Sulfonic / Sulfinic / Sulfamic acid derivatives
Sulfonic / Sulfinic / Sulfamic acid derivatives are a group of organosulfur compounds derived from sulfinic acid (R-SO2H), sulfonic acid (R-SO3H) or sulfamic acid (R-NH-SO3H). Aryl sulfonic acids are produced mainly by sulfonation (electrophilic aromatic substitution). Alkyl sulfonic acids can be obtained by the reaction of bisulfite (hydrogensulfite) with terminal alkenes or alkyl halides. Sulfonic acids are also formed by oxidation of thiols. Their main applications are associated with detergents and surfactants, dyes, acid catalysts, sulfa drugs (antibacterials) and lignosulfonates. Sulfinic acid derivative are often prepared in situ by acidification of the corresponding sulfinate salts, that are generated by reduction of sulfonyl chlorides. Alternatively, they can be obtained from the reaction of Grignard reagents with sulfur dioxide.
A commercially important sulfinic acid is thiourea dioxide, reductive bleach of textiles, which is prepared by the oxidation of thiourea with hydrogen peroxide. Sulfamic acid is produced industrially by treating urea with oleum. Sulfamic acid is mainly a precursor to sweet-tasting compounds (sodium cyclamate, acesulfame K). Sulfamates have been used in the design of many types of therapeutic agents. Sulfamic acid is preferable to hydrochloric acid in household use as a cleaning agent.
Sulfonic / Sulfinic / Sulfamic acid derivatives: