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

Research Project

Project/Area Number 04555202
Research Category

Grant-in-Aid for Developmental Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionTokyo Institute of Technology

Principal Investigator

FUCHIGAMI Toshio  Tokyo Institute of Technology, Interdisciplinary Graduate School of Science and Engineering Associate Professor, 大学院総合理工学研究科, 助教授 (10016701)

Co-Investigator(Kenkyū-buntansha) KONNO Akinori  Tokyo Institute of Technology, Interdisciplinary Graduate School of Science and, 大学院総合理工学研究科, 助手 (50205572)
Project Period (FY) 1992 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1993: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1992: ¥2,500,000 (Direct Cost: ¥2,500,000)
KeywordsFunctional fluorine compound / Anodic partial fluorination / Electrode process / Flow cell / Anodic oxidation
Research Abstract

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.

Report

(3 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] 吉山寅仙: "Anodic gem-Difluorination of Dithioacetals" Chemistry Letters. 1995-1998 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] 淵上寿雄: "Regioselective Anodic Monofluorination of Organoselenium Compounds and Synthetic Application" Tetrahedron Letters. 33. 3161-3164 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] 昆野昭則: "Highly Regioselective Electrochemical Monofluorination of Aliphatic Nitrogen-Containing Heterocycles" Tetrahedron Letters. 33. 7017-7020 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] 淵上寿雄: "Selective Flnodic Partial Fluorination of Heteroatom Compounds" Reviews on Heteroatom Chemistry. 10(印刷中). (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] 淵上寿雄: "Selective Anodic Partial Fluorination of Organic Molecules in “Current Topics in Electrochemistry"" Research Trends(India), 13 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Yoshiyama: "Anodic gem-Difluorination of Dithioacetals" Chemistry Letters. 1995-1998 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Fuchigami: "Regioselective Anodic Monofluorination of Organoselenium Compounds and Their Synthetic Application" Tetrahedron Letters. 33. 3161-3164 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] A.Konno: "Highly Regioselective Electrochemical Monofluorination of Aliphatic Nitrogen-Containing Heterocycles" Tetrahedron Letters. 33. 7017-7020 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Fuchigami: "Selective Anodic Partial Fluorination of Heteroatom Compounds" Revies on Heteroatom Chemistry. 10, (in press). (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Fuchigami: "Selective Anodic Partial Fluorination of Organic Molecules in "Current Topics in Electrochemistry"" Research Trends (India). (in press). (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] 淵上寿雄: "Selective Anodic Partial Fluorination of Heteroatom Compounds" Reviews on Heteroatom Chemistry. 10(印刷中). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] 淵上寿雄: "“Selective Anodic Partial Fluorination of Organic Molecules" in “Current Topics in Electrochemistry"" Research Trends,India, 13 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] 吉山 寅仙: "Anodic gem-Difluoriration of Dithioacetals" Chemistry Letters. 1995-1998 (1992)

    • Related Report
      1992 Annual Research Report

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Published: 1992-04-01   Modified: 2016-04-21  

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