process.

Answer 1

Answer:

The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was invented by Heinrich Hock in 1944 and independently by R. Ūdris and P. Sergeyev in 1942 (USSR).

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. In 2003, nearly 7 million tonnes of phenol was produced by the cumene process. In order for this process to be economical, there must also be demand for the acetone by-product as well as the

Steps of the process

Cumene is formed in the gas-phase Friedel–Crafts alkylation of benzene by propylene. 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 oxidized in air, which removes the tertiary benzylic hydrogen from cumene and hence forms a cumene radical:

The cumene radical then bonds with an oxygen molecule to give cumene peroxide radical, which in turn forms cumene hydroperoxide (C6H5C(CH3)2-O-O-H) by abstracting a 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.