Kraft Lignin Depolymerization in an Ionic Liquid without a Catalyst

Diop, Amadou; Jradi, Khalil; Daneault, Claude; Montplaisir, Daniel

doi:10.15376/biores.10.3.4933-4946

Cited by 34 publications

(12 citation statements)

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“…(for the full 1 H NMR spectra of the samples studied see Supplementary Material). These results are in full agreement with the study performed on Kraft lignin by Diop et al [31].…”

Section: A) Ir Bands Assignments For Lignin B) Ir Bands Assignments Fsupporting

confidence: 93%

Effect of Four Novel Bio-Based DES (Deep Eutectic Solvents) on Hardwood Fractionation

et al. 2020

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Using the basic principle of construction between a hydrogen bond acceptor (HBA) and a hydrogen bond donor (HBD), four bio-based deep eutectic solvents (DESs) were prepared in a 1:2 molar ratio of HBA:HBD. 2,3-Dihydroxypropyl-1-triethylammonium chloride ([C9H22N+O2]Cl−) was synthesized from raw glycerol and used as an HBA. Lactic acid, urea, pure glycerol, and ethylene glycol were selected as HBD. Attempts to prepare DESs, using citric acid and benzoic acid as HBDs, were unsuccessful. All these DESs were characterized using FTIR and NMR techniques. Besides, physicochemical parameters such as pH, viscosity, density, and melting point were determined. The behavior of these DES to fractionate olive pomace was studied. Lignin recovery yields spanned between 27% and 39% (w/w) of the available lignin in olive pomace. The best DES, in terms of lignin yield ([C9H22N+O2]Cl− -lactic acid), was selected to perform a scale-up lignin extraction using 40 g of olive pomace. Lignin recovery on the multigram scale was similar to the mg scale (38% w/w). Similarly, for the holocellulose-rich fractions, recovery yields were 34% and 45% for mg and multi-gram scale, respectively. Finally, this DES was used to fractionate four fruit pruning samples. These results show that our novel DESs are alternative approaches to the ionic liquid:triethylammonium hydrogen sulfate and the widely used DES: choline chloride:lactic acid (1:10 molar ratio) for biomass processing.

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“…(for the full 1 H NMR spectra of the samples studied see Supplementary Material). These results are in full agreement with the study performed on Kraft lignin by Diop et al [31].…”

Section: A) Ir Bands Assignments For Lignin B) Ir Bands Assignments Fsupporting

confidence: 93%

Effect of Four Novel Bio-Based DES (Deep Eutectic Solvents) on Hardwood Fractionation

et al. 2020

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“…Lignin is a natural organic polymer that is characterized by high chemical stability and structural complexity. Owing to its aromatic nature and high energy content (lignin represents about 40% of lignocellulosic biomass by energy content), it has been targeted for years as a renewable source of aromatic platform chemicals and biofuels. − However, practical usage and application of lignin requires a cost-effective method for depolymerization of the polymer into small molecules, a goal that has been shared for decades by numerous research groups. ,− Due to the assortment of linkages within the combinatorial polymer, depolymerization as well as separation of the newly cleaved units presents a significant challenge.…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical Treatment Facilitates Two-Step Oxidative Depolymerization of Kraft Lignin

Yao

Mobley

Ralph

et al. 2018

ACS Sustainable Chem. Eng.

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Mechanochemical treatment of Indulin AT kraft lignin by ball-milling with KOH and toluene produces significant carbonyl functionality, among other changes. The chemical reactivity of the lignin is increased, resulting in greater lignin degradation from porphyrin oxidation followed by Baeyer−Villiger oxidation. The mechanochemical treatment produces a level of lignin oxidation that is similar to that produced by porphyrin-catalyzed oxidation. Combining mechanochemical treatment with porphyrin oxidation has a synergistic positive effect on the depolymerization of lignin, as demonstrated by a significantly higher yield of monomers. The methyl ester of vanillic acid was obtained as the main monomeric product (after methylation), along with of methyl 5-carbomethoxyvanillate, in a 10% yield, which is among the highest reported from kraft lignin.

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“…However, such fundamental issues in IL processes for lignin valorization received little attention. 21,22 Therefore, the purpose of this study is to uncover whether chemical reactions would happen during lignin dissolution in alkaline cholinium ILs (Figure S1) under the specific conditions, and what chemical transformations would occur. Like organosolv and milled wood lignins, kraft lignin is also one of the promising starting materials for the valorization of lignin into value-added products.…”

Section: ■ Introductionmentioning

confidence: 99%

Changes in the Structure and the Thermal Properties of Kraft Lignin during Its Dissolution in Cholinium Ionic Liquids

et al. 2015

ACS Sustainable Chem. Eng.

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Lignin valorization using ionic liquids (ILs) has attracted growing interest recently. Cholinium ILs, a novel kind of bio-ILs, are good lignin solvents. In this work, the changes in the structure and the thermal properties of kraft lignin during its dissolution in this type of bio-ILs were examined in detail by nuclear magnetic resonance spectroscopy, gel permeation chromatography, elemental analysis, thermogravimetric analysis, and differential scanning calorimetry. It was found that the β-O-4′ linkage was broken during kraft lignin dissolution, while the β-β′ and β-5′ linkages were formed. In addition, the dehydration and demethoxylation reactions occurred. Besides, the dissolution process resulted in a higher maximal decomposition temperature (T m ) and a higher glass transition temperature (T g ) of kraft lignin as well as the low residual char and the reduced molecular weights. Hence, these chemical transformations should be taken into account during lignin dissolution in ILs when the mechanism of lignin valorization using IL processes is proposed in the presence of catalysts.

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Kraft Lignin Depolymerization in an Ionic Liquid without a Catalyst

Cited by 34 publications

References 0 publications

Effect of Four Novel Bio-Based DES (Deep Eutectic Solvents) on Hardwood Fractionation

Effect of Four Novel Bio-Based DES (Deep Eutectic Solvents) on Hardwood Fractionation

Mechanochemical Treatment Facilitates Two-Step Oxidative Depolymerization of Kraft Lignin

Changes in the Structure and the Thermal Properties of Kraft Lignin during Its Dissolution in Cholinium Ionic Liquids

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