Cellulose acetate fibers prepared from different raw materials with rapid synthesis method

Chen, Jinghuan; Xu, Jikun; Wang, Kun; Cao, Xuefei; Sun, Run‐Cang

doi:10.1016/j.carbpol.2015.11.034

Cited by 91 publications

(67 citation statements)

References 32 publications

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“…Both acetone and acetaldehyde are easy to remove from the reaction mixture and are relatively non-toxic, but flammable. In prior literature, the reactions made with VinAc were either catalyzed with a base; K 2 CO 3 , Na 2 CO 3 (Ç etin et al 2009;Jebrane and Sebe 2007;Jebrane et al 2011), or cellulose was activated with NaOH (Chen et al 2016).…”

Section: Resultsmentioning

confidence: 99%

“…The same group have just recently published an article, where [Emim][OAc] and other imidazolium based ionic liquids were used in DMSO mixtures for assessment of the mechanistic effects of ILs (Kakuchi et al 2017). Vinyl esters can also be used in cellulose esterification reactions, as an acylation reagent, but have been used in ''traditional'' solvents with catalysts or activators (Chen et al 2016;Ç etin et al 2009;Heinze et al 2003;Jebrane et al 2011;Jebrane and Sebe 2007).…”

Section: Introductionmentioning

confidence: 99%

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Homogenous esterification of cellulose pulp in [DBNH][OAc]

2017

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Cellulose acetate is widely used in films, filters, textiles, lacquer and cosmetic products. Herein we demonstrate the production of cellulose esters under homogeneous conditions using 1,5-diazabicyclo[4.3.0]non-5-ene acetate ([DBNH][OAc]) as solvent. The reagents have been chosen such that the system is recyclable, i.e. by-products are low boiling and easy to remove. It is demonstrated that cellulose acetate can be synthesized with different degree of substitution (DS) values, and that some commonly used acylation regents, like vinyl carboxylates react well without additional base catalyst. Low to high DS values are possible with good recovery of high purity ionic liquid (IL). A linear correlation method of two separate methods, IR and 31 P NMR, is proposed to reliably assess the DS of the products. The recyclability of the solvent is demonstrated by acetylating cellulose with isopropenyl acetate to high degree and regeneration into water. After regeneration of cellulose acetate from the IL with addition of water, the residual water was entrained using n-butanol to minimize hydrolysis of [DBNH][OAc], to allow for high recovery and high purity of the ionic liquid. Thus, an overall scheme for batch cellulose acetylation and recovery of [DBNH][OAc] from aqueous solutions is proposed.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Homogenous esterification of cellulose pulp in [DBNH][OAc]

2017

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“…These reactions were chosen due to the importance and wide application of these cellulose derivatives (Fischer et al 2008;Jelínková et al 2002;Zimnitsky et al 2006). Acetylation of cellulose has been widely studied in common non-derivatising cellulose solvents (Heinze et al 2003;Jebrane and Sèbe 2007;Jebrane et al 2011;Chen et al 2016). This reaction is commonly performed in the presence of catalysts (Jebrane et al 2011;Li et al 2009;Chen et al 2014) with different acetylating agents, such as AA (Wu et al 2004;Nawaz et al 2014;Jogunola et al 2016;Granström et al 2008), and recently with vinyl acetate (VinAc) or IPA (Kakko et al 2017;Kakuchi et al 2015Kakuchi et al , 2017.…”

Section: Enhanced Reactivitymentioning

confidence: 99%

Crystallinity reduction and enhancement in the chemical reactivity of cellulose by non-dissolving pre-treatment with tetrabutylphosphonium acetate

et al. 2020

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Herein, we demonstrate the activation of commercial chemical cellulose pulps towards chemical modification by a pre-treatment step with tetrabutylphosphonium acetate ([P 4444 ][OAc]). A heterogeneous (non-dissolving) pre-treatment was applied allowing for a significant reduction in crystallinity, without concomitant formation of the thermodynamically stable cellulose II. An increase in chemical reactivity was demonstrated using two model reactions; (1) acetylation (organic swelling conditions), where high degrees of substitution (DS) were obtained without the need for a catalyst, and (2) 4-acetamido-TEMPO oxidation (aqueous swelling conditions), where significant degrees of oxidation (DO) were obtained, beyond those for the untreated pulps. In both tests a notable improvement in cellulose reactivity was observed. Regioselectivity of acetylation was assessed using 2D NMR for one low and one high DS sample. The low DS showed a small degree of acetylation of the 6-OH, whereas, the high DS from the pre-treated sample showed mainly mixtures of triacetate and diacetates. Important mechanistic information is attained for future development of aqueous and organic-based reactions involving this ionic liquid pre-treatment.

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“…The same authors subsequently reported the acetylation of cellulose (pre-hydrolysis kraft, PHK) in a similar acid-base conjugate ionic liquid. [27] In this case, the ionic liquid was formed by a 1:1 molar combination of the organic super base 1,5- on acetylation of cellulose in ionic liquids requiring pyridine, K 2 CO 3 , [28] or NaOH [29] as catalyst. This was attributed to the excess of the base utilized in the ionic liquid which can act as a catalyst for the acetylation reaction.…”

Section: Scheme 2: Depiction Of the Concept Of Distillable Ionic Liqumentioning

confidence: 99%

Critical Review on Sustainable Homogeneous Cellulose Modification: Why Renewability Is Not Enough

Onwukamike

Grelier

Grau

et al. 2018

ACS Sustainable Chem. Eng.

130

108

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As we mark the 20 th anniversary after the introduction of the twelve principles of green chemistry, sustainable modification of cellulose, being the most abundant biobased polymer, is worth consideration. Many researchers work on this renewable polymer, however the use of non-sustainable solvents, reactants and modification approaches simply shifts the environmental burden to other stages of the life cycle. Therefore, to achieve true sustainable modification of cellulose, its renewability combined with mild and efficient reaction protocols is crucial in order to obtain sustainable materials that will reduce the overall negative effect of the fossil-based resources they are replacing.

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Cellulose acetate fibers prepared from different raw materials with rapid synthesis method

Cited by 91 publications

References 32 publications

Homogenous esterification of cellulose pulp in [DBNH][OAc]

Homogenous esterification of cellulose pulp in [DBNH][OAc]

Crystallinity reduction and enhancement in the chemical reactivity of cellulose by non-dissolving pre-treatment with tetrabutylphosphonium acetate

Critical Review on Sustainable Homogeneous Cellulose Modification: Why Renewability Is Not Enough

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