1,4-Dihydroxyanthraquinone

1,4-Dihydroxyanthraquinone
Identifiers
CAS number 81-64-1 Y
PubChem 6688
ChemSpider 6433 Y
ChEBI CHEBI:37487 Y
ChEMBL CHEMBL17594 N
Jmol-3D images Image 1
Properties
Molecular formula C14H8O4
Molar mass 240.21 g/mol
Appearance Orange or red-brown crystalline powder
Melting point

198–199 °C

Boiling point

450 °C

 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is an organic compound derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxyl (OH) groups. It is one of ten dihydroxyanthraquinone isomers and occurs in small amounts (as a glycoside) in the root of the madder plant, Rubia tinctorum.[1]

Contents

Production

Quinizarin is produced by the reaction of phthalic anhydride and 4-chlorophenol followed by hydrolysis of the chloride:[2]

C6H4(CO)2O + ClC6H4OH → C6H4(CO)2C6H2(OH)Cl + H2O
C6H4(CO)2C6H2(OH)Cl + H2O → C6H4(CO)2C6H2(OH)2 + HCl

It can also be prepared less efficiently from phthalic anhydride and hydroquinone.

Uses

Quinizarin is an inexpensive dye that is used to colour gasoline and some heating oils. It is used as an intermediate for the synthesis of indanthrene- and alizarin-derived dyes. The OH groups can be replaced by chloride. Chlorination and bromination afford other dyes. Amination (replacement of one OH by ArNH) with aniline derivatives followed by sulfonation affords other dyes such as Acid Violet 43. It is also used to form lake pigments with calcium, barium, and lead.[2]

See also

References

  1. ^ Goverdina C. H. Derksen, Harm A. G. Niederländer and Teris A. van Beek (2002), Analysis of anthraquinones in Rubia tinctorum L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection. Journal of Chromatography A, Volume 978, Issues 1-2, Pages 119-127. doi:10.1016/S0021-9673(02)01412-7
  2. ^ a b Hans-Samuel Bien, Josef Stawitz, Klaus Wunderlich “Anthraquinone Dyes and Intermediates” Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinhem. doi:10.1002/14356007.a02_355