Anthraquinone
From Wikipedia, the free encyclopedia
| Anthraquinone | |
|---|---|
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| IUPAC name | Anthraquinone |
| Other names | 9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, Hoelite, Morkit, Corbit |
| Identifiers | |
| CAS number | [84-65-1] |
| SMILES | O=C1c2ccccc2C(=O)c3ccccc13 |
| Properties | |
| Molecular formula | C14H8O2 |
| Molar mass | 208.23 g/mol |
| Appearance | yellow or light gray to gray-green solid |
| Melting point |
286 °C |
| Boiling point |
379.8 °C |
| Solubility in water | Insoluble |
| Hazards | |
| R-phrases | R36/37/38 |
| Flash point | 185°C |
| Related compounds | |
| Related compounds | quinone, anthracene |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.
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[edit] Physical properties
It is semisoluble in water but dissolves in alcohol, nitrobenzene and aniline. It is chemically fairly stable under normal conditions.
[edit] Natural occurrences
Anthraquinones naturally occur in some plants (eg. aloe, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and insects, where they serve 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 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[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.
[edit] Medical uses
Anthraquinone is used as a laxative. Prolonged use and abuse leads to melanosis coli.[2][3]
[edit] External links
- National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet
- Molecules Spontaneously Form Honeycomb Network
[edit] References
- ^ L. C. Macleod and C. F. H. Allen (1943). "Benzathrone". Org. Synth.; Coll. Vol. 2: 62.
- ^ Müller-Lissner SA (1993). "Adverse effects of laxatives: fact and fiction". Pharmacology 47 Suppl 1: 138-45. PMID 8234421.
- ^ 3280173
