Catalytic Hydrotreatment of β-O-4 Ether in Lignin: Cleavage of the C–O Bond and Hydrodeoxygenation of Lignin-Derived Phenols in One Pot,ACS Sustainable Chemistry & Engineering

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Catalytic Hydrotreatment of β-O-4 Ether in Lignin: Cleavage of the C–O Bond and Hydrodeoxygenation of Lignin-Derived Phenols in One Pot
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2020-09-04 , DOI: 10.1021/acssuschemeng.0c04941
Minghao Zhou _{1,

2,

3,

4} , Changzhou Chen _{2,

3} , Peng Liu _{2,

3} , Haihong Xia _{2,

3} , Jing Li _{2,

3} , Brajendra K. Sharma ₄ , Jianchun Jiang _{2,

3}

Affiliation

Selective hydrotreatment of β-O-4 ether bonds in lignin is a key strategy for the lignin valorization. The current catalytic strategy can only transfer β-O-4 model compounds to aromatics. Also, further upgrading was still needed to convert those aromatics/phenols into aviation fuels or chemicals (e.g., cycloalkanes, cycloalcohols) in a following step. Herein, a one-pot method for the hydrotreatment of lignin β-O-4 ether to cycloalkanes/cycloalcohols over NiLa/CNT was reported due to the introduction of La. The dehydroxylation of 2-phenoxy-1-phenylethan-1-ol to phenethoxybenzene was the key step during the hydrotreatment, followed by the β-O-4 bond cleavage to ethylbenzene and phenol, which was then simultaneously hydrogenated to afford ethyl cyclohexane and cyclohexanol. The catalyst acidity was found to be important during the hydrotreatment process, especially the Brønsted acid sites. This was confirmed by control experiments using different reaction intermediates as reactants, as well as analysis of products distribution and DFT calculations. This work provides a novel and economical method for the selective hydrotreatment of lignin model compounds into aviation fuel.

中文翻译：

木质素中β-O-4醚的催化加氢处理：一锅分解木质素衍生的苯酚的C–O键和加氢脱氧

木质素中β-O-4醚键的选择性加氢处理是木质素增值的关键策略。当前的催化策略只能将β-O-4模型化合物转移到芳烃中。此外，仍需要进一步升级，以在后续步骤中将这些芳族化合物/苯酚转化为航空燃料或化学品（例如，环烷烃，环醇）。本文中，由于引入了La，报道了一锅法在NiLa / CNT上将木质素β-O-4醚加氢处理为环烷烃/环醇的方法。2-苯氧基-1-苯基乙-1-醇的脱羟基反应为苯乙氧基苯是加氢处理中的关键步骤，然后将β-O-4键裂解为乙苯和苯酚，然后将其同时氢化得到乙基环己烷和环己醇。发现在加氢处理过程中，催化剂的酸度很重要，尤其是布朗斯台德酸位。通过使用不同的反应中间体作为反应物的对照实验，以及产物分布和DFT计算的分析，证实了这一点。这项工作为木质素模型化合物选择性加氢处理成航空燃料提供了一种新颖而经济的方法。

更新日期：2020-09-28

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