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Anthraquinone



Anthraquinone
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

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.

Additional recommended knowledge

Contents

Physical properties

It is semisoluble in water but dissolves in alcohol, nitrobenzene and aniline. It is chemically fairly stable under normal conditions.

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.

Chemistry

There are several ways to obtain anthraquinone:

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.

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.

Medical uses

Anthraquinone is used as a laxative. Prolonged use and abuse leads to melanosis coli.[2][3]

References

  1. ^ L. C. Macleod and C. F. H. Allen (1943). "Benzathrone". Org. Synth.; Coll. Vol. 2: 62. 
  2. ^ Müller-Lissner SA (1993). "Adverse effects of laxatives: fact and fiction". Pharmacology 47 Suppl 1: 138-45. PMID 8234421.
  3. ^ 3280173
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Anthraquinone". A list of authors is available in Wikipedia.
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