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Chemistry · Ch 11 — Hydroxy Compounds and Ethers

Preparation of Phenol from Benzene Sulphonic Acid

11.13.2

Preparation of Phenol from Benzene Sulphonic Acid

Benzene is sulphonated with oleum (fuming sulphuric acid, H2SO4 with dissolved SO3) to give benzenesulphonic acid; heating this with molten (solid, not aqueous) NaOH at 623 K gives sodium phenoxide, a process called alkali fusion, which is then acidified with dilute HCl to liberate phenol: C6H5-SO3H + NaOH (623 K, fused) gives C6H5-ONa, then + HCl gives C6H5-OH. This was historically the earliest industrial route to phenol, later superseded by …