Mechanochemical Oxidation and Cleavage of Lignin β-O-4 Model Compounds and Lignin,ACS Sustainable Chemistry & Engineering

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Mechanochemical Oxidation and Cleavage of Lignin β-O-4 Model Compounds and Lignin
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2018-01-17 00:00:00 , DOI: 10.1021/acssuschemeng.7b03418
Saumya Dabral ₁ , Hermann Wotruba ₂ , José G. Hernández ₁ , Carsten Bolm ₁

Affiliation

A mechanochemical oxidation and cleavage reaction in lignin β-O-4 model compounds and lignin catalyzed by HO–TEMPO/KBr/Oxone (TEMPO is 2,2,6,6-tetramethyl-1-piperidinyloxy) has been developed under milling conditions. The studies on nonphenolic lignin β-O-4 model compounds led to selective oxidations of the benzylic hydroxyl groups. Subjecting phenolic lignin model compounds to the oxidative conditions in a ball mill initiated aryl–C_α bond cleavage reactions leading to the formation of the corresponding quinones and phenol derivatives. Transferring the mechanochemical protocol to lignin resulted in the simultaneous oxidation and cleavage of bonds with varied selectivity for monomeric products. Finally, a scale-up approach of the oxidative procedure by using vibrating disc mill technology enabled the mechanochemical protocol to be applied in gram-scale batch reactions under reduced milling time, while affording a similar extent of oxidation.

中文翻译：

木质素β-O-4模型化合物和木质素的机械化学氧化和裂解

在研磨条件下，开发了木质素β-O-4模型化合物和HO-TEMPO / KBr / Oxone（TEMPO为2,2,6,6-四甲基-1-哌啶基氧基）催化的木质素的机械化学氧化和裂解反应。对非酚木质素β-O-4模型化合物的研究导致了苄基羟基的选择性氧化。在球磨机中将酚木质素模型化合物置于氧化条件下引发芳基_-Cα键断裂反应导致形成相应的醌和苯酚衍生物。将机械化学方法转移到木质素上导致键的同时氧化和裂解，同时对单体产物具有不同的选择性。最后，通过使用振动盘磨机技术扩大氧化过程的方法，可以在减少研磨时间的情况下将机械化学方案应用于克级批量反应中，同时提供相似程度的氧化。

更新日期：2018-01-17

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