Selective cleavage of the Cα–Cβ linkage in lignin model compounds via Baeyer–Villiger oxidation

2015 ◽  
Vol 13 (11) ◽  
pp. 3243-3254 ◽  
Author(s):  
Nikhil D. Patil ◽  
Soledad G. Yao ◽  
Mark S. Meier ◽  
Justin K. Mobley ◽  
Mark Crocker
Keyword(s):  
Catalytic Oxidation ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Oh Groups ◽  
Selective Catalytic Oxidation ◽  
Lignin Model ◽  
Villiger Oxidation

Selective, catalytic oxidation of benzylic –OH groups followed by Baeyer–Villiger oxidation cleaves the β-O-4 linkage in lignin model compounds.

Thermal stability of lignin in ground pulp (GP) and the effect of lignin modification on GP’s thermal stability: TGA experiments with dimeric lignin model compounds and milled wood lignins

Holzforschung ◽  
2019 ◽  
Vol 73 (5) ◽  
pp. 493-499 ◽  
Author(s):  
Daisuke Ando ◽  
Fumiaki Nakatsubo ◽  
Hiroyuki Yano
Keyword(s):  
Thermal Stability ◽  
Model Compound ◽  
Pinus Densiflora ◽  
Wood Fiber ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Oh Groups ◽  
Lignin Model Compound ◽  
Lignin Model ◽  
Thermal Stability Of

Abstract For ground pulp (GP) utilization in wood fiber composites as reinforced material, its thermal behavior is relevant. The contribution of lignin to thermal performance of GP from Pinus densiflora was the focus of the present study. Dimeric lignin model compounds and isolated milled wood lignins (MWLs) from three sources were submitted for thermogravimetric analysis (TGA). The temperatures leading to 1% weight loss (T per 1% WL) for the material were determined. The thermal stability of β-O-4 models was the lowest. Among the MWLs, the abaca MWL with its high β-O-4 content was the least thermostable. An acetylated nonphenolic β-O-4 lignin model compound showed that acetylation improves the thermal stability of this type of dimeric models. The acetylation of benzylic OH groups in β-O-4 linkages is especially relevant for the thermal resistance, which was also shown based on pre-acetylated benzylic OH groups in the GP before the total acetylation.

Highly effective C–C bond cleavage of lignin model compounds

2017 ◽  
Vol 19 (13) ◽  
pp. 3135-3141 ◽  
Author(s):  
Yinling Wang ◽  
Qianyi Wang ◽  
Jianghua He ◽  
Yuetao Zhang
Keyword(s):  
Bond Cleavage ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Highly Effective ◽  
Lignin Model ◽  
Villiger Oxidation

Baeyer–Villiger oxidation is employed to effectively cleave the C–C bonds in lignin model compounds, affording multifunctional esters and phenols in excellent yields.

scholarly journals Regioselective Baeyer–Villiger oxidation of lignin model compounds with tin beta zeolite catalyst and hydrogen peroxide

RSC Advances ◽  
2017 ◽  
Vol 7 (42) ◽  
pp. 25987-25997 ◽  
Author(s):  
John A. Jennings ◽  
Sean Parkin ◽  
Eric Munson ◽  
Sean P. Delaney ◽  
Julie L. Calahan ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Zeolite Catalyst ◽  
Ester Hydrolysis ◽  
Beta Zeolite ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
System P ◽  
Benzylic Alcohol ◽  
Lignin Model ◽  
Villiger Oxidation

One approach to lignin deconstruction involves oxidation of benzylic alcohol groups, followed by Baeyer–Villiger oxidation (BVO) and ester hydrolysis. In this study β-O-4 and β-1 lignin models were oxidized using a heterogeneous BVO system.

Investigating homogeneous Co/Br−/H2O2 catalysed oxidation of lignin model compounds in acetic acid

2019 ◽  
Vol 9 (2) ◽  
pp. 384-397 ◽  
Author(s):  
Edwin B. Clatworthy ◽  
Julia L. Picone-Murray ◽  
Alexander K. L. Yuen ◽  
Richard T. Maschmeyer ◽  
Anthony F. Masters ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Catalytic Oxidation ◽  
Product Yield ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Catalysed Oxidation ◽  
Substrate Conversion ◽  
Lignin Model

The catalytic oxidation of lignin model compounds by Co/Br−/H2O2 is investigated; substituting Br− for N-hydroxyphthalimide improved substrate conversion and product yield.

Lignin to Value-Added Chemical Synthesis

2020 ◽  
Vol 16 ◽  
Author(s):  
Mahdieh Sharifi ◽  
Ramyakrishna Pothu ◽  
Rajender Boddula ◽  
Inamuddin
Keyword(s):  
Ionic Liquids ◽  
Lignocellulosic Biomass ◽  
Academic Research ◽  
Power Saving ◽  
Value Added ◽  
Glycerol Ether ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Biomass Activity ◽  
Lignin Model

Background: There is a developing demand for innovation in petroleum systems replacements. Towards this aim, lignocellulosic biomass suggested as a possible sustainable source for the manufacturing of fuels and produced chemicals. The aims of this paper are to investigate different kinds of β-O-4 lignin model compounds for the production of value-added chemicals in presence of ionic liquids. Especially, a cheap β-O-4 lignin model Guaiacol glycerol ether (GGE) (Guaifenesin) is introduced to produce valuable chemicals and novel products. Methods: Research related to chemical depolymerization of lignocellulosic biomass activity is reviewed, the notes from different methods such as thermal and microwave collected during at least 10 years. So, this collection provides a good source for academic research and it gives an efficient strategy for the manufacturing of novel value-added chemicals at an industrial scale. Results: This research presented that ionic liquid microwave-assisted is a power saving, cost efficient, fast reaction, and clean way with high selectively and purity for production of high value chemicals rather that conversional heating. Guaiacol and catechol are some of these valuable chemicals that is produced from β-O-4 lignin model compounds with high word demands that are capable to produce in industry scale. Conclusion: The β-O-4 lignin model compounds such as Guaiacol glycerol ether (GGE) (Guaifenesin) are good platform for developing food materials, perfumery, biorefinery, and pharmaceutical industry by ionic liquids-assisted lignin depolymerization method.

Insights into the electrochemical degradation of phenolic lignin model compounds in protic ionic liquid-water system

2021 ◽  
Author(s):  
Guangyong Liu ◽  
Qian Wang ◽  
Dongxia Yan ◽  
Yaqin Zhang ◽  
Chenlu Wang ◽  
...  
Keyword(s):  
Water System ◽  
Value Added ◽  
Electrochemical Degradation ◽  
Aryl Ether ◽  
Model Compounds ◽  
Protic Ionic Liquid ◽  
Lignin Model Compounds ◽  
Mild Conditions ◽  
System P ◽  
Lignin Model

Cleavage of aryl ether (Caryl-O) bonds is crucial for conversion and value-added utilization of lignin and its derivatives, but remains extremely challenging under mild conditions due to strong Caryl-O linkages....

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