One-pot Baeyer–Villiger oxidation of cyclohexanone with in situ generated hydrogen peroxide over Sn-Beta zeolites
ε-Caprolactone is traditionally produced through Baeyer-Villiger oxidation of cyclohexanone oxidized by peracids in industry, which inevitably results in large discard acid and environmental pollution. To this end, a green route to ε-caprolactone was developed by coupling the direct generation of hy...
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| Format: | Article |
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KeAi Communications Co. Ltd.
2021-09-01
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| Series: | Green Chemical Engineering |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666952821000261 |
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| author | Jianwei Luo Haoran Yuan Hui Liu Jingbo Li Yu Wang Yong Wang Jia Yao Haoran Li |
| author_facet | Jianwei Luo Haoran Yuan Hui Liu Jingbo Li Yu Wang Yong Wang Jia Yao Haoran Li |
| author_sort | Jianwei Luo |
| collection | DOAJ |
| description | ε-Caprolactone is traditionally produced through Baeyer-Villiger oxidation of cyclohexanone oxidized by peracids in industry, which inevitably results in large discard acid and environmental pollution. To this end, a green route to ε-caprolactone was developed by coupling the direct generation of hydrogen peroxide from aerobic oxidation of benzhydrol catalyzed by NHPI and Baeyer-Villiger oxidation of cyclohexanone with the in situ hydrogen peroxide over Sn-Beta zeolites in one pot. Molecular oxygen was employed as the terminal oxidant, and the effects of several reaction factors were studied. Compared with one-step process, the one-pot two-step method noticeably improved the selectivity of ε-caprolactone. When the amount of in situ hydrogen peroxide was 0.72 equivalent, the selectivity of ε-caprolactone was obtained 94.8% with 39.2% conversion of cyclohexanone, and the efficiency of H2O2 was up to 51.5%. As compared to the commercial 30 wt% aqueous H2O2 added directly, in situ H2O2 dramatically improved the selectivity of ε-caprolactone and had higher efficiency. Additionally, the catalyst could be easily separated from the reaction solution and reused several times without the remarkable loss of activity. |
| first_indexed | 2024-04-11T04:50:30Z |
| format | Article |
| id | doaj.art-e3689910e17a4a5bbc9da6df984fc0b3 |
| institution | Directory Open Access Journal |
| issn | 2666-9528 |
| language | English |
| last_indexed | 2024-04-11T04:50:30Z |
| publishDate | 2021-09-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Chemical Engineering |
| spelling | doaj.art-e3689910e17a4a5bbc9da6df984fc0b32022-12-27T04:39:50ZengKeAi Communications Co. Ltd.Green Chemical Engineering2666-95282021-09-0123294300One-pot Baeyer–Villiger oxidation of cyclohexanone with in situ generated hydrogen peroxide over Sn-Beta zeolitesJianwei Luo0Haoran Yuan1Hui Liu2Jingbo Li3Yu Wang4Yong Wang5Jia Yao6Haoran Li7Department of Chemistry, ZJU-NHU United R&D Center, Zhejiang University, Hangzhou, 310027, ChinaDepartment of Chemistry, ZJU-NHU United R&D Center, Zhejiang University, Hangzhou, 310027, ChinaZhejiang NHU Company Ltd., Xinchang, 312500, ChinaZhejiang NHU Company Ltd., Xinchang, 312500, ChinaZhejiang NHU Company Ltd., Xinchang, 312500, ChinaState Key Laboratory of Chemical Engineering, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027, ChinaDepartment of Chemistry, ZJU-NHU United R&D Center, Zhejiang University, Hangzhou, 310027, ChinaDepartment of Chemistry, ZJU-NHU United R&D Center, Zhejiang University, Hangzhou, 310027, China; State Key Laboratory of Chemical Engineering, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027, China; Corresponding author.ε-Caprolactone is traditionally produced through Baeyer-Villiger oxidation of cyclohexanone oxidized by peracids in industry, which inevitably results in large discard acid and environmental pollution. To this end, a green route to ε-caprolactone was developed by coupling the direct generation of hydrogen peroxide from aerobic oxidation of benzhydrol catalyzed by NHPI and Baeyer-Villiger oxidation of cyclohexanone with the in situ hydrogen peroxide over Sn-Beta zeolites in one pot. Molecular oxygen was employed as the terminal oxidant, and the effects of several reaction factors were studied. Compared with one-step process, the one-pot two-step method noticeably improved the selectivity of ε-caprolactone. When the amount of in situ hydrogen peroxide was 0.72 equivalent, the selectivity of ε-caprolactone was obtained 94.8% with 39.2% conversion of cyclohexanone, and the efficiency of H2O2 was up to 51.5%. As compared to the commercial 30 wt% aqueous H2O2 added directly, in situ H2O2 dramatically improved the selectivity of ε-caprolactone and had higher efficiency. Additionally, the catalyst could be easily separated from the reaction solution and reused several times without the remarkable loss of activity.http://www.sciencedirect.com/science/article/pii/S2666952821000261Baeyer-Villiger oxidationε-CaprolactoneSn-BetaHydrogen peroxideMolecular oxygen |
| spellingShingle | Jianwei Luo Haoran Yuan Hui Liu Jingbo Li Yu Wang Yong Wang Jia Yao Haoran Li One-pot Baeyer–Villiger oxidation of cyclohexanone with in situ generated hydrogen peroxide over Sn-Beta zeolites Green Chemical Engineering Baeyer-Villiger oxidation ε-Caprolactone Sn-Beta Hydrogen peroxide Molecular oxygen |
| title | One-pot Baeyer–Villiger oxidation of cyclohexanone with in situ generated hydrogen peroxide over Sn-Beta zeolites |
| title_full | One-pot Baeyer–Villiger oxidation of cyclohexanone with in situ generated hydrogen peroxide over Sn-Beta zeolites |
| title_fullStr | One-pot Baeyer–Villiger oxidation of cyclohexanone with in situ generated hydrogen peroxide over Sn-Beta zeolites |
| title_full_unstemmed | One-pot Baeyer–Villiger oxidation of cyclohexanone with in situ generated hydrogen peroxide over Sn-Beta zeolites |
| title_short | One-pot Baeyer–Villiger oxidation of cyclohexanone with in situ generated hydrogen peroxide over Sn-Beta zeolites |
| title_sort | one pot baeyer villiger oxidation of cyclohexanone with in situ generated hydrogen peroxide over sn beta zeolites |
| topic | Baeyer-Villiger oxidation ε-Caprolactone Sn-Beta Hydrogen peroxide Molecular oxygen |
| url | http://www.sciencedirect.com/science/article/pii/S2666952821000261 |
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