Development of Highly Active Self-Assembled Solid Catalysts

• Project/Area Number: 24550126
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: The Institute of Physical and Chemical Research
• Principal Investigator: YAMADA Yoichi M. A. 独立行政法人理化学研究所, 環境資源科学研究センター, 副チームリーダー (50317723)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Project Status: Completed (Fiscal Year 2014)
• Budget Amount: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000); Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2013: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2012: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
• Keywords: ナノ粒子触媒 / 合金触媒 / カップリング反応 / 水素化反応 / 空気酸化反応 / アセタール化反応 / マイクロリアクター / 触媒膜 / 酸化反応 / 有機合成化学 / 固定化触媒 / 高分子金属触媒 / シリコン基板 / 有機金属化学 / 触媒

Outline of Final Research Achievements

A variety of highly active supported catalyst was developed. A Co-Pd alloy nanoparticle catalyst was developed and applied to the aerobic oxidation of alcohols. A Ni-Ru-Pt-Au alloy nanoparticle catalysts were prepared and applied to the hydrogenation of alkenes bearing a functional group.
A self-assembled catalyst of a polymeric imidazole and Pd was applied to the Mizoroki-Heck reaction. The local structure of the catalyst was revealed with XAFS and some analyses.
A catalytic acid membrane-installed microflow reactor was prepared and applied to the acetal formnation.

Research Products

• [Journal Article] A Convoluted Polymeric Imidazole Palladium Catalyst: Structural Elucidation and Investigation of Driving Force for Efficient Mizoroki-Heck Reaction (2015)
  • Author(s): Takuma Sato, Aya Ohno, Shaheen M. Sarkar, Yasuhiro Uozumi,* Yoichi M. A. Yamada*
  • Journal Title: ChemCatChem Volume: (accepted)
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Bimetallic Co-Pd Alloy Nanoparticles as Magnetically Recoverable Catalysts for the Aerobic Oxidation of Alcohols in Water (2014)
  • Author(s): Yoshikazu Ito, Hidetoshi Ohta, Yoichi M. A. Yamada*, Toshiaki Enoki, Yasuhiro Uozumi*
  • Journal Title: Tetrahedron Volume: 70 Issue: 36 Pages: 6146-6149
  • DOI: 10.1016/j.tet.2014.03.108
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Transfer Hydrogenation of Alkenes with a Ni/Ru/Pt/Au Heteroquatermetallic Nanoparticle Catalyst: Sequential Cooperation of Multiple Nano-Metal Species (2014)
  • Author(s): Yoshikazu Ito, Hidetoshi Ohta, Yoichi M. A. Yamada, Toshiaki Enoki, Yasuhiro Uozumi*
  • Journal Title: Chem. Commun. Volume: 50 Issue: 81 Pages: 12123-12126
  • DOI: 10.1039/c4cc04559a
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Driving an Equilibrium Acetalization to Completion in the Presence of Water (2014)
  • Author(s): Maki Minakawa, Yoichi M. A. Yamada, Yasuhiro Uozumi*
  • Journal Title: RSC Advances Volume: 4 Issue: 69 Pages: 36864-36867
  • DOI: 10.1039/c4ra07116f
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Hybrid of Palladium Nanoparticles and Silicon Nanowire Ar-ray: A Platform for Catalytic Heterogeneous Reactions (2014)
  • Author(s): Yamada Y.A.M, Yuyama Y, Sato T, Fujikawa S, Uozumi Y
  • Journal Title: Angew. Chem. Int. Ed Volume: 53 Issue: 1 Pages: 127-131
  • DOI: 10.1002/anie.201308541
  • Peer Reviewed
• [Journal Article] Polymeric Bimetallic Catalyst-Promoted In-Water Dehydrative Alkylation of Ammonia and Amines with Alcohols (2013)
  • Author(s): Yamada M.A.Y, Ohta H, Yuyama Y, Uozumi Y
  • Journal Title: Synthesis Volume: 45 Issue: 15 Pages: 2093-2100
  • DOI: 10.1055/s-0033-1338797
  • Peer Reviewed
• [Journal Article] Highly Efficient Iron(0) Nanoparticle-Catalyzed Hydrogenation in Water in Flow (2013)
  • Author(s): Hudson R, Hamasaka G, Osako T, Yamada M.A.Y, Li C.-J, Uozumi Y, Moores A
  • Journal Title: Green Chem. Volume: 15 Issue: 8 Pages: 2141-2148
  • DOI: 10.1039/c3gc40789f
  • Peer Reviewed
• [Journal Article] Direct Dehydrative Esterification of Alcohols and Carboxylic Acids with a Macroporous Polymeric Acid Catalyst (2013)
  • Author(s): M. Minakawa, H. Baek, Y. M. A. Yamada,* J. Han and Y. Uozumi*
  • Journal Title: Org. Lett. Volume: 15 Issue: 22 Pages: 5798-5801
  • DOI: 10.1021/ol4028495
  • Peer Reviewed
• [Journal Article] a Polymeric Bimetallic Catalyst-Promoted Dehydrative Alkylation of Ammonia and Amines with Alcohols in water (2013)
  • Author(s): Y. M. A. Yamada, H. Ohta, Y. Yuyama, and Y. Uozumi
  • Journal Title: Synthesis Volume: -
  • Peer Reviewed
• [Journal Article] Development of Polymeric Pd Nanoparticle Membrane-Installed Microflow Devices and Their Application in Hydrodehalogenation (2012)
  • Author(s): Y. M. A. Yamada, T. Watanabe, A. Ohno, and Y. Uozumi
  • Journal Title: ChemSusChem Volume: 5 Issue: 2 Pages: 293-299
  • DOI: 10.1002/cssc.201100418
  • Peer Reviewed
• [Journal Article] Self-Assembled Poly(imidazole-palladium) : Highly Active, Reusable Catalyst at Parts per Milion to Parts per Billion Levels (2012)
  • Author(s): Uozumi Y
  • Journal Title: J.Am.Chem.Soc. Volume: 134 Issue: 6 Pages: 3190-3198
  • DOI: 10.1021/ja210772v
  • Peer Reviewed
• [Journal Article] An Amphiphilic Self-Assembled Polymeric Copper Catalyst at Ppm Level: Click Chemistry (2012)
  • Author(s): Y. M. A. Yamada, S. M. Sarkar, and Y. Uozumi
  • Journal Title: J. Am. Chem. Soc Volume: 134 Issue: 22 Pages: 9285-9290
  • DOI: 10.1021/ja3036543
  • Peer Reviewed
• [Presentation] A Silicon Nanowire Array-Stabilized Palladium Nanoparticle Catalyst (2015)
  • Author(s): Yoichi M. A. Yamada
  • Organizer: Asian International Symposium –Organic Green Chemistry in 95th Japan Chemical Society Annual Meeting
  • Place of Presentation: Nihon University
  • Year and Date: 2015-03-27
  • Invited
• [Presentation] Transesterification of Various Alcohols and Esters Using a Porous Phenol Sulfonic Acid-Formaldehyde Resin Catalyst (2015)
  • Author(s): Heeyoel Baek, Minakawa Maki, Yamada M. A. Yoichi, Han Jin Wook, Uozumi Yasuhiro
  • Organizer: The 95th Annual Meeting 2015 of CSJ
  • Place of Presentation: Nihon University
  • Year and Date: 2015-03-27
• [Presentation] 自己組織化高分子イミダゾールニッケル触媒の開発とクロスカップリング反応への応用 (2015)
  • Author(s): 石井梨夏子、大野綾、山田陽一、魚住泰広
  • Organizer: 日本化学会第９５春期年会
  • Place of Presentation: 日本大学
  • Year and Date: 2015-03-27
• [Presentation] 両親媒性自己組織化高分子パラジウム触媒MPPI-Pd：溝呂木-Heck反応および構造解析 (2015)
  • Author(s): 佐藤太久真、大野綾、Sarkar, Shaheen M.、山田陽一、魚住泰広
  • Organizer: 日本化学会第９５春期年会
  • Place of Presentation: 日本大学
  • Year and Date: 2015-03-27
• [Presentation] 自己組織化高分子ピリジンパラジウム触媒による水中鈴木-宮浦反応 (2015)
  • Author(s): 大野綾、佐藤太久真、山田陽一、魚住泰広
  • Organizer: 日本化学会第９５春期年会
  • Place of Presentation: 日本大学
  • Year and Date: 2015-03-27
• [Presentation] 固定化触媒高活性化のための方法論開拓 (2015)
  • Author(s): 山田陽一
  • Organizer: 平成26年度 JST ACT-C 進歩ジウム in 岡山
  • Place of Presentation: 岡山大学
  • Year and Date: 2015-02-21
  • Invited
• [Presentation] A Silicon Nanowire Array-Stabilized Palladium Nanoparticle Catalyst for Mizoroki-Heck Reaction, C-H Bond Functionalizations, and Hydrogenations (2014)
  • Author(s): Y. M. A. Yamada, Y. Yuyama, T. Sato, S. Fujikawa, Y. Uozumi
  • Organizer: The 9th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-9/NICCEOCA-5)
  • Place of Presentation: クアラルンプール（マレーシア）
  • Year and Date: 2014-12-04
• [Presentation] Direct Dehydrative Esterification of Alcohols and Carboxylic Acids with a Macroporous Polymeric Acid Catalyst (2014)
  • Author(s): Heeyoel baek, Minakawa Maki, Yamada M. A. Yoichi, Han Jin Wook, Uozumi Yasuhiro
  • Organizer: 45th Annual Meeting of Union of Chemistry-Related Societies in Chubu Area
  • Place of Presentation: Chubu University
  • Year and Date: 2014-11-29
• [Presentation] Development of a Silicon Nanowire Array-Supported Palladium Nanoparticles and Their Application to Catalytic Organic Transformations (2014)
  • Author(s): Y. M. A. Yamada, Y. Yuyama, T. Sato, S. Fujikawa, Y. Uozumi
  • Organizer: The XXVI International Conference on Organometallic Chemistry (ICOMC 2014), 札幌，2014年7月
  • Place of Presentation: Sapporo
  • Year and Date: 2014-07-17
• [Presentation] Supported Catalysts in Batch & Flow (2014)
  • Author(s): Yoichi M. A. Yamada
  • Organizer: Guest Lecture at Pharmathen
  • Place of Presentation: Pharmathen, Thessaloniki, Greece
  • Year and Date: 2014-06-20
  • Invited
• [Presentation] Supported Catalysts in Batch & Flow (2014)
  • Author(s): Yoichi M. A. Yamada
  • Organizer: Guest Lecture at Aristotle University of Thessaloniki
  • Place of Presentation: Aristotle University of Thessaloniki
  • Year and Date: 2014-06-19
  • Invited
• [Presentation] 触媒膜導入型フローマイクロリアクターの開発へ
  • Author(s): 山田陽一
  • Organizer: フロー・マイクロ合成研究会第58回研究会
  • Place of Presentation: 大阪
  • Invited
• [Presentation] 不溶性高分子金属触媒
  • Author(s): 山田陽一
  • Organizer: 理研-九州大学ワークショップ －グリーン・ライフと機能材料－
  • Place of Presentation: 福岡
  • Invited
• [Presentation] 固定化触媒：バッチ＆フローシステム
  • Author(s): 山田陽一
  • Organizer: 第1回柴崎研究セミナー
  • Place of Presentation: 東京
  • Invited
• [Presentation] 分子もつれ法による高分子金属触媒開発 バッチ＆マイクロフロー
  • Author(s): 山田陽一
  • Organizer: 静岡大学大学院工学研究科化学バイオ工学専攻セミナー
  • Place of Presentation: 浜松
  • Invited
• [Presentation] 第1部「高活性・高再利用性高分子金属触媒の開発」
  • Author(s): 山田陽一
  • Organizer: 和歌山県工業技術センター 合成技術講習会
  • Place of Presentation: 和歌山
  • Invited
• [Presentation] 第2部「触媒膜導入型フローマイクロデバイスの開発」
  • Author(s): 山田陽一
  • Organizer: 和歌山県工業技術センター 合成技術講習会
  • Place of Presentation: 和歌山
  • Invited
• [Presentation] Supported Catalysts: Micro- to Nano-Space
  • Author(s): 山田陽一
  • Organizer: 分子科学研究所・総合研究大学院大学セミナー
  • Place of Presentation: 岡崎
  • Invited
• [Presentation] Convoluted Polymeric Metal Catalysts
  • Author(s): Yoichi M. A. Yamada
  • Organizer: RIKEN-ICCAS-IOP-PKU-Tsinghua Joint Symposium
  • Place of Presentation: Wako
  • Invited
• [Presentation] Convoluted Polymeric Cu Catalysts for Batch & Microflow Huisgen Cyclization
  • Author(s): Yoichi M. A. Yamada
  • Organizer: The 8th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-8) & The 4th New Phase International Conference on Cutting-Edge Organic Chemistry in Asia (NICCEOCA-4)
  • Place of Presentation: Osaka
  • Invited
• [Presentation] Polymeric Metal Catalysis: Batch & Microflow, Polymeric Metal Catalysis: Batch & Microflow
  • Author(s): Yoichi M. A. Yamada
  • Organizer: 10th Green Elements Science Symposium (International Symposium)
  • Place of Presentation: Okayama
  • Invited
• [Presentation] 高活性・高再利用性高分子銅触媒によるヒュスゲン反応： バッチ反応とマイクロフロー反応
  • Author(s): 山田陽一、Shaheen M. Sarkar、大野綾、佐藤太久真、魚住泰広
  • Organizer: 第60回有機金属化学討論会
  • Place of Presentation: 東京
• [Presentation] パラジウムナノ粒子シリコンナノワイヤー構造体ハイブリッド触媒による有機変換反応
  • Author(s): 佐藤 太久真・湯山 喜也・山田 陽一・藤川 茂紀・魚住 泰広
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋
• [Presentation] Highly Active Self-Assembled Polymeric Imidazole Pd Catalyst for Coupling Reactions
  • Author(s): Y. M. A. Yamada, S. M. Sarkar, Y. Uozumi
  • Organizer: OMCOS 17 (IUPAC)
  • Place of Presentation: Fort Collins, USA
• [Presentation] Self-Assembled Polymeric Metal Catalysts and Catalytic Membrane-Installed Microflow Reactors
  • Author(s): 山田陽一
  • Organizer: CAS-RIKEN Frontier Science Workshop 2012
  • Place of Presentation: 大磯プリンスホテル（神奈川県大磯町）
  • Invited
• [Presentation] 高活性で再利用可能な高分子金属触媒の開発とマイクロリアクターへの応用
  • Author(s): 山田陽一
  • Organizer: 平成24年度 前期（春季）有機合成化学講習会
  • Place of Presentation: 日本薬学会長井記念ホール（東京都渋谷区）
  • Invited
• [Presentation] Self-Organized Pd Nanocatalyst for Organic Reactions
  • Author(s): 山田陽一
  • Organizer: 錯体化学会第62回討論会 ミニシンポジウム
  • Place of Presentation: 富山大学五福キャンパス（富山県富山市）
  • Invited
• [Presentation] カップリング反応に有効な自己組織化高分子イミダゾールパラジウム触媒
  • Author(s): 魚住泰広，山田陽一
  • Organizer: 日本学術会議 第１１６委員会「第１・第２・第３合同分科会」
  • Place of Presentation: 学士会館（東京都千代田区）
• [Presentation] カップリング反応に有効な高活性・高再利用性自己組織化高分子イミダゾール―パラジウム触媒の創製
  • Author(s): 山田陽一，Shaheen M. Sarkar，魚住泰広
  • Organizer: 有機金属化学討論会
  • Place of Presentation: 大阪大学吹田キャンパス（大阪府吹田市）
• [Presentation] A Self-Assembled Poly(Imidazole-Pallaium) Catalyst for Coupling Reactions
  • Author(s): Y. M. A. Yamada, S. M. Sarkar, Y. Uozumi
  • Organizer: The 2nd RIKEN-McGill University Scientific Workshop
  • Place of Presentation: 理化学研究所（埼玉県和光市）
• [Presentation] A Self-Assembled Poly(Imidazole-Palladium) Catalyst for Coupling Reactions
  • Author(s): Shaheen M. Sarkar, Yoichi M. A. Yamada and Yasuhiro Uozumi
  • Organizer: The Seventh International Forum on Chemistry of Functional Organic Chemicals
  • Place of Presentation: 東京大学（東京都文京区）
• [Presentation] A self-assembled poly(imidazole-copper) catalyst for Huisgen cycloaddition
  • Author(s): Shaheen M. Sarkar, Yoichi M. A. Yamada and Yasuhiro Uozumi
  • Organizer: The 2nd RIKEN-McGill University Scientific Workshop
  • Place of Presentation: 理化学研究所（埼玉県和光市）
• [Presentation] Development of Membranous Polymeric Palladium Nanoparticle Composite-Installed Microflow Reactions and Their Application to the Hydrodehalogenation
  • Author(s): Aya Ohno, Toshihiro Watanabe, Yoichi M. A. Yamada, Yasuhiro Uozumi
  • Organizer: The 2nd RIKEN-McGill University Scientific Workshop
  • Place of Presentation: 理化学研究所（埼玉県和光市）
• [Presentation] Development of a Polymeric Membranous Acid Catalyst-Installed Microreactor
  • Author(s): Maki Minakawa, Yoichi M. A. Yamada and Yasuhiro Uozumi
  • Organizer: The 2nd RIKEN-McGill University Scientific Workshop
  • Place of Presentation: 理化学研究所（埼玉県和光市）
• [Presentation] Development of Membranous Polymeric Palladium Nanoparticle Composite-Installed Microflow Devices and their Application to the Hydrodehalogenation
  • Author(s): Aya Ohno, Toshihiro Watanabe, Yoichi M. A. Yamada, Yasuhiro Uozumi
  • Organizer: The Seventh International Forum on Chemistry of Functional Organic Chemicals
  • Place of Presentation: 東京大学（東京都文京区）
• [Presentation] A Novel Concept to Complete a Classic Equilibrium Acetalization in Water
  • Author(s): Maki Minakawa, Yoichi M. A. Yamada, Yasuhiro Uozumi
  • Organizer: The Seventh International Forum on Chemistry of Functional Organic Chemicals
  • Place of Presentation: 東京大学（東京都文京区）
• [Presentation] 高分子銅触媒膜導入型マイクロデバイスの開発：ヒュスゲン環化付 加への応用
  • Author(s): 大野 綾・山田 陽一・魚住 泰広
  • Organizer: 日本化学会第93春季年会(2013)
  • Place of Presentation: 立命館大学（滋賀県草津市）
• [Presentation] シリコンナノ構造体担持パラジウムナノ粒子触媒の開発
  • Author(s): 佐藤 太久真・湯山 喜也・山田 陽一・藤川 茂紀・魚住 泰広
  • Organizer: 日本化学会第93春季年会(2013)
  • Place of Presentation: 立命館大学（滋賀県草津市）
• [Presentation] "自己組織化高分子イミダゾールパラジウム触媒による鈴木-宮浦反 応と溝呂木-ヘック反応"
  • Author(s): SARKAR, Shaheen・山田 陽一・魚住 泰広
  • Organizer: 日本化学会第93春季年会(2013)
  • Place of Presentation: 立命館大学（滋賀県草津市）
• [Presentation] "フェノール樹脂型スルホン酸触媒を用いたアルコールとカルボン酸 のソルベントフリー条件下における直接的エステル化反応"
  • Author(s): 皆川 真規・白 喜烈・山田 陽一・魚住 泰広
  • Organizer: 日本化学会第93春季年会(2013)
  • Place of Presentation: 立命館大学（滋賀県草津市）
• [Presentation] 山田陽一，Shaheen M. Sarkar，魚住泰広
  • Author(s): Huisgen環化反応に有効な自己組織化高分子イミダゾール銅触媒の開発
  • Organizer: 日本薬学会第133年会(2013)
  • Place of Presentation: パシフィコ横浜（神奈川県横浜市）
• [Book] 「『フロー・マイクロ合成 基礎から実際の合成・製造まで』 第１６章 担持触媒反応 (2014)
  • Author(s): 山田陽一，魚住泰広
  • Publisher: 化学同人
• [Patent(Industrial Property Rights)] HYDROGENATION CATALYST (2012)
  • Inventor(s): Yoichi Yamada et al
  • Industrial Property Rights Holder: McGill University (Canada)
  • Industrial Property Rights Type: 特許
  • Filing Date: 2012-12-24
  • Overseas