Synthesis of maleilated polyflavonoids and lignin as functional bio-based building-blocks

GARCÍA, D.; DELGADO, N.; ARANDA, F.; TOLEDO, M.; CABRERA-BARJAS, G.; SINTJAGO, E.; ESCOBAR-AVELLO, D.; PACZKOWSKI, S.:
Industrial Crops & Products 123 (2018) 154-163.

DOI:10.1016/j.indcrop.2018.06.065

Abstract

Polyflavonoids and lignin from Pinus radiata (D. Don.) biomass were esterified with maleic anhydride by several synthesis pathways (22 °C, 24 h). Influence of the solvent (dimethylformamide (DMF), DMF/H2O, acetone, formamide)-, the catalyst-type (H2SO4, NaHCO3), and the NaHCO3-change (70 and 100 mmol) on the esterification yield, and the degree of substitution (DS) were estimated. The effect of the maleilation on structural features was assessed by spectroscopy (FT-IR, UV–vis, RMN), and molecular exclusion chromatography. FT-IR, and 1H-NMR provide valuable insight regarding the esterification extent. The results show that esterification of high molecular weight polyphenols exhibited reasonable yields (80–95 wt.%). A significant influence of the solvent-, and the catalyst was observed. Synthesis in formamide, as well as by the highest charge of the alkaline catalyst, exhibited the best performance toward the polyphenol´s modification. Maleilation efficiency was strongly influenced by the polyphenol-type. Non-water soluble polyflavonoid derivatives exhibited the highest DS/monomer unit regardless the synthesis conditions. Carboxylated polyphenols from radiata pine may be used as functional co-polymer for new kinds of material applications.

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