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Synthesis of all C4 and C5 monools and diols

Research Project

Project/Area Number 20H02519
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 InstitutionTohoku University

Principal Investigator

Nakagawa Yoshinao  東北大学, 工学研究科, 准教授 (10436545)

Project Period (FY) 2020-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥16,120,000 (Direct Cost: ¥12,400,000、Indirect Cost: ¥3,720,000)
Fiscal Year 2022: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2021: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2020: ¥7,540,000 (Direct Cost: ¥5,800,000、Indirect Cost: ¥1,740,000)
Keywordsバイオマス / 触媒・化学プロセス / 還元
Outline of Research at the Start

水素化分解用高性能触媒開発により、糖アルコール等のバイオマス由来含酸素化合物から、あらゆる低分子直鎖アルコールを合成可能とすることを目的とする。アルコールは官能基変換の基点となる化合物であるため、本目的を達成できればバイオマス利用の汎用性が大きく高まり、あらゆる低分子をバイオマスから合成可能とするための基盤となる。この目的を達成するための触媒として、(a) 末端1,2-ジオールの選択的2位除去を行う触媒、(b)末端ジオールの同時除去を行う触媒、(c) 末端OH基選択除去の位置選択性を有する触媒、といった異なる選択性の触媒を開発し、これらの反応を組み合わせてC5以下のアルコールを合成する。

Outline of Final Research Achievements

The catalysts with the following selectivity patterns have been developed: (a) removal of secondary OH group of 1,2-diols, (b) simultaneous removal of vicinal two OH groups, and (c) removal of primary OH group of 1,2-diols. The catalytic reactions with these selectivities are key ones for the selective synthesis of all smaller functionalized molecules from biomass. Combination of these reactions and as well as the already-developed ones, all mono-ols and diols with carbon number <=4 can be now synthesized from biomass.

Academic Significance and Societal Importance of the Research Achievements

これまでバイオマスから得られる化学品はグリセリンやフルフラールなど種類が限られていたが、本研究では多くの種類の低分子アルコールがバイオマスから合成可能であることを示した。アルコールは官能基変換の起点となる化合物であることから、様々な低分子の基礎化学品をバイオマスから合成可能となった。

Report

(4 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Annual Research Report
  • 2020 Annual Research Report
  • Research Products

    (20 results)

All 2023 2022 2021 2020

All Journal Article (11 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 11 results) Presentation (9 results) (of which Int'l Joint Research: 5 results)

  • [Journal Article] 2‐Hydroxyadipic Acid Production by Oxidation of 2‐Hydroxycyclohexanone with Molecular Oxygen2023

    • Author(s)
      Hashimoto Koki、Hatakeyama Kosuke、Yabushita Mizuho、Tomishige Keiichi、Nakagawa Yoshinao
    • Journal Title

      ChemCatChem

      Volume: 15 Issue: 10

    • DOI

      10.1002/cctc.202300212

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Utilization of Ni as a Non-Noble-Metal Co-catalyst for Ceria-Supported Rhenium Oxide in Combination of Deoxydehydration and Hydrogenation of Vicinal Diols2022

    • Author(s)
      Yamaguchi Kosuke、Nakagawa Yoshinao、Li Congcong、Yabushita Mizuho、Tomishige Keiichi
    • Journal Title

      ACS Catalysis

      Volume: 12 Issue: 20 Pages: 12582-12595

    • DOI

      10.1021/acscatal.2c03042

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective C-O Hydrogenolysis of Terminal C-OH Bond in 1,2-Diols over Rutile-Titania-Supported Iridium-Iron Catalysts2022

    • Author(s)
      Liu Ben、Nakagawa Yoshinao、Li Congcong、Yabushita Mizuho、Tomishige Keiichi
    • Journal Title

      ACS Catalysis

      Volume: 12 Issue: 24 Pages: 15431-15450

    • DOI

      10.1021/acscatal.2c04499

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Secondary Monoalcohols from Terminal Vicinal Alcohols over Silica-Supported Rhenium-Modified Ruthenium Catalyst2022

    • Author(s)
      Liu Ben、Sekine Naoyuki、Nakagawa Yoshinao、Tamura Masazumi、Yabushita Mizuho、Tomishige Keiichi
    • Journal Title

      ACS Sustainable Chemistry &amp; Engineering

      Volume: 10 Issue: 3 Pages: 1220-1231

    • DOI

      10.1021/acssuschemeng.1c07023

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Titania-supported molybdenum oxide combined with Au nanoparticles as a hydrogen-driven deoxydehydration catalyst of diol compounds2022

    • Author(s)
      Hacatrjan Schanth、Liu Lujie、Gan Jianxing、Nakagawa Yoshinao、Cao Ji、Yabushita Mizuho、Tamura Masazumi、Tomishige Keiichi
    • Journal Title

      Catalysis Science &amp; Technology

      Volume: 12 Issue: 7 Pages: 2146-2161

    • DOI

      10.1039/d1cy02144c

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Deoxydehydration of Biomass‐Derived Polyols Over Silver‐Modified Ceria‐Supported Rhenium Catalyst with Molecular Hydrogen2022

    • Author(s)
      Yamaguchi Kosuke、Cao Ji、Betchaku Mii、Nakagawa Yoshinao、Tamura Masazumi、Nakayama Akira、Yabushita Mizuho、Tomishige Keiichi
    • Journal Title

      ChemSusChem

      Volume: In press Issue: 10

    • DOI

      10.1002/cssc.202102663

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hydrodeoxygenation of C4?C6 sugar alcohols to diols or mono-alcohols with the retention of the carbon chain over a silica-supported tungsten oxide-modified platinum catalyst2021

    • Author(s)
      Liu Lujie、Cao Ji、Nakagawa Yoshinao、Betchaku Mii、Tamura Masazumi、Yabushita Mizuho、Tomishige Keiichi
    • Journal Title

      Green Chemistry

      Volume: 23 Issue: 15 Pages: 5665-5679

    • DOI

      10.1039/d1gc01486b

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Adsorption of Keggin-Type Polyoxometalates on Rh Metal Particles under Reductive Conditions2021

    • Author(s)
      Nakagawa Yoshinao、Kuwata Ayaka、Yamaguchi Kosuke、Tamura Masazumi、Yabushita Mizuho、Tomishige Keiichi
    • Journal Title

      Inorganic Chemistry

      Volume: 60 Issue: 16 Pages: 12413-12424

    • DOI

      10.1021/acs.inorgchem.1c01644

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structure and performance relationship of silica-supported platinum-tungsten catalysts in selective C-O hydrogenolysis of glycerol and 1,4-anhydroerythritol2021

    • Author(s)
      Liu Lujie、Asano Takehiro、Nakagawa Yoshinao、Gu Minyan、Li Congcong、Tamura Masazumi、Tomishige Keiichi
    • Journal Title

      Applied Catalysis B: Environmental

      Volume: 292 Pages: 120164-120164

    • DOI

      10.1016/j.apcatb.2021.120164

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-pot production of dioctyl ether from 1,2-octanediol over rutile-titania-supported palladium-tungsten catalyst2020

    • Author(s)
      Nakagawa Yoshinao、Hayasaka Hiroki、Asano Takehiro、Tamura Masazumi、Okumura Kazu、Tomishige Keiichi
    • Journal Title

      Molecular Catalysis

      Volume: - Pages: 111208-111208

    • DOI

      10.1016/j.mcat.2020.111208

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Hydrogenolysis of Erythritol over Ir-ReOx/Rutile-TiO2 Catalyst2020

    • Author(s)
      Gu Minyan、Liu Lujie、Nakagawa Yoshinao、Li Congcong、Tamura Masazumi、Shen Zheng、Zhou Xuefei、Zhang Yalei、Tomishige Keiichi
    • Journal Title

      ChemSusChem

      Volume: 14 Issue: 2 Pages: 642-654

    • DOI

      10.1002/cssc.202002357

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Synthesis of secondary mono-alcohols from terminal vicinal alcohols over Ru-ReOx/SiO2 catalyst2022

    • Author(s)
      Ben LIU, Naoyuki SEKINE, Yoshinao NAKAGAWA, Masazumi TAMURA, Mizuho YABUSHITA, Keiichi TOMISHIGE
    • Organizer
      TOCAT9
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Production of adipic acid by aerobic oxidation of 2-methoxycyclohexanone with H33PW12O40 catalyst2022

    • Author(s)
      Yoshinao NAKAGAWA,Kosuke HATAKEYAMA, MasazumiTAMURA, Keiichi TOMISHIGE
    • Organizer
      TOCAT9
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Aerobic oxidative cleavage of 2-hydroxycyclohexanoneo to 2-hydroxyadipic acid2022

    • Author(s)
      Koki HASHIMOTO,Yoshinao NAKAGAWA, Mizuho YABUSHITA, Keiichi TOMISHIGE
    • Organizer
      TOCAT9
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Reduction of 1,2-octanediol to dioctyl ether over WOx-Pd/TiO2 catalyst2022

    • Author(s)
      Yoshinao Nakagawa・Hiroki Hayasaka・Masazumi Tamura・Keiichi Tomishige
    • Organizer
      ICEC2022
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 銀修飾セリア担持レニウム触媒を用いたエリスリトールから1,3-ブタジエンへの脱酸素脱水反応2021

    • Author(s)
      山口功祐・中川善直・田村正純・藪下瑞帆・冨重圭一
    • Organizer
      第128回触媒討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Deoxydehydration of Biomass-derived Polyols over ReOx-Ag/CeO2 catalyst with Molecular Hydrogen2021

    • Author(s)
      Kosuke Yamaguchi, Ji Cao, Yoshinao Nakagawa, Masazumi Tamura, Mizuho Yabushita, Keiichi Tomishige
    • Organizer
      The 18th Japan-Korea Symposium on Catalysis
    • Related Report
      2021 Annual Research Report
  • [Presentation] Deoxydehydration of erythritol to butadiene over ceria-supported rhenium catalysts modified with metals2021

    • Author(s)
      Kosuke Yamaguchi; Yoshinao Nakagawa; Masazumi Tamura; Mizuho Yabushita; Keiichi Tomishige
    • Organizer
      Pacifichem2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ルチルチタニア担持タングステン-パラジウム触媒による1,2-オクタンジオールからジオクチルエーテルの一段合成2020

    • Author(s)
      中川善直・早坂弘樹・田村正純・冨重圭一
    • Organizer
      第126回触媒討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] セリア担持ReOx-Ag触媒によるエリスリトールからブタジエンへの脱酸素脱水(DODH)反応2020

    • Author(s)
      山口功祐・中川善直・田村正純・冨重圭一
    • Organizer
      第50回石油・石油化学討論会
    • Related Report
      2020 Annual Research Report

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Published: 2020-04-28   Modified: 2024-01-30  

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