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A comprehensive and updated review of studies on the oxidation of cyclohexane to produce ketone-alcohol (KA) oil

  • Ahmed Abutaleb and Mohammad Ashraf Ali
Published/Copyright: April 12, 2021
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Abstract

Oxidation of cyclohexane is an essential chemical reaction for the industrial manufacture of cyclohexanol and cyclohexanone. These two compounds, together known as ketone–alcohol (KA) oil, are the main feedstock for nylon 6 and nylon 6,6 productions. Several types of catalysts and reaction conditions have been used for cyclohexane oxidation. This paper presents a thorough literature review of catalytic materials used for cyclohexane oxidation to produce KA oil using oxygen, air and other oxidizing agents as well as utilizing different solvents. This review covers research and development reported over the years 2014–2020. This review aims to comprehend the type of catalysts, solvents, oxidants and other reaction parameters used for the oxidation of cyclohexane. Three types of cyclohexane oxidation processes namely thermocatalytic, photocatalytic and microwave-assisted catalytic have been reported. The results of the review showed that metal and metal oxide loaded silica catalysts performed excellently and provided high selectivity of KA oil and cyclohexane conversion. The use of peroxides is not feasible due to their high price compared to air and oxygen. Gold nanoparticles supported on silica performed with high selectivity and good conversion. The use of hydrochloric acid as an additive was found very effective to enhance the photocatalytic oxidation of cyclohexane. Water on the catalyst surface enhanced the reactivity of the photocatalysts since it helps in the generation of hydroxyl radicals.


Corresponding author: Mohammad Ashraf Ali, Chemical Engineering Department, College of Engineering, Jazan University, Gizan 45142, Saudi Arabia, E-mail:

Acknowledgments

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

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

Glossary and acronyms

C=O

cyclohexanone (C6H10O); a product of cyclohexane oxidation

C3N4

carbon nitride; used as catalyst support

C6H12

cyclohexane; the substrate or feedstock for producing KA oil by oxidation

CH2Cl2

dichloromethane; used as the solvent

CH3CN

acetonitrile; used as the solvent

CHHP

cyclohexylhydroperoxide; a product of cyclohexane oxidation

C–OH

cyclohexanol (C6H12O); a product of cyclohexane oxidation

FDU-12

three-dimensional mesoporous material with a superior 3D channel; used as catalyst support

KA oil

mixture of cyclohexanol and cyclohexanone

KIT-6

mesoporous silica molecular sieve; used as catalyst support

MNPs

magnetite nanoparticles

MPTMS

3-mercapto(propyl)trimethoxysilane

MW

microwave

NGO

nanographene oxide; used as catalyst support

NHPI

N-hydroxyphthalimide; used as an additive

Nylon 6

polycaprolactam, a semi-crystalline polyamide

Nylon 6,6

made from the polymerization of adipoyl chloride and hexamethylene diamine

PhI(OAc)2

iodobenzene diacetate; used as an oxidant

PhIO

iodosylbenzene; used as oxidant

PIMTS

mesoporous silica having high amounts of uniform tetrahedral framework titanium.

SBA-15

Santa Barbara Amorphous-15 was developed at the University of California, Santa Barbara.

sc-CO2

supercritical carbon dioxide; used as a solvent for cyclohexane oxidation

TBHP

tert-butylhydroperoxide; used as oxidant and pro-oxidant

TFA

trifluoroacetic acid; used to acidify the reaction mixture

TOF

Turnover frequency, moles of cyclohexane converted per mole of catalyst per reaction time

TON

Turnover number, moles of cyclohexane converted per mole of catalyst (mol C6H12/mol catalyst).

TUD-1

A mesoporous silicate first synthesized in 2001 at the Technische Universiteit Delft (TUD).

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Received: 2020-08-29
Accepted: 2021-01-19
Published Online: 2021-04-12
Published in Print: 2022-10-26

© 2021 Walter de Gruyter GmbH, Berlin/Boston

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