Synthesis of sodium anthraquinone-2-sulfonate

Preparation of sodium anthraquinone-2-sulfonate

Preparation of sodium anthraquinone-2-sulfonate

Preparation of sodium anthraquinone-2-sulfonate

100 g dry, finely divided anthraquinone are added cautiously to 150 g oleum containing 25% sulfur trioxide, with continuous stirring, the temperature being kept at 25—30°C. The temperature is then raised to 120°C during 4 hours, and then to 140°C during a further 2 hours, using an oil bath. The vessel must be kept closed to prevent loss of sulfur trioxide. After cooling, the obtained mixture is poured into 3 litres of water (caution!) and the 25—40 g of unchanged anthraquinone is removed by filtration. Calcium carbonate is added to the filtrate until completely neutralized, and the calcium sulfate is removed by filtration. The calcium in solution is then precipitated as carbonate by adding dilute sodium carbonate. It is then filtered and the filtrate evaporated down to about 400 ml, and allowed to cool to room temperature. The sodium anthraquinone-2-sulfonate separates out after standing for about 2 days. It is then filtered and washed with a little water. Yield 40—60% as silvery glistening plates, soluble in water, crystallises with one molecule of H2O;

Systematic organic chemistry, by W. M. Cumming, 325, 1937.

IUPAC Name

sodium;9,10-dioxoanthracene-2-sulfonate

InChI

InChI=1S/C14H8O5S.Na/c15-13-9-3-1-2-4-10(9)14(16)12-7-8(20(17,18)19)5-6-11(12)13;/h1-7H,(H,17,18,19);/q;+1/p-1

InChI Key

GGCZERPQGJTIQP-UHFFFAOYSA-M

Canonical SMILES

C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C=C(C=C3)S(=O)(=O)[O-].[Na+]

Depositor-Supplied Synonyms

Sodium anthraquinone-2-sulfonate, 131-08-8, Anthraquinone-2-sulfonic acid sodium salt, SBB057309, Silver salt, Sodium 9,10-dioxo-9,10-dihydroanthracene-2-sulfonate, 9,10-dioxoanthracene-2-sulfonic acid, sodium salt, 9,10-Dihydro-9,10-dioxo-2-anthracenesulfonic acid sodium salt, ACMC-1BPMR, DSSTox_CID_24535, DSSTox_RID_80298, UNII-511H72SDVX, DSSTox_GSID_44535, KSC491E3J, SCHEMBL305527, 123242_ALDRICH, 511H72SDVX, CHEMBL3184279, CTK3J1234, sodium anthraquinone-2-sulphonate, GGCZERPQGJTIQP-UHFFFAOYSA-M, MolPort-000-627-705, Tox21_301475, 6248AF, AKOS024364995, RTR-031319, TRA0096478, NCGC00255821-01, CAS-131-08-8, KB-80622, PL044365, TR-031319, A0508, FT-0611287, ST50997634, I08-1084, W-108339, 9,10-Anthraquinone-2-sulfonic acid sodium salt hydrate

Removed Synonyms

Sodium 2-anthraquinonesulfonate, Sodium 2-anthrachinonesulphonate, 2-Anthraquinone sodium sulfonate, CID9904754, Sodium 9,10-dioxoanthracene-2-sulfonate, Anthraquinone-2-sulfonic acid sodium salt monohydrate, 2-Anthracenesulfonic acid, 9,10-dihydro-9,10-dioxo-, sodium salt, 2-Anthracenesulfonic acid, 9,10-dihydro-9,10-dioxo-, sodium salt (1:1), 153277-35-1

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