Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
2. Isomers include various quinone derivatives. The term anthraquinone, however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite.
|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||208.216 g·mol−1|
|Melting point||286 °C (547 °F; 559 K)|
|Boiling point||379.8 °C (715.6 °F; 653.0 K)|
|GHS Signal word||Danger|
|P201, P202, P281, P308+313, P405, P501|
|Flash point||185 °C (365 °F; 458 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
There are several current industrial methods to produce 9,10-anthraquinone:
- The oxidation of anthracene. Chromium(VI) is the typical oxidant.
- The Friedel-Crafts reaction of benzene and phthalic anhydride in presence of AlCl3. o-Benzoylbenzoic acid is an intermediate. This reaction is useful for producing substituted anthraquinones.
- The Diels-Alder reaction of naphthoquinone and butadiene followed by oxidative dehydrogenation.
- The acid-catalyzed dimerization of styrene to give a 1,3-diphenylbutene, which then can be transformed to the anthraquinone. This process was pioneered by BASF.
It also arises via the Rickert-Alder reaction, a retro-Diels-Alder reaction.
Hydrogenation gives dihydroanthraquinone (anthrahydroquinone). Reduction with copper gives anthrone. Sulfonation with sulfuric acid gives anthroquinone-1-sulfonic acid, which reacts with sodium chlorate to give 1-chloroanthaquinone.
Digester additive in papermakingEdit
9,10-Anthraquinone is used as a digester additive in production of paper pulp by alkaline processes, like the kraft, the alkaline sulfite or the Soda-AQ processes. The anthraquinone is a redox catalyst. The reaction mechanism may involve single electron transfer (SET). The anthraquinone oxidizes the reducing end of polysaccharides in the pulp, i.e., cellulose and hemicellulose, and thereby protecting it from alkaline degradation (peeling). The anthraquinone is reduced to 9,10-dihydroxyanthracene which then can react with lignin. The lignin is degraded and becomes more watersoluble and thereby more easy to wash away from the pulp, while the anthraquinone is regenerated. This process gives an increase in yield of pulp, typically 1-3% and a reduction in kappa number.
Use in flow batteriesEdit
9,10-Anthraquinone is used as an electrolyte in flow battery which can provide long term electrical storage.
9,10-anthraquinone is used as a bird repellant on seeds, and as a gas generator in satellite balloons. It has also been mixed with lanolin and used as a wool spray to protect sheep flocks against kea attacks in New Zealand.
Several other isomers of anthraquinone are possible, including the 1,2-, 1,4-, and 2,6-anthraquinones. They are of comparatively minor importance. The term is also used in the more general sense of any compound that can be viewed as an anthraquinone with some hydrogen atoms replaced by other atoms or functional groups. These derivatives include substances that are technically useful or play important roles in living beings.
Anthraquinone has no recorded LD50, probably because it is so insoluble in water.
- International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 724. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
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