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Imidazolium bromide ionic liquid containing amine groups and preparation method and application of ionic liquid

An imidazolium bromide, ionic liquid technology, applied in chemical instruments and methods, catalytic reactions, organic chemistry, etc., to reduce costs, ensure catalytic effects, and mild reaction conditions.

Active Publication Date: 2016-09-21
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently researched ionic liquid catalysts cannot meet the following conditions at the same time: high catalytic activity, mild reaction conditions, no need to add additional solvents or co-catalysts, good stability for recycling, etc., which limits their industrial applications.

Method used

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  • Imidazolium bromide ionic liquid containing amine groups and preparation method and application of ionic liquid
  • Imidazolium bromide ionic liquid containing amine groups and preparation method and application of ionic liquid
  • Imidazolium bromide ionic liquid containing amine groups and preparation method and application of ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 has the preparation of the imidazolium bromide salt ionic liquid of monoamino

[0023] The structural formula of the imidazolium bromide salt ionic liquid with monoamino is as follows:

[0024]

[0025] R=CH 3 , C 4 h 9 , CH 2 = CH; n = 2 or 3

[0026] (1) 1-aminopropyl-3-butyl imidazolium bromide ([NH 2 Preparation of pbim]Br)

[0027] Under the protection of nitrogen, mix 3-bromopropylamine hydrobromide and n-butylimidazole at a molar ratio of 1:1.1, dissolve in a certain amount of absolute ethanol solution, reflux at 90°C for 24 hours, and distill under reduced pressure After the ethanol solvent, add dichloromethane solvent, stir, filter, distill the filtrate under reduced pressure to remove dichloromethane, add an appropriate amount of KOH aqueous solution after vacuum drying to make the solution pH 8-9, filter, add absolute ethanol solvent to the solid, Stir and dissolve, filter, and after the filtrate is vacuum-dried, pure 1-aminopropyl-3-bu...

Embodiment 2

[0034] Embodiment 2 has the preparation of the imidazolium bromide salt ionic liquid of two amino groups

[0035] The structural formula of the imidazolium bromide salt ionic liquid with two amino groups is as follows:

[0036]

[0037] R=(CH 2 ) n NH 2 ;n=2 or 3

[0038] (1) 1,3-diaminopropylimidazolium bromide ([2NH 2 pim]Br) preparation:

[0039] Under the protection of nitrogen, mix 3-bromopropylamine hydrobromide and trimethylsilyl imidazole at a molar ratio of 1:2.2, dissolve in a certain amount of absolute ethanol solution, condense and reflux at 90°C for 24 hours, and the reaction solution From clarification to light yellow transparent viscous liquid gradually, after vacuum distillation to remove ethanol solvent, add toluene solvent, stir, filter, distill the filtrate to remove toluene under reduced pressure, add appropriate amount of KOH aqueous solution after vacuum drying to make the solution pH 8-9, Filtrate, add dehydrated ethanol solvent in the solid, st...

Embodiment 3

[0042] Embodiment 3 has the imidazolium bromide salt ionic liquid of amino group to catalyze epoxy compound cycloaddition reaction

[0043] (1) The influence of temperature on the reaction yield

[0044] In a 50ml autoclave, add the catalyst [NH 2 pbim]Br and epichlorohydrin, mixed, passed into 5MP CO 2 , as shown in Table 1, the temperature was reacted for 2 hours. The addition amount of catalyst is 0.6% of the mole number of epichlorohydrin. Calculate the productive rate of cyclic carbonate after the reaction finishes, and the results are shown in Table 1.

[0045] Table 1

[0046] temperature °C

60

80

100

120

140

Yield%

39.6

70.7

82.4

87.5

99.9

[0047] (2) CO 2 Effect of Pressure on Reaction Yield

[0048] The method is the same as (1), the temperature is 140°C, the pressure is changed as shown in Table 2, and the results are shown in Table 2.

[0049] Table 2

[0050] Pressure MP

1

3

5

Yi...

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Abstract

The invention relates to imidazolium bromide ionic liquid containing amine groups and a preparation method and application of the ionic liquid. The structural formula of the imidazolium bromide ionic liquid containing amine groups is shown as the formula (I). Under protection of nitrogen, 3-bromopropylamine hydrobromide or 2-bromoethylamine hydrobromide and imidazole are dissolved in anhydrous ethanol after being mixed, reflux reaction is conducted for 20-25 h at 85-95 DEG C, ethanol is removed through vacuum distillation, an organic solvent is added, stirring and filtering are conducted, the organic solvent is removed from filter liquid through vacuum distillation, a KOH aqueous solution is added after vacuum drying so that the pH of the solution can be 8-9, filtering is conducted, solid is added into anhydrous ethanol and stirred, filtering is conducted again, filter liquid is dried in a vacuum mode, and the target product is obtained. In the process that catalytic epoxidation compound is used for synthesizing cyclic carbonate, the ionic liquid has the advantages that the yield is high, activity is high, no catalysts or solvents are needed, reaction conditions are mild, stability is high, and recycling is conducted many times. Please see the formula (I) in the description.

Description

technical field [0001] The invention belongs to the field of chemical catalysis, and in particular relates to an imidazolium bromide ionic liquid with amino groups and its application in catalyzing carbon dioxide and epoxy compounds to synthesize cyclic carbonates. Background technique [0002] With the progress of human society and the development of industrial production, the amount of carbon dioxide that people emit into the atmosphere is also increasing. Therefore, the global climate problem brought about by carbon dioxide has also been widely concerned by scientists from all over the world. CO 2 is the main component of greenhouse gases, but from a resource point of view, CO 2 At the same time, it is also a cheap, non-toxic, abundant, natural and renewable C1 resource that widely exists in nature. It can be used to prepare many basic chemical raw materials and various carbonates, carbamates, carboxylic acids, ureas and other important heterocyclic compounds; in additi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/61B01J31/02C07D317/36
CPCB01J31/0281B01J2231/341C07D233/61C07D317/36
Inventor 岳爽郝秀佳叶乔林李俊
Owner LIAONING UNIVERSITY
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