A kind of PEG-functionalized bis-imidazolium cation temperature-controlled ionic liquid and its preparation method and application

A technology of bisimidazolium cation and ionic liquid is applied in the field of temperature-controlled ionic liquid of bisimidazolium cation and its preparation, which can solve the problems of increasing impurities in ionic liquid, polychlorinated by-products, polluting the environment, etc., and achieves simple preparation process, chlorination Less by-products and less environmental pollution

Active Publication Date: 2016-08-31
HENAN NORMAL UNIV
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  • Abstract
  • Description
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Problems solved by technology

[0007] This synthesis process has the following disadvantages: in the first step of synthesis, thionyl chloride is added dropwise to the toluene solution of PEG-1000 and pyridine, which will generate more single-ended chlorinated by-products, and the reaction temperature of this synthesis step The temperature is 88°C, the temperature is high, the reaction time is 16h, the time is long, the follow-up treatment uses concentrated hydrochloric acid, pollutes the environment, and the yield is low, only 83%
[0011] This synthesis process has the following disadvantages: in the first step of synthesis, methanesulfonyl chloride is added dropwise to the toluene solution of PEG-1000 and triethylamine, which will generate more single-end substitution by-products; in the second step of synthesis, petroleum ether Extracting the ionic liquid phase will cause unreacted methanesulfonyl chloride, methanesulfonate and methylimidazole to dissolve in petroleum ether, increasing the impurities in the ionic liquid and increasing the difficulty of subsequent processing; the final product ionic liquid PEG-1000- DIL only forms a liquid-liquid mixed system with UCST phase behavior with toluene, and is completely miscible in alcohol and water

Method used

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  • A kind of PEG-functionalized bis-imidazolium cation temperature-controlled ionic liquid and its preparation method and application
  • A kind of PEG-functionalized bis-imidazolium cation temperature-controlled ionic liquid and its preparation method and application
  • A kind of PEG-functionalized bis-imidazolium cation temperature-controlled ionic liquid and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Dissolve 31mmol of compound 1 in 100mL of anhydrous toluene to form solution 1, dissolve 62mmol of thionyl chloride and 62mmol of pyridine in 150mL of anhydrous toluene to form solution 2, and add solution 1 to solution 2 dropwise under nitrogen protection reaction at 60° C. for 2 hours, and then suction-filtered, an appropriate amount of anhydrous potassium carbonate was added to the filtrate to neutralize the acidic substances, suction-filtered, and rotary evaporated to obtain compound 2 (yield 90%).

[0039] Cl-PEG400 -Cl. 1 HNMR (D 2 O, δ / ppm ): 3.62-3.67(m35.1H(OCH 2 CH 2 ) 8.8 ) .

[0040] Cl-PEG 600 -Cl. 1 HNMR (D 2 O, δ / ppm ):3.64-3.69(m49.2H,(OCH 2 CH 2 ) 12.3 ).

[0041] Cl-PEG 800 -Cl. 1 HNMR (D 2 O, δ / ppm ):3.65-3.76(m69.6H,(OCH 2 CH 2 ) 17.4 ).

[0042] Cl-PEG 1000 -Cl. 1 H-NMR ((D 2 O, δ / ppm): 3.66-3.79 (m88.4H, (OCH 2 CH 2 ) 22.1 ).

[0043] (2) Under nitrogen protection, 20 mmol of compound 2 and 40 mmol of compound 3 were r...

Embodiment 2

[0054] (1) Dissolve 31mmol of compound 1 in 100mL of anhydrous chloroform to form solution 1, dissolve 93mmol of thionyl chloride and 93mmol of potassium carbonate in 150mL of anhydrous chloroform to form solution 2, and add solution 1 dropwise to the solution under nitrogen protection 2, reacted at 70°C for 3 hours, then suction filtered, added an appropriate amount of anhydrous potassium carbonate to the filtrate to neutralize acidic substances, suction filtered, and rotary evaporated to obtain compound 2 (yield 90%).

[0055] Cl-PEG 400 -Cl. 1 HNMR (D 2 O, δ / ppm ): 3.62-3.67(m35.1H(OCH 2 CH 2 ) 8.8 ) .

[0056] Cl-PEG 600 -Cl. 1 HNMR (D 2 O, δ / ppm ):3.64-3.69(m49.2H,(OCH 2 CH 2 ) 12.3 ).

[0057] Cl-PEG 800 -Cl. 1 HNMR (D 2 O, δ / ppm ):3.65-3.76(m69.6H,(OCH 2 CH 2 ) 17.4 ).

[0058] Cl-PEG 1000 -Cl. 1 H-NMR ((D 2 O, δ / ppm): 3.66-3.79 (m88.4H, (OCH 2 CH 2 ) 22.1 ).

[0059] (2) Under nitrogen protection, 20 mmol of compound 2 and 60 mmol of compound...

Embodiment 3

[0070] (1) Dissolve 31mmol of compound 1 in 100mL of anhydrous n-hexane to form solution 1, dissolve 124mmol of thionyl chloride and 124mmol of potassium bicarbonate in 150mL of anhydrous n-hexane to form solution 2, and dissolve 1 drop of the solution under nitrogen protection Added to solution 2, reacted at 80°C for 4 hours, then filtered with suction, added an appropriate amount of anhydrous potassium carbonate to the filtrate to neutralize acidic substances, filtered with suction, and rotary evaporated to obtain compound 2 (yield 90%).

[0071] Cl-PEG 400 -Cl. 1 HNMR (D 2 O, δ / ppm ): 3.62-3.67(m35.1H(OCH 2 CH 2 ) 8.8 ) .

[0072] Cl-PEG 600 -Cl. 1 HNMR (D 2 O, δ / ppm ):3.64-3.69(m49.2H,(OCH 2 CH 2 ) 12.3 ).

[0073] Cl-PEG 800 -Cl. 1 HNMR (D 2 O, δ / ppm ):3.65-3.76(m69.6H,(OCH 2 CH 2 ) 17.4 ).

[0074] Cl-PEG 1000 -Cl. 1 H-NMR ((D 2 O, δ / ppm): 3.66-3.79 (m88.4H, (OCH 2 CH 2 ) 22.1 ).

[0075] (2) Under nitrogen protection, 20 mmol of compound 2 and...

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Abstract

The invention discloses PEG (polyethylene glycol) functionalized biimidazole cation temperature control ion liquid as well as a preparation method and application thereof. According to the key points of the technical scheme, the PEG functionalized biimidazole cation temperature control ion liquid has a structure described in the specification, and in the structure, n is 7, 11, 15 or 21. The invention further discloses a preparation method of the PEG functionalized biimidazole cation temperature control ion liquid and application of the PEG functionalized biimidazole cation temperature control ion liquid to extraction and separation of amino acid or protein. The PEG functionalized biimidazole cation temperature control ion liquid can form a two-liquid system with an LCST (lower critical solution temperature) phase behavior together with water, and can form a two-liquid system with a UCST (upper critical solution temperature) phase behavior together with an alcohol compound; a proper amount of water is added into the two-phase system of the ion liquid and alcohol so as to accurately adjust and control the two-phase system from the UCST phase behavior to the LCST phase behavior.

Description

technical field [0001] The invention belongs to the technical field of temperature-controlled ionic liquids, in particular to a class of PEG-functionalized bis-imidazolium cation temperature-controlled ionic liquids and a preparation method and application thereof. Background technique [0002] Liquid-liquid hybrid systems with reversible phase transitions have important applications in catalytic reactions, separation engineering, etc. Therefore, the development of new temperature-sensitive materials with reversible liquid-liquid phase transitions has been a long-term endeavor of the scientific community. In general, there are two types of liquid-liquid phase separation systems: systems with an upper critical solution temperature (UCST) and systems with a lower critical solution temperature (LCST). Generally, there are many liquid-liquid mixed systems with UCST phase behavior, but few systems with LCST phase behavior. [0003] At present, there are three main methods for sy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/60C07C311/48C07C303/40C08G65/48C07D209/20C07C227/40C07C229/36C07C229/22C07C229/08C12N9/50C12N9/36C07K14/765C07K1/14
CPCC07C227/40C07C303/40C07D209/20C07D233/60C07K14/765C08G65/48C08G2650/04C12N9/2462C12N9/63C12Y302/01017C12Y304/22002C07C311/48C07C229/36C07C229/22C07C229/08
Inventor 王键吉姚文惠陈永魁王慧勇李志勇崔国凯赵玉灵
Owner HENAN NORMAL UNIV
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