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Green Biomass Sciences Progressed by Ionic Liquids Technology

Research Project

Project/Area Number 25550091
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Design and evaluation of sustainable and environmental conscious system
Research InstitutionTottori University

Principal Investigator

ITOH Toshiyuki  鳥取大学, 工学(系)研究科(研究院), 教授 (50193503)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsイオン液体 / リグノセルロース / リグニン溶解性 / セルロース溶解性 / 3成分分離 / アミノ酸 / 再生使用 / リグニン / 溶解性 / バイオマス / β-アラニン / リジン / アミノ酸イオン液体 / 選択的溶解 / 再析出 / 再生可能資源
Outline of Final Research Achievements

We have found that N-methyl-N-(2-methoxyethyl)pyrolidin-1-ium 2,6-diaminohexanoate ([P1ME][Lys]) dissolved lignin very well at below 60°C, but that 80°C was required for it to dissolve cellulose. Taking advantage of this difference in dissolution ability, direct extraction of lignin from wood biomass has been accomplished under mild conditions without use of any hazardous reagents. We have thus achieved the demonstration of the sacrifice-free separation of cellulose, hemicellulose, and lignin from wood biomass (Japanese cedar: Cryptomeria japonica). We next attempted to dsign ILs that could disscolve a wet cellulose; among tested ILs, tributyl(3-methoxypropylp)phosphonium β-alanine ([P444MP][β-Ala]) showed the highest polarity and dissoved 5 wt% of wet cellulose which included water (1 eq. vs IL ion pair) .

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (48 results)

All 2015 2014 2013 Other

All Journal Article (13 results) (of which Peer Reviewed: 12 results,  Acknowledgement Compliant: 2 results) Presentation (23 results) (of which Invited: 14 results) Book (8 results) Remarks (2 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Lipase-mediated Dynamic Kinetic Resolution (DKR) of Secondary Alcohols in the Presence of Zeolite Using an Ionic Liquid Solvent System2015

    • Author(s)
      Shimomura, K.; Harami, H.; Matsubara, Y.; Nokami, T.; Katada, N.; Itoh, T.
    • Journal Title

      Catalysis Today

      Volume: 242 Pages: 41-48

    • DOI

      10.1016/j.cattod.2014.10.052

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Ionic Liquids Equipped with 2-Methoxyethoxymethyl/Methoxymethyl Groups Using a Simple Microreactor System.2014

    • Author(s)
      Nokami, T.; Matsumoto, K.; Itoh, T.-a.; Fukaya, Y.; Itoh, T.
    • Journal Title

      Organic Process Research & Development

      Volume: 18 Issue: 11 Pages: 1367-1371

    • DOI

      10.1021/op500131u

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of gem-Difluoromethylene Building Blocks through Regioselective Allylation of gem-Difluorocyclopropanes2014

    • Author(s)
      Munemori, D.; Narita, K.; Nokami, T.; Itoh, T.
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 10 Pages: 2638-2641

    • DOI

      10.1021/ol500803r

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-catalyzed Nazarov Reaction of Indole, Benzofuran, and Benzo[b]thiophene Derivatives2014

    • Author(s)
      Sakae, M.; Oshitani, S.; Ibara, C.; Natsuyama, M.; Nokami, T.; Itoh, T.
    • Journal Title

      Heteroatom Chem.

      Volume: 25 Issue: 5 Pages: 482-490

    • DOI

      10.1002/hc.21179

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Allylic Amination of Trifluoromethyl Group Substituted Racemic and Unsymmetrical 1,3-Disubstituted Allylic Acetates by Palladium Catalysts2014

    • Author(s)
      Kawatsura, M.; Terasaki, S.; Minakawa, M.; Hirakawa, T.; Ikeda, K.; Itoh, T.
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 9 Pages: 2443-2445

    • DOI

      10.1021/ol5008229

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed Regio- and Enantioselective Allylic Amination of Racemic 1-Arylally Esters2014

    • Author(s)
      Kawatsura, M.; Uchida, K.; Terasaki, S.; Tsuji, H.; Minakawa, M.; Itoh, T.
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 5 Pages: 1470-1473

    • DOI

      10.1021/ol5002768

    • Related Report
      2014 Annual Research Report 2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Effect of cation structure of ionic liquid on anode properties of Si electrodes for LIB2014

    • Author(s)
      M. Shimizu, H. Usui, K. Matsumoto, T. Nokami, T. Itoh, H. Sakaguchi
    • Journal Title

      J. Electrochem. Soc.

      Volume: 161 Issue: 12 Pages: A1765-A1771

    • DOI

      10.1149/2.0021412jes

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Development of Fullerene Based Molecules as an Acceptor Partner with P3HT for OPV Devices in a Thin Layer Organic Solar Cell2014

    • Author(s)
      Matsumoto, K.; Yoshimura, K.; Sugawara, K.; Uetani, Y.; Hayase, S.; Nokami, T.; Itoh, T.*
    • Journal Title

      ECS Transaction

      Volume: 61(30) Issue: 30 Pages: 13-17

    • DOI

      10.1149/06130.0013ecst

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Possible Means of Realizing a Sacrifice-free Three Component Separation of Lignocellulose from Wood Biomass Using an Amino Acid Ionic Liquid2013

    • Author(s)
      Hamada, Y.; Yoshida, Y.; Asai, A.; Hayase, S.; Nokami, T.; Izumi, S.; Itoh, T.
    • Journal Title

      Green Chem

      Volume: 15 Issue: 7 Pages: 1863-1868

    • DOI

      10.1039/c3gc40445e

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synergetic Activation of Lipase by an Amino Acid with Alkyl-PEG-sulfate Ionic Liquid2013

    • Author(s)
      Yoshiyama, K.; Abe, Y.; Hayse, S.; Nokami, T.; Itoh, T.
    • Journal Title

      Chem. Lett

      Volume: 42 Issue: 6 Pages: 663-665

    • DOI

      10.1246/cl.130171

    • NAID

      10031176043

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photovoltaic Properties of OPV Devices using cis- and trans-2,5-Diarylfulleropyrrolidines as Acceptor Partners with P3HT on an ITO Electrode with PEDOT:PSS2013

    • Author(s)
      Yoshimurra, K.; Sugawara, K.; Sakumichi, S.; Matsumoto, K.; Uetani, Y.; Hayase, S.; Nokami, T.; Itoh, T.
    • Journal Title

      Chemistry Letters

      Volume: 42 Issue: 10 Pages: 1209-1211

    • DOI

      10.1246/cl.130506

    • NAID

      10031201312

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Chronicle Review : Regioselective Synthesis of Trifluoromethyl Group Containing Allylic Amines using Palladium-catalyzed Allylic Amination Pathway2013

    • Author(s)
      Hirakawa, T.; Kawatsura, M. ; Itoh, T.
    • Journal Title

      J. Fluorine Chem.

      Volume: 152 Pages: 62-69

    • DOI

      10.1016/j.jfluchem.2013.03.008

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] イオン液体の特徴,可能性とこれからの研究テーマ(特集号依頼論文)2013

    • Author(s)
      伊藤敏幸
    • Journal Title

      月刊「研究開発リーダー」

      Volume: No.11 Pages: 41-46

    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of gem-Difluoromethylene Building Blocks through Regioselective Allylation of gem-Difluorocyclopropanes(招待講演)2014

    • Author(s)
      Toshiyuki Itoh
    • Organizer
      Japan/Russian Conference on Fluorine Chemistry and Friends 2014
    • Place of Presentation
      名古屋工業大学
    • Year and Date
      2014-12-09
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Development of Ionic Liquid Type Activating Agents for Lipasecatalyzed Asymmetric Transesterification2014

    • Author(s)
      Toshiyuki Itoh, Yuko Hamada, Kohei Yoshida, Ryo-ichi Asai
    • Organizer
      2014 Sophia Symposium on Ionic Liquids
    • Place of Presentation
      上智大学,東京
    • Year and Date
      2014-10-31 – 2014-11-01
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Sacrifice-free Three Component Separation of Lignocellulose from Wood Biomass Using Amino Acid Ionic Liquids2014

    • Author(s)
      Toshiyuki Itoh
    • Organizer
      International Forum on Green Integrative Biotechnology (IF-GIB)
    • Place of Presentation
      Tsinghua University, Beijing, China
    • Year and Date
      2014-10-22
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] gem-Difluorocyclopropanes: Applications for Material and Medicinal Sciences(招待講演)2014

    • Author(s)
      Toshiyuki Itoh
    • Organizer
      The 5th China-Japan-Korea Joint Symposium on Fluorine Chemistry
    • Place of Presentation
      上海有機化学研究所,Shanghai, China
    • Year and Date
      2014-10-20 – 2014-10-21
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] イオン液体とフローリアクター反応2014

    • Author(s)
      野上敏材,○伊藤敏幸
    • Organizer
      岡山マイクロリアクターネット講演会
    • Place of Presentation
      岡山大学
    • Year and Date
      2014-10-17
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Phosphonium Alkyl-PEG 
Sulfate Ionic Liquids as a Novel Activating Agents for Lipase(基調講演)2014

    • Author(s)
      Yui Matsubara, Hiroyuki Harami,Yukinobu Fukaya,Toshiki Nokami,a Toshiyuki Itoh*
    • Organizer
      4th Asia-Pacific Conference on Ionic Liquids and Green Processes / 6th Australasian Symposium on Ionic Liquids
    • Place of Presentation
      Sydney, Australia
    • Year and Date
      2014-09-28 – 2014-10-01
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Development of Ionic Liquid Type Activating Agents for Lipase-catalyzed Asymmetric Transesterification2014

    • Author(s)
      Toshiyuki Itoh
    • Organizer
      International Symposium on Advanced Biological Engineering
    • Place of Presentation
      Tsinghua University, Beijing, China
    • Year and Date
      2014-09-02 – 2014-09-03
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 鉄触媒反応とイオン液体2014

    • Author(s)
      伊藤敏幸
    • Organizer
      有機合成化学協会,若手化学者のためのセミナー,第30回化学道場
    • Place of Presentation
      岡山県倉敷市大浜海岸,下電ホテル
    • Year and Date
      2014-08-29 – 2014-08-30
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Iron salt-catalyzed Chirality Memorized Alkylation of Indol with 1-Aryl-2-(trimethylsilyl)ethanol(口頭発表)2014

    • Author(s)
      Shun-suke OSHITANI, Toshiki NOKAMI, Toshiyuki ITOH*
    • Organizer
      XXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      札幌市,ロイトン札幌
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Sacrifice-Free Three Component Separation of Lignocellulose from Wood Biomass Using Ionic Liquids2014

    • Author(s)
      Yukoh Hamada, Ryo-ichi Asai, Toshikki Nokami, Yukinobu Fukaya, Toshiyuki Itoh *
    • Organizer
      EUCHEM (Molten Salts and Ionic Liquids XXV)
    • Place of Presentation
      Tallinn, Estonia
    • Year and Date
      2014-07-06 – 2014-07-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] セルロースおよびリグニン溶解性イオン液体のデザイン(特別講演:基調講演)2014

    • Author(s)
      伊藤 敏幸
    • Organizer
      平成26年度イオン液体研究会
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Year and Date
      2014-06-17
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Development of Fullerene Based Molecules as an Acceptor Partner with P3HT for OPV Devices in a Thin Layer Organic Solar Cell(口頭発表)2014

    • Author(s)
      Toshiyuki Itoh *, Ken Yoshimura, Kiyotaka Sugawara, Shigeki Sakumichi, Kei Matsumoto, Yasunori Uetani, Shuichi Hayase, Toshiki Nokami
    • Organizer
      225th ECS meeting, Manual Baizer Memorial Award Symposium in Organic Electrochemistry
    • Place of Presentation
      Orland, FL, USA
    • Year and Date
      2014-05-11 – 2014-05-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] Sacrifice-free Three Component Separation of Lignocellulose from Wood Biomass Using Amino Acid Ionic Liquids(基調講演)2014

    • Author(s)
      Toshiyuki Itoh,* Yuko Hamada, Kohei Yoshida, Ryo-ichi Asai, Yukinobu Fukaya, Toshiki Nokami
    • Organizer
      4th International Congress on Green Process Engineering
    • Place of Presentation
      Sevilla (Spain)
    • Year and Date
      2014-04-07 – 2014-04-11
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] エーテル側鎖を有するイオン液体のフロー合成(口頭発表),2B7-492014

    • Author(s)
      松本 訓伸・伊藤 考昭・野上 敏材・深谷 幸信・伊藤 敏幸
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      愛知県,名古屋市,名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] 二酸化炭素吸収力を持つホスホニウム塩イオン液体(口頭発表),3C2-022014

    • Author(s)
      谷口貴之・牧野貴至・金久保光央・早瀬修一・深谷幸信・野上敏材・伊藤敏幸
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      愛知県,名古屋市,名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] Design of Ionic Liquids for Direct Lignin Extraction from Wood Chips(口頭発表)2013

    • Author(s)
      Toshiyuki Itoh, Yuko Hamada, Kohei Yoshida, Ryo-ichi Asai
    • Organizer
      5th Congress on Ionic Liquids
    • Place of Presentation
      Algarve, Portugal
    • Related Report
      2013 Research-status Report
  • [Presentation] Amino acid ionic liquid as an efficient cosolvent of dimethyl sulfoxide to realize cellulose dissolution at room temperature (ポスター発表)2013

    • Author(s)
      Toshiyuki Itoh, Kohei Yoshida, Ryo-ichi Asai
    • Organizer
      5th Congress on Ionic Liquids
    • Place of Presentation
      Algarve, Portugal
    • Related Report
      2013 Research-status Report
  • [Presentation] セルロース溶解性を示すアミノ酸イオン液体とジメチルスルホキシドならびにアセトニトリル混合溶媒の開発(ポスター発表)2013

    • Author(s)
      浅井凌一,吉田幸平,早瀬修一,野上敏材,伊藤敏幸
    • Organizer
      第2回 JACI/GSCシンポジウム(第13回 GSCシンポジウム)
    • Place of Presentation
      大阪市,メルパルク大阪
    • Related Report
      2013 Research-status Report
  • [Presentation] アミノ酸イオン液体を用いる木質バイオマスの3成分分離(ポスター発表)2013

    • Author(s)
      濱田祐光,吉田幸平,浅井凌一,早瀬修一,野上敏材,伊藤敏幸
    • Organizer
      第2回 JACI/GSCシンポジウム(第13回 GSCシンポジウム)
    • Place of Presentation
      大阪市,メルパルク大阪
    • Related Report
      2013 Research-status Report
  • [Presentation] Realizing a Sacrifice-free Three Component Separation of Lignocellulose from Wood Biomass Using an Amino Acid Ionic Liquid2013

    • Author(s)
      Toshiyuki Itoh, Yuko Hamada, Kohei Yoshida, Ryo-ichi Asai, Toshiki Nokami
    • Organizer
      WBS 2013 World Bioenergy Symposium
    • Place of Presentation
      Rio de Janeiro, Brazil
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] イオン液体によるリグノセルロースの三成分分離法

    • Author(s)
      伊藤敏幸
    • Organizer
      経済産業省『バイオマス・ファインケミカルズ・リファイナリー・セミナー』
    • Place of Presentation
      岡山市ピュアリティまきび 2F「孔雀」
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] バイオマス燃料のためのリグニンやセルロース溶解性イオン液体の開発について

    • Author(s)
      伊藤敏幸
    • Organizer
      第10回鳥取県新エネルギー活用研究会
    • Place of Presentation
      鳥取市,鳥取大学広報センター2C
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] イオン液体によるリパーゼ触媒反応の活性化

    • Author(s)
      伊藤敏幸
    • Organizer
      第63回大阪府立大学 有機化学研究会(白鷺セミナー)
    • Place of Presentation
      大阪府堺市,大阪府立大学,中百舌鳥キャンパス 理学部サイエンスホール
    • Related Report
      2013 Research-status Report
    • Invited
  • [Book] セルロースナノファイバーの調製,分散・複合化と製品応用-分離・解離技術/表面改質/凝集対策-2015

    • Author(s)
      伊藤敏幸
    • Total Pages
      9
    • Publisher
      情報技術協会(東京)
    • Related Report
      2014 Annual Research Report
  • [Book] Production of Biofuels and Chemicals with lonic Liquids, Biofuels and Biorefineries Volume 12014

    • Author(s)
      Toshiyuki Itoh
    • Total Pages
      15
    • Publisher
      Springer (New York)
    • Related Report
      2014 Annual Research Report
  • [Book] Environmentally Friendly Syntheses Using Ionic Liquids2014

    • Author(s)
      Toshiyuki Itoh
    • Total Pages
      21
    • Publisher
      CRC Press, Taylor & Francis Group (New York)
    • Related Report
      2014 Annual Research Report
  • [Book] CSJ カレントレビュー17,「極限環境の生体分子-過酷な環境下での機能を科学する-,日本化学会編2014

    • Author(s)
      伊藤敏幸
    • Total Pages
      7
    • Publisher
      化学同人
    • Related Report
      2014 Annual Research Report
  • [Book] 化学便覧 応用化学編 第7版,編集委員長辰巳敬,公益社団法人日本化学会2014

    • Author(s)
      伊藤敏幸
    • Total Pages
      1
    • Publisher
      丸善出版 (東京)
    • Related Report
      2014 Annual Research Report
  • [Book] Production of Biofuels and Chemicals with lonic Liquids (ISBN 978-94-007-7710-1)2014

    • Author(s)
      Toshiyuki Itoh
    • Total Pages
      16
    • Publisher
      Springer,New York
    • Related Report
      2013 Research-status Report
  • [Book] 有機合成実験法ハンドブック,有機合成化学協会編2014

    • Author(s)
      伊藤敏幸
    • Publisher
      丸善出版,東京
    • Related Report
      2013 Research-status Report
  • [Book] 化学便覧 応用化学編 第7版,編集委員長辰巳敬,公益社団法人日本化学会2014

    • Author(s)
      伊藤敏幸
    • Publisher
      丸善出版,東京
    • Related Report
      2013 Research-status Report
  • [Remarks] 伊藤研究室ホームページ

    • URL

      http://www.chem.tottori-u.ac.jp/~itoh/

    • Related Report
      2014 Annual Research Report
  • [Remarks] 木質バイオマスからのイオン液体を用いる省エネルギーリグニン抽出法の開発

    • URL

      http://www.cjrd.tottori-u.ac.jp/seeds_cgi/disp.cgi?data_num=20121211105312

    • Related Report
      2014 Annual Research Report
  • [Patent(Industrial Property Rights)] フラーレン誘導体およびそれを用いた有機光電変換素子2013

    • Inventor(s)
      伊藤敏幸,上谷保則,藤原 淳
    • Industrial Property Rights Holder
      国立大学法人 鳥取大学,住友化学株式会社
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2013-142700
    • Filing Date
      2013-07-08
    • Related Report
      2013 Research-status Report
  • [Patent(Industrial Property Rights)] リグニン溶解性イオン液体,リグニン溶解性イオン液体を使用したバイオマスからのリグニン抽出方法2013

    • Inventor(s)
      伊藤敏幸
    • Industrial Property Rights Holder
      国立大学法人鳥取大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2012-143093
    • Filing Date
      2013-05-29
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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