Anthraquinone
From Wikipedia, the free encyclopedia
| Anthraquinone | |
|---|---|
 |
|
| Chemical name | Anthraquinone |
| Chemical formula | C14H8O2 |
| Molecular mass | 208.23 g/mol |
| CAS number | [84-65-1] |
| Density | x.xxx g/cm³ |
| Melting point | 286 °C |
| Boiling point | 379.8 °C |
| SMILES | O=C2c1ccccc1C(c3c2cccc3)=O |
| Disclaimer and references | |
Anthraquinone (9,10-dioxoanthracene) is an aromatic organic compound. It is a derivative of anthracene. It has the appearance of yellow or light gray to gray-green solid crystalline powder.
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.
Contents |
[edit] Physical properties
It is insoluble in water or alcohol, but dissolves in nitrobenzene and aniline. It is chemically fairly stable under normal conditions.
[edit] Natural occurrences
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.
[edit] Chemistry
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)
In a classic organic reaction called the Bally-Scholl Synthesis (1905), anthraquinone condenses with glycerol forming Benzanthrone [1]. 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.
[edit] Industrial applications
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.
Its risk and safety phrases are R36/37/38.
[edit] External links
- National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet
- - Molecules Spontaneously Form Honeycomb Network
- Links to external chemical sources.
[edit] References
- ^ Benzathrone L. C. Macleod and C. F. H. Allen. Organic Syntheses, Coll. Vol. 2, p.62 (1943); Vol. 14, p.4 (1934). Link
