Phenyl nucleus-exchange method for the degradation of lignin

Summary The phenyl nucleus-exchange method (NE-method) is a procedure for the degradation of lignin which allows the C–C linkages between the side chains and the phenyl nuclei to be cleaved selectively, and the phenyl nuclei to be liberated finally as polyhydric phenols. The important characteristic of this method is to take advantage of the dealkylation in diphenylmethane type structures in the presence of boron trifluoride and excess phenol, for the degradation of lignin. The lignin building units which give phenol monomers (guaiacol and/or catechol in softwood lignin) almost quantitatively by this method are noncondensed types and diphenylmethane types, and each of these units has any of the benzyl alcohol, the benzyl ether, the conjugated double bond, the -carbonyl group and the C-aryl bond, in the side chain. The yields of phenyl nuclei are about 25–30% in softwood protolignins and about 8–13% in technical lignins. In this paper, the reaction theory and the degradation mechanism of lignins in the NE-method are outlined.