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A New Approach Towards the Yellowing Inhibition of Mechanical Pulps. Part I: Selective Removal of α-Hydroxyl and α-Carbonyl Groups in Lignin Model Compounds

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Veröffentlicht/Copyright: 1. Juni 2005
Holzforschung
Aus der Zeitschrift Band 53 Heft 1

Summary

The α-hydroxyl group in lignin model compounds 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol (1) and 1-(4-hydroxy-3-methoxyphenyl)ethanol (3), and the α-carbonyl group in 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one (5) are removed by treatment of the model compounds with trifluoroacetic acid (CF3CO OH) and triethylsilane (Et3sih) in methylene chloride. The reaction is highly chemoselective and it tolerates the lignin γ-hydroxyl group, phenol and β-O-4-aryl ether linkage. The α-hydroxyl group in 1 has also been removed with triethylsilane in aqueous trifluoroacetic acid (CF3CO OH : H2o = 75 : 25).

The combination of trifluoroacetic acid and sodium borohydride, or sodium triacetoxyborohydride, is also effective in removing the α-carbonyl group in 5 and the α-hydroxyl group in lignin model compound 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)ethanol (7) and in milled wood lignin. The selective removal of the lignin α-hydroxyl and α-carbonyl groups may potentially be used, in conjunction with the protection of the lignin phenol, to inhibit the light and/or heat-induced yellowing of mechanical pulps.

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Published Online: 2005-06-01
Published in Print: 1999-01-01

Copyright (c)1999 by Walter de Gruyter GmbH & Co. KG

Artikel in diesem Heft

  1. Factors Affecting Crystalline Structure of Cellulose during Solvent Purification Treatment
  2. Rupture of Pit Membranes in Sugi (Cryptomerica japanica D. Don) Logs by a Smoke Heating System with Increased Far-Infrared Radiation
  3. Fungal Treatment of Aspen for Wood Resin Reduction: Effect on Aged Aspen Wood Chips at Room Temperature and at 5°C
  4. Hydroxyl Radical Generation by an Extracellular Low-Molecular-Weight Substance and Phenol Oxidase Activity During Wood Degradation by the White-Rot Basidiomycete Phanerochaete chrysosporium
  5. Industrial Utilization of Tobacco Stalks (1) Preliminary Evaluation for Biomass Resources
  6. Characterization of Lignin-Carbohydrate Fractions Isolated from the Wood Parasite Cistance deserticola Y.C. Ma
  7. Acid Reactions of Lignin Models of β-5 Type
  8. A New Approach Towards the Yellowing Inhibition of Mechanical Pulps. Part I: Selective Removal of α-Hydroxyl and α-Carbonyl Groups in Lignin Model Compounds
  9. Atmospheric Acetic Acid Pulping of Rice Straw II: Behavior of Ash and Silica in Rice Straw during Atmospheric Acetic Acid Pulping and Bleaching
  10. Variability of Suberin Composition of Reproduction Cork from Quercus suber Throughout Industrial Processing
  11. The Effects of Water Soluble Extractives on the Acoustic Properties of Reed (Arundo donax L.)
  12. Wood Moisture Gradient Analysis by Electrical Impedance Spectroscopy
  13. Non-Darcian Air Flow in Wood. Part 2. Nonlinear Flow
  14. Non-Darcian Air Flow in Wood. Part 3. Molecular Slip Flow
  15. Laser Ablation of Machined Wood Surfaces. 1. Effect on End-Grain Gluing of Pine (Pinus silvestris L.) and Spruce (Picea abies Karst.)
  16. A Study of Ordinary Portland Cement Hydration With Wood by Isothermal Calorimetry
  17. Literature Reports
https://doi.org/10.1515/HF.1999.008

Artikel in diesem Heft

  1. Factors Affecting Crystalline Structure of Cellulose during Solvent Purification Treatment
  2. Rupture of Pit Membranes in Sugi (Cryptomerica japanica D. Don) Logs by a Smoke Heating System with Increased Far-Infrared Radiation
  3. Fungal Treatment of Aspen for Wood Resin Reduction: Effect on Aged Aspen Wood Chips at Room Temperature and at 5°C
  4. Hydroxyl Radical Generation by an Extracellular Low-Molecular-Weight Substance and Phenol Oxidase Activity During Wood Degradation by the White-Rot Basidiomycete Phanerochaete chrysosporium
  5. Industrial Utilization of Tobacco Stalks (1) Preliminary Evaluation for Biomass Resources
  6. Characterization of Lignin-Carbohydrate Fractions Isolated from the Wood Parasite Cistance deserticola Y.C. Ma
  7. Acid Reactions of Lignin Models of β-5 Type
  8. A New Approach Towards the Yellowing Inhibition of Mechanical Pulps. Part I: Selective Removal of α-Hydroxyl and α-Carbonyl Groups in Lignin Model Compounds
  9. Atmospheric Acetic Acid Pulping of Rice Straw II: Behavior of Ash and Silica in Rice Straw during Atmospheric Acetic Acid Pulping and Bleaching
  10. Variability of Suberin Composition of Reproduction Cork from Quercus suber Throughout Industrial Processing
  11. The Effects of Water Soluble Extractives on the Acoustic Properties of Reed (Arundo donax L.)
  12. Wood Moisture Gradient Analysis by Electrical Impedance Spectroscopy
  13. Non-Darcian Air Flow in Wood. Part 2. Nonlinear Flow
  14. Non-Darcian Air Flow in Wood. Part 3. Molecular Slip Flow
  15. Laser Ablation of Machined Wood Surfaces. 1. Effect on End-Grain Gluing of Pine (Pinus silvestris L.) and Spruce (Picea abies Karst.)
  16. A Study of Ordinary Portland Cement Hydration With Wood by Isothermal Calorimetry
  17. Literature Reports
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