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Characterization of cellouronic acid

Research Project

Project/Area Number 13660157
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 林産学
Research InstitutionTHE UNIVERSITY OF TOKYO

Principal Investigator

ISOGAI Akira  The University of Tokyo, Graduate School of Agricultural and Life Sciences, Associate Professor, 大学院・農学生命科学研究科, 助教授 (40191879)

Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2002: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2001: ¥2,600,000 (Direct Cost: ¥2,600,000)
KeywordsCellulose / TEMPO / Oxidation / Polyuronic acid / Functionalization / Gas barrier / Biodegradability / Hexenuronic acid / ヘキセンウロン / ラジカル捕捉剤 / アルデヒド基 / カルボキシル基
Research Abstract

Intermediate structures from regenerated cellulose to water-soluble β-1,4-linked polyglucuronic acid (cellouronic acid Na salt) by TEMPO-mediated oxidation were investigated in detail using water-soluble starch as a model compound, which was oxidized stepwise from 0 to 100% oxidation by means of NMR. The results revealed that a significant amount of C6 aldehyde groups was detected as intermediate structures, which consumed the corresponding NaOH. The maximum amount of C6 aldehyde was about 40%. Sufficient reagents or sufficient reaction time gave almost pure α-1,4-linked polyglucuronic acid from water-soluble starch by TEMPO-mediated oxidation.
The mechanism of depolymerization of cellulose during TEMPO-mediated oxidation was studied to control molecular weight of cellouronic acid prepared. The results indicate that hydroxyl radicals formed during the oxidation as by-products participate in the depolymerization. Some radical scavengers are effective in controlling depolymerization of ce … More llulose during the oxidation, when added to the medium. Cellouronic acid having higher molecular weight can be obtained by fractional precipitation of cellouronic acid/water solutions by gradual addition of methanol.
Commercial nitroxyl radicals other than TEMPO were applied to the cellulose oxidation to see the effects on chemical structures, yields and molecular weights of the obtained products. Some nitroxyl radicals allowed to reduce reaction time required for preparing cellouronic acid from cellulose, thus giving the oxidized products having higher molecular weight. However, complete control of depolymerization could not be achieved by any treatments examined so far.
TEMPO-mediated oxidation of native cellulose was investigated in detail. Although native cellulose cannot be converted to water-soluble cellouronic acid in high yields, some disordered regions undergo the oxidation to form water-soluble products. The maximum yields were ca. 20%. However, the water-insoluble residues still had the crystal structure of cellulose I, and thus oxidation to inside cellulose crystallites is difficult. Less

Report

(3 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • Research Products

    (21 results)

All Other

All Publications (21 results)

  • [Publications] Shibata, I., et al.: "Depolymerization of cellouronic acid during TEMPO-mediated oxidation"Cellulose. 10(印刷中). (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kato, Y., et al.: "Oxidation process of water-soluble starch in TEMPO-mediated system"Carbohydrate Polymers. 51(1). 69-75 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kato, Y., et al.: "Biodegradation of β-1,4-linked polyglucuronic acid (cellouronic acid)"Cellulose. 9. 75-81 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Shibata et al.: "β-1,4-Linked polyglucuronic acid prepared from cellulose by TEMPO-media oxidation"Proceedings of the 11^<th> ISWPC. Vol.2. 149-157 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 磯貝 明, 柴田 泉: "繊維学会誌・繊維と工業"TEMPO触媒酸化によるセルロースの化学改質. 57(6). 163-167 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 磯貝 明: "セルロースの材料科学"東京大学出版会. 182 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Shibata, I., Isogai, A.: "Depolymerization of cellouronic acid during TEMPO-mediated oxidation"Cellulose. 10, in press. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kato, Y., Matsuo, R., Isogai, A.: "Oxidation process of water-soluble starch in TEMPO-mediated system"Carbohydrate Polymers. 51. 69-75 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kato, Y., Isogai, A., et al.: "Biodegradation of β-1,4-linked polyglucuronic acid (cellouronic acid)"Cellulose. 9. 75-81 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Shibata, I., Isogai, A.: "β-1,4-Linked polyglucuronic acid prepared from cellulose by TEMPO-mediated oxidation"Proceedings of the 11^<th> ISWPC, Nice. 149-157 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Isogai, A., Shibata, I.: "Chemical modification of cellulose by TEMPO mediated oxidation"Journal of Japan Fiber Science Society. 57. 163-167 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Isogai, A.: "Material Science of Cellulose"Tokyo University Press. (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Shibata, I., et al.: "Depolymerization of cellouronic acid during TEMPO-mediated oxidation"Cellulose. 10(印刷中). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Kato, Y., et al.: "Oxidation process of water-soluble starch in TEMPO-mediated system"Carbohydrate Polymers. 51(1). 69-75 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Kato.Y., et al.: "Biodegradation of β-1,4-linked polyglucuronic acid (cellouronic acid)"Cellulose. 9. 75-81 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Shibata et al.: "β-1,4-Linked polyglucuronic acid prepared from cellulose by TEMPO-mediated oxidation"Proceedings of the 11^<th> ISWPC. Vol. 2. 149-157 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] 磯貝 明, 柴田 泉: "繊維学会誌・繊維と工業"TEMPO触媒酸化によるセルロースの化学改質. 57(6). 163-167 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] 磯貝 明: "セルロースの材料科学"東京大学出版会. 182 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Shibata, I., Ishogai, A., Onabe, F.: "β-1, 4-Linked polyglucuronic acid prepared from cellulose by TEMPO-mediated oxidation"Proceedings of 11th ISWPC. Vol.2. 149-152 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Kato, Y., Isogai, A., et al.: "Biodegradation of β-1, 4-linked polyglucuronic acid (cellouronic acid)"Cellulose. 8(印刷中). (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 磯貝明, 柴田泉: "TEMPO触媒酸化によるセルロースの化学改質"繊維学会誌. 57・6. 163-167 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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