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From Lignin to Valuable Aromatic Chemicals: Lignin Depolymerization and Monomer Separation via Centrifugal Partition Chromatography.

ABSTRACT: Lignin has long been recognized as a potential feedstock for aromatic molecules; however, most lignin depolymerization methods create a complex mixture of products. The present study describes an alkaline aerobic oxidation method that converts lignin extracted from poplar into a collection of oxygenated aromatics, including valuable commercial compounds such as vanillin and p-hydroxybenzoic acid. Centrifugal partition chromatography (CPC) is shown to be an effective method to isolate the individual compounds from the complex product mixture. The liquid-liquid extraction method proceeds in two stages. The crude depolymerization mixture is first subjected to ascending-mode extraction with the Arizona solvent system L (pentane/ethyl acetate/methanol/water 2:3:2:3), enabling isolation of vanillin, syringic acid, and oligomers. The remaining components, syringaldehyde, vanillic acid, and p-hydroxybenzoic acid (pHBA), were resolved by using ascending-mode extraction with solvent mixture comprising dichloromethane/methanol/water (10:6:4) separation. These results showcase CPC as an effective technology that could provide scalable access to valuable chemicals from lignin and other biomass-derived feedstocks.

SUBMITTER: Alherech M

PROVIDER: S-EPMC8614103 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:Starting with an isoflavone-rich red clover extract (RCE), this study expands on the DESIGNER approach to Deplete and Enrich Select Ingredients to Generate Normalized Extract Resources using countercurrent separation (CCS) methodology. A hydrostatic CCS (also known as centrifugal partition chromatography, CPC) technique was used to enrich and deplete selected bioactive isoflavones of RCE extracts. In order to efficiently prepare large enough DESIGNER extracts from RCE for biological testing including in vivo assays, it was necessary to choose a balance between resolution and a loading capacity of at least 1?g per separation for the selected solvent system (SS). Adding 3?mL of DMSO to the sample containing equal amounts of upper and lower phases of hexanes-ethyl acetate-methanol-water (HEMWat 5.5/4.5/5/5, v/v) allowed 1?g of RCE to be dissolved in the sample without disrupting the chromatographic resolution of the target isoflavones. CPC experiments using other solubility modifiers, acetone and acetonitrile indicated that these modifiers increase solubility significantly, even better than DMSO, but the separation of target compounds was sufficiently disturbed to be unacceptable for producing the desired DESIGNER extracts. The preparation of DESIGNER extracts was achieved with two sequential CPC separations. The first produced a biochanin A enriched fraction (93.60% w/w) with only small amounts of other isoflavones: 2.30% w/w prunetin, 1.17% w/w formononetin, and 0.12% w/w irilone. Gravimetric investigations of this step demonstrated the high efficiency of CCS technology for full and unbiased sample recovery, confirmed experimentally to be 99.80%. A formononetin enriched fraction from this first separation was re-chromatographed on a more polar HEMWat (4/6/4/6, v/v) SS to produce a formononetin enriched DESIGNER fraction of 94.70% w/w purity. The presence of the minor (iso)flavonoids: 3.16% w/w pseudobaptigenin, 0.39% w/w kaempferol, and 0.31% w/w genistein was also monitored in these fractions. Chromatographic fractions, combined fractions, and DESIGNER extracts were analyzed with quantitative 1H NMR (qHNMR) spectroscopy which provided purity information, quantitation, and structural identification of the components.

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From Lignin to Valuable Aromatic Chemicals: Lignin Depolymerization and Monomer Separation via Centrifugal Partition Chromatography.

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