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Removal of Phenolic Hydroxyl Groups in Lignin Model Compounds and Its Effect on Photostability

  • Thomas Q. Hu , Graham R. Cairns and Brian R. James
Published/Copyright: June 1, 2005
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Holzforschung
From the journal Volume 54 Issue 2

Summary

The phenolic hydroxyl groups in the lignin model compounds, 2-methoxy-4-propylphenol and 4-hydroxy-3-methoxyacetophenone, were removed by first converting the hydroxyl groups to the trifluoromethanesulfonates (triflates) and then cleaving the triflate substituents via catalytic hydrogen transfer. The products, 1-methoxy-3-propylbenzene and 3-methoxyacetophenone, were characterized by 1H and 13C NMR, mass spectrometry and elemental analyses. The effect of the removal of the phenolic groups on the photostability of the model compounds was evaluated by impregnating the compounds into Whatman filter paper sheets, and subjecting them to an accelerated yellowing experiment in a UV chamber. The removal of the phenolic groups resulted in a significant yellowing inhibition, with a higher photostabilizing effect than methylation or acetylation of the hydroxyl, particularly for the model compound without an α-carbonyl group.

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Published Online: 2005-06-01
Published in Print: 2000-02-29

Copyright © 2000 by Walter de Gruyter GmbH & Co. KG

Articles in the same Issue

  1. Modelling the Moisture Induced Risk of Decay for Treated and Untreated Wood Above Ground
  2. FTIR Characterization of Copper Ethanolamine—Wood Interaction for Wood Preservation
  3. Glycerol/Glyoxal: A New Boron Fixation System for Wood Preservation and Dimensional Stabilization
  4. Removal of Phenolic Hydroxyl Groups in Lignin Model Compounds and Its Effect on Photostability
  5. Cation Exchange Capacity Tests on Some Lignocellulosic Materials Highlight Some Aspects of the Use of Copper as Wood Preservative
  6. Biological, Chemical and Mechanical Characteristics of "Wulstholz" as a Response to Mechanical Stress in Living Trees of Picea abies [L.] Karst
  7. A Comparative Study on Reactions of Hydrogen Peroxide and Peracetic Acid with Lignin Chromophores. Part 1. The Reaction of Coniferaldehyde Model Compounds
  8. A Comparative Study on Reactions of Hydrogen Peroxide and Peracetic Acid with Lignin Chromophores. Part 2. The Reaction of Stilbene-Type Model Compounds
  9. Chlorinated Phenolic Compounds in Bleaching Filtrates from a Mixed Eucalyptus and Acacia Pulp Using Different Sequences
  10. Kinetic Studies on Oxidation of Veratryl Alcohol by Laccase-Mediator System. Part 1. Effects of Mediator Concentration
  11. Kinetic Studies on Oxidation of Veratryl Alcohol by Laccase-Mediator System. Part 2. The Kinetics of Dioxygen Uptake
  12. Determination of Residual Stresses in Medium Density Fibreboard
  13. Dynamics of Hardwood Impregnation
  14. Study of the System Wood – Coating Material. I. Wood – Liquid Coating Material
  15. Effect of Lignocellulosic Materials on the Properties of Thermoplastic Polymer/Wood Composites
  16. A New Air Dehydration Process for Wood Dryers. Part I. Kinetic and Quality of Drying
  17. A New Air Dehydration Process for Wood Dryers. Part II. Elimination of Organic Compounds
  18. A New Method of Sample Preparation for Kenaf Bast Fiber Length Analysis with Automated Fiber Length Analyzer
  19. Literature Reports
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