Continuous direct biomass conversion process using ionic liquids

• Project/Area Number: 18H02253
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Review Section: Basic Section 40020:Wood science-related
• Research Institution: Kanazawa University
• Principal Investigator: Takahashi Kenji 金沢大学, 生命理工学系, 教授 (00216714)
• Co-Investigator(Kenkyū-buntansha): 廣瀬 大祐 金沢大学, 物質化学系, 助教 (60806686)
• Project Period (FY): 2018-04-01 – 2022-03-31
• Project Status: Completed (Fiscal Year 2021)
• Budget Amount: ¥12,610,000 (Direct Cost: ¥9,700,000、Indirect Cost: ¥2,910,000); Fiscal Year 2021: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2020: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2019: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000); Fiscal Year 2018: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
• Keywords: イオン液体 / バイオマス / 連続変換プロセス / 二軸混練 / セルロース / 二軸混錬

Outline of Final Research Achievements

The development of a biomass conversion method for lignocelluloses to produce bio-based plastics using ionic liquids and their application to flow reaction using twin-screw extruder was investigated. The effect of ionic liquids in modification reactions was clarified. Direct conversion of lignocellulose became possible by this method. Furthermore, a new biomass conversion method with low environmental impact was developed, and its applicability to flow reactions was demonstrated.

Academic Significance and Societal Importance of the Research Achievements

近年、有限かつ環境に悪影響を与える化石資源から天然バイオマス資源への転換が求められている。本研究はバイオマスプラスチックを安価かつ簡便に合成する手法に関するものである。有機化学および化学工学の両面からのアプローチにより、天然バイオマス資源から直接かつ連続的にバイオマスプラスチックを合成することが可能となった。これらの成果としてバイオマスプラスチック合成において、環境影響を示す指標の一つであるE-ファクター値を大幅に改善することに成功した。

Research Products

• [Int'l Joint Research] Carnegie Mellon University(米国)
• [Journal Article] Low waste process of rapid cellulose transesterification using ionic liquid/DMSO mixed solvent: Towards more sustainable reaction systems (2021)
  • Author(s): Milotskyi Romain、Szabo Laszlo、Fujie Tetsuo、Sakata Kintaro、Wada Naoki、Takahashi Kenji
  • Journal Title: Carbohydrate Polymers Volume: 256 Pages: 117560-117560
  • DOI: 10.1016/j.carbpol.2020.117560
  • Peer Reviewed
• [Journal Article] Direct Conversion of Sugarcane Bagasse into an Injection-Moldable Cellulose-Based Thermoplastic via Homogeneous Esterification with Mixed Acyl Groups (2021)
  • Author(s): Suzuki Shiori、Hikita Hibiki、Hernandez Stephanie C.、Wada Naoki、Takahashi Kenji
  • Journal Title: ACS Sustainable Chemistry & Engineering Volume: - Issue: 17 Pages: 5933-5941
  • DOI: 10.1021/acssuschemeng.1c00306
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Direct Synthesis of Full-Biobased Cellulose Esters from Essential Oil Component α,β-Unsaturated Aldehydes (2021)
  • Author(s): Kusuma Samuel Budi Wardhana、Hirose Daisuke、Yoshizawa Akina、Szabo Laszlo、Ina Daiki、Wada Naoki、Takahashi Kenji
  • Journal Title: ACS Sustainable Chemistry & Engineering Volume: 9 Issue: 25 Pages: 8450-8457
  • DOI: 10.1021/acssuschemeng.1c01267
  • Peer Reviewed
• [Journal Article] Green Conversion of Total Lignocellulosic Components of Sugarcane Bagasse to Thermoplastics Through Transesterification Using Ionic Liquid (2021)
  • Author(s): Suzuki Shiori、Hamano Yosuke、Hernandez Stephanie C.、Wada Naoki、Takahashi Kenji
  • Journal Title: ACS Sustainable Chemistry & Engineering Volume: 9 Issue: 45 Pages: 15249-15257
  • DOI: 10.1021/acssuschemeng.1c05281
  • Peer Reviewed
• [Journal Article] Selective Modification of Aliphatic Hydroxy Groups in Lignin Using Ionic Liquid (2021)
  • Author(s): Suzuki Shiori、Kurachi Shimon、Wada Naoki、Takahashi Kenji
  • Journal Title: Catalysts Volume: 11 Issue: 1 Pages: 120-120
  • DOI: 10.3390/catal11010120
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Controlled acetylation of kraft lignin for tailoring polyacrylonitrile-kraft lignin interactions towards the production of quality carbon nanofibers (2021)
  • Author(s): Szabo Laszlo、Milotskyi Romain、Ueda Hisai、Tsukegi Takayuki、Wada Naoki、Takahashi Kenji
  • Journal Title: Chemical Engineering Journal Volume: 405 Pages: 126640-126640
  • DOI: 10.1016/j.cej.2020.126640
  • Peer Reviewed
• [Journal Article] Understanding and Suppression of Side Reaction during Transesterification of Phenolic Hydroxyl Groups of Lignin with Vinyl Ester (2020)
  • Author(s): Suzuki Shiori、Ishikuro Akinari、Hamano Yosuke、Hirose Daisuke、Wada Naoki、Takahashi Kenji
  • Journal Title: Chemistry Letters Volume: 49 Issue: 8 Pages: 900-904
  • DOI: 10.1246/cl.200202
  • NAID: 130007884716
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Green Synthesis and Fractionation of Cellulose Acetate by Controlling the Reactivity of Polysaccharides in Sugarcane Bagasse (2020)
  • Author(s): Suzuki Shiori、Yada Risa、Hamano Yosuke、Wada Naoki、Takahashi Kenji
  • Journal Title: ACS Sustainable Chemistry & Engineering Volume: 8 Issue: 24 Pages: 9002-9008
  • DOI: 10.1021/acssuschemeng.0c01639
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Electron beam induced strengthening of a short carbon fiber reinforced green thermoplastic composite: key factors determining materials performance (2019)
  • Author(s): Laszlo Szabo, Sari Imanishi, Tetsuo Fujie, Masaki Nishio, Daisuke Hirose, Takayuki Tsukegi, Kentaro Taki, Kazuaki Ninomiya and Kenji Takahashi
  • Journal Title: Composites Part A: Applied Science and Manufacturing Volume: 121 Pages: 386-396
  • DOI: 10.1016/j.compositesa.2019.03.046
  • Peer Reviewed
• [Journal Article] Transesterification Reaction of Cellulose with Inactive Esters in Ionic Liquids Acting as Both Catalysts and Solvents (2019)
  • Author(s): Samuel B. W. Kusuma, Daisuke Hirose and Kenji Takahashi
  • Journal Title: Chemistry Letters Volume: 48 Issue: 9 Pages: 1122-1125
  • DOI: 10.1246/cl.190392
  • NAID: 130007703021
  • Peer Reviewed / Open Access
• [Journal Article] Chemical Modification of Plasticized Lignins Using Reactive Extrusion (2019)
  • Author(s): Romain Milotskyi, Laszlo Szabo, Kenji Takahashi and Christophe Bliard
  • Journal Title: Frontiers in Chemistry Volume: 7
  • DOI: 10.3389/fchem.2019.00633
  • Peer Reviewed
• [Journal Article] Direct one-step synthesis of a formally fully bio-based polymer from cellulose and cinnamon flavor (2019)
  • Author(s): Daisuke Hirose, Samuel Budi Wardhana Kusuma, Daiki Ina, Naoki Wada and Kenji Takahashi
  • Journal Title: Green Chemistry Volume: 21 Issue: 18 Pages: 4927-4931
  • DOI: 10.1039/c9gc01333d
  • Peer Reviewed / Open Access
• [Journal Article] Quantitative analysis of native reactive functional groups on carbon fiber surface: An electrochemical approach (2019)
  • Author(s): Laszlo Szabo, Romain Milotskyi, Takayuki Tsukegi, Naoki Wada and Kenji Takahashi
  • Journal Title: Applied Surface Science Volume: 494 Pages: 315-325
  • DOI: 10.1016/j.apsusc.2019.07.185
  • Peer Reviewed
• [Journal Article] Effect of anion in carboxylate-based ionic liquids on catalytic activity of transesterification with vinyl esters and the solubility of cellulose (2019)
  • Author(s): Hirose Daisuke、Wardhana Kusuma Samuel Budi、Nomura Shuhei、Yamaguchi Makoto、Yasaka Yoshiro、Kakuchi Ryohei、Takahashi Kenji
  • Journal Title: RSC Advances Volume: 9 Issue: 7 Pages: 4048-4053
  • DOI: 10.1039/c8ra10042j
  • Peer Reviewed / Open Access
• [Journal Article] Lignin as a Functional Green Coating on Carbon Fiber Surface to Improve Interfacial Adhesion in Carbon Fiber Reinforced Polymers (2019)
  • Author(s): Szabo Laszlo、Imanishi Sari、Tetsuo Fujie、Hirose Daisuke、Ueda Hisai、Tsukegi Takayuki、Ninomiya Kazuaki、Takahashi Kenji
  • Journal Title: Materials Volume: 12 Issue: 1 Pages: 159-159
  • DOI: 10.3390/ma12010159
  • Peer Reviewed / Open Access
• [Journal Article] Cellulose triacetate synthesis via one-pot organocatalytic transesterification and delignification of pretreated bagasse (2018)
  • Author(s): Suzuki Shiori、Shibata Yoshiki、Hirose Daisuke、Endo Takatsugu、Ninomiya Kazuaki、Kakuchi Ryohei、Takahashi Kenji
  • Journal Title: RSC Advances Volume: 8 Issue: 39 Pages: 21768-21776
  • DOI: 10.1039/c8ra03859g
  • Peer Reviewed
• [Journal Article] Interphase Engineering of a Cellulose-Based Carbon Fiber Reinforced Composite by Applying Click Chemistry (2018)
  • Author(s): Szabo Laszlo、Imanishi Sari、Kawashima Naohiro、Hoshino Rina、Hirose Daisuke、Tsukegi Takayuki、Ninomiya Kazuaki、Takahashi Kenji
  • Journal Title: ChemistryOpen Volume: 7 Issue: 9 Pages: 720-729
  • DOI: 10.1002/open.201800180
  • Peer Reviewed / Open Access
• [Journal Article] Efficient pretreatment of bagasse at high loading in an ionic liquid (2018)
  • Author(s): Aung Ei Mon、Endo Takatsugu、Fujii Shunsuke、Kuroda Kosuke、Ninomiya Kazuaki、Takahashi Kenji
  • Journal Title: Industrial Crops and Products Volume: 119 Pages: 243-248
  • DOI: 10.1016/j.indcrop.2018.04.006
  • Peer Reviewed
• [Journal Article] CS2 capture in the ionic liquid 1-alkyl-3-methylimidazolium acetate: reaction mechanism and free energetics (2018)
  • Author(s): Yan Fangyong、Kakuchi Ryohei、Takahashi Kenji、Kim Hyung J.
  • Journal Title: Physical Chemistry Chemical Physics Volume: 20 Issue: 29 Pages: 19339-19349
  • DOI: 10.1039/c8cp01724g
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Dual Catalytic Activity of an Ionic Liquid in Lignin Acetylation and Deacetylation (2018)
  • Author(s): Suzuki Shiori、Ishikuro Akinari、Hirose Daisuke、Ninomiya Kazuaki、Takahashi Kenji
  • Journal Title: Chemistry Letters Volume: 47 Issue: 7 Pages: 860-863
  • DOI: 10.1246/cl.180350
  • NAID: 130007402821
  • Peer Reviewed
• [Presentation] Low Waste Process of Rapid Cellulose Transesterification Using Ionic Liquid/DMSO Mixed Solvent: Towards More Sustainable Reaction Systems (2020)
  • Author(s): Romain Milotskyi, Laszlo Szabo, Tetsuo Fujie, Kintaro Sakata, Naoki Wada, Kenji Takahashi
  • Organizer: The International Polymer Conference of Thailand 2020 (PCT-10),
  • Int'l Joint Research / Invited
• [Presentation] Biomass refinery using ionic liquids (2019)
  • Author(s): Kenji Takahashi
  • Organizer: BBC2019
  • Int'l Joint Research
• [Presentation] Cellulose production into ionic solvent (2019)
  • Author(s): Kenji Takahashi
  • Organizer: 5th PolyNat International Industries Forum
  • Int'l Joint Research / Invited
• [Presentation] Regioselective synthesis of cellulose ester: Application of carbon13 isotope for efficient detection by 13c-NMR (2019)
  • Author(s): Kenji Takahashi
  • Organizer: 14th Tihany Symposium on Radiation Chemistry,
  • Int'l Joint Research / Invited
• [Presentation] Carbon Fiber Reinforced Plastic made from Thermoplastic Cellulose Resin (2019)
  • Author(s): Kenji Takahashi
  • Organizer: 2nd Asian-French Workshop on Polymer Science (AFWPS 2019)
  • Int'l Joint Research / Invited
• [Presentation] Polymer reaction of Cellulose in ionic liquids and formation of high performance thermoplastic for Carbon fiber reinforced plastic (2019)
  • Author(s): Kenji Takahashi
  • Organizer: International Congress on Advanced Materials Sciences and Engineering（AMSE）
  • Int'l Joint Research / Invited
• [Presentation] Chemical Modification of Plasticized Lignins Using Reactive Extrusion (2019)
  • Author(s): Romain Milotskyi, Laszlo Szabo, Kenji Takahashi, Christophe Bliard
  • Organizer: 1st International Lignin Symposium in Sapporo
  • Int'l Joint Research
• [Presentation] Quantitative analysis of native reactive functional groups on carbon fiber surface for high performance CFRP (2019)
  • Author(s): Kenji Takahashi
  • Organizer: 9th East Asia Symposium on Functional Dyes and Advanced Materials (EAS9)
  • Int'l Joint Research / Invited
• [Presentation] 二軸混練押出機とイオン液体触媒を用いたリグノセルロースの連続的エステル化反応 (2019)
  • Author(s): 坂田金太郎, 玄田雅志, 廣瀬大祐, 和田直樹, 瀧健太郎, 高橋憲司
  • Organizer: プラスチック成形加工学会 第３０回年次大会
• [Presentation] 天然精油含有アルデヒド成分とセルロースを用いる直接的完全バイオベースポリマー合成 (2019)
  • Author(s): 廣瀬大祐, Samuel Kusuma, 伊奈大希, 和田直樹, 高橋憲司
  • Organizer: セルロース学会第26回年次大会
• [Presentation] 酢酸テトラブチルアンモニウムの触媒作用を利用したセルロースナノファイバーのエステル化 (2019)
  • Author(s): 城谷恭弥, 和田直樹, 高橋憲司
  • Organizer: 第68回高分子討論会
• [Presentation] 熱安定化剤添加による熱可塑性セルロースエステルの成形温度領域の拡大 (2019)
  • Author(s): 藤江哲夫, 廣瀬大祐, 高橋憲司, 上田久偉, 附木貴行, 山下博, 鵜澤潔
  • Organizer: プラスチック成型加工学会 第27回秋季大会
• [Presentation] イオン液体を用いたリグニンのエステル交換反応：副反応の抑制と主反応の促進 (2019)
  • Author(s): 鈴木栞, 石黒明成, 廣瀬大祐, 高橋憲司
  • Organizer: 第10回イオン液体討論会
• [Presentation] Polymer reaction of cellulose in ionic liquids as catalysts (2018)
  • Author(s): Kenji Takahashi
  • Organizer: 5th French-Brazilian Meeting on Polymers
  • Int'l Joint Research / Invited
• [Presentation] Homogeneous esterification of cellulose with a methyl ester in an imidazolium carboxylate ionic liquid (2018)
  • Author(s): Samuel Kusuma, Shuhei Nomura, Makoto Yamaguchi, Daisuke Hirose, Yoshiro Yasaka, Kenji Takahashi
  • Organizer: The 6th Asian-Pacific Conference on ionic Liquids& Green Processes (APCIL6)
  • Int'l Joint Research
• [Presentation] One-pot conversion of lignocellulosic biomass into flexible and good thermal processable plastics (2018)
  • Author(s): Shiori Suzuki, Yosuke Hamano, Stephanie C. Hernandez, Naoki Wada, Kenji Takahashi
  • Organizer: The 6th Asian-Pacific Conference on ionic Liquids& Green Processes (APCIL6)
  • Int'l Joint Research
• [Presentation] Dual catalytic activity of an ionic liquid in lignin acetylation and deacetylation (2018)
  • Author(s): Kenji Takahashi, Shiori Suzuki
  • Organizer: Gordon Research Conference
  • Int'l Joint Research
• [Presentation] CFRP composites made from thermoplastic resin derived from cellulose: Chemical design targeting enhanced fiber-resin adhesion, European conference on composite material (2018)
  • Author(s): Yoshiro Yasaka, Rina Hoshino, Osuke Ishida, Jyunichi Kitada, Kiyoshi Uzawa, Kenji Takahashi
  • Organizer: European conference on composite material, ECCM18
  • Int'l Joint Research
• [Presentation] イオン液体を用いたリグノセルロース系バイオマスの均一系エステル交換反応ー機能性リグノセルロースプラスチックの開発ー (2018)
  • Author(s): 鈴木栞, 引田響, Stephanie C. Hernandez, 浜野洋輔, 和田直樹, 高橋憲司
  • Organizer: 第69回日本木材学会大会
• [Presentation] イオン液体の触媒機能を用いたセルロースのエステル交換反応 (2018)
  • Author(s): 廣瀬大祐, 野村周平, 丸山千恵, Kusuma Samuel, 高橋憲司
  • Organizer: 第67回高分子討論会
  • Invited
• [Presentation] クラフトリグニンの分子内エステル交換反応を利用した脂肪族性水酸基の迅速な選択的アセチル化 (2018)
  • Author(s): 鈴木栞, 倉知志門, 和田直樹, 高橋憲司
  • Organizer: 第69回日本木材学会大会
• [Presentation] イオン液体触媒による脂肪族および芳香族性リグニン水酸基の選択的エステル交換反応 (2018)
  • Author(s): 鈴木栞, 倉知志門, 和田直樹, 高橋憲司
  • Organizer: 第9回イオン液体討論会
• [Presentation] リグノセルロース系バイオマスの直接誘導体化による加工性に優れたバイオマスプラスチックの開発 (2018)
  • Author(s): 鈴木栞, Stephanie Hernandez, 浜野洋輔, 和田直樹, 高橋 憲司
  • Organizer: 第67回高分子討論会
• [Remarks] 研究室ホームページ
  • URL: https://ktlabo.w3.kanazawa-u.ac.jp/
• [Remarks] 研究室ホームページ
  • URL: http://ktlabo.w3.kanazawa-u.ac.jp/Kenji_Takahashi_Labo/Welcome.html
• [Patent(Industrial Property Rights)] 多糖類エステル化物の製造方法 (2019)
  • Inventor(s): 廣瀨大祐 玄田雅志 和田直樹 瀧健太郎 高橋憲司 松村裕之
  • Industrial Property Rights Holder: 廣瀨大祐 玄田雅志 和田直樹 瀧健太郎 高橋憲司 松村裕之
  • Industrial Property Rights Type: 特許
  • Filing Date: 2019
  • Overseas
• [Patent(Industrial Property Rights)] 多糖類のシリルエーテル化物の製造方法 (2019)
  • Inventor(s): 廣瀬大祐 サムエル クスマ 和田直樹 高橋憲司 松村裕之
  • Industrial Property Rights Holder: 廣瀬大祐 サムエル クスマ 和田直樹 高橋憲司 松村裕之
  • Industrial Property Rights Type: 特許
  • Filing Date: 2019
  • Overseas
• [Patent(Industrial Property Rights)] 多糖類誘導体の製造方法、及びリグニン誘導体の製造方法 (2019)
  • Inventor(s): 廣瀬大祐, サムエル・クスマ, 丸山千恵, 和田直樹, 高橋憲司
  • Industrial Property Rights Holder: 金沢大学
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 2019-043063
  • Filing Date: 2019
• [Patent(Industrial Property Rights)] 多糖類誘導体の製造方法、及びリグニン誘導体の製造方法 (2019)
  • Inventor(s): 廣瀬大祐, サムエル・クスマ, 伊奈大希, 和田直樹, 高橋憲司
  • Industrial Property Rights Holder: 金沢大学
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 2019-042767
  • Filing Date: 2019
• [Patent(Industrial Property Rights)] リグノセルロース系バイオマス由来の複合材料及びその製造方法 (2018)
  • Inventor(s): 鈴木栞, ステファニー, 引田響, 浜野洋輔, 高橋憲司
  • Industrial Property Rights Holder: 金沢大学
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 2018-159416
  • Filing Date: 2018