Sulfonic Acids - Preparation

Preparation

Sulfonic acid is produced by the process of sulfonation. Usually the sulfonating agent is sulfur trioxide. A particularly large scale application of this method is the production of alkylbenzenesulfonic acids:

RC6H5 + SO3 → RC6H4SO3H

In this reaction, sulfur trioxide is an electrophile and the arene undergoes electrophilic aromatic substitution.

Thiols can be oxidized to sulfonic acids:

RSH + 3/2 O2 → RSO3H

Certain sulfonic acids, such as perfluorooctanesulfonic acid are prepared by electrophilic fluorination of preformed sulfonic acids. The net conversion can be represented simplistically:

C8H17SO3H + 17 F2 → C8F17SO3H + 17 HF

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