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ChemicalBook CAS DataBase List 1,4-Dihydroxyanthraquinone
81-64-1

1,4-Dihydroxyanthraquinone synthesis

14synthesis methods
commonly known as Quinizarin. (a) Boric acid, boric acid and mercury, boric acid and nitrous acid or nitrous acid and mercury in the presence of Anthracene-9,10-dione with sulfuric acid; (b) In the presence of boric acid and nitrous acid, treated with sulfuric acid ?1-Hydroxyanthracene-9,10-dione or 2-Hydroxyanthracene-9,10-dione, (c)In the presence of boric acid, treated with sulfuric acid 1-Hydroxy-4-nitroanthracene-9,10-dione?or?1,4-Dichloroanthracene-9,10-dione?; (d) in the Boric acid and where did in the presence of sulfuric acid, Phthalic anhydride and 4-Chlorophenol?or Hydroquinone condensation, closed loop.
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Yield:81-64-1 96%

Reaction Conditions:

with boron trioxide;sulfuric acid at 125 - 160; for 16 h;Temperature;

Steps:

1; 2 Example 2:

In a dry 500nl four-necked flask, 145 g (1.45 mol) of 98% sulfuric acid was added, 50.5 g (0.726 mol) of boric anhydride was added under stirring, and after the addition, stirred for 15 minutes to make it fully dissolved. Then 59.1 g of phthalic anhydride (molecular weight 148.1, 0.399 mol) and 40 g of hydroquinone (molecular weight 110.1, 0.363 mol) were added, and stirred for 15 minutes to fully dissolve. Begin to heat up with a heat-conducting oil furnace, heat up to 125°C, and keep it at 125-130°C for 8 hours. Then continue to heat up to 155°C, and keep it at 155-160°C for 8 hours. After the heat preservation, the temperature is lowered to 50-60°C, and the reaction materials are transferred to a four-neck flask filled with 730g of clear water. After the material transfer is completed, the temperature is controlled at 100-110°C, and the isolation is about 2 hours. Then the temperature is lowered to 60-80°C, filtered, washed with water, and dried to obtain the product. 85.20 g of 1,4-dihydroxyanthraquinone was obtained, the chromatographic content was 98.25%, and the yield was 96.0%.

References:

CN113072439,2021,A Location in patent:Paragraph 0020-0023

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