Dicarboxylic hydrogen salt ionic liquid with asymmetric chemical structure and weak acidity, and preparation method thereof

A dicarboxylic acid hydrogen salt, ionic liquid technology, applied in the preparation of carboxylate, the preparation of organic compounds, organic chemistry and other directions, can solve the problems of many reaction steps, complex synthesis process, high melting point, and achieve product yield and High purity, cheap and easy-to-obtain raw materials, and simple synthesis methods

Inactive Publication Date: 2012-06-27
南京大学扬州化学化工研究院 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the ionic liquid thus constituted is also weakly acidic, on the one hand, the properties such as the melting point and viscosity of the ionic liquid are not ideal, and on the other hand, their synthesis process is complicated, the reaction steps are many, and the separation and purification process is not easy. This leads to the high production cost of ionic liquids, which is not practical
H.Ohno et al. (Chem.Commun., 2007, 29, 3089-3091; Green Chem., 2007, 11(9), 1155-1157) have synthesized several tetrabutyl quaternary phosphine or choline as cations Weakly acidic dibasic carboxylic acid hydrogen salt ionic liquid, but these ionic liquids have high melting point and high viscosity, and various physical and chemical properties are not ideal, which greatly limits the application of this type of ionic liquid, which is different from this type of ion The unreasonable design of the chemical structure of the cation in the liquid is closely related to
In general, weakly acidic functionalized ionic liquids with low melting point and low viscosity are still relatively scarce, and the production cost of preparing weakly acidic functionalized ionic liquids containing carboxyl groups is still high, and large-scale industrial production of ionic liquids has not yet been achieved. this bottleneck

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  • Dicarboxylic hydrogen salt ionic liquid with asymmetric chemical structure and weak acidity, and preparation method thereof
  • Dicarboxylic hydrogen salt ionic liquid with asymmetric chemical structure and weak acidity, and preparation method thereof
  • Dicarboxylic hydrogen salt ionic liquid with asymmetric chemical structure and weak acidity, and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0017] Embodiment 1: trimethylbutyl quaternary ammonium hydrogen malonate ionic liquid

[0018] Add 15.12g (0.1mol) of trimethylbutylammonium chloride, 14.22g (0.1mol) of potassium hydrogen malonate and 15g of solvent butanol into a 250mL reaction flask respectively, react for 30 seconds under 240W microwave, take out and stir Mix well, then put it into the microwave to react for 15 seconds, take it out and stir well, repeat the last step 3 times. After the reaction was completed, filter while it was hot, and the filtrate was rotary evaporated to remove and recover most of the solvent butanol, and vacuum-dried at 70°C for 48 hours to obtain the product trimethylbutyl quaternary ammonium hydrogen malonate ionic liquid, and the product yield was 95% %, chloride ion concentration 620ppm. Its chemical structural formula is:

[0019]

[0020] Characterization results: elemental analysis theoretical value C: 54.77%, H: 9.65%, N: 6.38%, measured value C: 54.75%, H: 9.61%, N: 6.4...

Embodiment 2

[0021] Embodiment 2: trimethylbutyl quaternary ammonium hydrogen succinate ionic liquid

[0022] Add 15.12g (0.1mol) of trimethylbutylammonium chloride, 15.62g (0.1mol) of potassium hydrogen succinate, and 30g of butanol as a solvent into a 250mL reaction flask, react under a 240W microwave for 30 seconds, take out and stir Mix well, then put it into the microwave for 15 seconds, take it out and stir well, repeat the last step 5 times. After the reaction was completed, it was filtered while it was hot, and the filtrate was rotary evaporated to remove and recover most of the solvent butanol, and dried in vacuum at 70°C for 48 hours to obtain the product trimethylbutyl quaternary ammonium hydrogen succinate ionic liquid, and the product yield was 96 %, chloride ion concentration 716ppm. Its chemical structural formula is:

[0023]

[0024] Characterization results: elemental analysis theoretical value C: 56.63%, H: 9.94%, N: 6.00%, measured value C: 56.65%, H: 9.91%, N: 6.0...

Embodiment 3

[0025] Embodiment 3: Trimethylbutyl quaternary ammonium hydrogen maleate ionic liquid

[0026]In 250mL reaction bottle, add trimethylbutyl ammonium chloride 15.12g (0.1mol) respectively, potassium hydrogen maleate or potassium hydrogen fumarate 15.42g (0.1mol) and solvent butanol 20g, in Under the microwave of 240W, react for 30 seconds, take it out and stir well, then put it into the microwave and react for 15 seconds, take it out and stir well, repeat the last step 4 times. After the reaction is completed, filter while it is hot, and rotate the filtrate to remove and recover most of the solvent butanol, and dry it in vacuum at 70°C for 48 hours to obtain the product trimethylbutyl quaternary ammonium hydrogen maleate ionic liquid or trimethylbutanol The base quaternary ammonium hydrogen fumarate ionic liquid has a product yield of 96% and a chloride ion concentration of 680ppm. Its chemical structural formula is:

[0027]

[0028] Characterization results: elemental ana...

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Abstract

The invention relates to a dicarboxylic hydrogen salt ionic liquid with an asymmetric chemical structure and a weak acidity. The cation of the ionic liquid is a tetraalkyl quaternary ammonium cation with the asymmetric structure or an N,N-dialkylimidazole cation with the asymmetric structure, and the anion is a dicarboxylic hydrogen radical anion. The ionic liquid of the invention, which has a low viscosity and a low melting point, can truly meet industrial application requirements. According to the invention, chlorinated tetraalkyl quaternary ammonium with the asymmetric structure or chlorinated N,N-dialkylimidazole with the asymmetric structure and potassium hydrogen dicarboxylate are adopted as raw materials, the target ionic liquid is obtained through one-step synthesis by adopting a microwave process, and the ionic liquid which has the advantages of simple preparation process, high product yield and purity, no byproduct, and low synthetic cost is very suitable for the industrialized production. The dicarboxylic hydrogen salt ionic liquid with the asymmetric chemical structure and the weak acidity of the invention can be used to rapidly and efficiently absorb SO2. The invention discloses a preparation method of the ionic liquid.

Description

technical field [0001] The invention relates to a kind of dibasic carboxylate hydrogen salt ionic liquid with asymmetric chemical structure and weak acidity and a preparation method thereof. Background technique [0002] Ionic liquid is a green solvent or reaction medium newly developed in recent years. It is composed of organic cations and organic or inorganic anions, and is a type of organic molten salt in a liquid state at room temperature or within a range from room temperature to 100 °C. Ionic liquids have many special properties such as "zero" vapor pressure, low melting point, high thermal stability, and high solubility. They are known as a new generation of "green solvents" and have great application prospects in many fields such as chemical engineering. At present, more than 2,000 kinds of ionic liquids have been discovered and reported in the literature. According to the different organic cation precursors, ionic liquids can be roughly divided into four categories:...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/63C07D233/58C07C55/08C07C57/145C07C55/10C07C55/12C07C209/00C07C51/41B01D53/14
Inventor 吴有庭黄宽陶端健胡兴邦张志炳
Owner 南京大学扬州化学化工研究院
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