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Development of Selective Electrolytic Partial Fluorination Processes for Manufacturing Functional Organic Fluorine Compounds

开发用于制造功能性有机氟化合物的选择性电解部分氟化工艺

基本信息

批准号：
04555202
负责人：
FUCHIGAMI Toshio
金额：
$ 2.24万
依托单位：
Tokyo Institute of Technology
依托单位国家：
日本
项目类别：
Grant-in-Aid for Developmental Scientific Research (B)
财政年份：
1992
资助国家：
日本
起止时间：
1992 至 1993
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-04555202/
关键词：
Functional fluorine compound Anodic partial fluorination Electrode process Flow cell Anodic oxidation

项目摘要

Organic fluorine compounds are highly useful for developing new type of medicines, agricultural chemicals, and functional materials. However, methods of partial fluorination neccessary for their development have been underdeveloped so far. From these viewpoints, we have done fundamental study to industrialize the anodic partial fluorination of heteroatom compounds, which we have found recently.First, anodic partial fluorination of organic sulfur and selenium compounds has been optimized by using an ordinary batch cell.Next, we have designed and modified commercially available small laboratory-scale flow cell system as a preliminary approach to industriallization. And then, the anodic monofluorination of alpha-phenylsulfenylacetic acid ester as a model compound has been investigated in detail by using our designed filter press type flow cell. It was found that selective fluorination was achieved even in the flow cell. It was also found that the flow rate affected slightly the yield and current efficiency of the anodic fluorination while the current density affected them considerably. It was shown that both graphite sheet and DSA (dimensionally stable anode) other than platinum can be used as an anode for the fluorination. This finding should be important from a practical viewpoint.Furtheremore, we have successfully carried out the anodic partial fluorination of heterocyclic compounds by using this flow system.Thus, we have demonstrated that our developed flow system can be widely applicable and should be a versatile process for manufacturing various types of organic fluorine compounds.

有机氟化合物在开发新型药物、农药和功能材料方面具有重要的应用价值。然而，到目前为止，为它们的发展提供部分必要条件的方法还不发达。从这些观点出发，我们对最近发现的杂原子化合物的阳极部分氧化进行了工业化的基础性研究：首先，使用普通的间歇式电解槽对有机硫和硒化合物的阳极部分氧化进行了优化;其次，我们设计并改进了商业上可获得的小型实验室规模的流动电解槽系统，作为工业化的初步途径。然后，以α-苯硫基乙酸酯为模型化合物，采用自行设计的压滤式流动池，对该体系的阳极氧化进行了详细的研究。发现即使在流动池中也实现了选择性的氧化。流速对阳极氧化的产率和电流效率影响不大，而电流密度对产率和电流效率影响较大。结果表明，除了铂之外，石墨片和DSA（尺寸稳定阳极）都可以用作阳极。这一发现从实用的观点来看是重要的。此外，我们已经成功地进行了使用该流动系统的杂环化合物的阳极部分氧化。因此，我们已经证明，我们开发的流动系统可以广泛适用，应该是一个通用的方法，用于生产各种类型的有机氟化合物。