CN101492422A - Alkyl imidazole succinimide ionic liquid and method for preparing the same - Google Patents
Alkyl imidazole succinimide ionic liquid and method for preparing the same Download PDFInfo
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- CN101492422A CN101492422A CNA2009100471174A CN200910047117A CN101492422A CN 101492422 A CN101492422 A CN 101492422A CN A2009100471174 A CNA2009100471174 A CN A2009100471174A CN 200910047117 A CN200910047117 A CN 200910047117A CN 101492422 A CN101492422 A CN 101492422A
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- succimide
- ionic liquid
- methyl
- succinimide
- alkyl imidazole
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Abstract
The invention discloses alkyl imidazole succimide ion liquid and a preparation method thereof. The ion liquid is obtained by the steps as follows: 1-methyl-3-alkyl imidazole bromine is dripped into the aqueous solution of succimide silver salt to be stirred under room temperature to take double decomposition reaction and then is filtered, and filtrate is dried by rotary evaporation to obtain the ion liquid. The ion liquid has a structural formula shown as above. The ion liquid has certain alkalescence, has absorption capacity towards CO2 and is a good green solvent. The preparation method is simple and has low preparation cost.
Description
Technical field
The present invention relates to the chemical material preparing technical field, it is a kind of alkali ionic liquid and preparation method thereof, this method is to be raw material with succimide and 1-methyl-3-alkyl imidazole bromine, synthetic novel ion liquid by succimide negatively charged ion and 1-methyl-3-alkyl imidazole cation composition.
Technical background
Ionic liquid is meant in room temperature or near the compound that is made of ion fully that is in a liquid state under the room temperature.In recent ten years, ionic liquid becomes one of focus of Green Chemistry research, is called as the green solvent of 21 century.As everyone knows, the organic solvent that uses in traditional chemical technology engineering is because its volatility can cause very big pollution to environment.Therefore, ion liquid rise receives much attention, and its significant advantage has: liquid wide ranges, vapour pressure, soluble end is wide, electrochemical window is big, chemical property can adjusting and good electrical conductivity and thermal conductivity, good light transmittance and refractive index.Be mainly used at present: catalysis and organic synthesis field, compartment analysis field, electrochemical field, field of nanometer material technology and life science etc.Wherein forming ion liquid positively charged ion mainly comprises: quaternary ammonium alkyl positively charged ion, alkyl quaternary phosphonium cations, N-alkyl pyrroles positively charged ion, N-alkyl pyridine positively charged ion and dialkylimidazolium positively charged ion etc.Negatively charged ion mainly comprises Al
2Cl
7 -, BF
4 -, PF
6 -, SbF
6 -, CF
3SO
3 -, (CF
3SO
3)
2N
-, NO
3 -, CF
3CO
2 -, CH
3CO
2 -Deng.
Summary of the invention
The purpose of this invention is to provide a kind of alkyl imidazole succinimide ionic liquid and preparation method thereof, its ionic liquid has certain alkalescence, to CO
2Having adsorptive power, is a kind of good green solvent; Its preparation method is simple, and preparation cost is low.
The object of the present invention is achieved like this:
A kind of alkyl imidazole succinimide ionic liquid, its structural formula:
Wherein: R represents C
2-C
10Alkyl, comprise C
2H
5, C
4H
9, C
5H
11, C
6H
13, C
8H
17, C
10H
21
Above-mentioned preparation method of ionic liquid is: 1-methyl-3-alkyl imidazole bromine salt is added drop-wise in the aqueous solution of succimide silver salt, stirs under the room temperature, replacement(metathesis)reaction takes place, filter then, filtrate is revolved the dry succimide salt type ionic liquid that obtains of evaporate to dryness; Specifically may further comprise the steps:
The first step: the silver salt of preparation succimide
The succimide and the Silver Nitrate of mol ratio such as get, be dissolved in 50% the aqueous ethanolic solution, be heated to backflow, dropwise splash into mole such as succimide and concentration be the NaOH aqueous solution of 5mol/L, cool off under the room temperature, and washing, the lucifuge suction filtration obtains the silver salt of succimide to dry.
Second step: ion liquid preparation
The silver salt of succimide is dispersed in the water, the aqueous solution of the 1-methyl of mol ratios such as dropping-3-alkyl imidazole bromine salt, and lucifuge stirs, reacted 9-11 hour, and removed yellow mercury oxide, get filtrate, revolve steaming and dewater, vacuum-drying obtains alkyl imidazole succinimide ionic liquid.
Alkyl imidazole succinimide ionic liquid provided by the invention mainly contains 1-methyl-3-ethyl imidazol(e) succinimide ionic liquid, 1-methyl-3-butyl imidazole succinimide ionic liquid, 1-methyl-3-amyl group imidazoles succinimide ionic liquid, 1-methyl-3-hexyl imidazoles succinimide ionic liquid, 1-methyl-3-octyl group imidazoles succinimide ionic liquid, 1-methyl-3-decyl imidazoles succinimide ionic liquid.
The present invention compared with prior art has:
(1), the present invention has developed ion liquid new variety.
(2), ionic liquid of the present invention has certain alkalescence.
(3), the present invention can prepare the ionic liquid of different structure and function.
(4), as solvent, the reaction conditions gentleness has reduced production cost, and environmental pollution is few with water and ethanol in the present invention.In addition, the present invention is mainly replacement(metathesis)reaction, and the equipment of using is few, and is simple to operate.
(5), ionic liquid of the present invention has certain adsorption effect to carbonic acid gas (maximal absorptive capacity is 0.2051mol CO
2/ 1molIL).
Specific embodiments
Embodiment 1
The preparation of 1-methyl-3-ethyl imidazol(e) succinimide ionic liquid
The first step: get succimide 2.97g (0.03mol) and Silver Nitrate 5.10g (0.03mol), be dissolved in 50% the aqueous ethanolic solution,, dropwise splash into the NaOH aqueous solution 6ml of 5mol/L with constant pressure funnel 80-90 ℃ of reflux, there is precipitation slowly to separate out, after question response is complete, room temperature cooling, suction filtration, successively with 50% ethanol and ether washing, lucifuge suction filtration, and vacuum-drying get the succimide silver salt.
Second step: take by weighing 6.18g (0.03mol) succinimide silver and 5.73g (0.03mol) 1-methyl-3-ethyl imidazol(e) bromine salt, the succimide silver salt is stirred half an hour in 30ml distilled water, dropwise drip the aqueous solution of 1-methyl-3-ethyl imidazol(e) bromine salt, lucifuge stirs, and reacts about 10 hours, removes yellow mercury oxide, get filtrate, revolve steaming and dewater, vacuum-drying obtains 1-methyl-3-ethyl imidazol(e) succinimide ionic liquid.
Above-mentioned ion liquid characterization data is as follows:
1H NMR (DMSO, 500HZ) δ: 1.40 (t, 3H, CCH
3), 2.02 (t, 2H, CCH
2C), 2.14 (t, 2H, CCH
2C), 3.86 (s, 3H, NCH
3), 4.20 (t, 2H, CCH
2C), 7.74 (s, 1H, CCHN), 7.78 (s, 1H, NCHC), 9.69 (s, 1H, NCHN); IR (KBr): 3154,3088,2961,2930,2859,1678,1576,1463,1295,1173,867,730,628cm
-1
Embodiment 2
The preparation of 1-methyl-3-butyl imidazole succinimide ionic liquid
The first step: with embodiment 1.
Second step: take by weighing 6.18g (0.03mol) succimide silver salt and 6.57g (0.03mol) 1-methyl-3-imidazole-butyl bromide salt, the succimide silver salt is stirred half an hour in 30ml distilled water, dropwise drip the aqueous solution of 1-methyl-3-imidazole-butyl bromide salt, stir, reacted 11 hours, remove yellow mercury oxide, get filtrate, revolve steaming and dewater, vacuum-drying obtains 1-methyl-sub-liquid of 3-butyl imidazole succinyl ion.
Above-mentioned ion liquid characterization data is as follows:
1H NMR (DMSO, 500HZ) δ: 0.87 (t, 3H, CCH
3), 1.27 (t, 2H, CCH
2C), 1.80 (t, 2H, CCH
2C), 2.01 (t, 2H, CCH
2C), 2.14 (t, 2H, CCH
2C), 3.84 (s, 3H, NCH
3), 4.11 (t, 2H, NCH
2), 7.73 (s, 1H, CCHN), 7.82 (s, 1H, NCHC), 9.65 (s, 1H, NCHN); IR (KBr): 3398,3149,3082,2965,2935,2874,1667,1575,1458,1402,1300,1173,873,760,623cm
-1
Embodiment 3
The preparation of 1-methyl-3-amyl group imidazoles succinimide ionic liquid
The first step: with embodiment 1.
Second step: take by weighing 6.18g (0.03mol) succimide silver salt and 6.99g (0.03mol) 1-methyl-3-amyl group imidazoles bromine salt, the succimide silver salt is stirred half an hour in 30ml distilled water, dropwise drip the aqueous solution of 1-methyl-3-amyl group imidazoles bromine salt, stir, reacted about 10 hours, remove yellow mercury oxide, get filtrate, revolve steaming and dewater, vacuum-drying obtains 1-methyl-3-amyl group imidazoles succinimide ionic liquid.
Above-mentioned ion liquid characterization data is as follows:
1H NMR (DMSO, 500HZ) δ: 0.86 (t, 3H, CCH
3), 1.23 (t, 2H, CCH
2C), 1.24 (t, 2H, CCH
2C), 1.79 (t, 2H, CCH
2C), 2.01 (t, 2H, CCH
2C), 2.14 (t, 2H, CCH
2C), 3.85 (s, 3H, NCH
3), 4.15 (t, 2H, NCH
2), 7.73 (s, 1H, CCHN), 7.82 (s, 1H, NCHC), 9.60 (s, 1H, NCHN); IR (KBr): 3398,3149,3079,2963,2933,2870,1667,1578,1463,1402,1290,1173,875,768,623cm
-1
Embodiment 4
The preparation of 1-methyl-3-hexyl imidazoles succinimide ionic liquid
The first step: with embodiment 1.
Second step: take by weighing 6.18g (0.03mol) succimide silver salt and 7.41g (0.03mol) 1-methyl-3-hexyl imidazoles bromine salt, the succimide silver salt is stirred half an hour in 30ml distilled water, dropwise drip the aqueous solution of 1-methyl-3-hexyl imidazoles bromine salt, stir, reacted about 10 hours, remove yellow mercury oxide, get filtrate, revolve steaming and dewater, vacuum-drying obtains 1-methyl-3-hexyl imidazoles succinimide ionic liquid.
Described ion liquid characterization data is as follows:
1H NMR (DMSO, 500HZ) δ: 0.85 (t, 3H, CCH
3), 1.24 (t, 2H, CCH
2C), 1.24 (t, 2H, CCH
2C), 1.24 (t, 2H, CCH
2C), 1.77 (t, 2H, CCH
2C), 2.01 (t, 2H, CCH
2C), 2.14 (t, 2H, CCH
2C), 3.86 (s, 3H, NCH
3), 4.17 (t, 2H, NCH
2), 7.74 (s, 1H, CCHN), 7.80 (s, 1H, NCHC), 9.57 (s, 1H, NCHN); IR:3398,3149,3072,2960,2930,2863,1667,1580,1463,1417,1280,1168,877,776,623cm
-1
Embodiment 5
The preparation of 1-methyl-3-octyl group imidazoles succinimide ionic liquid
The first step: with embodiment 1.
Second step: take by weighing 6.18g (0.03mol) succimide silver salt and 8.25g (0.03mol) 1-methyl-3-octyl group imidazoles bromine salt, the succimide silver salt is stirred half an hour in 30ml distilled water, dropwise drip the aqueous solution of 1-methyl-3-octyl group imidazoles bromine salt, stir, reacted about 10 hours.Remove yellow mercury oxide, get filtrate, revolve steaming and dewater, vacuum-drying obtains 1-methyl-3-octyl group imidazoles succinimide ionic liquid.
Above-mentioned ion liquid characterization data is as follows:
1H NMR (DMSO, 500HZ) δ: 0.85 (t, 3H, CCH
3), 1.24 (m, 10H, C (CH
2)
2C), 1.77 (t, 2H, CCH
2C), 2.01 (t, 2H, CCH
2C), 2.14 (t, 2H, CCH
2C), 3.88 (s, 3H, NCH
3), 4.12 (t, 2H, NCH
2), 7.80 (s, 1H, CCHN), 7.82 (s, 1H, NCHC), 9.59 (s, 1H, NCHN); IR:3398,3160,3075,2967,2940,2868,1670,1585,1460,1420,1279,1168,877,766,623cm
-1
Embodiment 6
The preparation of 1-methyl-3-decyl imidazoles succinimide ionic liquid
The first step: with embodiment 1.
Second step: take by weighing 6.18g (0.03mol) succimide silver salt and 9.09g (0.03mol) 1-methyl-3-decyl imidazoles bromine salt, the succimide silver salt is stirred half an hour in 30ml distilled water, dropwise drip the aqueous solution of 1-methyl-3-decyl imidazoles bromine salt, stir, reacted 9 hours, remove yellow mercury oxide, get filtrate, revolve steaming and dewater, vacuum-drying obtains 1-methyl-3-decyl imidazoles succinimide ionic liquid.
Above-mentioned ion liquid characterization data is as follows:
1H NMR (DMSO, 500HZ) δ: 0.87 (t, 3H, CCH
3), 1.25 (m, 14H, C (CH
2)
7C), 1.75 (t, 2H, CCH
2C), 2.01 (t, 2H, CCH
2C), 2.13 (t, 2H, CCH
2C), 3.84 (s, 3H, NCH
3), 4.11 (t, 2H, NCH
2), 7.77 (s, 1H, CCHN), 7.80 (s, 1H, NCHC), 9.56 (s, 1H, NCHN); IR:3400,3160,3075,2970,2940,2871,1673,1591,1463,1420,1280,1168,870,769,625cm
-1
Claims (2)
1, a kind of alkyl imidazole succinimide ionic liquid, this ionic liquid are that 1-methyl-3-alkyl imidazole bromine salt is added drop-wise in the aqueous solution of succimide silver salt, stir under the room temperature, and replacement(metathesis)reaction takes place, and filter then, filtrate are revolved evaporate to dryness is dry to be obtained; Have following structural formula:
Wherein: R represents C
2-C
10Alkyl, comprise C
2H
5, C
4H
9, C
5H
11, C
6H
13, C
8H
17, C
10H
21
2, the described preparation method of ionic liquid of a kind of claim 1 specifically may further comprise the steps:
The first step: the silver salt of preparation succimide
The succimide and the Silver Nitrate of mol ratio such as get, be dissolved in 50% the aqueous ethanolic solution, be heated to backflow, dropwise splash into mole such as succimide and concentration be the NaOH aqueous solution of 5mol/L, cool off under the room temperature, and washing, the lucifuge suction filtration obtains the silver salt of succimide to dry;
Second step: ion liquid preparation
The silver salt of succimide is dispersed in the water, the aqueous solution of the 1-methyl of mol ratios such as dropping-3-alkyl imidazole bromine salt, and lucifuge stirs, reacted 9-11 hour, and removed yellow mercury oxide, get filtrate, revolve steaming and dewater, vacuum-drying obtains alkyl imidazole succinimide ionic liquid.
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|---|---|---|---|
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|---|---|---|---|
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103833622A (en) * | 2012-11-26 | 2014-06-04 | 海洋王照明科技股份有限公司 | Maleimide ionic liquid, and preparation method and application thereof |
| CN114082442A (en) * | 2021-11-18 | 2022-02-25 | 河南大学 | Succinimidyl ionic liquid and method for catalytically synthesizing quinazoline-2, 4(1H,3H) -diketone by using same |
-
2009
- 2009-03-06 CN CN2009100471174A patent/CN101492422B/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103833622A (en) * | 2012-11-26 | 2014-06-04 | 海洋王照明科技股份有限公司 | Maleimide ionic liquid, and preparation method and application thereof |
| CN103833622B (en) * | 2012-11-26 | 2016-04-20 | 海洋王照明科技股份有限公司 | Maleimide ionic liquid and its preparation method and application |
| CN114082442A (en) * | 2021-11-18 | 2022-02-25 | 河南大学 | Succinimidyl ionic liquid and method for catalytically synthesizing quinazoline-2, 4(1H,3H) -diketone by using same |
| CN114082442B (en) * | 2021-11-18 | 2024-01-19 | 河南大学 | Succinimidyl ionic liquid and method for synthesizing quinazoline-2, 4 (1H, 3H) -diketone by using same as catalyst |
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|---|---|
| CN101492422B (en) | 2010-12-01 |
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Granted publication date: 20101201 Termination date: 20130306 |