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Selective Cleavage of Ether Bonds in Lignin by Trimethylsilyl Iodide

Research Project

Project/Area Number 01560177
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 林産学
Research InstitutionThe University of Tokyo

Principal Investigator

MESHITSUKA Gyosuke  The University of Tokyo, Faculty of Agriculture, Associate Prof., 農学部, 助教授 (30012074)

Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1990: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1989: ¥1,400,000 (Direct Cost: ¥1,400,000)
Keywordslignin / ether bonds / selective ether cleavage reaction / carbon-carbon bond / trimethylsilyl iodide / condensed structures / molecular weight distribution / 炭素-炭素結合
Research Abstract

Lignin is a kind of polymeric phenols composed of three different types of structural units, namely guaiacyl, syringyl and phydroxyphenyl units. Major bonding structures between structural units are ether and carbon-carbon bonds, and their distributions are quite characteristic depending on the origins of lignins in the cell wall. Therefore, the authors have been trying to see the contribution of carbon-carbon bonds in various lignin fractions by the selective cleavage of ether bonds. Trimethylsilyl iodide was found to be able to cleave so-called beta-ether bonds in a lignin model compound, guaiacylglycerol-beta-guaiacylether, almost quantitatively without noticeable side-reactions. The ether cleavage by this reagent was very successful also for an isolated lignin, milled wood lignin, if it is previously acetylated, and a milled wood lignin was totally converted to the chloroform soluble low molecular weight compounds. Although the exact molecular weight of the reaction products are not clear yet, most of them seems to be lower than 500 which is equivalent to dimer or trimer of structural units. In other words, most of lignin fraction is not connected by more than three successive carbon-carbon bond. We also applied this reagent to soda pulps prepared under different cooking conditions. It was found that lignin in a pulp was degraded by this reagent to the very low molecular weight compounds which was as low as the case of the original wood lignin. This was true even for the Pulp after a prolonged cooking. On the other hand, the dissolved lignins found to have remarkably condensed structures even at the beginning of the cooking. In other words, a dissolved lignin still keep a considerably high molecular weight after the treatment with this reagent. Furthermore, structural changes of the dissolved lignin was found to complete at the rather initial stage of cooking. These information is very useful to understand the structural changes of lignin during alkali-cooking.

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] Gyosuke Meshitsuka: "Cleavage of βーAryl Ether Bonds is Lignin by Trimethylsilyl Iodide" I.Wood Chem.Technol.7. 161-178 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Shigeto Makino: "Selective Cleavage of Ether Bonds in Lignin by Trimethylsilyl Iodide" Proceedings of 1989 International Symposium on Wood and Pulping Chemistry. 1. 275-278 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Shigeto Makino: "Selective Cleavage of Ether Bonds in Lignin by Trimethylsilyl Iodide" 木材学会誌. 36. 460-465 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenichi Fujino: "Formation of carbonーcarbon bonds in Lignin dnring Alkaline CookingーStudies by the use of trimethylsilyl Iodideー" 木材学会誌.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Shigeto MAKINO, Gyosuke MESHITSUKA, Atsushi ISHIZU: "Selective Cleavage of Ether Bonds in Lignin by Trimethylsilyl Iodide" Mokuzai Gakkaishi. 36. 460-465 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenichi Fujino, Gyosuke MESHITSUKA, Atsushi ISHIZU: "Formation of Carbon-Carbon Bonds in Lignin During Alkaline Cooking---Studies by the Use of Trimethylsilyl Iodide--"

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Gyosuke Meshitsuka: "Cleavage of βーAryl Ether Bonds is hignin by Trimethylsulyl Jodide" I.Wood Chem. Technol.7. 161-178 (1987)

    • Related Report
      1990 Annual Research Report
  • [Publications] Shigeto Makino: "Selective Cleavage of Ether Bonds in Lignin by Trimethylsilyl Jodide" Proceedings of 1989 Jnternational Eymposium on Wood and Pulping Chomistry. 1. 275-278 (1989)

    • Related Report
      1990 Annual Research Report
  • [Publications] Shigeto Makino: "Selective Cleavage of Ether Bonds in Lignin by Trimethylsilyl Jodide" 木材学会誌. 36. 460-465 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Kenichi Fujino: "Formation of carfonーcarfon fonds in Lignin dnring Alkaline CookingーStudies by the use of trimethylsilyl Jodideー" 木材学会誌.

    • Related Report
      1990 Annual Research Report
  • [Publications] Gyosuke Meshitsuka: "Cleavage of β-Aryl Ether Bonds in Lignin by Trimethylsilyl Iodide" J.Wood Chem.Technol.7. 161-178 (1987)

    • Related Report
      1989 Annual Research Report
  • [Publications] Shigeto Makino: "Selective Cleavage of Ether Bonds in Lignin by Trimethylsilyl Iodide" Proceedings of 1989. International Symposium on Wood and Pulping Chemistry. 275-278 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Shigeto Makino: "Selective Cleavage of Ether Bonds in Lignin by Trimethylsilyl Iodide" 木材学会誌.

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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