Tandem conversion of lignin to catechols via demethylation and catalytic hydrogenolysis

被引:33
作者
Kim, Kwang Ho [1 ,2 ]
Jeong, Keunhong [3 ]
Zhuang, Jingshun [4 ]
Jeong, Hye Jin [3 ]
Kim, Chang Soo [1 ]
Koo, Bonwook [5 ]
Yoo, Chang Geun [4 ]
机构
[1] Korea Inst Sci & Technol, Clean Energy Res Ctr, Seoul 02702, South Korea
[2] Univ British Columbia, Dept Wood Sci, Vancouver, BC V6T 1Z4, Canada
[3] Korea Mil Acad, Dept Chem, Seoul 01805, South Korea
[4] SUNY Coll Environm Sci & Forestry, Dept Paper & Bioproc Engn, Syracuse, NY 13210 USA
[5] Korea Inst Ind Technol, Green & Sustainable Mat R&D Dept, Cheonan 31056, South Korea
基金
新加坡国家研究基金会;
关键词
Tandem reaction; Lignin valorization; Platform chemical; Depolymerization; Structural modification; DEPOLYMERIZATION; PYROLYSIS; OXIDATION; ACID; VALORIZATION; CHEMICALS;
D O I
10.1016/j.indcrop.2020.113095
中图分类号
S2 [农业工程];
学科分类号
0828 ;
摘要
Lignin is regarded as a potential source of various aromatic compounds and chemicals, replacing petrochemicals. Catechol and its derivatives are important platform chemicals in many industrial sectors, including agrochemicals and pharmaceuticals. The global market of catechols is expected to increase with emerging demand in end-use industries. Considering that the current production of catechols relies on fossil fuels, it is critical to seek alternative renewable sources to respond to sustainability challenges. In this respect, lignin is viewed as a promising material due to its abundance and renewable character. Also, the structural similarity to catechols has made lignin a potential feedstock for the production of bio-catechols. However, the lignin-to-catechols conversion approach is still in an early stage because the intractable nature of lignin and the complex mixture of the depolymerized products make its valorization less feasible. Herein, we report a selective production of catechols via tandem conversion of lignin, namely, demethylation followed by catalytic hydrogenolysis (DFCH). The DFCH of lignin resulted in catechol- and catechol derivatives-rich liquid, accounting for 80 % in the identified products. The reaction mechanisms were also studied by quantum calculations to provide a fundamental understanding of the conversion. The result proves that selective modification of lignin structure is a promising approach to produce specific platform chemicals, providing insights toward an efficient strategy for lignin valorization.
引用
收藏
页数:8
相关论文
共 47 条
[1]   Gas- and solid/liquid-phase reactions during pyrolysis of softwood and hardwood lignins [J].
Asmadi, Mohd ;
Kawamoto, Haruo ;
Saka, Shiro .
JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, 2011, 92 (02) :417-425
[2]   Thermal reactivities of catechols/pyrogallols and cresols/xylenols as lignin pyrolysis intermediates [J].
Asmadi, Mohd ;
Kawamoto, Haruo ;
Saka, Shiro .
JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, 2011, 92 (01) :76-87
[3]   Catechol biosynthesis from glucose in Escherichia coli anthranilate-overproducer strains by heterologous expression of anthranilate 1,2-dioxygenase from Pseudomonas aeruginosa PAO1 [J].
Balderas-Hernandez, Victor E. ;
Trevino-Quintanilla, Luis G. ;
Hernandez-Chavez, Georgina ;
Martinez, Alfredo ;
Bolivar, Francisco ;
Gosset, Guillermo .
MICROBIAL CELL FACTORIES, 2014, 13
[4]  
Barner B.A., 2004, Encyclopedia of Reagents for Organic Synthesis
[5]  
Barone V., 2014, GAUSSIAN 09 REVISION
[6]   Depolymerization of organosolv lignin to aromatic compounds over Cu-doped porous metal oxides [J].
Barta, Katalin ;
Warner, Genoa R. ;
Beach, Evan S. ;
Anastas, Paul T. .
GREEN CHEMISTRY, 2014, 16 (01) :191-196
[7]  
Behling R, 2016, GREEN CHEM, V18, P1839, DOI [10.1039/C5GC03061G, 10.1039/c5gc03061g]
[8]  
Bjorkman A., 1956, SVEN PAPPERSTIDN, V59, P477, DOI DOI 10.1016/J.CHROMA.2003.08.046
[9]   Catalytic depolymerisation of isolated lignins to fine chemicals using a Pt/alumina catalyst: part 1-impact of the lignin structure [J].
Bouxin, Florent P. ;
McVeigh, Ashley ;
Tran, Fanny ;
Westwood, Nicholas J. ;
Jarvis, Michael C. ;
Jackson, S. David .
GREEN CHEMISTRY, 2015, 17 (02) :1235-1242
[10]   CATECHOL AND CHLOROCATECHOLS IN SOIL - DEGRADATION AND EXTRACTABILITY [J].
CHENG, HH ;
HAIDER, K ;
HARPER, SS .
SOIL BIOLOGY & BIOCHEMISTRY, 1983, 15 (03) :311-317