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Catalytic conversion of cellulose and chitin using non-polar interactions

Research Project

Project/Area Number 18H01781
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 27030:Catalyst and resource chemical process-related
Research InstitutionHokkaido University

Principal Investigator

KOBAYASHI Hirokazu  北海道大学, 触媒科学研究所, 助教 (30545968)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥16,900,000 (Direct Cost: ¥13,000,000、Indirect Cost: ¥3,900,000)
Fiscal Year 2020: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2019: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2018: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Keywordsバイオマス / セルロース / キチン / 触媒 / 加水分解 / ロンドン分散力 / メカノキャタリシス / CH-π相互作用 / 有機窒素化合物 / 分散力 / キチンオリゴ糖 / N-アセチルグルコサミン
Outline of Final Research Achievements

Cellulose and chitin are abundant and renewable resources, but they are very recalcitrant. To convert the biomass molecules efficiently, we came up with a new idea for preparing catalysts that use interactions working among non-polar groups. This approach achieved the high yielding synthesis of oligosaccharides by the hydrolysis of the biomass in the presence of mechanical forces. Our study shows the synergy between non-polar interactions and weak acid catalysis to achieve the high performance. We have also clarified the reaction mechanism of how mechanical forces work. Specifically, the classical physics simulations and quantum calculations have indicated that compressive forces activate the biomass molecules towards hydrolysis. We have also revealed that the monomer of chitin, N-acetylglucosamine, can be converted to a standard amino acid and a cyclic compound. The latter is a potential monomer for nitrogen-containing polymers.

Academic Significance and Societal Importance of the Research Achievements

これまでの研究では、セルロースやキチンが持つ極性部位との相互作用に着目し、触媒設計や反応系の設計が行われていた。しかし、報告者らは、極性を持たない部位の相互作用も重要であると考え、それを取り入れることによって、高選択的な分解反応を達成した。さらに、その反応機構を明らかにし、今後の触媒開発指針へとつなげた。生成したオリゴ糖は免疫力を高めることが提案されており、様々な用途展開が期待される。また、これらオリゴ糖の分解は容易であるため、単糖に変換したのち、様々な化学品への誘導が期待できる。特に、キチンを原料に用いることによって、バイオマス由来の含窒素化合物も合成も可能となる。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (32 results)

All 2021 2020 2019 2018 Other

All Journal Article (8 results) (of which Peer Reviewed: 6 results) Presentation (22 results) (of which Int'l Joint Research: 6 results,  Invited: 6 results) Remarks (2 results)

  • [Journal Article] On the Electronic Structure Origin of Mechanochemically Induced Selectivity in Acid-Catalyzed Chitin Hydrolysis2021

    • Author(s)
      Danjo De Chavez, Hirokazu Kobayashi, Atsushi Fukuoka, Jun-ya Hasegawa
    • Journal Title

      J. Phys. Chem. A

      Volume: 125 Issue: 1 Pages: 187-197

    • DOI

      10.1021/acs.jpca.0c09030

    • NAID

      120007184598

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Amorphization and Semi-Dry Conversion of Crystalline Cellulose to Oligosaccharides by Impregnated Phosphoric Acid2020

    • Author(s)
      Jun Hirayama, Hirokazu Kobayashi, Atsushi Fukuoka
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 93 Issue: 2 Pages: 273-278

    • DOI

      10.1246/bcsj.20190287

    • NAID

      130007798337

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile Preparation of 3-Acetamido-5-acetylfuran from N-Acetyl-D-glucosamine by using Commercially Available Aluminum Salts2020

    • Author(s)
      Daniele Padovan, Hirokazu Kobayashi, Atsushi Fukuoka
    • Journal Title

      ChemSusChem

      Volume: 13 Issue: 14 Pages: 3594-3598

    • DOI

      10.1002/cssc.202001068

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effect of Lewis acid on catalytic dehydration of a chitin-derived sugar alcohol2020

    • Author(s)
      Takuya Sagawa, Hirokazu Kobayashi, Atsushi Fukuoka
    • Journal Title

      Mol. Catal.

      Volume: 498 Pages: 111282-111282

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hydrolysis of cellulose by carbon catalysts with weak acid sites2019

    • Author(s)
      小林広和, 福岡淳
    • Journal Title

      TANSO

      Volume: 2019 Issue: 290 Pages: 211-218

    • DOI

      10.7209/tanso.2019.211

    • NAID

      130007761409

    • ISSN
      0371-5345, 1884-5495
    • Year and Date
      2019-11-15
    • Related Report
      2019 Annual Research Report
  • [Journal Article] Catalytic Conversion of a Chitin-Derived Sugar Alcohol to an Amide-Containing Isosorbide Analog2019

    • Author(s)
      Sagawa Takuya、Kobayashi Hirokazu、Murata Chinatsu、Shichibu Yukatsu、Konishi Katsuaki、Fukuoka Atsushi
    • Journal Title

      ACS Sustainable Chemistry & Engineering

      Volume: 7 Issue: 17 Pages: 14883-14888

    • DOI

      10.1021/acssuschemeng.9b02985

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conversion of N-Acetylglucosamine to Protected Amino Acid over Ru/C Catalyst2018

    • Author(s)
      K. Techikawara, H. Kobayashi, A. Fukuoka
    • Journal Title

      ACS Sustainable Chem. Eng.

      Volume: 6 Issue: 9 Pages: 12411-12418

    • DOI

      10.1021/acssuschemeng.8b02951

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 固体触媒を用いたセルロース・キチンからの化学品合成2018

    • Author(s)
      小林広和
    • Journal Title

      触媒

      Volume: 60 Pages: 226-226

    • Related Report
      2018 Annual Research Report
  • [Presentation] 弱酸点を持つ炭素触媒によるキチンの機械的加水分解反応2020

    • Author(s)
      鈴木悠介, 佐川拓矢, 小林広和, 福岡淳
    • Organizer
      化学系協会北海道支部2020年冬季研究発表会
    • Related Report
      2020 Annual Research Report
  • [Presentation] キチン由来糖アルコールの脱水縮合におけるルイス酸添加効果2020

    • Author(s)
      佐川拓矢, 小林広和, 福岡淳
    • Organizer
      日本化学会第100回春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 触媒法によるキチンの解重合と含窒素化合物合成2020

    • Author(s)
      小林広和
    • Organizer
      第126回触媒討論会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 弱酸点を持つ炭素触媒によるキチンの機械的加水分解2020

    • Author(s)
      鈴木悠介, 佐川拓矢, 小林広和, 福岡淳
    • Organizer
      第126回触媒討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] キチン由来糖アルコールの脱水反応における亜リン酸の触媒作用2020

    • Author(s)
      楊程, 佐川拓矢, 小林広和, 福岡淳
    • Organizer
      第126回触媒討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Facile conversion of N-acetylglucosamine into 3-acetamido-5-acetylfuran by AlCl3 catalyst2020

    • Author(s)
      Daniele Padovan, Hirokazu Kobayashi, Atsushi Fukuoka
    • Organizer
      第126回触媒討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ルイス酸添加によるキチン由来アミノ糖アルコールの触媒的脱水反応の促進2020

    • Author(s)
      佐川拓矢, 小林広和, 福岡淳
    • Organizer
      第126回触媒討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 酸触媒による含窒素糖アルコールの脱水反応におけるルイス酸添加効果2020

    • Author(s)
      佐川拓矢, 小林広和, 福岡淳
    • Organizer
      第125回触媒討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 触媒法によるバイオマスからの再生可能化学品の合成2020

    • Author(s)
      小林広和, 福岡淳
    • Organizer
      第6回北大・部局横断シンポジウム
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 触媒によるセルロース・キチンの解重合と生成物利用2020

    • Author(s)
      小林広和
    • Organizer
      産業技術総合研究所第7回食・触コンソーシアムワークショップ
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 触媒法によるキチンの解重合と含窒素化合物合成2020

    • Author(s)
      小林広和
    • Organizer
      触媒学会・触媒工業協会交流サロン
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] Dehydration condensation of chitin-derived sugar alcohol by acid catalyst2019

    • Author(s)
      Takuya Sagawa, Hirokazu Kobayashi, Atsushi Fukuoka
    • Organizer
      The 17th Korea-Japan Symposium on Catalysis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Catalytic Conversion of Cellulose and Chitin to Chemicals2019

    • Author(s)
      Atsushi Fukuoka, Abhijit Shrotri, Hirokazu Kobayashi
    • Organizer
      The 26th Meeting of the North American Catalysis Society
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Catalytic conversion of chitin into amino acid2019

    • Author(s)
      Atsushi Fukuoka, Hirokazu Kobayashi
    • Organizer
      14th EuropaCat
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 酸触媒による含窒素糖アルコールの脱水縮合反応2019

    • Author(s)
      佐川拓矢, 小林広和, 福岡淳
    • Organizer
      第124回触媒討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] キチン由来糖アルコールの触媒的変換反応2019

    • Author(s)
      佐川拓矢, 小林広和, 福岡淳
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 触媒によるキチンの加水分解と含窒素化合物合成2019

    • Author(s)
      小林広和, 鉄地河原浩太, 藪下瑞帆, 福岡淳
    • Organizer
      第123回触媒討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Catalysis of weakly acidic carbons for hydrolysis of cellulose2018

    • Author(s)
      Hirokazu Kobayashi, Atsushi Fukuoka
    • Organizer
      TOCAT8
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Adsorption and Depolymerization of Cellulose-Derived Long-Chain Beta-Glucans by Post-Synthetically Functionalized Zeolite-Templated Carbon Catalysts2018

    • Author(s)
      Mizuho Yabushita, Kota Techikawara, Hirokazu Kobayashi, Atsushi Fukuoka, Alexander Katz
    • Organizer
      TOCAT8
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] C-C結合切断と酸化によるN-アセチルグルコサミンからのアミノ酸合成2018

    • Author(s)
      鉄地河原浩太, 小林広和, 福岡淳
    • Organizer
      第122回触媒討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 触媒による非可食バイオマスの選択的分解2018

    • Author(s)
      小林広和, 福岡淳
    • Organizer
      東北大学多元物質科学研究所高分子・ハイブリッド材料研究センター若手フォーラム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Catalytic Conversion of Chitin to Chemicals2018

    • Author(s)
      Hirokazu Kobayashi, Atsushi Fukuoka
    • Organizer
      The 14th Hokkaido University-Nanjing University-NIMS/MANA Joint Symposium
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Remarks] Researchmap

    • URL

      https://researchmap.jp/read0148875/

    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
  • [Remarks] Researchmap

    • URL

      https://researchmap.jp/read0148875

    • Related Report
      2018 Annual Research Report

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Published: 2018-04-23   Modified: 2022-01-27  

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