Synthesis of 9-fluorenone by the micro-nanobubble-enhanced ozone oxidation of fluorene

IF 2.2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of the Iranian Chemical Society Pub Date : 2024-09-26 DOI:10.1007/s13738-024-03104-9
Wenqiang Gao, Na Wu, Zhiyu Wang, Yongqi Qin
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Abstract

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.

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通过微纳米气泡增强臭氧氧化芴合成 9-芴酮
本文提出了一种通过臭氧氧化和使用微纳米气泡技术从芴制备 9-芴酮的更环保、更高效的方法。首先研究了臭氧微纳米气泡在不同极性有机溶剂中的传质效果。与乙酸乙酯、丙酮、二氯甲烷、氯仿和 1,2-二氯乙烷等溶剂相比,臭氧在酒精溶剂中的平衡浓度更高,而在乙酸乙酯、丙酮、二氯甲烷、氯仿和 1,2-二氯乙烷中,臭氧的平衡浓度相近。臭氧与溶剂分子之间氢键或偶极-偶极相互作用的变化导致了溶解度的变化。以乙酸乙酯为理想溶剂,臭氧与芴的摩尔比为 1.6:1,反应时间为 90 分钟,臭氧氧化的最佳条件是 9-芴酮的收率达到 66%。我们还推测了臭氧氧化氟的化学机制。电子顺磁共振光谱证实了反应过程中羟自由基的存在。在特定反应中,臭氧的间接氧化作用占主导地位。这种方法不需要催化剂,而且简便易行,非常适合大规模生产 9-芴酮。
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来源期刊
CiteScore
4.40
自引率
8.30%
发文量
230
审稿时长
5.6 months
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.
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