Solubility-switchable ionic liquids using a variety of anions

IF 5.3 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Liquids Pub Date : 2025-04-10 DOI:10.1016/j.molliq.2025.127554

Akio Kamimura, Nao Kaneko, Runa Sasakura, Karin Hirota, Takuji Kawamoto, Yuna Deguchi, Tomoya Tashiro, Kenta Fujii

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Abstract

Various solubility switchable ionic liquids containing triflate, PF₆ and BF₄ anions were prepared. The protection-deprotection of the diol moiety in the cationic part was achieved under mild conditions in the presence of small amounts of an acidic ion exchange resin as an acidic catalyst. These relatively mild conditions allowed the conversion from the acetal type to the diol type in a high yield and the hydrolysis of PF₆ and BF₄ was minimized. The reverse conversion from the diol type to the acetal type was also possible in the presence of catalytic amounts of trifluoromethansulfonic acid (TfOH). Subsequent treatment with an alumina column was effectively prevented the hydrolysis of the acetal moiety and the anionic moieties. Partitioning experiments revealed that most of the acetal-type ionic liquids preferred to partition to organic phase regardless of the water-CH₂Cl₂ or water-EtOAc system, while the diol-type ionic liquids mostly preferred to partition to the aqueous phase as long as the number of carbons in the cationic part was less than 13 or 14, which was much larger than the number of carbons in the analogous ionic liquids containing NTf₂ as the anionic part.

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溶解度可切换的离子液体，使用多种阴离子

制备了含三氟酸盐、PF6和BF4阴离子的多种溶解度可调离子液体。在少量酸性离子交换树脂作为酸性催化剂的情况下，在温和的条件下实现了阳离子部分二醇部分的保护-脱保护。这些相对温和的条件使得从缩醛型到二醇型的转化产率高，并且PF6和BF4的水解最小化。在三氟甲烷磺酸（TfOH）的催化量存在下，从二醇型向缩醛型的反向转化也是可能的。随后用氧化铝柱进行处理，有效地防止了缩醛部分和阴离子部分的水解。配分实验表明，无论是水- ch2cl2还是水- etoac体系，大多数缩醛型离子液体都倾向于配分到有机相，而二醇型离子液体只要阳离子部分的碳数小于13或14个，就倾向于配分到水相，这远远大于含有NTf2作为阴离子部分的类似离子液体的碳数。

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来源期刊

Journal of Molecular Liquids 化学-物理：原子、分子和化学物理

CiteScore

10.30

自引率

16.70%

发文量

2597

审稿时长

78 days

期刊介绍： The journal includes papers in the following areas: – Simple organic liquids and mixtures – Ionic liquids – Surfactant solutions (including micelles and vesicles) and liquid interfaces – Colloidal solutions and nanoparticles – Thermotropic and lyotropic liquid crystals – Ferrofluids – Water, aqueous solutions and other hydrogen-bonded liquids – Lubricants, polymer solutions and melts – Molten metals and salts – Phase transitions and critical phenomena in liquids and confined fluids – Self assembly in complex liquids.– Biomolecules in solution The emphasis is on the molecular (or microscopic) understanding of particular liquids or liquid systems, especially concerning structure, dynamics and intermolecular forces. The experimental techniques used may include: – Conventional spectroscopy (mid-IR and far-IR, Raman, NMR, etc.) – Non-linear optics and time resolved spectroscopy (psec, fsec, asec, ISRS, etc.) – Light scattering (Rayleigh, Brillouin, PCS, etc.) – Dielectric relaxation – X-ray and neutron scattering and diffraction. Experimental studies, computer simulations (MD or MC) and analytical theory will be considered for publication; papers just reporting experimental results that do not contribute to the understanding of the fundamentals of molecular and ionic liquids will not be accepted. Only papers of a non-routine nature and advancing the field will be considered for publication.