Selective Production of Diethyl Maleate via Oxidative Cleavage of Lignin Aromatic Unit

被引:91
作者
Cai, Zhenping [1 ]
Long, Jinxing [1 ]
Li, Yingwen [1 ]
Ye, Lin [2 ]
Yin, Biaolin [1 ]
France, Liam John [1 ]
Dong, Juncai [3 ]
Zheng, Lirong [3 ]
He, Hongyan [4 ]
Liu, Sijie [1 ]
Tsang, Shik Chi Edman [2 ]
Li, Xuehui [1 ]
机构
[1] South China Univ Technol, Sch Chem & Chem Engn, State Key Lab Pulp & Paper Engn, Guangzhou 510640, Guangdong, Peoples R China
[2] Univ Oxford, Wolfson Catalysis Inorgan Chem Lab, Oxford OX1 3QR, England
[3] Chinese Acad Sci, Inst High Energy Phys, Beijing Synchrotron Radiat Facil, Beijing 100049, Peoples R China
[4] Chinese Acad Sci, Inst Proc Engn, Beijing Key Lab Ion Liquids Clean Proc, Beijing 100190, Peoples R China
关键词
N-BUTANE OXIDATION; O BOND-CLEAVAGE; CATALYTIC-OXIDATION; MALEIC-ACID; CHEMICALS; BIOMASS; DEPOLYMERIZATION; TRANSFORMATION; COPPER;
D O I
10.1016/j.chempr.2019.05.021
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Green production of bulk chemicals traditionally obtained from fossil resources is of great importance. One potential route toward realizing this goal is through the utilization of renewable lignin; however, current techniques generally lead to low product specificity because of the structural diversity of this recalcitrant biopolymer. Herein, we devised a new catalytic system to promote selectively oxidative lignin in air, and diethyl maleate was formed at impressively high yield of 404.8 mg g(-1) and selectivity of 72.7% over the polyoxometalate ionic liquid of [BSmim]CuPW12O40. This high catalytic activity is ascribed to a five-coordinated Cu+ species, which, through the formation of end-on dioxygen species in vacant orbitals, facilitates the selective oxidation of basic lignin aromatic units (phenylpropane C-9 units). Therefore, these results represent significant progress toward the realization of an industrially applicable and highly selective lignin oxidation process for the generation of value-added and bulk chemicals.
引用
收藏
页码:2365 / 2377
页数:13
相关论文
共 40 条
[1]   Asymmetric Hydrogenation of Maleic Acid Diesters and Anhydrides** [J].
Bernasconi, Maurizio ;
Mueller, Marc-Andre ;
Pfaltz, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (21) :5385-5388
[2]   Catalytic Depolymerization of Organosolv Lignin in a Novel Water/Oil Emulsion Reactor: Lignin as the Self-Surfactant [J].
Cai, Zhenping ;
Li, Yingwen ;
He, Hongyan ;
Zeng, Qiang ;
Long, Jinxing ;
Wang, Lefu ;
Li, Xuehui .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2015, 54 (46) :11501-11510
[3]   MECHANISTIC ASPECTS OF MALEIC-ANHYDRIDE SYNTHESIS FROM C4-HYDROCARBONS OVER PHOSPHORUS VANADIUM-OXIDE [J].
CENTI, G ;
TRIFIRO, F ;
EBNER, JR ;
FRANCHETTI, VM .
CHEMICAL REVIEWS, 1988, 88 (01) :55-80
[4]   Investigation of the mechanism of n-butane oxidation on vanadium phosphorus oxide catalysts:: Evidence from isotopic labeling studies [J].
Chen, B ;
Munson, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1638-1652
[5]   Chemical routes for the transformation of biomass into chemicals [J].
Corma, Avelino ;
Iborra, Sara ;
Velty, Alexandra .
CHEMICAL REVIEWS, 2007, 107 (06) :2411-2502
[6]   The kinetic significance of V5+ in n-butane oxidation catalyzed by vanadium phosphates [J].
Coulston, GW ;
Bare, SR ;
Kung, H ;
Birkeland, K ;
Bethke, GK ;
Harlow, R ;
Herron, N ;
Lee, PL .
SCIENCE, 1997, 275 (5297) :191-193
[7]   Chemicals from biomass [J].
Dodds, David R. ;
Gross, Richard A. .
SCIENCE, 2007, 318 (5854) :1250-1251
[8]   Controlling the Catalytic Aerobic Oxidation of Phenols [J].
Esguerra, Kenneth Virgel N. ;
Fall, Yacoub ;
Petitjean, Laurene ;
Lumb, Jean-Philip .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (21) :7662-7668
[9]   Valorization of Lignin to Simple Phenolic Compounds over Tungsten Carbide: Impact of Lignin Structure [J].
Guo, Haiwei ;
Zhang, Bo ;
Qi, Zaojuan ;
Li, Changzhi ;
Ji, Jianwei ;
Dai, Tao ;
Wang, Aiqin ;
Zhang, Tao .
CHEMSUSCHEM, 2017, 10 (03) :523-532
[10]   HETEROPOLY ACIDS AND RELATED-COMPOUNDS AS CATALYSTS FOR FINE CHEMICAL SYNTHESIS [J].
KOZHEVNIKOV, IV .
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 1995, 37 (02) :311-352