Cumene


Cumene is an organic compound that is based on an aromatic hydrocarbon with an aliphatic substitution. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C. Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals, primarily phenol and acetone.

Production

Commercial production of cumene is by Friedel–Crafts alkylation of benzene with propylene. Cumene producers account for approximately 20% of the global demand for benzene. The original route for manufacturing of cumene was by alkylation of benzene in the liquid phase using sulfuric acid as a catalyst, but because of the complicated neutralization and recycling steps required, together with corrosion problems, this process has been largely replaced. As an alternative, solid phosphoric acid supported on alumina was used as the catalyst.
Since the mid-1990s, commercial production has switched to zeolite-based catalysts. In this process, the efficiency of cumene production is generally 70-75%. The remaining components are primarily polyisopropyl benzenes. In 1976, an improved cumene process that uses aluminum chloride as a catalyst was developed. The overall conversion of cumene for this process can be as high as 90%.
The addition of two equivalents of propylene gives diisopropylbenzene. Using transalkylation, DIPB is comproportionated with benzene.

Safety

Cumene forms peroxides upon long exposure to air. Tests for peroxides are routinely conducted before heating or distilling.