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Development of new route for the production of isoprene

Research Project

Project/Area Number 21H01711
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 InstitutionChiba University

Principal Investigator

Sato Satoshi  千葉大学, 大学院工学研究院, 教授 (30187190)

Project Period (FY) 2021-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥17,420,000 (Direct Cost: ¥13,400,000、Indirect Cost: ¥4,020,000)
Fiscal Year 2023: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2022: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2021: ¥7,800,000 (Direct Cost: ¥6,000,000、Indirect Cost: ¥1,800,000)
Keywordsイソプレン生成反応 / 3-メチル-1,3-ブタンジオール / 脱水反応 / 不飽和アルコール中間体 / 酸塩基協奏反応 / リモネン解重合 / 3-メチル-2-ブタノン / イソプレン生成 / リモネン / 3-メル-1,3-ブタンジオール / 3-メチル-2-ブタノン
Outline of Research at the Start

本研究では、イソプレン合成のため触媒化学的に製造可能な新規な生成ルート探索を行う。イソペンタン・イソペンテンの脱水素反応以外にも、イソプレン生成のためのルートとして3つのルートが想定でき、① テルペン類の解重合、② C5ジオールの脱水反応、③ C5ケトンのメチル基の転位を伴う脱水反応の3つである。①は容易に想定できるルートで研究例は多い、②③のルートは新規な生成ルートとして研究開発する対象として価値があり、学術的にも興味深い。本研究では、3つのイソプレン生成反応①、②および③に対する触媒化学的な検討を行い、各反応において触媒として機能する物質を学術的に体系化することを目的とする。

Outline of Final Research Achievements

In this study, catalytic chemistry of several new formation routes was investigated in order to develop new routes for isoprene production, which is expected to be in short supply in the future. The dehydration of 3-methyl-1,3-butanediol (MBDO) was investigated as well as the dehydration reaction characteristics of three unsaturated alcohols (UOLs), which are considered to be reaction intermediates. The dehydration of MBDO using rare earth zirconates and other catalysts was investigated, and Y2Zr2O7 and Yb2O3 were identified as effective catalysts with high UOL formation capacity. As a result of the investigation of reaction conditions, it was confirmed that Y2Zr2O7 and Yb2O3 catalysts showed efficient isoprene formation activity at 375°C and 450°C, respectively, in the dehydration of MBDO to isoprene.

Academic Significance and Societal Importance of the Research Achievements

3-メチル-1,3-ブタンジオールからジオレフィンであるイソプレンを生成する反応に対して、Y2Zr2O7およびYb2O3のような酸化物触媒の特定結晶面の酸素欠損点が効果的に機能すること、この反応は2段階の脱水反応で進行し、1段目の不飽和アルコールへの脱水反応と2段目のイソプレンへの脱水反応の活性点の機能が異なることを被毒実験等により明らかにした。このことは触媒化学の発展の上で新しい提案であり、学術的意義は大きい。また、将来的な供給不足が懸念されるイソプレン製造に対するオプションをバイオマスから誘導可能な化合物からの製造可能性を提案できた意義も大きい。

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Annual Research Report
  • 2021 Annual Research Report
  • Research Products

    (34 results)

All 2024 2023 2022 2021 Other

All Journal Article (19 results) (of which Peer Reviewed: 19 results,  Open Access: 8 results) Presentation (12 results) (of which Int'l Joint Research: 4 results,  Invited: 1 results) Remarks (3 results)

  • [Journal Article] Hydrothermally fabricated Yb2O3 catalyst for vapor-phase dehydration of 3-methyl-1,3-butanediol to isoprene2024

    • Author(s)
      R. Kobayashi, E. Kurniawan, T. Hara, Y. Yamada, S. Sato
    • Journal Title

      Applied Catalysis A

      Volume: 670 Pages: 119551-119551

    • DOI

      10.1016/j.apcata.2023.119551

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Vapor-phase deoxydehydration of 2,3-butanediol to 2-butene over MoO3/SiO2 catalyst2024

    • Author(s)
      E. Kurniawan, N. Sannodo, Y. Negishi, H. Kobayashi, Y. Yamada, S. Sato
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 97 Issue: 2

    • DOI

      10.1093/bulcsj/uoad005

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Amorphous silica-alumina modified with silver as an efficient catalyst for vapor-phase dehydration of 1,3-butanediol to 1,3-butadiene2024

    • Author(s)
      Y. Li, E. Kurniawan, F. Sato, T. Hara, Y. Yamada, S. Sato
    • Journal Title

      Applied Catalysis A

      Volume: 669 Pages: 119493-119493

    • DOI

      10.1016/j.apcata.2023.119493

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic dehydration of 1,2-butanediol to 1,3-butadiene over CsH2PO4/SiO22024

    • Author(s)
      T. Inaba, E. Kurniawan, T. Hara, Y. Yamada, S. Sato
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 97 Issue: 5

    • DOI

      10.1093/bulcsj/uoae049

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Efficient conversion of glycerol into 1,2-propanediol over Cu/SiO2 catalyst prepared through impregnation assisted with crown ether2024

    • Author(s)
      S. Sasaki, E. Kurniawan, Y. Yamada, S. Sato
    • Journal Title

      Chem. Lett.

      Volume: 53 Issue: 3

    • DOI

      10.1093/chemle/upae037

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Vapor-phase dehydration of glycerol to acetol over Cu/SiO2 prepared with organic additives2024

    • Author(s)
      S. Sasaki, E. Kurniawan, K. Sato, K. Matsusaka, T. Kojima, T. Hara, Y. Yamada, S. Sato
    • Journal Title

      Applied Catalysis A

      Volume: 671 Pages: 119561-119561

    • DOI

      10.1016/j.apcata.2024.119561

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Vapor-phase Dehydrogenation of 3-Methyl-2-butanol over Silica-supported Cu Catalyst Prepared by Mannitol-assisted Impregnation2024

    • Author(s)
      K. Sato, E. Kurniawan, S. Sasaki, K. Matsusaka, Y. Yamada, S. Sato
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 97 Issue: 3

    • DOI

      10.1093/bulcsj/uoae001

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Chemoselective vapor-phase hydrogenation of 6-methyl-5-hepten-2-one over Cu/SiO2 catalyst2024

    • Author(s)
      E. Kurniawan, K. Matsusaka, K. Sato, S. Sasaki, K. Nakazono, Y. Yamada, S. Sato
    • Journal Title

      Chem. Lett.

      Volume: 53 Issue: 2

    • DOI

      10.1093/chemle/upad019

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Vapor-phase dehydration of 1,3-butanediol to 1,3-butadiene over WO3/SiO2 catalyst2023

    • Author(s)
      E. Kurniawan, L. Yu, R. Kobayashi, T. Hara, Y. Yamada, S. Sato
    • Journal Title

      Applied Catalysis A

      Volume: 666 Pages: 119408-119408

    • DOI

      10.1016/j.apcata.2023.119408

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective formation of isoprene via dehydration of 3-methyl-1,3-butanediol over Y2Zr2O7 catalyst2023

    • Author(s)
      R. Kobayashi, E. Kurniawan, Y. Yamada, S. Sato
    • Journal Title

      Molecular Catalysis

      Volume: 535 Pages: 112854-112854

    • DOI

      10.1016/j.mcat.2022.112854

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective vapor-phase hydrogenation of furfural to furfuryl alcohol over Cu/silica catalysts2023

    • Author(s)
      E. Kurniawan, T. Hayashi, S. Hosaka, Y. Yamada, S. Sato
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 86 Issue: 1 Pages: 8-15

    • DOI

      10.1246/bcsj.20220285

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Catalytic dehydration of crotyl alcohol into 1,3-butadiene over silica-supported metal oxides: Mechanistic features2023

    • Author(s)
      L. Yu, E. Kurniawan, T. Ozawa, H. Kobayashi, Y. Yamada, S. Sato
    • Journal Title

      Molecular Catalysis

      Volume: 537 Pages: 112939-112939

    • DOI

      10.1016/j.mcat.2023.112939

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Vapor-phase dehydrogenation of 1-decanol to decanal over Cu/SiO2 catalyst prepared by organic additives-assisted impregnation2023

    • Author(s)
      S. Hosaka, E. Kurniawan, Y. Yamada, S. Sato
    • Journal Title

      Applied Catalysis A

      Volume: 653 Pages: 119079-119079

    • DOI

      10.1016/j.apcata.2023.119079

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Vapor-phase oxidant-free dehydrogenation of 2,3- and 1,4-butanediol over Cu/SiO2 catalyst prepared by crown-ether-assisted impregnation2023

    • Author(s)
      E. Kurniawan, S. Hosaka, M. Kobata, Y. Yamada, S. Sato
    • Journal Title

      Chemistry

      Volume: 5 Issue: 1 Pages: 406-421

    • DOI

      10.3390/chemistry5010030

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Vapor-phase intramolecular aldol condensation of 2,5-hexanedione over calcium hydroxyapatite catalyst2022

    • Author(s)
      E. Kurniawan, T. Yoshinari, Y. Yamada, S. Sato
    • Journal Title

      Applied Catalysis A

      Volume: 644 Pages: 118812-118812

    • DOI

      10.1016/j.apcata.2022.118812

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly active Ni/SiO2 catalyst prepared through citric acid-assisted impregnation for the hydrogenation of acetoin to 2,3-butanediol2022

    • Author(s)
      K. Nakazono, S. Hosaka, Y. Yamada, S. Sato
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 95 Issue: 3 Pages: 443-450

    • DOI

      10.1246/bcsj.20210447

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Efficient production of 1,3-butadiene from 1,4-butanediol over Yb2O3 catalyst prepared through hydrothermal aging2022

    • Author(s)
      A. Matsuda, F. Sato, Y. Yamada, S. Sato
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 95 Issue: 3 Pages: 506-512

    • DOI

      10.1246/bcsj.20210457

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Vapor-phase dehydration of 1,4-butanediol to 1,3-butadiene over Y2Zr2O7 catalyst2021

    • Author(s)
      A. Matsuda, Y. Matsumura, Y. Yamada, S. Sato
    • Journal Title

      Molecular Catalysis

      Volume: 514 Pages: 111853-111853

    • DOI

      10.1016/j.mcat.2021.111853

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dehydration of 2,3-butanediol to produce 1,3-butadiene over Sc2O3 catalyst prepared through hydrothermal aging2021

    • Author(s)
      K. Nakazono, R. Takahashi, Y. Yamada, S. Sato
    • Journal Title

      Molecular Catalysis

      Volume: 516 Pages: 111996-111996

    • DOI

      10.1016/j.mcat.2021.111996

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Presentation] CeO2ーWO3/SiO2二層触媒による3-メチル-1,3-ブタンジオールの脱水反応2024

    • Author(s)
      小林遼、E. Kurniawan、山田泰弘、佐藤智司
    • Organizer
      触媒学会、第133回触媒討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] Formation of isoprene from 3-methyl-1,3-butanediol over a combined system of CeO2 and W/SiO22023

    • Author(s)
      R. Kobayashi, E. Kurniawan, Y, Yamada, S. Sato
    • Organizer
      International Symposium on Catalysis and Fine Chemicals
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 水熱処理したYb2O3触媒による3-メチル-1,3-ブタンジオールの選択的脱水反応2023

    • Author(s)
      小林遼、山田泰弘、佐藤智司
    • Organizer
      触媒学会、第132回触媒討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] シリカ担持アルカリ金属リン酸塩触媒による1,2-ブタンジオールの脱水反応2023

    • Author(s)
      稲葉貴美、山田泰弘、佐藤智司
    • Organizer
      触媒学会、第132回触媒討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] プロピレングリコールの脱水反応によるアリルアルコールの生成2023

    • Author(s)
      諸岡政史、山田泰弘、佐藤智司、永村裕生、岡村淳志
    • Organizer
      触媒学会、第132回触媒討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 有機物修飾Cu/SiO2触媒によるグリセリン脱水反応2023

    • Author(s)
      佐々木駿、山田泰弘、佐藤智司
    • Organizer
      触媒学会、第132回触媒討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] ジルコニア系触媒による2,5-ヘキサンジオンの気相分子内アルドール縮合2023

    • Author(s)
      安達琢人、山田泰弘、佐藤智司
    • Organizer
      触媒学会、第132回触媒討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 希土類酸化物系触媒の酸素欠損が関与するグリコール類の脱水反応2023

    • Author(s)
      佐藤智司
    • Organizer
      触媒学会、第131回触媒討論会特別シンポジウム
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] Selective formation of isoprene in the dehydration of 3-methyl-1,3-butanediol over Y2Zr2O7 catalyst2022

    • Author(s)
      R. Kobayashi, Y. Yamada, S. Sato
    • Organizer
      TOCAT9 Fukuoka
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Ni/SiO2 catalyst prepared through citrate-assisted impregnation for vapor-phase hydrogenation of acetoin to 2,3-butanediol2022

    • Author(s)
      K. Nakazono, S. Hosaka, Y. Yamada, S. Sato
    • Organizer
      TOCAT9 Fukuoka
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Cu/SiO2 catalyst prepared with organic additive-assisted impregnation for vapor-phase dehydrogenation of 1-decanol2022

    • Author(s)
      S. Hosaka, Y. Yamada, S. Sato
    • Organizer
      TOCAT9 Fukuoka
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 3-メチル-1,3-ブタンジオール脱水によるイソプレン生成反応2022

    • Author(s)
      小林 遼、山田泰弘、佐藤智司
    • Organizer
      触媒学会、第130回触媒討論会
    • Related Report
      2022 Annual Research Report
  • [Remarks] 科学研究費補助金の研究成果概要

    • URL

      https://chem.tf.chiba-u.jp/gacb14/researchkakenlist.html

    • Related Report
      2023 Annual Research Report
  • [Remarks] 反応工学研究室の研究活動「2021-2023年度科学研究費補助金課題」

    • URL

      https://chem.tf.chiba-u.jp/gacb14/research.html#kaken2021

    • Related Report
      2023 Annual Research Report
  • [Remarks] 千葉大学 工学部 総合工学科 共生応用化学コース 資源反応工学研究室

    • URL

      https://chem.tf.chiba-u.jp/gacb14/

    • Related Report
      2023 Annual Research Report

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Published: 2021-04-28   Modified: 2025-01-30  

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