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Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C 6 H 6 O 3 S.It is the simplest aromatic sulfonic acid.It forms white deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether.
In organic chemistry, the desulfonation reaction is the hydrolysis of sulfonic acids: [1] RC 6 H 4 SO 3 H + H 2 O → RC 6 H 5 + H 2 SO 4. The reaction applied to aryl and naphthylsulfonic acids. It is the reverse of sulfonation. [2] The temperature of desulfonation correlates with the ease of the sulfonation.
An early method for producing phenol involved the base hydrolysis of sodium benzenesulfonate, which can be generated readily from benzene. [15] C 6 H 5 SO 3 Na + NaOH → C 6 H 5 OH + Na 2 SO 3. The conditions for this reaction are harsh, however, requiring 'fused alkali' or molten sodium hydroxide at 350 °C for benzenesulfonic acid itself. [16]
Desulfonylation reactions are chemical reactions leading to the removal of a sulfonyl group from organic compounds.As the sulfonyl functional group is electron-withdrawing, [1] methods for cleaving the sulfur–carbon bonds of sulfones are typically reductive in nature.
In the most common route benzene is alkylated by long chain monoalkenes (e.g. dodecene) using hydrogen fluoride as a catalyst. [9] The purified dodecylbenzenes (and related derivatives) are then sulfonated with sulfur trioxide to give the sulfonic acid. [10] The sulfonic acid is subsequently neutralized with sodium hydroxide. [1]
In organic chemistry, aromatic sulfonation is an reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid (−SO 2 OH) group. Together with nitration and chlorination, aromatic sulfonation is a widely used electrophilic aromatic substitutions. [1] Aryl sulfonic acids are used as detergents, dye, and drugs.
Arylsulfonyl chlorides are made industrially in a two-step, one-pot reaction from an arene (in this case, benzene) and chlorosulfuric acid: [4] C 6 H 6 + HOSO 2 Cl → C 6 H 5 SO 3 H + HCl C 6 H 5 SO 3 H + HOSO 2 Cl → C 6 H 5 SO 2 Cl + H 2 SO 4. The intermediate benzenesulfonic acid can be chlorinated with thionyl chloride as well.
Some sultones are short-lived intermediates, used as strong alkylating agents to introduce a negatively charged sulfonate group. In the presence of water, they slowly hydrolyze to the hydroxy sulfonic acids. Sultone oximes are key intermediates in the synthesis of the anti-convulsant drug zonisamide. [4] Tisocromide is an example of a sultone.