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anthraquinone

Product name anthraquinone
Synonyms 9,10-anthracenedione
GOST no data
CAS 84-65-1

Anthraquinone is a light-yellow crystalline compound. It is soluble in most organic solvents, almost insoluble in water. It is a derivative of anthracene and has a planar geometry. Anthraquinone can be reversibly reduced with sodium thiosulfate in alkali medium to form 9,10-dihydroxyanthracene (anthrahydroquinone). Anthraquinone reacts with 20-40 oleum to give step by step anthraquinone-2-sulfonic acid and the mixture of 2,6-disulfonic and 2,7-disulfonic acids without catalyst or anthraquinone-1-sulfonic acid and then the mixture of 1,5- and 1,8-disulfonic acids in the presence of mercury(II) salts as a catalyst. Anthraquinone motif naturally occurs in some plants (eg. aloe, senna, rhubarb, and Cascara buckthorn) and insects, where it serves as a basic fragment of their pigments.

Production.

Anthraquinone is prepared industrially:

  • by oxidation of purified anthracene with air at 360-380°C in the presence of vanadium pentaoxide V2O5 catalyst;
  • by condensation of benzene with phthalic anhydride on Friedel-Crafts mechanism in the presence of aluminium chloride AlCl3;
  • by Diels-Alder reaction from 1,4-naphthoquinone and 1,3-butadiene;

    Uses.

    Anthraquinone is applied:

  • as a starting material in making of a large class of dyes and pigments (e.g alizarin);
  • for benzanthrone synthesis;
  • in paper industry as a catalyst to increase the pulp production yield;
  • as an intermediate in preparation of coloring compounds, antioxidants, and polymerization inhibitors;
  • as a bird repellant on seeds;

  • Manufacturer(s) no data
    Chemical structure of anthraquinone

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