Names | |
---|---|
Preferred IUPAC name
Anthracene-9,10-dione
[2] | |
Other names
| |
Identifiers | |
3D model (
JSmol)
|
|
390030 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.408 |
102870 | |
KEGG | |
PubChem
CID
|
|
RTECS number |
|
UNII | |
UN number | 3143 |
CompTox Dashboard (
EPA)
|
|
| |
| |
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 their
standard state (at 25 °C [77 °F], 100 kPa).
|
Anthraquinone, also called anthracenedione or dioxoanthracene, is an
aromatic
organic compound with formula C
14H
8O
2.
Isomers include various
quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (
IUPAC: 9,10-dioxoanthracene) wherein the
keto groups are located on the central ring. It is a building block of many
dyes and is used in bleaching pulp for papermaking. It is a yellow, highly crystalline solid, poorly
soluble in
water but soluble in hot organic solvents. It is almost completely insoluble in
ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral
hoelite.
There are several current industrial methods to produce 9,10-anthraquinone:
It also arises via the Rickert–Alder reaction, a retro-Diels–Alder reaction.
Hydrogenation gives dihydroanthraquinone (anthrahydroquinone). Reduction with copper gives anthrone. [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 of paper pulp by alkaline processes, like the kraft, the alkaline sulfite or the Soda-AQ processes. The anthraquinone is a redox catalyst. The reaction mechanism may involve single electron transfer (SET). [7] The anthraquinone oxidizes the reducing end of polysaccharides in the pulp, i.e., cellulose and hemicellulose, and thereby protecting it from alkaline degradation (peeling). The anthraquinone is reduced to 9,10-dihydroxyanthracene which then can react with lignin. 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 in kappa number. [8]
9,10-Anthraquinone is used as an electrolyte in flow battery which can provide long term electrical storage.
9,10-anthraquinone is used as a bird repellant on seeds, and as a gas generator in satellite balloons. [9] It has also been mixed with lanolin and used as a wool spray to protect sheep flocks against kea attacks in New Zealand. [10]
Several other isomers of anthraquinone are possible, including the 1,2-, 1,4-, and 2,6-anthraquinones. They are of comparatively minor importance. The term is also used in the more general sense of any compound that can be viewed as an anthraquinone with some hydrogen atoms replaced by other atoms or functional groups. These derivatives include substances that are technically useful or play important roles in living beings.
Recently, a class of anthraquinone derivates were shown to have self-healing properties when doped in PMMA matrix. [11]
Anthraquinone has no recorded LD50, probably because it is so insoluble in water.
In terms of metabolism of substituted anthraquinones, the enzyme encoded by the gene UGT1A8 has glucuronidase activity with many substrates including anthraquinones. [12]
Names | |
---|---|
Preferred IUPAC name
Anthracene-9,10-dione
[2] | |
Other names
| |
Identifiers | |
3D model (
JSmol)
|
|
390030 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.408 |
102870 | |
KEGG | |
PubChem
CID
|
|
RTECS number |
|
UNII | |
UN number | 3143 |
CompTox Dashboard (
EPA)
|
|
| |
| |
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 their
standard state (at 25 °C [77 °F], 100 kPa).
|
Anthraquinone, also called anthracenedione or dioxoanthracene, is an
aromatic
organic compound with formula C
14H
8O
2.
Isomers include various
quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (
IUPAC: 9,10-dioxoanthracene) wherein the
keto groups are located on the central ring. It is a building block of many
dyes and is used in bleaching pulp for papermaking. It is a yellow, highly crystalline solid, poorly
soluble in
water but soluble in hot organic solvents. It is almost completely insoluble in
ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral
hoelite.
There are several current industrial methods to produce 9,10-anthraquinone:
It also arises via the Rickert–Alder reaction, a retro-Diels–Alder reaction.
Hydrogenation gives dihydroanthraquinone (anthrahydroquinone). Reduction with copper gives anthrone. [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 of paper pulp by alkaline processes, like the kraft, the alkaline sulfite or the Soda-AQ processes. The anthraquinone is a redox catalyst. The reaction mechanism may involve single electron transfer (SET). [7] The anthraquinone oxidizes the reducing end of polysaccharides in the pulp, i.e., cellulose and hemicellulose, and thereby protecting it from alkaline degradation (peeling). The anthraquinone is reduced to 9,10-dihydroxyanthracene which then can react with lignin. 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 in kappa number. [8]
9,10-Anthraquinone is used as an electrolyte in flow battery which can provide long term electrical storage.
9,10-anthraquinone is used as a bird repellant on seeds, and as a gas generator in satellite balloons. [9] It has also been mixed with lanolin and used as a wool spray to protect sheep flocks against kea attacks in New Zealand. [10]
Several other isomers of anthraquinone are possible, including the 1,2-, 1,4-, and 2,6-anthraquinones. They are of comparatively minor importance. The term is also used in the more general sense of any compound that can be viewed as an anthraquinone with some hydrogen atoms replaced by other atoms or functional groups. These derivatives include substances that are technically useful or play important roles in living beings.
Recently, a class of anthraquinone derivates were shown to have self-healing properties when doped in PMMA matrix. [11]
Anthraquinone has no recorded LD50, probably because it is so insoluble in water.
In terms of metabolism of substituted anthraquinones, the enzyme encoded by the gene UGT1A8 has glucuronidase activity with many substrates including anthraquinones. [12]