期刊
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
卷 6, 期 3, 页码 3242-3254出版社
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.7b03418
关键词
Mechanochemistry; Mechanical milling; Oxidation; lignin
资金
- European Union [PITN-GA-2013-607044]
- Distinguished Professorship Program at RWTH Aachen University - Excellence Initiative of the German federal government
- Distinguished Professorship Program at RWTH Aachen University - Excellence Initiative of the German state government
- RWTH - Excellence Initiative of the German federal government [StUpPD_221-16]
- RWTH - Excellence Initiative of the German state government [StUpPD_221-16]
A mechanochemical oxidation and cleavage reaction in lignin beta-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 0-4 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-alpha 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.
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