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Development of selective conversion of chitin derivatives

Research Project

Project/Area Number 19K15608
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 34030:Green sustainable chemistry and environmental chemistry-related
Research InstitutionTokyo University of Science (2020-2022)
Hokkaido University (2019)

Principal Investigator

Sagawa Takuya  東京理科大学, 工学部工業化学科, 助教 (90829582)

Project Period (FY) 2019-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2022: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2021: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2020: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsキチン / 糖アルコール / 触媒 / 含窒素有機化合物 / 酸・塩基反応 / アミノアルコール / ポリウレタン / 脱水縮合 / 炭酸エステル / アミノ酸 / ルイス酸 / バイオマス
Outline of Research at the Start

キチンは窒素原子を含むアミノ糖の高分子であり、含窒素有機化合物の原料としての利用が期待される。しかし、キチンを出発物質とした有用化学品への効率的な変換は達成されていない。そこで、本研究ではアミノ糖を水素還元することによって得られる糖アルコールを出発物質とした有用化学品の合成経路の開発を行う。具体的には、医薬品、高分子の原料となるアミノ酸やアミノアルコールを合成する経路を提案し、含窒素有機化合物の選択的な変換反応の開拓とその反応性制御を目指す。

Outline of Final Research Achievements

Herein, we developed the synthesis route for beneficial chemicals using sugar alcohols obtained by hydrogenation of chitin-derived sugars as a starting material. We succeeded in synthesizing organonitrogen compounds as follows: (1) an amino alcohol, which has rigid carbon skeleton, by dehydration condensation, and (2) oxazolidinone derivatives, which are used as a raw material for pharmaceuticals, by esterification and cyclization reactions. In particular, the amino alcohol is an attractive compound because it can be derived into a nitrogen-containing polymer having excellent strength and heat resistance. Furthermore, the conversion of this amino alcohol to a raw material of polyurethane was achieved.

Academic Significance and Societal Importance of the Research Achievements

キチンは窒素原子を含む糖の高分子であり、含窒素有機化合物の原料としての利用が期待される。しかし、糖の化学的な不安定さが原因で、キチンを出発物質とした有用化学品への効率的な変換は達成されていない。本研究では糖を水素還元することで得られる糖アルコールを出発物質として有用化合物の合成を行った。糖アルコールからアミノアルコール、オキサゾリジノンを、糖の抱える不安定性の問題を回避した経路での合成に成功し、キチンから様々な有用化学品への誘導体化の可能性が示された。

Report

(5 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • 2020 Research-status Report
  • 2019 Research-status Report
  • Research Products

    (20 results)

All 2023 2022 2021 2020 2019

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Open Access: 1 results) Presentation (16 results) (of which Int'l Joint Research: 7 results)

  • [Journal Article] Catalytic Synthesis of Oxazolidinones from a Chitin-Derived Sugar Alcohol2022

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

      Bulletin of the Chemical Society of Japan

      Volume: 95 Issue: 7 Pages: 1054-1059

    • DOI

      10.1246/bcsj.20220106

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Synthesis of Oligosaccharides by Mechanochemical Hydrolysis of Chitin over a Carbon‐Based Catalyst2022

    • Author(s)
      Kobayashi Hirokazu、Suzuki Yusuke、Sagawa Takuya、Saito Makoto、Fukuoka Atsushi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 3

    • DOI

      10.1002/anie.202214229

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Effect of Lewis acid on catalytic dehydration of a chitin-derived sugar alcohol2020

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

      Molecular Catalysis

      Volume: 498 Pages: 111282-111282

    • DOI

      10.1016/j.mcat.2020.111282

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [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 Research-status Report
    • Peer Reviewed
  • [Presentation] 固体酸触媒を用いたキチン由来糖アルコールの脱水縮合反応2023

    • Author(s)
      杉山 拓生,佐川 拓矢,橋詰 峰雄
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Synthesis of Oxazolidinone Compounds from Sugar Alcohol Derived from Chitin2022

    • Author(s)
      Takuya SAGAWA, Hirokazu KOBAYASHI, Mineo HASHIZUME, Atsushi FUKUOKA
    • Organizer
      The 9th Tokyo Conference on Advanced Catalytic Science and Technology (TOCAT9)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] キチン由来糖アルコールを原料としたバイオベースプラスチックモノマーの触媒的合成2022

    • Author(s)
      佐川 拓矢,池田 新,橋詰 峰雄
    • Organizer
      第130回触媒討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] キチン誘導体の触媒的カルボニル化に対する反応条件の検討2022

    • Author(s)
      伊藤 秀真,佐川 拓矢,橋詰 峰雄
    • Organizer
      第12回CSJ化学フェスタ2022
    • Related Report
      2022 Annual Research Report
  • [Presentation] Synthesis of oxazolidinone compounds from sugar alcohol derived from chitin2022

    • Author(s)
      Takuya Sagawa,Hirokazu Kobayashi, Mineo Hashizume, Atsushi Fukuoka
    • Organizer
      The 9th Tokyo Conference on Advanced Catalytic Science and Technology (TOCAT9)
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] キチン由来糖アルコールからオキサゾリジノン誘導体の選択合成2021

    • Author(s)
      佐川 拓矢,小林 広和,福岡 淳,橋詰 峰雄
    • Organizer
      第128回触媒討論会
    • Related Report
      2021 Research-status Report 2020 Research-status Report
  • [Presentation] キチン由来糖アルコール誘導体の塩基触媒による炭酸エステル化2021

    • Author(s)
      池田 新,佐川 拓矢,橋詰 峰雄
    • Organizer
      第128回触媒討論会
    • Related Report
      2021 Research-status Report 2020 Research-status Report
  • [Presentation] Acid-Catalyzed dehydration of sugar alcohol derived from chitin2021

    • Author(s)
      Takuya Sagawa, Hirokazu Kobayashi, Atsushi Fukuoka
    • Organizer
      1-st Japan-China Symposium on Catalysis
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] Acid-catalyzed dehydration condensation of amino sugar alcohol derived from chitin2021

    • Author(s)
      Takuya Sagawa, Hirokazu Kobayashi, Atsushi Fukuoka
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2021 (Pacifichem 2021)
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] Acid-catalyzed dehydration of a sugar alcohol derived from chitin2021

    • Author(s)
      Takuya Sagawa, Hirokazu Kobayashi, Atsushi Fukuoka
    • Organizer
      1st Japan-China Symposium on Catalysis
    • Related Report
      2020 Research-status Report
    • Int'l Joint Research
  • [Presentation] Acid-catalyzed dehydration condensation of amino sugar alcohol derived from chitin2021

    • Author(s)
      Takuya Sagawa, Hirokazu Kobayashi, Atsushi Fukuoka
    • Organizer
      Paciffichem2021
    • Related Report
      2020 Research-status Report
    • Int'l Joint Research
  • [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 Research-status Report
  • [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 Research-status 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 Research-status 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2019

    • Author(s)
      佐川拓矢, 小林広和, 福岡淳
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status 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2019

    • Author(s)
      佐川拓矢, 小林広和, 福岡淳
    • Organizer
      第125回触媒討論会
    • Related Report
      2019 Research-status Report

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Published: 2019-04-18   Modified: 2024-01-30  

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