Understanding the Role of Cholinium Carboxylate Ionic Liquids in PEG-Based Aqueous Biphasic Systems

Mourão, Teresa; Tomé, Liliana C.; Florindo, Catarina; Rebelo, Luís Paulo N.; Marrucho, Isabel M.

doi:10.1021/sc500444w

Cited by 61 publications

(49 citation statements)

References 41 publications

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“…However, imidazolium‐based ILs display some toxicity and may compromise the biological activity of several molecules, thus motivating the research on more benign ILs to be applied in ABS. Albeit some reports have appeared in the past few years with this issue in mind, these studies were mainly carried out with cholinium‐based ILs, either combined with salts or with polymers to create ABS . Nevertheless, nowadays, there are other ILs derived from natural sources and that could be explored in the creation of ABS.…”

Section: Introductionmentioning

confidence: 99%

“…Albeit some reports have appeared in the past few years with this issue in mind, these studies were mainly carried out with cholinium-based ILs, either combined with salts or with polymers to create ABS. [19][20][21][22][23][24][25] 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%

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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: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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“…Wei et al [3] studied theoretically the reaction of 1-butyl-3-methylimidazolium cation ([bmim] + ) with α-and β-glucose in presence and absence of triethylamine (base). Besides, the use of ILs as dissolution and derivatization media, imidazolium based ILs have also been proposed [28,29] to be an effective compound for the formation of aqueous biphasic systems (ABS).…”

Section: Introductionmentioning

confidence: 99%

Volumetric properties of 1-butyl-3-methylimidazolium bromide in aqueous solutions of d(−)-ribose and d(−)-arabinose at different temperatures

Singh

Banipal

et al. 2015

Journal of Molecular Liquids

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“…Only a minimal discrepancy between the values from literature and our results was found. For example, we found a glass transition temperature for choline malonate ([Ch][Mal]) of −67 °C, while Mourão, et al reported −65 °C [31].…”

Section: Introductionmentioning

confidence: 91%

“…[Ch][Mal]) of −67 °C, while Mourão, et al reported −65 °C[31].Decomposition temperatures were measured to evaluate the thermal stability of the ILs. The Thermogravimetric Analysis (TGA) results for 5% mass decomposition in nitrogen and synthetic air obtained with a heating rate of 10 °C·min −1 are presented inTable 1.…”

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confidence: 99%

Influence of Carboxylate Anions on Phase Behavior of Choline Ionic Liquid Mixtures

et al. 2020

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Mixing ionic liquids is a suitable strategy to tailor properties, e.g., to reduce melting points. The present study aims to widen the application range of low-toxic choline-based ionic liquids by studying eight binary phase diagrams of six different choline carboxylates. Five of them show eutectic points with melting points dropping by 13 to 45 • C. The eutectic mixtures of choline acetate and choline 2-methylbutarate were found to melt at 45 • C, which represents a remarkable melting point depression compared to the pure compounds with melting points of 81 (choline acetate) and 90 • C (choline 2-methylbutarate), respectively. Besides melting points, the thermal stabilities of the choline salt mixtures were investigated to define the thermal operation range for potential practical applications of these mixtures. Typical decomposition temperatures were found between 165 and 207 • C, with choline lactate exhibiting the highest thermal stability.Advantages of DESs compared to pure ILs include easy preparation and therefore low production costs, increased biocompatibility in case of certain components, and bigger variety for customization concerning acidity, hydrophobicity, or polarity. DES systems have demonstrated their practical use in several applications, such as interfacial polymerizations [7], electrochemistry [8], and organic reactions [9].So far, the published research describing IL mixtures has mainly focused on imidazolium [10,11], pyrrolidinium [12], and pyridinium [13] ILs. In these works, significant melting point suppression effects were found for the respective eutectic mixtures. However, imidazolium, pyrrolidinium, and pyridinium ILs and their mixtures face some limitations when it comes to large-scale applications in contact with microorganisms or living matter [14]. Challenges include toxicity aspects and the cost for the organic cation synthesis. This is why a more detailed investigation of choline salts is highly interesting. Based on the available literature, choline salts are characterized by their low toxicity for different cell-lines [15,16], bacteria [17], and other organisms [18]. Moreover, choline salts are industrially available on a large scale.The most widely studied choline salt used in eutectic mixtures is choline chloride [19][20][21][22][23][24][25][26]. One of the first reported DESs was a mixture of choline chloride (liquefaction temperature 302 • C), and urea (melting point 134 • C) that resulted in a 2:1 molar mixture with a remarkable melting point suppression to 12 • C [4]. The typical strategy was to combine choline ILs with molecular compounds such as carboxylic acids, alcohols, and urea derivates [27], and such choline-based DESs have been used in various applications, e.g., as drug solubilization vehicles [28][29][30]. Note, however, that by mixing a choline IL with molecular substances, some of the very attractive IL properties, e.g., non-volatility, non-flammability, and high ionic conductivity can get lost to a large extent. This is why the mixing of two choline ILs is ...

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Understanding the Role of Cholinium Carboxylate Ionic Liquids in PEG-Based Aqueous Biphasic Systems

Cited by 61 publications

References 41 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

Volumetric properties of 1-butyl-3-methylimidazolium bromide in aqueous solutions of d(−)-ribose and d(−)-arabinose at different temperatures

Influence of Carboxylate Anions on Phase Behavior of Choline Ionic Liquid Mixtures

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