sulfonic acid

sulfonic acid, any of a class of organic acids containing sulfur and having the general formula RSO₃H, in which R is an organic combining group. The sulfonic acids are among the most important of the organosulfur compounds; the free acids are widely used as catalysts in organic syntheses, while the salts and other derivatives form the basis of the manufacture of detergents, water-soluble dyes and catalysts, sulfonamide pharmaceuticals, and ion-exchange resins. Aromatic sulfonic acids are particularly useful as intermediates or starting materials in synthesis—for example, in the preparation of phenols. Sulfonic acid groups can greatly enhance the water solubility of compounds, as seen with the sulfonic acid derivative of triphenyl phosphine (TPPTS), P(C₆H₄-m-SO₃Na)₃. Metal complexes of this compound are used as homogeneous catalysts for the syntheses of organic compounds in two-phase systems (e.g., in a mixture of water and an organic solvent) in industry and in the laboratory.

Several sulfonic acids occur naturally—for example, the essential nutrient taurine (2-aminoethanesulfonic acid; NH₂CH₂CH₂SO₃H), the sulfobacins and other sulfonolipids (the biologically active products from bacterial cultures that contain 15- to 17-carbon chains attached to the carbon and nitrogen of 2-aminoethanesulfonic acid), and the echinosulfonic acid C (an α-hydroxysulfonic acid containing two brominated indole rings). The aliphatic sulfonic acids methanesulfonic acid and trifluoromethanesulfonic acid (triflic acid; CF₃SO₃H) are also commercially important reagents and catalysts. Triflic acid, one of the strongest known organic acids, is used as a polymerization catalyst and in fuel cells, in gasoline production, and in the synthesis of organic and organometallic compounds.

Aromatic sulfonic acids are obtained generally by treating aromatic compounds with concentrated sulfuric acid and added sulfur trioxide (“oleum”), the process being called sulfonation. Because the sulfonic acids are frequently used in the form of their sodium salts, sulfonation is usually followed by neutralization with sodium hydroxide or sodium carbonate. Such operations are conducted on a manufacturing scale in the preparation of the sodium salts of TPPTS (used in catalysts as described above), in the preparation of alkylated benzenesulfonic acids (used as synthetic detergents), and in the preparation of anthraquinonesulfonic acid (used in the manufacture of alizarin and other dyes).

Among the various methods used to prepare aliphatic sulfonic acids are the oxidation of other organosulfur compounds, the reaction of alkyl halides and metallic sulfites, and the reaction of organometallic compounds with amine complexes of sulfur trioxide (e.g., Me₃NSO₃). Triflic acid is manufactured by electrochemical fluorination of methanesulfonyl chloride or fluoride.