Difference between revisions of "Anthraquinone"
(Created page with "{{Chembox | Name = Anthraquinone | Reference = | IUPACName = Anthraquinone | PIN = | SystematicName = | OtherNames = 9,10-Anthracenedione<br>9,10-Anthrachinon<br>9,10-Dihydro-...") |
|||
| (4 intermediate revisions by the same user not shown) | |||
| Line 129: | Line 129: | ||
There are several routes for anthraquinone. | There are several routes for anthraquinone. | ||
| − | One involves the oxidation of anthracene, with Cr(VI). | + | 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 [[Aluminium chloride|AlCl<sub>3</sub>]]. The reaction gives o-benzoylbenzoic acid, which undergoes cyclization, forming anthraquinone. | + | A more convenient route is the [[Friedel-Crafts reaction]] of [[benzene]] and [[phthalic anhydride]] in presence of [[Aluminium chloride|AlCl<sub>3</sub>]]. The reaction gives o-benzoylbenzoic acid, which undergoes cyclization, forming anthraquinone. |
==Projects== | ==Projects== | ||
| Line 139: | Line 139: | ||
*Make synthetic dyes | *Make synthetic dyes | ||
*Digester additive in papermaking | *Digester additive in papermaking | ||
| − | *Bird | + | *Bird repellent |
==Handling== | ==Handling== | ||
| Line 146: | Line 146: | ||
===Storage=== | ===Storage=== | ||
| − | + | Anthraquinone should be kept in closed plastic of glass bottles. | |
===Disposal=== | ===Disposal=== | ||
| − | Can be mixed with more flammable solvent and burned. | + | Can be mixed with more flammable solvent and burned. Oxidizing mixtures can also be used. |
==References== | ==References== | ||
| Line 159: | Line 159: | ||
===Relevant Sciencemadness threads=== | ===Relevant Sciencemadness threads=== | ||
*[http://www.sciencemadness.org/talk/viewthread.php?tid=66047 Alizarin synthesis] | *[http://www.sciencemadness.org/talk/viewthread.php?tid=66047 Alizarin synthesis] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=160017 Synthesis of 9,9‘-bianthracene from anthraquinone] | ||
[[Category:Chemical compounds]] | [[Category:Chemical compounds]] | ||
[[Category:Organic compounds]] | [[Category:Organic compounds]] | ||
| + | [[Category:Aromatic compounds]] | ||
[[Category:Quinones]] | [[Category:Quinones]] | ||
[[Category:Minerals]] | [[Category:Minerals]] | ||
Latest revision as of 22:31, 27 December 2023
| 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.
