Tosylation and Characterization of Lignin in Water

Diop, Amadou; Awada, Houssein; Zerrouki, Rachida; Daneault, Claude; Montplaisir, Daniel

doi:10.1021/ie502543p

Cited by 16 publications

(15 citation statements)

References 24 publications

(28 reference statements)

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“…Tosyl moiety is an excellent leaving group in nucleophilic substitution reactions and can, for instance, be substituted by halogens, azide, or amines. Tosylation of cellulose and of lignin in water or in eco-friendly medium was reported in the literature [10][11][12]. To the best of our knowledge, the tosylation of PVA in aqueous media has not yet been reported.…”

Section: Introductionmentioning

confidence: 97%

Chemical Modification of Poly(Vinyl Alcohol) in Water

2015

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Partial chemical modification of poly(vinyl alcohol) (PVA) was performed through tosylation followed by azidation. Amine functional PVA was also prepared by grafting propargylamine using click chemistry reaction. Through this approach, a tosyl group (a good leaving group), azide group (a group used in click chemistry) and amine group (a group used for amidation) were attached to PVA polymer chains. The three chemical modifications were performed in water. FTIR and XPS analysis confirmed the chemical modification after each step. Thermogravimetric analysis (TGA) was used to study the thermal stability of the modified PVA.

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Section: Introductionmentioning

confidence: 97%

Chemical Modification of Poly(Vinyl Alcohol) in Water

2015

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“…Moreover, shifting of tertiary proton signal from 2.1 to 2.3 ppm indicates the formation of tosyl groups in hydroxyl backbone of lignin. Therefore, it is evident that tosylation reaction in lignin takes place in both aromatic as well as aliphatic hydroxyl functional groups 24 . The degree of tosylation of the lignin macroinitiators, amount of excess tosyl chloride was optimized with increasing feeding value in reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Tosylated lignin was prepared according to procedure Diop et al . in aqueous medium 38 . One gram of lignin was dissolved in 10 mL distilled water and stirred for 1 hour after addition of 0.0025 molar (250 mg) of triethyl amine at 0–5 °C.…”

Section: Methodsmentioning

confidence: 99%

Lignin-graft-Polyoxazoline Conjugated Triazole a Novel Anti-Infective Ointment to Control Persistent Inflammation

Mahata

Jana

et al. 2017

Sci Rep

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Lignin, one of the most abundant renewable feedstock, is used to develop a biocompatible hydrogel as anti-infective ointment. A hydrophilic polyoxazoline chain is grafted through ring opening polymerization, possess homogeneous spherical nanoparticles of 10–15 nm. The copolymer was covalently modified with triazole moiety to fortify the antimicrobial and antibiofilm activities. The hydrogel was capable of down regulating the expression level of IL-1β in LPS induced macrophage cells, and to cause significant reduction of iNOS production. It supported cellular anti-inflammatory activity which was confirmed with luciferase assay, western blot, and NF-κB analysis. This novel lignin-based hydrogel tested in-vivo has shown the abilities to prevent infection of burn wound, aid healing, and an anti-inflammatory dressing material. The hydrogel reported here provides a new material platform to introduce a cost-effective and efficient ointment option after undertaking further work to look at its use in the area of clinical practice.

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“…Recently, tosylated lignin was synthesized in an aqueous medium in the absence of any organic solvent; it is more reactive than unmodified lignin and shows potential for several applications. 20 Inspired by this work, here we develop a new practical method to modify lignin with di-tert-butyl dicarbonate (Boc2O) without using any organic solvents. The degree of the modification can be tuned by adjusting the loading of catalyst and the amount of Boc2O used.…”

Section: Scheme 1 Common Lignin Modification Strategies and Our New mentioning

confidence: 99%

Tunable Boc Modification of Lignin and Its Impact on Microbial Degradation Rate

Gu¹,

Wang²,

Li³

et al. 2018

Preprint

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A new type of modified lignin, lignin-p-Boc was obtained through reaction with di-<i>tert</i>-butyl dicarbonate in aqueous media. Boc modification occurred regardless of types of lignin, was tunable, and proceeded well in recovering lignin at high purity from sodium lignosulfonate. Further reactivity of Lignin-p-BOC was demonstrated as a potential reactive filler in green plastic and as potential crosslinker in design of bioresorbable composite polymeric implants. Furthermore, the effects of the modification on the breakdown rate of alkali lignin by microbial (white rot fungus <i>P. chrysosporium</i>) was investigated, and the results showed that the modification obviously decreased <a>the breakdown rate</a>.

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Tosylation and Characterization of Lignin in Water

Cited by 16 publications

References 24 publications

Chemical Modification of Poly(Vinyl Alcohol) in Water

Chemical Modification of Poly(Vinyl Alcohol) in Water

Lignin-graft-Polyoxazoline Conjugated Triazole a Novel Anti-Infective Ointment to Control Persistent Inflammation

Tunable Boc Modification of Lignin and Its Impact on Microbial Degradation Rate

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