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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

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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Correspondence to Seiichi Yasuda.

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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

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