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Practical reactions with ceria and zirconia supported noble metal catalysts

Research Project

Project/Area Number 19H02755
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 34030:Green sustainable chemistry and environmental chemistry-related
Research InstitutionKyushu University

Principal Investigator

Tokunaga Makoto  九州大学, 理学研究院, 教授 (40301767)

Co-Investigator(Kenkyū-buntansha) 山本 英治  九州大学, 理学研究院, 助教 (70782944)
村山 美乃  九州大学, 理学研究院, 准教授 (90426528)
Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2021: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2020: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥9,230,000 (Direct Cost: ¥7,100,000、Indirect Cost: ¥2,130,000)
Keywords不均一系触媒 / 有機反応 / ソフトルイス酸 / 触媒再利用 / 流通式反応 / 金 / パラジウム / 白金 / ジルコニア / セリア / 担持触媒 / ソフトルイス酸機能 / アルケン活性化 / 触媒担体 / アルキニルカルボン酸 / 担持貴金属触媒 / 合成反応
Outline of Research at the Start

無機酸化物担持貴金属触媒は、自動車触媒などで汎用化されており、低コスト、優れた耐久性、大量生産可能、焼成で触媒再生が可能などの利点があるが、有機合成、有機反応への適用が不十分で、未開発の機能が埋もれている。そこで我々は、金、白金、パラジウム、ルテニウムなどの担持触媒の新機能開発を行う。担体として、高活性を示すことが多いセリア(CeO2) やジルコニア (ZrO2) を用い、酸化還元機能とソフトルイス酸機能の解明と応用を行う。ソフトルイス酸機能はアルケン、アルキン、芳香族などのπ電子を活性化するソフトな金属特有の機能であるが担持貴金属触媒では触媒設計指針が確立されておらず、それを目指す。

Outline of Final Research Achievements

The soft Lewis acid function activates the π-electrons of alkenes, alkynes, and aromatics. The conversion of alkenes and alkynes catalyzed by gold complexes has made great progress, especially in organic synthesis, but its practicality is not sufficient due to problems such as catalyst turnover, reusability, and requirements of chromatographic separation. We have summarized the information obtained on the soft Lewis acid function of supported noble metal nanoparticles by optimizing catalysts in reactions involving six different soft Lewis acid reactions. For example, in the allylic isomerization reaction catalyzed by supported gold nanoparticles, the smaller the particle size, the higher the partial pressure of oxygen, and the higher the density of gold nanoparticles per specific surface area of the support, the higher the activity.

Academic Significance and Societal Importance of the Research Achievements

不均一系触媒、担持触媒による合成反応は、反応混合物からの触媒の分離が容易で、再利用や流通式反応が可能であるので、均一系触媒に比べて実用的に有利である。我々は、金、パラジウム、白金、ルテニウムなどの担持触媒によるソフトルイス酸触媒反応の開発や機能解明を行い、これまで担持触媒では不可能だった反応をいくつか可能にした。その機能を発揮するための、触媒調製法なども新たに開発した。実際に、工業的に有用な反応でも、優れた触媒活性や耐久性を示すことを実証しており、工業生産への応用も検討している。

Report

(4 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • Research Products

    (18 results)

All 2021 2020 2019

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Open Access: 2 results) Presentation (3 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results) Book (3 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] C-H bond functionalization using Pd and Au supported catalysts with mechanistic insights of the active species2021

    • Author(s)
      Ishida, T. 他
    • Journal Title

      Synthesis

      Volume: 53 Issue: 18 Pages: 3279-3289

    • DOI

      10.1055/a-1468-1455

    • Related Report
      2021 Annual Research Report 2020 Annual Research Report 2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Continuous-flow synthesis of Pd@Pt core-shell nanoparticles2021

    • Author(s)
      Hashiguchi Yuta、Watanabe Fumihiro、Honma Tetsuo、Nakamura Isao、Poly Sharmin Sultana、Kawaguchi Tatsuya、Tsuji Tetsurou、Murayama Haruno、Tokunaga Makoto、Fujitani Tadahiro
    • Journal Title

      Colloids and Surfaces A: Physicochemical and Engineering Aspects

      Volume: 620 Pages: 126607-126607

    • DOI

      10.1016/j.colsurfa.2021.126607

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pt/CeO2 with residual chloride as reusable soft Lewis acid catalysts: Application to highly efficient isomerization of allylic esters2021

    • Author(s)
      Huang Qi-An、Haruta Asahi、Kumamoto Yuhya、Murayama Haruno、Yamamoto Eiji、Honma Tetsuo、Okumura Mitsutaka、Nobutou Hiroki、Tokunaga Makoto
    • Journal Title

      Applied Catalysis B: Environmental

      Volume: 296 Pages: 120333-120333

    • DOI

      10.1016/j.apcatb.2021.120333

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Convenient Unsymmetrical Disulfane Synthesis: Basic Zeolite‐Catalyzed Thiol‐Disulfane Exchange Reaction2021

    • Author(s)
      Yamamoto Eiji、Kawai Yasutaka、Takakura Kei、Kimura Moemi、Murayama Haruno、Matsueda Hironobu、Otsuki Shujiro、Sakata Hiroshi、Tokunaga Makoto
    • Journal Title

      ChemCatChem

      Volume: 13 Issue: 22 Pages: 4694-4699

    • DOI

      10.1002/cctc.202101092

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dynamic Kinetic Resolution of Azlactones via Phase-Transfer Catalytic Alcoholysis2021

    • Author(s)
      Wakafuji Kodai、Iwasa Satsuki、Ouchida Kina N.、Cho Hyemin、Dohi Hirotsugu、Yamamoto Eiji、Kamachi Takashi、Tokunaga Makoto
    • Journal Title

      ACS Catalysis

      Volume: 11 Issue: 22 Pages: 14067-14075

    • DOI

      10.1021/acscatal.1c03076

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] DFT study for selective adsorption of 1, 3-dimethyltrisulfane responsible for aged odor in Japanese sake using supported gold nanoparticles2020

    • Author(s)
      Ayaka Sonoura, Akihide Hayashi, Yoshinori Ato, Hiroaki Koga, Haruno Murayama, Makoto Tokunaga, Mitsutaka Okumura
    • Journal Title

      Chemistry Letters

      Volume: 49 Issue: 3 Pages: 218-221

    • DOI

      10.1246/cl.190868

    • NAID

      130007805889

    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Theoretical study of selective hydrogenolysis of methyl vinyl carbinol over Au-Ni bimetallic catalyst: Toward constructing a working hypothesis for the role of dichloroethane solvent and perimeter sites2020

    • Author(s)
      Ato Yoshinori、Hayashi Akihide、Sonoura Ayaka、Koga Hiroaki、Ishida Tamao、Tokunaga Makoto、Okumura Mitsutaka
    • Journal Title

      Chemical Physics Letters

      Volume: 754 Pages: 137773-137773

    • DOI

      10.1016/j.cplett.2020.137773

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structures analyses of supported ruthenium catalysts under asymmetric hydrogenation reaction2020

    • Author(s)
      Murayama, H.他
    • Journal Title

      Rad. Phys. Chem.

      Volume: 175 Pages: 108158-108158

    • DOI

      10.1016/j.radphyschem.2019.02.017

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Presentation] ナトリウム修飾した担持金ナノ粒子触媒によるアルキニルカルボン酸の分子内環化反応2021

    • Author(s)
      黄 啓安、川相 誓也、池田 孝明、山本 英治、村山 美乃、石田 玉青、徳永 信
    • Organizer
      第128回触媒討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Catalytic Isomerization of Allylic Esters over Supported Pt and Au Nano-catalysts via Soft Lewis Acid Mechanism2021

    • Author(s)
      Q.-A. Huang, A. Haruta, H. Murayama, E. Yamamoto, T. Ishida, T. Honma, Y. Izawa, S. Taniguchi, M. Tokunaga
    • Organizer
      1st Japan-China Symposium on Catalysis (1stJCSC)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 有機化学と固体触媒の接点:合成反応から酒類の香りの制御まで2020

    • Author(s)
      徳永 信
    • Organizer
      九州工業大学応用化学科講演会
    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
    • Invited
  • [Book] 最新吸着技術便覧 プロセス・材料・設計 新訂三版2020

    • Author(s)
      村山美乃、徳永 信、磯谷敦子
    • Total Pages
      856
    • Publisher
      NTS出版
    • ISBN
      9784860436902
    • Related Report
      2020 Annual Research Report
  • [Book] 放射光学会誌2020

    • Author(s)
      村山美乃、磯谷敦子、徳永 信
    • Total Pages
      250
    • Publisher
      放射光学会
    • Related Report
      2020 Annual Research Report
  • [Book] 最新吸着技術便覧 プロセス・材料・設計 新訂三版 監修 竹内 雍、NTS出版2020

    • Author(s)
      村山美乃、徳永 信、磯谷敦子
    • Total Pages
      9
    • Publisher
      NTS出版
    • Related Report
      2019 Annual Research Report
  • [Patent(Industrial Property Rights)] エステル化合物の製造方法2020

    • Inventor(s)
      徳永信、村山美乃、山本英治、シムジュヨン、森陽暉ほか
    • Industrial Property Rights Holder
      徳永信、村山美乃、山本英治、シムジュヨン、森陽暉ほか
    • Industrial Property Rights Type
      特許
    • Filing Date
      2020
    • Related Report
      2020 Annual Research Report
  • [Patent(Industrial Property Rights)] エステル化合物の製造方法2020

    • Inventor(s)
      徳永信他
    • Industrial Property Rights Holder
      九州大学他
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2020-088890
    • Filing Date
      2020
    • Related Report
      2019 Annual Research Report
  • [Patent(Industrial Property Rights)] アリル化合物の異性化方法2019

    • Inventor(s)
      谷口翔平、井澤雄輔、徳永 信、村山美乃、山本英治、石田玉青
    • Industrial Property Rights Holder
      谷口翔平、井澤雄輔、徳永 信、村山美乃、山本英治、石田玉青
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Acquisition Date
      2021
    • Related Report
      2021 Annual Research Report
  • [Patent(Industrial Property Rights)] 後周期遷移金属微粒子担持体の製造方法2019

    • Inventor(s)
      徳永 信、石田 玉青、山本 裕典、長谷川 貴之、村山 美乃ほか
    • Industrial Property Rights Holder
      徳永 信、石田 玉青、山本 裕典、長谷川 貴之、村山 美乃ほか
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Acquisition Date
      2022
    • Related Report
      2021 Annual Research Report

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Published: 2019-04-18   Modified: 2023-01-30  

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