LIGNIN MODEL COMPOUNDS: II. PREPARATION AND PROPERTIES OF 1-HYDROXY-1-(4-HYDROXY-3-METHOXYPHENYL)-2-PROPANONE

1962 ◽  
Vol 40 (8) ◽  
pp. 1672-1677 ◽  
Author(s):  
J. A. F. Gardner ◽  
D. W. Henderson ◽  
Harold MacLean
Keyword(s):  
Phenolic Compound ◽  
Catalytic Hydrogenation ◽  
Vanillic Acid ◽  
Reference Sample ◽  
The Other ◽  
Model Compounds ◽  
Solvent Fractionation ◽  
Lignin Model Compounds ◽  
Hydrolysis Products ◽  
Lignin Model

Modern concepts of lignin structure suggest that the ketol 1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-propanone, VI, should be detectable in the hydrolysis products of lignin and wood. A reference sample of VI, previously unavailable, has now been prepared by catalytic hydrogenation of the diketone 1-(4-hydroxy-3-methoxyphenyl)-1,2-propanedione, II. Both fermentative and catalytic hydrogenation of II gave mixtures of, according to paper chromatography, mainly 2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone, V; the desired ketol, VI; small amounts of vanillic acid; and traces of guaiacyl acetone and an unknown phenolic compound. The ketol VI was isolated from the catalytic hydrogenation products by solvent fractionation and was identified by absorption spectra, derivatives, and comparison with the other two possible isomeric ketols. Dilute alkali converted VI to the isomeric ketol V. Both ethanolysis and acidolysis of VI gave the same monomeric products as lignin.

Acid hydrolysis kinetics and identification of erythro and threo α-ethyl ether derivatives of non-phenolic arylglycerol-β-syringyl ether lignin model compounds

Holzforschung ◽  
2005 ◽  
Vol 59 (5) ◽  
pp. 497-502 ◽  
Author(s):  
Hiroshi Ohi ◽  
Masanori Kishino
Keyword(s):  
Ethyl Ether ◽  
Nmr Spectra ◽  
Least Squares Method ◽  
The Other ◽  
Hydrolysis Kinetics ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Molar Ratios ◽  
Lignin Model ◽  
Derivatives Of

Abstract Based on their hydrolysis behavior, NMR spectra of the erythro and threo forms of 3-(3,4-dimethoxy-phenyl)-2-(2,6-dimethoxyphenoxy)-3-ethoxypropan-1-ol (named VSE, i.e., α-ethyl ether derivative of veratrylglycerol-β-syringylether) were successfully assigned. A mixture of erythro and threo VSEs was treated at 90°C in pH 1.2 nitric acid solution. In order to assign them, the molar ratios of erythro and threo forms of 1-(3,4-dimethoxyphenyl)-2-(2,6-dimethoxy-phenoxy)propane-1,3-diol (named VS, i.e., veratrylglycerol-β-syringyl) ether given by each VSE were kinetically determined during the treatment. It was found that the inversion ratio at which the first VSE isomer gave erythro-VS was 0.73. Therefore, this isomer was identified as threo-VSE. In addition, from calculations using the least-squares method, the inversion ratio at which the other VSE isomer gave threo-VS was found to be >0.73. These values mean that threo-VSE yields 73% erythro- and 27% threo-VS, while erythro-VSE yields mainly threo-VS.

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....

Eco-friendly preparation of ultrathin biomass-derived Ni3S2-doped carbon nanosheets for selective hydrogenolysis of lignin model compounds in the absence of hydrogen

2021 ◽  
Vol 23 (8) ◽  
pp. 3090-3103
Author(s):  
Changzhou Chen ◽  
Dichao Wu ◽  
Peng Liu ◽  
Jing Li ◽  
Haihong Xia ◽  
...  
Keyword(s):  
Model Compounds ◽  
Lignin Model Compounds ◽  
Carbon Nanosheets ◽  
Significant Potential ◽  
Selective Hydrogenolysis ◽  
Lignin Model

Lignin is an abundant source of aromatics, and the depolymerization of lignin provides significant potential for producing high-value chemicals.

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