Benzenehexol, also calledhexahydroxybenzene, is anorganic compound with formulaC 6H 6O 6 orC 6(OH) 6. It is a six-foldphenol ofbenzene.[2][3] The product is also calledhexaphenol,[4] but this name has been used also for other substances.[5]
Like most phenols, benzenehexol can lose the sixH+ ions from thehydroxyl groups, yielding thehexaanionC 6O6− 6. Thepotassium salt of this anion is one of the components ofLiebig's so-called "potassium carbonyl", the product of the reaction ofcarbon monoxide with potassium. The hexaanion is produced by trimerization of theacetylenediolate anionC 2O2− 2 when heating potassium acetylenediolateK 2C 2O 2.[9] The nature ofK 6C 6O 6 was clarified[10] byRudolf Nietzki andTheodor Benckiser [de] in 1885, who found that itshydrolysis yielded benzenehexol.[11][12]
Hexahydroxy benzene forms esters such as the hexaacetateC 6(-O(CO)CH3)6 (melting point 220 °C) and ethers likehexa-tert-butoxybenzeneC 6(-OC(CH3)3)6 (melting point 223 °C).[9]
^Cowan John A., Howard Judith A. K., Leech Michael A., Puschmann Horst, Williams Ian D. (2001). "Hexahydroxybenzene—2,2'-bipyridine (1/2)".Acta Crystallographica Section C.57 (10):1194–1195.doi:10.1107/S0108270101011350.PMID11600782.S2CID25797464.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^abSerratosa Fèlix (1983). "Acetylene Diethers: A Logical Entry to Oxocarbons".Acc. Chem. Res.16 (5):170–176.doi:10.1021/ar00089a004.
^ Ludwig Mond (1892),On metallic carbonyls. Proceedings of the Royal Institution, volume 13, pages 668-680. Reprinted inThe Development of Chemistry, 1789-1914: Selected essays edited by D. Knight (1998).ISBN0-415-17912-2Online version at books.google.com, accessed on 2010-01-15.
^Büchner Werner, Weiss E (1964). "Zur Kenntnis der sogenannten "Alkalicarbonyle" IV[1] Über die Reaktion von geschmolzenem Kalium mit Kohlenmonoxid".Helvetica Chimica Acta.47 (6):1415–1423.doi:10.1002/hlca.19640470604.
^Chen Haiyan, Armand Michel, Courty Matthieu, Jiang Meng, Grey Clare P., Dolhem Franck, Tarascon Jean-Marie, Poizot Philippe (2009). "Lithium Salt of Tetrahydroxybenzoquinone: Toward the Development of a Sustainable Li-Ion Battery".J. Am. Chem. Soc.131 (25):8984–8988.doi:10.1021/ja9024897.PMID19476355.{{cite journal}}: CS1 maint: multiple names: authors list (link)
