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Alkaline degradation of model compounds related to beech xylan

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Published/Copyright: June 1, 2005
Holzforschung
From the journal Volume 58 Issue 6

Abstract

To address the chemical behavior of beech xylan (O-acetyl-4-O-methyl-glucuronoxylan) under alkaline conditions, three model compounds, 2-O-methylxylobiose (1), aldobiouronic acid (4-O-methyl-α-D-glucopyranosyluronic acid-(1→2)-xylose, 2), and aldotriouronic acid (4-Omethyl-α-D-glucopyranosyluronic acid-(1→2)-β-D-xylopyranosyl-(1→4)-D-xylose, 3), were subjected to strong alkaline conditions equal to those used for the industrial production of viscose (18% NaOH, 43°C). Kinetics of the degradation of the model compounds were monitored by capillary electrophoresis in combination with pre-column derivatization. It was demonstrated that substitution at O-2 of the reducing xylose unit strongly retarded the alkaline degradation reactions (1 and 2). By isotopic labeling experiments and isolation of degradation products it was shown that under the pertinent conditions deprotonation at C-2 occurs, followed by epimerization to the respective lyxo derivative. Aldotriouronic acid 3 was degraded to 2 as an intermediate according to classical peeling pathways. Genuine degradation reactions and epimerization processes were distinguished.

Keywords: aldouronic acids; alkalization; beech xylan; capillary electrophoresis; epimerization; 2-O-methylxylobiose; peeling reaction
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Published Online: 2005-06-01
Published in Print: 2004-10-01

© Walter de Gruyter

Articles in the same Issue

  1. Subject Index
  2. Contents
  3. Species Index
  4. Author Index
  5. Monoethanolamine (MEA) pulping of beech and spruce wood for production of dissolving pulp
  6. Voltammetric analysis of the bleachability of softwood kraft pulps
  7. Alkaline degradation of model compounds related to beech xylan
  8. Effect of UV radiation on the carbonyl distribution in different pulps
  9. Changes in the lignin-carbohydrate complex in softwood kraft pulp during kraft and oxygen delignification
  10. Carbohydrate structures in residual lignin-carbohydrate complexes of spruce and pine pulp
  11. Ozonation of pine kraft lignin in alkaline solution. Part 1: Ozonation, characterization of kraft lignin and its ozonated preparations
  12. Ozonation of pine kraft lignin in alkaline solution. Part 2: Surface active properties of the ozonated kraft lignins
  13. Lignin reactions in oxygen delignification catalysed by Mn(II)-substituted molybdovanadophosphate polyanion
  14. Bioactive phenolic substances in industrially important tree species. Part 2: Knots and stemwood of fir species
  15. Evaluation of hydrocarbon emissions from heart- and sapwood of Scots pine using a laboratory-scale wood drier
  16. Effect of pulsating tension-torsion combined loading on fatigue behavior in wood
  17. Effects of density and microfibril orientation on the vertical variation of low-stiffness wood in radiata pine butt logs
  18. Determination of the natural durability of larch wood (Larix decidua Mill.) from the Western Italian Alps
  19. High-performance liquid chromatographic analysis of soluble and total oxalate in Ca- and Mg-amended liquid cultures of three wood decay fungi
  20. Artificial weathering of tropical woods. Part 1: Changes in wettability and Artificial weathering of tropical woods. Part II: Color change
https://doi.org/10.1515/HF.2004.112
Keywords for this article
aldouronic acids; alkalization; beech xylan; capillary electrophoresis; epimerization; 2-O-methylxylobiose; peeling reaction

Articles in the same Issue

  1. Subject Index
  2. Contents
  3. Species Index
  4. Author Index
  5. Monoethanolamine (MEA) pulping of beech and spruce wood for production of dissolving pulp
  6. Voltammetric analysis of the bleachability of softwood kraft pulps
  7. Alkaline degradation of model compounds related to beech xylan
  8. Effect of UV radiation on the carbonyl distribution in different pulps
  9. Changes in the lignin-carbohydrate complex in softwood kraft pulp during kraft and oxygen delignification
  10. Carbohydrate structures in residual lignin-carbohydrate complexes of spruce and pine pulp
  11. Ozonation of pine kraft lignin in alkaline solution. Part 1: Ozonation, characterization of kraft lignin and its ozonated preparations
  12. Ozonation of pine kraft lignin in alkaline solution. Part 2: Surface active properties of the ozonated kraft lignins
  13. Lignin reactions in oxygen delignification catalysed by Mn(II)-substituted molybdovanadophosphate polyanion
  14. Bioactive phenolic substances in industrially important tree species. Part 2: Knots and stemwood of fir species
  15. Evaluation of hydrocarbon emissions from heart- and sapwood of Scots pine using a laboratory-scale wood drier
  16. Effect of pulsating tension-torsion combined loading on fatigue behavior in wood
  17. Effects of density and microfibril orientation on the vertical variation of low-stiffness wood in radiata pine butt logs
  18. Determination of the natural durability of larch wood (Larix decidua Mill.) from the Western Italian Alps
  19. High-performance liquid chromatographic analysis of soluble and total oxalate in Ca- and Mg-amended liquid cultures of three wood decay fungi
  20. Artificial weathering of tropical woods. Part 1: Changes in wettability and Artificial weathering of tropical woods. Part II: Color change
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