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A novel biorefinary technology by controlling intermolecular hydrogen bonding

Research Project

Project/Area Number 23658142
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Wood science
Research InstitutionKyoto University

Principal Investigator

KAWAMOTO Haruo  京都大学, エネルギー科学研究科, 准教授 (80224864)

Co-Investigator(Kenkyū-buntansha) SAKA Shiro  京都大学, エネルギー科学研究科, 教授 (50205697)
Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsバイオマス / バイオリファイナリー / 熱分解反応制御 / ケミカルス / 液体燃料 / 分子間水素結合
Research Abstract

Pyrolysis-based conversion methods are potential biorefinary technologies for the production of liquid and gaseous fuels and useful chemicals from biomass resources. "Charring" reaction, however, reduces the production efficiency of these value-added products. We propose the acid-catalysis mechanism through intermolecular hydrogen bonding for this charring reaction. In this project, we confirmed the proposed mechanism and succeeded to produce C2 and C3 chemicals efficiently from biomass by controlling the intermolecular hydrogen bonding in hydrogen bond acceptor solvents and in the gas-phase reactions.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (57 results)

All 2014 2013 2012 2011 Other

All Journal Article (12 results) (of which Peer Reviewed: 10 results) Presentation (43 results) (of which Invited: 4 results) Book (2 results)

  • [Journal Article] What is Active Cellulose in Pyrolysis? An Approach based on Reactivity of Cellulose Reducing End2014

    • Author(s)
      Matsuoka, S., Kawamoto, H. and Saka S
    • Journal Title

      J. Anal. Appl. Pyrolysis

      Volume: 106 Pages: 138-146

    • DOI

      10.1016/j.jaap.2014.01.011

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Mechanisms for the Formation of Monomers and Oliglmers During the Pyrolysis of a Softwood Lignin2014

    • Author(s)
      Kotake, T, Kawamoto, H., Saka, S.
    • Journal Title

      J. Anal. Appl. Pyrolysis

      Volume: 105 Pages: 309-316

    • DOI

      10.1016/j.jaap.2013.11.018

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Pyrolysis Reactions of Coniferyl Alcohol as a Model of the Primary Structure Formed During Lignin Pyrolysis2013

    • Author(s)
      Kotake, T, Kawamoto, H., Saka, S
    • Journal Title

      J. Anal. Appl. Pyrolysis

      Volume: 104 Pages: 573-584

    • DOI

      10.1016/j.jaap.2013.05.011

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Influence of Hydroxyl Group Configuration on Pyrolytic Formation of 1, 6-Anhydrohexopyranoses From Various Hexoses : An Experimental And Theoretical Study2013

    • Author(s)
      Matsuoka, S., Kawamoto, H., Saka S
    • Journal Title

      J. Anal. Appl. Pyrolysis

      Volume: 103 Pages: 300-306

    • DOI

      10.1016/j.jaap.2012.08.008

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Thermal Reactivities of Non-Reducing Sugars in Polyether -Role of Intermolecular Hydrogen Bondings in Pyrolysis2013

    • Author(s)
      Kawamoto, H., Ueno, Y., Saka S
    • Journal Title

      J. Anal. Appl. Pyrolysis

      Volume: 103 Pages: 287-292

    • DOI

      10.1016/j.jaap.2012.08.009

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Retro-Adel-Type Fragmentation of Reducing Sugars Preferentially Occurring in Polyether at High Temperature : Role of the Ether Oxygen as a Base Catalyst2012

    • Author(s)
      Matsuoka, S., Kawamoto, H. and Saka S.
    • Journal Title

      J. Anal. Appl. Pyrol.

      Volume: 93 Pages: 24-32

    • DOI

      10.1016/j.jaap.2011.09.005

    • Related Report
      2013 Final Research Report 2012 Research-status Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] The Effects of Combining Guaiacol and Syringol on their Pyrolysis2012

    • Author(s)
      Asmadi, M., Kawamoto, H., Saka, S.
    • Journal Title

      Holzforschung

      Volume: 66 Issue: 3 Pages: 323-330

    • DOI

      10.1515/hf.2011.165

    • NAID

      120006601453

    • Related Report
      2013 Final Research Report
  • [Journal Article] Gas-and Solid/Liquid-Phase Reactions during Pyrolysis of Softwood and Hardwood Lignins2011

    • Author(s)
      Asmadi, M., Kawamoto, H., Saka, S.
    • Journal Title

      J. Anal. Appl. Pyrol.

      Volume: 92 Issue: 2 Pages: 417-425

    • DOI

      10.1016/j.jaap.2011.08.003

    • NAID

      120003534353

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Thermal Reactivities of Catechols/Pyrogallols and Cresols/Xylenols as Lignin Pyrolysis Intermediates2011

    • Author(s)
      Asmadi, M., Kawamoto, H., Saka, S.
    • Journal Title

      J. Anal. Appl. Pyrol.

      Volume: 92 Issue: 1 Pages: 76-87

    • DOI

      10.1016/j.jaap.2011.04.012

    • NAID

      120003386624

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Thermal Reactions of Guaiacol and Syringol as Lignin Model Aromatic Nuclei2011

    • Author(s)
      Asmadi, M., Kawamoto, H., Saka, S.
    • Journal Title

      J. Anal. Appl. Pyrol.

      Volume: 92 Issue: 1 Pages: 88-98

    • DOI

      10.1016/j.jaap.2011.04.011

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Reducing End-Group of Cellulose as a Reactive Site for Discoloration2011

    • Author(s)
      Matsuoka, S., Kawamoto, H., Saka S.
    • Journal Title

      Polym. Degrad. Stab.

      Volume: 96 Issue: 7 Pages: 1242-1247

    • DOI

      10.1016/j.polymdegradstab.2011.04.009

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Thermal Glycosylation and Degradation Reactions Occurring at the Reducing Ends of Cellulose during Low-Temperature Pyrolysis2011

    • Author(s)
      Matsuoka, S., Kawamoto, H., Saka S.
    • Journal Title

      Carbohydr. Res.

      Volume: 346(2) Issue: 2 Pages: 272-279

    • DOI

      10.1016/j.carres.2010.10.018

    • NAID

      120002753574

    • Related Report
      2013 Final Research Report
  • [Presentation] リグニン熱分解における低分子化とそれを阻害する分子機構2014

    • Author(s)
      河本晴雄
    • Organizer
      第254回生存圏シンポジウム(第4回生存圏熱帯林人工林フラッグシップシンポジウム)
    • Place of Presentation
      京都
    • Year and Date
      2014-02-27
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] 熱分解におけるリグニンの低分子化とそれを阻害する分子機構2014

    • Author(s)
      河本晴雄, 小竹毅郎, 坂 志朗
    • Organizer
      第64回日本木材学会大会研究発表要旨集
    • Place of Presentation
      松山
    • Related Report
      2013 Final Research Report
  • [Presentation] 加熱速度がセルロース熱分解における分解物の沸騰温度に及ぼす影響2014

    • Author(s)
      庄司妙子, 河本晴雄, 坂 志朗
    • Organizer
      第64回日本木材学会大会研究発表要旨集
    • Place of Presentation
      松山
    • Related Report
      2013 Final Research Report
  • [Presentation] 気相中でのレボグルコサンの熱分解反応機構2014

    • Author(s)
      福留明日香, 河本晴雄, 坂 志朗
    • Organizer
      第64回日本木材学会大会研究発表要旨集
    • Place of Presentation
      松山
    • Related Report
      2013 Final Research Report
  • [Presentation] 熱分解におけるリグニンの低分子化とそれを阻害する分子機構2014

    • Author(s)
      河本晴雄、小竹毅郎、坂 志朗
    • Organizer
      第64回日本木材学会大会
    • Place of Presentation
      松山
    • Related Report
      2013 Annual Research Report
  • [Presentation] 加熱速度がセルロース熱分解における分解物の沸騰温度に及ぼす影響2014

    • Author(s)
      庄司妙子、河本晴雄、坂 志朗
    • Organizer
      第64回日本木材学会大会
    • Place of Presentation
      松山
    • Related Report
      2013 Annual Research Report
  • [Presentation] 気相中でのレボグルコサンの熱分解反応機構2014

    • Author(s)
      福留明日香、河本晴雄、坂 志朗
    • Organizer
      第64回日本木材学会大会
    • Place of Presentation
      松山
    • Related Report
      2013 Annual Research Report
  • [Presentation] Hydrogen bonding promotes pyrolytic reactions of carbohydrate pyrolysis (Oral)2013

    • Author(s)
      Kawamoto, H
    • Organizer
      21st European Biomass Conference & Exhibition. Setting the course for a biobased economy
    • Place of Presentation
      Copenhagen, Denmark
    • Related Report
      2013 Final Research Report
  • [Presentation] Molecular mechanisms in pyrolytic formation of monomers/oliglmers from lignin (Poster)2013

    • Author(s)
      Kawamoto, H., Kotake, T., Saka, S
    • Organizer
      21st European Biomass Conference & Exhibition. Setting the course for a biobased economy
    • Place of Presentation
      Copenhagen, Denmark
    • Related Report
      2013 Final Research Report
  • [Presentation] セルロース熱分解における1, 6-無水糖生成機構(ポスター)2013

    • Author(s)
      河本晴雄, 松岡聖二, 坂 志朗
    • Organizer
      セルロース学会第20回年次大会講演要旨集
    • Place of Presentation
      宇治
    • Related Report
      2013 Final Research Report
  • [Presentation] セルロース系バイオマスのガス化中間体としてのレボグルコサンの気相中での熱分解反応機構(ポスター)2013

    • Author(s)
      福留 明日香, 河本晴雄, 坂 志朗
    • Organizer
      セルロース学会第20回年次大会講演要旨集
    • Place of Presentation
      宇治
    • Related Report
      2013 Final Research Report
  • [Presentation] 側鎖からの水素引抜によるリグニンラジカル連鎖β-エーテル開裂機構の検討(口頭)2013

    • Author(s)
      松田佳子, 河本晴雄, 坂 志朗
    • Organizer
      第58回リグニン討論会講演集
    • Place of Presentation
      高松
    • Related Report
      2013 Final Research Report
  • [Presentation] リグニンの熱分解ラジカル連鎖β-エーテル開裂機構の解明 -Cβ水素引き抜きによる経路-2013

    • Author(s)
      松田佳子, 河本晴雄, 坂 志朗
    • Organizer
      第63回日本木材学会大会研究発表要旨集
    • Place of Presentation
      盛岡
    • Related Report
      2013 Final Research Report
  • [Presentation] セルロース系バイオマスのガス化中間体としてのレボグルコサンの気相での熱分解反応特性2013

    • Author(s)
      福留 明日香, 河本晴雄, 坂 志朗
    • Organizer
      第63回日本木材学会大会研究発表要旨集
    • Place of Presentation
      盛岡
    • Related Report
      2013 Final Research Report
  • [Presentation] Hydrogen bonding promotes pyrolytic reactions of carbohydrate pyrolysis2013

    • Author(s)
      Kawamoto, H.
    • Organizer
      21st European Biomass Conference & Exhibition.
    • Place of Presentation
      Copenhagen
    • Related Report
      2013 Annual Research Report
  • [Presentation] Molecular mechanisms in pyrolytic formation of monomers/oliglmers from lignin2013

    • Author(s)
      Kawamoto, H., Kotake, T., Saka, S.
    • Organizer
      21st European Biomass Conference & Exhibition.
    • Place of Presentation
      Copenhagen
    • Related Report
      2013 Annual Research Report
  • [Presentation] セルロース系バイオマスのガス化中間体としてのレボグルコサンの気相中での熱分解反応機構2013

    • Author(s)
      福留 明日香、河本晴雄、坂 志朗
    • Organizer
      セルロース学会第20回年次大会
    • Place of Presentation
      宇治
    • Related Report
      2013 Annual Research Report
  • [Presentation] セルロース系バイオマスのガス化中間体としてのレボグルコサンの気相での熱分解反応特性2013

    • Author(s)
      福留 明日香、河本晴雄、坂 志朗
    • Organizer
      第63回日本木材学会大会
    • Place of Presentation
      盛岡
    • Related Report
      2012 Research-status Report
  • [Presentation] Aromatic substance and polyether as media for controlled pyrolysis for chemical production from carbohydrates (Poster)2012

    • Author(s)
      Kawamoto, H., Saka, S
    • Organizer
      3rd International Cellulose Conference (ICC2012)
    • Place of Presentation
      Sapporo, Japan
    • Related Report
      2013 Final Research Report
  • [Presentation] Molecular-based study of gas and coke formation in gasification of cellulosic biomass (Poster)2012

    • Author(s)
      Fukutome, A., Kawamoto, H., Saka, S
    • Organizer
      3rd International Cellulose Conference (ICC2012)
    • Place of Presentation
      Sapporo, Japan
    • Related Report
      2013 Final Research Report
  • [Presentation] Thermal reactivities of reducing and non-reducing sugars in polyether : role f inter- and intra-molecular hydrogen bondings in pyrolysis2012

    • Author(s)
      Kawamoto, H., Ueno, Y., Saka, S
    • Organizer
      19th International Symposium on Analytical and Applied Pyrolysis (Pyrolysis 2012)
    • Place of Presentation
      Linz, Austria (Oral)
    • Related Report
      2013 Final Research Report
  • [Presentation] Influence of hydroxyl group configuration on pyrolytic formation of 1, 6-anhydrohexoses from various hexoses : and experimental and theoretical study2012

    • Author(s)
      Matsuoka, S., Kawamoto, H., Saka, S
    • Organizer
      19th International Symposium on Analytical and Applied Pyrolysis (Pyrolysis 2012)
    • Place of Presentation
      Linz, Austria(Poster)
    • Related Report
      2013 Final Research Report
  • [Presentation] 芳香族吾郷物中での非還元糖の熱安定化とその機構(ポスター)2012

    • Author(s)
      河本晴雄, 細谷隆史, 上野貴臣, 坂 志朗
    • Organizer
      セルロース学会第19回年次大会講演要旨集
    • Place of Presentation
      名古屋
    • Related Report
      2013 Final Research Report
  • [Presentation] 糖の熱分解機構 : 気相でなぜ安定化するのか2012

    • Author(s)
      河本晴雄, 坂 志朗
    • Organizer
      第21回日本エネルギー学会大会講演要旨集(口頭)
    • Place of Presentation
      東京(口頭)
    • Related Report
      2013 Final Research Report
  • [Presentation] 広葉樹リグニン熱分解における低分子シリンゴール類/グアイアコール類の生成挙動2012

    • Author(s)
      小竹毅郎, 河本晴雄, 坂 志朗
    • Organizer
      第57回リグニン討論会講演集
    • Place of Presentation
      福岡
    • Related Report
      2013 Final Research Report
  • [Presentation] 非還元糖のポリエーテル中での熱安定化 : 熱分解における分子内及び分子間水素結合の役割(口頭)2012

    • Author(s)
      上野貴臣, 河本晴雄, 坂 志朗
    • Organizer
      第62回日本木材学会大会研究発表要旨集
    • Place of Presentation
      札幌
    • Related Report
      2013 Final Research Report
  • [Presentation] コニフェリルアルコールの熱分解反応特性と針葉樹リグニン熱分解における役割(口頭)2012

    • Author(s)
      小竹毅郎, 河本晴雄, 坂 志朗
    • Organizer
      第62回日本木材学会大会研究発表要旨集
    • Place of Presentation
      札幌
    • Related Report
      2013 Final Research Report
  • [Presentation] Aromatic substance and polyether as media for controlled pyrolysis for chemical production from carbohydrates2012

    • Author(s)
      Kawamoto, H., Saka, S.
    • Organizer
      3rd International Cellulose Conference (ICC2012)
    • Place of Presentation
      Sapporo, Japan
    • Related Report
      2012 Research-status Report
  • [Presentation] Molecular-based study of gas and coke formation in gasification of cellulosic biomass2012

    • Author(s)
      Fukutome, A., Kawamoto, H., Saka, S.
    • Organizer
      3rd International Cellulose Conference (ICC2012)
    • Place of Presentation
      Sapporo, Japan
    • Related Report
      2012 Research-status Report
  • [Presentation] Thermal reactivities of reducing and non-reducing sugars in polyether: role f inter- and intra-molecular hydrogen bondings in pyrolysis2012

    • Author(s)
      Kawamoto, H., Ueno, Y., Saka, S.
    • Organizer
      19th International Symposium on Analytical and Applied Pyrolysis (Pyrolysis 2012)
    • Place of Presentation
      Linz, Austria
    • Related Report
      2012 Research-status Report
  • [Presentation] Influence of hydroxyl group configuration on pyrolytic formation of 1,6-anhydrohexoses from various hexoses: and experimental and theoretical study2012

    • Author(s)
      Matsuoka, S., Kawamoto, H., Saka, S.
    • Organizer
      19th International Symposium on Analytical and Applied Pyrolysis (Pyrolysis 2012)
    • Place of Presentation
      Linz, Austria
    • Related Report
      2012 Research-status Report
  • [Presentation] 芳香族吾郷物中での非還元糖の熱安定化とその機構2012

    • Author(s)
      河本晴雄、細谷隆史、上野貴臣、坂 志朗
    • Organizer
      セルロース学会第19回年次大会
    • Place of Presentation
      名古屋
    • Related Report
      2012 Research-status Report
  • [Presentation] 糖の熱分解機構:気相でなぜ安定化するのか2012

    • Author(s)
      河本晴雄、坂 志朗
    • Organizer
      第21回日本エネルギー学会大会
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] 非還元糖のポリエーテル中での熱安定化:熱分解における分子内及び分子間水素結合の役割2012

    • Author(s)
      上野貴巨、河本晴雄、坂志朗
    • Organizer
      第62回日本木材学会大会
    • Place of Presentation
      北海道大学
    • Related Report
      2011 Research-status Report
  • [Presentation] 熱分解技術の最新動向と分子レベルでの視点からの考察2011

    • Author(s)
      河本晴雄
    • Organizer
      第11回バイオマス合同交流会
    • Place of Presentation
      京都
    • Year and Date
      2011-11-09
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] バイオリファイナリーに向けたリグニン熱分解機構からのアプローチ2011

    • Author(s)
      河本晴雄
    • Organizer
      リグニン討論会若手の会 日本木材学会バイオマス変換研究会 合同講演会
    • Place of Presentation
      鶴岡
    • Year and Date
      2011-09-16
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] Pyrolysis and Secondary Decomposition Reactions of softwood and hardwood lignins (Poster)2011

    • Author(s)
      Asmadi, M., Kawamoto, H., Saka, S
    • Organizer
      19th European Biomass Conference & Exhibition. From Research to Industry and Markets
    • Place of Presentation
      Berlin, Germany
    • Related Report
      2013 Final Research Report
  • [Presentation] コニフェリルアルコール及びシナピルアルコールの熱分解反応特性とリグニン熱分解における役割(口頭)2011

    • Author(s)
      小竹毅郎, 河本晴雄, 坂 志朗
    • Organizer
      第56回リグニン討論会講演集
    • Place of Presentation
      山形
    • Related Report
      2013 Final Research Report
  • [Presentation] 固/液相および気相でのリグニン熱分解機構(口頭)2011

    • Author(s)
      モード・アスマディ, 河本晴雄, 坂 志朗
    • Organizer
      第20回日本エネルギー学会大会講演要旨集
    • Place of Presentation
      大阪
    • Related Report
      2013 Final Research Report
  • [Presentation] 芳香族化合物中でのレボグルコサン及びセルロースの熱分解挙動(口頭)2011

    • Author(s)
      河本晴雄, 安川雄也, 坂 志朗
    • Organizer
      セルロース学会第18回年次大会講演要旨集
    • Place of Presentation
      長野
    • Related Report
      2013 Final Research Report
  • [Presentation] 熱分解技術の最新動向と分子レベルでの視点からの考察2011

    • Author(s)
      河本晴雄
    • Organizer
      第11回バイオマス合同交流会(招待講演)
    • Place of Presentation
      京都
    • Related Report
      2011 Research-status Report
  • [Presentation] 芳香族化合物中でのレボグルコサン及びセルロースの熱分解挙動2011

    • Author(s)
      河本晴雄、安川雄也、坂 志朗
    • Organizer
      セルロース学会第18回年次大会
    • Place of Presentation
      信州大学
    • Related Report
      2011 Research-status Report
  • [Presentation] リグニン熱分解における低分子化とそれを阻害する分子機構

    • Author(s)
      河本晴雄
    • Organizer
      第254回生存圏シンポジウム(第4回生存圏熱帯林人工林フラッグシップシンポジウム)
    • Place of Presentation
      京都
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Book] 第4章 5 リグニンの熱分解による化学物質 in 「リグニン利用の最動向」2013

    • Author(s)
      河本晴雄
    • Publisher
      シーエムシー出版
    • Related Report
      2013 Final Research Report
  • [Book] 第4章 5リグニンの熱分解による化学物質 in 「リグニン利用の最動向」2013

    • Author(s)
      河本晴雄
    • Total Pages
      8
    • Publisher
      シーエムシー出版
    • Related Report
      2013 Annual Research Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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