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Amino-acid-based chiral ionic liquids characterization and application in aqueous biphasic systems
Fluid Phase Equilibria ( IF 2.8 ) Pub Date : 2021-05-18 , DOI: 10.1016/j.fluid.2021.113091
Ana R.F. Carreira , Samuel N. Rocha , Francisca A. e Silva , Tânia E. Sintra , Helena Passos , Sónia P.M. Ventura , João A.P. Coutinho

By using amino acids as anions, ten chiral ionic liquids (CILs) composed of tetrabutylammonium or cholinium as cations were synthesized by neutralization reactions and further characterized by assessing their optical rotation, thermophysical properties (melting and decomposition temperatures, density, viscosity and refractive index) and ecotoxicity against the marine bacterium Aliivibrio fischeri. The CILs are shown to display, in general, high thermal stability (> 439 K) and low to moderate toxicities (86-217 mg∙L−1). It was found that the cation plays an important role in the density and viscosity of the CILs. Additionally, the effect of CILs optical configuration on these properties was evaluated by comparing the tetrabutylammonium D/L-phenylalaninate ([N4444][D/L-Phe]) and cholinium D/L-phenylalaninate ([N1112(OH)][D/L-Phe]) pairs. Finally, the CILs potential to form aqueous biphasic systems with sodium sulfate, citrate buffer and phosphate buffer was assessed and the ternary phase diagrams were determined. These allowed to infer the impact of the CILs’ cation, anion, and salt on the aqueous biphasic system formation. It was shown that the cation has a more pronounced impact on the aqueous biphasic system formation than the anion. Cholinium-based CILs failed to form aqueous biphasic systems with sodium sulfate under the tested conditions, contrary to the more hydrophobic tetrabutylammonium-based CILs. The ability of the tested salt and buffers to induce liquid-liquid demixing shows that citrate buffer and sodium sulfate represent the weakest and the strongest salting-out agents, respectively.



中文翻译:

基于氨基酸的手性离子液体表征及在水性双相体系中的应用

通过使用氨基酸作为阴离子,通过中和反应合成了由四丁基铵或胆碱作为阳离子的十种手性离子液体 (CIL),并通过评估它们的旋光度、热物理性质(熔融和分解温度、密度、粘度和折射率)进一步表征和对海洋细菌Aliivibrio fischeri 的生态毒性。一般而言,CIL 显示出高热稳定性 (> 439 K) 和低至中等毒性 (86-217 mg∙L -1 )。发现阳离子在CILs的密度和粘度中起重要作用。此外,通过比较 D/L-苯丙氨酸四丁基铵 ([N 4444][D/L-Phe]) 和胆碱 D/L-苯丙氨酸盐 ([N 1112(OH)][D/L-Phe]) 对。最后,评估了 CIL 与硫酸钠、柠檬酸盐缓冲液和磷酸盐缓冲液形成水性双相系统的潜力,并确定了三元相图。这些允许推断 CIL 的阳离子、阴离子和盐对水性双相系统形成的影响。结果表明,与阴离子相比,阳离子对水性双相体系的形成具有更显着的影响。与疏水性更强的四丁基铵基 CILs 相比,基于胆碱的 CILs 在测试条件下未能与硫酸钠形成水性双相体系。测试的盐和缓冲液诱导液-液分层的能力表明柠檬酸盐缓冲液和硫酸钠分别代表最弱和最强的盐析剂。

更新日期:2021-06-02
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