Research network among materials science and theoretical chemistry for the development of novel heterogeneous catalysts for biomass valorization

• Project/Area Number: 18KK0135
• Research Category: Fund for the Promotion of Joint International Research (Fostering Joint International Research (B))
• Allocation Type: Multi-year Fund
• Review Section: Medium-sized Section 27:Chemical engineering and related fields
• Research Institution: Hokkaido University
• Principal Investigator: Nakajima Kiyotaka 北海道大学, 触媒科学研究所, 准教授 (90451997)
• Co-Investigator(Kenkyū-buntansha): 大友 亮一 北海道大学, 地球環境科学研究院, 准教授 (10776462) ; 谷口 博基 名古屋大学, 理学研究科, 准教授 (80422525)
• Project Period (FY): 2018-10-09 – 2021-03-31
• Project Status: Completed (Fiscal Year 2020)
• Budget Amount: ¥17,940,000 (Direct Cost: ¥13,800,000、Indirect Cost: ¥4,140,000); Fiscal Year 2020: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2019: ¥8,450,000 (Direct Cost: ¥6,500,000、Indirect Cost: ¥1,950,000); Fiscal Year 2018: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
• Keywords: バイオマス変換 / 再生可能な炭素資源 / 二酸化炭素削減 / バイオマスポリマー / 固体触媒 / バイオマス / 酸塩基 / 酸化還元 / 機能性酸化物

Outline of Final Research Achievements

We have developed a new reaction system for the production of furan dicarboxylic acid and its alkyl esters from glucose using heterogeneous catalysts. The combination of materials science and catalytic chemistry will enable the design of new catalytic materials and catalytic reactions, while theoretical calculations for clarifying reaction dynamics with catalytic active site and substrate/intermediates will support experimental results to be well-understood at the molecular level. Acetal protection strategy will control side reactions and contribute predominantly to the selective production of target furan compounds in concentrated solutions. The technologies developed in this research can be beneficial for the industrial implementation of the furan compounds in the production of biobased polymers.

Academic Significance and Societal Importance of the Research Achievements

世界的な競争が激化する現在でも，フランジカルボン酸の大量合成を可能にする技術開発は開発されていなかった．我々の“アセタール保護を利用した酸化・酸化的エステル化反応”は環境負荷および生産性の観点から非常に優れた技術であり，実用プロセス設計の基盤となる．踏み込んだコスト削減やプロセスの簡略化など更なる研究は必要となるが，化石資源由来のテレフタル酸を基盤とした芳香族ポリマーを再生可能な炭素資源であるバイオマス由来品に代替する基盤技術の確立が加速すると考えている．

Research Products

• [Int'l Joint Research] Eindhoven University of Technology(オランダ)
• [Int'l Joint Research] Eindhoven University of Technology(オランダ)
• [Int'l Joint Research] Schuit Institute of Catalysis/Department of Chem. Eng. & Chemistry/Eindhoven University of Technology(オランダ)
• [Journal Article] Ni2P Nanoalloy as an Air-Stable and Versatile Hydrogenation Catalyst in Water: P-Alloying Strategy for Designing Smart Catalysts (2021)
  • Author(s): Fujita Shu、Yamaguchi Sho、Yamasaki Jun、Nakajima Kiyotaka、Yamazoe Seiji、Mizugaki Tomoo、Mitsudome Takato
  • Journal Title: Chemistry European Journal Volume: 27 Issue: 13 Pages: 4439-4446
  • DOI: 10.1002/chem.202005037
  • Peer Reviewed / Open Access
• [Journal Article] Air-Stable and Reusable Cobalt Phosphide Nanoalloy Catalyst for Selective Hydrogenation of Furfural Derivatives (2021)
  • Author(s): Ishikawa Hiroya、Sheng Min、Nakata Ayako、Nakajima Kiyotaka、Yamazoe Seiji、Yamasaki Jun、Yamaguchi Sho、Mizugaki Tomoo、Mitsudome Takato
  • Journal Title: ACS Catalysis Volume: 11 Issue: 2 Pages: 750-757
  • DOI: 10.1021/acscatal.0c03300
  • NAID: 120006952198
  • Peer Reviewed / Open Access
• [Journal Article] Air-stable and reusable nickel phosphide nanoparticle catalyst for the highly selective hydrogenation of d-glucose to d-sorbitol (2021)
  • Author(s): Yamaguchi Sho、Fujita Shu、Nakajima Kiyotaka、Yamazoe Seiji、Yamasaki Jun、Mizugaki Tomoo、Mitsudome Takato
  • Journal Title: Green Chemistry Volume: 23 Issue: 5 Pages: 2010-2016
  • DOI: 10.1039/d0gc03301d
  • Peer Reviewed / Open Access
• [Journal Article] Nano vs. bulk rutile TiO2:N,F in Z-scheme overall water splitting under visible light (2020)
  • Author(s): Akinobu Miyoshi, Kosaku Kato, Toshiyuki Yokoi, Jan J. Wiesfeld, Kiyotaka Nakajima, Akira Yamakata and Kazuhiko Maeda
  • Journal Title: Journal of Materials Chemistry A Volume: 8 Issue: 24 Pages: 11996-12002
  • DOI: 10.1039/d0ta04450d
  • Peer Reviewed
• [Journal Article] Water-Resistant Pt Sites in Hydrophobic Mesopores Effective for Low-Temperature Ethylene Oxidation (2020)
  • Author(s): Satter Shazia S.、Hirayama Jun、Kobayashi Hirokazu、Nakajima Kiyotaka、Fukuoka Atsushi
  • Journal Title: ACS Catalysis Volume: 10 Issue: 22 Pages: 13257-13268
  • DOI: 10.1021/acscatal.0c02816
  • NAID: 120007171681
  • Peer Reviewed
• [Journal Article] Controllable Factors of Supported Ir Complex Catalysis for Aromatic C?H Borylation (2020)
  • Author(s): Maeda Kyogo、Uemura Yohei、Chun Wang-Jae、Satter Shazia Sharmin、Nakajima Kiyotaka、Manaka Yuichi、Motokura Ken
  • Journal Title: ACS Catalysis Volume: 10 Issue: 24 Pages: 14552-14559
  • DOI: 10.1021/acscatal.0c03734
  • Peer Reviewed
• [Journal Article] Catalytic Conversion of Lignocellulosic Biomass:Application of Heterogeneous and Homogeneous Catalysts to Process Biomass into Value-Added Compounds (2020)
  • Author(s): Wiesfeld Jan J.、Hensen Emiel J. M.、Nakajima Kiyotaka
  • Journal Title: Advanced Heterogeneous Catalysts Volume 1: Applications at the Nano-Scale Volume: Chapter 5 Pages: 151-182
  • DOI: 10.1021/bk-2020-1359.ch005
  • ISBN: 9780841298804, 9780841298798
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Selective hydrogenation of 5-hydroxymethylfurfural and its acetal with 1,3-propanediol to 2,5-bis(hydroxymethyl)furan using supported rhenium-promoted nickel catalysts in water (2020)
  • Author(s): Wiesfeld, Jan J.; Kim, Minjune; Nakajima, Kiyotaka; Hensen, Emiel J. M.
  • Journal Title: Green Chemistry Volume: 22 Issue: 4 Pages: 1229-1238
  • DOI: 10.1039/c9gc03856f
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Unique Catalysis of Nickel Phosphide Nanoparticles to Promote the Selective Transformation of Biofuranic Aldehydes into Diketones in Water (2020)
  • Author(s): Fujita, Shu; Nakajima, Kiyotaka; Yamasaki, Jun; Mizugaki, Tomoo; Jitsukawa, Koichiro; Mitsudome, Takato
  • Journal Title: ACS Catalysis Volume: 10 Issue: 7 Pages: 4261-4267
  • DOI: 10.1021/acscatal.9b05120
  • Peer Reviewed / Open Access
• [Journal Article] Effective strategy of furan dicarboxylate production for biobased polyester applications (2019)
  • Author(s): Minjune Kim, Yaqiong Su, Atsushi Fukuoka, Takayuki Aoshima, Emiel J. M. Hensen, Kiyotaka Nakajima
  • Journal Title: ACS Catalysis Volume: 9 Issue: 5 Pages: 4277-4285
  • DOI: 10.1021/acscatal.9b00450
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Influence of a Co-immobilized Tertiary Amine on the Structure and Reactivity of a Rh Complex: Accelerating Effect on Heterogeneous Hydrosilylation (2019)
  • Author(s): Maeda Kyogo, Uemura Yohei, Kim Minjune, Nakajima Kiyotaka, Tanaka Shinji, Chun Wang-Jae, Motokura Ken
  • Journal Title: The Journal of Physical Chemistry C Volume: 123 Issue: 23 Pages: 14556-14563
  • DOI: 10.1021/acs.jpcc.9b03280
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Lewis Acid and Base Catalysis of YNbO4 Toward Aqueous‐Phase Conversion of Hexose and Triose Sugars to Lactic Acid in Water (2019)
  • Author(s): Kim Minjune, Ronchetti Silvia, Onida Barbara, Ichikuni Nobuyuki, Fukuoka Atsushi, Kato Hideki, Nakajima Kiyotaka
  • Journal Title: ChemCatChem Volume: 12 Issue: 1 Pages: 350-359
  • DOI: 10.1002/cctc.201901435
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Synthesis of 5-hydroxymethylfurfural from highly concentrated aqueous fructose solutions using activated carbon (2019)
  • Author(s): Nishimura, Yuichi; Suda, Manato; Kuroha, Mai; Kobayashi, Hirokazu; Nakajima, Kiyotaka; Fukuoka, Atsushi
  • Journal Title: Carbohydrate Research Volume: 486 Pages: 107826-107826
  • DOI: 10.1016/j.carres.2019.107826
  • Peer Reviewed
• [Journal Article] 触媒法バイオマス変換による基幹化学品合成 (2019)
  • Author(s): 佐川拓矢, 中島清隆, 福岡淳
  • Journal Title: 触媒 Volume: 61 Pages: 182-188
  • Peer Reviewed
• [Journal Article] Selective Glucose-to-Fructose Isomerization in Ethanol Catalyzed by Hydrotalcites (2019)
  • Author(s): Mizuho Yabushita, Natsumi Shibayama, Kiyotaka Nakajima, Atsushi Fukuoka
  • Journal Title: ACS Catalysis Volume: 9 Issue: 3 Pages: 2101-2109
  • DOI: 10.1021/acscatal.8b05145
  • Peer Reviewed
• [Presentation] 低温におけるルテニウム担持触媒を用いたエチレン酸化 (2021)
  • Author(s): 長内有輝, 中島清隆, 福岡淳
  • Organizer: 化学系学協会北海道支部2021年冬季研究発表会
• [Presentation] 担持金属触媒によるエチレンの低温酸化 (2021)
  • Author(s): 八鍬秀, 中島清隆, 福岡淳
  • Organizer: 化学系学協会北海道支部2021年冬季研究発表会
• [Presentation] 担持ルテニウム触媒を利用したバイオマス由来アセタールの水素化反応 (2020)
  • Author(s): 遠藤幸一朗, 中島清隆, 福岡淳
  • Organizer: 第126回触媒討論会
• [Presentation] Selective oxidation of 5-hydroxymethylfurfural-acetal to 2,5-diformylfuran in concentrated solutions (2020)
  • Author(s): T. Boonyakarn, J. Wiesfeld, K. Nakajima, A. Fukuoka
  • Organizer: 第126回触媒討論会
• [Presentation] Selective Production of Biobased 5-Formylfuran-2-carboxylic Acid in High Concentration (2020)
  • Author(s): J. Wiesfeld, M. Asakawa, A. Fukuoka, E. J. M. Hensen, K. Nakajima
  • Organizer: 第126回触媒討論会
• [Presentation] 金属酸化物の固体酸塩基触媒作用～バイオマス変換を例にして～ (2019)
  • Author(s): 中島清隆
  • Organizer: 第13回触媒道場
  • Invited
• [Presentation] A new strategy for Chemocatalytic Production of Biomass-derived Carbohydrates and Diols (2019)
  • Author(s): Kiyotaka Nakajima
  • Organizer: 108th MSL Lecture (Japan-Taiwan Joint Mini-Workshop on Catalysis)
  • Int'l Joint Research / Invited
• [Presentation] Direct Conversion of Glucose to Erythrose and Glycol Aldehyde in Ethanol by Selective Retro-aldolization (2019)
  • Author(s): Natsumi Shibayama, Mizuho Yabushita, Kiyotaka Nakajima, Atsushi Fukuoka
  • Organizer: 14th EuropaCat - European Congress on Catalysis
  • Int'l Joint Research
• [Presentation] New Strategy for Selective Production of FDCA from Concentrated HMF-acetal Solutions with CeO2-Supported Au Catalyst (2019)
  • Author(s): Kiyotaka Nakajima, Minjune Kim, Yaqiong Su, Atsushi Fukuoka, Emiel J.M. Hensen
  • Organizer: 14th EuropaCat - European Congress on Catalysis
  • Int'l Joint Research
• [Presentation] An efficient strategy for practical furan dicarboxylate production for biobased polymer applications (2019)
  • Author(s): Minjune Kim, Yaqiong Su, Takayuki Aoshima, Atsushi Fukuoka, Emiel J. M. Hensen, Kiyotaka Nakajima
  • Organizer: 14th EuropaCat - European Congress on Catalysis
  • Int'l Joint Research
• [Presentation] ハイドロキシアパタイト担持金属触媒を用いた選択的5-ホルミル-2-フランカルボン酸(FFCA)合成 (2019)
  • Author(s): 淺川みゆき, K. Minjune, 中島清隆, 福岡淳
  • Organizer: 第124回触媒討論会
• [Presentation] アセタール化を利用したグルコースの逆アルドール反応によるエリスロース誘導体合成 (2019)
  • Author(s): 柴山夏実, 藪下瑞帆, 中島清隆, 福岡淳
  • Organizer: 第124回触媒討論会
• [Presentation] 逐次的な逆アルドール反応・アセタール化によるグルコースからエリスロースとグリコールアルデヒド誘導体の選択合成 (2019)
  • Author(s): 柴山夏実, 藪下瑞帆, 中島清隆, 福岡淳
  • Organizer: 化学系協会北海道支部2020年冬季研究発表会
• [Presentation] ヒドロキシアパタイト担持金属触媒を用いた選択的5-ホルミル-2-フランカルボン酸(FFCA)合成 (2019)
  • Author(s): 淺川みゆき, 中島清隆, 福岡淳
  • Organizer: 化学系協会北海道支部2020年冬季研究発表会
• [Presentation] 担持金属触媒を利用したグリコールアルデヒドジエチルアセタールの水素化反応 (2019)
  • Author(s): 遠藤幸一朗, 中島清隆, 福岡淳
  • Organizer: 化学系協会北海道支部2020年冬季研究発表会
• [Presentation] Glucose conversion to erythrose and glycolaldehyde diethylacetals by selective retro-aldolization and subsequent acetalization (Poster) (2019)
  • Author(s): 柴山夏実, 藪下瑞帆, 中島清隆, 福岡淳
  • Organizer: 統合物質創製化学研究推進機構第5回国内シンポジウム
  • Int'l Joint Research
• [Presentation] New Strategy for Selective Production of Furan 2,5-dicarboxylic Acid from Concentrated HMF Solutions with CeO2-supported Au Catalyst (2019)
  • Author(s): Kiyotaka Nakajima
  • Organizer: ICAT-Cardiff Catalysis Institute Joint International Symposium on Catalysis, Cardiff, UK
  • Int'l Joint Research / Invited
• [Presentation] Smart HMF conversion to FDCA and its carboxylates with supported Au catalyst (2019)
  • Author(s): Kiyotaka Nakajima
  • Organizer: International Symposium on Heterogeneous Catalysis for Sustainable Energy and Chemical Production, Sapporo, Japan
  • Int'l Joint Research / Invited
• [Presentation] A new strategy for the production of furan dicarboxylic acid with ceria-supported gold nanoparticles (2018)
  • Author(s): Kiyotaka Nakajima
  • Organizer: Department seminar, Department of Chemical and Biomolecular Engineering, Faculty of Engineering, National University of Singapore
  • Int'l Joint Research / Invited
• [Presentation] A New Route for the Formation of FDCA from a Cyclic HMF-Acetal with a Supported Au Catalyst (2018)
  • Author(s): Kiyotaka Nakajima, Minjune Kim, Yaqiong Su, Atsushi Fukuoka, Emiel J.M. Hensen
  • Organizer: 7th Asia-Oceania Conference on Green and Sustainable Chemistry, Singapore
  • Int'l Joint Research
• [Presentation] Isomerization of glucose to fructose by solid base catalysts (2018)
  • Author(s): Natsumi Shibayama, Mizuho Yabushita, Kiyotaka Nakajima, Atsushi Fukuoka
  • Organizer: 7th Asia-Oceania Conference on Green and Sustainable Chemistry, Singapore
  • Int'l Joint Research
• [Presentation] A New Route for the Formation of Furan 2,5-Dicarboxylic Acid from a Cyclic HMF-Acetal (2018)
  • Author(s): Minjune Kim, Yaqiong Su, Atsushi Fukuoka, Emiel J.M. Hensen, Kiyotaka Nakajima
  • Organizer: International Symposium on Catalysis ad Fine Chemicals 2018, Bangkok, Thailand
  • Int'l Joint Research