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Mild selective oxidative cleavage of lignin C-C bonds over a copper catalyst in water
Hu, Yuzhen1,3; Yan, Long1; Zhao, Xuelai4; Wang, Chenguang1,4; Li, Song1,3; Zhang, Xinghua1,2; Ma, Longlong1,2; Zhang, Qi1,2
2021-08-04
发表期刊GREEN CHEMISTRY
ISSN1463-9262
页码11
通讯作者Wang, Chenguang(wangcg@ms.giec.ac.cn) ; Zhang, Qi(zhangqi@ms.giec.ac.cn)
摘要The conversion of lignin into aromatics as commodity chemicals and high-quality fuels is a highly desirable goal for biorefineries. However, the presence of robust inter-unit carbon-carbon (C-C) bonds in natural lignin seriously impedes this process. Herein, for the first time, we report the selective cleavage of C-C bonds in beta-O-4 and beta-1 linkages catalyzed by cheap copper and a base to yield aromatic acids and phenols in excellent yields in water at 30 degrees C under air without the need for additional complex ligands. Isotope-labeling experiments show that a base-mediated C-beta-H bond cleavage is the rate-determining step for C-alpha-C-beta bond cleavage. Density functional theory (DFT) calculations suggest that the oxidation of beta-O-4 ketone to a key intermediate, i.e., a peroxide, by copper and O-2 lowers the C-alpha-C-beta bond dissociation energy and facilitates its subsequent cleavage. In addition, the catalytic system could be successfully applied to the depolymerization of various authentic lignin feedstocks, affording excellent yields of aromatic compounds and high selectivity of a single monomer. This study offers the potential to economically produce aromatic chemicals from biomass.
DOI10.1039/d1gc02102h
关键词[WOS]MODEL COMPOUNDS ; VALUABLE CHEMICALS ; ALCOHOL OXIDATION ; MOLECULAR-OXYGEN ; DEPOLYMERIZATION ; ACID ; WOOD ; PYROLYSIS ; CELLULOSE ; HYDROGENOLYSIS
收录类别SCI
语种英语
资助项目National Natural Science Foundation of China[51876209] ; National Key Research and Development Program of China[2018YFB1501504] ; Transformational Technologies for Clean Energy and Demonstration ; Strategic Priority Research Program of the Chinese Academy of Sciences[XDA21060102] ; Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program[2017BT01N092] ; Guangdong Special Support Plan Science and Technology Innovation Leader Project[2019TX05L362]
WOS研究方向Chemistry ; Science & Technology - Other Topics
项目资助者National Natural Science Foundation of China ; National Key Research and Development Program of China ; Transformational Technologies for Clean Energy and Demonstration ; Strategic Priority Research Program of the Chinese Academy of Sciences ; Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program ; Guangdong Special Support Plan Science and Technology Innovation Leader Project
WOS类目Chemistry, Multidisciplinary ; Green & Sustainable Science & Technology
WOS记录号WOS:000686294100001
出版者ROYAL SOC CHEMISTRY
引用统计
被引频次:25[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.giec.ac.cn/handle/344007/33643
专题中国科学院广州能源研究所
通讯作者Wang, Chenguang; Zhang, Qi
作者单位1.Chinese Acad Sci, Guangzhou Inst Energy Convers, CAS Key Lab Renewable Energy, Guangdong Prov Key Lab New & Renewable Energy Res, Guangzhou 510640, Guangdong, Peoples R China
2.Southeast Univ, Sch Energy & Environm, Minist Educ, Key Lab Energy Thermal Convers & Control, Nanjing 210096, Jiangsu, Peoples R China
3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
4.Univ Sci & Technol China, Dept Thermal Sci & Energy Engn, Hefei 233022, Anhui, Peoples R China
第一作者单位中国科学院广州能源研究所
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GB/T 7714
Hu, Yuzhen,Yan, Long,Zhao, Xuelai,et al. Mild selective oxidative cleavage of lignin C-C bonds over a copper catalyst in water[J]. GREEN CHEMISTRY,2021:11.
APA Hu, Yuzhen.,Yan, Long.,Zhao, Xuelai.,Wang, Chenguang.,Li, Song.,...&Zhang, Qi.(2021).Mild selective oxidative cleavage of lignin C-C bonds over a copper catalyst in water.GREEN CHEMISTRY,11.
MLA Hu, Yuzhen,et al."Mild selective oxidative cleavage of lignin C-C bonds over a copper catalyst in water".GREEN CHEMISTRY (2021):11.
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