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Photocatalytic formylation of amine with carbon dioxide

Research Project

Project/Area Number 16K14477
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Catalyst/Resource chemical process
Research InstitutionKyoto University

Principal Investigator

Yoshida Hisao  京都大学, 人間・環境学研究科, 教授 (80273267)

Co-Investigator(Kenkyū-buntansha) 吉田 朋子  大阪市立大学, 複合先端研究機構, 教授 (90283415)
Co-Investigator(Renkei-kenkyūsha) YAMAMOTO Akira  京都大学, 人間・環境学研究科, 助教 (30769443)
Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords光触媒反応 / 二酸化炭素 / アミン / 光触媒 / 触媒・化学プロセス
Outline of Final Research Achievements

To utilize carbon dioxide, we examined photocatalytic formylation of amine with carbon dioxide. Metal-loaded titanium oxide photocatalyst was found to give the aimed product from carbon dioxide and some amine compounds in acetonitrile. The reaction took place only in the acetonitrile solvent. A kinetics study revealed that the C-H bond activation of acetonitrile was an important step in the reaction mechanism. Although the product was obtained without carbon dioxide in the gas phase, the amount of the product was higher in the atmosphere of gaseous carbon dioxide. Based on these results, the following reaction mechanism was proposed: the radical species, formed from acetonitrile, reacts with the carbon dioxide, which interacts with amine, to provide the aimed product.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (34 results)

All 2018 2017 2016

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Acknowledgement Compliant: 1 results) Presentation (29 results) (of which Int'l Joint Research: 13 results,  Invited: 5 results)

  • [Journal Article] Direct cross-coupling between alkenes and tetrahydrofuran with a platinum-loaded titanium oxide photocatalyst2018

    • Author(s)
      Tyagi Akanksha、Yamamoto Akira、Yamamoto Muneaki、Yoshida Tomoko、Yoshida Hisao
    • Journal Title

      Catalysis Science & Technology

      Volume: 印刷中 Issue: 10 Pages: 2546-2556

    • DOI

      10.1039/c8cy00129d

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Visible-light-induced photocatalytic benzene/cyclohexane cross-coupling utilizing a ligand-to-metal charge transfer benzene complex adsorbed on titanium oxides2018

    • Author(s)
      Yamamoto A.、Ohara T.、Yoshida H.
    • Journal Title

      Catalysis Science & Technology

      Volume: 8 Issue: 8 Pages: 2046-2050

    • DOI

      10.1039/c7cy02566a

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dehydrogenative lactonization of diols with a platinum-loaded titanium oxide photocatalyst2017

    • Author(s)
      Wada Emiko、Tyagi Akanksha、Yamamoto Akira、Yoshida Hisao
    • Journal Title

      Photochemical & Photobiological Sciences

      Volume: 16 Issue: 12 Pages: 1744-1748

    • DOI

      10.1039/c7pp00258k

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bifunctional property of Pt nanoparticles deposited on TiO2 for the photocatalytic sp3C?sp3C cross-coupling reactions between THF and alkanes2017

    • Author(s)
      Tyagi Akanksha、Yamamoto Akira、Kato Tatsuhisa、Yoshida Hisao
    • Journal Title

      Catalysis Science & Technology

      Volume: 7 Issue: 12 Pages: 2616-2623

    • DOI

      10.1039/c7cy00535k

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct cyanomethylation of aliphatic and aromatic hydrocarbons with acetonitrile over metal loaded titanium oxide photocatalyst2017

    • Author(s)
      Emiko Wada, Tomoaki Takeuchi, Yuki Fujimura, Akanksha Tyagi, Tatsuhisa Kato, and Hisao Yoshida
    • Journal Title

      Catalysis Science & Technology

      Volume: - Issue: 12 Pages: 2457-2466

    • DOI

      10.1039/c7cy00365j

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] ピリジン酸化チタン表面錯合体による光励起クロスカップリング2018

    • Author(s)
      浪花 晋平,山本 旭,吉田 寿雄
    • Organizer
      第121回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] フラックス法により調製したチタン酸カルシウム光触媒の構造と二酸化炭素の光還元活性2018

    • Author(s)
      安齋 亮彦,山本 旭,吉田 寿雄
    • Organizer
      第121回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Optimization of silver-loaded sodium titanate photocatalyst for the reduction of carbon dioxide with water2018

    • Author(s)
      Zhu Xing, Akira Yamamoto, Hisao Yoshida
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] カチオンドープチタン酸カルシウム光触媒による二酸化炭素還元反応2018

    • Author(s)
      清弘 泰三,安齋 亮彦,山本 旭,吉田 寿雄
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Selective cross-coupling of heteroaromatic compounds over titanium oxide photocatalyst2017

    • Author(s)
      Shimpei Naniwa, Akira Yamamoto, Hisao Yoshida
    • Organizer
      Photocatalysis 2 & SIEMME’23
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Study of structure and activity of calcium titanate for photocatalytic reduction of CO22017

    • Author(s)
      Akihiko Anzai, Akira Yamamoto, Hisao Yoshida
    • Organizer
      Photocatalysis 2 & SIEMME’23
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 酸化チタン表面錯合体光励起による芳香族化合物の選択的直接クロスカップリング2017

    • Author(s)
      浪花 晋平,山本 旭,吉田 寿雄
    • Organizer
      第36回 固体・表面光化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Room temperature Ullman coupling of aryl halides by metal loaded TiO2 photocatalysis2017

    • Author(s)
      Akanksha Tyagi, Akira Yamamoto, Hisao Yoshida
    • Organizer
      第36回 固体・表面光化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] フラックス法により調製したチタン酸カルシウム光触媒の構造と二酸化炭素の光還元活性2017

    • Author(s)
      安齋 亮彦,山本 旭,吉田 寿雄
    • Organizer
      第36回 固体・表面光化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Photocatalytic conversion of CO2 by water over Ag-modified Na2Ti6O132017

    • Author(s)
      Xing Zhu, Akira Yamamoto, Hisao Yoshida
    • Organizer
      第36回 固体・表面光化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Photocatalytic Reduction of Carbon Dioxide with Silver Loaded Titanate Photocatalysts2017

    • Author(s)
      Hisao Yoshida
    • Organizer
      OKCAT2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Efficient room temperature photocatalytic Ullmann coupling of aryl halides2017

    • Author(s)
      Akanksha Tyagi, Akira Yamamoto, Hisao Yoshida
    • Organizer
      第10回触媒表面化学研究発表会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Photoreduction of carbon dioxide with water over Ag-modified Na2Ti6O132017

    • Author(s)
      Xing Zhu, Akira Yamamoto, Hisao Yoshida
    • Organizer
      第10回触媒表面化学研究発表会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Photocatalysis in various chemical reactions2017

    • Author(s)
      Hisao Yoshida
    • Organizer
      International Conference of the Indonesian Chemical Society 2017 (ICICS2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Photocatalytic organic synthesis with titanium oxide photocatalyst2017

    • Author(s)
      Hisao Yoshida
    • Organizer
      Guest Lecture Series in Material Chemistry for Energy Health and Environment
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 二酸化炭素光還元 反応におけるチタン酸カルシウム光触媒の構造と活性2017

    • Author(s)
      安齋 亮彦,山本 旭,吉田 寿雄
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 酸化チタン光触媒を用いた含窒素芳香族化合物の選択的直接クロスカップリング2017

    • Author(s)
      浪花 晋平,山本 旭,吉田 寿雄
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Photocatalytic cyanomethylation of hydrocarbons with acetonitrile over metal loaded titanium oxide2017

    • Author(s)
      H. Yoshida, E. Wada, T. Takeuchi, Y. Fujimura, T. Kato
    • Organizer
      EUROPACAT2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Highly selective photocatalytic reduction of carbon dioxide with water over silver-modified calcium titanate2017

    • Author(s)
      Akihiko Anzai, Naoto Fukuo, Akira Yamamoto, Hisao Yoshida
    • Organizer
      EUROPACAT2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Pt/TiO2 hybrid catalysts for the sp3C-sp3C cross-coupling reaction between cyclohexane and tetrahydrofuran2017

    • Author(s)
      Akanksha Tyagi, Akira Yamamoto, Hisao Yoshida
    • Organizer
      EUROPACAT2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Direct cross-coupling between cyclohexane and pyridine over metal loaded titanium oxide photocatalyst2017

    • Author(s)
      Shimpei Naniwa, Tomoyuki Ohara, Akira Yamamoto, Hisao Yoshida
    • Organizer
      EUROPACAT2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 光触媒を用いた有機化学反応の開発とその反応機構2017

    • Author(s)
      吉田寿雄
    • Organizer
      第36回 光がかかわる触媒化学シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] フラックス法によって調製したチタン酸カルシウムの構造と二酸化炭素光還元活性2017

    • Author(s)
      安齊亮彦,山本旭,吉田寿雄
    • Organizer
      第36回 光がかかわる触媒化学シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 酸化チタン光触媒を用いた含窒素芳香族化合物の選択的クロスカップリング2017

    • Author(s)
      浪花晋平,山本旭,吉田寿雄
    • Organizer
      第36回 光がかかわる触媒化学シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 光触媒によるあたらしい有機化学反応2017

    • Author(s)
      吉田寿雄
    • Organizer
      第8回触媒科学研究発表会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Sodium hexatitanate photocatalysts prepared by a flux method for CO2 reduction with water2017

    • Author(s)
      H. Yoshida, M. Sato, N. Fukuo, L. Zhang, Y. Yamamoto, T. Yoshida, T. Morikawa, T. Kajino, M. Sakano, T. Sekito, S. Matsumoto, H. Hirata
    • Organizer
      16th Korea-Japan Symposium on Catalysis & 3rd International Symposium of Institute for Catalysis
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Fixation of carbon dioxide by amines with titanium oxide photocatalyst2016

    • Author(s)
      Akanksha Tyagi, Akira Yamamoto, Hisao Yoshida
    • Organizer
      The 16th International Congress on Catalysis (ICC16)
    • Place of Presentation
      Beijing, China
    • Year and Date
      2016-07-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] CO2 functionalization by amines over titania photocatalysts2016

    • Author(s)
      Akanksha Tyagi, Akira Yamamoto, Hisao Yoshida
    • Organizer
      International Symposium on Nanostructured Photocatalysts and Catalysts (NPC2016)
    • Place of Presentation
      Osaka, Japan
    • Year and Date
      2016-04-09
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Carbon dioxide fixation by titanium oxide photocatalysts2016

    • Author(s)
      Akanksha Tyagi, Akira Yamamoto, Hisao Yoshida
    • Organizer
      26th IUPAC International Symposium on Photochemistry
    • Place of Presentation
      Osaka, Japan
    • Year and Date
      2016-04-04
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research

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Published: 2016-04-21   Modified: 2019-03-29  

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