TY - JOUR
T1 - Laccase catalyzed covalent coupling of fluorophenols increases lignocellulose surface hydrophobicity
AU - Kudanga, Tukayi
AU - Prasetyo, Endry Nugroho
AU - Widsten, Petri
AU - Kandelbauer, Andreas
AU - Jury, Sandra
AU - Heathcote, Carol
AU - Sipilä, Jussi
AU - Weber, Hansjoerg
AU - Nyanhongo, Gibson S.
AU - Guebitz, Georg M.
PY - 2010/4
Y1 - 2010/4
N2 - 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.
AB - 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.
KW - Coupling
KW - Fluoropolymers
KW - Functionalization
KW - Laccase
KW - Wood hydrophobicity
UR - http://www.scopus.com/inward/record.url?scp=73749088360&partnerID=8YFLogxK
U2 - 10.1016/j.biortech.2009.12.002
DO - 10.1016/j.biortech.2009.12.002
M3 - Article
C2 - 20044252
AN - SCOPUS:73749088360
SN - 0960-8524
VL - 101
SP - 2793
EP - 2799
JO - Bioresource Technology
JF - Bioresource Technology
IS - 8
ER -
