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An Updated Comprehensive Literature Review of Phenol Hydrogenation Studies

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Abstract

Cyclohexanone is an important industrial intermediate to produce nylons. The main industrial routes for cyclohexanone manufacture used cyclohexane and phenol as feedstock. The selective hydrogenation of phenol to cyclohexanone comprises one-step and two-step processes. This review presents a detailed analysis of the research findings available in the open literature for phenol hydrogenation to produce cyclohexanone and cyclohexanol and covers the research conducted during 2014–2020 using conventional and modern catalysts. This review aims to disseminate the knowledge of the current research conducted for phenol hydrogenation and provide a comprehensive resource for researchers working in this field. This review has included and discussed both methods of thermocatalytic and electrocatalytic hydrogenation of phenol. Most of the studies have used carbon or carbon–nitrogen supported catalysts loaded with Pd. The carbon and carbon–nitrogen materials were derived from different sources including polymers, activated carbon, and MOF. Oxygen treatment was found to produce highly active and stable catalysts. The high performance was found associated with the high surface area of the catalyst and uniformly dispersed metal nanoparticles. The acidic conditions exhibited an increase in catalyst performance. Alkali-promoted precious metal-loaded catalysts performed better than un-promoted catalysts.

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Abbreviations

Amberlyst-45:

Macroporous sulfonic acid-containing polymeric catalyst made of polystyrene sulfonate

CN:

N-doped carbon

C3N4 :

Carbon nitride

CH3CN:

Acetonitrile

C6H12 :

Cyclohexane

C–OH:

Cyclohexanol

C=O:

Cyclohexanone

KA oil:

Mixture of cyclohexanol and cyclohexanone

LDHs:

Layered double hydroxides

MNPs:

Magnetite nanoparticles

NPs:

Nanoparticles

NGO:

Nano graphene oxide

Nylon 6:

Made from the polymerization of caprolactam

Nylon 6,6:

Made from the polymerization of adipic acid and hexamethylene diamine

PVDF-HFP:

Poly(vinylidene fluoride)-hexafluoropropylene

SBA-15:

Santa Barbara Amorphous-15. Highly stable mesoporous silica sieve developed by researchers at the University of California at Santa Barbara

TFA:

Trifluoracetic acid

TNWs:

Titania nanowires

TOF:

Moles of phenol converted per mole of catalyst per reaction time

TON:

Moles of phenol converted per mole of catalyst

UiO-66:

Stands for Universiteteti Oslo-66. Regarded as a typical MOF built of [Zr6O4(OH)4] octahedron clusters and 1,4-benzene dicarboxylic acid ligands

ZIF-67:

Zeolitic imidazolate framework-67. Formed by bridging 2-methylimidazolate anions and cobalt cations resulting in sodalite (SOD) topology with a pore size of about 0.34 nm

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Acknowledgements

The authors would like to appreciate the support of the Jazan University, Jazan, Saudi Arabia for this publication.

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  1. Chemical Engineering Department, College of Engineering, Jazan University, Jazan, 45142, Saudi Arabia

    Mohammad Ashraf Ali & Ahmed Abutaleb

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  1. Mohammad Ashraf Ali
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Ali, M.A., Abutaleb, A. An Updated Comprehensive Literature Review of Phenol Hydrogenation Studies. Catal Lett 152, 1555–1581 (2022). https://doi.org/10.1007/s10562-021-03714-5

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