Role of Counter Anion in the Chemical Reaction of Wood Components under Acidic Conditions

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  • Yokoyama Tomoya
    Graduate School of Agricultural and Life Sciences, The University of Tokyo

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  • 木材構成成分の酸性条件下での化学反応におけるカウンターアニオンの役割
  • モクザイ コウセイ セイブン ノ サンセイ ジョウケン カ デ ノ カガク ハンノウ ニ オケル カウンターアニオン ノ ヤクワリ

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Abstract

It was examined in detail how the counter anion of hydrochloric, sulfuric, or hydrobromic acid acts in the reaction of a dimeric non-phenolic β-O-4 type lignin model compound, 2-(2-methoxyphenoxyl)- 1-(3,4-dimethoxyphenyl)propane-1,3-diol (J), or a carbohydrate model compound, methyl β-D-glucopyranoside (S), under acidic conditions. It was confirmed that the β-O-4 bond cleavage of (J) is most or least rapid in the hydrobromic or sulfuric acid system, respectively, which is in accordance with previous knowledge. It was first suggested that an unknown reaction mode for the β-O-4 bond cleavage of (J) appears in the hydrobromic acid system and that there exists the mechanism where the hydride at β-position of the benzyl cation intermediate transfers to the cation center. It was first and strongly suggested that bromide and chloride anions directly participate in the acid hydrolysis reaction of (S) and consequently affect the rate, although it has generally been believed since the middle of the 20th century that the proton activity of a reaction system is the only rate-determining parameter in acid hydrolysis of glycosides.

Journal

  • Mokuzai Gakkaishi

    Mokuzai Gakkaishi 61 (3), 217-225, 2015

    The Japan Wood Research Society

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