Chemo-enzymatic functionalisation of lignocellulose materials using oxiranes

A new non-selective chemo-enzymatic process using oxiranes for functionalisation of lignocellulose materials has been developed. Using a lipase and hydrogen peroxide, soybean oil and linoleic acid were epoxidised resulting in a 52.7% and 92.4% relative conversion to oxirane, respectively. A commercial oxirane, 1,2-epoxyoctane and oxiranes generated from epoxidation of oils (using lipase and hydrogen peroxide) were successfully coupled onto long chain alkylamines while the oxiranes were in turn readily coupled onto phenolic lignin model compounds. Treatment of beech veneers with dodecylamine using this process resulted in a reduction in surface O/C ratio and a 90% increase in hydrophobicity. Since oxiranes react directly with hydroxyl groups and other functional groups this method may provide a new enzymatic non-targeted approach for the functionalisation of various polymeric materials.