145804-82-6Relevant academic research and scientific papers
Catalytic C-O bond cleavage of 2-aryloxy-1-arylethanols and its application to the depolymerization of lignin-related polymers
Nichols, Jason M.,Bishop, Lee M.,Bergman, Robert G.,Ellman, Jonathan A.
, p. 12554 - 12555 (2010)
A ruthenium-catalyzed, redox neutral C-O bond cleavage of 2-aryloxy-1-arylethanols was developed that yields cleavage products in 62-98% isolated yield. This reaction is applicable to breaking the key ethereal bond found in lignin-related polymers. The bond transformation proceeds by a tandem dehydrogenation/reductive ether cleavage. Initial mechanistic investigations indicate that the ether cleavage is most likely an organometallic C-O activation. A catalytic depolymerization of a lignin-related polymer quantitatively yields the corresponding monomer with no added reagent.
Catalytic C–O bond cleavage in a β-O-4 lignin model through intermolecular hydrogen transfer
Ahsan Usman, Muhammad,Naeem, Maham,Saeed, Muhammad,Zaheer, Muhammad
, (2021/03/22)
A base-free and redox neutral approach for the selective breaking of aryl ether bond (C–O) contained by a lignin model compound mimicking a β-O-4 linkage is reported. A palladium loaded metal-organic framework (MOF) was used as a catalyst for this purpose. The reaction proceeds through dehydrogenation of benzylic alcohol moiety followed by the hydrogenolysis of the ether bonds. Therefore, no external hydrogen source is required for the reaction to take place.
Visible-light-induced C-C bond cleavage of lignin model compounds with cyanobenziodoxolone
Zheng, Ming,Huang, Yan,Zhan, Le-Wu,Hou, Jing,Li, Bin-Dong
supporting information, (2020/10/02)
The catalytic degradation of lignin to value-added chemicals has received considerable attention over the past decade. Photocatalysis provides promising approaches to enable previously inaccessible transformations. However, examples of the visible-light promoted degradation of lignin are still limited. In this work, the visible-light-induced selective C-C bond cleavage of β-O-4 lignin model compounds has been disclosed via β-scission of in situ generated alkoxy radical intermediates. With cyanobenziodoxolone as the oxidant, a variety of substrates could be transformed into aldehydes in moderate to good yields. In addition, unexpected acetal esters which could conveniently furnish formaldehyde and phenols by alcoholysis were observed.
Oxidative cleavage of β-O-4 bonds in lignin model compounds with a single-atom Co catalyst
Liu, Sijie,Bai, Lichen,Van Muyden, Antoine P.,Huang, Zhangjun,Cui, Xinjiang,Fei, Zhaofu,Li, Xuehui,Hu, Xile,Dyson, Paul J.
supporting information, p. 1974 - 1981 (2019/04/29)
Single-atom catalysts are emerging as primary catalysts for many reactions due to their 100% utilization of active metal centers leading to high catalytic efficiencies. Herein, we report the use of a single-atom Co catalyst for the oxidative cleavage of the β-O-4 bonds of lignin model compounds at a low oxygen pressure. Under the optimized reaction conditions, the conversion of 2-(2-methoxyphenoxy)-1-phenylethanol up to 95% with high selectivities was achieved with a variety of substrates investigated. The reusability of the Co catalyst with a high catalytic efficiency indicates its potential application in the oxidative cleavage of C-O bonds.
Au-Pd alloy cooperates with covalent triazine frameworks for the catalytic oxidative cleavage of β-O-4 linkages
Zhao, Li,Shi, Song,Zhu, Guozhi,Liu, Meng,Gao, Jin,Xu, Jie
supporting information, p. 6707 - 6716 (2019/12/26)
To design highly efficient catalysts for the cleavage of the C-O/C-C bond is the key task in the depolymerization of lignin. Bimetallic alloy catalysts Au-Pd-CTFs were developed to be effective in the oxidative cleavage of β-O-4 lignin model compounds with O2. Au-Pd nanoparticles with an Au/Pd molar ratio between 1?:?1 and 1?:?1.5 showed the highest cleavage efficiency. The kinetics of the reaction process revealed that a synergistic effect between Au and Pd played a crucial role in the oxidation of Cα-OH into CαO, which was the rate-determining step for the whole oxidative cleavage process. Further insight revealed that the cooperative effect between Au-Pd nanoparticles and the support covalent triazine frameworks (CTFs) facilitated the cleavage of the formed β-O-4 ketone compound to the corresponding aromatics. In addition, Au-Pd-CTF catalysts also showed efficiency in the oxidative transformation of the organosolv lignin. This catalytic system will provide guidance in the oxidative cleavage of β-O-4 linkages in lignin.
Facile and selective hydrogenolysis of β-O-4 linkages in lignin catalyzed by Pd-Ni bimetallic nanoparticles supported on ZrO2
Zhang, Jia-Wei,Cai, Yao,Lu, Guo-Ping,Cai, Chun
supporting information, p. 6229 - 6235 (2016/12/03)
The β-O-4 linkage in lignin can be selectively cleaved by Pd-Ni bimetallic nanoparticles supported on ZrO2 using hydrogen gas as the hydrogen donor under ambient pressure and neutral conditions. Conspicuous enhancement in activity is observed compared with single nickel and palladium catalysts based on the results of experiments and characterization. Moreover, hydrogenation of the produced phenols is tuned by adjusting the amount of NaBH4. The catalyst can be reused over ten times in the model reaction and over five times in the hydrogenolysis of lignin without an obvious change in activity and selectivity.
Highly efficient, NiAu-catalyzed hydrogenolysis of lignin into phenolic chemicals
Zhang, Jiaguang,Asakura, Hiroyuki,Van Rijn, Jeaphianne,Yang, Jun,Duchesne, Paul,Zhang, Bin,Chen, Xi,Zhang, Peng,Saeys, Mark,Yan, Ning
supporting information, p. 2432 - 2437 (2014/05/06)
A highly efficient, stable NiAu catalyst that exhibits unprecedented low temperature activity in lignin hydrogenolysis was for the first time developed, leading to the formation of 14 wt% aromatic monomers from organosolv lignin at 170 °C in pure water. the Partner Organisations 2014.
