Understanding acid-catalysed lignin depolymerisation process by model aromatic compound reaction kinetics

Žula, Matej; Jasiukaitytė-Grojzdek, Edita; Grilc, Miha; Likozar, Blaž

doi:10.1016/j.cej.2022.140912

Cited by 6 publications

(3 citation statements)

References 38 publications

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“…Notably, the cleavage of the CÀ O bond was considered as the SN1 reaction mechanism, [37] and the primary benzyl carbocation was considered as an important intermediate. [30] In theory, the carbocation could react with most nucleophiles because of its strong electrophilicity. [38] Thus, the carbonyl oxygen atom of acetic acid could attack the carbocation nucleophilically to form a CÀ O bond (int_3a').…”

Section: Resultsmentioning

confidence: 99%

“…[29] Sulfuric acid was also considered to be a good acid catalyst and could be used for CÀ O bond cleavage in α-O-4 lignin models with high temperatures (160-200 °C). [30] In addition to protic acid, the Lewis acid can also promote the CÀ O bond cleavage in lignin. Marks and co-workers [23] reported that metal triflate could effectively promote the activation of CÀ O bond and utilized the M(OTf) n + Pd/C system to achieve the cleavage of β-O-4 structure, obtaining the corresponding phenolic compounds and aromatic hydrocarbons.…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Cleavage of the C−O Bonds in Lignin and Lignin Model Compounds by Metal Triflate Catalysts

Zhu,

Mao,

Gao

et al. 2024

ChemSusChem

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The effective cleavage of C‐O bonds in linkages of lignin was one of the significant strategies promoting lignin valorization. Herein, the strategy of C‐O bonds cleavage of lignin using metal triflate as the catalyst was developed. The carboxylic acid or alcohol could be used as the nucleophile to stabilize the reactive intermediates formed during the depolymerization of lignin, and the corresponding ester/ether compounds could be obtained. This catalytic system was suitable for the C‐O bond cleavage in α‐O‐4 and β‐O‐4 linkages with excellent efficiency. Additionally, reaction conditions were optimized. The reaction mixture was detected by 1H NMR, and no other byproducts were found. As for treated lignin samples, the cleavage of C‐O bonds in linkages was determined by 2D HSQC NMR，the increased content of the phenol hydroxyl group was proved by FT‐IR, and the reduced molecular weight was investigated by GPC. Furthermore, multiple phenolic compounds were detected by GC‐MS in the reaction mixtures.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Catalytic Cleavage of the C−O Bonds in Lignin and Lignin Model Compounds by Metal Triflate Catalysts

Zhu,

Mao,

Gao

et al. 2024

ChemSusChem

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“…Due to their chemical structures, cellulose and hemicellulose can be hydrolysed to monosaccharides, and subsequently converted into biofuel. Lignin is a complex heteropolymer with a non-crystalline and irregular three-dimensional structure, which is mainly composed of three primary units, namely, syringyl (S), guaiacyl (G) and p -hydroxyphenyl (H) units, highly relevant for green chemistry applications, as it is considered the primary renewable feedstock for the sustainable production of aromatic chemicals ( Gillet et al, 2017 ; Ročnik et al, 2022 ; Žula et al, 2023 ). Lignin is the first barrier to the full utilisation of the polysaccharide portion of the biomass.…”

Section: Introductionmentioning

confidence: 99%

Challenging DESs and ILs in the valorization of food waste: a case study

Mero,

Moody,

Husanu

et al. 2023

Front. Chem.

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In this study, the efficacy of two of the best performing green solvents for the fractionation of lignocellulosic biomass, cholinium arginate (ChArg) as biobased ionic liquid (Bio-IL) and ChCl:lactic acid (ChCl:LA, 1:10) as natural deep eutectic solvent (NADES), was investigated and compared in the pretreatment of an agri-food industry waste, apple fibers (90°C for 1 h). For the sake of comparison, 1-butyl-3-methylimidazolium acetate (BMIM OAc) as one of the best IL able to dissolve cellulose was also used. After the pretreatment, two fractions were obtained in each case. The results gathered through FTIR and TG analyses of the two materials and the subsequent DNS assay performed after enzymatic treatment led to identify ChArg as the best medium to delignify and remove waxes, present on the starting apple fibers, thus producing a material substantially enriched in cellulose (CRM). Conversely, ChCl:LA did not provide satisfactorily results using these mild conditions, while BMIM OAc showed intermediate performance probably on account of the reduced crystallinity of cellulose after the dissolution-regeneration process. To corroborate the obtained data, FTIR and TG analyses were also performed on the residues collected after the enzymatic hydrolysis. At the end of the pretreatment, ChArg was also quantitatively recovered without significant alterations.

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Combination of linear solvation energy and linear free-energy relationships to aid the prediction of reaction kinetics: Application to the solvolysis of 5-HMF by alcohol to levulinate

Munoz,

Di Menno Di Bucchianico,

Devouge-Boyer

et al. 2024

Chemical Engineering Research and Design

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Understanding acid-catalysed lignin depolymerisation process by model aromatic compound reaction kinetics

Cited by 6 publications

References 38 publications

Catalytic Cleavage of the C−O Bonds in Lignin and Lignin Model Compounds by Metal Triflate Catalysts

Catalytic Cleavage of the C−O Bonds in Lignin and Lignin Model Compounds by Metal Triflate Catalysts

Challenging DESs and ILs in the valorization of food waste: a case study

Combination of linear solvation energy and linear free-energy relationships to aid the prediction of reaction kinetics: Application to the solvolysis of 5-HMF by alcohol to levulinate

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