Development of chemical recycling of plastics and biopolymers toward effective valorization

• Project/Area Number: 24241023
• Research Category: Grant-in-Aid for Scientific Research (A)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Environmental technology/Environmental materials
• Research Institution: Yamaguchi University
• Principal Investigator: Kamimura Akio 山口大学, 創成科学研究科, 教授 (30194971)
• Co-Investigator(Kenkyū-buntansha): 吉本 誠 山口大学, 医学系研究科, 准教授 (80322246)
• Research Collaborator: KATO Kazunari 山口大学, 大学院医学系研究科 ; IKEDA Kosuke 山口大学, 大学院医学系研究科 ; KAISO Kouji 宇部興産宇部研究所, 主任研究員 ; MATSUMOTO Hiroshi 宇部興産宇部研究所, 研究員 ; MURATA Kengo 山口大学, 大学院医学系研究科 ; TANIMURA Kazuhiko 山口大学, 大学院医学系研究科 ; MIHONO Kai 山口大学, 大学院医学系研究科
• Project Period (FY): 2012-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥44,590,000 (Direct Cost: ¥34,300,000、Indirect Cost: ¥10,290,000); Fiscal Year 2016: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000); Fiscal Year 2015: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000); Fiscal Year 2014: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000); Fiscal Year 2013: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000); Fiscal Year 2012: ¥29,120,000 (Direct Cost: ¥22,400,000、Indirect Cost: ¥6,720,000)
• Keywords: 解重合反応 / 高分子 / プラスチック / セルロース / 超臨界流体 / イオン液体 / リポソーム / セルラーゼ / ソルビトール

Outline of Final Research Achievements

Studies on depolymerization reaction of plastics and natural polymers toward efficient valorization were carried out. We investigated efficient depolymerization of polyamides in supercritical methanol. Kinetic studies on this reaction revealed whole reaction mechanism and substitution of amino group in the monomer took place through SN2 reaction with added carboxylic acid. This reaction was generally applied and many of simple amines were also converted into alcohols under the same conditions. Ionic liquids provided a new conversion of sorbitol to isosorbide in only 10 minutes by heating in a microwave oven. This reaction was efficiently catalyzed by catalytic amounts of acid and solid acid catalyst such as ion exchange resin was also useful. Cellulose was effectively converted into glucose in ionic liquids in the presence of liposomes including cellulase, which was effectively stabilized and maintained its chemical reactivity for the efficient conversion.

Research Products

• [Journal Article] Efficient depolymerization and chemical conversion of polyamide 66 to 1,6-hexanediol (2017)
  • Author(s): Hiroshi Matsumoto, Yugo Akinari, Kouji Kaiso, Akio Kamimura
  • Journal Title: J Mater. Cycles Waste Manag. Volume: 19 Issue: 1 Pages: 326-331
  • DOI: 10.1007/s10163-015-0425-4
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Modulation of cellulase activity by charged lipid bilayers with different acyl chain properties for efficient hydrolysis of ionic liquid-pretreated cellulose (2016)
  • Author(s): Kai Mihono, Takeshi Ohtsu, Mai Ohtani, Makoto Yoshimoto* and Akio Kamimura
  • Journal Title: Colloids Surf. B Volume: 146 Pages: 198-203
  • DOI: 10.1016/j.colsurfb.2016.06.005
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] An Efficient Conversion of Lysine to 2-Aminocaprolactam (2016)
  • Author(s): Hiroshi Matsumoto, Kouji Kaiso, and Akio Kamimura
  • Journal Title: Heterocycles Volume: 92 Pages: 337-345
  • NAID: 40020797015
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Efficient conversion of polyamides to omega-hydroxyalkanoic acids; a new method for chemical recycling of waste plastics (2014)
  • Author(s): Akio Kamimura,* Kosuke Ikeda, Shuzo Suzuki, Kazunari Kato, Yugo Akinari, Tsunemi Sugimoto, Kohichi Kashiwagi, Kouji Kaiso, Hiroshi Matsumoto, and Makoto Yoshimoto
  • Journal Title: ChemSusChem Volume: 7 Issue: 9 Pages: 2473-2477
  • DOI: 10.1002/cssc.201402125
  • Peer Reviewed
• [Journal Article] A Rapid Conversion of Sorbitol to Isosorbide in Hydrophobic Ionic Liquids under Microwave Irradiation (2014)
  • Author(s): Akio Kamimura,* Kengo Murata, Yoshiki Tanaka, Tomoki Okagawa, Hiroshi Matsumoto, Kouji Kaiso, and Makoto Yoshimoto
  • Journal Title: ChemSusChem Volume: 7 Issue: 12 Pages: 3257-3259
  • DOI: 10.1002/cssc.201402655
  • Peer Reviewed
• [Journal Article] Hydrolysis of insoluble cellulose to glucose catalyzed by cellulase-containing liposomes in an aqueous solution of 1-butyl-3-methylimidazolium chloride (2013)
  • Author(s): Makoto Yoshimoto, Kazuhiko Tanimura, Kazuki Tokunaga and Akio Kamimura
  • Journal Title: Biotechnol. Prog., Volume: 29 Issue: 5 Pages: 1190-1196
  • DOI: 10.1002/btpr.1779
  • Peer Reviewed
• [Journal Article] Combination use of hydrophobic ionic liquids and LiCl as a good reaction system for the chemical conversion of cellulose to glucose (2012)
  • Author(s): Akio Kamimura, Tomoki Okagawa, Natsumi Oyama, Tamami Otsuka and Makoto Yoshimoto
  • Journal Title: Green Chemistry Volume: 14 Issue: 10 Pages: 2816-2820
  • DOI: 10.1039/c2gc35811e
  • Peer Reviewed
• [Presentation] 超臨界メタノール中でのポリアミドの解重合反応の反応機構 (2017)
  • Author(s): ○上村明男・池田功介・松本紘・海磯孝二・吉本誠
  • Organizer: 日本化学会第97春季年会
  • Place of Presentation: 慶応大学日吉キャンパス（神奈川県横浜市）
  • Year and Date: 2017-03-16
• [Presentation] A Rapid Conversion of Sorbitol to Isosorbide in Hydrophobic Ionic Liquids (2016)
  • Author(s): Kengo Murata, Takuji Kawamoto and Akio Kamimura
  • Organizer: ISONIS10
  • Place of Presentation: 淡路夢舞台（兵庫県淡路市）
  • Year and Date: 2016-11-17
  • Int'l Joint Research
• [Presentation] ポリアミドのアップグレード化学リサイクルの反応速度的研究 (2016)
  • Author(s): 上村明男・池田功介・松本紘・海磯孝二・吉本誠
  • Organizer: FSRJ19回研究討論会
  • Place of Presentation: 九州工業大学（福岡県北九州市）
  • Year and Date: 2016-09-02
• [Presentation] A Green and rapid conversion of sorbitol to isosorbide in hydrophobic ionic liquids (2016)
  • Author(s): Akio Kamimura* and Kengo Murata
  • Organizer: 16th EUCHEM on molten salts and ionic liquids
  • Place of Presentation: Austria Trend Hotel Savoyen, Rennweg 16, 1030 Wien, Austria
  • Year and Date: 2016-07-03
  • Int'l Joint Research
• [Presentation] Hydrophobic ionic liquids as a new tool for biomass conversion (2016)
  • Author(s): Akio Kamimura and Kengo Murata
  • Organizer: French-Japanese Symposium on Medicinal and Fine Chemistry (FJS2016)
  • Place of Presentation: Keio Plaza Hotel Tama（東京都多摩市）
  • Year and Date: 2016-05-16
  • Int'l Joint Research
• [Presentation] 疎水性イオン液体を用いたソルビトールの高速脱水変換反応 (2016)
  • Author(s): 村田健虎・上村明男
  • Organizer: 第26回万有福岡シンポジウム
  • Place of Presentation: 九大百年記念会館 (福岡県福岡市）
  • Year and Date: 2016-04-23
• [Presentation] イオン液体共存下のリポソーム複合化セルラーゼ活性に及ぼす脂質膜疎水性領域の 影響 (2016)
  • Author(s): 三穂野海，大津豪志，大谷舞，吉本誠，上村明男
  • Organizer: 化学工学会第81年会
  • Place of Presentation: 関西大学（大阪府吹田市）
  • Year and Date: 2016-03-13
• [Presentation] Development of Green Conversions of Biomass in Hydrophobic Ionic liquids (2015)
  • Author(s): Akio Kamimura
  • Organizer: PACIFICHEM2015
  • Place of Presentation: Honolulu, USA
  • Year and Date: 2015-12-15
  • Int'l Joint Research / Invited
• [Presentation] Efficient Conversions of Plastics into Economically Valuable Products (2015)
  • Author(s): Akio Kamimura
  • Organizer: PACIFICHEM2015
  • Place of Presentation: Honolulu, USA
  • Year and Date: 2015-12-15
  • Int'l Joint Research / Invited
• [Presentation] 固体酸触媒を用いたイオン液体中でのソルビトールの高速変換反応 (2015)
  • Author(s): 上村明男・村田健虎・松本紘・海磯孝二
  • Organizer: イオン液体討論会
  • Place of Presentation: 同志社大学（京都市）
  • Year and Date: 2015-10-26
• [Presentation] 疎水性イオン液体を用いたソルビトールの高速脱水変換反応 (2015)
  • Author(s): 村田健虎・岡川大輝・田中佳季・松本紘・海磯孝二・吉本誠・上村明男
  • Organizer: 基礎有機化学討論会
  • Place of Presentation: 愛媛大学（愛媛県松山市）
  • Year and Date: 2015-09-24
• [Presentation] 荷電脂質膜内のセルラーゼを用いたイオン液体共存下における不溶性セルロース糖化反応 (2015)
  • Author(s): 三穂野 海, 大津 豪志, 吉本 誠, 上村 明男
  • Organizer: 化学工学会第47秋季大会
  • Place of Presentation: 北海道大学（北海道札幌市）
  • Year and Date: 2015-09-09
• [Presentation] An efficient conversion of polyamides to chemical feedstock (2015)
  • Author(s): Akio Kamimura, Hiroshi Matsumoto, Kosuke Ikeda and Kouji Kaiso
  • Organizer: ISFR2015
  • Place of Presentation: Leoben, Austria
  • Year and Date: 2015-09-07
  • Int'l Joint Research
• [Presentation] An Efficient Method for Chemical Recycling of Plastics (2015)
  • Author(s): Hiroshi Matsumoto, Kouji Kaiso, Makoto Yoshimoto, Akio Kamimura
  • Organizer: GSC7
  • Place of Presentation: 一橋ホール（東京都千代田区）
  • Year and Date: 2015-07-05
  • Int'l Joint Research
• [Presentation] セルラーゼ封入リポソームを用いたイオン液体共存下における不溶性セルロース糖化反応 (2014)
  • Author(s): 三穂野海，大津豪志，吉本誠，上村明男
  • Organizer: 化学工学会中国四国支部大学院生発表会
  • Place of Presentation: 広島市 RCC文化センター
  • Year and Date: 2014-12-05
• [Presentation] 新しい液体、イオン液体を使った有機合成の可能性－プラスチックとバイオマスの変換反応への研究例から考える－ (2014)
  • Author(s): 上村明男
  • Organizer: 有機合成化学協会九州山口支部第2回有機合成化学講演会
  • Place of Presentation: 宇部市 宇部興産宇部研究所
  • Year and Date: 2014-11-17
  • Invited
• [Presentation] イオン液体中でのプラスチックの熱分解 反応を用いた資源再利用法の開発 (2014)
  • Author(s): 田中佳季・上村明男
  • Organizer: 日本化学会中国四国支部大会
  • Place of Presentation: 山口市 山口大学
  • Year and Date: 2014-11-08 – 2014-11-09
• [Presentation] 疎水性イオン液体を用いたソルビトールの高効率変換反応 (2014)
  • Author(s): 上村 明男, 村田 健虎, 田中 佳季, 岡川大輝, 松本紘, 海磯孝二
  • Organizer: 第5回イオン液体討論会
  • Place of Presentation: 横浜市 横浜シンポジア
  • Year and Date: 2014-10-28 – 2014-10-29
• [Presentation] Conversion of Biomass Using Hydrophobic Ionic Liquids (2014)
  • Author(s): Akio Kamimura
  • Organizer: ASIL-6
  • Place of Presentation: Sydney, Australia
  • Year and Date: 2014-09-28 – 2014-10-01
• [Presentation] CONVERSION OF SORBITOL TO ISOSORBIDE IN HYDROPHOBIC IONIC LIQUIDS (2014)
  • Author(s): Akio Kamimura, Tomoki Okagawa, Hiroshi Matsumoto, Kouji Kaiso, Makoto Yoshimoto
  • Organizer: EUCHEM2014 25th Molten salts and Ionic Liquids
  • Place of Presentation: Tallinn, Estonia
  • Year and Date: 2014-07-06 – 2014-07-11
• [Presentation] ポリアミドのアップグレードケミカルリサイクルに向けた新規解重合反応 (2014)
  • Author(s): 松本 紘, 海磯 孝二, 上村 明男, 吉本 誠, 鈴木 秀三, 嘉藤 一成, 秋成 優吾
  • Organizer: 第3回 JACI/GSCシンポジウム
  • Place of Presentation: 東京都 東京国際フォーラム
  • Year and Date: 2014-05-22
• [Presentation] リポソームを用いる微小円管内せん断流中のグルコース酸化酵素の活性化 (2014)
  • Author(s): 夏目友誉，吉本誠
  • Organizer: 化学工学会第79年会
  • Place of Presentation: 岐阜大学/岐阜市
• [Presentation] 効率的化学リサイクルに向けたポリアミドの選択的な変換反応 (2014)
  • Author(s): 上村明男・池田功介・鈴木秀三・海磯孝二・松本紘・吉本誠
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 名古屋大学/名古屋市
• [Presentation] A new method for the conversion of cellulose to glucose using hydrophobic ionic liquids in the presence of LiCl (2013)
  • Author(s): Akio Kamimura, Makoto Yoshimoto
  • Organizer: 5th Congress on Ionic Liquids (COIL5)
  • Place of Presentation: Algarve, Portugal
• [Presentation] Use of Ionic liquids in Developing a New Method for Feedstock Recycling (2013)
  • Author(s): Akio Kamimura,* Shigehiro Yamamoto, Tomoki Okagawa, Tamami Otsuka and Makoto Yoshimoto
  • Organizer: 6th International Conference on Green and Sustainable Chemistry (GSC6)
  • Place of Presentation: Nottingham, UK
• [Presentation] DEPOLYMRIZATION OF POLYMERS IN IONIC LIQUIDS (2013)
  • Author(s): Akio Kamimura, Shigehiro Yamamoto, Tomoki Okagawa, Tamami Otsuka, Makoto Yoshimoto
  • Organizer: 7th International Symposium on Feedstock Recycling of Polymeric Materials (7th ISFR 2013)
  • Place of Presentation: New Delhi, India
• [Presentation] イオン液体とマイクロ波照射を用いたバイオマス等の変換反応 (2013)
  • Author(s): 上村明男・岡川大輝・田中佳季・海磯孝二・松本紘
  • Organizer: 第4回イオン液体討論会
  • Place of Presentation: 慶応大学/横浜市
• [Presentation] イオン液体を用いたソルビトールの変換反応 (2013)
  • Author(s): 岡川大輝・上村明男
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津市立命館大学
• [Presentation] イオン液体とマイクロ波照射を組み合わせたポリアミドの解重合反応 (2013)
  • Author(s): 大塚珠弥・上村明男
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津市立命館大学
• [Presentation] リポソーム内セルラーゼの安定性と不溶性セルロース糖化活性に及ぼすイオン液体の影響 (2013)
  • Author(s): 谷村和彦・)德永和輝・吉本誠・上村明男
  • Organizer: 化学工学会高松大会
  • Place of Presentation: 高松市サンポートホール高松
• [Presentation] Mechanistic studies for depolymerization of polyamides in supercritical MeOH (2012)
  • Author(s): Akio Kamimura,* Shuzo Suzuki, Kazunari Kato, Hiroshi Matsumoto and Kouji Kaiso
  • Organizer: The 21st IUPAC International Conference on Physical Organic Chemistry
  • Place of Presentation: Durham University, UK
• [Presentation] 超臨界アルコールを用いたポリアミドのアップグレードケミカルリサイクル (2012)
  • Author(s): 上村明男・海磯孝二・鈴木秀三・杉本常実・ 吉本誠
  • Organizer: プラスチックリサイクル化学研究会第15回討論会
  • Place of Presentation: 米沢市伝国の杜
• [Presentation] 疎水性イオン液体/塩化リチウムを用いたセルロースのグルコースへの変換反応 (2012)
  • Author(s): 上村明男、岡川大輝、大山奈津美、吉本誠
  • Organizer: 第3回イオン液体討論会
  • Place of Presentation: 那覇市沖縄県男女共同参画センター 「てぃるる」
• [Presentation] Toward developing new methods for chemical recycling of plastics: from use of ionic liquids to upgrading waste plastics
  • Author(s): Akio Kamimura
  • Organizer: Hamburg University Invited lecture
  • Place of Presentation: Hamburg University, Germany
  • Invited
• [Book] イオン液体研究最前線と社会実装 (2016)
  • Author(s): 上村明男・吉本誠
  • Total Pages: 335
  • Publisher: シーエムシー出版
• [Remarks]
  • URL: http://perkin.chem.yamaguchi-u.ac.jp/web_English/welcome/welcome.html
• [Remarks] スポットライト研究
  • URL: http://www.chem.yamaguchi-u.ac.jp/spotlight/kamimura.html
• [Remarks]
  • URL: http://perkin.chem.yamaguchi-u.ac.jp/
• [Remarks] イオン液体を用いた高分子の再資源化反応の開発
  • URL: http://perkin.chem.yamaguchi-u.ac.jp/
• [Remarks] 研究室HP
  • URL: http://perkin.chem.yamaguchi-u.ac.jp