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Synthesis, Characterisation, and Determination of Physical Properties of New Two-Protonic Acid Ionic Liquid and its Catalytic Application in the Esterification
Australian Journal of Chemistry ( IF 1.1 ) Pub Date : 2020-08-28 , DOI: 10.1071/ch20153
Zohreh Shahnavaz , Lia Zaharani , Nader Ghaffari Khaligh , Taraneh Mihankhah , Mohd Rafie Johan

A new ionic liquid was synthesised, and its chemical structure was elucidated by FT-IR, 1D NMR, 2D NMR, and mass analyses. Some physical properties, thermal behaviour, and thermal stability of this ionic liquid were investigated. The formation of a two-protonic acid salt namely 4,4′-trimethylene-N,N′-dipiperidinium sulfate instead of 4,4′-trimethylene-N,N′-dipiperidinium hydrogensulfate was evidenced by NMR analyses. The catalytic activity of this ionic liquid was demonstrated in the esterification reaction of n-butanol and glacial acetic acid under different conditions. The desired acetate was obtained in 62–88 % yield without using a Dean–Stark apparatus under optimal conditions of 10 mol-% of the ionic liquid, an alcohol to glacial acetic acid mole ratio of 1.3 : 1.0, a temperature of 75–100°C, and a reaction time of 4 h. α-Tocopherol (α-TCP), a highly efficient form of vitamin E, was also treated with glacial acetic acid in the presence of the ionic liquid, and O-acetyl-α-tocopherol (Ac-TCP) was obtained in 88.4 % yield. The separation of esters was conducted during workup without the utilisation of high-cost column chromatography. The residue and ionic liquid were used in subsequent runs after the extraction of desired products. The ionic liquid exhibited high catalytic activity even after five runs with no significant change in its chemical structure and catalytic efficiency.



中文翻译:

新型二质子酸离子液体的合成,表征和物理性质的测定及其在酯化反应中的催化应用

合成了新的离子液体,并通过FT-IR,1D NMR,2D NMR和质量分析阐明了其化学结构。研究了该离子液体的一些物理性质,热行为和热稳定性。通过NMR分析证明形成了4,4'-三亚甲基-NN'-二哌啶硫酸盐二质子酸盐代替4,4'-三亚甲基-NN'-二哌啶硫酸氢盐。该离子液体的催化活性在n的酯化反应中得到证明。-丁醇和冰醋酸在不同条件下。无需使用Dean-Stark装置,就可以在62%至88%的收率下获得所需的乙酸盐,最佳条件是离子液体的含量为10 mol%,醇与冰醋酸的摩尔比为1.3:1.0,温度为75-100 ,反应时间为4 h。α-生育酚(α-TCP)是维生素E的一种高效形式,在离子液体和O的存在下也用冰醋酸处理过以88.4%的产率获得-乙酰基-α-生育酚(Ac-TCP)。酯的分离是在后处理过程中进行的,无需使用昂贵的柱色谱法。提取所需产物后,将残留物和离子液体用于后续运行。该离子液体即使经过五次运行仍显示出高催化活性,其化学结构和催化效率没有明显变化。

更新日期:2020-09-01
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