Sulfonic acid
organic compound with the structure R−S(=O)₂−OH

In organic chemistry, sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.
Preparation
Most sulfonic acids and, indirectly, most sulfonate salts are produced by treatment of organic compounds with sulfur trioxide. One 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 is the nucleophile. The reaction is an example of electrophilic aromatic substitution.
In a related process, terminal alkenes react with sulfur trioxide to give α-olefin sulfonic acids (and hydroxysulfonic acid):
RCH2CH=CH2 + SO3 → RCH=CHCH2SO3H
Likewise, carboxylic acids react with sulfur trioxide to give the sulfonic acids.
A third large-scale industrial process starts simply with saturated hydrocarbons. Sulfoxidation, similar to the Reed reaction, irradiates a mixture of alkanes, sulfur dioxide and oxygen:
RH + SO2 + 1/2 O2 → RSO3H
UV (or higher-energy) light is usually necessary, but titanium dioxide catalyzes the reaction with visible light.
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