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One-pot conversion of glutamic acid to 2-pyrrolidone over solid catalysts

Research Project

Project/Area Number 18K14261
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 InstitutionTottori University

Principal Investigator

SUGANUMA Satoshi  鳥取大学, 工学研究科, 准教授 (90731753)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2020: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2019: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2018: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsアミノ酸 / 水素化 / 貴金属触媒 / バイオマス / 脱カルボニル / グルタミン酸 / プロリン / 2-ピロリドン / ルテニウム / ゼオライト / 担持Ru触媒 / 2-ピロリドン / 水素化反応 / ワンポット合成
Outline of Final Research Achievements

Glutamic acid, an abundant nonessential amino acid, was converted into 2-pyrrolidone in the presence of a supported Ru catalyst under a pressurized hydrogen atmosphere. This reaction pathway proceeded through the dehydration of glutamic acid into pyroglutamic acid, subsequent hydrogenation, and the dehydrogenation-decarbonylation of pyroglutaminol into 2-pyrrolidone. In the conversion of pyroglutaminol, Ru/Al2O3 exhibited notably higher activity than supported Pt, Pd, and Rh catalysts. IR analysis revealed that Ru can hydrogenate the formed CO through dehydrogenation-decarbonylation of hydroxymethyl groups in pyroglutaminol and can also easily desorb CH4 from the active sites on Ru. Furthermore, Ru/Al2O3 showed the highest catalytic activity among the tested catalysts in the conversion of pyroglutamic acid. Consequently, the conversion of glutamic acid produced a high yield of 2-pyrrolidone by using the supported Ru catalyst.

Academic Significance and Societal Importance of the Research Achievements

日本の発酵法によるアミノ酸の製造技術は世界トップレベルである.その技術により将来的にバイオマス資源からアミノ酸が安定して供給可能と見込まれる.よって,アミノ酸をサスティナブル化学品原料として利用する技術が構築されれば資源循環の実現に繋がる.本技術ではカルボニルを活性化する触媒を開発した.今後はさらに別のアミノ酸へ展開して,カルボン酸やアミノ基を水素化,脱炭酸,脱アミノ化させる反応を発展させていくことが望まれる.

Report

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

    (16 results)

All 2020 2019 2018

All Journal Article (3 results) (of which Peer Reviewed: 3 results) Presentation (11 results) (of which Int'l Joint Research: 2 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Reactivity of Methane and Benzene over Metal/MFI Zeolite Analyzed with Temperature‐Programmed Reaction Technique2020

    • Author(s)
      Nakamura Koshiro、Okumura Kazu、Tsuji Etsushi、Suganuma Satoshi、Katada Naonobu
    • Journal Title

      ChemCatChem

      Volume: 12 Issue: 8 Pages: 2333-2340

    • DOI

      10.1002/cctc.202000030

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Selective Formation of Active Cobalt Species for Direct Methylation of Benzene with Methane on MFI Zeolite by Co-presence of Secondary Elements2019

    • Author(s)
      Hitoshi Matsubara, Etsushi Tsuji, Yasumi Moriwaki, Kazu Okumura, Kana Yamamoto, Koshiro Nakamura, Satoshi Suganuma and Naonobu Katada
    • Journal Title

      Catalysis Letters

      Volume: 149 Issue: 9 Pages: 2627-2635

    • DOI

      10.1007/s10562-019-02855-y

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] One‐Step Conversion of Glutamic Acid into 2‐Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation2019

    • Author(s)
      Satoshi Suganuma, Akihiro Otani, Shota Joka, Hiroki Asako, Rika Takagi, Etsushi Tsuji, Naonobu Katada
    • Journal Title

      ChemSusChem

      Volume: 12 Issue: 7 Pages: 1381-1389

    • DOI

      10.1002/cssc.201802980

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] 貴金属系複合触媒によるプロリンの水素化2020

    • Author(s)
      加来知奈実, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第50回石油・石油化学討論会 熊本大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 貴金属-モリブデン複合触媒によるプロリンの水素化2020

    • Author(s)
      加来知奈実, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第126回触媒討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ピログルタミン酸変換反応に対する担持Ruの触媒作用への担体の影響2019

    • Author(s)
      大谷明央, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第35回ゼオライト研究発表会
    • Related Report
      2019 Research-status Report
  • [Presentation] Ru/MFIゼオライトを触媒とするピログルタミン酸から2-ピロリドンの選択的合成2019

    • Author(s)
      大谷明央, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第49回石油・石油化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] Synthesis of 2-Pyrrolidone from Glutamic Acid on Ru Catalyst2019

    • Author(s)
      Satoshi Suganuma, Akio Otani, Shota Joka, Etsushi Tsuji and Naonobu Katada
    • Organizer
      EuropaCat2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] High Selectivity of 2-Pyrrolidone from Pyroglutamic Acid over Ru Loaded on MFI Zeolite2019

    • Author(s)
      Akihiro Otani, Satoshi Suganuma, Etsushi Tsuji and Naonobu Katada
    • Organizer
      IZC'19
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Hydrogenation of Pyroglutamic Acid into Pyroglutaminol over Co-modified Ru Catalyst2019

    • Author(s)
      金田玲奈, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第10回触媒科学研究発表会
    • Related Report
      2019 Research-status Report
  • [Presentation] グルタミン酸から2-ピロリドンの合成過程におけるピログルタミノール変換に活性なRuの機能2018

    • Author(s)
      菅沼学史, 上加政太, 大谷明央, 辻悦司, 片田直伸
    • Organizer
      第122回触媒討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ピログルタミン酸から2-ピロリドンの合成に対するRu触媒の担体が活性に与える影響2018

    • Author(s)
      大谷明央, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第122回触媒討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] One-pot Synthesis of 2-Pyrrolidone from Pyroglutamic Acid and Glutamic Acid Using Ru/Al2O32018

    • Author(s)
      Satoshi Suganuma, Hiroki Asako, Rika Takagi, Shota Joka, Akihiro Otani, Etsushi Tsuji and Naonobu Katada
    • Organizer
      TOCAT8
    • Related Report
      2018 Research-status Report
  • [Presentation] Ruthenium Loaded on Alumina Catalytically Active for One-pot Synthesis of 2-Pyrrolidone from Pyroglutamic Acid2018

    • Author(s)
      Akihiro Otani*, Shota Joka, Satoshi Suganuma, Etsushi Tsuji and Naonobu Katada
    • Organizer
      TOCAT8
    • Related Report
      2018 Research-status Report
  • [Patent(Industrial Property Rights)] プロリノールの製造方法,複合金属化合物およびその製造方法2020

    • Inventor(s)
      菅沼学史, 加来知奈実, 辻悦司, 片田直伸
    • Industrial Property Rights Holder
      菅沼学史, 加来知奈実, 辻悦司, 片田直伸
    • Industrial Property Rights Type
      特許
    • Filing Date
      2020
    • Related Report
      2020 Annual Research Report
  • [Patent(Industrial Property Rights)] 金属含有ゼオライト複合体、および その触媒、ならびに2-ピロリドンの製造方法2019

    • Inventor(s)
      菅沼学史,片田直伸,辻悦司,大谷明央,金田玲奈
    • Industrial Property Rights Holder
      菅沼学史,片田直伸,辻悦司,大谷明央,金田玲奈
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2019-140757
    • Filing Date
      2019
    • Related Report
      2019 Research-status Report

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

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