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Production of cyclic alcohols

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Abstract

Cyclic alcohols are important starting materials for production of many chemical specialties. Cyclohexanol is an intermediate in adipic acid and ε-caprolactam technologies and it is also used as a solvent in chemical production. Cyclopentanol is often used in textile industry and in fragrances or fungicides production. Cyclic alcohols are manufactured by various processes and all of them have their limitations. Oxidation of cyclohexane is problematic due to the bad selectivity and low conversion level. Hydrogenation of phenol suffers from a high price of the starting feedstock. In recent years, some researchers have started to focus on direct and indirect hydrations of cyclic alkenes. The aim of this short review is to present the established methods and to summarize the published articles dealing with the hydration of cyclic alkenes. The direct hydration over zeolite catalysts and the indirect hydration in the presence of formic acid are widely described.

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Fig. 1
Fig. 2

Reprinted from Katariya et al. 2009 with permission from American Chemical Society

Fig. 3

Reprinted from Ahamed Imam et al. 2013 with permission from American Chemical Society

Fig. 4

Reprinted from Zhang et al. 2002 with permission from Elsevier

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Abbreviations

VLE:

Vapor–liquid equilibrium

LLE:

Liquid–liquid equilibrium

RCM:

Residual curve maps

Da :

Damköhler number

NRTL:

Non-random two-liquid

CHOL:

Cyclohexanol

MCP:

Methylcyclopentenes

DCHE:

Dicyclohexyl ether

CHCH:

1-Cyclohexylcyclohexene

3MCP:

3-Methylcyclopentene

CPOL:

Cyclopentanol

CPEON:

Cyclopent-2-en-1-one

DCPE:

Dicyclopentyl ether

CEYCP:

1-Cyclopent-2-en-1-ylcyclopentene

CPCP:

1-Cyclopentylcyclopentene

CNTs:

Carbon nanotubes

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Acknowledgements

This work was realized within the Operational Programme Prague–Competitiveness (CZ.2.16/3.1.00/24501) and “National Program of Sustainability” (NPU I LO1613 MSMT-43760/2015) and also financially supported from specific university research (MSMT No 21-SVV/2018). We, the authors, would like to gratefully thank to prof. Ing. Josef Pašek, DrSc. for his expert comments from the field of chemical technology and process engineering.

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  1. Department of Organic Technology, University of Chemistry and Technology Prague, Technická 5, 166 28, Prague 6, Czech Republic

    Tomáš Sommer, Martin Zapletal & Jiří Trejbal

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  1. Tomáš Sommer
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  2. Martin Zapletal
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Correspondence to Jiří Trejbal.

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Sommer, T., Zapletal, M. & Trejbal, J. Production of cyclic alcohols. Chem. Pap. 72, 2397–2412 (2018). https://doi.org/10.1007/s11696-018-0508-5

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