Thermal behavior of β-1 subunits in lignin: Pyrolysis of 1,2-diarylpropane-1,3-diol-type lignin model compounds

Ken Ichi Kuroda, Tatsuya Ashitani, Koki Fujita, Takefumi Hattori

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14 Citations (Scopus)

Abstract

1,2-Diarylpropane-1,3-diol-type lignin model compounds, 1,2-bis(4-hydroxy-3-methoxyphenyl)propane-1,3-diol (1) and 1-(3,4- diethoxyphenyl)-2-(4-methoxyphenyl)propane-1,3-diol (2), were pyrolyzed at 500°C for 4 s to clarify the thermal behavior of β-1 subunits in lignin. Products were monitored by gas chromatography/mass spectrometry. The cleavage of the Cα-Cβ bond to produce benzaldehydes such as 4-hydroxy-3-methoxybenzaldehyde (9) and phenylethanals as the counterparts such as 4-hydroxy-3-methoxyphenylethanal (10) occurred in pyrolyses of both 1 and 2. In pyrolysis of 1, an oxetane pathway leading to the formation of Z/E-stilbenes without the γ-CH2OH group such as Z/E-4,4′-dihydroxy-3, 3′-dimethoxystilbene (3) was predominant. In pyrolysis of 2, the oxetane pathway was minor, while pathways producing a dimer with a =CγH 2 group by loss of water and a dimer with an α-carbonyl group were predominant. Pyrolysis of Japanese cedar wood provided 3 and 10 in ∼0.8% and 0.6% yields, respectively, based on the Klason lignin content, while pyrolysis of a guaiacyl bulk dehydrogenation polymer gave them in a very small amount.

Original languageEnglish
Pages (from-to)2770-2778
Number of pages9
JournalJournal of Agricultural and Food Chemistry
Volume55
Issue number8
DOIs
Publication statusPublished - Apr 18 2007

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

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