Cleavage of the β–O–4 bond in a lignin model compound using the acidic ionic liquid 1-H-3-methylimidazolium chloride as catalyst: a DFT mechanistic study

Ionic ligands derived from a salen ligand containing two proximal 1,3-disubstituted imidazolium ionic liquid cores form cobalt(III) complexes capable of selectively oxidizing veratryl alcohol, a lignin model compound, to veratraldehyde using air as the source of oxygen. These complexes are easy to prepare, inexpensive, water stable, and soluble in ionic liquids, making them viable candidates for use as oxidation catalysts.

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Degradation of a Lignin Model Compound by ROS Generated In Situ through Controlled ORR in Ionic Liquid

Journal of The Electrochemical Society ◽

10.1149/1945-7111/abd518 ◽

2021 ◽

Vol 168 (1) ◽

pp. 016504

Author(s):

Haomin Jiang ◽

Yujuan Cheng ◽

Zhaohui Wang ◽

Zhiqun Bai ◽

Yang Tang ◽

...

Keyword(s):

Ionic Liquid ◽

Model Compound ◽

Lignin Model Compound ◽

Lignin Model

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Free radical reaction promoted by ionic liquid: a route for metal-free oxidation depolymerization of lignin model compound and lignin

Chemical Communications ◽

10.1039/c4cc10394g ◽

2015 ◽

Vol 51 (19) ◽

pp. 4028-4031 ◽

Cited By ~ 49

Author(s):

Yingying Yang ◽

Honglei Fan ◽

Jinliang Song ◽

Qinglei Meng ◽

Huacong Zhou ◽

...

Keyword(s):

Ionic Liquid ◽

Model Compound ◽

Radical Reaction ◽

Free Radical Reaction ◽

Model Compounds ◽

Lignin Model Compounds ◽

Lignin Model Compound ◽

Organosolv Lignin ◽

Lignin Model ◽

Free Oxidation

Ionic liquid can efficiently promote the transformation of lignin model compounds and organosolv lignin.

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Decomposition of a phenolic lignin model compound over organic N-bases in an ionic liquid

Holzforschung ◽

10.1515/hf.2010.075 ◽

2010 ◽

Vol 64 (5) ◽

Cited By ~ 31

Author(s):

Songyan Jia ◽

Blair J. Cox ◽

Xinwen Guo ◽

Z. Conrad Zhang ◽

John G. Ekerdt

Keyword(s):

Ionic Liquid ◽

Model Compound ◽

Bond Cleavage ◽

Organic N ◽

Alkyl Ether ◽

Cleavage Reaction ◽

Process Step ◽

Lignin Model Compound ◽

Lignin Model ◽

Lignin Depolymerization

Abstract Lignin depolymerization is a necessary process step in utilizing the carbohydrates in biomass and in potentially converting the lignin into a chemical feedstock. Lignin contains several aryl-alkyl ether linkages and the β-O-4 linkage is dominant among lignins. Base-mediated cleavage of the β-O-4 bond in a lignin model compound, guaiacylglycerol-β-guaiacyl ether, is reported. Ionic liquids have shown promise in a variety of biomass processes and this study explores the potential to use an ionic liquid solvent (1-butyl-2,3-dimethylimidazolium chloride) and non-aqueous bases in cleaving the β-O-4 bond. N-bases of varying basicity and structure were used at temperatures up to 150°C. The cleavage reaction was not found to be catalytic. Among all the tested N-bases, 1,5,7-triazabicyclo[4.4.0]dec-5-ene was the most active, leading to more than 40% β-O-4 ether bond cleavage, and the higher activity is probably associated with the exposed nature of the N-atoms.

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Electrochemical Generation of ROS in Ionic Liquid for the Degradation of Lignin Model Compound

Journal of The Electrochemical Society ◽

10.1149/2.0801811jes ◽

2018 ◽

Vol 165 (11) ◽

pp. H705-H710 ◽

Cited By ~ 7

Author(s):

Lei Wang ◽

Shuangyan Liu ◽

Haomin Jiang ◽

Yueying Chen ◽

Linan Wang ◽

...

Keyword(s):

Ionic Liquid ◽

Model Compound ◽

Electrochemical Generation ◽

Lignin Model Compound ◽

Lignin Model

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Recyclable ionic liquid tagged Co(salen) catalysts for the oxidation of lignin model compounds

Canadian Journal of Chemistry ◽

10.1139/cjc-2013-0336 ◽

2013 ◽

Vol 91 (12) ◽

pp. 1258-1261 ◽

Cited By ~ 14

Author(s):

Kenson Ambrose ◽

Bitu B. Hurisso ◽

Robert D. Singer

Keyword(s):

Ionic Liquid ◽

Liquid Phase ◽

Model Compound ◽

Veratryl Alcohol ◽

Pure Oxygen ◽

Model Compounds ◽

Imidazolium Ionic Liquid ◽

Lignin Model Compounds ◽

Lignin Model Compound ◽

Lignin Model

Ionic liquid tagged salen ligands containing two proximal 1,3-disubstituted imidazolium ionic liquid cores form cobalt(III) complexes capable of selectively oxidizing veratryl alcohol, a lignin model compound, to veratraldehyde using air or pure oxygen as the source of oxygen. Entrainment of these catalysts in either 1-butyl-3-methylimidazolium hexafluorophosphate, [bmim][PF6], or 1-butyl-3-methylimidazolium bistriflimide, [bmim][NTf2], hydrophobic ionic liquid solvents, results in biphasic reactions when water is used as the second solvent allowing the catalyst/ionic liquid phase to be recycled.

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