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Development of single-step synthesis of phenol over transition metal complexes encapsulated into zeolite

Research Project

Project/Area Number 25820394
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

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

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2015: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsフェノール合成 / ベンゼン酸化 / 固体触媒 / 金属錯体触媒 / ゼオライト / 一段階合成 / 過酸化水素 / 遷移金属内包ゼオライト触媒 / ベンゼン酸化反応 / フェノール選択性 / 溶媒効果 / カチオン交換 / 配位子の効果 / 遷移金属錯体内包ゼオライト触媒
Outline of Final Research Achievements

Phenols are valuable organic intermediates in the chemical industry. Most of these phenols are industrially produced by multistep processes. For example, a three step cumene process has been employed widely as a commercial process for the production of phenol. On the other hand, the direct catalytic hydroxylation of benzene to phenol with environment-friendly oxidants has attracted much attention.
Catalytic activity of iron complexes-encapsulated zeolite catalyst ([Fe(bpy)3]2+@Y) for oxidation of benzene increased with increasing the amount of water added into acetonitrile. Maximum value of catalytic activity was obtained, when the volume ratio of the solvents was equal (CH3CN : H2O = 1:1). After reaction at 24 h, the turnover number of [Fe(bpy)3]2+@Y was higher than that of [Fe(bpy)3](ClO4)2 as a homogeneous catalyst.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (40 results)

All 2016 2015 2014 2013 Other

All Journal Article (7 results) (of which Peer Reviewed: 4 results,  Acknowledgement Compliant: 4 results) Presentation (30 results) (of which Int'l Joint Research: 4 results,  Invited: 3 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] 遷移金属内包ゼオライト触媒を用いた選択的酸化反応2015

    • Author(s)
      山口修平、八尋秀典
    • Journal Title

      ゼオライト

      Volume: 32 Pages: 80-87

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Effect of water added into acetonitrile solvent on oxidation of benzene with hydrogen peroxide over iron complexes encapsulated in zeolite2015

    • Author(s)
      Syuhei Yamaguchi, Tetsuya Ohnishi, Yuki Miyake, Hidenori Yahiro
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 10 Pages: 1287-1288

    • DOI

      10.1246/cl.150479

    • NAID

      130005101462

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Selective hydroxylation of cyclohexene over Fe-bipyridine complexes encapsulated into Y-type zeolite under environment-friendly conditions2015

    • Author(s)
      Syuhei Yamaguchi, Tomohiro Fukura, Keiko Takiguchi, Chiharau Fujita, Maiko Nishibori, Yasutake Teraoka, Hidenori Yahiro
    • Journal Title

      Catalysis Today

      Volume: 242 Pages: 261-267

    • DOI

      10.1016/j.cattod.2014.07.038

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] 水溶媒中でもフェノールの一段階合成が可能な固体触媒の開発2015

    • Author(s)
      山口修平、八尋秀典
    • Journal Title

      ケミカルエンジニヤリング

      Volume: 60 Pages: 410-416

    • Related Report
      2015 Annual Research Report
    • Acknowledgement Compliant
  • [Journal Article] Cyanosilylation of benzaldehyde with TMSCN over perovskite-type oxide catalyst prepared by thermal decomposition of heteronuclear cyano complex precursors2015

    • Author(s)
      Syuhei Yamaguchi, Takahisa Okura, Hiroki Wada, Hiroyuki Yamaura, Hidenori Yahiro
    • Journal Title

      Research on Chemical Intermediates

      Volume: 未定巻 Issue: 12 Pages: 9551-9560

    • DOI

      10.1007/s11164-015-1980-y

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] ゼオライト細孔で安定化した銅-活性酸素種のチオアニソールに対する反応活性2014

    • Author(s)
      山口修平、鈴木彰規、八尋秀典
    • Journal Title

      触媒

      Volume: 56 Pages: 68-70

    • Related Report
      2013 Research-status Report
  • [Journal Article] 水溶液中でも選択的な酸化反応が可能な固体触媒の開発2013

    • Author(s)
      山口修平、八尋秀典
    • Journal Title

      化学工業

      Volume: 64 Pages: 22-27

    • Related Report
      2013 Research-status Report
  • [Presentation] 鉄錯体含有ゼオライト触媒を用いた分子状酸素を酸化剤とするシクロヘキセンの酸化反応2016

    • Author(s)
      三宅祐輝、山口修平、八尋秀典
    • Organizer
      第117回触媒討論会
    • Place of Presentation
      大阪市立大学(大阪府大阪市)
    • Year and Date
      2016-03-22
    • Related Report
      2015 Annual Research Report
  • [Presentation] Oxidation of benzene over iron-bipyridine complexes encapsulated in metal cation-exchanged zeolite2015

    • Author(s)
      Yuki Miyake, Syuhei Yamaguchi, Hidenori Yahiro
    • Organizer
      PACIFICHEM2015
    • Place of Presentation
      ホノルル(アメリカ)
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Catalytic activity of copper(II)-terpy complexes encapsulated into Y-type zeolite2015

    • Author(s)
      Syuhei Yamaguchi, Akinori Suzuki, Hidenori Yahiro
    • Organizer
      PACIFICHEM2015
    • Place of Presentation
      ホノルル(アメリカ)
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 鉄錯体内包カチオン交換ゼオイト触媒を用いたベンゼンの酸化反応2015

    • Author(s)
      山口修平、三宅祐輝、八尋秀典
    • Organizer
      錯体化学会第65回討論会
    • Place of Presentation
      奈良女子大学(奈良県奈良市)
    • Year and Date
      2015-09-22
    • Related Report
      2015 Annual Research Report
  • [Presentation] ゼオライト細孔に内包した遷移金属錯体を利用した選択的酸化反応2015

    • Author(s)
      山口修平、八尋秀典
    • Organizer
      第116回触媒討論会
    • Place of Presentation
      三重大学(三重県津市)
    • Year and Date
      2015-09-17
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 複核シアノ錯体前駆体の燃焼熱を利用した低温でのペロブスカイト型酸化物触媒の調製2015

    • Author(s)
      山口修平、和田啓暉、Daniel Sánchez-Rodríguez、八尋秀典
    • Organizer
      日本セラミックス協会第28回秋季シンポジウム
    • Place of Presentation
      富山大学(富山県富山市)
    • Year and Date
      2015-09-16
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Catalytic Activity of Copper(II)-Terpy Complexes Encapsulated into Supercages of Zeolite2015

    • Author(s)
      Syuhei Yamaguchi, Akinori Suzuki, Hidenori Yahiro
    • Organizer
      ZMPC2015
    • Place of Presentation
      札幌コンベンションセンター(北海道札幌市)
    • Year and Date
      2015-07-02
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Cyanosilylation of benzaldehyde with TMSCN over perovskite-type oxide catalyst prepared by thermal decomposition of heteronuclear cyano complex precursors2015

    • Author(s)
      Syuhei Yamaguchi, Takahisa Okuwa, Hiroki Wada, Hidenori Yahiro
    • Organizer
      11th International Conference on Ceramic Materials and Components for Energy and Environmental Applications
    • Place of Presentation
      バンクーバー(カナダ)
    • Year and Date
      2015-06-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 遷移金属錯体内包ゼオライト触媒を用いた有機基質の選択的酸化反応2015

    • Author(s)
      山口修平
    • Organizer
      平成27年度触媒学会西日本支部触媒技術セミナー
    • Place of Presentation
      愛媛大学(愛媛県松山市)
    • Year and Date
      2015-06-12
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Hydrooxylation of Benzene with Hydrogen Peroxide over Iron Complexes Encapsulated in Metal Cation-Exchanged Y-Type Zeolite2015

    • Author(s)
      三宅祐輝、山口修平、八尋秀典
    • Organizer
      触媒学会西日本支部第6回触媒科学研究発表会
    • Place of Presentation
      愛媛大学(愛媛県松山市)
    • Year and Date
      2015-06-12
    • Related Report
      2015 Annual Research Report
  • [Presentation] 銅錯体内包金属カチオン交換ゼオライト触媒を用いたスルフィド類の酸化反応2015

    • Author(s)
      三宅祐輝・久田啓輔・山口修平・八尋秀典
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Research-status Report
  • [Presentation] Selective hydroxylation of hydrocarbons over Fe complexes encapsulated in zeolite2015

    • Author(s)
      Syuhei Yamaguchi, Keiko Takiguchi, Yuki Miyake, Tomohiro Fukura, Hidenori Yahiro
    • Organizer
      Fourth International Conference on Multifuctional, Hybrid and Nanomaterials
    • Place of Presentation
      Sitges, Spain
    • Year and Date
      2015-03-09
    • Related Report
      2014 Research-status Report
  • [Presentation] 遷移金属錯体内包ゼオライト触媒を用いた有機基質に対する選択的酸化反応2014

    • Author(s)
      山口修平・八尋秀典
    • Organizer
      第30回ゼオライト研究発表会
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2014-11-26
    • Related Report
      2014 Research-status Report
  • [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選択的水酸化反応2014

    • Author(s)
      瀧口慶子・山口修平・八尋秀典
    • Organizer
      第30回ゼオライト研究発表会
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2014-11-26
    • Related Report
      2014 Research-status Report
  • [Presentation] 種々の鉄錯体を内包したゼオライト触媒を用いたベンゼンの酸化反応2014

    • Author(s)
      瀧口慶子・三宅祐輝・山口修平・八尋秀典
    • Organizer
      第114回触媒討論会
    • Place of Presentation
      広島大学(広島県東広島市)
    • Year and Date
      2014-09-26
    • Related Report
      2014 Research-status Report
  • [Presentation] カチオン交換ゼオライトに鉄錯体を内包した触媒を用いたベンゼンの酸化反応2014

    • Author(s)
      三宅祐輝・瀧口慶子・山口修平・八尋秀典
    • Organizer
      第114回触媒討論会
    • Place of Presentation
      広島大学(東広島市)
    • Year and Date
      2014-09-26
    • Related Report
      2014 Research-status Report
  • [Presentation] 銅錯体内包ゼオライト触媒と過酸化水素を用いた炭化水素類の酸化反応2014

    • Author(s)
      山口修平・鈴木彰規・久田啓輔・八尋秀典
    • Organizer
      錯体化学会第64回討論会
    • Place of Presentation
      中央大学(東京都文京区)
    • Year and Date
      2014-09-19
    • Related Report
      2014 Research-status Report
  • [Presentation] Oxidation of Cyclic Hydrocarbons with Hydrogen Peroxide over Iron Complexes Encapsulated in Zeolite2014

    • Author(s)
      瀧口慶子・山口修平・八尋秀典
    • Organizer
      平成26年度触媒学会西日本支部第5回触媒科学研究発表会
    • Place of Presentation
      名古屋大学(愛知県名古屋市)
    • Year and Date
      2014-06-13
    • Related Report
      2014 Research-status Report
  • [Presentation] ゼオライト細孔内で安定化した銅-活性酸素種のチオアニソールに対する反応活性2014

    • Author(s)
      山口修平・鈴木彰規・八尋秀典
    • Organizer
      第113回触媒討論会
    • Place of Presentation
      ロジワールホテル豊橋(豊橋)
    • Related Report
      2013 Research-status Report
  • [Presentation] 鉄錯体内包金属カチオン交換ゼオライト触媒を用いたベンゼンの酸化反応2014

    • Author(s)
      三宅祐輝・大西哲也・瀧口慶子・山口修平・八尋秀典
    • Organizer
      第113回触媒討論会
    • Place of Presentation
      ロジワールホテル豊橋(豊橋)
    • Related Report
      2013 Research-status Report
  • [Presentation] Selective Oxidation of Sulfides over Copper(II)-terpy Complexes in Zeolite Y Cagaes2013

    • Author(s)
      Akinori Suzuki, Yukari Baba, Syuhei Yamaguchi, Hidenori Yahiro
    • Organizer
      平成25年度触媒学会西日本支部第4回触媒科学研究発表会
    • Place of Presentation
      徳島大学(徳島)
    • Related Report
      2013 Research-status Report
  • [Presentation] Selective Oxidation of Sulfides over Copper(II)-terpy Complexes in Zeolite Y Cagaes2013

    • Author(s)
      Akinori Suzuki, Yukari Baba, Syuhei Yamaguchi, Hidenori Yahiro
    • Organizer
      The 14th Japan-Korea Symposium on Catalysis
    • Place of Presentation
      Wink Aichi (Nagoya)
    • Related Report
      2013 Research-status Report
  • [Presentation] Selective Hydroxylation of Cyclohexene over Fe-Bipyridine Complexes Encapsulated in Zeolite2013

    • Author(s)
      Syuhei Yamaguchi, Tomohiro Fukura, Chiharu Fujita, Hidenori Yahiro
    • Organizer
      International Conference on Biological Inorganic Chemistry 2013
    • Place of Presentation
      Grenoble (France)
    • Related Report
      2013 Research-status Report
  • [Presentation] 鉄-ビピリジン錯体 内包ゼオライト触媒を用いた炭化水素類の選択的水酸化反応2013

    • Author(s)
      山口修平・大西哲也・瀧口慶子・八尋秀典
    • Organizer
      第112回触媒討論会
    • Place of Presentation
      秋田大学(秋田)
    • Related Report
      2013 Research-status Report
  • [Presentation] 銅錯体内包ゼオライト触媒と過酸化水素を用いたチオアニソールの酸化反応2013

    • Author(s)
      山口修平・鈴木彰規・八尋秀典
    • Organizer
      錯体化学会第63回討論会
    • Place of Presentation
      琉球大学(沖縄)
    • Related Report
      2013 Research-status Report
  • [Presentation] 鉄錯体内包ゼオライト触媒を用いたシクロヘキセンの選択的水酸化反応2013

    • Author(s)
      山口修平・八尋秀典
    • Organizer
      2013年日本化学会中国四国支部大会(若手特別講演)
    • Place of Presentation
      広島大学東広島キャンパス(広島)
    • Related Report
      2013 Research-status Report
  • [Presentation] Hydroxylation of Cyclohexene with Hydrogen Peroxide over Iron Complexes Encapsulated in Zeolite2013

    • Author(s)
      Keiko Takiguchi, Syuhei Yamaguchi, Hidenori Yahiro
    • Organizer
      Novel Designed Surface and Catalysis for Greener Future: C&FC Pre-Symposium in Himeji
    • Place of Presentation
      イーグレ姫路(姫路)
    • Related Report
      2013 Research-status Report
  • [Presentation] Oxidation of benzene with hydrogen peroxide over iron complexes encapsulated in zeolite2013

    • Author(s)
      Syuhei Yamaguchi, Tetsuya Ohnishi, Keiko Takiguchi, Hidenori Yahiro
    • Organizer
      the 6th Japan-China Workshop on Environmental Catalysis and Eco-Materials
    • Place of Presentation
      愛媛大学(松山)
    • Related Report
      2013 Research-status Report
  • [Presentation] Selective oxidation of sulfides with hydrogen peroxide over copper(II)-terpy complexes in zeolite Y cages2013

    • Author(s)
      Akinori Suzuki, Syuhei Yamaguchi, Hidenori Yahiro
    • Organizer
      the 6th Japan-China Workshop on Environmental Catalysis and Eco-Materials
    • Place of Presentation
      愛媛大学(松山)
    • Related Report
      2013 Research-status Report
  • [Presentation] Oxidaiton of Hydrocarbons with Hydrogen Peroxide over Iron Complexes Encapsulated in Zeolite2013

    • Author(s)
      Keiko Takiguchi, Syuhei Yamaguchi, Hidenori Yahiro
    • Organizer
      the 6th Japan-China Workshop on Environmental Catalysis and Eco-Materials
    • Place of Presentation
      愛媛大学(松山)
    • Related Report
      2013 Research-status Report
  • [Book] 触媒の設計・反応制御 事例集2013

    • Author(s)
      山口修平、八尋秀典
    • Total Pages
      827
    • Publisher
      技術情報協会
    • Related Report
      2013 Research-status Report
  • [Remarks] 愛媛大学大学院理工学研究科物質生命工学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
      2015 Annual Research Report
  • [Patent(Industrial Property Rights)] フェノールの製造方法2014

    • Inventor(s)
      山口修平、八尋秀典
    • Industrial Property Rights Holder
      国立大学法人愛媛大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2014-030794
    • Filing Date
      2014-02-20
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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