Ultrasonic-assisted synthesis of aminated lignin by a Mannich reaction and its decolorizing properties for anionic azo-dyes

Wang, Xiaohong; Zhang, Yike; Chen, Hao; Dai, Xiaohui; Zhou, Zilong; Si, Naichao

doi:10.1039/c4ra03133d

Cited by 79 publications

(57 citation statements)

References 34 publications

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“…The copolymerization mechanism of lignin is shown in Scheme . Softwood kraft lignin consists of mostly coniferyl alcohol groups, and this was chosen as the site of propagation for lignin, as this is the dominant repeating unit present in softwood lignin . The thermal decomposition of sodium persulfate into two sulfate radical anions (SO 4 ⋅− ) consists of the initiation step in the polymerization (Scheme i) .…”

Section: Resultsmentioning

confidence: 80%

“…Softwood kraft lignin consists of mostly coniferyl alcohol groups, and this was chosen as the site of propagation forlignin, as this is the dominant repeating unit presenti ns oftwood lignin. [30] The thermal decomposition of sodium persulfate into two sulfate radical anions (SO 4 ·À )c onsists of the initiations tep in the polymerization (Scheme 1i). [31] The free radicalg enerated from the thermal decomposition of sodium persulfate can then be transferred to either lignin, DADMAC, or AM present in the reaction mixture.…”

Section: Reaction Mechanismmentioning

confidence: 99%

“…[27] Kraft lignin can also be used in the production of flocculants;however,kraft lignin is only soluble in aqueous solutions at ap Hh igher than 11.K raft lignin can be converted to water-soluble flocculants through chemical modification (oxidation, sulfomethylation, carboxymethylation and co-polymerization). [7,19,28,29] The cationic modification of kraft lignin by epoxide ring-opening using GTMAC [28] and the Mannich [30] reactionh as been studied extensively in both organic and aqueous media (alkaline pH). The graft copolymerization of kraft lignin with AM, methacryloxyethyl trimethylammonium chloride (DMC)a nd DADMAC has also been assessed in organic solvents for their potentialu se as af locculant in wastewater treatment.…”

Section: Introductionmentioning

confidence: 99%

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Lignin‐g‐poly(acrylamide)‐g‐poly(diallyldimethyl‐ ammonium chloride): Synthesis, Characterization and Applications

2018

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The search for a renewable substitute to petroleum‐based products has fueled increasing research on lignin, an under‐utilized product from pulping processes. In this work, lignin was copolymerized with acrylamide (AM) and diallyldimethylammonium chloride (DADMAC) under acidic conditions with Na2S2O8 as an initiator, generating a cationic water‐soluble lignin‐g‐P(AM)‐g‐P(DADMAC) copolymer. The optimal reaction conditions, using a 5×4 factorial design experiment, were determined to be an AM/DADMAC/lignin molar ratio of 5.5:2.4:1, 90 °C, 0.26 mol L−1 of lignin, and pH 2. Under the optimal reaction conditions, the resulting lignin‐g‐P(AM)‐g‐P(DADMAC) copolymer was 83 % soluble in an aqueous solution (at 10 g L−1) and at neutral pH. The copolymer had a charge density of 1.27 meq g−1, molecular weight of (1.33±0.08) ×106, an AM grafting ratio of 112 wt %, and a DADMAC grafting ratio of 20 wt %. In addition, the activation energy for producing this copolymer as well as the thermal and rheological properties of the copolymer were determined. The flocculation performance of lignin‐g‐P(AM)‐g‐P(DADMAC) copolymer was evaluated in a kaolin suspension, which showed that the lignin copolymer had a comparable flocculation efficiency with the synthetic analogue of P(AM)‐g‐P(DADMAC) at pH 6.

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Section: Resultsmentioning

confidence: 80%

Section: Reaction Mechanismmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Lignin‐g‐poly(acrylamide)‐g‐poly(diallyldimethyl‐ ammonium chloride): Synthesis, Characterization and Applications

2018

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“…If not recovered or treated, the black liquor would greatly contaminate the environment. Therefore, raising the utilization efficiency of lignosulphonate, the conversion and reuse of the low-cost lignosulphonate waste are highly demanded [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Hydrothermal synthesis of flower cluster-shaped ZnO microstructures with sodium lignosulfonate as structure-directing agent

Chen

Zhang

Wang

et al. 2015

J Mater Sci: Mater Electron

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Flower cluster-shaped ZnO microstructures have been successfully synthesized by a facile hydrothermal approach without further heat treatment using Zn(NO 3 ) 2 . 6H 2 O and NaOH as raw materials and sodium lignosulfonate (SL) as a structure-directing agent. The morphology, structure, and property of the products were characterized by X-ray powder diffraction, fourier transform infrared spectroscopy, scanning electron microscopy, Brunauer-Emmett-Teller nitrogen adsorption-desorption isotherms and photoluminescence spectrum. The photocatalytic activity of the as-prepared samples were evaluated by photocatalytic decolorization of methylene blue aqueous solution at ambient temperature. The results indicated that the prepared ZnO-SL sample exhibited flower clustered morphology, hexagonal wurtzite structure, higher surface areas and better UV and visible photocatalytic activity. Moreover, the ZnO-SL sample showed excellent stability after three photodegradation cycling runs.

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“…There are also studies on flocculants derived from technical lignins taking advantage of its aromatic hydrophobicity. Lignin derivatives having acrylamide‐graft chain, hexane‐diamine side‐chain, and sulfomethyl group were prepared and their flocculating properties were studied. These researches mainly focus on the correlation between the charge density of the flocculants and the flocculation behavior.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of lignin‐based cationic dye‐flocculant

Kajihara

Aoki

Matsushita

et al. 2018

J of Applied Polymer Sci

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Kraft lignin derivatives having cationic poly 2-(trimethylamino)ethyl methacrylate side chains were synthesized and their property as dye-flocculant was investigated. Lignin-based flocculants having three types of side chain densities and three types of side chain lengths were synthesized by esterification of the lignin hydroxyl groups with bromoisobutyryl groups, atom transfer radical polymerization using 2-(dimethylamino)ethyl methacrylate, and quaternization of the amino groups. Dye removal test was performed using three organic dyes and the obtained lignin-based flocculants. The results indicated that the density and the length of the side chains obviously affected the flocculation behavior. When the flocculants containing the same nitrogen amount were compared, the flocculation performance was improved with the increase of the side chain length within the samples having low and middle side chain densities. In the case of the samples having high side chain density, the most efficient sample was not the sample having the longest side chain. Most of the lignin-based flocculants removed dyes more efficiently than the poly 2-(trimethylamino)ethyl methacrylate homopolymer. From these results, it was suggested that lignin has a potential character as the core molecule to design the high-efficient dye-flocculant.

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Ultrasonic-assisted synthesis of aminated lignin by a Mannich reaction and its decolorizing properties for anionic azo-dyes

Cited by 79 publications

References 34 publications

Lignin‐g‐poly(acrylamide)‐g‐poly(diallyldimethyl‐ ammonium chloride): Synthesis, Characterization and Applications

Lignin‐g‐poly(acrylamide)‐g‐poly(diallyldimethyl‐ ammonium chloride): Synthesis, Characterization and Applications

Hydrothermal synthesis of flower cluster-shaped ZnO microstructures with sodium lignosulfonate as structure-directing agent

Synthesis and characterization of lignin‐based cationic dye‐flocculant

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