Home Physical Sciences Synthesis of a lignin polymer model consisting of only phenolic β-O-4 linkages and testing its reactivity under alkaline conditions 10th EWLP, Stockholm, Sweden, August 25–28, 2008
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Synthesis of a lignin polymer model consisting of only phenolic β-O-4 linkages and testing its reactivity under alkaline conditions 10th EWLP, Stockholm, Sweden, August 25–28, 2008

  • Jackson D. Megiatto , Emmanuel Cazeils , Stéphane Grelier , Christian Gardrat , Frédérique Ham-Pichavant and Alain Castellan
Published/Copyright: November 15, 2009
Holzforschung
From the journal Volume 63 Issue 6

Abstract

A trimeric β-O-4 lignin model bearing a styrene unit was polymerized in the presence of azobisisobutyronitrile as an initiator of free radical polymerization. The polymer analysis achieved by size exclusion chromatography (SEC), 1H, 13C, 31P NMR, matrix-assisted laser desorption ionization combined with time-of-flight mass spectrometry (MALDI-ToF MS), differential scanning calorimetry, and thermogravimetry indicated its well-defined structure with good thermal stability at temperatures usually applied for alkaline pulping. SEC analysis proved a high degree of polymerization despite the size of the phenolic β-O-4 units in the polymer structure. MALDI-ToF spectrometry indicated that the polymer is composed of phenolic β-O-4 elements only. The chemical reactivity under alkaline conditions of the polymer was studied by both HPLC and 31P NMR. These two methods revealed two main concurrent processes, which include an oxidation of the phenol part followed by Cα-Cβ bond cleavage, and a formation of a quinone methide followed by its β-O-4 bond cleavage.

Keywords: alkaline reactivity; lignin model; phenolic β-O-4 unit; polymer; synthesis
Corresponding author. Université Bordeaux 1, Unité Sciences du Bois et des Biopolymères, UMR UBx1-CNRS-INRA, F33405 Talence Cedex, France Phone: +33-5-4000-6280 Fax: +33-5-4000-6439
Received: 2008-11-3
Accepted: 2008-12-11
Published Online: 2009-11-15
Published Online: 2009-07-24
Published in Print: 2009-11-01

©2009 by Walter de Gruyter Berlin New York

Articles in the same Issue

  1. Original Papers
  2. Effects of selected key chromophores on cellulose integrity upon bleaching 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  3. A novel, mild and selective methylation of carboxyl groups in cellulosic pulps 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  4. Effect of salts on the formation and properties of microcrystalline cellulose and chitosan gels 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  5. Detection of muconic acid type structures in oxidised lignins using 2D NMR spectroscopy 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  6. Synthesis of a lignin polymer model consisting of only phenolic β-O-4 linkages and testing its reactivity under alkaline conditions 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  7. HSQC-NMR analysis of lignin in woody (Eucalyptus globulus and Picea abies) and non-woody (Agave sisalana) ball-milled plant materials at the gel state 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  8. Syringyl-type simple plant phenolics as mediating oxidants in laccase catalyzed degradation of lignocellulosic materials: Model compound studies 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  9. Titration of free phenolic groups in pulps 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  10. Interfacial properties of polyelectrolyte complexes incorporating kraft lignin 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  11. Comparing soluble Trametes pubescens laccase and cross-linked enzyme crystals (CLECs) for enzymatic modification of cellulose 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  12. Exploring enzymatic treatments for the production of dissolving grade pulp from different wood and non-wood paper grade pulps 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  13. Effects of commercial cellobiohydrolase treatment on fiber strength and morphology of bleached hardwood pulp 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  14. Prehydrolysis of Eucalyptus globulus Labill. hemicelluloses prior to pulping and fermentation of the hydrolysates with the yeast Pichia stipitis 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  15. Activation of thermomechanical pulp by laccases as studied by UV-Vis, UV resonance Raman and FTIR spectroscopy 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  16. Biological control of sapstain fungi: From laboratory experiments to field trials 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  17. Study of the sorption-desorption properties of pine wood at the initial stage of decay by wood-rot fungi 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  18. Decay susceptibility of Amazon wood species from Brazil against white rot and brown rot decay fungi 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  19. Relations between chemical changes and mechanical properties of thermally treated wood 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  20. Kinetics of SO2-ethanol-water pulping of spruce 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  21. Study on desorption of Mn, Fe, and Mg from TMP and evaluation of the complexing strength of different chelating agents using side reaction coefficients 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  22. Short Note
  23. Determination of self-diffusion coefficient and hydrodynamic radius of xylan by NMR diffusometry (NMRd) 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  24. Meetings
  25. Meetings
  26. Contents Volume 63
  27. Contents Volume 63 (2009)
  28. Subject index
  29. Subject index
  30. Species index (scientific names)
  31. Species index (scientific names)
  32. Author index
  33. Author index
  34. Acknowledgement
  35. Acknowledgement
https://doi.org/10.1515/HF.2009.056
Keywords for this article
alkaline reactivity; lignin model; phenolic β-O-4 unit; polymer; synthesis

Articles in the same Issue

  1. Original Papers
  2. Effects of selected key chromophores on cellulose integrity upon bleaching 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  3. A novel, mild and selective methylation of carboxyl groups in cellulosic pulps 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  4. Effect of salts on the formation and properties of microcrystalline cellulose and chitosan gels 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  5. Detection of muconic acid type structures in oxidised lignins using 2D NMR spectroscopy 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  6. Synthesis of a lignin polymer model consisting of only phenolic β-O-4 linkages and testing its reactivity under alkaline conditions 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  7. HSQC-NMR analysis of lignin in woody (Eucalyptus globulus and Picea abies) and non-woody (Agave sisalana) ball-milled plant materials at the gel state 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  8. Syringyl-type simple plant phenolics as mediating oxidants in laccase catalyzed degradation of lignocellulosic materials: Model compound studies 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  9. Titration of free phenolic groups in pulps 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  10. Interfacial properties of polyelectrolyte complexes incorporating kraft lignin 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  11. Comparing soluble Trametes pubescens laccase and cross-linked enzyme crystals (CLECs) for enzymatic modification of cellulose 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  12. Exploring enzymatic treatments for the production of dissolving grade pulp from different wood and non-wood paper grade pulps 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  13. Effects of commercial cellobiohydrolase treatment on fiber strength and morphology of bleached hardwood pulp 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  14. Prehydrolysis of Eucalyptus globulus Labill. hemicelluloses prior to pulping and fermentation of the hydrolysates with the yeast Pichia stipitis 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  15. Activation of thermomechanical pulp by laccases as studied by UV-Vis, UV resonance Raman and FTIR spectroscopy 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  16. Biological control of sapstain fungi: From laboratory experiments to field trials 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  17. Study of the sorption-desorption properties of pine wood at the initial stage of decay by wood-rot fungi 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  18. Decay susceptibility of Amazon wood species from Brazil against white rot and brown rot decay fungi 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  19. Relations between chemical changes and mechanical properties of thermally treated wood 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  20. Kinetics of SO2-ethanol-water pulping of spruce 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  21. Study on desorption of Mn, Fe, and Mg from TMP and evaluation of the complexing strength of different chelating agents using side reaction coefficients 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  22. Short Note
  23. Determination of self-diffusion coefficient and hydrodynamic radius of xylan by NMR diffusometry (NMRd) 10th EWLP, Stockholm, Sweden, August 25–28, 2008
  24. Meetings
  25. Meetings
  26. Contents Volume 63
  27. Contents Volume 63 (2009)
  28. Subject index
  29. Subject index
  30. Species index (scientific names)
  31. Species index (scientific names)
  32. Author index
  33. Author index
  34. Acknowledgement
  35. Acknowledgement
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