- Sulfonic acid
Sulfonic acid (or sulphonic acid) usually refers to a member of the class of organosulfur compounds with the general formula RS(=O)2–OH, where R is an alkyl or aryl. The formal part of acid, HS(=O)2–OH, are formally derivatives of the "parent" inorganic compound with the formula HSO2(OH).
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
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
Sulfonic acids are much stronger acids than the corresponding carboxylic acids. p-Toluenesulfonic acid, with a pKa of -2.8, is about a million times stronger acid than benzoic acid, with a pKa of 4.2. Similarly, methanesulfonic acid, pKa = -1.9, is also about one million times stronger acid than acetic acid. Because of their polarity, sulfonic acids tend to be crystalline solids. They are also usually colourless and nonoxidizing, which is convenient. Because of their high acidity, sulfonic acids are often soluble in water or exhibit detergent-like properties.
The structure of sulfonic acids is illustrated by the prototype, methanesulfonic acid. The sulfonic acid group, RSO2(OH features a tetrahedral sulfur centre, meaning that sulfur is at the center of four atoms: three oxygens and onecarbon. The overall geometry of the sulfur centre is reminiscent of the shape of sulfuric acid.
Although both alkyl and aryl sulfonic acids are known, most of the applications are associated with the aromatic derivatives.
Detergents and surfactants
Detergents and surfactants are molecules that combine highly nonpolar and highly polar groups. Traditionally, soaps are the popular surfactants, being derived from fatty acids. Since the mid-20th century, the usage of sulfonic acids has surpassed soap in advanced societies. For example, an estimated 2 billion kilograms of alkylbenzenesulfonates are produced annually for diverse purposes. Lignin sulfonates, produced by sulfonation of lignin are components of drilling fluids and additives in certain kinds of concrete.
Many if not most of the anthroquinone dyes are produced or processed via sulfonation. Sulfonic acids tend to bind tightly to proteins and carbohydrates. Most "washable" dyes are sulfonic acids (or have the functional sulfonyl group in them) for this reason. p-Cresidinesulfonic acid is used to make food dyes.
Being strong acids, sulfonic acids are also used as catalysts. The simplest examples are methanesulfonic acid, CH3SO2OH and p-toluenesulfonic acid, which are regularly used in organic chemistry as acids that are lipophilic (soluble in organic solvents). Polymeric sulfonic acids are also useful. Dowex resin are sulfonic acid derivatives of polystyrene and is used as catalysts and for ion exchange (water softening).Nafion, a fluorinated polymeric sulfonic acid is a component of proton exchange membranes in fuel cells.
Antibacterial drugs sulfa drugs are produced from sulfonic acids.
Sulfonic acids can be converted to esters. This class of organic compounds has the general formula R-SO2-OR. Sulfonic esters such as methyl triflate are considered good alkylating agents in organic synthesis. Such sulfonate esters are often prepared by alcoholysis of the sulfonyl chlorides:
- RSO2Cl + R'OH → RSO2OR' + HCl
Sulfonyl halide groups occur when a sulfonyl functional group is singly bonded to a halogen atom. They have the general formula R-SO2-X where X is a halide, almost invariably chloride. They are produced by chlorination of sulfonic acids using thionyl chloride and related reagents.
Although the C-SO3H bond is strong, the (aryl)C-SO3 bond can be cleaved by certain nucleophiles. Of historic and continuing significance is the α-sulfonation of anthroquinone followed by displacement of the sulfonate group by other nucleophiles, which cannot be installed directly. An early method for producing phenol involved the base hydrolysis of sodium benzenesulfonate, which can be generated readily from benzene.
- C6H5SO3Na + 2 NaOH → C6H5ONa + Na2SO3 + H2O
Sulfonic acid derivatives are generally not derived from natural precursors and tend to biodegrade slowly. Some, such as perfluorooctane sulfonic acid, have been detected in the serum of humans. This should be not surprising as all organic fluorine compounds have extreme stability, and low to zero biodegradability. Many are intended to withstand harshest chemical conditions, for example teflon.
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- J.A. Titus, R. Haugland, S.O. Sharrow and D.M. Segal, Texas red, a hydrophilic, red-emitting fluorophore for use with fluorescein in dual parameter flow microfluorometric and fluorescence microscopic studies. J. Immunol. Methods 50 (1982), pp. 193–204. doi:10.1016/0022-1759(82)90225-3 PMID 6806389
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See also Chemical classification Hydrogen compounds
H3AsO3 · H3AsO4 · HAt · HSO3F · HBF4 · HBr · HBrO · HBrO2 · HBrO3 · HBrO4 · HCl · HClO · HClO2 · HClO3 · HClO4 · HCN · HCNO · H2CrO4/H2Cr2O7 · H2CO3 · H2CS3 · HF · HFO · HI · HIO · HNC · HNCO · HNO · HNO3 · H2N2O2 · HNO5S · H3NSO3 · H2O · H2O2 · H2O3 · H3PO2 · H3PO3 · H3PO4 · H4P2O7 · H5P3O10 · H2PtCl6 · H2S · H2Se · H2SeO3 · H2SeO4 · H4SiO4 · H2SiF6 · H2SO3 · H2SO4 · H2SO5 · H2S2O3 · H2S2O6 · H2S2O7 · H2S2O8 · CF3SO3H · H2Te · H2TeO3 · H6TeO6 · H4TiO4 · H2Po · H3VO4 · HCo(CO)4
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sulfonic acid — n. any of numerous organic acids containing the sulfonic group SO3H, derived from sulfuric acid by the replacement of an OH group: used in the manufacture of dyes, drugs, phenols, etc … English World dictionary
sulfonic acid — Chem. any of a large group of organic compounds of the structure RSO2OH, which are strong acids that give neutral sodium salts: used in the synthesis of phenols, dyes, and other substances. [1870 75] * * * ▪ chemical compound sulfonic also… … Universalium
sulfonic acid — Any of the compounds in which a hydrogen atom of a CH group is replaced by the s. group, –SO3H; general formula : R–SO3H. SYN: sulfoacid (2). * * * sulfonic acid n any of numerous acids that contain the SO3H group and may be derived from sulfuric … Medical dictionary
sulfonic acid — sulfonrūgštis statusas T sritis chemija formulė RSO₃H atitikmenys: angl. sulfonic acid rus. сульфокислота; сульфоновая кислота … Chemijos terminų aiškinamasis žodynas
sulfonic acid — noun an acid derived from sulphuric acid • Syn: ↑sulphonic acid • Hypernyms: ↑acid … Useful english dictionary
sulfonic acid — noun Date: 1873 any of numerous acids that contain the SO3H group and may be derived from sulfuric acid by replacement of a hydroxyl group by either an inorganic anion or a monovalent organic group … New Collegiate Dictionary
sulfonic acid — noun a) a strong inorganic acid, HSOOH b) the univalent functional group SOOH See Also: sulfonate … Wiktionary
sulfonic acid — sulfon′ic ac′id n. chem. any of a large group of organic compounds of the structure RSO2Oused in the synthesis of phenols, dyes, and other substances • Etymology: 1870–75 … From formal English to slang
Phenylbenzimidazole sulfonic acid — chembox new ImageFile=Phenylbenzimidazole sulfonic acid.png ImageSize= IUPACName=2 phenyl 3H benzimidazole 5 sulfonic acid OtherNames= Section1=Chembox Identifiers CASNo= PubChem= 33919 SMILES=C1=CC=C(C=C1)C2=NC3=C(N2)C=C(C=C3)S(=O)(=O)O Section2 … Wikipedia
phenylbenzimidazole sulfonic acid — phen·yl·ben·zi·mid·a·zole sul·fon·ic ac·id (fen″əl ben″zĭ midґə zōl sul fonґik) ensulizole … Medical dictionary