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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 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]
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]
reduction of 1-nitroonaphthalene-8-sulfonic acid, precursor to C.I. Acid Blue 113 Notes: Peri-acid dehydrates to the sultam . Via the Bucherer reaction , heating periacid with anilinium salts gives the N-phenyl derivative, precursor to Acid Blue 113.
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.
Sodium phenoxide can also be produced by the "alkaline fusion" of benzenesulfonic acid, whereby the sulfonate groups are displaced by hydroxide: C 6 H 5 SO 3 Na + 2 NaOH → C 6 H 5 OH + Na 2 SO 3. This route once was the principal industrial route to phenol. [citation needed]
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.
This compound and some related alkylbenzenes are produced industrially by alkylation of benzene with the corresponding alkenes in the presence of hydrogen fluoride or related acid catalysts. The resulting linear alkylbenzene compounds are sulfonated to give the corresponding sulfonic acids. This sulfonation can be highly specific to place the ...