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Fractionation of woody biomass with boiling aqueous acetic acid containing a small amount of mineral acid at atmospheric pressure: Reactivity of arylglycerol-β-aryl ethers in lignins with aqueous acetic acid containing H2SO4
Journal of Wood Science volume 44, pages 217–221 (1998)
Abstract
To characterize the mechanism of the reaction of lignin with aqueous acetic acid (AW) containing a small amount of H2SO4, guaiacylglycerol-β-guaiacyl ether (GOG), and guaiacylglycerol-β-syringol ether (GOS) were refluxed in 90% AW with 0.28% H2SO4 for 0–120 min. Reaction products and their silylated derivatives were characterized by analytical methods such as gas chromatography-mass spectrometry and nuclear magnetic resonance. When the model compounds were allowed to react at boiling temperature for 0 min (heat-up time 30 min), most of their primary alcohol groups and some of their secondary alcohol groups were acetylated, but their phenolic groups were not. About 90% of GOG was degraded, polymerized, or both during boiling for at least 15 min, yielding guaiacol and isocoumaran compounds (GOG-e and GOG-f) in addition to homovanillin (II) as guaiacylvinyl alcohol (I) and other minor products. GOS yielded syringol, homovanillin (II), and a novel compound (V) together with unknown products but not the corresponding isocoumaran compounds.
References
Sano Y, Nakamura M, Shimamoto S (1990) Pulping of wood at atmospheric pressure: II. Pulping of birch wood with aqueous acetic acid containing a small amount of sulfuric acid. Mokuzai Gakkaishi 36:207–211
Sano Y, Uraki Y, Kubo S, Horisaki Y, Konno H (1996) Total utilization of woody biomass by acetic acid pulping at atmospheric presure (in Japanese). In: Proceedings of the 63rd pulp and paper research conference, pp 26–32
Sano Y, Shimamoto S (1995) Mild hydrogenolysis of acetic acid lignin. Mokuzai Gakkaishi 41:1006–1011
Uraki Y, Kubo S, Nigo N, Sano Y (1995) Preparation of carbon fibers from organosoly lignin obtained by aqueous acetic acid pulping. Holzforschung 49:343–350
Uraki Y, Kubo S, Kurakami H, Sano Y (1997) Active carbon fibers from acetic acid lignin. Holzforschung 51:188–192
Nakamura M, Sano Y (1990) Production of lignin adhesives: resinification of acetic acid lignin (in Japanese). Proc Hokkaido Branch Jpn Wood Res Soc 22:68–73
Kanai T, Sano Y, Sasaya T (1994) Preparation of highly efficient polymers from acetic acid lignin — preparation of cation ion: exchange resin (in Japanese). In: Abstracts of the 44th annual meeting of the Japan Wood Research Society, 59
Sano Y (1989) Reactivity of β-0–4 linkages in lignin during solvolysis pulping: degradation of β-0-4 lignin model compounds. Mokuzai Gakkaishi 35:813–819
Mikshe GE (1966) Zur Synthese der beiden diastereomeren Formen des Guajacylglycerin-β-(2-methoxyphenyl)-athers und des Guajacylglycerins. Acta Chem Scand 20:1038–1043
Ede R, Brunow G, Poppius K (1988) Formic acid/peroxyformic acid pulping: Part 1. Reactions of β-aryl ether model compounds with formic acid. Nord Pulp Pap Res 3:119–123
Yasuda S, Ito N (1987) Behavior of lignin in organic pulping: I. Reaction of arylglycerol-β-aryl ethers with acetic acid. Mokuzai Gakkaishi 33:708–716
Davis JL, Nakatubo F, Murakami K, Umezawa T (1987) Organic acid pulping of wood: IV. Reactions of arylglycerol-β-guaiacyl ethers. Mokuzai Gakkaishi 33:478–486
Lundquist K (1970) Acid degradation of lignin: II. Separation and identification of low molecular weight phenols. Acta Chem Scand 24:889–907
Karlsson O, Lundquist K, Meuller S, Westid K (1988) On the acidolytic cleavage of arylglycerol β-aryl ethers. Acta Chem Scand 42:48–51
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Sano, Y., Shimamoto, S., Enoki, M. et al. Fractionation of woody biomass with boiling aqueous acetic acid containing a small amount of mineral acid at atmospheric pressure: Reactivity of arylglycerol-β-aryl ethers in lignins with aqueous acetic acid containing H2SO4 . J Wood Sci 44, 217–221 (1998). https://doi.org/10.1007/BF00521966
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DOI: https://doi.org/10.1007/BF00521966