Hexahydroxybenzene
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| Surname | Hexahydroxybenzene | ||||||||||||||||||
| Molecular formula | C 6 H 6 O 6 | ||||||||||||||||||
| Brief description |
white to yellowish solid |
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| properties | |||||||||||||||||||
| Molar mass | 174.11 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
310 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Hexahydroxybenzene is an organic substance with the empirical formula C 6 H 6 O 6 . It is in crystalline form at room temperature and dissolves in hot water.
history
It was first found in the form of its hexapotassium salt by Justus von Liebig in attempts to convert carbon monoxide with potassium in 1834. By passing carbon monoxide over molten potassium, he came up with a substance with the empirical formula KCO, which he called carbon oxide potassium, but which he did not recognize as the salt of hexahydroxybenzene. B. Nietzki and T. Benckiser clarified the structure in 1885, they obtained hexahydroxybenzene by hydrolysis of the material.
Manufacturing
Hexahydroxybenzene, by dehydration of inositol are obtained. Another way is the reduction of the sodium salt of 2,3,5,6-tetrahydroxy- 1,4-benzoquinone with tin (II) chloride and hydrochloric acid .
Reactions
The oxidation of hexahydroxybenzene leads to 2,3,5,6-tetrahydroxy-1,4-benzoquinone (THBQ), rhodizonic acid and dodecahydroxycyclohexane . It forms adducts with 2,2′-bipyridine in a molar ratio of 1: 2. It is converted by alkali metals into its sixfold negatively charged anion C 6 O 6 6− . It forms hexaesters with acids such as acetic acid .
Individual evidence
- ↑ a b c d Entry on hexahydroxybenzene at TCI Europe, accessed on March 3, 2014.
- ↑ Alexander J. Fatiadi, WF Sager: Hexahydroxybenzene (Benzenehexol) In: Organic Syntheses . 42, 1962, p. 66, doi : 10.15227 / orgsyn.042.0066 ; Coll. Vol. 5, 1973, p. 595 ( PDF ).
- ^ WE Trout: The metal carbonyls. In: J. Chem. Educ. 1937, 14 (10), p. 453 ( doi : 10.1021 / ed014p453 ).
- ↑ WA Herrmann : 100 years of metal carbonyls. A chance discovery makes history. In: Chemistry in Our Time . 1988, 22nd year, No. 4, pp. 113-122 ( doi : 10.1002 / ciuz.19880220402 ).
- ↑ W. Büchner, E. Weiss: On the knowledge of the so-called "alkali carbonyls". About the reaction of molten potassium with carbon monoxide. In: Helvetica Chimica Acta . 47, 1964, pp. 1415-1423 ( doi : 10.1002 / hlca.19640470604 ).
- ↑ Alexander J. Fatiadi, Horace S. Isbell, William F. Sager: Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol). In: Journal of Research of the National Bureau of Standards Section a-Physics and Chemistry , vA 67 (1963): pp. 153–158 ( PDF ).
- ↑ John A. Cowan, Judith AK Howard, Michael A. Leech, Horst Puschmann, Ian D. Williams: Hexahydroxybenzene-2,2'-bipyridine (1/2). In: Acta Crystallographica Section C: Crystal Structure Communications . 57, 2001, pp. 1194-1195 ( doi : 10.1107 / S0108270101011350 ).