Iron porphyrin catalyzed oxidation of lignin model compounds: oxidation of phenylpropane and phenylpropene model compounds

1995 ◽  
Vol 73 (12) ◽  
pp. 2153-2157 ◽  
Author(s):  
Futong Cui ◽  
David Dolphin
Keyword(s):  
Iron Chloride ◽  
Ring Cleavage ◽  
Iron Porphyrin ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Aqueous Acetonitrile ◽  
Tert Butylhydroperoxide ◽  
Lignin Model ◽  
Aromatic Ring Cleavage ◽  
Catalyzed Oxidation

The oxidation of 1-(4-ethoxy-3-methoxyphenyl)propane (2) and 1-(4-ethoxy-3-methoxyphenyl)propene (3) by meso-tetra(2,6-dichloro-3-sulphonatophenyl)porphyrin iron chloride (TDCSPPFeCl, 1) and tert-butylhydroperoxide (t-BuOOH) are discussed. In addition to a Cα-hydroxylation product, demethoxylation and direct aromatic ring cleavage products were found in the oxidation of 2. When 3 was oxidized by 1 and t-BuOOH in aqueous acetonitrile, an acetonitrile-incorporated product was found. A mechanism for the oxidation of 3 is proposed. Keywords: lignin, ligninase, iron porphyrin, model, degradation.

Iron porphyrin catalyzed oxidation of lignin model compounds: the oxidation of veratryl alcohol and veratryl acetate

1992 ◽  
Vol 70 (8) ◽  
pp. 2314-2318 ◽  
Author(s):  
Futong Cui ◽  
David Dolphin
Keyword(s):  
Aqueous Solution ◽  
Veratryl Alcohol ◽  
Cleavage Product ◽  
Iron Chloride ◽  
Ring Cleavage ◽  
Model Compounds ◽  
Lignin Model ◽  
Mechanism Of Oxidation ◽  
Catalyzed Oxidation ◽  
Insight Into

meso-Tetra(2,6-dichloro-3-sulfonatophenyl)porphyrin iron chloride catalyzes the oxidation of 3,4-dimethoxybenzyl alcohol (veratryl alcohol) in aqueous solution to give veratraldehyde along with demethoxylation and ring-cleavage products. The isolation of a direct ring-cleavage product from the oxidation of veratryl acetate in aqueous solution supports the previously proposed ring-cleavage mechanisms. The oxidation in methanol, however, does not lead to ring-cleavage products. When veratryl alcohol was oxidized in methanol, solvent was found to be incorporated into the 3-position of veratryl alcohol, giving new insight into the mechanism of oxidation.

Phenolic mediators enhance the manganese peroxidase catalyzed oxidation of recalcitrant lignin model compounds and synthetic lignin

2014 ◽  
Vol 72 ◽  
pp. 137-149 ◽  
Author(s):  
Paula Nousiainen ◽  
Jussi Kontro ◽  
Helmiina Manner ◽  
Annele Hatakka ◽  
Jussi Sipilä
Keyword(s):  
Manganese Peroxidase ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Lignin Model ◽  
Catalyzed Oxidation

Mechanistic studies on the VO(acac)2-catalyzed oxidative cleavage of lignin model compounds in acetic acid

RSC Advances ◽  
2016 ◽  
Vol 6 (111) ◽  
pp. 110229-110234 ◽  
Author(s):  
Yangyang Ma ◽  
Zhongtian Du ◽  
Fei Xia ◽  
Jiping Ma ◽  
Jin Gao ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Reaction Pathway ◽  
Aerobic Oxidation ◽  
Oxidative Cleavage ◽  
Mechanistic Studies ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Lignin Model ◽  
Selective Aerobic Oxidation ◽  
Catalyzed Oxidation

Selective aerobic oxidation has provided a promising approach for breaking lignin into smaller aromatics. Here, the reaction pathway of VO(acac)2-catalyzed oxidation of lignin model 2-phenoxy-1-phenylethanol in acetic acid was studied.

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.

Sign in / Sign up

Export Citation Format

Share Document