Synthesis of 3-nitrobenzenesulfonic acid (m-nitrobenzenesulfonic acid; benzenesulfonic acid)

Preparation of 3-nitrobenzenesulfonic acid

Preparation of 3-nitrobenzenesulfonic acid (m-nitrobenzenesulfonic acid; benzenesulfonic acid)

Preparation of 3-nitrobenzenesulfonic acid (m-nitrobenzenesulfonic acid; benzenesulfonic acid)

123 g of nitrobenzene are added into 375 g of oleum (25 % free sulfur trioxide) at 70° C. The mixture warms up rapidly to 100-110° C, but must not be allowed to rise any higher. When all nitrobenzene has been added, the mixture is heated at 110-115° C until a test portion poured into water no longer gives any odor of nitrobenzene. If complete sulfonation has not occurred within half an hour, then insufficient amount of oleum has been used. In this case 50 g more oleum are added drop by drop, and if necessary a further quantity after half an hour more. The reaction mixture is then allowed to cool, and is poured on to 500 g ice with good mechanical stirring. The nitrobenzene sulfonic acid goes completely into solution with the exception of a small proportion of side product – bis(3-nitrophenyl) sulfone. 200 g of sodium chloride, in small quantities at a time, are added with continuous stirring. The sodium salt of 3-nitrobenzenesulfonic acid separates out as a thick paste, and stirring must be continued for some time, until the mass again liquefies. After about 10 hours the solid is filtered yielding the crude sodium 3-nitrobenzenesulfonate, which may be obtained purified by recrystallization from water. 3-nitrobenzenesulfonic acid is obtained by neutralizing sodium 3-nitrobenzenesulfonate with stereochemical amount of dilute sulfuric acid.

The fundamental process of dye chemistry, by  H. E. Fierz-David, 41-42, 1921

InChI

InChI=1S/C6H5NO5S/c8-7(9)5-2-1-3-6(4-5)13(10,11)12/h1-4H,(H,10,11,12)

InChI Key

ONMOULMPIIOVTQ-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC(=C1)S(=O)(=O)O)[N+](=O)[O-]

MeSH Synonyms

3-nitrobenzenesulfonic acid, o-nitrobenzenesulfonic acid, ortho-nitrobenzenesulfonic acid

Depositor-Supplied Synonyms

3-NITROBENZENESULFONIC ACID, 98-47-5, m-Nitrobenzenesulfonic acid, Benzenesulfonic acid, 3-nitro-, m-Nitrobenzensulfonic acid, 3-Nitrobenzenesulphonic acid, Benzenesulfonic acid, m-nitro-, 3-Nitrophenylsulfonic acid, m-nitrobenzene sulfonic acid, Kyselina 3-nitrobenzensulfonova, CCRIS 3131, 3-nitrobenzene-1-sulfonic acid, Kyselina nitrobenzen-m-sulfonova, ONMOULMPIIOVTQ-UHFFFAOYSA-N, EINECS 202-671-7, BRN 0647983, Kyselina 3-nitrobenzensulfonova [Czech], Kyselina nitrobenzen-m-sulfonova [Czech], AC1L1ONA, AC1Q6WH7, 3-Nitro-benzenesulfonic acid, SCHEMBL33350, CHEMBL3306825, CTK8B7931, MolPort-001-779-829, ANW-58980, AR-1F4647, AKOS015833330, AJ-30454, AK-53477, AM101767, KB-32969, LS-32035, AB1009814, DB-057729, KB-203159, TR-030327, FT-0631509, N0138, ST24042387, 4-11-00-00179 (Beilstein Handbook Reference), 3B3-024368

Removed Synonyms

null, CID7387, 6091-01-6

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