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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.
Sodium benzenesulfonate is an organic compound with the formula C 6 H 5 SO 3 Na.It is white, water-soluble solid, It is produced by the neutralization benzenesulfonic acid with sodium hydroxide.
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]
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]
The compound is prepared by the chlorsulfonation of benzene: C 6 H 6 + 2SHO 3 SCl → C 6 H 5 SO 2 Cl + HCl + SO 3. Benzenesulfonic acid is an intermediate in this conversion. Diphenylsulfone is a side product. Benzenesulfonyl chloride can also be prepared by treating benzenesulfonate salts with phosphorus oxychloride. [2]
Sulfanilic acid can be produced by sulfonation of aniline with concentrated sulfuric acid. [5] This proceeds via phenylsulfamic acid; a zwitterion with a N-S bond. Eugen Bamberger originally proposed a mechanism involving a series of intramolecular rearrangements, with phenylsulfamic acid forming orthanilic acid, which rearranged to sulfanilic acid on heating.
Phenylsulfinic acid is an organosulfur compound with the formula C 6 H 5 SO 2 H. It is a colorless or white crystalline solid that is usually stored in the form of its sodium salt. In aqueous solution it is strongly acidic and is easily oxidized in air. Phenylsulfinic acid and its esters are chiral.
Chlorosulfuric acid is also an effective agent: C 6 H 6 + HSO 3 Cl → C 6 H 5 SO 3 H + HCl. In contrast to aromatic nitration and most other electrophilic aromatic substitutions this reaction is reversible. Sulfonation takes place in concentrated acidic conditions and desulfonation is the mode of action in a dilute hot aqueous acid.