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.
Contents
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). Anthraquinone is extracted from the reaction mass and purified.
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 repellent
Handling
Safety
Anthraquinone is irritant and protection should be worn when handling the compound. Prolonged exposure may lead to melanosis coli.
Storage
Anthraquinone should be kept in closed plastic of glass bottles.
Disposal
Can be mixed with more flammable solvent and burned. Oxidizing mixtures can also be used.
