Epoxidation of cyclohexene with cyclohexyl hydroperoxide
Objectives. To investigate the regularities of the process of joint production of epoxycyclohexane, cyclohexanol, and cyclohexanone using the cyclohexene epoxidation reaction with cyclohexyl hydroperoxide in the presence of an ammonium paramolybdate catalyst, representing an alternative to the metho...
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| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | Russian |
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MIREA - Russian Technological University
2024-01-01
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| Series: | Тонкие химические технологии |
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| Online Access: | https://www.finechem-mirea.ru/jour/article/view/2010 |
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| author | E. A. Kurganova A. S. Frolov S. A. Kanaev G. N. Koshel A. A. Petukhov G. V. Rybina V. V. Plakhtinskii V. S. Kabanova A. A. Smurova |
| author_facet | E. A. Kurganova A. S. Frolov S. A. Kanaev G. N. Koshel A. A. Petukhov G. V. Rybina V. V. Plakhtinskii V. S. Kabanova A. A. Smurova |
| author_sort | E. A. Kurganova |
| collection | DOAJ |
| description | Objectives. To investigate the regularities of the process of joint production of epoxycyclohexane, cyclohexanol, and cyclohexanone using the cyclohexene epoxidation reaction with cyclohexyl hydroperoxide in the presence of an ammonium paramolybdate catalyst, representing an alternative to the method of cyclohexanol and cyclohexanone synthesis by alkaline catalytic decomposition of cyclohexyl hydroperoxide.Methods. The qualitative and quantitative analysis of the obtained intermediate and target compounds was determined using modern physicochemical research methods: gas–liquid chromatography using the Chromatec-Crystal 5000.2 hardware and software complex with a flame ionization detector and infrared spectroscopy on an RX-1 infrared Fourier spectrometer. The content of hydroperoxide in the oxidation products was determined using iodometric titration, while the carboxylic acid content was determined by the titrimetric method based on the neutralization reaction.Results. The presented method for obtaining cyclohexanol and cyclohexanone together with epoxycyclohexane by the reaction of cyclohexene epoxidation with cyclohexyl hydroperoxide containing cyclohexane in the products of high-temperature liquid-phase oxidation is experimentally substantiated. The influence of various technological parameters on the process of liquid-phase oxidation of cyclohexane to hydroperoxide is described. The conditions for carrying out this reaction are determined to ensure the achievement of a content of cyclohexyl hydroperoxide of 1.5 wt % in the products of oxidation. The regularities of the epoxidation reaction of the synthesized cyclohexyl hydroperoxide with cyclohexene in the presence of an ammonium paramolybdate catalyst are analyzed.Conclusions. Epoxidation of cyclohexene with cyclohexyl hydroperoxide produced epoxycyclohexane at a yield of 80–90% and a conversion of cyclohexane hydroperoxide of 85%. |
| format | Article |
| id | doaj-art-63c72b177d22463db5fbae06e8a4785f |
| institution | DOAJ |
| issn | 2410-6593 2686-7575 |
| language | Russian |
| publishDate | 2024-01-01 |
| publisher | MIREA - Russian Technological University |
| record_format | Article |
| series | Тонкие химические технологии |
| spelling | doaj-art-63c72b177d22463db5fbae06e8a4785f2025-08-20T02:59:43ZrusMIREA - Russian Technological UniversityТонкие химические технологии2410-65932686-75752024-01-0118650551610.32362/2410-6593-2023-18-6-505-5161736Epoxidation of cyclohexene with cyclohexyl hydroperoxideE. A. Kurganova0A. S. Frolov1S. A. Kanaev2G. N. Koshel3A. A. Petukhov4G. V. Rybina5V. V. Plakhtinskii6V. S. Kabanova7A. A. Smurova8Yaroslavl State Technical UniversityYaroslavl State Technical UniversityKuibyshevAzotYaroslavl State Technical UniversityKazan National Research Technological UniversityYaroslavl State Technical UniversityYaroslavl State Technical UniversityYaroslavl State Technical UniversityYaroslavl State Technical UniversityObjectives. To investigate the regularities of the process of joint production of epoxycyclohexane, cyclohexanol, and cyclohexanone using the cyclohexene epoxidation reaction with cyclohexyl hydroperoxide in the presence of an ammonium paramolybdate catalyst, representing an alternative to the method of cyclohexanol and cyclohexanone synthesis by alkaline catalytic decomposition of cyclohexyl hydroperoxide.Methods. The qualitative and quantitative analysis of the obtained intermediate and target compounds was determined using modern physicochemical research methods: gas–liquid chromatography using the Chromatec-Crystal 5000.2 hardware and software complex with a flame ionization detector and infrared spectroscopy on an RX-1 infrared Fourier spectrometer. The content of hydroperoxide in the oxidation products was determined using iodometric titration, while the carboxylic acid content was determined by the titrimetric method based on the neutralization reaction.Results. The presented method for obtaining cyclohexanol and cyclohexanone together with epoxycyclohexane by the reaction of cyclohexene epoxidation with cyclohexyl hydroperoxide containing cyclohexane in the products of high-temperature liquid-phase oxidation is experimentally substantiated. The influence of various technological parameters on the process of liquid-phase oxidation of cyclohexane to hydroperoxide is described. The conditions for carrying out this reaction are determined to ensure the achievement of a content of cyclohexyl hydroperoxide of 1.5 wt % in the products of oxidation. The regularities of the epoxidation reaction of the synthesized cyclohexyl hydroperoxide with cyclohexene in the presence of an ammonium paramolybdate catalyst are analyzed.Conclusions. Epoxidation of cyclohexene with cyclohexyl hydroperoxide produced epoxycyclohexane at a yield of 80–90% and a conversion of cyclohexane hydroperoxide of 85%.https://www.finechem-mirea.ru/jour/article/view/2010cyclohexenecyclohexanecyclohexyl hydroperoxidecyclohexanonecyclohexanolliquid phase oxidationepoxidation |
| spellingShingle | E. A. Kurganova A. S. Frolov S. A. Kanaev G. N. Koshel A. A. Petukhov G. V. Rybina V. V. Plakhtinskii V. S. Kabanova A. A. Smurova Epoxidation of cyclohexene with cyclohexyl hydroperoxide Тонкие химические технологии cyclohexene cyclohexane cyclohexyl hydroperoxide cyclohexanone cyclohexanol liquid phase oxidation epoxidation |
| title | Epoxidation of cyclohexene with cyclohexyl hydroperoxide |
| title_full | Epoxidation of cyclohexene with cyclohexyl hydroperoxide |
| title_fullStr | Epoxidation of cyclohexene with cyclohexyl hydroperoxide |
| title_full_unstemmed | Epoxidation of cyclohexene with cyclohexyl hydroperoxide |
| title_short | Epoxidation of cyclohexene with cyclohexyl hydroperoxide |
| title_sort | epoxidation of cyclohexene with cyclohexyl hydroperoxide |
| topic | cyclohexene cyclohexane cyclohexyl hydroperoxide cyclohexanone cyclohexanol liquid phase oxidation epoxidation |
| url | https://www.finechem-mirea.ru/jour/article/view/2010 |
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