1,5-dihydroxyanthraquinone

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Structural formula
Structure of 1,5-dihydroxyanthraquinone
General
Surname 1,5-dihydroxyanthraquinone
other names
  • Anthrarufin
  • 1,5-dihydroxy-9-10-anthracenedione
  • 1,5-dihydroxy-9,10-anthraquinone
Molecular formula C 14 H 8 O 4
Brief description

Yellow powder

External identifiers / databases
CAS number 117-12-4
EC number 204-175-6
ECHA InfoCard 100.003.796
PubChem 8328
Wikidata Q27117170
properties
Molar mass 240.21 g · mol -1
Physical state

Firmly

Melting point

280 ° C

solubility
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,5-Dihydroxyanthraquinone , also known as anthrarufin , is an organic compound from the group of anthraquinones (more precisely the dihydroxyanthraquinones ).

history

When Edward Schunk and H. Römer mixed concentrated sulfuric acid with methoxybenzoic acid , they each received a product which was soluble and insoluble in water. The insoluble product could be separated again by washing it with barite water . The insoluble part contained 1,5-dihydroxanthraquinone, which was named anthrarufin.

presentation

Anthrarufin can be made by reacting concentrated sulfuric acid with methoxybenzoic acid. The precipitate obtained is washed with water and barite water and recrystallized with glacial acetic acid . The yield is about 2%.

Another possibility to win anthrarufin is anthracene with conc. Mix sulfuric acid. After about half of the anthracene has gone into the solution, anthrarufin precipitates when heated. The yield here is about 45%.

In 1883, H. Römer described a further reaction in which diamidoanthraquinones and / or dinitroanthraquinones in conc. Sulfuric acid can be dissolved. By adding water and potassium nitrite and repeated heating, a product is obtained which is redissolved in potassium hydroxide solution . The pure anthrarufin can then be obtained with hydrochloric acid and barite water.

properties

Anthrarufin produced with conc. Sulfuric acid is a very cherry-red solution with a carmine-red fluorescence. It is sufficient a proportion of from 10 -2  % in concentrated sulfuric acid to produce this coloration.  A crimson red solution is obtained with a proportion of 10–6 % .

use

Anthrarufin is not suitable for pickling as it does not cause discoloration. However, it can be converted to oxyanthrarufin (1,2,5-trihydroxyanthraquinone) by melting potash. This can be used for pickling, which it colors similar to alizarin .

It can also be converted to alizarin sapphirol, which is a particularly lightfast dye . To do this, the anthrarufin has to be disulphonated , dinitrated and reduced .

Individual evidence

  1. ↑ Data sheet 1,5-Dihydroxyanthraquinone at AlfaAesar, accessed on July 24, 2017 ( PDF )(JavaScript required) .
  2. ↑ a b c d e f g h i j E. Schunck, H. Römer: Ueber Anthrarufin, a new Bioxyanthraquinone from metaoxybenzoic acid. In: Reports of the German Chemical Society . 11, 1878, pp. 1176-1179, doi: 10.1002 / cber.187801101314 .
  3. ↑ a b Datasheet Anthrarufin from Sigma-Aldrich , accessed on July 5, 2017 ( PDF ).
  4. ↑ C. Liebermann, K. Boeck: About anthracenedisulfonic acid and its conversion into anthrarufin. In: Reports of the German Chemical Society . 11, 1878, pp. 1613-1618, doi: 10.1002 / cber.18780110299 .
  5. ↑ a b c H. Roemer: Ueber 1, IV. Diorthonitroanthraquinone, 1, IV. Diorthoamidoanthraquinone and a new way of presenting anthrarufin. In: Reports of the German Chemical Society . 16, 1883, pp. 363-372, doi: 10.1002 / cber.18830160188 .
  6. ↑ Robert E. Schmidt: Brief overview of the development of the anthraquinone dyes. In: Journal of Applied Chemistry . 41, 1928, pp. 41-46, doi: 10.1002 / anie.19280410202 .