Laccase catalyzed covalent coupling of fluorophenols increases lignocellulose surface hydrophobicity

Tukayi Kudanga, Endry Nugroho Prasetyo, Petri Widsten, Andreas Kandelbauer, Sandra Jury, Carol Heathcote, Jussi Sipilä, Hansjoerg Weber, Gibson S. Nyanhongo*, Georg M. Guebitz

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

61 Citations (Scopus)

Abstract

This work presents for the first time the mechanistic evidence of a laccase-catalyzed method of covalently grafting hydrophobicity enhancing fluorophenols onto Fagus sylvatica veneers. Coupling of fluorophenols onto complex lignin model compounds guaiacylglycerol β-guaiacyl ether and syringylglycerol β-guaiacyl ether was demonstrated by LC-MS and NMR. Laccase-mediated coupling increased binding of 4-[4-(trifluoromethyl)phenoxy]phenol (4,4-F3MPP) and 4-(trifluoromethoxy)phenol (4-F3MP) to veneers by 77.1% and 39.2%, respectively. XPS studies showed that laccase-catalyzed grafting of fluorophenols resulted in a fluorine content of 6.39% for 4,4-F3MPP, 3.01% for 4-F3MP and 0.26% for 4-fluoro-2-methylphenol (4,2-FMP). Grafting of the fluorophenols 4,2-FMP, 4-F3MP and 4,4-F3MPP led to a 9.6%, 28.6% and 65.5% increase in hydrophobicity, respectively, when compared to treatments with the respective fluorophenols in the absence of laccase, in good agreement with XPS data.

Original languageEnglish
Pages (from-to)2793-2799
Number of pages7
JournalBioresource Technology
Volume101
Issue number8
DOIs
Publication statusPublished - Apr 2010
Externally publishedYes

Keywords

  • Coupling
  • Fluoropolymers
  • Functionalization
  • Laccase
  • Wood hydrophobicity

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