Electrochemical oxidation mechanisms for selective products due to C-O and C-C cleavages of beta-O-4 linkages in lignin model compounds

doi:10.1039/d0cp01091j

	Electrochemical oxidation mechanisms for selective products due to C-O and C-C cleavages of beta-O-4 linkages in lignin model compounds
	Chen, Jing 2; Yang, Hanling 2; Fu, Hongquan 2; He, Hongyan 1; Zeng, Qiang 2; Li, Xuehui 2
刊名	PHYSICAL CHEMISTRY CHEMICAL PHYSICS
	2020-05-28
卷号	22 期号:20 页码:11508-11518
ISSN号	1463-9076
DOI	10.1039/d0cp01091j
英文摘要	Electrochemical oxidation is a promising and effective method for lignin depolymerization owing to its selective oxidation capacity and environmental friendliness. Herein, the electrooxidation of non-phenolic alkyl aryl ether monomers and beta-O-4 dimers was experimentally (by cyclic voltammetry, in situ spectroelectrochemistry, and gas chromatography-mass spectroscopy) and theoretically (by DFT calculations) explored in detail. Compared to the reported literature (T. Shiraishi, T. Takano, H. Kamitakahara and F. Nakatsubo, Holzforschung, 2012, 66(3), 303-309), 1-(4-ethoxyphenyl)ethanol showed a distinguishable oxidation pathway, where the resulting carbonyl product surprisingly underwent a bond cleavage on alkyl-aryl ether to ultimately produce a quinoid like compound. In contrast, beta-O-4 dimers, like 2-phenoxy-1-phenethanol and 2-phenoxyacetophenone also demonstrated electrochemical oxidation induced by C-beta-O and C-alpha-C-beta bond cleavages. For the oxidation products, the presence of the C-alpha-hydroxyl group in dimers was the key to selectively generate aldehyde-containing species under mild electrochemical conditions, otherwise it produces alcohol-containing products following a different mechanism compared to the C-alpha & xe001;O containing dimers.
资助项目	National Natural Science Foundation of China[21975082] ; National Natural Science Foundation of China[21922813] ; National Natural Science Foundation of China[21736003] ; National Natural Science Foundation of China[21690083] ; Guangdong Basic and Applied Basic Research Foundation[2019A1515011472] ; Science and Technology Program of Guangzhou, China[201804020014]
WOS关键词	BOND-CLEAVAGE ; PHOTOCATALYTIC OXIDATION ; CATALYTIC-OXIDATION ; AEROBIC OXIDATION ; VISIBLE-LIGHT ; PB/PBO2 ANODE ; DEGRADATION ; DEPOLYMERIZATION ; HYDROGENOLYSIS ; COPPER
WOS研究方向	Chemistry ; Physics
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000538039300030
资助机构	National Natural Science Foundation of China ; Guangdong Basic and Applied Basic Research Foundation ; Science and Technology Program of Guangzhou, China
内容类型	期刊论文
源URL	[http://ir.ipe.ac.cn/handle/122111/40954]
专题	中国科学院过程工程研究所
通讯作者	Zeng, Qiang; Li, Xuehui
作者单位	1.Chinese Acad Sci, CAS Key Lab Green Proc & Engn, Inst Proc Engn, Beijing 100190, Peoples R China 2.South China Univ Technol, Sch Chem & Chem Engn, State Key Lab Pulp & Paper Engn, Guangzhou 510640, Peoples R China
推荐引用方式 GB/T 7714	Chen, Jing,Yang, Hanling,Fu, Hongquan,et al. Electrochemical oxidation mechanisms for selective products due to C-O and C-C cleavages of beta-O-4 linkages in lignin model compounds[J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS,2020,22(20):11508-11518.
APA	Chen, Jing,Yang, Hanling,Fu, Hongquan,He, Hongyan,Zeng, Qiang,&Li, Xuehui.(2020).Electrochemical oxidation mechanisms for selective products due to C-O and C-C cleavages of beta-O-4 linkages in lignin model compounds.PHYSICAL CHEMISTRY CHEMICAL PHYSICS,22(20),11508-11518.
MLA	Chen, Jing,et al."Electrochemical oxidation mechanisms for selective products due to C-O and C-C cleavages of beta-O-4 linkages in lignin model compounds".PHYSICAL CHEMISTRY CHEMICAL PHYSICS 22.20(2020):11508-11518.