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Development of a novel solid catalyst with transition metal complex for selective hydroxylation

Research Project

Project/Area Number 16K06855
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Catalyst/Resource chemical process
Research InstitutionEhime University

Principal Investigator

Yamaguchi Syuhei  愛媛大学, 理工学研究科(工学系), 准教授 (50397494)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2017: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsフェノール合成 / ベンゼン酸化 / 固体触媒 / 金属酸化触媒 / ゼオライト / 一段階合成 / 過酸化水素 / 活性中間体捕捉 / 選択酸化反応 / 遷移金属錯体 / 選択的水酸化反応 / カチオン交換 / 触媒・化学プロセス
Outline of Final Research Achievements

Phenols are various organic intermediates. Most of the phenols are produced industrially in a multistage process. For example, the cumene method, which is widely used as a commercial method for producing phenol, requires a three-step process. On the other hand, the direct hydroxylation of benzene to phenol with environmentally friendly oxidants has attracted much attention.
We tried to develop an efficient benzene oxidation catalyst to improve iron complexes encapsulated into zeolite. By optimizing the iron complex moiety as a catalytic active site and the cation moiety as the product capture site,improving the benzene oxidation activity was succeeded. Furthermore, developing a catalyst with higher activity by immobilizing the iron complex using a cation exchange resin as a carrier was also succeeded.

Academic Significance and Societal Importance of the Research Achievements

我々は、ゼオライト空孔内に遷移金属錯体を触媒活性部位として導入し、さらにゼオライトに存在するカチオン部分を生成物捕捉部位として、有機基質の選択水酸化反応を進行させることに成功した。触媒活性部位とカチオン部位の組合せを考慮して触媒を調製することでフェノールの一段階での水酸化反応が実現できると考えている。フェノール樹脂など非常に用途の広いフェノールが一段階の反応プロセスで合成ができれば、従来の多段階の反応プロセスで用いられていた試薬、溶媒、エネルギーなどの大幅な低減が期待でき、環境・エネルギー問題に大きく貢献できると考えられる。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (32 results)

All 2019 2018 2017 2016 Other

All Journal Article (9 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 9 results,  Acknowledgement Compliant: 2 results) Presentation (21 results) (of which Int'l Joint Research: 6 results,  Invited: 2 results) Remarks (2 results)

  • [Journal Article] Catalytic oxidation of benzene to phenol with hydrogen peroxide over Feterpyridine complexes supported on a cation exchange resin2018

    • Author(s)
      Syuhei Yamaguchi, Kohei Miyamoto, Hidenori Yahiro
    • Journal Title

      Catalysis Communications

      Volume: 116 Pages: 48-51

    • DOI

      10.1016/j.catcom.2018.08.011

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Oxidation of cyclic hydrocarbons with hydrogen peroxide over iron complexes encapsulated in cation-exchanged zeolite2018

    • Author(s)
      Yamaguchi Syuhei、Miyake Yuki、Takiguchi Keiko、Ihara Daijiro、Yahiro Hidenori
    • Journal Title

      Catalysis Today

      Volume: 303 Pages: 249-255

    • DOI

      10.1016/j.cattod.2017.10.047

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Selective Oxidation of Thioanisole with Hydrogen Peroxide using Copper Complexes Encapsulated in Zeolite: Formation of a Thermally Stable and Reactive Copper Hydroperoxo Species2018

    • Author(s)
      Syuhei Yamaguchi, Akinori Suzuki, Makoto Togawa, Maiko Nishibori, Hidenori Yahiro
    • Journal Title

      ACS Catalysis

      Volume: 8 Issue: 4 Pages: 2645-2650

    • DOI

      10.1021/acscatal.7b04092

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Self-propagating high-temperature synthesis of highly dispersed noble metals on ceria powder: Application to Pd/CeO 2 catalyst2017

    • Author(s)
      Daniel Sanchez-Rodriguez, Syuhei Yamaguchi, Daijiro Ihara, Hiroyuki Yamaura, Hidenori Yahiro
    • Journal Title

      Ceramics International

      Volume: 43 Issue: 16 Pages: 14533-14536

    • DOI

      10.1016/j.ceramint.2017.07.208

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of LaFeO3 perovskite-type oxide via solid-state combustion of a cyano complex precursor: The effect of oxygen diffusion2017

    • Author(s)
      Daniel Sanchez-Rodriguez, Hiroki Wada, Syuhei Yamaguchi, Jordi Farjas, Hidenori Yahiro
    • Journal Title

      Ceramics International

      Volume: 43 Issue: 3 Pages: 3156-3165

    • DOI

      10.1016/j.ceramint.2016.11.134

    • Related Report
      2017 Research-status Report 2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Investigation on Reduction Behaviors of SnO2 and SnO2-Supported CuO Sensor Materials by Temperature-Programmed Reduction Method Combined with Resistance Measurement2016

    • Author(s)
      Hiroyuki Yamaura, Shinsuke Hirao, Syuhei Yamaguchi, Hidenori Yahiro
    • Journal Title

      Sensors and Materials

      Volume: 28 Pages: 1203-1210

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cyanosilylation of Benzaldehyde with Trimethylsilyl cyanide over Zn-Sn Mixed Oxide Catalysts with Cubic-shaped Particles2016

    • Author(s)
      Syuhei Yamaguchi, Hiroyuki Yamaura, Kenta Morihara, Masataka Iwasaki, Hidenori Yahiro
    • Journal Title

      Chemistry Letters

      Volume: 45 Issue: 8 Pages: 851-853

    • DOI

      10.1246/cl.160320

    • NAID

      130005254584

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regioselective and Stereospecific Dehydrogenative Annulation Utilizing Silylium Ion-Activated Alkenes2016

    • Author(s)
      H. Arii, Y. Yano, K. Nakabayashi, S. Yamaguchi, M. Yamamura, K. Mochida, T. Kawashima
    • Journal Title

      J. Org. Chem.

      Volume: 81 Issue: 15 Pages: 6314-6319

    • DOI

      10.1021/acs.joc.6b00793

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Cyanosilylation of benzaldehyde with TMSCN over A-site metal substituted perovskite-type oxide catalyst prepared by thermal decomposition of heteronuclear cyano complex precursors2016

    • Author(s)
      Syuhei Yamaguchi, Hiroki Wada, Takahisa Okuwa, Hidenori Yahiro
    • Journal Title

      Ceramics Transactions

      Volume: 257 Pages: 81-90

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Presentation] 鉄錯体内包ゼオライト触媒を用いた環状炭化水素類の部分酸化反応2019

    • Author(s)
      山口修平,宮本晃平,三宅祐輝,瀧口慶子,八尋秀典
    • Organizer
      平成30年度 高難度選択酸化反応研究会シンポジウム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 鉄・亜鉛錯体含有層状化合物触媒を用いたベンゼン酸化反応2019

    • Author(s)
      山下祐輝,山口修平,八尋秀典
    • Organizer
      第123回触媒討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Oxidation of Thioanisole with Hydrogen Peroxide over Copper(II)-Terpy Complexes Encapsulated into Supercages of Zeolite2018

    • Author(s)
      Syuhei Yamaguchi
    • Organizer
      International Symposium on Advancement and Prospect of Catalysis Science & Technology
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Oxidation of Thioanisole with Hydrogen Peroxide over Copper(II)-Terpy Complexes Encapsulated in Zeolite2018

    • Author(s)
      Syuhei Yamaguchi
    • Organizer
      the 43rd International Conference on Coordination Chemistry (ICCC2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Catalytic Activity of Cu(II)-Terpy Complexes Encapsulated in Cation-exchanged Zeolites for Oxidation of Thioanisole with Hydrogen Peroxide2018

    • Author(s)
      Syuhei Yamaguchi, Syuya Kajimoto, Koichi Tanabe, Hidenori Yahiro
    • Organizer
      International Symposium on Zeolites and Microporous Crystals (ZMPC) 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 銅錯体内包ゼオライト触媒を用いた酸化反応に銅イオン交換量が与える影響2018

    • Author(s)
      山口修平,鈴木彰規,田邊晃一,八尋秀典
    • Organizer
      第51回酸化反応討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 鉄-ターピリジン錯体含有イオン交換樹脂触媒を用いたベンゼン酸化反応2018

    • Author(s)
      山口修平, 宮本晃平, 八尋秀典
    • Organizer
      第122回触媒討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 種々の銅錯体を内包したゼオライト触媒を用いたベンゼン類の酸化反応2018

    • Author(s)
      十川誠,山口修平,八尋秀典
    • Organizer
      2018年日本化学会中国四国支部大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 鉄-ターピリジン錯体および亜鉛-ビピリジン錯体を固定化した触媒を用いたベンゼン酸化反応2018

    • Author(s)
      山下祐輝,山口修平,八尋秀典
    • Organizer
      2018年日本化学会中国四国支部大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 種々の遷移金属錯体をモンモリロナイトに固定化した触媒の調製とキャラクタリゼーション2018

    • Author(s)
      山下祐輝,伊原大二朗,井場堅斗,山口修平,八尋秀典
    • Organizer
      第121回触媒討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Oxidation of Benzene with Hydrogen Peroxide over Iron-Bipyridine Complexes Encapsulated in Metal Cation-Exchanged Zeolite2017

    • Author(s)
      Syuhei Yamaguchi, Yuki Miyake, Hidenori Yahiro
    • Organizer
      16th Korea-Japan Symposium on Catalysis
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Catalysis of perovskite-type oxide prepared by the decomposition of heteronuclear cyano complex2017

    • Author(s)
      Hidenori Yahiro, Syuhei Yamaguchi
    • Organizer
      the 12th Pacific Rim Conference on Ceramic and Glass Technology
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] 鉄錯体固定化モンモリロナイト触媒を用いた環状炭化水素類の酸化反応2017

    • Author(s)
      伊原大二朗,山口修平,八尋秀典
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 銅錯体固定化モンモリロナイト触媒を用いたチオアニソールの酸化反応2017

    • Author(s)
      山下祐輝,井場堅斗,山口修平,八尋秀典
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 銅錯体内包ゼオライト触媒を用いたベンゼン類の酸化反応2017

    • Author(s)
      十川誠,山口修平,八尋秀典
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] ゼオライト細孔内で安定化した銅-活性酸素種の有機基質に対する反応活性2017

    • Author(s)
      山口修平,十川誠,鈴木彰規,八尋秀典
    • Organizer
      第50回酸化反応討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 銅錯体内包カチオン交換ゼオライト触媒を用いたチオアニソールの選択酸化反応2017

    • Author(s)
      山口修平,楮本周也,十川誠,八尋秀典
    • Organizer
      第119回触媒討論会
    • Place of Presentation
      首都大学東京(東京都目黒区)
    • Related Report
      2016 Research-status Report
  • [Presentation] 種々の鉄錯体をモンモリロナイトに固定化した触媒を用いたベンゼンの部分酸化反応2017

    • Author(s)
      伊原大二朗,山口修平,八尋秀典
    • Organizer
      第119回触媒討論会
    • Place of Presentation
      首都大学東京(東京都目黒区)
    • Related Report
      2016 Research-status Report
  • [Presentation] Catalytic Activity of Copper(II)-Terpy Complexes Encapsulated into Supercages of Zeolite for Oxidation of Thioanisole with Hydrogen Peroxide2016

    • Author(s)
      Syuhei Yamaguchi, Akinori Suzuki, Hidenori Yahiro
    • Organizer
      19th Topical Meeting of the International Society of electrochemistry
    • Place of Presentation
      北京(中国)
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 銅錯体内包カチオン交換ゼオライト触媒を用いたチオアニソールの酸化反応2016

    • Author(s)
      山口修平,楮本周也,十川誠,八尋秀典
    • Organizer
      錯体化学会第66回討論会
    • Place of Presentation
      福岡大学(福岡県福岡市)
    • Related Report
      2016 Research-status Report
  • [Presentation] 鉄錯体固定化モンモリロナイト触媒を用いたベンゼンの酸化反応2016

    • Author(s)
      伊原大二朗,山口修平,八尋秀典
    • Organizer
      第118回触媒討論会
    • Place of Presentation
      岩手大学(岩手県盛岡市)
    • Related Report
      2016 Research-status Report
  • [Remarks] 愛媛大学大学理工学研究科物質生命工学専攻応用化学コース無機材料化学研究室

    • URL

      http://www.ach.ehime-u.ac.jp/solid/

    • Related Report
      2017 Research-status Report
  • [Remarks] 愛媛大学大学院理工学研究科物質生命工学専攻応用化学コース無機材料化学研究室

    • URL

      http://www.ach.ehime-u.ac.jp/solid/

    • Related Report
      2016 Research-status Report

URL: 

Published: 2016-04-21   Modified: 2020-03-30  

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