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Journal of Wood Science

Official Journal of the Japan Wood Research Society

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Reactivity of a condensed–type lignin model compound in the Mannich reaction and preparation of cationic surfactant from sulfuric acid lignin

Journal of Wood Science volume 49, pages 166–171 (2003)Cite this article

Abstract

 The chemical conversion of phenolized sulfuric acid lignin (P-SAL), prepared from sulfuric acid lignin (SAL) by phenolation with sulfuric acid catalyst, to novel cationic surfactant was investigated. To elucidate the chemical reactivity of the P-SAL to a Mannich reaction, 1-guaiacyl-1-p-hydroxyphenylethane (I) as a simple phenolized sulfuric acid lignin model compound was reacted with dimethylamine and formaldehyde. Quantitative analysis of the products by gas-liquid chromatography suggested that the p-hydroxyphenyl nucleus was more reactive than the guaiacyl nucleus. The Mannich reaction of SAL with dimethylamine did not yield a soluble cationic surfactant, but P-SAL produced water-soluble cationic surfactant in a quantitative yield. The Mannich reaction products (MP-SAL) of P-SAL had 1,3-dimethylaminomethyl groups/C9-C6. The results of the surface tension measurements showed that the decrease in surface tension of MP-SAL was much larger than that of lignosulfonate as a commercial surfactant from lignin.

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Authors and Affiliations

  1. Division of Biological Material Sciences, Department of Biosphere Resources Science, Graduate School of Bioagricultural Sciences, Nagoya University, 464-8601, Nagoya, Japan

    Y. Matsushita & S. Yasuda

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  1. Y. Matsushita
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  2. S. Yasuda
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Correspondence to S. Yasuda.

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Received: February 13, 2002 / Accepted: June 12, 2002

Acknowledgments The authors thank Nippon Paper Industries Co. and Lion Corp. for providing the commercial products and Dr. K. Aoi (Graduate School of Bioagricultural Sciences, Nagoya University, Japan) for advising us on the measurement of surface tension. This research was conducted with the support of a Grant-in-Aid for Scientific Research (11460079) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

Part of this report was presented at the 52nd Annual Meeting of the Japan Wood Research Society, Gifu, April 2002

Correspondence to:Y. Matsushita

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Matsushita, Y., Yasuda, S. Reactivity of a condensed–type lignin model compound in the Mannich reaction and preparation of cationic surfactant from sulfuric acid lignin. J Wood Sci 49, 166–171 (2003). https://doi.org/10.1007/s100860300026

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  • DOI: https://doi.org/10.1007/s100860300026