Efficient Cobalt-Catalyzed Oxidative Conversion of Lignin Models to Benzoquinones

被引:117
作者
Biannic, Berenger [1 ]
Bozell, Joseph J. [1 ]
机构
[1] Univ Tennessee, Ctr Renewable Carbon, C3Bio, Knoxville, TN 37917 USA
关键词
O BOND-CLEAVAGE; PARASUBSTITUTED PHENOLS; STRUCTURAL-CHANGES; KRAFT COOKING; ARYL ETHERS; COMPLEXES; CHEMICALS; HYDROGENOLYSIS; DEGRADATION; GUAIACOL;
D O I
10.1021/ol401065r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phenolic lignin model monomers and dimers representing the primary substructural units of lignin were successfully oxidized to benzoquinones in high yield with molecular oxygen using new Co-Schiff base catalysts bearing a bulky heterocyclic nitrogen base as a substituent. This is the first example of a catalytic system able to convert both S and G lignin model phenols in high yield, a process necessary for effective use of lignin as a chemical feedstock.
引用
收藏
页码:2730 / 2733
页数:4
相关论文
共 33 条
[1]   Lignin biosynthesis [J].
Boerjan, W ;
Ralph, J ;
Baucher, M .
ANNUAL REVIEW OF PLANT BIOLOGY, 2003, 54 :519-546
[2]   COBALT-SCHIFF BASE COMPLEX-CATALYZED OXIDATION OF PARASUBSTITUTED PHENOLICS - PREPARATION OF BENZOQUINONES [J].
BOZELL, JJ ;
HAMES, BR ;
DIMMEL, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) :2398-2404
[3]   Feedstocks for the future - Biorefinery production of chemicals from renewable carbon [J].
Bozell, Joseph J. .
CLEAN-SOIL AIR WATER, 2008, 36 (08) :641-647
[4]   Biomass Fractionation for the Biorefinery: Heteronuclear Multiple Quantum Coherence-Nuclear Magnetic Resonance Investigation of Lignin Isolated from Solvent Fractionation of Switchgrass [J].
Bozell, Joseph J. ;
O'Lenick, C. J. ;
Warwick, Stacy .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2011, 59 (17) :9232-9242
[5]   Technology development for the production of biobased products from biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited [J].
Bozell, Joseph J. ;
Petersen, Gene R. .
GREEN CHEMISTRY, 2010, 12 (04) :539-554
[6]   Catalytic oxidation of para-substituted phenols with cobalt-Schiff base complexes/O2-selective conversion of syringyl and guaiacyl lignin models to benzoquinones [J].
Cedeno, Diana ;
Bozell, Joseph J. .
TETRAHEDRON LETTERS, 2012, 53 (19) :2380-2383
[7]   Metal-Salen Schiff base complexes in catalysis: practical aspects [J].
Cozzi, PG .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (07) :410-421
[8]   ALLYLATION AND OXIDATION REACTIONS PROMOTED BY COBALT(II) COMPLEXES [J].
GAUDEMER, A ;
NGUYENVANDUONG, K ;
SHAHKARAMI, N ;
ACHI, SS ;
FROSTINRIO, M ;
PUJOL, D .
TETRAHEDRON, 1985, 41 (19) :4095-4106
[9]  
GELLERSTEDT G, 1984, SVEN PAPPERSTIDN, V87, pR115
[10]   C-C or C-O Bond Cleavage in a Phenolic Lignin Model Compound: Selectivity Depends on Vanadium Catalyst [J].
Hanson, Susan K. ;
Wu, Ruilian ;
Silks, Louis A. Pete .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (14) :3410-3413