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Delignification Mechanism during High-Boiling Solvent Pulping. Part 1. Reaction of Guaiacylglycerol-β-Guaiacyl Ether

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Published/Copyright: June 1, 2005
Holzforschung
From the journal Volume 55 Issue 6

Summary

A phenolic β-O-4 type lignin model compound, guaiacylglycerol-β-guaiacyl ether (1) was treated with 70 wt% aq 1,3-butanediol solution at 160–200°C to investigate the delignification mechanism under HBS (high-boiling solvent) pulping conditions. The following compounds were identified from the reaction products by use of GC-MS: guaiacol (2), coniferyl alcohol (3), γ-etherified coniferyl alcohols (4) and α-etherified guaiacylglycerol-β-guaiacyl ethers (5), but acidolysis products, such as Hibbert's ketones were not detected. These results strongly suggest that the phenolic β-O-4 linkage was cleaved homolytically under HBS pulping conditions. The cleavage of β-ether exhibited a pseudo first-order rate behavior. The pseudo first-order rate constants were as follows: k = 0.94 × 10−2 min−1 at 160 °C; k = 1.97 × 10−2 min−1 at 170°C; k = 3.22 × 10−2 min−1 at 180 °C; k = 9.76 x 10−2 min−1 at 200 °C. The activation energy was 98.3 kJmol−1. The formation of higher molecular weight compounds was confirmed by GPC. It is highly probable that the oligomeric products were derived from the recombination of phenoxy radicals formed by homolysis of the β-aryl ether.

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Published Online: 2005-06-01
Published in Print: 2001-11-06

Copyright © 2001 by Walter de Gruyter GmbH & Co. KG

Articles in the same Issue

  1. Application of Scanning UV Microspectrophotometry to Localise Lignins and Phenolic Extractives in Plant Cell Walls
  2. Fungicidal Activity of 3'-Substituted-3-Stilbenols
  3. Characterisation of a Soft Rot-Like Decay Pattern Caused by Coniophora puteana (Schum.) Karst. in Sapelli Wood (Entandrophragma cylindricum Sprague)
  4. Transformation of Chlorophenols by White-Rot Fungi and their Laccase
  5. Fixation of Amine Copper Preservatives. Part 1. Reaction of Vanillin, a Lignin Model Compound with Monoethanolamine Copper Sulphate Solution
  6. Influence of Moisture Sorption on Swelling of Mahogany (Swietenia macrophylla King) Wood
  7. Silica in Several Rattan Species
  8. Changes in the Properties of Light-Irradiated Wood with Heat Treatment. Part 1. Effect of Treatment Conditions on the Change in Color
  9. Evaluating Strength Properties of Pinus radiata from Ultrasonic Measurements on Increment Cores
  10. Delignification Mechanism during High-Boiling Solvent Pulping. Part 1. Reaction of Guaiacylglycerol-β-Guaiacyl Ether
  11. Liquefaction Mechanism of β-O-4 Lignin Model Compound in the Presence of Phenol under Acid Catalysis. Part 1. Identification of the Reaction Products
  12. Liquefaction Mechanism of β-O-4 Lignin Model Compound in the Presence of Phenol under Acid Catalysis. Part 2. Reaction Behaviour and Pathways
  13. Study of Residual Lignin in Pulp by UV Resonance Raman Spectroscopy
  14. The Importance of Xylan for the Strength Properties of Spruce Kraft Pulp Fibres
  15. Eucalyptus globulus Kraft Pulp Residual Lignin. Part 2. Modification of Residual Lignin Structure in Oxygen Bleaching
  16. Monitoring Acoustic Emissions from Finger-Joints from Tropical African Hardwoods for Predicting Ultimate Tensile Strength
  17. Hydrolytic Processes and Condensation Reactions in the Cellulose Solvent System N,N-Dimethylacetamide/Lithium Chloride. Part 1.
  18. Viscoelastic Properties of Liquefied Wood/Epoxy Resin and its Bond Strength
  19. Prof. Dr. Josef Bauch 65 years old
  20. In Memory of Prof. Guglielmo Giordano
  21. Literature Reports
https://doi.org/10.1515/HF.2001.100

Articles in the same Issue

  1. Application of Scanning UV Microspectrophotometry to Localise Lignins and Phenolic Extractives in Plant Cell Walls
  2. Fungicidal Activity of 3'-Substituted-3-Stilbenols
  3. Characterisation of a Soft Rot-Like Decay Pattern Caused by Coniophora puteana (Schum.) Karst. in Sapelli Wood (Entandrophragma cylindricum Sprague)
  4. Transformation of Chlorophenols by White-Rot Fungi and their Laccase
  5. Fixation of Amine Copper Preservatives. Part 1. Reaction of Vanillin, a Lignin Model Compound with Monoethanolamine Copper Sulphate Solution
  6. Influence of Moisture Sorption on Swelling of Mahogany (Swietenia macrophylla King) Wood
  7. Silica in Several Rattan Species
  8. Changes in the Properties of Light-Irradiated Wood with Heat Treatment. Part 1. Effect of Treatment Conditions on the Change in Color
  9. Evaluating Strength Properties of Pinus radiata from Ultrasonic Measurements on Increment Cores
  10. Delignification Mechanism during High-Boiling Solvent Pulping. Part 1. Reaction of Guaiacylglycerol-β-Guaiacyl Ether
  11. Liquefaction Mechanism of β-O-4 Lignin Model Compound in the Presence of Phenol under Acid Catalysis. Part 1. Identification of the Reaction Products
  12. Liquefaction Mechanism of β-O-4 Lignin Model Compound in the Presence of Phenol under Acid Catalysis. Part 2. Reaction Behaviour and Pathways
  13. Study of Residual Lignin in Pulp by UV Resonance Raman Spectroscopy
  14. The Importance of Xylan for the Strength Properties of Spruce Kraft Pulp Fibres
  15. Eucalyptus globulus Kraft Pulp Residual Lignin. Part 2. Modification of Residual Lignin Structure in Oxygen Bleaching
  16. Monitoring Acoustic Emissions from Finger-Joints from Tropical African Hardwoods for Predicting Ultimate Tensile Strength
  17. Hydrolytic Processes and Condensation Reactions in the Cellulose Solvent System N,N-Dimethylacetamide/Lithium Chloride. Part 1.
  18. Viscoelastic Properties of Liquefied Wood/Epoxy Resin and its Bond Strength
  19. Prof. Dr. Josef Bauch 65 years old
  20. In Memory of Prof. Guglielmo Giordano
  21. Literature Reports
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