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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.

有机氟化合物对于开发新型药物、农用化学品和功能材料非常有用。然而，迄今为止，其开发所需的部分氟化方法尚未开发出来。从这些角度出发，我们对最近发现的杂原子化合物的阳极部分氟化的工业化进行了基础研究。首先，利用普通的批量电池对有机硫和硒化合物的阳极部分氟化进行了优化。接下来，我们设计和改进了市售的小型实验室规模流通池系统，作为工业化的初步方法。然后，使用我们设计的压滤式流通池对作为模型化合物的α-苯硫基乙酸酯的阳极单氟化进行了详细研究。发现即使在流通池中也能实现选择性氟化。研究还发现，流量对阳极氟化的产率和电流效率影响较小，而电流密度对其影响较大。结果表明，除了铂之外，石墨片和DSA（尺寸稳定阳极）都可以用作氟化的阳极。从实用的角度来看，这一发现应该很重要。此外，我们已经利用该流程系统成功地进行了杂环化合物的阳极部分氟化。因此，我们证明了我们开发的流程系统可以广泛应用，并且应该是制造各种类型有机氟化合物的通用工艺。