scholarly journals Studies on the Cooking Mechanism of Wood. XV. Mannich Reaction on Lignin Model Compounds and the Estimation of the Amount of the Simple Guaiacyl Nucleus in Thiolignin

1956 ◽  
Vol 29 (2) ◽  
pp. 259-265 ◽  
Author(s):  
Hiroshi Mikawa ◽  
Koichiro Sato ◽  
Chizuko Takasaki ◽  
Kiyo Ebisawa
Keyword(s):  
Mannich Reaction ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Lignin Model

Article

1998 ◽  
Vol 76 (5) ◽  
pp. 612-622
Author(s):  
Zhi-Hua Jiang ◽  
Dimitris S Argyropoulos
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Quantitative Analysis ◽  
Magnetic Resonance ◽  
Mannich Reaction ◽  
Phenolic Hydroxyl ◽  
Ambient Conditions ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Lignin Model ◽  
The Mannich Reaction

The reactivity of lignin model compounds under Mannich conditions with piperidine and formaldehyde was studied. The piperidinomethyl group was confirmed to be introduced quantitatively at sterically unhindered positions ortho to a phenolic hydroxyl when the substrate was allowed to react under ambient conditions. The sequential application of the Mannich reaction followed by quantitative 31P NMR on a variety of lignin samples allowed the amounts of various aromatic groups bearing free phenolic hydroxyls to be determined. More specifically, the technique allowed the quantification of para-hydroxyl phenols, catechols, guaiacols, and phenols bearing C5 or C6 substituents. The quantitative reliability of the technique was also examined with a series of dissolved kraft lignins, isolated at various degrees of delignification. The data were found to favourably compare to those obtained by permanganate oxidation.Key words: lignin, lignin model compounds, Mannich reaction, nuclear magnetic resonance (NMR), phenols, phosphorus, piperidine, quantitative analysis.

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.

Chromophore production in lignin model compounds — Anaerobic reactions

1995 ◽  
Vol 21 (3-5) ◽  
pp. 353-371 ◽  
Author(s):  
N. A. Weir ◽  
J. Arct ◽  
A. Ceccarelli
Keyword(s):  
Model Compounds ◽  
Lignin Model Compounds ◽  
Lignin Model

Studies on electrooxidation of lignin and lignin model compounds. Part 1: Direct electrooxidation of non-phenolic lignin model compounds

Holzforschung ◽  
2012 ◽  
Vol 66 (3) ◽  
Author(s):  
Takumi Shiraishi ◽  
Toshiyuki Takano ◽  
Hiroshi Kamitakahara ◽  
Fumiaki Nakatsubo
Keyword(s):  
Electron Transfer ◽  
Cyclic Voltammetry ◽  
Carbonyl Compounds ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Bulk Electrolysis ◽  
Lignin Model ◽  
Dimeric Compound ◽  
High Yields ◽  
Short Time

Abstract The direct anodic oxidation of non-phenolic lignin model compounds was investigated to understand their basic behaviors. The results of cyclic voltammetry (CV) studies of monomeric model, such as 1-(4-ethoxy-3-methoxyphenyl)ethanol, are interpreted as the oxidation for Cα-carbonylation did not proceed in the reaction without a catalyst, but a base promotes this reaction. Indeed, the bulk electrolyses of the monomeric lignin model compounds with 2,6-lutidine afforded the corresponding Cα-carbonyl compounds in high yields (60–80%). It is suggested that deprotonation at Cα-H in the ECEC mechanism (E=electron transfer and C=chemical step) is important for Cα-carbonylation. In the uncatalyzed bulk electrolysis of a β-O-4 model dimeric compound, 4-ethoxy-3-methoxyphenylglycerol-β-guaiacyl ether, the corresponding Cα-carbonyl compound was not detected but as a result of Cα-Cβcleavage 4-O-ethylvanillin was found in 40% yield. In the electrolysis reaction in the presence of 2,6-lutidine (as a sterically hindered light base), the reaction stopped for a short time unexpectedly. These results indicate the different electrochemical behavior of simple monomeric model compounds and dimeric β-O-4 models. The conclusion is that direct electrooxidation is unsuitable for Cα-carbonylation of lignin.

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