m Anthraquinone template |
Updating {{chembox}} (no changed fields - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|err |
||
| Line 12: | Line 12: | ||
| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
||
| SMILES = O=C1c2ccccc2C(=O)c3ccccc13 |
| SMILES = O=C1c2ccccc2C(=O)c3ccccc13 |
||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|||
| |
| ChemSpiderID = 6522 |
||
| CASNo_Ref = {{cascite}} |
| CASNo_Ref = {{cascite}} |
||
| CASNo = 84-65-1 |
| CASNo = 84-65-1 |
||
Revision as of 12:18, 29 November 2010
| |
| Ball-and-stick model | |
| Names | |
|---|---|
| IUPAC name
Anthraquinone
| |
| Other names
9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, Hoelite, Morkit, Corbit
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.001.408 |
CompTox Dashboard (EPA)
|
|
| |
| Properties | |
| C14H8O2 | |
| Molar mass | 208.216 g·mol−1 |
| Appearance | yellow solid |
| Melting point | 286 °C |
| Boiling point | 379.8 °C |
| Insoluble | |
| Hazards | |
| Flash point | 185°C |
| Related compounds | |
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, that can be viewed as a diketone derivative of anthracene (with loss of one of the central pi-bonds in the anthracene).
The term usually refers to one specific isomer, 9,10-anthraquinone or 9,10-dioxoanthracene, whose ketone groups are on the central ring. This compound is an important member of the quinone family. It is a building block of many dyes and is industrially used in bleaching pulp for papermaking. It is a yellow highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. For instance, it is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol.
Several other anthraquinone isomers are possible, such as 1,2-, 1,4-, and 2,6-anthraquinone, but 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 many substances that are technically useful or play important roles in living beings.
Synthesis
9,10-Anthraquinone is obtained industrially by the oxidation of anthracene, a reaction that is localized at the central ring. Chromium(VI) is the typical oxidant. It is also prepared by the Friedel-Crafts reaction of benzene and phthalic anhydride in presence of AlCl3. The resulting o-benzoylbenzoic acid then undergoes cyclization, forming anthraquinone. This reaction is useful for producing substituted anthraquinones. The Diels-Alder reaction of naphthoquinone and butadiene followed by oxidative dehydrogenation. Lastly, BASF has developed a process that proceeds via the acid-catalyzed dimerization of styrene to give a 1,3-diphenylbutene, which then can be transformed to the anthaquinone.[1]
It also arises via the Rickert-Alder reaction, a retro-Diels-Alder reaction. In a classic (1905)organic reaction called the Bally-Scholl synthesis, anthraquinone condenses with glycerol forming benzanthrone[2]. In this reaction, the quinone is first reduced with copper metal in sulfuric acid (converting one ketone group into a methylene group) after which the glycerol is added.
Applications and natural occurrence
Dyestuff precursor
Synthetic dyes are often derived from 9,10-anthraquinone, such as alizarin. Important derivatives are 1-nitroanthraquinone, anthraquinone-1-sulfonic acid, and the dinitroanthraquinone.[1] Natural pigments that are derivatives of anthraquinone are found, inter alia, in aloe latex, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and some insects.
Digester additive in papermaking
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 going through a redox cycle and is giving a catalytic effect. The reaction mechanism is most likely single electron transfer (SET).[3] The antraquinone is oxidizing cellulose 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 antraquinone is regenerated. This process gives an increase in yield of pulp, typically 1-3 % and a reduction in kappa number[4].
Sodium 2-anthraquinonesulfonate (AMS) is a watersoluble anthraquinone derivative that was the first anthraquinone derivative discovered to have a catalytic effect in the alkaline pulping processes[5].
In the production of hydrogen peroxide
A large industrial application of anthraquinones is for the production of hydrogen peroxide. 2-Ethyl-9,10-anthraquinone or a related alkyl derivatives is used, rather anthraquinone itself.[6]
Catalytic hydrogen peroxide production with the anthraquinone process
Medicine
Derivatives of 9,10-anthraquinone include many important drugs (collectively called anthracenediones). They include
- laxatives like dantron, emodin, and aloe emodin, and some of the senna glycosides
- antimalarials like rufigallol
- antineoplastics used in the treatment of cancer, like mitoxantrone, pixantrone, and the anthracyclines.
| File:Aloe emodin structure.png |  |
 |
| Aloe emodin | Mitoxantrone | Pixantrone |
Niche uses
9,10-Anthraquinone is used as a bird repellant on seeds and as a gas generator in satellite balloons[1].
Natural anthraquinone derivatives tend to have laxative effects. Prolonged use and abuse leads to melanosis coli.[7][8]
See also
References
- ^ a b Axel Vogel "Anthraquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_347
- ^ L. C. Macleod and C. F. H. Allen (1943). "Benzathrone". Organic Syntheses; Collected Volumes, vol. 2, p. 62.
- ^ Samp, James Christian (2008), A comprehensive mechanism for anthraquinone mass transfer in alkaline pulping, Georgia Institute of Technology, p. 30
- ^ Sturgeoff, L.G.; Pitl, Y. (1997) [1993]. Goyal, Gopal C. (ed.). Low Kappa pulping without capital investment. pp. 3–9. ISBN 0-89852-340-0.
{{cite book}}:|journal=ignored (help) - ^ "Anthraquinone/ alkali pulping. A literature review" (PDF). 1978.
{{cite web}}: Cite has empty unknown parameters:|trans_title=,|separator=, and|coauthors=(help); Unknown parameter|month=ignored (help) - ^ Gustaaf Goor, Jürgen Glenneberg, Sylvia Jacobi "Hydrogen Peroxide" in Ullmann's Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a13_443.pub2.
- ^ Müller-Lissner SA (1993). "Adverse effects of laxatives: fact and fiction". Pharmacology. 47 Suppl 1: 138–45. doi:10.1159/000139853. PMID 8234421.
- ^ Moriarty KJ, Silk DB (1988). "Laxative abuse". Dig Dis. 6 (1): 15–29. doi:10.1159/000171181. PMID 3280173.