Cyclohexanone: The Main Methods of Obtaining and Extracting Target Products from a Reaction Mixture

Maevskii, M. A.; Oshanina, I. V.; Фролкова, А. К.

doi:10.1134/s0040579518040097

Cited by 11 publications

(10 citation statements)

References 12 publications

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“…1 New technology for its production is currently being developed. 2,3 Cyclohexene is preferred as a raw material among many others due to the mild conditions of chemical transformation (atmospheric pressure, low temperatures, absence of byproducts). 4,5 The key problem was the choice of solvent for the olefin oxidation.…”

Section: Introductionmentioning

confidence: 99%

Liquid–Liquid Equilibrium and Solubility for Ternary Systems Cyclohexene (Cyclohexanone) + Water + 1-Methylpyrrolidin-2-one (N,N-Dimethylacetamide) at 295.15 K and 99.32 kPa

Жучков

Фролкова

2022

J. Chem. Eng. Data

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The liquid–liquid equilibrium of ternary systems cyclohexene (cyclohexanone) + water + 1-methylpyrrolidin-2-one (N,N-dimethylacetamide) was studied experimentally to assess the possibility of separating the mixture of cyclohexanone production. Bachman and Hand equations were used to test the correlation of the experimental data. The solubility was measured using a “cloud-point” technique method, and the data on compositions of liquid phases were determined by GLC analysis. Experimental data were correlated using the nonrandom two-liquid model. Calculated results were found to be in sufficient agreement with experimental data. The topological structure of the phase diagram is discussed. Recommendations for conducting a chemical reaction are formulated, and a flowsheet for separating the reaction mixture is proposed. The efficiency of the flowsheet is confirmed by the simulation of the distillation process.

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Section: Introductionmentioning

confidence: 99%

Liquid–Liquid Equilibrium and Solubility for Ternary Systems Cyclohexene (Cyclohexanone) + Water + 1-Methylpyrrolidin-2-one (N,N-Dimethylacetamide) at 295.15 K and 99.32 kPa

Жучков

Фролкова

2022

J. Chem. Eng. Data

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“…Cyclohexanone (CHON) is a raw material for producing adipic acid, caprolactam, polyamides nylon-6, and nylon-66. − The literature review showed that the majority of CHON (about 60% of the world production) is produced by oxidation of cyclohexane because of the low cost of raw materials. However, this method has several disadvantages such as low conversion of the feedstock and the selectivity of CHON formation.…”

Section: Introductionmentioning

confidence: 99%

“…To overcome this limitation a low-pressure distillation is used. Besides, this process is quite energy-intensive. , …”

Section: Introductionmentioning

confidence: 99%

“…Besides, this process is quite energy-intensive. 7,8 One of the promising methods is the oxidation of cyclohexene (CHEN) to CHON with n-benzoquinone in water-organic solutions of cationic complexes of palladium-(II). 9,10 This process is characterized by high parameters of chemical reaction (conversion, selectivity) as well as soft conditions (298−373 K, atmospheric pressure).…”

Section: Introductionmentioning

confidence: 99%

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Phase Equilibrium of Systems Cyclohexene + Water + Cyclohexanone + N-Methyl-2-pyrrolidone (+Acetonitrile)

2019

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The paper presents the results of the study of phase equilibrium in the system formed in the reaction of cyclohexene oxidation (cyclohexene + water + cyclohexanone + solvent). Pure N-methyl-2-pyrrolidone or binary mixture acetonitrile + Nmethyl-2-pyrrolidone was considered as a solvent. The method of studying was mathematical modeling on the base of the nonrandom two-liquid model. Thermodynamic-topological analysis was used to analyze the structure of the vapor−liquid equilibrium diagram. The mixture separation flowsheets were proposed and parameters of column work were determined using simulation in Aspen Plus V.10.0. The possibility of isolation of the target component (cyclohexanone) without the use of special separation methods was proved. The results obtained showed the prospects of replacement of pure acetonitrile or previously proposed dimethylsulfoxide and dimethylacetamide by solvents considered.

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“…Cyclohexanone (CHON) is one the important products in the technology of organic and petrochemical synthesis. The majority of cyclohexanone (95%) is an intermediate in processes for producing adipic acid, caprolactam, polyamides nylon-6, and nylon-66. − There are different methods of obtaining cyclohexanone: oxidation of cyclohexane, phenol hydrogenation, dehydrogenation and oxidation of cyclohexanol, the oxidation of cyclohexene. The industrial methods are oxidation of cyclohexane (American company DuPont), obtaining CHON from phenol (a Dutch company DSM), and oxidation of cyclohexanol (a Japanese company Asahi).…”

Section: Introductionmentioning

confidence: 99%

Analysis of Phase Equilibrium Diagrams of Cyclohexene + Water + Cyclohexanone + Solvent System

Фролкова¹,

Mayevskiy²,

Фролкова³

2018

J. Chem. Eng. Data

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Vapor−liquid and liquid−liquid equilibrium of quaternary systems that can form in the production of cyclohexanone by oxidation of cyclohexene in the presence of different solvents water + dimethylformamide (dimethyl sulfoxide, dimethylacetamide) were studied using mathematic modeling and NRTL model. The experimental and calculated data were found to be in a good agreement. The analysis of phase diagrams showed that the simplest diagram (two binary szeotropes and one distillation region) is observed for systems containing dimethyl sulfoxide and dimethylacetamide. It makes possible to separate cyclohexanone from catalyst and high boiling solvents by distillation.

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Cyclohexanone: The Main Methods of Obtaining and Extracting Target Products from a Reaction Mixture

Cited by 11 publications

References 12 publications

Liquid–Liquid Equilibrium and Solubility for Ternary Systems Cyclohexene (Cyclohexanone) + Water + 1-Methylpyrrolidin-2-one (N,N-Dimethylacetamide) at 295.15 K and 99.32 kPa

Liquid–Liquid Equilibrium and Solubility for Ternary Systems Cyclohexene (Cyclohexanone) + Water + 1-Methylpyrrolidin-2-one (N,N-Dimethylacetamide) at 295.15 K and 99.32 kPa

Phase Equilibrium of Systems Cyclohexene + Water + Cyclohexanone + N-Methyl-2-pyrrolidone (+Acetonitrile)

Analysis of Phase Equilibrium Diagrams of Cyclohexene + Water + Cyclohexanone + Solvent System

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