ChemicalBook CAS DataBase List 1-Anthraquinonesulfonic acid

1-Anthraquinonesulfonic acid synthesis

9synthesis methods

Product Name:1-Anthraquinonesulfonic acid
CAS Number:82-49-5
Molecular formula:C14H8O5S
Molecular Weight:288.28

Anthraquinone-1-sulfonic acid, K salt, also called diamant salt, is prepared by sulfonation in the presence of, e.g., 0.5 % mercury in 20 % oleum, an amount of SO3 adequate for the sulfonation of about 60 % of the charge. The reaction is controlled in such a manner that about 50 % of the anthraquinone remains unsulfonated. After mercury is precipitated as the sulfide, the unreacted anthraquinone is precipitated by dilution and is collected by filtration. After washing and drying, it is recirculated as ‘reclaimed quinone‘. Mercury is removed completely from the filtrate, and the anthraquinone-1-sulfonic acid is then precipitated as the potassium salt .

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Yield: 98%

Reaction Conditions:

in nitric acid-treated palladium;sulfuric acid

Steps:

1.c (a)
(c) Sulphonation of anthraquinone in the presence of the nitric acid-treated palladium To a solution of 6 ml of 65% oleum in 14 ml of 95% sulphuric acid was added the nitric acid-treated palladium (Treatment (a)) at room temperature. Then, 20.8 gm of anthraquinone was added to the above mixture at a heated temperature of about 70 degs C. Finally, 10 ml of 65% oleum was added dropwise at 90 degs C. in one hour, and the mixture was agitated at this temperatture for another 3 hours. The reaction mixture contains the following mole percentages of components based on the moles of anthraquinone added. When the reaction mixture was diluted with water and filtered and the anthraquinone-1-sulphonic acid was salted out from the filtrate, 28.7 gm of sodium salt of the anthraquinone-1-sulphonic acid with 98% purity was obtained.

References:

501 China Technical Consultants, Inc. US4711743, 1987, A