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2005 Fiscal Year Final Research Report Summary

Novel Sustainable chemical recycling of green polymers using environmentally benign catalytic process

Research Project

Project/Area Number 15350095
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Environmental chemistry
Research InstitutionKEIO UNIVERSITY

Principal Investigator

MATSUMURA Shuichi  Keio University, Faculty of Science and Technology, Professor, 理工学部, 教授 (30051874)

Co-Investigator(Kenkyū-buntansha) TOSHMA Kazunobu  Keio University, Faculty of Science and Technology, Professor, 理工学部, 教授 (60217502)
Project Period (FY) 2003 – 2005
KeywordsEnzyme / Chemical recycling / Cyclic oligomer / Poly(lactic acid) / Lipase / Polymerizable oligomer / Solid acid / Biopolyester
Research Abstract

In this study, sustainable chemical recycling of biodegradable poly(lactic acid) and bio-based polymers, which were produced from renewable resources, were developed using environmentally benign catalysts, such as enzymes and solid acids. Also, enzyme-catalyzed synthesis and chemical recycling of biopolythioesters were also studied. Summaries of the results are as follows.
(1)Transformation of bio-based polymers into repolymerizable cyclic oligomers
Enzyme-catalyzed cyclic oligomerization of poly(butylene adipate) was studied with respect to the basic reaction parameters. It was found that in certain organic solvents cyclic oligomerization was quickly occurred by lipase. The affinities toward lipase as well as the molecular weight of the repolymerization products were significantly influenced by the cyclic oligomer size.
(2)Developing of novel chemical recycling of poly(L-lactic acid) using solid acid
It was found that poly(L-lactic acid) was efficiently degraded into oligomers by montmorillonite. The obtained lactic acid oligomer was readily repolymerized by solid state polymerization to regenerate the polylactic acid with a molecular weight of greater than 100,000. Based on these results, sustainable chemical recycling of bio-based polymers was proposed.
(3)Novel enzymatic synthesis and properties of polythioesters
It was first found that mercaptocarboxylic acid was readily polymerized by enzyme to produce polythioester with a molecular weight of several ten thousands. Thus produced polythioester showed a higher melting temperature and resistance against organic solvents comparing to those of the corresponding polyoxyesters. Also, a series of polythioesters were produced by the polycondensation of alkanedithiol with alkanedicarobxylic acid, and their chemical recycling was established using an enzyme.

  • Research Products

    (58 results)

All 2006 2005 2004 2003

All Journal Article (48 results) Book (8 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Perspectives for synthesis and production of polyurethanes and related polymers by enzymes directed towards green and sustainable chemistry2006

    • Author(s)
      S.Matsumura
    • Journal Title

      Applied Microbiology and Biotechnology 70・1

      Pages: 12-20

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] New strategy for enzymatic synthesis of high-molecular-weight poly(butylene succinate) via cyclic oligomers2006

    • Author(s)
      S.Sugihara
    • Journal Title

      Macromolecular Rapid Communications 27・3

      Pages: 203-207

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enzymatic synthesis of polyesters via ring-opening polymerization2006

    • Author(s)
      S.Matsumura
    • Journal Title

      Advanced Polymer Science 194

      Pages: 95-132

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enzymatic transformation of aliphatic polyesters into cyclic oligomers using enzyme packed column under continuous flow of supercritical carbon dioxide with toluene2006

    • Author(s)
      Y.Osanai
    • Journal Title

      Science and Technology of Advanced Materials 7・

      Pages: 202-208

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Perspectives for Synthesis and Production of Polyurethanes and Related Polymers by Enzymes Directed Towards Green and Sustainable Chemistry2006

    • Author(s)
      S.Matsumura, Y.Soeda, K.Toshima
    • Journal Title

      Applied Microbiology and Biotechnology 70

      Pages: 12-20

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] New Strategy for Enzymatic Synthesis of High-Molecular-Weight Poly(butylene succinate) via Cyclic Oligomers2006

    • Author(s)
      S.Sugihara, K.Toshima, S.Matsumura
    • Journal Title

      Macromolecular Rapid Communications 27

      Pages: 203-207

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enzymatic Synthesis of Polyesters via Ring-Opening Polymerization2006

    • Author(s)
      S.Matsumura
    • Journal Title

      Advanced Polymer Science 194

      Pages: 95-132

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enzymatic transformation of Aliphatic Polyesters into Cyclic Oligomers Using Enzyme packed column under continuous flow of Supercritical Carbon Dioxide with Toluene2006

    • Author(s)
      Y.Osanai
    • Journal Title

      Science and Technology of Advanced Materials 7

      Pages: 202-208

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enzymatic synthesis and chemical recycling of poly(ester-urethane2005

    • Author(s)
      Y.Soeda
    • Journal Title

      Macromolecular Bioscience 5・4

      Pages: 277-288

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Degradation of poly(lactic acid) into repolymerizable oligomer using montmorillonite K10 for chemical recycling2005

    • Author(s)
      K.Okamoto
    • Journal Title

      Macromolecular Bioscience 5・9

      Pages: 813-820

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enzymatic transformation of bacterial polyhydroxyalkanoates into repolymerizable oligomers directed towards chemical recycling2005

    • Author(s)
      S.Kaihara
    • Journal Title

      Macromolecular Bioscience 5・7

      Pages: 644-652

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Preparation of aliphatic poly(thioester) by the lipase-catalyzed direct polycondensation of 11-mercaptoundecanoic acid2005

    • Author(s)
      M.Kato
    • Journal Title

      Biomacromolecules 6・4

      Pages: 2275-2280

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Environmentally benign β-stereoselective glycosidations of glycosyl phosphites using a reusable heterogeneous solid acid, montmorillonite K-102005

    • Author(s)
      H.Nagai
    • Journal Title

      Carbohydrate Research 430

      Pages: 337-353

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] グリーンポリマーの合成とケミカルリサイクル2005

    • Author(s)
      松村秀一
    • Journal Title

      ケミカルエンジニヤリング 50・10

      Pages: 771-778

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 固体酸を用いるポリ乳酸のケミカルリサイクル2005

    • Author(s)
      松村秀一
    • Journal Title

      ファインケミカル 34・8

      Pages: 20-28

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 酵素法によるグリーンポリマーのリサイクル2005

    • Author(s)
      松村秀一
    • Journal Title

      バイオサイエンスとインダストリー 63・8

      Pages: 48-51

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 酵素法によるグリーンプラスチックの創成2005

    • Author(s)
      松村秀一
    • Journal Title

      バイオインダストリー 22・7

      Pages: 51-60

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 次世代型グリーンポリウレタン-酵素触媒による生分解性ポリ(カーボネート-ウレタン)およびポリ(エステル-ウレタン)の合成とケミカルリサイクル2005

    • Author(s)
      添田泰之
    • Journal Title

      高分子加工 154・3

      Pages: 29-35

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enzymatic Synthesis and Chemical Recycling of Poly(ester-urethane)2005

    • Author(s)
      Y.Soeda, K.Toshima, S.Matsumura
    • Journal Title

      Macromolecular Bioscience 5(4)

      Pages: 277-288

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Degradation of Poly(lactic acid) into Repolymerizable Oligomer using Montmorillonite K10 for Chemical Recycling2005

    • Author(s)
      K.Okambto, K.Toshima, S.Matsumura
    • Journal Title

      Macromolecular Bioscience 5(9)

      Pages: 813-820

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enzymatic Transformation of Bacterial Polyhydroxyalkanoates into Repolymerizable Oligomers Directed towards Chemical Recycling2005

    • Author(s)
      S.Kaihara, Y.Osanai, K.Nishikawa, K.Toshima, Y.Doi, S.Matsumura
    • Journal Title

      Macromolecular Bioscience 5(7)

      Pages: 644-652

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Preparation of Aliphatic Poly(thioester) by the Lipase-Catalyzed Direct Polycondensation of 11-Mercaptoundecanoic Acid2005

    • Author(s)
      M, Kato, K.Toshima, S.Matsumura
    • Journal Title

      Biomacromolecules 6(4)

      Pages: 2275-2280

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Environmentally Benign β-Stereoselective Glycosidations of Glycosyl Phosphites Using a Reusable Heterogeneous Solid Acid, Montmorillonite K-102005

    • Author(s)
      H.Nagai, K.Sasaki, S.Matsumura, K.Toshima
    • Journal Title

      Carbohydrate Research 430

      Pages: 337-353

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis and Chemical Recycling of Green Polymer (Japanese)2005

    • Author(s)
      S.Matsumura
    • Journal Title

      Chemical Engineering 50(10)

      Pages: 771-778

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Chemical recycling of Poly(lactic acid) Using Solid Acid (Japanese)2005

    • Author(s)
      S.Matsumura, K.Okamoto, K.Toshima
    • Journal Title

      Fine Chemicals 34(8)

      Pages: 20-28

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Recycling of Green Polymers using Enzyme (Japanese)2005

    • Author(s)
      S.Matsumura
    • Journal Title

      Bioscience and Industry 63(8)

      Pages: 48-51

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Creation of Green Plastic using an Enzyme (Japanese)2005

    • Author(s)
      S.Matsumura
    • Journal Title

      Bio Industry 22(7)

      Pages: 51-60

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Next Generation-type Green Polyurethane : Enzymatic Synthesis and Chemical Recycling of Poly(ester-urethane) and Poly(ester-urethane)(Japanese)2005

    • Author(s)
      Y.Soeda, K.Toshima, S.Matsumura
    • Journal Title

      Polymer Applications 54(3)

      Pages: 29-35

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Lipase-catalyzed transformation of poly(lactic acid) into cyclic oligomer2004

    • Author(s)
      Y.Takahashi
    • Journal Title

      Macromolecular Bioscience 4・3

      Pages: 346-353

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α-nad β-manno-and 2-deoxyglucopyranosides2004

    • Author(s)
      K.Toshima
    • Journal Title

      Tetrahedron 60・6

      Pages: 5331-5339

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enzymatic synthesis and chemical recycling of poly(carbonate-urethane)2004

    • Author(s)
      Y.Soeda
    • Journal Title

      Macromolecular Bioscience 4・8

      Pages: 721-728

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity2004

    • Author(s)
      K.Sasaki
    • Journal Title

      Tetrahedron Letters 45・9

      Pages: 7043-7047

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Transformation of biodegradable polyesters into cyclic oligomers under continuous flow using an enzyme-packed column2004

    • Author(s)
      Y.Osana
    • Journal Title

      Macromolecular Bioscience 4・10

      Pages: 936-942

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Lipase-Catalyzed Transformation of Poly(lactic acid) into Cyclic Oligomer2004

    • Author(s)
      Y.Takahashi, S.Okajima, K.Toshima, S.Matsumura
    • Journal Title

      Macromolecular Bioscience 4(3)

      Pages: 346-353

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides2004

    • Author(s)
      K.Toshima, H.Nagai, K.Kasumi, K.Kawahara, S.Matsumura
    • Journal Title

      Tetrahedron 60(6)

      Pages: 5331-5339

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enzymatic Synthesis and Chemical Recycling of Poly(carbonate- urethane)2004

    • Author(s)
      Y.Soeda, K.Toshima, S.Matsumura
    • Journal Title

      Macromolecular Bioscience 4(8)

      Pages: 721-728

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity2004

    • Author(s)
      K.Sasaki, S.Matsumura, K.Toshima
    • Journal Title

      Tetrahedron Letters 45

      Pages: 7043-7047

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Transformation of Biodegradable Polyesters into Cyclic Oligomers under Continuous Flow Using an Enzyme-Packed Column2004

    • Author(s)
      Y.Osanai, K.Toshima, S.Matsumura
    • Journal Title

      Macromolecular Bioscience 4(10)

      Pages: 936-942

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Lipase-catalyzed transformation of poly(butylene adipate) and poly(butylene succinate) into repolymerizable cyclic oligomers2003

    • Author(s)
      S.Okajima
    • Journal Title

      Biomacromolecules 4・6

      Pages: 196-203

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enzymatic degradation of poly(3-hydroxybutylate) to cyclic oligomers under continuous flow2003

    • Author(s)
      Y.Osanai
    • Journal Title

      Green Chemistry 5・5

      Pages: 567-570

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enzyme-catalyzed preparation of aliphatic polyesters containing thioester linkages2003

    • Author(s)
      S.Iwata
    • Journal Title

      Macromolecular Rapid Communications 24・7

      Pages: 467-471

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Environmentally benign and stereoselsctive formation of β-mannosidic linkages utilizing 2,3-di-O-benzyl-4,6-O-benzylidene-protected mannopyrannosyl phosphate and montmorillonite K102003

    • Author(s)
      H.Nagai
    • Journal Title

      Carbohydrate Research 338・15

      Pages: 1531-1534

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A novel greener glycosidation using an acid-ionic liquid containing a protic acid2003

    • Author(s)
      K.Sasaki
    • Journal Title

      Tetrahedron Letters 44・30

      Pages: 5605-5608

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Lipase- Catalyzed Transformation of Poly(butylene adipate) and Poly(butylene succinate) into Repolymerizable Cyclic Oligomers2003

    • Author(s)
      S.Okajima, R.Kondo, K.Toshima, S.Matsumura
    • Journal Title

      Biomacromolecules 4(6)

      Pages: 1514-1519

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enzymatic Degradation of Poly(3-hydroxybutyrate) to Cyclic Oligomers under Continuous Flow2003

    • Author(s)
      Y.Osanai, K.Toshima, S.Matsumura
    • Journal Title

      Green Chemistry 5(5)

      Pages: 567-570

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enzyme-Catalyzed Preparation of Aliphatic Polyesters Containing Thioester Linkages2003

    • Author(s)
      S.Iwata, K.Toshima, S.Matsumura
    • Journal Title

      Macromolecular Rapid Communications 24(7)

      Pages: 467-471

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Environmentally benign and stereoselective formation of β-mannosidic linkages utilizing 2,3-di-O-benzyl-4,6-O-benzylidene-protected mannopyranosyl phosphite and montmorillonite K-102003

    • Author(s)
      H.Nagai, S.Matsumura, K.Toshima
    • Journal Title

      Carbohydrate Research 338(15)

      Pages: 1531-1534

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] A novel greener glycosidation using an acid-ionic liquid containing a protic acid2003

    • Author(s)
      K.Sasaki, H.Nagai, S.Matsumura, K.Toshima
    • Journal Title

      Tetrahedron Letters 44(30)

      Pages: 5605-5608

    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] Biodegradable polymeric materials and their applications2005

    • Author(s)
      S.Matsumura
    • Total Pages
      36
    • Publisher
      American Scientific Publishers
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] Biodegradable Polymers for Industrial Applications2005

    • Author(s)
      S.Matsumura
    • Total Pages
      53
    • Publisher
      Woodhead Publishing Limited
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] Enzymatic Synthesis and Chemical Recycling of Green Polymers, Biodegradable Polymeric Materials and their Applications (edited by S.Mallapragada and B.Narasimhan) Volume 12005

    • Author(s)
      S.Matsumura, Y.Osanai, Y.Soeda, Y.Suzuki, K.Toshima
    • Total Pages
      239-275
    • Publisher
      American Scientific Publishers, California, USA
    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] Mechanism of Biodegradation, Biodegradable Polymers for Industrial Applications (edited by R.Smith, Woodheal)2005

    • Author(s)
      S.Matsumura
    • Total Pages
      357-410
    • Publisher
      Publishing Limited, Cambridge, England
    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] 脱石油素材化に向けた生分解性プラスチックの高機能化とその応用2003

    • Author(s)
      松村秀一
    • Total Pages
      36
    • Publisher
      エヌ・アイー・エス
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] 生命科学への招待2003

    • Author(s)
      松村秀一
    • Total Pages
      11
    • Publisher
      三共出版
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] Plastic Recycling Using an Enzyme and its Application to Biodegradable Plastics (Japanese), Functionalization and application of biodegradable plastics to wards non-petroleum resources2003

    • Author(s)
      S.Matsumura
    • Total Pages
      237-274
    • Publisher
      NTS
    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] Biodegradable plastic that enable to the sustainable chemical recycling using an enzyme (Japanese), Introduction to life science (edited by H.Ohta and H.Yanagawa)2003

    • Author(s)
      S.Matsumura
    • Total Pages
      108-118
    • Publisher
      Sankyo Shuppan
    • Description
      「研究成果報告書概要(欧文)」より
  • [Patent(Industrial Property Rights)] 特許2004

    • Inventor(s)
      松村秀一, 添田泰之
    • Industrial Property Rights Holder
      慶應義塾
    • Industrial Property Number
      特願 2004-43924
    • Filing Date
      2004-08-24
    • Description
      「研究成果報告書概要(和文)」より
  • [Patent(Industrial Property Rights)] 特許2004

    • Inventor(s)
      松村秀一
    • Industrial Property Rights Holder
      慶應義塾
    • Industrial Property Number
      特願2004-133594
    • Filing Date
      2004-04-28
    • Description
      「研究成果報告書概要(和文)」より

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Published: 2007-12-13  

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