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Benzenehexol
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<h2 id="benzenehexolate">Benzenehexolate</h2> <p>Like most phenols, benzenehexol can lose the six <a href="/facts/Proton/clCjepXP">H+</a> ions from the <a href="/facts/Hydroxyl/1Hs2QAEv">hydroxyl</a> groups, yielding the <a href="/facts/Anion/wrbwhF3z">hexaanion</a> C6O6−6. The <a href="/facts/Potassium/FWPwS7Rj">potassium</a> salt of this anion is one of the components of <a href="/facts/Justus_von_Liebig/0vKzMlDA">Liebig</a>'s so-called "potassium carbonyl", the product of the reaction of <a href="/facts/Carbon_monoxide/CKuLtEMJ">carbon monoxide</a> with potassium. The hexaanion is produced by trimerization of the <a href="/facts/Acetylenediolate/WrxxmWm9">acetylenediolate</a> anion C2O2−2 when heating potassium acetylenediolate K2C2O2.<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a> The nature of K6C6O6 was clarified<a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> by <a href="/facts/Rudolf_Nietzki/DEyDHHjr">Rudolf Nietzki</a> and Theodor Benckiser [de] in 1885, who found that its <a href="/facts/Hydrolysis/JTvwIHPs">hydrolysis</a> yielded benzenehexol.<a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a><a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a> </p><p>The <a href="/facts/Lithium/7vXX6BWA">lithium</a> salt of this anion, Li6C6O6 has been considered for <a href="/facts/Electric_battery/bqEpm4ue">electric battery</a> applications.<a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a> </p> <h2 id="esters">Esters</h2> <p>Hexahydroxy benzene forms esters such as the hexaacetate C6(-O(CO)CH3)6 (melting point 220 °C) and ethers like hexa-tert-butoxybenzene C6(-OC(CH3)3)6 (melting point 223 °C).<a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a> </p> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Fatiadi, Alexander J.; Sager, William F. "Hexahydroxybenzene (Benzenehexol)". Organic Syntheses. Retrieved 2023-01-28. <a href="https://orgsyn.org/demo.aspx?prep=cv5p0595" target="_blank">https://orgsyn.org/demo.aspx?prep=cv5p0595</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Leston, Gerd (2000-12-04), "(Polyhydroxy)benzenes", in John Wiley & Sons, Inc. (ed.), Kirk-Othmer Encyclopedia of Chemical Technology, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. 1615122512051920.a01, doi:10.1002/0471238961.1615122512051920.a01, ISBN 978-0-471-23896-6, retrieved 2023-01-28 <a href="978-0-471-23896-6" target="_blank">978-0-471-23896-6</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Codagan, J.I.G.; Buckingham, John; MacDonald, Finlay J.; Rhodes, P. H. (1996). Dictionary of Organic Compounds, 6th edition. London: Chapman & Hall; CRC Press. ISBN 9780412540905. OCLC 35716592. <a href="9780412540905" target="_blank">9780412540905</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>"Hexaphenol (CAS: 1506-76-9)". www.chemicalbook.com. Retrieved 2009-07-05. <a href="https://www.chemicalbook.com/ProductChemicalPropertiesCB7111482_EN.htm" target="_blank">https://www.chemicalbook.com/ProductChemicalPropertiesCB7111482_EN.htm</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Codagan, J.I.G.; Buckingham, John; MacDonald, Finlay J.; Rhodes, P. H. (1996). Dictionary of Organic Compounds, 6th edition. London: Chapman & Hall; CRC Press. ISBN 9780412540905. OCLC 35716592. <a href="9780412540905" target="_blank">9780412540905</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Fatiadi, Alexander J.; Sager, William F. "Hexahydroxybenzene (Benzenehexol)". Organic Syntheses. Retrieved 2023-01-28. <a href="https://orgsyn.org/demo.aspx?prep=cv5p0595" target="_blank">https://orgsyn.org/demo.aspx?prep=cv5p0595</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Fatiadi, Alexander J.; Isbell, Horace S.; Sager, William F. (March–April 1963). "Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)" (PDF). Journal of Research of the National Bureau of Standards Section A. 67A (2): 153–162. doi:10.6028/jres.067A.015. PMC 6640573. PMID 31580622. Archived from the original (PDF) on 2009-03-25. Retrieved 2009-07-05. <a href="https://web.archive.org/web/20090325204012/http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf" target="_blank">https://web.archive.org/web/20090325204012/http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Kumar, Sandeep (2006). "Self-organization of disc-like molecules: chemical aspects". Chemical Society Reviews. 35 (1): 83–109. doi:10.1039/b506619k. PMID 16365644. <a href="https://pubs.rsc.org/en/content/articlelanding/2006/cs/b506619k" target="_blank">https://pubs.rsc.org/en/content/articlelanding/2006/cs/b506619k</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Kumar, Sandeep (2006). "Self-organization of disc-like molecules: chemical aspects". Chemical Society Reviews. 35 (1): 83–109. doi:10.1039/b506619k. PMID 16365644. <a href="https://pubs.rsc.org/en/content/articlelanding/2006/cs/b506619k" target="_blank">https://pubs.rsc.org/en/content/articlelanding/2006/cs/b506619k</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>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. PMID 11600782. S2CID 25797464.{{cite journal}}: CS1 maint: multiple names: authors list (link) <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Serratosa Fèlix (1983). "Acetylene Diethers: A Logical Entry to Oxocarbons". Acc. Chem. Res. 16 (5): 170–176. doi:10.1021/ar00089a004. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>R. Nietzki; Th. Benckiser (1885). "Ueber Hexaoxybenzolderivate und ihre Beziehungen zur Krokonsäure und Rhodizonsäure". Berichte der Deutschen Chemischen Gesellschaft (in German). 18 (1): 499–515. doi:10.1002/CBER.188501801110. ISSN 0365-9496. Wikidata Q56853054. <a href="https://books.google.com/books?id=4yFKAQAAMAAJ&pg=PA499" target="_blank">https://books.google.com/books?id=4yFKAQAAMAAJ&pg=PA499</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>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). ISBN 0-415-17912-2 Online version at books.google.com, accessed on 2010-01-15. <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></p></li> <li id="fn:15"><p>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. PMID 19476355.{{cite journal}}: CS1 maint: multiple names: authors list (link) <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></p></li> <li id="fn:16"><p>Serratosa Fèlix (1983). "Acetylene Diethers: A Logical Entry to Oxocarbons". Acc. Chem. Res. 16 (5): 170–176. doi:10.1021/ar00089a004. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:16" class="footnote-back-ref">↩</a></p></li> </ol>