{"title":"通过微纳米气泡增强臭氧氧化芴合成 9-芴酮","authors":"Wenqiang Gao, Na Wu, Zhiyu Wang, Yongqi Qin","doi":"10.1007/s13738-024-03104-9","DOIUrl":null,"url":null,"abstract":"<div><p>This article proposes a greener and more efficient method for preparing 9-fluorenone from fluorene via ozone oxidation and the use of micro-nanobubble technology. The effectiveness of ozone micro-nanobubble mass transfer in different polar organic solvents was first studied. Equilibrium concentrations of ozone were higher in alcoholic solvents than in solvents such as ethyl acetate, acetone, dichloromethane, chloroform, and 1,2-dichloroethane, which showed similar equilibrium concentrations of ozone. The variation in hydrogen bonding or dipole–dipole interactions between ozone and solvent molecules caused this change in solubility. Using ethyl acetate as the ideal solvent, with an ozone: fluorene molar ratio of 1.6:1 and reaction duration of 90 min, optimal conditions for ozone oxidation resulted in a 66% yield of 9-fluorenone. We also postulated the chemical mechanism involved in fluorine oxidation by ozone. The presence of hydroxyl radicals during the reaction was confirmed via electron paramagnetic resonance spectra. Indirect ozone oxidation predominated in particular reactions. No requirement of a catalyst and ease of this method makes it well suited for the large-scale manufacturing of 9-fluorenone.</p></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":null,"pages":null},"PeriodicalIF":2.2000,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of 9-fluorenone by the micro-nanobubble-enhanced ozone oxidation of fluorene\",\"authors\":\"Wenqiang Gao, Na Wu, Zhiyu Wang, Yongqi Qin\",\"doi\":\"10.1007/s13738-024-03104-9\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>This article proposes a greener and more efficient method for preparing 9-fluorenone from fluorene via ozone oxidation and the use of micro-nanobubble technology. The effectiveness of ozone micro-nanobubble mass transfer in different polar organic solvents was first studied. Equilibrium concentrations of ozone were higher in alcoholic solvents than in solvents such as ethyl acetate, acetone, dichloromethane, chloroform, and 1,2-dichloroethane, which showed similar equilibrium concentrations of ozone. The variation in hydrogen bonding or dipole–dipole interactions between ozone and solvent molecules caused this change in solubility. Using ethyl acetate as the ideal solvent, with an ozone: fluorene molar ratio of 1.6:1 and reaction duration of 90 min, optimal conditions for ozone oxidation resulted in a 66% yield of 9-fluorenone. We also postulated the chemical mechanism involved in fluorine oxidation by ozone. The presence of hydroxyl radicals during the reaction was confirmed via electron paramagnetic resonance spectra. Indirect ozone oxidation predominated in particular reactions. No requirement of a catalyst and ease of this method makes it well suited for the large-scale manufacturing of 9-fluorenone.</p></div>\",\"PeriodicalId\":676,\"journal\":{\"name\":\"Journal of the Iranian Chemical Society\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.2000,\"publicationDate\":\"2024-09-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of the Iranian Chemical Society\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s13738-024-03104-9\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the Iranian Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s13738-024-03104-9","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Synthesis of 9-fluorenone by the micro-nanobubble-enhanced ozone oxidation of fluorene
This article proposes a greener and more efficient method for preparing 9-fluorenone from fluorene via ozone oxidation and the use of micro-nanobubble technology. The effectiveness of ozone micro-nanobubble mass transfer in different polar organic solvents was first studied. Equilibrium concentrations of ozone were higher in alcoholic solvents than in solvents such as ethyl acetate, acetone, dichloromethane, chloroform, and 1,2-dichloroethane, which showed similar equilibrium concentrations of ozone. The variation in hydrogen bonding or dipole–dipole interactions between ozone and solvent molecules caused this change in solubility. Using ethyl acetate as the ideal solvent, with an ozone: fluorene molar ratio of 1.6:1 and reaction duration of 90 min, optimal conditions for ozone oxidation resulted in a 66% yield of 9-fluorenone. We also postulated the chemical mechanism involved in fluorine oxidation by ozone. The presence of hydroxyl radicals during the reaction was confirmed via electron paramagnetic resonance spectra. Indirect ozone oxidation predominated in particular reactions. No requirement of a catalyst and ease of this method makes it well suited for the large-scale manufacturing of 9-fluorenone.
期刊介绍:
JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.