Anthanthrone
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| Surname | Anthanthrone | ||||||||||||||||||
| Molecular formula | C 22 H 10 O 2 | ||||||||||||||||||
| Brief description |
orange solid |
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| Molar mass | 306.31 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Anthanthrone is a chemical compound . It is structurally derived from anthanthrene and has two carbonyl groups . It thus shows similarities to anthraquinone .
Extraction and presentation
Anthanthrone can be obtained by dehydrating 1,1'-dinaphthyl-2,2'-dicarboxylic acid or 1,1'-dinaphthyl-8,8'-dicarboxylic acid with sulfuric acid , chlorosulfonic acid or aluminum chloride, the dicarboxylic acids in turn starting from 1-aminonaphthalene can be represented. This synthesis was used in the first description of the compound by Ludwig Kalb in 1914.
properties
Anthanthrone is remarkably resistant to the action of alkalis and oxidizing agents . A sulfation occurs difficult one, easy contrast nitration in the presence of concentrated sulfuric acid. Anthanthron has a crystal structure with the space group P 2 1 / c (space group no. 14) .
use
Anthanthrone is unsubstituted and has no technical significance. Only 4,10-dibromoanthanthrone is used technically as a pigment and is one of the most lightfast and weatherproof organic pigments. The more yellowish 4,10-dichloranthanthrone is irrelevant as a pigment.
Individual evidence
- ↑ a b c d Ludwig Kalb: About Anthanthron. I. Communication. In: Reports of the German Chemical Society . 47, 1914, pp. 1724-1730, doi : 10.1002 / cber.19140470260 .
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ a b Hans Eduard Fierz-David: Artificial Organic Dyes Supplementary Volume . Springer-Verlag, 2013, ISBN 978-3-642-90894-1 , p. 98 ( limited preview in Google Book search).
- ↑ a b Entry on anthanthrone pigments. In: Römpp Online . Georg Thieme Verlag, accessed on March 28, 2016.
- ^ IAS Edwards, HP Stadler: The crystal structure of anthanthrone. In: Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 27, pp. 946-962, doi : 10.1107 / S0567740871003303 .