Synthesis of Lignin-based Phenol Terminated Hyperbranched Polymer

Longe, Lionel; Garnier, Gil; Saito, Kei

doi:10.3390/molecules24203717

Cited by 9 publications

(12 citation statements)

References 30 publications

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“…The reaction of pure vanillin to vanillic acid in highly alkaline media is already known. [ 71 ] The reaction occurs within 45 min at 150 °C in potassium hydroxide solution (8.25 g L −1 ). Since 40 wt% NaOH has shown to be ideally suited for efficient ferrate electro‐generation, the same concentration was used for lignin degradation under the assumption that formed vanillin is directly overoxidized to the corresponding acid in a single step.…”

Section: Resultsmentioning

confidence: 99%

Degradation of Lignosulfonate to Vanillic Acid Using Ferrate

Klein

Kupec

Stöckl

et al. 2022

Advanced Sustainable Systems

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high technical interest as renewable and biobased feedstock [7] due to their aromatic backbone and high availability. [8][9][10][11] Consequently, the targeted degradation of the respective lignin fractions to value-added products is highly desired. [12,13] The difficulty of this process lies in the different functionalization and the structure of the polyphenolic backbone, which depends on many factors such as pulping process, harvesting time, and type of tree. [10,14] Therefore, the industry uses only small fractions for further production, while the majority is incinerated to recover energy costs. [4,9] Lignin, as a renewable feedstock, offers a promising alternative to petroleum refining and shows tremendous potential for bio-based products such as surfactants and fine chemicals. [5,13,15] Nevertheless, selective degradation is challenging, and several studies focused on this complex topic to degrade lignin into value-added products such as aromatic intermediates. [8,[16][17][18] Lignin degradation shows a broad and diverse spectrum of products, such as aldehydes, [19][20][21]22] alcohols, [21] arenes, [18,23,24] quinones, [25] and carboxylic acids, [16,26,27] obtained in previous research. Different metal-based catalysts were studied to improve degradation and increase selectivity including noble metals like ruthenium, palladium, and platinum. [28] The disadvantages of these processes are the very high costs and limited availability of the metals, which might also cause uncontrolled over-hydrogenation, decreasing the yield of the phenolic products. Another approach is using ionic liquids as solvents in combination with catalysts or oxidizers. [29] However, the high costs for ionic liquids restrict their application for industrial operations. Additionally, the separation process is complex due to interactions with aromatic moieties of residual lignin.Promising electrochemical pathways are reported to yield aldehydes, [3,21,30] carboxylic acids, [27,31] and other phenolic products in good yields. [19,21,27,30] These methods are cost-effective and environmentally friendly. [32] Also, a well-known alternative is the use of oxidizers for lignin degradation. [3,20,23] However, only a few oxidizers, such as periodate, [3] nitrobenzene, [33,34] or hydrogen peroxide, [35] have high availability, and are safe in handling. Moreover, lignin conversion is not limited to the electrode surface since the respective oxidizers are dissolved. The monomer yields out of lignin using oxidizers vary significantly due to different wood types and experimental conditions. In a previous report, we showed that platform oxidizers, such as periodate, are highly beneficial for lignin degradation. This method significantly improves the vanillin yield (8.9 wt%) or selectively produces 5-iodovanillin using different workup conditions. [3] A new method is presented using electrochemically generated ferrate to degrade the technically relevant bio-based side-stream products, lignin and lignosulfonate. An exclusive degradation to vanillic ac...

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Section: Resultsmentioning

confidence: 99%

Degradation of Lignosulfonate to Vanillic Acid Using Ferrate

Klein

Kupec

Stöckl

et al. 2022

Advanced Sustainable Systems

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“…For example, the isomerization reaction of catechins [ 25 ] and the reaction of malonic acid and PP 1 to PP 3 [ 30 ]. Thirdly, the hydroxyl and aldehyde groups in PPs may be oxidized to carboxyl groups at high temperatures, thereby promoting the occurrence of oxidation reactions [ 15 , 31 ]. For example, the aldehyde group in PP 1 is oxidized to produce PP 2 [ 32 ], and induce the conversion between PP 8 and PP 7.…”

Section: Discussionmentioning

confidence: 99%

“…Other compounds, such as methylglyoxal [ 13 ] and glyoxylic acid [ 14 ], may provide functional groups in the derivation of PPs to promote the succession of PPs. In addition, hydroxylation, methylation, and methoxylation also have an important impact on the succession of PPs [ 15 , 16 ]. Food processing often causes changes in a variety of environmental factors that affect the accumulation of PPs, which makes the formation mechanism of PPs complicated and difficult to regulate.…”

Section: Introductionmentioning

confidence: 99%

Elucidation and Regulation of Polyphenols in the Smoking Process of Shanxi Aged Vinegar

Xie

Song

Bingqian

et al. 2021

Foods

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Polyphenols (PPs) are the main contributors to the health functions of Shanxi aged vinegar (SAV) and are mainly produced during the smoking process. This study aimed to explore the feasibility of regulating the accumulation of total water-soluble PPs (TWSP) by changing environmental factors based on the distribution of PPs. A total of eleven PPs, such as vanillin, vanillic acid, and (e)-ferulic acid, were detected during the smoking process. During the smoking process, the content of TWSP gradually increased and was accompanied by changes in environmental factors. Spearman correlation analysis and verification experiments showed that temperature, amino acids, and reducing sugars, as the main influencing factors, promoted the accumulation of TWSP. The in situ regulation strategy of changing environmental factors significantly increased the accumulation of TWSP by 12.24%.

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“…Highly branched polymers are prepared by several methods, which mainly include single-monomer methodology (SMM) 41,115−121 and double-monomer methodology (DMM). 122−124 The SMM is based on the polymerization of monomers with AB n structure or potential AB n monomer, such as AB n -type condensation methodology, 41 proton transfer polymerization (PTP), 120 selfcondensation vinyl polymerization (SCVP), 115−119 and selfcondensation ring-opening polymerization (SCROP). 121 The DMM method employs a pair of monomers to carry out the polymerization, primarily including "A 2 + B 3 " type monomer pair methodology 124 and couple-monomer methodology (CMM).…”

Section: Highly Branched Polymersmentioning

confidence: 99%

“…In the synthesis of branched polymers, conventional radical polymerization sometimes leads to gelation, while living radical polymerization has shown satisfactory performance in some cases. 33−37 In recent years, great efforts to synthesize welldefined branched polymers by living polymerization such as reversible addition−fragmentation chain transfer polymerization (RAFT), 33,38−40 atom transfer radical polymerization (ATRP), 35,41,42 ring-opening polymerization (ROP), 18,43,44 ring-opening metathesis polymerization (ROMP), 20,45−47 nitroxide-mediated polymerization (NMP), 48−51 iodine transfer polymerization (ITP), 52−54 living cationic polymerization (LCP), 55,56 and living anionic polymerization (LAP) 57 concentration using thiocarbonate as chain transfer agent to control the reversible chain transfer of macromolecular chains. This method is applicable to the polymerization of a wide range of monomers, and even some olefinic monomers containing special functional groups can also be polymerized.…”

Section: Introductionmentioning

confidence: 99%

Branched Polymers: Synthesis and Application

Shao,

Li,

Liu

et al. 2023

Macromolecules

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Branched polymers have aroused great interest due to their less chain entanglement, high concentration of chain terminals, good solubility, and low viscosity in melts and solutions. In this Perspective, we highlight various synthesis strategies for branched polymers with different structures and discuss their applications in the field of solid polymer electrolytes for lithium batteries, coatings and membranes, surfactants, hydrogels, and so on. Here, we expect to arouse more synthesis approaches such as enzyme-catalyzed living radical polymerization and photoinitiated living radical polymerization and also to copolymerize monomers with different properties or to modify branched polymers in order to obtain functionalized branched polymers that can be produced under mild conditions.

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Synthesis of Lignin-based Phenol Terminated Hyperbranched Polymer

Cited by 9 publications

References 30 publications

Degradation of Lignosulfonate to Vanillic Acid Using Ferrate

Degradation of Lignosulfonate to Vanillic Acid Using Ferrate

Elucidation and Regulation of Polyphenols in the Smoking Process of Shanxi Aged Vinegar

Branched Polymers: Synthesis and Application

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