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Official Journal of the Japan Wood Research Society

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Ready chemical conversion of acid hydrolysis lignin into water-soluble lignosulfonate II: Hydroxymethylation and subsequent sulfonation of phenolized lignin model compounds

Journal of Wood Science volume 44, pages 116–124 (1998)Cite this article

Abstract

Highly condensed lignin can be transformed by three reactions — phenolation, hydroxymethylation, and neutral sulfonation — to water-soluble lignosulfonate. To elucidate reactivities and products in the latter two reactions, simple compounds were selected as lignin model compounds. With hydroxymethylation of creosol at 60°C, the yield of a condensed-type product with the diarylmethane structure was less than 10%. Hydroxymethylation of 1-guaiacyl-1-p-hydroxy-phenylethane (compound VI) as a phenolized guaiacyl lignin model compound gave four compounds. The initial reaction introduced the hydroxymethyl group mainly in the guaiacyl nucleus, and the additional reaction created two hydroxymethyl groups in the p-hydroxyphenyl nucleus. Contrary to our estimation, treatment of the models with 13C-labeled formaldehyde (H13CIIO) did not form any diarylmethane structure. Neutral sulfite treatment of hydroxymethylated products gave corresponding sulfonates in high yields. Phenolized guaiacylglycerol-β-aryl ether (compound XVI) showed a reactivity similar to that of compound VI.

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Author notes

  1. Yasuyuki Matsushita

    Present address: Central Research Laboratory, Nippon Paper Industries Co., 114-0002, Oji, Kita-ku, Tokyo, Japan

  2. Hideyuki Goto

    Present address: Iwakuni Research Laboratory of Technology, Nippon Paper Industries Co., 740-0003, Iida-cho, Iwakuni, Japan

Authors and Affiliations

  1. School of Agricultural Sciences, Nagoya University, 464-8601, Nagoya, Japan

    Seiichi Yasuda, Eri Hamaguchi, Yasuyuki Matsushita, Hideyuki Goto & Takanori Imai

Authors
  1. Seiichi Yasuda
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  2. Eri Hamaguchi
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  3. Yasuyuki Matsushita
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  4. Hideyuki Goto
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  5. Takanori Imai
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Corresponding author

Correspondence to Seiichi Yasuda.

Additional information

This paper was presented at the 45th and 46th annual meetings of the Japan Wood Research Society at Tokyo and Kumamoto, April 1995 and April 1996, respectively

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Yasuda, S., Hamaguchi, E., Matsushita, Y. et al. Ready chemical conversion of acid hydrolysis lignin into water-soluble lignosulfonate II: Hydroxymethylation and subsequent sulfonation of phenolized lignin model compounds. J Wood Sci 44, 116–124 (1998). https://doi.org/10.1007/BF00526256

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  • DOI: https://doi.org/10.1007/BF00526256

Key words

  • Lignin
  • Phenolation
  • Hydroxymethylation
  • Sulfonation
  • Lignosulfonate