Fractionation of acids, ketones and aldehydes from alkaline lignin oxidation solution with SP700 resin

Gomes, E.D.; Mota, Maria Inês Ferreira da; Rodrigues, Alírio E.

doi:10.1016/j.seppur.2017.11.050

Cited by 25 publications

(14 citation statements)

References 26 publications

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“…Besides recycling, the lignin could also be further processed into various monomeric and polymeric products (e.g. Gomes et al, 2018;Lignimatch, 2010;Mota et al, 2016;Silva et al, 2009;Upton and Kasko, 2016).…”

Section: Introductionmentioning

confidence: 99%

Novel chromatographic process for the recovery and purification of hydroxy acids from alkaline spent pulping liquors

Heinonen

Sainio

2019

Chemical Engineering Science

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In this study, an efficient sequential chromatographic process for recovering hydroxy acids (HAs) from soda and kraft black liquors (BLs) has been developed. Lignin and pulping chemicals are also recovered and can be recycled back to the pulping process. A weak cation exchange resin in Na + form separates lignin from BL. Up to 95% lignin yield was obtained, with over 50% yield for HAs as Na salts. A cellulose-based resin is used to separate HAs from NaOH. Complete separation, and thus 100% yield for HAs and NaOH, was achieved. The HAs in soda BL are liberated by ion exchange. In case of kraft BL, the solution is acidified with H 2 SO 4 and subjected to ion exchange and ion exclusion chromatography to recover the remaining pulping chemicals. It was found that fouling, which limits the efficiency of membrane-based processing of BLs, is avoided with the appropriate choice of chromatographic separation materials.

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Section: Introductionmentioning

confidence: 99%

Novel chromatographic process for the recovery and purification of hydroxy acids from alkaline spent pulping liquors

Heinonen

Sainio

2019

Chemical Engineering Science

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“…After a membrane separation step, the permeate, containing the low molecular weight phenolates and excess NaOH, flows through a packed bed with a polymeric resin [ 58 , 108 ]. The separation of the different species will be achieved by adsorption, which can fractionate the permeate solution in families of chemicals, namely phenolic acids, aldehydes, and ketones [ 109 , 110 ]. In the end, the phenolic compounds of interest, aldehydes in this case, that are present in the enriched desorbed fraction will be recovered by crystallization [ 60 ].…”

Section: Integrated Processmentioning

confidence: 99%

Added-Value Chemicals from Lignin Oxidation

2021

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Lignin is the second most abundant component, next to cellulose, in lignocellulosic biomass. Large amounts of this polymer are produced annually in the pulp and paper industries as a coproduct from the cooking process—most of it burned as fuel for energy. Strategies regarding lignin valorization have attracted significant attention over the recent decades due to lignin’s aromatic structure. Oxidative depolymerization allows converting lignin into added-value compounds, as phenolic monomers and/or dicarboxylic acids, which could be an excellent alternative to aromatic petrochemicals. However, the major challenge is to enhance the reactivity and selectivity of the lignin structure towards depolymerization and prevent condensation reactions. This review includes a comprehensive overview of the main contributions of lignin valorization through oxidative depolymerization to produce added-value compounds (vanillin and syringaldehyde) that have been developed over the recent decades in the LSRE group. An evaluation of the valuable products obtained from oxidation in an alkaline medium with oxygen of lignins and liquors from different sources and delignification processes is also provided. A review of C4 dicarboxylic acids obtained from lignin oxidation is also included, emphasizing catalytic conversion by O2 or H2O2 oxidation.

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“…The distinct behavior of aromatic acids in contrast to aromatic aldehydes and ketones at high pH was also reported to be beneficial for adsorption and separation in chromatographic columns. 10 Bearing in mind the window of K values suitable for the CPC technique (K < 5), the separation of lignin monomers with the PEG-NaPA-based system assisted by ILs is expected to produce better chromatographic separation and resolution than with inorganic salts. Yet, the K values of all lignin monomers still exceeded the upper limit of the theoretical ideal range (0.4 ≤ K ≤ 2.5).…”

Section: ■ Introductionmentioning

confidence: 99%

“…Liquid–liquid separations, combined ionic liquid (IL) and supercritical carbon dioxide extraction (scCO 2 ), crystallization, adsorption in specific polymeric resins, and membrane separation are some of the key downstream technologies that have been proposed for lignin monomers (e.g., vanillin, syringaldehyde, and p -hydroxybenzaldehyde). − However, their low efficiency and selectivity, high cost, and difficult scale-up limit their widespread application in industry. Therefore, the development of more efficient, selective, yet scalable processes toward the separation and purification of lignin-derived monomers is required.…”

Section: Introductionmentioning

confidence: 99%

Selective Separation of Vanillic Acid from Other Lignin-Derived Monomers Using Centrifugal Partition Chromatography: The Effect of pH

Rocha

Lopes

Ventura

et al. 2022

ACS Sustainable Chem. Eng.

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In this work, centrifugal partition chromatography (CPC) assisted by a polyethylene glycol (PEG)/sodium polyacrylate (NaPA) aqueous biphasic system (ABS) was applied in the separation of five lignin-derived monomers (vanillin, vanillic acid, syringaldehyde, acetovanillone, and p-hydroxybenzaldehyde). The influence of the system pH (unbuffered, pH 5, and pH 12) and added electrolytes (inorganic salts or ionic liquids (ILs)) on the compound partition was initially evaluated. The obtained data revealed that ILs induced more adequate partition coefficients (K < 5) than inorganic salts (K > 5) to enable separation performance in CPC, while alkaline conditions (pH 12) demonstrated a positive impact on the partition of vanillic acid. CPC runs, with buffered ABS at pH 12, enabled a selective separation of vanillic acid from other lignin monomers. Under these conditions, a distinct interaction between the top (PEG-rich) and bottom (NaPA-rich) phases of the ABS with the double deprotonated form of vanillic acid is expected when compared to the remaining lignin monomers (single deprotonated). This is an impactful result that shows the pH to be a crucial factor in the separation of lignin monomer compounds by CPC, while only unbuffered systems have been previously studied in the literature. Finally, the recovery of vanillic acid up to 96% purity and further recycling of ABS phase-forming components were approached as a proof of concept through the combination of ultrafiltration and solid-phase extraction steps.

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Fractionation of acids, ketones and aldehydes from alkaline lignin oxidation solution with SP700 resin

Cited by 25 publications

References 26 publications

Novel chromatographic process for the recovery and purification of hydroxy acids from alkaline spent pulping liquors

Novel chromatographic process for the recovery and purification of hydroxy acids from alkaline spent pulping liquors

Added-Value Chemicals from Lignin Oxidation

Selective Separation of Vanillic Acid from Other Lignin-Derived Monomers Using Centrifugal Partition Chromatography: The Effect of pH

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