Английская Википедия:Benzenehexol
Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula Шаблон:Chem or Шаблон:Chem. It is a six-fold phenol of benzene.[1][2] The product is also called hexaphenol,[3] but this name has been used also for other substances.[4]
Benzenehexol is a crystalline solid soluble in hot water,[3] with a melting point above 310°.[1] It can be prepared from inositol (cyclohexanehexol). Oxidation of benzenehexol yields tetrahydroxy-p-benzoquinone (THBQ), rhodizonic acid, and dodecahydroxycyclohexane.[5] Conversely, benzenehexol can be obtained by reduction of sodium THBQ salt with SnCl2/HCl.[6]
Benzenehexol is a starting material for a class of discotic liquid crystals.[6]
Benzenehexol forms an adduct with 2,2'-bipyridine, with 1:2 molecular ratio.[7]
Benzenehexolate
Like most phenols, benzenehexol can lose the six H+ ions from the hydroxyl groups, yielding the hexaanion Шаблон:Chem. The potassium salt of this anion is one of the components of Liebig's so-called "potassium carbonyl", the product of the reaction of carbon monoxide with potassium. The hexaanion is produced by trimerization of the acetylenediolate anion Шаблон:Chem when heating potassium acetylenediolate Шаблон:Chem.[8] The nature of Шаблон:Chem was clarified by R. Nietzki and T. Benckiser in 1885, who found that its hydrolysis yielded benzenehexol.[9][10][11]
The lithium salt of this anion, Li6C6O6 has been considered for electric battery applications.[12]
Esters
Hexahydroxy benzene forms esters such as the hexaacetate Шаблон:Chem(-O(CO)CH3)6 (melting point 220 °C) and ethers like hexa-tert-butoxybenzene Шаблон:Chem(-OC(CH3)3)6 (melting point 223 °C).[8]
References
- ↑ 1,0 1,1 Шаблон:Cite web
- ↑ Шаблон:Citation
- ↑ 3,0 3,1 Шаблон:Cite book
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite journal
- ↑ 6,0 6,1 Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ 8,0 8,1 Шаблон:Cite journal
- ↑ R. Nietzki and T. Benckiser (1885), Berichte Chemie, volume 18, page 1834. Cited by Fatiadi and Sanger.
- ↑ Ludwig Mond (1892), On metallic carbonyls. Proceedings of the Royal Institution, volume 13, pages 668-680. Reprinted in The Development of Chemistry, 1789-1914: Selected essays edited by D. Knight (1998). Шаблон:ISBN Online version at books.google.com, accessed on 2010-01-15.
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal