Chemical structures of hydrochloric acid lignin, 4: Behavior of 1,2-diaryl-1,3-propanediol in hydrochloric acid
1991
Yasuda, S. (Nagoya Univ. (Japan). Faculty of Agriculture) | Iwase, Y.
1,2-Guaiacyl-1,3-propanediol [alpha-13C], one of lignin structural models, labeled with C-13 at the benzylic position was synthesized and then treated in refluxing 0.2N hydrochloric acid. The 13C NMR analysis of the products strongly supported the already proposed reaction mechanism of so-called "acidolysis" and, at the same time, confirmed no rearrangement of a methyl group in contrast with rearrangement of a hydrogen atom and a phenyl nucleus. Treatment of phenolic and non-phenolic modes in refluxing 5% hydrochloric acid gave less low-molecular-weight compounds and more condensation products in comparison with the acidolysis. Treatment of the models in concentrated (35% and 42%) hydrochloric acid recovered the starting compounds together with condensation products and tentative chlorides. That was in accordance with the fact that hydrochloric acid lignin contains less condensed structural units than sulfuric acid lignin
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