Dodecahydroxycyclohexane

Last updated
Dodecahydroxycyclohexane
Dodecahydroxycyclohexane-2D-skeletal.png
Dodecahydroxycyclohexane-from-dihydrate-xtal-CM-3D-ellipsoids.png
Sample of cyclohexanehexone octahydrate.jpg
Names
Preferred IUPAC name
Cyclohexanedodecol
Other names
Dodecahydroxycyclohexane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H Yes check.svgY
    Key: MZIPHGCOJCDHPI-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H
    Key: MZIPHGCOJCDHPI-UHFFFAOYAW
  • OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)(O)C1(O)O
Properties
(C(OH)2)6
Molar mass 276.150 g·mol−1
AppearanceColourless crystals (dihydrate)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Dodecahydroxycyclohexane is an organic compound with molecular formula C6O12H12 or C6(OH)12 or (C(OH)2)6. It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone (C6O6).

Contents

Dihydrate

The dihydrate C6O12H12·2H2O can be crystallized from methanol as colorless plates or prisms, that decomposes at about 100 °C. [1]

Thermal ellipsoid model of the molecular cell of dodecahydroxycyclohexane dihydrate Dodecahydroxycyclohexane-dihydrate-from-xtal-CM-3D-ellipsoids.png
Thermal ellipsoid model of the molecular cell of dodecahydroxycyclohexane dihydrate

This compound was synthesized by Joseph Udo Lerch (1816–1892) in 1862 [2] by oxidation of benzenehexol C6(OH)6 or tetrahydroxy-p-benzoquinone C6(OH)4O2 and characterized by Rudolf Nietzki and Theodor Benckiser  [ de ] in 1885, [3] although the product was for a long time assumed to be hexaketocyclohexane with water of crystallization (C6O6·8H2O).

Indeed, this product is still commonly marketed as cyclohexanehexone octahydrate, hexaketocyclohexane octahydrate, triquinoyl octahydrate and similar names. Its true nature was suspected since the 1950s or earlier, [4] but was confirmed by X-ray diffraction analysis only in 2005. [5]

See also

References

  1. ↑ Alexander J. Fatiadi; Horace S. Isbell; William F. Sager (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 2009-03-22.
  2. ↑ Jos. Ud. Lerch (1862). "Ueber Kohlenoxydkalium und die aus demselben darstellbaren Säuren". Journal für Praktische Chemie. 87 (1): 427–469. doi:10.1002/prac.18620870146.
  3. ↑ 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.
  4. ↑ Willis B. Person and Dale G. Williams (1957). "Infrared spectra and the structures of leuconic acid and triquinoyl". J. Phys. Chem. 61 (7): 1017–1018. doi:10.1021/j150553a047.
  5. ↑ Thomas M. Klapötke; Kurt Polborn; Jan J. Weigand (March 2005). "Dodecahydroxycyclohexane dihydrate" (PDF). Acta Crystallographica E. Archived from the original (PDF) on 2020-03-04.
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