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Development of base-metal nanocluster catalysts for synthesis of chemicals from sustainable carbon resources

Research Project

Project/Area Number 26289299
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Catalyst/Resource chemical process
Research InstitutionHokkaido University

Principal Investigator

Kenichi Shimizu  北海道大学, 触媒科学研究所, 教授 (60324000)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥15,600,000 (Direct Cost: ¥12,000,000、Indirect Cost: ¥3,600,000)
Fiscal Year 2016: ¥5,850,000 (Direct Cost: ¥4,500,000、Indirect Cost: ¥1,350,000)
Fiscal Year 2015: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2014: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Keywords触媒 / 二酸化炭素 / 化学品合成 / 金属ナノ粒子 / カルボン酸類 / 水素化反応 / 水素化 / サステナブルケミストリー / 有機合成 / アミド / バイオマス
Outline of Final Research Achievements

We studied heterogeneous catalytic methods for one-step reductive conversion of sustainable carbon sources (CO2, carboxylic acids) into chemicals. We developed three catalytic systems that convert carboxylic acids to esters, alcohols and alkanes, three catalytic systems that convert levulinic acid to pyrrolidones, valerolactone, and pentanoic acid and methods for methylation of amines under CO2+H2, amide hydrogenation, sulfoxide-sulfone hydrodeoxygenation. Each catalyst acted as a reusable heterogeneous catalyst and gave the target product in a high yield for a wide range of substrates. Mechanistic and structural studies showed a catalyst design guideline based on activation of C=O bond by Lewis acidic support and hydrogen dissociation on adjacent metal nanoparticles.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • Research Products

    (39 results)

All 2017 2016 2015 2014 Other

All Journal Article (28 results) (of which Peer Reviewed: 28 results,  Acknowledgement Compliant: 28 results,  Open Access: 2 results) Presentation (8 results) (of which Int'l Joint Research: 4 results,  Invited: 6 results) Remarks (3 results)

  • [Journal Article] Acceptorless dehydrogenation of N-heterocycles by supported Pt catalysts2017

    • Author(s)
      Sondomoyee K Moromi, S.M.A. Hakim Siddiki, Kenichi Kon, Takashi Toyao, Ken-ichi Shimizu
    • Journal Title

      Catalysis Today

      Volume: 281 Pages: 507-511

    • DOI

      10.1016/j.cattod.2016.06.027

    • NAID

      120006577365

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Heterogeneous platinum catalysts for direct synthesis of trimethylamine by N-methylation of ammonia and its surrogates with CO2/H22017

    • Author(s)
      Takashi Toyao, SMAH Siddiki, Keisuke Ishihara, Kenichi Kon, Wataru Onodera, Ken-ichi Shimizu
    • Journal Title

      Chemistry letters

      Volume: 46 Issue: 1 Pages: 68-70

    • DOI

      10.1246/cl.160875

    • NAID

      130005308322

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Atomic-Resolution HAADF-STEM Study of Ag/Al2O3 Catalysts for Borrowing-Hydrogen and Acceptorless Dehydrogenative Coupling Reactions of Alcohols2016

    • Author(s)
      Kenta Yoshida, Kenichi Kon,Ken-ichi Shimizu
    • Journal Title

      Topics in Catalysis

      Volume: 59 Issue: 19-20 Pages: 1740-1747

    • DOI

      10.1007/s11244-016-0695-7

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] TiO2-Supported Re as a General and Chemoselective Heterogeneous Catalyst for Hydrogenation of Carboxylic Acids to Alcohols2016

    • Author(s)
      T. Toyao, S. M. A. H. Siddiki, A. S. Touchy, W. Onodera, K. Kon, Y. Morita, T. Kamachi, K. Yoshizawa, and K. Shimizu
    • Journal Title

      Chem. Eur. J.

      Volume: 23 Issue: 5 Pages: 1001-1006

    • DOI

      10.1002/chem.201604762

    • NAID

      120006365325

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Catalytic hydrolysis of hydrophobic esters on/in water by high-silica large pore zeolites2016

    • Author(s)
      S.M.A Hakim Siddiki, Takashi Toyao, Kenichi Kon, Abeda S. Touchy, Ken-ichi Shimizu
    • Journal Title

      Journal of Catalysis

      Volume: 344 Pages: 741-748

    • DOI

      10.1016/j.jcat.2016.08.021

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Supported rhenium nanoparticle catalysts for acceptorless dehydrogenation of alcohols: structure-reactivity relationship and mechanistic studies2016

    • Author(s)
      Kenichi Kon, Wataru Onodera, Takashi Toyao, Ken-ichi Shimizu
    • Journal Title

      Catalysis Science & Technology

      Volume: 6 Issue: 15 Pages: 5864-5870

    • DOI

      10.1039/c6cy00252h

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts2016

    • Author(s)
      S.M.A. Hakim Siddiki, Abeda S. Touchy, Chandan Chaudhari, Kenichi Kon, Takashi Toyao, Ken-ichi Shimizu
    • Journal Title

      Organic Chemistry Frontiers

      Volume: 3 Issue: 7 Pages: 846-851

    • DOI

      10.1039/c6qo00165c

    • NAID

      120006318733

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Machine-learning prediction of d-band center for metals and bimetals2016

    • Author(s)
      I. Takigawa, K. Shimizu, K. Tsuda and S. Takakusagi
    • Journal Title

      RSC Advances

      Volume: 6 Issue: 58 Pages: 52587-52595

    • DOI

      10.1039/c6ra04345c

    • NAID

      120006219935

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Hydrodeoxygenation of sulfoxides to sulfides by a Pt and MoOx co-loaded TiO2 catalyst2016

    • Author(s)
      Abeda Sultana Touchy, S.M.A. Hakim Siddiki, Wataru Onodera, Kenichi Kon, Ken-ichi Shimizu
    • Journal Title

      Green Chemistry

      Volume: 18 Issue: 8 Pages: 2554-2560

    • DOI

      10.1039/c5gc02806j

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Lewis Acid-Promoted Heterogeneous Platinum Catalysts for Hydrogenation of Amides to Amines2016

    • Author(s)
      Ken-ichi Shimizu, Wataru Onodera, Abeda S. Touchy, S.M.A. Hakim Siddiki, Takashi Toyao, Kenichi Kon
    • Journal Title

      ChemistrySelect

      Volume: 4 Issue: 4 Pages: 736-740

    • DOI

      10.1002/slct.201600088

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct Olefination of Alcohols with Sulfones by Using Heterogeneous Platinum Catalysts2016

    • Author(s)
      S.M.A. Hakim Siddiki, Abeda Sultana Touchy, Kenichi Kon, Ken-ichi Shimizu
    • Journal Title

      Chemistry - A European Journal

      Volume: 22 Issue: 17 Pages: 6111-6119

    • DOI

      10.1002/chem.201505109

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct Synthesis of Cyclic Imides from Carboxylic Anhydrides and Amines by Nb2O5 as a water-tolerant Lewis acid Catalyst2016

    • Author(s)
      Md. A. Ali, Sondomoyee Konika Moromi, Abeda S. Touchy, Ken-ichi Shimizu
    • Journal Title

      ChemCatChem

      Volume: 8 Issue: 5 Pages: 891-894

    • DOI

      10.1002/cctc.201501172

    • NAID

      120005981354

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Amidation of Carboxylic Acids with Amines by Nb2O5 as a Reusable Lewis Acid Catalyst2015

    • Author(s)
      Md. A. Ali, S. M. A. H. Siddiki, Wataru Onodera, Kenichi Kon, Ken-ichi Shimizu
    • Journal Title

      ChemCatChem

      Volume: 7 Issue: 21 Pages: 3555-3561

    • DOI

      10.1002/cctc.201500672

    • NAID

      120005855946

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Heterogeneous Niobium(V) Oxide Catalyst for the Direct Amidation of Esters2015

    • Author(s)
      Md. A. Ali, S. M. A. H. Siddiki, Kenichi Kon, Ken-ichi Shimizu
    • Journal Title

      ChemCatChem

      Volume: 7 Issue: 17 Pages: 2705-2710

    • DOI

      10.1002/cctc.201500601

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Acceptorless dehydrogenative synthesis of benzothiazoles and benzimidazoles from alcohols or aldehydes by heterogeneous Pt catalysts under neutral conditions2015

    • Author(s)
      Chandan Chaudhari, S. M. A. Hakim Siddiki, Ken-ichi Shimizu
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 34 Pages: 4885-4888

    • DOI

      10.1016/j.tetlet.2015.06.073

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Unprecedented Reductive Esterification of Carboxylic Acids under Hydrogen by Reusable Heterogeneous Platinum Catalysts2015

    • Author(s)
      Abeda S. Touchy, Kenichi Kon, Wataru Onodera, Ken-ichi Shimizu
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 357 Issue: 7 Pages: 1499-1506

    • DOI

      10.1002/adsc.201401172

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Acceptorless dehydrogenative lactonization of diols by Pt-loaded SnO2 catalyst2015

    • Author(s)
      Abeda Sultana Touchy, Ken-ichi Shimizu
    • Journal Title

      RSC Advances

      Volume: 5 Issue: 37 Pages: 29072-29075

    • DOI

      10.1039/c5ra03337c

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Selective Synthesis of Primary Amines by Reductive Amination of Ketones with Ammonia over Supported Pt catalysts2015

    • Author(s)
      Yoichi Nakamura, Kenichi Kon, Abeda Sultana Touchy, Ken-ichi Shimizu, Wataru Ueda
    • Journal Title

      ChemCatChem

      Volume: 7 Issue: 6 Pages: 921-924

    • DOI

      10.1002/cctc.201402996

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Sustainable Heterogeneous Platinum Catalyst for Direct Methylation of Secondary Amines by Carbon Dioxide and Hydrogen2014

    • Author(s)
      Kenichi Kon,S.M.A. Hakim Siddiki, Wataru Onodera, Ken-ichi Shimizu
    • Journal Title

      CHEMISTRY-A EUROPEAN JOURNAL

      Volume: 20 Issue: 21 Pages: 6264-6267

    • DOI

      10.1002/chem.201400332

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Hydrogenation of levulinic acid to gamma-valerolactone by Ni and MoOx co-loaded carbon catalysts2014

    • Author(s)
      Ken-ichi Shimizu, Shota Kanno, Kenichi Kon
    • Journal Title

      GREEN CHEMISTRY

      Volume: 16 Issue: 8 Pages: 3899-3903

    • DOI

      10.1039/c4gc00735b

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Selective hydrogenation of levulinic acid to valeric acid and valeric biofuels by a Pt/HMFI catalyst2014

    • Author(s)
      Kenichi Kon, Wataru Onodera, Ken-ichi Shimizu
    • Journal Title

      CATALYSIS SCIENCE & TECHNOLOGY

      Volume: 4 Issue: 9 Pages: 3227-3234

    • DOI

      10.1039/c4cy00504j

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Heterogeneous Pt Catalysts for Reductive Amination of Levulinic Acid to Pyrrolidones2014

    • Author(s)
      Abeda Sultana Touchy, S.M.A. Hakim Siddiki, Kenichi Kon, Ken-ichi Shimizu
    • Journal Title

      ACS CATALYSIS

      Volume: 4 Issue: 9 Pages: 3045-3050

    • DOI

      10.1021/cs500757k

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Acceptorless dehydrogenative coupling of primary alcohols to esters by heterogeneous Pt catalysts2014

    • Author(s)
      Sondomoyee Konika Moromi, S.M.A. Hakim Siddiki, Md. Ayub Ali, Kenichi Kon, Ken-ichi Shimizu
    • Journal Title

      CATALYSIS SCIENCE & TECHNOLOGY

      Volume: 4 Issue: 10 Pages: 3631-3635

    • DOI

      10.1039/c4cy00979g

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Hydrodeoxygenation of fatty acids and triglycerides by Pt-loaded Nb2O5 catalysts2014

    • Author(s)
      Kenichi Kon, Wataru Onodera, Satoru Takakusagi, Ken-ichi Shimizu
    • Journal Title

      CATALYSIS SCIENCE & TECHNOLOGY

      Volume: 4 Issue: 10 Pages: 3705-3712

    • DOI

      10.1039/c4cy00757c

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Versatile and Sustainable Synthesis of Cyclic Imides from Dicarboxylic Acids and Amines by Nb2O5 as a Base-Tolerant Heterogeneous Lewis Acid Catalyst2014

    • Author(s)
      Md. Ayub Ali, S.M.A. Hakim Siddiki, Kenichi Kon, Junya Hasegawa, Ken-ichi Shimizu
    • Journal Title

      CHEMISTRY-A EUROPEAN JOURNAL

      Volume: 20 Issue: 44 Pages: 14256-14260

    • DOI

      10.1002/chem.201404538

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Acceptorless dehydrogenative synthesis of 2-substituted quinazolines from 2-aminobenzylamine with primary alcohols or aldehydes by heterogeneous Pt catalysts2014

    • Author(s)
      Chandan Chaudhari, S.M.A. Hakim Siddiki, Masazumi Tamura, Ken-ichi Shimizu
    • Journal Title

      RSC ADVANCES

      Volume: 4 Issue: 95 Pages: 53374-53379

    • DOI

      10.1039/c4ra09205h

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of indoles via dehydrogenative N-heterocyclization by supported platinum catalysts2014

    • Author(s)
      Sondomoyee Konika Moromi, Abeda Sultana Touchy, S.M.A. Hakim Siddiki, Md. Ayub Ali, Ken-ichi Shimizu
    • Journal Title

      RSC ADVANCES

      Volume: 5 Issue: 2 Pages: 1059-1062

    • DOI

      10.1039/c4ra11893f

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Selective N-alkylation of indoles with primary alcohols using a Pt/HBEA catalyst2014

    • Author(s)
      S.M.A. Hakim Siddiki, Kenichi Kon, Ken-ichi Shimizu
    • Journal Title

      GREEN CHEMISTRY

      Volume: 17 Issue: 1 Pages: 173-177

    • DOI

      10.1039/c4gc01419g

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] CeO2-catalyzed Transformations of Nitriles, Amides and Esters2016

    • Author(s)
      清水研一
    • Organizer
      Rare Earths 2016
    • Place of Presentation
      北海道大学(北海道札幌市)
    • Year and Date
      2016-06-05
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 酸化ニオブ上のLewis酸点によるカルボキシル基の活性化に関する実験・理論研究2016

    • Author(s)
      清水研一・Ali, Md. Ayub・今 健一 ・Hirunsit, Pussana・江原正博
    • Organizer
      第117回触媒討論会
    • Place of Presentation
      大阪府立大学(大阪府堺市)
    • Year and Date
      2016-03-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] Cooperative catalysis of Lewis acid and Pt cluster for hydrogenation of carboxylic acids, amides and CO22016

    • Author(s)
      清水研一
    • Organizer
      I2CNER International Workshop 2016
    • Place of Presentation
      九州大学伊都キャンパス(福岡県福岡市)
    • Year and Date
      2016-02-04
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 金属触媒における活性制御因子:実験・理論・情報科学によるアプローチ2016

    • Author(s)
      清水研一
    • Organizer
      日本金属学会2016年秋期講演大会公募シンポジウム
    • Place of Presentation
      大阪大学豊中キャンパス(大阪府吹田市)
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Heterogeneous catalysis for direct synthesis of chemicals from alcohols, CO2 and biomass platform compounds2015

    • Author(s)
      清水研一
    • Organizer
      25th Annual Saudi-Japan Symposium – 2015
    • Place of Presentation
      KFUPM, Dhahran, Saudi Arabia
    • Year and Date
      2015-12-07
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] "Sustainable heterogeneous catalysis for transformations of CO2 and biomass platform compounds into chemicals2015

    • Author(s)
      清水研一
    • Organizer
      7th China-Japan Workshop on Environmental Catalysis and Eco-Materials
    • Place of Presentation
      South China University of Technology, Guangzhou, China
    • Year and Date
      2015-11-06
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Lewis酸性酸化物担持Pt触媒による二酸化炭素・カルボン酸の還元的官能基変換2015

    • Author(s)
      清水研一, S. M. A. H. Siddiki, Abeda S. Touchy, 今健一
    • Organizer
      第115回触媒討論会
    • Place of Presentation
      東京都武蔵野市, 成蹊大学
    • Year and Date
      2015-03-23
    • Related Report
      2014 Annual Research Report
  • [Presentation] 二酸化炭素・カルボン酸を還元的に化学品・燃料に変換する固体触媒2014

    • Author(s)
      清水研一
    • Organizer
      第114回触媒討論会
    • Place of Presentation
      広島県東広島市, 広島大学
    • Year and Date
      2014-09-25
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Remarks] 研究室のホームページ

    • URL

      http://www.cat.hokudai.ac.jp/shimizu/index.html

    • Related Report
      2016 Annual Research Report
  • [Remarks] 研究室のwebページ

    • URL

      http://www.cat.hokudai.ac.jp/shimizu/

    • Related Report
      2015 Annual Research Report
  • [Remarks]

    • URL

      http://www.cat.hokudai.ac.jp/shimizu/

    • Related Report
      2014 Annual Research Report

URL: 

Published: 2014-04-04   Modified: 2018-03-22  

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