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

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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.