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β-Ether-type dimers, [1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1-propanol and 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-1-propanol], and an α,β-diether-type trimer [1-(4-(3,4-dimethoxybenzyloxy)-3-methoxyphenyl) -2- (2-methoxyphenoxy) -1-propanol] were pyrolyzed in a closed ampoule reactor (N 2 /250–400°C/2 min). 1-Phenylpropenes (C α =C β ) and 1-phenylpropanones (C α =O) were obtained as the major β-ether-cleaved products. Radical chain mechanisms are proposed in which hydrogen abstraction at the phenolic O- H  and C α - H s occurs, respectively. The former reaction which gives rise to three radical species was much more effective than the latter. As the effective reaction increases the radical concentration, cleavage of the β-ether linkage in the phenolic dimer is achieved at a much lower temperature (260°C) than that of the non-phenolic type (360°C). Radical chain reactions are initiated in the case of the trimer with a weak C α -O bond at lower temperature (320°C) than those of the non-phenolic (methylated) dimer, since homolysis of the C α -O bond produces the phenoxy type dimer and 3,4-dimethoxybenzyl radicals as initiators. However, some of the dimer phenoxyl radical was stabilized by H-abstraction (to form dimer) or by recombination with a 3,4-dimethoxybenzyl radical (to form C-benzylated products) so that the chain depolymerization via quinone methide intermediate was suppressed.

Radical chain reactions in pyrolytic cleavage of the ether linkages of lignin model dimers and a trimer