Role of choline formate ionic liquid in the polymerization of vinyl and methacrylic monomers

Sundar, D. Sathish; Vijayaraghavan, R.; Subramaniam, J.; Surianarayanan, M.; Mandal, Asit Baran

doi:10.1002/app.33609

Cited by 10 publications

(4 citation statements)

References 41 publications

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“…Choline-based ILs have also gained some notoriety for some highly unusual or niche applications (in addition to their antimicrobial applications which will be described in section 4.6), including the use of choline-derivatives like alkoxymethyl(2-decanoyloxyethyl)dimethylammonium bis(trifluoromethylsulfonyl) as formalin-replacing fixatives for soft tissues, 166 choline hydroxide as a base catalyst for converting propylene oxide to 1-methoxy-2-propanol, 168 use of choline proline on heat-treated mesoporous carbons for catalyzing the Michael reaction between cyclohexanone and β-nitrostyrene, 169 choline formate as both an initiator and a solvent for the polymerizations of vinyl and methacrylate monomers, 170 and [choline][Tf 2 N] as a proton acceptor in a fast intermolecular proton transfer between the cation’s hydroxyl group and an acid [1,1,1-trifluoro- N -(trifluoromethylsulfonyl)methanesulfoneamide]. 316 …”

Section: Applications Of Ether- and Hydroxyl-functionalized Ilsmentioning

confidence: 99%

“…Other physicochemical properties (such as activity coefficients at infinite dilution, Hildebrand solubility parameters, surface tension, contact angle, and wetting film stability) of pure and mixtures of oxygen-grafted ILs can be found in the literature for hydroxyl ammoniums 105,[159][160][161][162][163][164] (including cholinebased ILs [165][166][167][168][169][170] ), hydroxyl imidazoliums, 103,[171][172][173][174] hydroxyl pyridiniums, [175][176][177][178] ether-functionalized ammoniums, 179 and ether-functionalized imidazolium based ILs. 180…”

Section: Other Propertiesmentioning

confidence: 99%

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Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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In recent years, the designer nature of ionic liquids (ILs) has driven their exploration and exploitation in countless fields among the physical and chemical sciences. A fair measure of the tremendous attention placed on these fluids has been attributed to their inherent designer nature. And yet, there are relatively few examples of reviews which emphasize this vital aspect in an exhaustive or meaningful way. In this critical review, we systematically survey the physicochemical properties of the collective library of ether- and alcohol-functionalized ILs, highlighting the impact of ionic structure on features such as viscosity, phase behavior/transitions, density, thermostability, electrochemical properties, and polarity (e.g., hydrophilicity, hydrogen bonding capability). In the latter portions of this review, we emphasize the attractive applications of these functionalized ILs across a range of disciplines, including their use as electrolytes or functional fluids for electrochemistry, extractions, biphasic systems, gas separations, carbon capture, carbohydrate dissolution (particularly, the (ligno)celluloses), polymer chemistry, antimicrobial and antielectrostatic agents, organic synthesis, biomolecular stabilization and activation, and nanoscience. Finally, this review discusses anion-functionalized ILs, including sulfur- and oxygen-functionalized analogs, as well as choline-based deep eutectic solvents (DESs), an emerging class of fluids which can be sensibly categorized as semi-molecular cousins to the IL. Finally, the toxicity and biodegradability of ether- and alcohol-functionalized ILs are discussed and cautiously evaluated in light of recent reports. By carefully summarizing literature examples on the properties and applications of oxy-functional designer ILs up till now, it is our intent that this review offer a barometer for gauging future advances in the field as well as a trigger to spur further contemplation of these seemingly inexhaustible and—relative to their potential—virtually untouched fluids. It is abundantly clear that these remarkable fluidic materials are here to stay, just as certain design rules are slowly beginning to emerge. However, in fairness, serendipity also still plays an undeniable role, highlighting the need for both expanded in silico studies and a beacon to attract bright, young researchers to the field.

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Section: Applications Of Ether- and Hydroxyl-functionalized Ilsmentioning

confidence: 99%

Section: Other Propertiesmentioning

confidence: 99%

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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“…Ionic liquids have been investigated in radical polymerization since several years as summarized and discussed in several reviews . Compared to the use of traditional solvents, rates of polymerization are mostly higher in ionic liquids, and molecular weights are often increased .…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquids as Advantageous Reaction Media for Free Radical Polymerization

Strehmel

Wetzel

Laschewsky

2014

Macromolecular Symposia

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Ionic liquids are attractive solvents for polymer synthesis because their properties can be easily and broadly tuned by varying the structure of both the cation and the anion. Application of ionic liquids as reaction medium for free radical polymerization of vinyl monomers, such as methacrylates or styrene, results in high yields and high molecular weights of the polymers. Reasons for these effects are only partially due to the high viscosity of ionic liquids, which may reduce bimolecular termination of the propagating chains, but are also due to solvent cage effects that differ from those in traditional organic solvents because of strong ionic interactions between the individual ions of the ionic liquids. Furthermore, the high dissolving power of ionic liquids for both weakly polar as well as highly polar monomers makes ionic liquids interesting as solvents for statistical copolymerization. Interestingly, variation of the alkyl chain length of substituents at the cation of the ionic liquid allows altering of copolymer composition.

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“…Betaine is a metabolite of choline presents at high levels in the liver and the kidney, and acetylcholine is involved in memory functions and muscle control . In recent years, choline‐based ILs have been widely studied on account of their potential uses for organic synthesis, biomass conversion, gas absorption, polymerization, metal extraction and lubrication . Although these ILs are nontoxic and biodegradable thanks to the nature of their cation, effluents from their treatment may pose environmental problems.…”

Section: Introductionmentioning

confidence: 99%

Biological oxidation of choline‐based ionic liquids in sequencing batch reactors

Mena

Díaz

Rodrı́guez

et al. 2019

J of Chemical Tech & Biotech

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BACKGROUND Ionic liquids (ILs) are salts consisting of an organic cation and an organic or inorganic anion that are potential use for organic synthesis, biomass conversion, gas absorption, polymerization, metal extraction and lubrication. We examined the biodegradability of choline chloride (CholineCl), choline acetate (CholineAc) and choline bis(trifluoromethylsulfonyl)imide (CholineNTf2) in a sequencing batch reactor (SBR) to assess the influence of the IL anion. RESULTS Following acclimation, activated sludge exhibited good activity, and high COD (80–90%) and TOC removal (75–85%) with initial concentrations of CholineCl and CholineAc over the range 0.25–15 mmol L–1. However, increased concentrations of CholineNTf2 in the reactor feed had an inhibitory effect on the sludge. An analysis of the reaction effluent revealed the presence of the main intermediates of choline degradation: ethanol, and methyl‐, dimethyl‐ and trimethylamine. The initial and final microbial communities of the sludge were characterized by pyrosequencing analysis, and the latter was found to consist mainly of Alfa‐, Beta‐ and Gamma‐proteobacteria. CONCLUSION Choline‐based ionic liquids can be efficiently removed in SBRs. Complete choline degradation (0.25–15 mmol L–1) was accomplished at a variable depletion rate depending on the particular IL anion (chloride, acetate or NTf2). © 2019 Society of Chemical Industry

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Role of choline formate ionic liquid in the polymerization of vinyl and methacrylic monomers

Cited by 10 publications

References 41 publications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Ionic Liquids as Advantageous Reaction Media for Free Radical Polymerization

Biological oxidation of choline‐based ionic liquids in sequencing batch reactors

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