Surface-active ionic liquids in micellar catalysis: impact of anion selection on reaction rates in nucleophilic substitutions

Cognigni, Alice; Gärtner, Peter; Zirbs, Ronald; Peterlik, Herwig; Prochazka, Katharina; Schröder, Christian; Bica, Katharina

doi:10.1039/c6cp00493h

Cited by 70 publications

(51 citation statements)

References 63 publications

(109 reference statements)

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“…12,13 More recently, the properties of catanionic ionic liquids, containing both anions and cations with hydrophobic tails, have proved to be exceptional. 14,15 Surface-active ionic liquids have already been well explored for a number of applications in synthesis, 16,17 catalysis 18,19 and separations 20,21 rendering them ideally suited for the development of targeted microemulsions, 22−26 and for their separation. 27 …”

Section: Introductionmentioning

confidence: 99%

Ionic Liquid-Based Microemulsions in Catalysis

et al. 2016

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Section: Introductionmentioning

confidence: 99%

Ionic Liquid-Based Microemulsions in Catalysis

et al. 2016

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“…Table also exhibited the CMC values concerning to 1‐methyl, 3‐octyl/3‐dodecylimidazolium trifluoroacetate and 1‐methyl, 3‐dodecylimidazolium methanesulfonate (Cognini et al, ; Šarac et al, ; Wang et al, ). Comparing these values with the corresponding 1‐alkylimidazolium derivatives, it can be observed that these last SAIL display lower CMC values.…”

Section: Resultsmentioning

confidence: 99%

“…Both cationic and anionic SAIL have been designed and investigated for their self‐assembly by changing the alkyl chain length, charged head group structure, functional groups, and counterions (Anouti et al, ; Baker et al, ; Blesic et al, , ; Galgano and El Seoud, ; García et al, ; Pillai et al, ; Rao et al, ; Šarac et al, ; Singh et al, ; Wang et al, ; Wang and Wang, ). The high tunability of IL opens up a broad range of applications for SAIL such as in micellar catalysis (Adam et al, ; Bica et al, ; Cognini et al, ) and in analytical chemistry and separation science (de Faria et al, ; Pino et al, ; Ressman et al, ). It was also demonstrated that some SAIL can be effective alternatives to the surfactants commonly used in enhanced oil recovery (EOR) processes with important advantages over the traditional surfactants and polymer‐flooding methods (Bera and Belhaj, ; Lago et al, ; Zhou et al, ).…”

Section: Introductionmentioning

confidence: 99%

“…* Claudia G. Adam cadam@conicet.gov.ar * Graciela G. Fortunato gfortuna@fiq.unl.edu.ar 2014; Šarac et al, 2017;Singh et al, 2016;Wang et al, 2008;Wang and Wang, 2014). The high tunability of IL opens up a broad range of applications for SAIL such as in micellar catalysis (Adam et al, 2017;Bica et al, 2012;Cognini et al, 2016) and in analytical chemistry and separation science (de Faria et al, 2017;Pino et al, 2012;Ressman et al, 2013). It was also demonstrated that some SAIL can be effective alternatives to the surfactants commonly used in enhanced oil recovery (EOR) processes with important advantages over the traditional surfactants and polymer-flooding methods (Bera and Belhaj, 2016;Lago et al, 2012;Zhou et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Self‐Assembly Properties of New Surface‐Active 1‐Alkylimidazolium Ionic Liquids in Aqueous Media

Adam

Fortunato

2019

J Surfact & Detergents

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New cationic surface‐active ionic liquids (SAIL) were synthesized using 1‐alkylimidazolium cations [CnHim] (n = 8, 10, 12, 14, and 16) with trifluoroacetate ([CF3CO2]) and methanesulfonate ([CH3SO3]) anions as counterions. Their self‐aggregation behavior in water was investigated using electrical conductivity and fluorescence measurements. Based on the obtained results, the critical micellar concentration (CMC), the degree of counterion dissociation, α, the Gibbs free energy of micelle formation, normalΔGmic0, and the mean aggregation number (Nagg) were determined. The analysis of these parameters indicates that these new SAIL exhibit certain improved properties with respect to traditional cationic surfactants. Furthermore, SAIL with [CF3CO2] counterions exhibit lower CMC values than alkyltrimethylammonium bromide (CnTAB)‐type surfactants and their dialkylimidazolium counterparts with the same alkyl chain length. It was demonstrated that, in the studied SAIL, the hydrophobic probe pyrene resides deeper inside the palisade layer of the micelle and the estimated E T(30) polarity values of micellar pseudophase confirm this result. The abovementioned outcomes demonstrate that the 1‐alkylimidazolium cation is suitable to promote aggregation when it is accompanied by the appropriate counterions. Consequently, this contribution becomes a valuable first step toward the potential application of these compounds as a new class of “designed cationic surfactants.”

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“…In recent years, several applications of ionic liquids (ILs) as micellar catalysts have been developed [23][24][25][26]. However, their application as micellar epoxidation catalyst has not yet been reported.…”

Section: Introductionmentioning

confidence: 99%

Kinetic Model of Two‐Phase Epoxidation with Ionic Liquids as Micellar Catalysts

et al. 2018

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The biphasic catalytic epoxidation of cyclooctene using the ionic liquid (IL) 1,2‐dimethyl‐3‐octyl‐imidazolium perrhenate ([OMMIM]ReO4) as micellar catalyst and H2O2 as oxidant was investigated. Kinetic experiments were carried out in the intrinsic kinetic regime as proved by variation of stirring rate and temperature. Variation of catalyst concentration allowed for determination of the critical micellar concentration (CMC) of the catalytic IL. The effect of substrate concentrations on the reaction rate was also assessed. Based on the experiments, a kinetic model adapted from enzyme catalysis was proposed to account for the micellar reaction environment. The model takes into account the onset of micelle formation at the CMC. The application of the kinetic model illustrated the good agreement with the experimental data. The model will be applied to other micellar epoxidation reactions and for the design of an appropriate reaction setup in the future.

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Surface-active ionic liquids in micellar catalysis: impact of anion selection on reaction rates in nucleophilic substitutions

Abstract: A series of surface-active ionic liquids based on the 1-dodecyl-3-methylimidazolium cation and different anions was synthesized and applied for micellar catalysis of nucleophilic substitutions.

Cited by 70 publications

References 63 publications

Ionic Liquid-Based Microemulsions in Catalysis

Ionic Liquid-Based Microemulsions in Catalysis

Synthesis and Self‐Assembly Properties of New Surface‐Active 1‐Alkylimidazolium Ionic Liquids in Aqueous Media

Kinetic Model of Two‐Phase Epoxidation with Ionic Liquids as Micellar Catalysts

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