title: Pyrolysis of lignin in the presence of tetramethylammonium hydroxide (TMAH): products stemming from beta-5 substructures.
abstract: Lignin model compounds, synthetic lignins, and cedar wood have been analyzed by pyrolysis-gas chromatography(-mass spectrometry) in the presence of tetramethylammonium hydroxide (TMAH) to examine the behavior of beta-5 substructures specifically under these conditions. Two model compounds contained a beta-5 linkage and a gamma-CH2OH group. The phenolic model compound produced stilbene products by way of a formaldehyde elimination of the gamma-CH2OH. The nonphenolic model compound underwent dehydration to give arylbenzofuran products. Dehydrogenation polymers of coniferyl alcohol gave a large amount of stilbene products in TMAH/pyrolysis. TMAH/pyrolysis of a Japanese cedar (Cryptomeria japonica) wood yielded a very small amount of stilbene products. The results demonstrated that synthetic lignins are rich in terminal beta-5 substructures, but cedar (a softwood) contains a paucity of the terminal beta-5 substructures.
authors.affiliation: Institute of Agricultural and Forest Engineering, University of Tsukuba, Tsukuba, Ibaraki 305-8572, Japan. ken@sakura.cc.tsukuba.ac.jp
authors.forename: Ken-Ichi
authors.initials: K
authors.lastname: Kuroda
authors.forename: Akiko
authors.initials: A
authors.lastname: Nakagawa-Izumi
authors.forename: Donald R
authors.initials: DR
authors.lastname: Dimmel
mesh_terms: D008401:Gas Chromatography-Mass Spectrometry; D006358:Hot Temperature; D008031:Lignin / Q000737:chemistry*; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds
chemical_list: D000644:Quaternary Ammonium Compounds; D008031:Lignin; C027917:tetramethylammonium