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Biocatalytic selective acylation of technical lignins: a new route for the design of new biobased additives for industrial formulations.

ABSTRACT: In this article, we describe a proof of concept of the potential use of a biocatalytic process for the functionalization of technical soda lignins from wheat straw through the selective acylation of primary hydroxy groups of lignin oligomers by acetate or hexanoate, thus preserving their free, unreacted phenols. The selectivity and efficiency of the method, although they depend on the structural complexity of the starting material, have been proven on model compounds. Applied to technical lignins, the acylation yield is only moderate, due to structural and chemical features induced by the industrial mode of preparation of the lignins rather than to the lack of efficiency of the method. However, most of the physicochemical properties of the lignins, including their antioxidant potential, are preserved, advocating the potential use of these modified lignins for industrial applications.

SUBMITTER: Sarieddine A

PROVIDER: S-EPMC10400768 | biostudies-literature | 2023

REPOSITORIES: biostudies-literature

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Biocatalytic selective acylation of technical lignins: a new route for the design of new biobased additives for industrial formulations.

Sarieddine Aya A Hadjiefstathiou Caroline C Majira Amel A Pion Florian F Ducrot Paul-Henri PH

Frontiers in chemistry 20230721

In this article, we describe a proof of concept of the potential use of a biocatalytic process for the functionalization of technical soda lignins from wheat straw through the selective acylation of primary hydroxy groups of lignin oligomers by acetate or hexanoate, thus preserving their free, unreacted phenols. The selectivity and efficiency of the method, although they depend on the structural complexity of the starting material, have been proven on model compounds. Applied to technical lignin ...[more]

PMID: 37547909

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Project description:A first systematic approach on the base catalyzed depolymerization (BCD) of five technical lignins derived from various botanical origins (herbaceous, hardwood and softwood) and covering the main three industrial pulping methods (soda, kraft and organosolv) is reported. This study provides a first of its kind in-depth quantification and structural characterization of two main BCD fractions namely lignin oil and lignin residue, describing the influence of the BCD process conditions. Depolymerization is evaluated in terms of lignin conversion, lignin oil yield, phenolic monomer selectivity and the production of lignin residue and char. Lignin oils were extensively characterized by size exclusion chromatography (SEC), GC-MS, GC-FID, 13C-NMR, HSQC NMR and elemental analysis. GC × GC-FID was used to identify and quantify distinct groups of monomeric compounds (methoxy phenols, phenols, dihydroxy-benzenes) in the lignin oil. The lignin oil yields (w/w) ranged from 20-31% with total monomer contents ranging from 48 to 57% w/w. SEC analysis indicated the presence of dimers/oligomers in the lignin oil, which through HSQC NMR analysis were confirmed to contain new, non-native interunit linkages. 13C NMR analyses of the lignin oils suggest the presence of diaryl type linkages (i.e. aryl-aryl, aryl C-O) evidencing deconstruction and recombination of lignin fragments during BCD. Irrespective of the lignin source, a residue, often regarded as 'unreacted' residual lignin was the main product of BCD (43 to 70% w/w). Our study highlights that this residue has different structural properties and should not be considered as unreacted lignin, but rather as an alkali soluble condensed aromatic material. HSQC, DEPT-135, 13C, and 31P NMR and SEC analyses confirm that the BCD residues are indeed more condensed, with increased phenolic hydroxyl content and lower molecular weights compared to all feed lignins. Subsequent BCD of solid residual fractions produced only low oil yields (6-9% w/w) with lower phenolic monomer yields (4% w/w) compared to original lignin, confirming the significantly more recalcitrant structure. Our study improves the overall understanding of the BCD process, highlights important feedstock-dependent outcomes and ultimately contributes to the complete valorization of BCD-derived lignin streams.

Dataset Information

Biocatalytic selective acylation of technical lignins: a new route for the design of new biobased additives for industrial formulations.

Publications

Biocatalytic selective acylation of technical lignins: a new route for the design of new biobased additives for industrial formulations.

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