Anthraquinone

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Anthraquinone
Names
IUPAC name
Anthraquinone
Other names
9,10-Anthracenedione
9,10-Anthrachinon
9,10-Dihydro-9,10-dioxoanthracene
Anthracene-9,10-quinone
Anthradione
Corbit
Hoelite
Morkit
9,10-AQ
Properties
C14H8O2
Molar mass 208.22 g/mol
Appearance Yellow solid
Odor Aromatic-like odor
Density 1.438 g/cm3 (at 20 °C)
Melting point 286 °C (547 °F; 559 K)
Boiling point 379.8 °C (715.6 °F; 653.0 K)
Insoluble
Solubility Soluble in acetone, conc. sulfuric acid
Poorly soluble in benzene, chloroform, diethyl ether, ethanol, toluene
Vapor pressure 1.16·10-7 mmHg at 25 °C
Hazards
Safety data sheet FisherScientific
Flash point 185 °C
Related compounds
Related compounds
1,4-Benzoquinone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Anthraquinone or dioxoanthracene, is an aromatic organic compound with formula C14H8O2. The name anthraquinone refers almost invariable to the 9,10-anthraquinone isomer.

It can be found in nature as the rare mineral Hoelite.

Properties

Chemical

9,10-Anthraquinone can be hydrogenated in the presence of a palladium catalyst to 9,10-anthrahydroquinone. This in turn is oxidized with oxygen back to anthraquinone, generating hydrogen peroxide. This is the basis for the anthraquinone process. 2-Ethylanthraquinone is however preferred in the said process instead of anthraquinone, as it has better selectivity.

It resists the attack of many acids and bases.

Physical

Anthraquinone is a yellow solid, insoluble in water. It has an odor described as aromatic/technical-like. It is soluble in acetone, concentrated sulfuric acid, and sparingly soluble in cold ethanol, but slightly more soluble when hot. It is also poorly soluble in other organic solvents like benzene, chloroform, diethyl ether, toluene.

Availability

9,10-Anthraquinone can be purchased online from chemical suppliers.

It can also be purchased as the rare mineral Hoelite.

Preparation

There are several routes for anthraquinone.

One involves the oxidation of anthracene, with Cr(VI).

A more convenient route is the Friedel-Crafts reaction of benzene and phthalic anhydride in presence of AlCl3. The reaction gives o-benzoylbenzoic acid, which undergoes cyclization, forming anthraquinone.

Projects

  • Anthraquinone process
  • Make anthracene
  • Benzanthrone synthesis
  • Make synthetic dyes
  • Digester additive in papermaking
  • Bird repellant

Handling

Safety

Anthraquinone is irritant and protection should be worn when handling the compound. Prolonged exposure may lead to melanosis coli.

Storage

In closed bottles.

Disposal

Can be mixed with more flammable solvent and burned.

References

Sciencemadness Library

Relevant Sciencemadness threads