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.

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....

Selective Aerobic Benzylic Alcohol Oxidation of Lignin Model Compounds: Route to Aryl Ketones

ChemCatChem ◽  
2014 ◽  
Vol 7 (3) ◽  
pp. 401-404 ◽  
Author(s):  
Monali Dawange ◽  
Maxim V. Galkin ◽  
Joseph S. M. Samec
Keyword(s):  
Alcohol Oxidation ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Benzylic Alcohol ◽  
Aryl Ketones ◽  
Lignin Model

The Reactions of Lignin Model Compounds with Hydrogen Peroxide at Low pH

Holzforschung ◽  
2003 ◽  
Vol 57 (1) ◽  
pp. 52-88 ◽  
Author(s):  
T. Kishimoto ◽  
J. F. Kadla ◽  
H.-m. Chang ◽  
H. Jameel
Keyword(s):  
Hydrogen Peroxide ◽  
Reaction System ◽  
Model Compounds ◽  
Reaction Conditions ◽  
Lignin Model Compounds ◽  
Lignin Model Compound ◽  
Lignin Model ◽  
Decreasing Ph ◽  
Hydroxyl Compounds ◽  
Acidic Hydrogen

Summary In peroxymonosulfuric acid bleaching, the presence of hydrogen peroxide is dependent on the reaction conditions and the conversion ratios used to generate the peroxy acid. Substantial amounts of hydrogen peroxide may be present in the reaction system under certain conditions. An understanding of the reactions of hydrogen peroxide under these conditions would be beneficial. Therefore, several simple lignin model compounds were reacted with acidic hydrogen peroxide, pH 1-3, at 70°C. In all cases the phenolic lignin model compounds reacted much faster than their non-phenolic counterparts. In fact, the extent of reaction was very much dependent on the structure of the lignin model compound. The α-hydroxyl compounds, 4-(1-Hydroxy-ethyl)-2-methoxy-phenol and 1-(3,4-Dimethoxy-phenyl)-ethanol, reacted faster than the corresponding α-carbonyl compounds with both reacting much faster than the aromatic compounds, with simple alkyl substituents. A new reaction mechanism for α-hydroxyl compounds is proposed, in which benzyl carbocation formation is followed by nucleophilic addition of hydrogen peroxide. Unlike the mechanisms proposed in the past, no evidence of aromatic hydroxylation via perhydronium ion was observed. The reactivities were very pH dependent, in that higher reactivity was associated with lower pH. Decreasing pH further increased the amount of condensation products identified, such that condensation was competitive with degradation. These condensation reactions were also present under the Caro's acid bleaching conditions at pH below 2. However, under all conditions the reactivity of acidic peroxide was found to be much less than that of peroxymonosulfuric acid.

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.

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