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2012 Fiscal Year Final Research Report

REVERSIBLE DEHYDROGENATION-HYDROGENATION OF TETRAHYDROQUINOLINE-QUINOLINE USING A SUPPORTED COPPER NANOPARTICLE CATALYST

Research Project

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Project/Area Number 23656512
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

MITSUDOME Takato  大阪大学, 基礎工学研究科, 助教 (00437360)

Project Period (FY) 2011 – 2012
Keywordsナノ粒子 / 銅 / 有機ハイドライド / 水素
Research Abstract

Copper nanoparticles synthesized on a titania surface (Cu/TiO2) act as an efficient heterogeneous catalyst for the reversible dehydrogenation and hydrogenation of tetrahydroquinoline-quinoline under an atmospheric pressure of H2 under mild reaction conditions. Furthermore, Cu/TiO2 was easily recovered from the reaction mixture and reusable without any loss of its efficiency.

  • Research Products

    (37 results)

All 2013 2012 2011 Other

All Journal Article (18 results) (of which Peer Reviewed: 18 results) Presentation (17 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Gold nanoparticle-catalyzed cyclocarbonylation of 2-aminophenols2013

    • Author(s)
      Akifumi Noujima , Takato Mitsudome ,Tomoo Mizugaki , Koichiro Jitsukawa ,Kiyotomi Kaneda
    • Journal Title

      Green Chem

      Volume: 15巻 Pages: 608 -611

    • DOI

      DOI,10.1039/C2GC36851J

    • Peer Reviewed
  • [Journal Article] Selective Hydrogenolysis of Glycerol to 1,2-Propanediol Using Heterogeneous Copper Nanoparticle ,Catalyst Derived from Cu-Al Hydrotalcite2013

    • Author(s)
      Tomoo Mizugaki , Racha Arundhathi ,Takato Mitsudome, Koichiro Jitsukawa ,Kiyotomi Kaneda
    • Journal Title

      Chem. Lett.

    • DOI

      DOI.org/10.1016/j.tetlet.2013.01.049

    • Peer Reviewed
  • [Journal Article] Simple and clean synthesis of ketones from internal olefins using PdCl2/N,N-dimethylacetamide catalyst system2013

    • Author(s)
      Takato Mitsudome , Syuhei Yoshida ,Yamato Tsubomoto , Tomoo Mizugaki ,Koichiro Jitsuawa, Kiyotomi Kaneda
    • Journal Title

      Tetrahedron Lett

      Volume: 54巻 Pages: 1596-1598

    • DOI

      DOI.org/10.1016/j.tetlet.2013.01.049

    • Peer Reviewed
  • [Journal Article] Highly Atom-Efficient Oxidation of Electron-Deficient Internal Olefins to Ketones Using Pd catalyst2013

    • Author(s)
      Takato Mitsudome , Syuhei Yoshida ,Tomoo Mizugaki , Koichiro Jitsukawa ,Kiyotomi Kaneda
    • Journal Title

      Angew. Chem. Int. Ed.

    • Peer Reviewed
  • [Journal Article] Metal-Ligand- Core-Shell Nanocomposite Catalysts for the SelectiveSemihydrogenation of Alkynes2013

    • Author(s)
      Takato Mitsudome , Yusuke Takahashi ,Satoshi Ichikawa , Tomoo Mizugaki ,Koichiro Jitsukawa , Kiyotomi Kaneda
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 52巻 Pages: 1481-1485

    • DOI

      DOI,10.1002/anie.201207845

    • Peer Reviewed
  • [Journal Article] Core-Shell AgNP@CeO2 Nanocomposite Catalyst for Highly Chemoselective Reductions of Unsaturated Aldehydes2013

    • Author(s)
      Takato Mitsudome , Motoshi Matoba ,Tomoo Mizugaki , Koichiro Jitsukawa ,Kiyotomi Kaneda
    • Journal Title

      Chem. Eur. J.

    • DOI

      DOI,10.1002/chem.201204160

    • Peer Reviewed
  • [Journal Article] Unique Catalysis of Gold Nanoparticles in the Chemoselective Hydrogenolysis with H2: CooperativeEffect between Small Gold Nanoparticles and a Basic Support2012

    • Author(s)
      Akifumi Noujima , Takato Mitsudome ,Tomoo Mizugaki , Koichiro Jitsukawa ,Kiyotomi Kaneda
    • Journal Title

      Chem. Commun.

      Volume: 48巻 Pages: 6723-6725

    • DOI

      DOI,10.1039/C2CC32850J

    • Peer Reviewed
  • [Journal Article] Selective Hydrogenolysis of Glycerol to 1,3-Propanediol Catalyzed by Pt Nanoparticles-AlOx/WO32012

    • Author(s)
      Tomoo Mizugaki , Takayuki Yamakawa ,Arundhathi Racha , Takato Mitsudome ,Koichiro Jitsukawa , Kiyotomi Kaneda
    • Journal Title

      Chem. Lett

      Volume: 41巻 Pages: 1720-1722

    • URL

      http://dx.doi.org/10.1246/cl.2012.1720

    • Peer Reviewed
  • [Journal Article] Highly Efficient Double-Carbonylation of Amines to Oxamides Using Gold Nanoparticle Catalysts2012

    • Author(s)
      Takato Mitsudome , Akifumi Noujima ,Tomoo Mizugaki , Koichiro Jitsukawa ,Kiyotomi Kaneda
    • Journal Title

      Chem. Commun

      Volume: 48巻 Pages: 11733-11735

    • DOI

      DOI,10.1039/C2CC36636C

    • Peer Reviewed
  • [Journal Article] Design of a Silver-Cerium Dioxide Core-Shell Nanocomposite Catalyst for Chemoselective Reduction Reactions.2012

    • Author(s)
      Takato Mitsudome , Yusuke Mikami ,Motoshi Matoba, Tomoo Mizugaki, Koichiro Jitsukawa ,Kiyotomi Kaneda
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51巻 Pages: 136-139

    • DOI

      DOI,10.1002/anie.201106244

    • Peer Reviewed
  • [Journal Article] Titanium Cation-exchanged Montmorillonite as an Active Heterogeneous Catalyst for the BeckmannRearrangement under Mild Reaction Conditions2012

    • Author(s)
      Takato Mitsudome , Tsuyoshi Matsuno ,Shoichiro Sueoka , Tomoo Mizugaki ,Koichiro Jitsukawa , Kiyotomi Kaneda
    • Journal Title

      Tetrahedron Lett

      Volume: 53巻 Pages: 5211-5214

    • URL

      http://dx.doi.org/10.1016/l.tetlet.2012.07.032

    • Peer Reviewed
  • [Journal Article] Direct synthesis of unsymmetrical ethers from alcohols catalyzed by titanium cation-exchanged Montmorillonite2012

    • Author(s)
      Takato Mitsudome , Tsuyoshi Matsuno ,Shoichiro Sueoka , Tomoo Mizugaki ,Koichiro Jitsukawa , Kiyotomi Kaneda
    • Journal Title

      Green Chem

      Volume: 14巻 Pages: 610-613

    • DOI

      DOI,10.1039/C2GC16135D

    • Peer Reviewed
  • [Journal Article] Highly efficient condensation of glycerol to cyclic acetals catalyzed by titanium-exchanged Montmorillonite2012

    • Author(s)
      Takato Mitsudome , Tsuyoshi Matsuno ,Shoichiro Sueoka , Tomoo Mizugaki ,Koichiro Jitsukawa , Kiyotomi Kaneda
    • Journal Title

      Heterocycles

      Volume: 84巻 Pages: 371 -376

    • DOI

      DOI,10.3987/COM-11-S(P)68

    • Peer Reviewed
  • [Journal Article] Highly Efficient Pd/SiO2-Dimethyl Sulfoxide Catalyst System for Selective Semihydrogenation of Alkynes2011

    • Author(s)
      Yusuke Takahashi, Norifumi Hashimoto,Takayoshi Hara, Shogo Shimazu, TakatoMitsudome, Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda
    • Journal Title

      Chem. Lett

      Volume: 40巻 Pages: 405-407

    • DOI

      DOI:10.1246/cl.2011.405

    • Peer Reviewed
  • [Journal Article] Gold nanoparticle-catalyzed environmentally benign deoxygenation of epoxides to alkenes2011

    • Author(s)
      Akifumi Noujima, Takato Mitsudome, Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda
    • Journal Title

      Molecules

      Volume: 16巻 Pages: 8209-8227

    • DOI

      DOI:10.3390/molecules16108209

    • Peer Reviewed
  • [Journal Article] Selective Deoxygenation of Epoxides to Alkenes with Molecular Hydrogen Using Hydrotalcitesupported Gold Catalyst , A Concerted Effect between Basic Sites and Gold Nanoparticles2011

    • Author(s)
      Akifumi Noujima, Takato Mitsudome, Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50巻 Pages: 2986-8989

    • DOI

      DOI:10.1002/ange.201007679

    • Peer Reviewed
  • [Journal Article] Highly Efficient Gold Nanoparticle-Catalyzed Deoxygenation of Amides, Sulfoxides and Pyridine Noxides2011

    • Author(s)
      Yusuke Mikami, Akifumi Noujima, Takato Mitsudome, Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda
    • Journal Title

      Chem. Eur. J

      Volume: 17巻 Pages: 1768-1772

    • DOI

      DOI:10.1002/chem.201003109

    • Peer Reviewed
  • [Journal Article] Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda ,Reversible Dehydrogenation-Hydrogenation of Tetrahydroquinoline-quinoline Using a supported Cooper Nanoparticle Catalyst2011

    • Author(s)
      Yusuke Mikami, Kaori Ebata, Takato Mitsudome, Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda
    • Journal Title

      Heterocycles

      Volume: 82巻 Pages: 1371-1377

    • DOI

      DOI:10.3987/COM-10-S(E)90

    • Peer Reviewed
  • [Presentation] アミン類の高効率カルボニル化反応を可能とする固定化金ナノ粒子触媒の開発2013

    • Author(s)
      能島明史, 満留敬人, 水垣共雄, 實川浩一郎, 金田清臣
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀県)
    • Year and Date
      2013-03-24
  • [Presentation] 不飽和アルデヒドの高選択的還元反応を可能とする Core-Shell 型銀ナノ粒子触媒の開発2013

    • Author(s)
      的場元志, 満留敬人, 水垣共雄, 實川浩一郎, 金田清臣
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀県)
    • Year and Date
      2013-03-23
  • [Presentation] Core-Shell 型銀ナノ粒子触媒を用いたエポキシドからアルケンへの環境調和型脱酸素反応2012

    • Author(s)
      的場元志, 満留敬人, 水垣共雄, 實川浩一郎, 金田清臣
    • Organizer
      第22回触媒学会キャラクタリゼーション講習会
    • Place of Presentation
      大阪大学(大阪府)
    • Year and Date
      2012-10-12
  • [Presentation] 選択的還元反応を可能にする Core-Shell 型銀ナノ粒子触媒の開発2012

    • Author(s)
      的場元志, 満留敬人, 水垣共雄, 實川浩一郎, 金田清臣
    • Organizer
      第110回触媒討論会
    • Place of Presentation
      九州大学(福岡県)
    • Year and Date
      2012-09-25
  • [Presentation] Design of Ag@CeO2 Core-shell nanocomposite catalyst for complete chemoselective reductions2012

    • Author(s)
      Takato Mitsudome, M. Matoba, T. Mizugaki, K.Jitsukawa, K. Kaneda
    • Organizer
      International Congress of Catalysis
    • Place of Presentation
      Berlin, ドイツ
    • Year and Date
      2012-07-07
  • [Presentation] 金ナノ粒子と塩基性担体の協奏効果を利用したエポキシドの環境調和型脱酸素反応2012

    • Author(s)
      能島明史, 満留敬人, 水垣共雄, 實川浩一郎, 金田清臣
    • Organizer
      第109回触媒討論会
    • Place of Presentation
      東京工業大学(東京)
    • Year and Date
      2012-03-29
  • [Presentation] 化学選択的還元反応を可能とする銀ナノ粒子触媒の開発2012

    • Author(s)
      満留敬人, 三上祐輔, 的場元志, 水垣共雄, 實川浩一郎, 金田清臣
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学(神奈川)
    • Year and Date
      2012-03-25
  • [Presentation] エポキシドの化学選択的還元反応に向けたハイドロタルサイト固定化金ナノ粒子触媒の開発2012

    • Author(s)
      能島明史, 山本功, 満留敬人, 水垣共雄, 實川浩一郎, 金田清臣
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学(神奈川)
    • Year and Date
      2012-03-25
  • [Presentation] Deoxygenation of Epoxides to Alkenes with H2 Catalyzed by Supported Gold Nanoparticles2011

    • Author(s)
      Akifumi Noujima, Takato Mitsudome, Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda
    • Organizer
      The 11th Global COE International Symposium ,Bio-Environmental Chemistry
    • Place of Presentation
      Osaka University (Osaka)
    • Year and Date
      2011-12-20
  • [Presentation] Highly efficient aerobic oxidation of alcohols and diols using hydrotalcite-supported gold nanoparticleCatalyst2011

    • Author(s)
      Akifumi Noujima, Takato Mitsudome, Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda
    • Organizer
      The 3rd Asia-Oceania Conference on Green and Sustainable Chemistry (AOC-3)
    • Place of Presentation
      Melbourne, Australia
    • Year and Date
      2011-12-06
  • [Presentation] 高選択的脱酸素反応を可能にするオリンピックメダル金属ナノ粒子触媒の開発2011

    • Author(s)
      満留敬人
    • Organizer
      高資源循環ポリマー研究センター第3回セミナー
    • Place of Presentation
      石川 北陸先端大
    • Year and Date
      2011-11-25
  • [Presentation] ニトロ化合物の官能基選択的還元反応を可能にする新規 Core-Shell 型銀ナノ粒子触媒の開発2011

    • Author(s)
      的場元志, 満留敬人, 三上祐輔, 水垣共雄, 實川浩一郎, 金田清臣
    • Organizer
      第4回触媒表面化学研究発表会
    • Place of Presentation
      関西大学(大阪)
    • Year and Date
      2011-11-04
  • [Presentation] アルコールから非対称エーテルへの直接変換反応におけるチタニウムカチオン交換モンモリロナイト触媒の開発2011

    • Author(s)
      松野剛士, 末岡祥一郎, 満留敬人, 水垣共雄, 實川浩一郎, 金田清臣
    • Organizer
      第4回触媒表面化学研究発表会
    • Place of Presentation
      関西大学(大阪)
    • Year and Date
      2011-11-04
  • [Presentation] 分子状水素を用いた高選択的還元反応を可能とする新規コア-シェル型 銀ナノ粒子触媒の開発2011

    • Author(s)
      満留敬人,三上祐輔,的場元志,水垣共雄,實川浩一郎,金田清臣
    • Organizer
      第108回触媒討論会
    • Place of Presentation
      北見工業大学(北海道)
    • Year and Date
      2011-09-20
  • [Presentation] Highly selective reduction of various oxygen-containing organic compounds using supported goldnanoparticle catalysts2011

    • Author(s)
      Akifumi Noujima, Takato Mitsudome, Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda
    • Organizer
      242nd ACS National Meeting & Exposition, Division ofCatalysis Science and Technology (probationary)
    • Place of Presentation
      Denver, Colorado,U.S.A
    • Year and Date
      2011-08-30
  • [Presentation] Novel Wacker-type Oxidation of internal olefins using molecular oxygen as the sole oxidant2011

    • Author(s)
      Takato Mitsudome, Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda
    • Organizer
      International symposium on activation of dioxygen and homogeneous catalytic oxidation
    • Place of Presentation
      Bankoku Shinryokan (Okinawa)
    • Year and Date
      2011-07-04
  • [Presentation] 金ナノ粒子固定化触媒を用いたアルコール類のグリーン酸化反応2011

    • Author(s)
      能島明史, 満留敬人, 水垣共雄, 實川浩一郎, 金田清臣
    • Organizer
      第11回GSCシンポジウム, グリーン・サステイナブル ケミストリーネットワーク
    • Place of Presentation
      早稲田大学・国際会議場(東京)
    • Year and Date
      2011-06-02
  • [Book] 重ねたり包み込んだり~固体触媒の新たなデザイン~2012

    • Author(s)
      満留敬人・實川浩一郎
    • Total Pages
      72-73
    • Publisher
      化学同人
  • [Remarks]

    • URL

      http://www.cheng.es.osaka-u.ac.jp/jitsukawalabo/home.html

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Published: 2014-09-25  

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