Hock process

In the Hock process (Figure 2), cumene (1, made by alkylating benzene with propylene)
is oxidized to cumene hydroperoxide (2), which is then cleaved to a mixture of phenol
(3) and acetone (4) by treating it with H2SO4.

The good news is that for every 10 kg of phenol produced, 6.2 kg of acetone is
coproduced. The bad news is that for every 10 kg of phenol produced, 6.2 kg of acetone
is coproduced. The process can be good or bad, depending on the petrochemical
market.

“Two-for-one” processes sound good in concept, but they only work commercially if the
markets for both products are changing at about the same rate. Otherwise, one product
will be in oversupply, which causes its price to fall and penalizes the economics of the
entire process.

https://www.acs.org/content/acs/en/pressroom/cutting-edge-chemistry/what-s-new-in-
phenol-production-.html

Cumene Route

The main method used to manufacture phenol since the 1960s has been through the oxidation of 1-
methylethylbenzene, commonly called cumene, which is made from benzene.

Starting with benzene and propene, the whole process includes three steps,
with the only other major product being propanone (acetone). Although there is
a market for propanone as a solvent, demand for phenol is rising faster than
demand for propanone.

This is one reason why alternative processes are being developed, combined
with the fact that it is a three-step process with a potentially explosive
intermediate. The possibility of converting excess propanone to propene for re-
use is being explored by some companies. Click here for more on the
cumene oxidation process.

http://www.greener-industry.org.uk/pages/phenol/4PhenolProdMethSum.htm