Synthesis of dinitrostilbenedisulfonic acid

Preparation of dinitrostilbenedisulfonic acid

Preparation of dinitrostilbenedisulfonic acid

Preparation of dinitrostilbenedisulfonic acid

100 grams of p-nitrotoluene are added carefully at 70°C. to a threefold quantity of oleum containing 25 % sulfur trioxide. The mixture heats up rapidly to 100-110° but should not be allowed to go higher or sudden charring may occur. When the addition of p-nitrotoluene is completed, the mixture is heated at 110-115° until a test sample in water has no trace of p-nitrotoluene odor. If the sulfonation is not complete in 30 minutes after the mixing, the sulfur trioxide is insufficient and 50 grams more of oleum is added dropwise. If necessary, another 50-gram portion is added after another half-hour. If the oleum actually contains 25 % of sulfur trioxide, however, these additional quantities should not be necessary. When the sulfonation is completed, the reaction mixture is cooled and poured onto 500 grams of ice with good mechanical stirring. The 2-methyl-5-nitrobenzene-1-sulfonic acid is isolated as the sodium salt (insoluble in saturated sodium chloride solution). The obtained 2-methyl-5-nitrobenzene-1-sulfonic acid sodium salt is dissolved at 50°C. in a solution of sodium carbonate in 500 ml. water. About 50 grams of sodium carbonate is required and diluted to 2 liters. The solution is heated to 50° in a water bath and over a period of 30 minutes, 160 grams of 35 % sodium hydroxide is added to the stirred solution, during which none of the sodium sulfonate should precipitate. A mixture of about 1700 grams of 5 % sodium hypochlorite solution and 300 grams of 35 % sodium hydroxide is then added slowly over a 3-hour period. The strength of the hypochlorite is first determined accurately by titration, and the quantity of solution corresponding to 85 grams of sodium hypochlorite is used. It must be remembered that hypochlorite solutions are stable only if they contain at least 5 % excess sodium hydroxide; this fact is especially important in the preparation of hypochlorite solutions. The temperature should not be allowed to rise above 60° or yellow dyes are formed. The mixture is allowed to stand at least 4 hours at 55°, during which time it should give a positive test for active gaseous chlorine with starchiodide paper. The solution is then cooled to 15° and allowed to stand for a day after 400 grams of common salt has been added. Sodium dinitrostilbenedisulfonate separates as a yellow, crystalline precipitate, and this is filtered off and washed with a small volume of salt solution. The yield of the crude salt is about 100 grams.

The fundamental processes of dye chemistry, by H. E. Fierz-David, 167-168, 1949

InChI

InChI=1S/C14H10N2O10S2/c17-15(18)11-5-3-9(13(7-11)27(21,22)23)1-2-10-4-6-12(16(19)20)8-14(10)28(24,25)26/h1-8H,(H,21,22,23)(H,24,25,26)/b2-1+

InChI Key

UETHPMGVZHBAFB-OWOJBTEDSA-N

Canonical SMILES

C1=CC(=C(C=C1[N+](=O)[O-])S(=O)(=O)O)C=CC2=C(C=C(C=C2)[N+](=O)[O-])S(=O)(=O)O

Isomeric SMILES

C1=CC(=C(C=C1[N+](=O)[O-])S(=O)(=O)O)/C=C/C2=C(C=C(C=C2)[N+](=O)[O-])S(=O)(=O)O

MeSH Synonyms

4,4′-dinitro-2,2′-stilbene disulfonate disodium salt, 4,4′-dinitro-2,2′-stilbenedisulfonic acid, 4,4′-dinitro-2,2′-stilbenedisulfonic acid, (E)-isomer, 4,4′-dinitro-2,2′-stilbenedisulfonic acid, (Z)-isomer, 4,4′-dinitro-2,2′-stilbenedisulfonic acid, disodium salt, 4,4′-dinitro-2,2′-stilbenedisulfonic acid, sodium salt, DNDS

Depositor-Supplied Synonyms

128-42-7, Dinitrostilbenedisulfonic acid, 6,6′-(Ethene-1,2-diyl)bis(3-nitrobenzenesulfonic acid), 4,4′-DINITRO-2,2′-STILBENEDISULFONIC ACID, 4,4′-Dinitrostilbene-2,2′-disulfonic acid, 4,4′-Dinitrostilbene-2,2′-disulphonic acid, CHEBI:36662, HSDB 5473, NSC1793, EINECS 204-885-6, NSC 1793, 2,2′-Stilbenedisulfonic acid, 4,4′-dinitro-, Kyselina 4,4′-dinitrostilben-2,2′-disulfonova [Czech], Benzenesulfonic acid, 2,2′-(1,2-ethenediyl)bis(5-nitro-, 2,2′-(E)-ethene-1,2-diylbis(5-nitrobenzenesulfonic acid), NSC163175, CHEBI:34663, 5-nitro-2-[(E)-2-(4-nitro-2-sulfo-phenyl)vinyl]benzenesulfonic acid, AC1NQZQA, 2, 4,4′-dinitro-, Kyselina 4,2′-disulfonova, SCHEMBL455775, CHEMBL2074646, MolPort-001-914-329, UETHPMGVZHBAFB-OWOJBTEDSA-N, NSC-1793, LMPK13090017, STK523135, ZINC12339546, AKOS000727588, AKOS024264465, AKOS025311567, 3709-43-1 (di-hydrochloride salt), MCULE-2376094885, 4,4′-Dinitro-2,2′-disulfonatostilbene, AJ-61144, AK116920, BAS 00093702, OR034488, OR211977, LS-146864, ST4014153, FT-0617095, FT-0649002, ST24044967, 4, 4′-Dinitro-2,2′-stilbenedisulfonic acid, 4, 4′-Dinitrostilbene-2,2′-disulfonic acid, 15883-59-7 (unspecified hydrochloride salt), C13706, Kyselina 4,4′-dinitrostilben-2,2′-disulfonova, 2, 2′-Stilbenedisulfonic acid, 4,4′-dinitro-, Kyselina 4,4′-dinitrostilben-2, 2′-disulfonova, (E)-4,4′-Dinitrostilbene-2,2′-disulfonic acid, 3B4-1766, 2,2′-ethene-1,2-diylbis(5-nitrobenzenesulfonic acid), I14-44027, 2,2′-(1,2-ethenediyl)bis(5-nitrobenzenesulfonic acid), Benzenesulfonic acid,2′-(1,2-ethenediyl)bis[5-nitro-, 2,2′-(1, 2-Ethenediyl)bis(5-nitrobenzenesulfonic acid), 2,2′-[(E)-Ethene-1,2-diyl]bis(5-nitrobenzenesulfonate), A0713/0033296, 2,2′-[(E)-1,2-Ethenediyl]bis[5-nitrobenzenesulfonic acid], 5,5′-dinitro-2,2′-(ethene-1,2-diyl)dibenzenesulfonic acid, Benzenesulfonic acid, {2,2′-(1,2-ethenediyl)bis[5-nitro-}, 5,5′-dinitro-2,2′-[(1E)-ethene-1,2-diyl]dibenzenesulfonic acid, 5-nitro-2-[(E)-2-(4-nitro-2-sulfophenyl)ethenyl]benzene-1-sulfonic acid, 5-nitro-2-[(E)-2-(4-nitro-2-sulfophenyl)ethenyl]benzenesulfonic acid, Benzenesulfonic acid, {2,2′-(1,2-ethenediyl)bis[5-nitro-,} disodium salt

Removed Synonyms

DNDS, 4,2′-disulfonic acid, 4,2′-stilbenedisulfonic acid, CID5282251, C022306, 4,4′-dinitro-2,2′-stilbene disulfonate disodium salt, 4,4′-dinitro-2,2′-stilbenedisulfonic acid, (E)-isomer, 4,4′-dinitro-2,2′-stilbenedisulfonic acid, (Z)-isomer, 4,4′-dinitro-2,2′-stilbenedisulfonic acid, sodium salt, 4,4′-Dinitro-2,2′-stilbenedisulfonic acid, disodium salt, 3709-43-1, DNS

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