Pyrolysis behavior of the milled wood lignin (MWL) isolated from Japanese cedar (Cryptomeria Japonica) wood was studied in N-2 at 200-400 degrees C, as compared with the reactivities of various guaiacyl-types of lignin model dimers. The model dimer reactivity varied significantly depending on the structure including phenolic, methylated and linkage types. The C-beta-O cleavage to cinnamyl alcohol-type structure (P-ether linkage) and C-gamma-elimination to stilbene-type structure (beta-aryl linkage) were the major pyrolytic pathways in both dimer and MWL. With increasing the pyrolysis temperature of MWL, condensation, depolymerization and carbonization (formation of a multiple aromatic ring system) started at 250, 350 and 400 degrees C, respectively, in 1 min pyrolysis. Although methylation of the hydroxyl groups in MWL substantially reduced the condensation reactivity, depolymerization temperature did not change by methylation. By comparing the model dimer reactivity, roles of the linkage-types between phenylpropane-units in lignin were suggested; the phenolic end-group, which would form some conjugated C-alpha=C-beta structures, is important for low-temperature condensation; effective depolymerization of lignin macromolecule is related to the cleavage of the alpha-ether-linkage in lignin ether chain; reaction of the aromatic ring itself, which includes the O-CH3 homolysis, relates to the carbonization. (C) 2007 Elsevier B.V. All rights reserved.