upcScavenger » Polyphenols » Wiki: Benzenehexol

Benzenehexol

( Polyphenols )

Anion Benzenehexol Potassium Salt

Rank: 100%

Wiki
Comments
Media

Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula or . It is a six-fold Phenols of benzene. The product is also called hexaphenol,

(1996). 9780412540905, Chapman & Hall; CRC Press. ISBN 9780412540905

but this name has been used also for other substances.

Benzenehexol is a crystalline solid soluble in hot water, with a melting point above 310°. It can be prepared from inositol (cyclohexanehexol). Oxidation of benzenehexol yields tetrahydroxy- p-benzoquinone (THBQ), rhodizonic acid, and dodecahydroxycyclohexane. Conversely, benzenehexol can be obtained by reduction of sodium THBQ salt with SnCl₂/HCl.

Benzenehexol is a starting material for a class of liquid crystals.

Benzenehexol forms an adduct with 2,2'-bipyridine, with 1:2 molecular ratio.

Benzenehexolate

Like most phenols, benzenehexol can lose the six proton ions from the hydroxyl groups, yielding the anion . 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 when heating potassium acetylenediolate . The nature of was clarified by Rudolf Nietzki and in 1885, who found that its hydrolysis yielded benzenehexol.

 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).  [https://books.google.com/books?id=F7XSYSB1-NYC&pg=PA326 Online version] at books.google.com, accessed on 2010-01-15.

The lithium salt of this anion, Li₆C₆O₆ has been considered for electric battery applications.

Esters

Hexahydroxy benzene forms esters such as the hexaacetate (-O(CO)CH₃)₆ (melting point 220 °C) and ethers like hexa-tert-butoxybenzene (-OC(CH₃)₃)₆ (melting point 223 °C).

Categories: Polyphenols