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Analysis of 2,6-substituted cyclohexanones and phenols by gas-chromatography combined with thin-layer chromatography

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Summary

Under certain conditions auto-condensation of cyclohexanone can yield a mixture of cis-2,6-di(cyclohexen-1-yl)cyclohexanone and its (stereo) isomers. It is shown by TLC that in the thermal as well as the acid-catalyzed and the basecatalyzed reaction only interconversion of these ketones takes place. Treatment with a palladium catalyst gives rise to complicated mixtures of many structurally similar 2,6-disubstituted cyclohexanones and phenols. A description is given of the analysis of these mixtures by means of GLC coupled with TLC.

Zusammenfassung

Autokondensation von Cyclohexanon kann unter bestimmten Umständen ein Gemisch von Cis-2,6-di(cyclohexen-1-yl)cyclohexanon und dessen (Stereo)-Isomeren ergeben. Mittels Dünnschicht-Chromatographie wird gezeigt, daß diese Verbindungen sowohl bei Erhitzung als auch bei Anwesenheit von Säuren und Basen ineinander übergehen. Behandlung mit einem Palladium-Katalysator ergibt komplizierte Gemische vieler in struktureller Hinsicht ähnlicher 2,6-disubstituierter Cyclohexanone und Phenole. Die Analyse dieser Gemische mit Hilfe einer kombinierten Anwendung von Gas- und Dünnschicht-Chromatographie wird beschrieben.

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Authors and Affiliations

  1. Central Research Institute of AKU and affiliated Companies, Arnhem, The Netherlands

    B. H. Bibo & H. L. Louwerse

  2. Algemene Kunstzijde Unie N.V. Velperweg 76, Arnhem, Holland

    B. H. Bibo

Authors
  1. B. H. Bibo
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  2. H. L. Louwerse
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Bibo, B.H., Louwerse, H.L. Analysis of 2,6-substituted cyclohexanones and phenols by gas-chromatography combined with thin-layer chromatography. Z. Anal. Chem. 236, 208–215 (1968). https://doi.org/10.1007/BF00503275

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  • DOI: https://doi.org/10.1007/BF00503275

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