|Other names||9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, Hoelite, Morkit, Corbit|
3D model (JSmol)
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|Molar mass||208.23 g/mol|
|Appearance||yellow or light gray to gray-green solid|
|Except where noted otherwise, data are given for|
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
Its other names are 9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, and trade names Hoelite, Morkit, Corbit, and others.
Anthraquinone naturally occurs in some plants (eg. aloe, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and insects, where it serves as a basic skeleton for their pigments. Natural anthraquinone derivatives tend to have laxative effects.
There are several ways to obtain anthraquinone:
- Oxidation of anthracene
- Condensation of benzene with phthalic anhydride in presence of AlCl3 (Friedel-Crafts substitution). The resulting o-benzoylbenzoic acid then undergoes cyclization, forming anthraquinone.
- Diels-Alder reaction (from naphthoquinone and a 1,3-diene followed by oxidation)
- Retro-DA reaction: the Rickert-Alder reaction.
In a classic organic reaction called the Bally-Scholl synthesis (1905), anthraquinone condenses with glycerol forming benzanthrone. In this reaction the quinone is first reduced with copper metal in sulfuric acid (converting one ketone group into a methylene group) after which the glycerol is added.
Anthraquinone is used in production of dyes, such as alizarin. Many natural pigments are derivatives of anthraquinone. Anthraquinone is also used as a catalyst in production of wood pulp in pulp and paper industry. Another use is as a bird repellant on seeds.
A derivative of anthraquinone (2-ethylanthraquinone) is used to produce hydrogen peroxide commercially.
- National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet
- Molecules Spontaneously Form Honeycomb Network