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Enhancing the Antioxidant Activity of Technical Lignins by Combining Solvent Fractionation and Ionic-Liquid Treatment.

ABSTRACT: A grass soda technical lignin (PB1000) underwent a process combining solvent fractionation and treatment with an ionic liquid (IL), and a comprehensive investigation of the structural modifications was performed by using high-performance size-exclusion chromatography, ³¹ P?NMR spectroscopy, thioacidolysis, and GC-MS. Three fractions with distinct reactivity were recovered from successive ethyl acetate (EA), butanone, and methanol extractions. In parallel, a fraction deprived of EA extractives was obtained. The samples were treated with methyl imidazolium bromide ([HMIM]Br) by using either conventional heating or microwave irradiation. The treatment allowed us to solubilize 28?% of the EA-insoluble fraction and yielded additional free phenols in all the fractions, as a consequence of depolymerization and demethylation. The gain of the combined process in terms of antioxidant properties was demonstrated through 2,2-diphenyl-1-picrylhydrazyl (DPPH^. ) radical-scavenging tests. Integrating further IL safety-related data and environmental considerations, this study paves the way for the sustainable production of phenolic oligomers competing with commercial antioxidants.

SUBMITTER: Majira A

PROVIDER: S-EPMC6899661 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Enhancing the Antioxidant Activity of Technical Lignins by Combining Solvent Fractionation and Ionic-Liquid Treatment.

Majira Amel A Godon Blandine B Foulon Laurence L van der Putten Jacinta C JC Cézard Laurent L Thierry Marina M Pion Florian F Bado-Nilles Anne A Pandard Pascal P Jayabalan Thangavelu T Aguié-Béghin Véronique V Ducrot Paul-Henri PH Lapierre Catherine C Marlair Guy G Gosselink Richard J A RJA Baumberger Stephanie S Cottyn Betty B

ChemSusChem 20190924 21

A grass soda technical lignin (PB1000) underwent a process combining solvent fractionation and treatment with an ionic liquid (IL), and a comprehensive investigation of the structural modifications was performed by using high-performance size-exclusion chromatography, <sup>31</sup> P NMR spectroscopy, thioacidolysis, and GC-MS. Three fractions with distinct reactivity were recovered from successive ethyl acetate (EA), butanone, and methanol extractions. In parallel, a fraction deprived of EA ext ...[more]

PMID: 31436856

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Project description:Lignin can be considered an essential under-exploited polymer from lignocellulosic biomass representing a key for a profitable biorefinery. One method of lignin valorization could be the improvement of physico-chemical properties by esterification to enhance miscibility in apolar polyolefin matrices, thereby helping the production of bio-based composites. The present work describes for the first time a succeeded chemical esterification of industrial lignins with maleic anhydride in an acidic ionic liquid: 1-butyl-3-methyl imidazolium hydrogen sulfate without additional catalyst. This efficient strategy was applied to four industrial lignins: two softwood Kraft lignins (Indulin AT, Wayagamack), one hardwood Kraft lignin (Windsor), and one softwood organosolv lignin (Lignol), distinct in origin, extraction process and thus chemical structure. The chemical, structural, and thermal properties of modified lignins were characterized by 31P nuclear magnetic resonance, infrared spectroscopy and thermal analyses, then compared to those of unmodified lignins. After 4 h of reaction, between 30 to 52% of the constitutive hydroxyls were esterified depending on the type of lignin sample. The regioselectivity of the reaction was demonstrated to be preferentially orientated toward aliphatic hydroxyls for three out of four lignins (66.6, 65.5, and 83.6% for Indulin AT, Windsor and Lignol, respectively, vs. 51.7% for Wayagamack). The origin and the extraction process of the polymer would thus influence the efficiency and the regioselectivity of this reaction. Finally, we demonstrated that the covalent grafting of maleyl chain on lignins did not significantly affect thermal stability and increased significantly the solubility in polar and protic solvent probably due to additional exposed carboxylic groups resulted from mono-acylation independently of H/G/S ratio. Blending with polyolefins could then be considered in regard of compatibility with the obtained physico-chemical properties.

Dataset Information

Enhancing the Antioxidant Activity of Technical Lignins by Combining Solvent Fractionation and Ionic-Liquid Treatment.

Publications

Enhancing the Antioxidant Activity of Technical Lignins by Combining Solvent Fractionation and Ionic-Liquid Treatment.

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