Tetramethylammonium hydroxide thermochemolysis of guaiacyl-syringyl and guaiacyl dehydrogenation polymers

Tetramethylammonium hydroxide thermochemolysis of lignin was investigated using guaiacyl-syringyl and guaiacyl dehydrogenation polymers. The guaiacyl-syringyl mixed polymer provided: (1) 1-(3,4-dimethoxyphenyl)-1,2,3-trimethoxypropane isomers (11/12) and 1-(3,4,5-trimethoxyphenyl)-1,2,3-trimethoxypropane isomers (15/16) as β-aryl ether subunit-derived products, (2) 2,3,3′,4′-tetramethoxy-5-(3-methoxyprop-1-enyl)stilbene (18) and 2,3,3′,4′,5′-pentamethoxy-5-(3-methoxyprop-1-enyl)stilbene (22) as β-5 subunit-derived products, (3) pinoresinol dimethyl ether (21), medioresinol dimethyl ether (23) and syringaresinol dimethyl ether (24) as β-β subunit-derived products, respectively, and (4) coniferyl alcohol dimethyl ether (8) and sinapyl alcohol dimethyl ether (14) from 4-O-linked coniferyl and sinapyl alcohols. The ratio of products stemming from β-aryl ether, β-5, β-β subunits was 23:13:64. The guaiacyl polymer provided 11/12, 18, 21, and 8, suggesting the same reactions occurring also in the guaiacyl polymer, although the ratio (31:32:37) of the products from β-aryl ether, β-5, β-β subunits differed.