Syntheses and characterisation of hydrophobic ionic liquids containing trialkyl(2-ethoxy-2-oxoethyl)ammonium or N-(1-methylpyrrolidyl-2-ethoxy-2-oxoethyl)ammonium cations

Messadi, Ahmed; Mohamadou, Aminou; Boudesocque, Stéphanie; Dupont, Laurent; Fricoteaux, Patrick; Nguyen-Van-Nhien, Albert; Courty, Matthieu

doi:10.1016/j.molliq.2013.04.023

Cited by 20 publications

(13 citation statements)

References 25 publications

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“…AGB‐ILs were synthesized by us according to previously reported protocols . The ILs triethyl[2‐ethoxy‐2‐oxoethyl]ammonium bromide ([Et 3 NC 2 ]Br), tri(n‐propyl)[2‐ethoxy‐2‐oxoethyl]ammonium bromide ([Pr 3 NC 2 ]Br), tri(n‐butyl)[2‐ethoxy‐2‐oxoethyl]ammonium bromide ([Bu 3 NC 2 ]Br), tri(n‐butyl)[2‐ethoxy‐2‐oxoethyl]phosphonium bromide ([Bu 3 PC 2 ]Br), and N‐(1‐methylpyrrolidyl‐2‐ethoxy‐2‐oxoethyl)ammonium bromide ([MepyrNC 2 ]Br) were synthesized by the reaction of ethyl 2‐bromoacetate and triethylamine, tri( n ‐propyl)amine, tri( n ‐butyl)amine, tri( n ‐butyl)phosphine or N‐methylpyrrolidine, respectively.…”

Section: Methodssupporting

confidence: 91%

“…Materials AGB-ILs were synthesized by us according to previously reported protocols. 26 Br) were synthesized by the reaction of ethyl 2-bromoacetate and triethylamine, tri(n-propyl)amine, tri(n-butyl)amine, tri(n-butyl)phosphine or Nmethylpyrrolidine, respectively. All ILs were dried under vacuum for at least 72h at 458C.…”

Section: Methodsmentioning

confidence: 99%

“…Nevertheless, nowadays, there are other ILs derived from natural sources and that could be explored in the creation of ABS. Among these, analogues of glycine‐betaine (AGB) can be seen as a promising alternative …”

Section: Introductionmentioning

confidence: 99%

“…Among these, analogues of glycine-betaine (AGB) can be seen as a promising alternative. 26 Glycine-betaine is composed of a zwitterionic quaternary tri(methyl)amine bearing an acetate group. These organic osmolytes accumulate in a wide variety of plant species in response to environmental stress.…”

Section: Introductionmentioning

confidence: 99%

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Glycine‐betaine ionic liquid analogues as novel phase‐forming components of aqueous biphasic systems

Pereira

Almeida

Gomes

et al. 2018

Biotechnology Progress

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Given the biotechnology advances observed in recent years in terms of upstream, the development of effective downstream processes becomes mandatory to decrease the associated costs of biotechnological-based products. Although a large interest has been devoted to ionic-liquid-based aqueous biphasic systems (IL-based ABS) as tailored separation platforms, imidazolium-based ILs have been the preferred choice as phase-forming agents. To overcome some toxicity and biodegradability issues associated to imidazolium-based ILs, novel ABS composed of ILs analogues of glycine-betaine (AGB-ILs) are here proposed and investigated. Five AGB-ILs were synthesized, characterized in terms of ecotoxicity, and applied toward the development of novel ABS formed with Na SO . Three commercial ILs were also investigated for comparison purposes. The respective ABS ternary phase diagrams, as well as the tie-lines and tie-line lengths, were determined at 25°C. Finally, their performance as extraction strategies was evaluated with five amino acids (L-tryptophan, L-phenylalanine, D-phenylalanine, L-tyrosine and L-3,4-dihydroxyphenylalanine/L-dopa). In all studied systems amino acids preferentially migrate to the IL-rich phase, and with AGB-ILs, the amino acid extraction efficiencies to the IL-rich phase range between 65% and 100%, obtained in a single-step. Furthermore, the studied AGB-ILs display a higher ability to form ABS and to extract amino acids than ABS composed of more traditional and commercial ILs. In summary, novel ABS composed of AGB-ILs can be formed and used as separation routes of value-added compounds of biotechnological interest. © 2018 American Institute of Chemical Engineers Biotechnol. Prog., 2018 © 2018 American Institute of Chemical Engineers Biotechnol. Prog., 34:1205-1212, 2018.

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Section: Methodssupporting

confidence: 91%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Glycine‐betaine ionic liquid analogues as novel phase‐forming components of aqueous biphasic systems

Pereira

Almeida

Gomes

et al. 2018

Biotechnology Progress

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“…[32][33][34][35][36] Elongation of the alkyl chains from 3t o1 0c arbon atomsl eads to only as mall decreasei nt he stabilityo ft he ILs between successive groups;h owever,i td oes have as lightly more significant effect with drastic changes in the cation size (e.g., [ Pyr 13 ] + ! [38] In addition to the targeted thermals tability study reported herein, it is also well documented in the literature that al onger alkyl chain length is accompanied by lower solubility, higher viscosity,h igherd ensity,s lower diffusion, and lower conductivity. Ad ecrease in thermal stability by about 45 8Ci so bserved upon going from [Pyr 13 ] + to [Pyr 110 ] + (Figure 2a and da nd Table 1.…”

Section: Effect Of Alkyl Chain Lengthsupporting

confidence: 58%

Comprehensive Insights into the Thermal Stability, Biodegradability, and Combustion Chemistry of Pyrrolidinium‐Based Ionic Liquids

et al. 2017

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The use of ionic liquids (ILs) as advanced electrolyte components in electrochemical energy-storage devices is one of the most appealing and emerging options. However, although ILs are hailed as safer and eco-friendly electrolytes, to overcome the limitations imposed by the highly volatile/combustible carbonate-based electrolytes, full-scale and precise appraisal of their overall safety levels under abuse conditions still needs to be fully addressed. With the aim of providing this level of information on the thermal and chemical stabilities, as well as actual fire hazards, herein, a detailed investigation of the short- and long-term thermal stabilities, biodegradability, and combustion behavior of various pyrrolidinium-based ILs, with different alkyl chain lengths, counteranions, and cations, as well as the effect of doping with lithium salts, is described.

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Ecotoxicity interspecies study of ionic liquids based on phosphonium and ammonium cations

Errazquin

Mohamadou

Dupont

et al. 2021

Environ Sci Pollut Res

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Syntheses and characterisation of hydrophobic ionic liquids containing trialkyl(2-ethoxy-2-oxoethyl)ammonium or N-(1-methylpyrrolidyl-2-ethoxy-2-oxoethyl)ammonium cations

Cited by 20 publications

References 25 publications

Glycine‐betaine ionic liquid analogues as novel phase‐forming components of aqueous biphasic systems

Glycine‐betaine ionic liquid analogues as novel phase‐forming components of aqueous biphasic systems

Comprehensive Insights into the Thermal Stability, Biodegradability, and Combustion Chemistry of Pyrrolidinium‐Based Ionic Liquids

Ecotoxicity interspecies study of ionic liquids based on phosphonium and ammonium cations

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