Tetramethylammonium hydroxide (TMAH) thermochemolysis of 2-arylcoumaran lignin model compounds

Ken ichi Kuroda, Akiko Nakagawa-izumi, Tatsuya Ashitani, Koki Fujita

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Phenolic 2-arylcoumarans 1-6 were used to examine the behaviors of β-5 subunits in lignin during tetramethylammonium hydroxide (TMAH) thermochemolysis. Products were monitored by gas chromatography/mass spectrometry. The process predominantly provided dimeric products with the opened hydrofuran ring. Substituent changes at the γ-position of ring A and at the 5-position of ring B had a large effect on the product compositions. 2-Arylcoumarans 1 and 6 with the γ-CH2OH substituent predominantly gave 2,3,3′,4′-tetramethoxystilbenes involving the elimination of the γ-CH2OH substituent, while 2-5 with the γ-CH3 substituent gave a mixture of 2,3,3′,4′-tetramethoxy-α-methylstilbenes and α-methoxy-α-(3′,4′-dimethoxyphenyl)-β-(2,3-dimethoxyphenyl)propanes. Substituent -CH{double bond, long}CHCH3 on ring B remained unaffected. Substituents -CH{double bond, long}CHCH2OH and -COOH on ring B produced the corresponding methyl ether and ester, respectively, by methylation. The -CH{double bond, long}CHCHO substituent on ring B was converted to the -CHO substituent.

Original languageEnglish
Pages (from-to)185-191
Number of pages7
JournalJournal of Analytical and Applied Pyrolysis
Volume86
Issue number1
DOIs
Publication statusPublished - Jan 1 2009

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Methyl Ethers
Propane
Methylation
Lignin
Gas chromatography
Mass spectrometry
Ethers
Esters
Chemical analysis
tetramethylammonium

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Tetramethylammonium hydroxide (TMAH) thermochemolysis of 2-arylcoumaran lignin model compounds. / Kuroda, Ken ichi; Nakagawa-izumi, Akiko; Ashitani, Tatsuya; Fujita, Koki.

In: Journal of Analytical and Applied Pyrolysis, Vol. 86, No. 1, 01.01.2009, p. 185-191.

Research output: Contribution to journalArticle

Kuroda, Ken ichi ; Nakagawa-izumi, Akiko ; Ashitani, Tatsuya ; Fujita, Koki. / Tetramethylammonium hydroxide (TMAH) thermochemolysis of 2-arylcoumaran lignin model compounds. In: Journal of Analytical and Applied Pyrolysis. 2009 ; Vol. 86, No. 1. pp. 185-191.
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