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Chiral ionic liquid and its preparing method

A chiral ionic liquid and ionic liquid technology, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc. In the initial stage, the types of chiral ionic liquids are limited, etc., to achieve large structural diversity and designability, which is conducive to large-scale industrial production and low cost

Inactive Publication Date: 2006-03-22
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] At present, there are very few types of chiral ionic liquids, and their application research is still in its infancy.
In addition, due to the limited types of anions in ionic liquids, and the diversity of substituents on cations, the fine-tuning of the physical and chemical properties of ionic liquids mainly depends on the adjustment of substituents on cations, while the above-mentioned chiral ionic liquids The chiral sites are all on the cations, which makes the current types of chiral ionic liquids limited, and it is difficult to adjust the physical and chemical properties of ionic liquids as needed

Method used

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  • Chiral ionic liquid and its preparing method

Examples

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Embodiment 1

[0028] Synthesis of 1-ethyl-3-methylimidazole L-lactate

[0029] in N 2 Under protection, N-methylimidazole (41g, 0.50mol) and bromoethane (54.5g, 0.55mol) were added in a three-neck round bottom flask equipped with a magnetic rotor and a reflux condenser, and the solvent benzene (100g) was added, Heated to 80°C in an oil bath and stirred for 48 hours. After cooling, the ionic liquid and the solvent were separated. After separation, the lower liquid was washed three times with ethyl acetate to remove residual reactants, and then washed with ether to remove residual ethyl acetate, followed by vacuum distillation at 70°C for 48 hours After that, 1-ethyl-3-methylimidazolium chloride was obtained. Dissolve 1-ethyl-3-methylimidazolium bromide (emimBr, 95.5g, 0.50mol) in 60g of dichloromethane, then add L-sodium lactate (56.0g, 0.50mol), in an ice bath (0°C) The reaction was stirred for 10 hours, then filtered. 90°C, 10 3 Dichloromethane was removed by evaporation on a rotary e...

Embodiment 2

[0031] Synthesis of 1-butyl-3-methylimidazole L-lactate

[0032] in N 2 Under protection, N-methylimidazole (41g, 0.50mol) and chlorobutane (50.9g, 0.55mol) were added in a three-necked round bottom flask equipped with a magnetic rotor and a reflux condenser, and the solvent toluene (80g ), heated to 70°C in an oil bath, and stirred for 72 hours. After cooling, the ionic liquid and the solvent were separated. After separation, the lower liquid was washed three times with ethyl acetate to remove residual reactants, and then washed with ether to remove residual ethyl acetate, followed by vacuum distillation at 70°C for 48 hours After that, 1-butyl-3-methylimidazolium chloride was obtained. Dissolve 1-butyl-3-methylimidazolium chloride (43.64g, 0.25mol) in 160g of acetone, then add L-potassium lactate (64.0g, 0.50mol), stir and react at 30°C for 5 hours, then filter . 80°C, 5×10 3 Evaporate in a rotary evaporator under Pa for 10 hours to remove acetone, then put it in a vacu...

Embodiment 3

[0034] Synthesis of 1,3-dihexylimidazole D-lactate

[0035] N 2 Under protection, add N-trimethylsilyl imidazole (72g, 0.50mol) and bromo-n-hexane (181.6g, 1.1mol) in the round bottom flask equipped with magnetic rotor and reflux condenser, add solvent toluene (150g) , reflux reaction at 100°C for 12 hours, after cooling, the layers were separated, and after liquid separation, the lower liquid was dissolved in dry acetonitrile, and the impurities were repeatedly extracted with n-hexane three times, and the acetonitrile was removed by vacuum distillation to obtain 1,3-dihexylimidazolium bromide Compound (hhimBr), dried at 70°C for 48 hours to obtain 1,3-dihexylimidazolium bromide. 1,3-Dihexylimidazolium bromide (158.5 g, 0.5 mol) was dissolved in 30.8 g of chloroform, then L-magnesium lactate (40.4 g, 0.20 mol) was added, stirred at room temperature for 10 hours, and then filtered. Evaporate in a rotary evaporator at 40°C and 1000Pa for 24 hours to remove chloroform, then put...

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Abstract

The present invention is chiral ionic liquid and its preparation process, and features that inside solvent capable of dissolving ionic liquid and incapable of dissolving haloid generated in the double decomposition reaction, chiral lactate and ionic liquid with halogen ion as anion react to obtain chiral ionic liquid with structural general expression [C]+[A]- and comprising cation [C]+ and chiral lactate radical anion [A]-. Compared with available technology, the present invention has the advantages of simple preparation process and easy realization, and the prepared chiral ionic liquid has the advantages of ionic liquid being non-volatile, non-toxic, wide liquid state temperature range, etc. and the advantages of chiral matter with high selectivity, chrial induction effect, etc. and is expected to be used as chiral catalyst, chiral solvent and other green chemical material.

Description

technical field [0001] The invention belongs to the technical field of novel chemical materials and their preparation, and in particular relates to a chiral ionic liquid and a preparation method thereof, in particular to a novel chiral ionic liquid whose anion is lactate and a preparation method thereof. technical background [0002] Environmental pollution is one of the major problems faced by human beings, and chemical industry is the main source of environmental pollution, among which volatile organic solvents (VOCs) commonly used in the chemical industry are an important source of pollution in the chemical industry. With the intensification of environmental problems and the improvement of people's awareness of environmental protection, scientists have been working hard to find alternatives to environmentally harmful substances. Ionic liquids used to replace volatile organic solvents have naturally become one of the research hotspots in green chemistry. [0003] Ionic li...

Claims

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Application Information

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IPC IPC(8): C07D213/18C07D233/58C07C211/62C07F9/54
Inventor 吴林波王伟超李伯耿
Owner ZHEJIANG UNIV
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