Antraquinone (9,10-anthracenedione) is a representative of the quinone class. Practically insoluble in water, soluble in organic solvents. It was first synthesized by Auguste Laurent in 1835 by the oxidation of anthracene with nitric acid. It is used as an intermediate in the synthesis of dyes.
| Anthraquinone | |
|---|---|
 | |
| Are common | |
| Chem. formula | C 14 H 8 O 2 |
| Physical properties | |
| Molar mass | 208 g / mol |
| Thermal properties | |
| T. melt. | 286 ° C |
| T. bale. | 379.8 ° C |
| Classification | |
| Reg. CAS number | 84-65-1 |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| Chebi | |
| ChemSpider | |
Content
Physical Properties
Anthraquinone is a yellow or gray crystalline substance (monoclinic crystal lattice), it dissolves in nitrobenzene , aniline . Under the action of oleum, it forms successively anthraquinone-2-sulfonic acid, then a mixture of 2,6- and 2,7-anthraquinondisulfonic acid. With nitric acid forms 1-nitroantraquinone, then a mixture of 1,5- and 1,8-dinitroantraquinones.
Synthesis Methods
- Oxidation of anthracene .
- Condensation of benzene with phthalic anhydride in the presence of aluminum trichloride with the formation of ortho-benzoylbenzoic acid and its further cyclization.
- From naphthoquinone and butadiene according to the Diels-Alder reaction with the formation of 1,4,4a, 9a-tetrahydroantraquinone and its subsequent dehydrogenation, an excess of butadiene can be used as a dehydrogenating agent.
In industry, the first method is mainly used.
Being in nature
In nature, some plants are the source of anthraquinones, in particular, buckthorn .
Application
Derivatives of anthraquinone are used as dyes (for example, alizarin ). Anthraquinone is used in medicine as a laxative . In agriculture, it is used to scare away birds after sowing.
In the European Union, anthraquinone is banned as a hazardous to the health of consumers and potentially carcinogenic pesticide [1] .
Notes
- ↑ Carcinogenic substances , Germania.one (January 22, 2017) were discovered in black tea . Archived February 2, 2017.
Literature
- Chemical Encyclopedia / Editorial Board: Knunyants I.L. et al. - M .: Soviet Encyclopedia, 1988. - T. 1 (Abl-Dar). - 623 p.