Abstract: A lignin model compound of phenolic β-O-4 type,i.e.guaiacylglycerol-β-guaiacyl ether was synthesized with a modified method.Combination of infrared spectra analysis and 1H NMR was used to identify chemical structure of the products.Afterwards,the β-O-4 type model compound was treated with a new delignification system using (copper)/pyridine/peroxide(GIF system).High resolution 13C NMR and GC-MS analysis were used to investigate the change of chemical structure of β-O-4 type model compound during the reaction.Mechanism of this biomimetic delignification was also explored.Results showed that 4-(α-bromoacetyl)-guaiacol could be obtained from acetovanillone by bromination with copper(Ⅱ) bromide at high yield.Therefore,guaiacylglycerol-β-guaiacyl ether could be synthesized efficiently.Results also indicated that GIF type biomimetic system had strong ability on degradation of phenolic β-O-4 type model compound.After degradation,a series of low molecular aromatic compounds containing carboxyl,(hydroxyl) and carbonyl groups were produced.From their structures,the following reactions were caused by the GIF system:ether-bond cleavage,alkyl-aryl cleavage and Cβ—Cγ cleavage.Consequently,this work provides a comprehensive information on biomimetic delignification system that could be applied to industrial non-pollution bleaching.