Anthraquinone
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| Anthraquinone | |
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| General | |
| Systematic name | Anthraquinone |
| Other names | 9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, Hoelite, Morkit, Corbit |
| Molecular formula | C14H8O2 |
| SMILES | O=C2c1ccccc1C(c3c2cccc3)=O |
| Molar mass | 208.23 g/mol |
| Appearance | yellow or light gray to gray-green solid |
| CAS number | [84-65-1] |
| Properties | |
| Density and phase | ? g/cm³, ? |
| Solubility in water | ? g/100 ml (?°C) |
| Melting point | 286 °C |
| Boiling point | 379.8 °C |
| Structure | |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | ?°C |
| R/S statement | R: R36/37/38 S: ? |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Anthraquinone (9,10-dioxoanthracene) is an aromatic organic compound. It is a derivative of anthracene. It has the appearance of yellow or light gray to gray-green solid crystalline powder.
Its other names are 9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, and trade names Hoelite, Morkit, Corbit, and others.
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[edit] Physical properties
It is insoluble in water or alcohol, but dissolves in nitrobenzene and aniline. It is chemically fairly stable under normal conditions.
[edit] Natural occurrences
Anthraquinone naturally occurs in some plants (eg. aloe, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and insects, where it serves as a basic skeleton for their pigments. Natural anthraquinone derivatives tend to have laxative effects.
[edit] Chemistry
There are several ways to obtain anthraquinone:
- Oxidation of anthracene
- Condensation of benzene with phthalic anhydride in presence of AlCl3 (Friedel-Crafts substitution). The resulting o-benzoylbenzoic acid then undergoes cyclization, forming anthraquinone.
- Diels-Alder reaction (from naphthoquinone and a 1,3-diene)
In a classic organic reaction called the Bally-Scholl Synthesis (1905), anthraquinone condenses with glycerol forming Benzanthrone [1]. 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.
[edit] Industrial applications
Anthraquinone is used in production of dyes, such as alizarin. Many natural pigments are derivatives of anthraquinone. Anthraquinone is also used as a catalyst in production of wood pulp in pulp and paper industry. Another use is as a bird repellant on seeds.
A derivative of anthraquinone (2-ethylanthraquinone) is used to produce hydrogen peroxide commercially.
[edit] External links
- National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet
- - Molecules Spontaneously Form Honeycomb Network
- Links to external chemical sources
[edit] References
- ^ Benzathrone L. C. Macleod and C. F. H. Allen. Organic Syntheses, Coll. Vol. 2, p.62 (1943); Vol. 14, p.4 (1934). Link
