Chemical synthesis of β-O-4 type artificial lignin

Chemical synthesis of β-O-4 type artificial lignin
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DOI:
10.1039/b518005h
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发表时间:
2006-01-01
影响因子:
3.2
通讯作者:
Ubukata, M
Ubukata, M
中科院分区:
化学3区
文献类型:
--
作者:
Kishimoto, T;Uraki, Y;Ubukata, M

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合成了一种仅含β-O-4亚结构的人造木质素聚合物。该方法由两个关键步骤组成:1)通过芳族威廉姆森反应使溴化单体缩聚;和2)随后还原羰基聚合物。该聚合物的C-13-NMR和HMQC谱与从日本冷杉木材中分离的研磨木材木质素中的β-O-4亚结构一致。重均聚合度(DPw)范围为19.5至30.6,这是可比的酶促合成的人工木质素从对羟基肉桂醇(脱氢聚合物,DHP)和一些分离的木质素。使用这种新的木质素模型聚合物,它现在将有可能重新调查的性质和反应性的主要木质素结构方面的聚合特征。
An artificial lignin polymer containing only the beta-O-4 substructure was synthesized. The procedure consists of two key steps: 1) polycondensation of a brominated monomer by aromatic Williamson reaction; and 2) subsequent reduction of the carbonyl polymer. C-13-NMR and HMQC spectra of the polymer were consistent with beta-O-4 substructures in milled wood lignin isolated from Japanese fir wood. The weight average degree of polymerization (DPw) ranged from 19.5 to 30.6, which is comparable to enzymatically synthesized artificial lignin from p-hydroxycinnamyl alcohols ( dehydrogenation polymer, DHP) and some isolated lignins. Using this new lignin model polymer, it will now be possible to reinvestigate the properties and reactivity of the main lignin structure in terms of its polymeric character.