Adsorption and separation of black liquor-derived phenol derivatives using anion exchange resins

Schmitt, Dominik; Beiser, Nicole; Regenbrecht, Carolin; Zirbes, Michael; Waldvogel, Siegfried R.

doi:10.1016/j.seppur.2017.03.004

Cited by 34 publications

(34 citation statements)

References 26 publications

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“…1 and traces of acetovanillone ( 2 ) are the only low molecular products, which were observed as starting material in determinable amounts (Figure b). This is in particular surprising due to the fact that lignin already contains traces of the phenol derivatives vanillin ( 1 ), acetovanillone ( 2 ), guaiacol ( 3 ) and 4,4’‐dihydroxy‐3,3’‐dimethoxy stilbene ( 4 ) . These compounds are observed if a lignin sample is dissolved in alkaline solution and afterwards acidified and the aqueous phase is subsequently subjected to liquid‐liquid extraction (Figure a).…”

Section: Resultsmentioning

confidence: 99%

“…This activation was observed even more pronounced by electrochemical treatment with pretreated black liquor (lignin and low molecular weight phenols containing waste stream from Kraft process). The black liquor has to be free of low molecular weight phenols which can be achieved by an adsorption protocol ,. Ni foam electrodes which enabled yields up to 1.0 wt% of 1 by treating lignin containing solutions were applied for the electrochemical degradation of lignin in black liquor.…”

Section: Resultsmentioning

confidence: 99%

“…Different catalytic systems, aiming various degradation products were developed but none of these reached a profitable economic impact so far . Electrochemical degradation of lignin was performed successfully using Ni and Co based materials in alkaline electrolytes . An electrocatalytic active surface layer turned out to be necessary for the degradation process.…”

Section: Introductionmentioning

confidence: 99%

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Anodic Degradation of Lignin at Active Transition Metal‐based Alloys and Performance‐enhanced Anodes

et al. 2018

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Electrochemical oxidative degradation is one of the most promising methods for generation of phenolic fine chemicals from the renewable feedstock lignin. High selectivity, no reagent waste, as well as cost efficiency are major advantages of this particular process. Application of Ni‐ and Co‐based anode materials led to the best results in respect to product yield and selectivity. Interestingly, repeated use of Ni foam electrodes for electrochemical oxidative degradation resulted in significantly increased yields of vanillin, indicating a modification of the electrode surface. In particular, activation of the electrodes by electrochemical treatment of black liquor enabled an activation which further increased the electrocatalytic activity as well as the yield of the aroma chemical vanillin up to more than 100 % compared to non‐activated Ni foam electrodes. Additionally, this activated electrode surface was analyzed via flowing atmospheric pressure afterglow surface desorption mass spectrometry (FAPA‐MS). The measurement revealed diaminotoluene as a major compound in this adsorption layer, which indicates that this compound is partly responsible for the activation process. Most likely, electrochemical induced deposition of such an organic surface layer enhances the lipophilicity of the electrode surface and increases the accessibility of relevant structural features of lignin particles to the anodic surface, resulting in a higher yield of the desired degradation product vanillin.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Anodic Degradation of Lignin at Active Transition Metal‐based Alloys and Performance‐enhanced Anodes

et al. 2018

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“…investigated the electrocatalytic degradation of aspen lignin on Pb/PbO 2 electrodes, and identified 4‐methylanisole as the main oxidation product. Waldvogel et al . reported the researches abut obtaining vanillin with a high selectivity by a combined approach of electrochemistry and product isolation by adsorption.…”

Section: Introductionmentioning

confidence: 99%

Fine Chemicals Prepared by Bamboo Lignin Degradation through Electrocatalytic Redox between Cu Cathode and Pb/PbO₂ Anode in Alkali Solution

Liu

et al. 2017

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Electrochemical degradation of bamboo lignin through electrocatalytic redox between Cu cathode and Pb/PbO 2 anode in sodium hydroxide solution was investigated in this work. Electrocatalytic performance of the electrode system was analyzed by cyclic voltammetry and cathodic polarization to validate that Cu and Pb/PbO 2 electrodes had a great ability of electrochemical oxidation and electrocatalytic hydrogenation (ECH) in lignin alkali solution. Through the electrocatalytic redox in the process, 24 kinds of products were detected by gas chromatography-mass spectrometry (GC-MS) and three of them (vanillin, syringaldehyde and p-coumaric acid) were detected with high yields by gas chromatograph (GC) with internal standard method. Effects of operating parameters, i. e., lignin concentration, current density and temperature, were also investigated to find the optimum degradation conditions at which the maximum yields of vanillin, syringaldehyde and pcoumaric acid could be obtained.

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“…coniferyl alcohol, guaiacol, vinylguaiacol, vanillin and acetovanillin. 11 Dimers include stilbene type structures 12 and enol ethers. 13 Advances have been made in making available the polymeric fractions through technically feasible recovery to obtain a brown powder.…”

Section: Introductionmentioning

confidence: 99%

A one-pot biomimetic synthesis of selectively functionalized lignins from monomers: a green functionalization platform

2018

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Lignin is the most abundant renewable source of phenolic compounds with great application potential in renewable materials, biofuels and platform chemicals. The current technology for producing celluloserich fibers co-produces heterogeneous lignin, which includes an untapped source of monomeric phenolics. One such monomer also happens to be the main monomer in soft wood lignin biosynthesis, namely coniferyl alcohol. Herein, we investigate the potential of coniferyl alcohol as a platform monomer for the biomimetic production of tailored functionalized oligolignols with desirable properties for material synthesis. Accordingly, a bifunctional molecule with at least one carboxyl-ended functionality is included with coniferyl alcohol in biomimetic lignin synthesis to, in one pot, produce a functionalized lignin. The functionalization mechanism is a nucleophilic addition reaction to the quinone methide intermediate of lignin polymerization. The solvent system applied was pure water or 50% aqueous acetone. Several bifunctional molecules differing in the second functionality were successfully inserted in the lignin demonstrating the platform component of this work. Detailed characterization was performed by a combination of NMR techniques which include 1 H NMR, COSY-90, 31 P NMR, 13 C NMR, 13 C APT, HSQC, HMBC and HSQC TOCSY. Excellent selectivity towards benzylic carbon and a high functionalization degree were noted. The structure of lignin was tailored through the solvent system choice, with 50% aqueous acetone producing a skeletal structure favorable for a high degree of functionalization. Finally, material concepts are demonstrated using classical thiol-ene-and Diels-Alder-chemistries to show the potential for the thermoset and thermoplastic concepts, respectively. The functionalization concept presents unprecedented opportunities for the green production of lignin-based recyclable biomaterials.

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Adsorption and separation of black liquor-derived phenol derivatives using anion exchange resins

Cited by 34 publications

References 26 publications

Anodic Degradation of Lignin at Active Transition Metal‐based Alloys and Performance‐enhanced Anodes

Anodic Degradation of Lignin at Active Transition Metal‐based Alloys and Performance‐enhanced Anodes

Fine Chemicals Prepared by Bamboo Lignin Degradation through Electrocatalytic Redox between Cu Cathode and Pb/PbO₂ Anode in Alkali Solution

A one-pot biomimetic synthesis of selectively functionalized lignins from monomers: a green functionalization platform

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Adsorption and separation of black liquor-derived phenol derivatives using anion exchange resins

Cited by 34 publications

References 26 publications

Anodic Degradation of Lignin at Active Transition Metal‐based Alloys and Performance‐enhanced Anodes

Anodic Degradation of Lignin at Active Transition Metal‐based Alloys and Performance‐enhanced Anodes

Fine Chemicals Prepared by Bamboo Lignin Degradation through Electrocatalytic Redox between Cu Cathode and Pb/PbO2 Anode in Alkali Solution

A one-pot biomimetic synthesis of selectively functionalized lignins from monomers: a green functionalization platform

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Fine Chemicals Prepared by Bamboo Lignin Degradation through Electrocatalytic Redox between Cu Cathode and Pb/PbO₂ Anode in Alkali Solution