A comprehensive and updated review of studies on the oxidation of cyclohexane to produce ketone-alcohol (KA) oil
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Ahmed Abutaleb
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.
Acknowledgments
The authors would like to appreciate the support of Jazan University, Gizan, Saudi Arabia for this publication.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: None declared.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
Glossary and acronyms
- C=O
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cyclohexanone (C6H10O); a product of cyclohexane oxidation
- C3N4
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carbon nitride; used as catalyst support
- C6H12
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cyclohexane; the substrate or feedstock for producing KA oil by oxidation
- CH2Cl2
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dichloromethane; used as the solvent
- CH3CN
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acetonitrile; used as the solvent
- CHHP
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cyclohexylhydroperoxide; a product of cyclohexane oxidation
- C–OH
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cyclohexanol (C6H12O); a product of cyclohexane oxidation
- FDU-12
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three-dimensional mesoporous material with a superior 3D channel; used as catalyst support
- KA oil
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mixture of cyclohexanol and cyclohexanone
- KIT-6
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mesoporous silica molecular sieve; used as catalyst support
- MNPs
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magnetite nanoparticles
- MPTMS
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3-mercapto(propyl)trimethoxysilane
- MW
-
microwave
- NGO
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nanographene oxide; used as catalyst support
- NHPI
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N-hydroxyphthalimide; used as an additive
- Nylon 6
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polycaprolactam, a semi-crystalline polyamide
- Nylon 6,6
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made from the polymerization of adipoyl chloride and hexamethylene diamine
- PhI(OAc)2
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iodobenzene diacetate; used as an oxidant
- PhIO
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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
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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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Articles in the same Issue
- Frontmatter
- In this issue
- Ignition–extinction analysis of catalytic reactor models
- A comprehensive and updated review of studies on the oxidation of cyclohexane to produce ketone-alcohol (KA) oil
- Polyoxadiazoles as proton exchange membranes for fuel cell application
- Synthesis and applications of surface-modified magnetic nanoparticles: progress and future prospects
- Advances in absorbents and techniques used in wet and dry FGD: a critical review
- Carbomer microgels as model yield-stress fluids
Articles in the same Issue
- Frontmatter
- In this issue
- Ignition–extinction analysis of catalytic reactor models
- A comprehensive and updated review of studies on the oxidation of cyclohexane to produce ketone-alcohol (KA) oil
- Polyoxadiazoles as proton exchange membranes for fuel cell application
- Synthesis and applications of surface-modified magnetic nanoparticles: progress and future prospects
- Advances in absorbents and techniques used in wet and dry FGD: a critical review
- Carbomer microgels as model yield-stress fluids