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| Electrochemical oxidation mechanisms for selective products due to C-O and C-C cleavages of beta-O-4 linkages in lignin model compounds | |
| Chen, Jing1; Yang, Hanling1; Fu, Hongquan1; He, Hongyan2; Zeng, Qiang1; Li, Xuehui1 | |
| 2020-05-28 | |
| Source Publication | PHYSICAL CHEMISTRY CHEMICAL PHYSICS
 |
| ISSN | 1463-9076 |
| Volume | 22Issue:20Pages:11508-11518 |
| Abstract | 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. |
| DOI | 10.1039/d0cp01091j |
| Language | 英语 |
| WOS Keyword | BOND-CLEAVAGE ; PHOTOCATALYTIC OXIDATION ; CATALYTIC-OXIDATION ; AEROBIC OXIDATION ; VISIBLE-LIGHT ; PB/PBO2 ANODE ; DEGRADATION ; DEPOLYMERIZATION ; HYDROGENOLYSIS ; COPPER |
| Funding Project | 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 Research Area | Chemistry ; Physics |
| WOS Subject | Chemistry, Physical ; Physics, Atomic, Molecular & Chemical |
| Funding Organization | National Natural Science Foundation of China ; Guangdong Basic and Applied Basic Research Foundation ; Science and Technology Program of Guangzhou, China |
| WOS ID | WOS:000538039300030 |
| Publisher | ROYAL SOC CHEMISTRY |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.ipe.ac.cn/handle/122111/40955 |
| Collection | 中国科学院过程工程研究所 |
| Corresponding Author | Zeng, Qiang; Li, Xuehui |
| Affiliation | 1.South China Univ Technol, Sch Chem & Chem Engn, State Key Lab Pulp & Paper Engn, Guangzhou 510640, Peoples R China 2.Chinese Acad Sci, CAS Key Lab Green Proc & Engn, Inst Proc Engn, Beijing 100190, Peoples R China |
| Recommended Citation 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. |
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