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| Names | |
|---|---|
| Preferred IUPAC name Anthracene-9,10-dione[2] | |
Other names
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| Identifiers | |
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3D model (JSmol) | |
| 390030 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.001.408 |
| EC Number |
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| 102870 | |
| KEGG |
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| RTECS number |
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| UNII | |
| UN number | 3143 |
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| Properties | |
| C14H8O2 | |
| Molar mass | 208.216 g·mol−1 |
| Appearance | Yellow solid |
| Density | 1.438 g/cm3[1] |
| Melting point | 284.8 °C (544.6 °F; 558.0 K)[1] |
| Boiling point | 377 °C (711 °F; 650 K)[1] |
| Insoluble | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | possible carcinogen |
| GHS labelling: | |
 | |
| Danger | |
| H350 | |
| P201,P202,P281,P308+P313,P405,P501 | |
| Flash point | 185 °C (365 °F; 458 K) |
| Related compounds | |
Related compounds | quinone, anthracene |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Anthraquinone, also calledanthracenedione ordioxoanthracene, is anaromaticorganic compound with formulaC
14H
8O
2. Severalisomers exist but these terms usually refer to 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein theketo groups are located on the central ring. It is used as a digester additive towood pulp for papermaking. Manyanthraquinone derivatives are generated by organisms or synthesised industrially for use asdyes, pharmaceuticals, andcatalysts. Anthraquinone is a yellow, highly crystalline solid, poorlysoluble inwater but soluble in hot organic solvents. It is almost completely insoluble inethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineralhoelite.
There are several current industrial methods to produce 9,10-anthraquinone:
It also arises via the Rickert–Alder reaction, aretro-Diels–Alder reaction.
Hydrogenation givesdihydroanthraquinone (anthrahydroquinone). Reduction with copper givesanthrone.[4] Sulfonation with sulfuric acid gives anthroquinone-1-sulfonic acid,[5] which reacts with sodium chlorate to give 1-chloroanthaquinone.[6]
9,10-Anthraquinone is used as a digester additive in production ofpaper pulp byalkaline processes, like thekraft, the alkalinesulfite or theSoda-AQ processes. The anthraquinone is aredoxcatalyst. The reaction mechanism may involvesingle electron transfer (SET).[7] The anthraquinone oxidizes the reducing end of polysaccharides in the pulp, i.e.,cellulose andhemicellulose, and thereby protecting it from alkaline degradation (peeling). The anthraquinone is reduced to9,10-dihydroxyanthracene which then can react withlignin. The lignin is degraded and becomes more watersoluble and thereby more easy to wash away from the pulp, while the anthraquinone is regenerated. This process gives an increase in yield of pulp, typically 1–3% and a reduction inkappa number.[8]
2-Alkyl-9,10-Anthroquinones are used as a catalyst in theanthraquinone process for the production of hydrogen peroxide. This process is the dominant industrial method of hydrogen peroxide production.[9]
9,10-anthraquinone is used as a bird repellant on seeds, and as a gas generator in satellite balloons.[10] It has also been mixed with lanolin and used as a wool spray to protect sheep flocks againstkea attacks in New Zealand.[11]
Several other isomers of anthraquinone exist, including the 1,2-, 1,4-, and 2,6-anthraquinones. They are of minor importance compared to 9,10-anthraquinone.
Anthraquinone has no recordedLD50, probably because it is so insoluble in water.
In terms of metabolism of substituted anthraquinones, the enzyme encoded by the geneUGT1A8 has glucuronidase activity with many substrates including anthraquinones.[12]
| International | |
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| Other | |
