CN102887855B - Containing pyridine ion liquid, its preparation method and application - Google Patents
Containing pyridine ion liquid, its preparation method and application Download PDFInfo
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- CN102887855B CN102887855B CN201110200821.6A CN201110200821A CN102887855B CN 102887855 B CN102887855 B CN 102887855B CN 201110200821 A CN201110200821 A CN 201110200821A CN 102887855 B CN102887855 B CN 102887855B
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
Abstract
The present invention is applicable to chemical material technical field, provides a kind of containing pyridine ion liquid, its preparation method and application.Following structural formula should be had containing pyridine ion liquid.The present invention containing pyridine ion liquid, by introducing C-O ehter bond in positively charged ion, makes the performance of ionic liquid greatly strengthen, and on the one hand its fusing point is significantly reduced, promote on the other hand its in electrochemical applications with the complex ability of lithium ion.The present invention is containing pyridine ion liquid preparation method, simple to operate, with low cost, environmentally friendly, is very suitable for suitability for industrialized production.
Description
Technical field
The invention belongs to chemical material technical field, particularly relate to a kind of containing pyridine ion liquid, its preparation method and application.
Background technology
Ionic liquid (Ionic liquids) refers to that in room temperature range, (be generally less than 100 DEG C) is in a liquid state, and is made up of organic cation and inorganic anion (or organic anion).Compare with ionogen with traditional organic solvent, ionic liquid has a series of outstanding advantage: (1) fusing point lower than or close to room temperature, the temperature range be in a liquid state is wide; (2) steam force down, hardly volatilize, colourless, odorless; (3) there is larger equilibrium temperature scope, good chemical stability and wider electrochemical stability potential window; (4) good dissolution characteristics, all shows good dissolving power to a lot of inorganics and organism; (5) nonflammable without point of ignition; (6) can be recycled, free from environmental pollution etc.But at present, ionic liquid preparation method complicated operation, cost is high, and prepared ionic liquid fusing point is higher, which greatly limits the application of ionic liquid.
Summary of the invention
In view of this, the embodiment of the present invention provides a kind of and solves containing pyridine ion liquid the technical problem that existing ionic liquid fusing point is higher, and this ionic liquid preparation method and application.
The present invention is achieved in that
A kind of containing pyridine ion liquid, there is following structural formula:
The embodiment of the present invention provides a kind of containing pyridine ion liquid, has following structural formula (I):
Wherein, R is selected from methoxvethoxvmethvl; Y is selected from BF
4 -, PF
6 -, (CF
3sO
2)
2n
-, CF
3sO
3 -in one.
And,
A kind of containing pyridine ion liquid preparation method, comprise the steps:
Under anhydrous and oxygen-free condition, by pyridine and haloalkane 1: 1.05-1: 1.2 mixing in molar ratio, stirring reaction 48-72 hour under temperature is 60-80 DEG C of condition, washing obtains the alky pyridinium halides that structural formula (III) represents, wherein, this haloalkane is selected from methoxy ethoxy methyl chloride, methoxy ethoxy monobromethane or methoxy ethoxy methyl iodide a kind of, and structural formula (III) is:
The alky pyridinium halides that this structural formula (III) is represented and inorganic salt soluble in water, stirring reaction 8-24 hour, obtain containing pyridine ion liquid, wherein, in these inorganic salt, negatively charged ion is BF
4 -, PF
6 -, (CF
3sO
2)
2n
-or CF
3sO
3 -; R is methoxvethoxvmethvl; X is chlorine, bromine or iodine, and reaction formula is expressed as:
The embodiment of the present invention provides the application of above-mentioned ionic liquid in ultracapacitor or battery further.
The embodiment of the present invention containing pyridine ion liquid, by introducing C-O ehter bond in positively charged ion, makes the performance of ionic liquid greatly strengthen, and on the one hand its fusing point is significantly reduced, promote on the other hand its in electrochemical applications with the complex ability of lithium ion.The embodiment of the present invention is containing pyridine ion liquid preparation method, simple to operate, with low cost, environmentally friendly, is very suitable for suitability for industrialized production.
Accompanying drawing explanation
Fig. 1 is that the embodiment of the present invention contains pyridine ion liquid preparation method schema.
Embodiment
In order to make object of the present invention, technical scheme and advantage clearly understand, below in conjunction with drawings and Examples, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not intended to limit the present invention.
The embodiment of the present invention provides a kind of containing pyridine ion liquid, has following structural formula (I):
Wherein, R is methoxvethoxvmethvl; Y is selected from BF
4 -, PF
6 -, (CF
3sO
2)
2n
-, CF
3sO
3 -in one.
Particularly, the embodiment of the present invention is containing pyridine ion liquid, and comprise positively charged ion and negatively charged ion, this cationic structural formula (II) is:
wherein, R is that (molecular formula is C to methoxvethoxvmethvl
4h
9o
2); This negatively charged ion is selected from BF
4 -, PF
6 -, (CF
3sO
2)
2n
-, CF
3sO
3 -in one; The embodiment of the present invention containing pyridine ion liquid, by introducing C-O ehter bond in positively charged ion, makes the performance of ionic liquid greatly strengthen, and on the one hand its fusing point is significantly reduced, promote on the other hand its in electrochemical applications with the complex ability of lithium ion.
Refer to Fig. 1, Fig. 1 shows the schema of the embodiment of the present invention containing pyridine ion liquid preparation method, comprises the steps:
Step S01, prepares alky pyridinium halides
Under anhydrous and oxygen-free condition, by pyridine and haloalkane 1: 1.05-1: 1.2 mixing in molar ratio, stirring reaction 48-72 hour under temperature is 60-80 DEG C of condition, washing obtains the alky pyridinium halides that structural formula (III) represents, wherein, this haloalkane is selected from methoxy ethoxy methyl chloride, methoxy ethoxy monobromethane or methoxy ethoxy methyl iodide a kind of, and structural formula (III) is:
Step S02, preparation is containing pyridine ion liquid
The alky pyridinium halides that this structural formula (III) is represented and inorganic salt soluble in water, stirring reaction 8-24 hour, obtain containing pyridine ion liquid, wherein, in these inorganic salt, negatively charged ion is BF
4 -, PF
6 -, (CF
3sO
2)
2n
-or CF
3sO
3 -; R is methoxvethoxvmethvl; X is chlorine, bromine or iodine, and reaction formula is expressed as:
Particularly, in step S01, pyridine and haloalkane Reactive Synthesis alky pyridinium halides.Wherein, this oxygen free condition does not limit, and such as, operates under the protection of the rare gas elementes such as nitrogen, argon gas, helium; This haloalkane (RX) is selected from methoxy ethoxy methyl chloride, methoxy ethoxy monobromethane or methoxy ethoxy methyl iodide, and particularly, R is methoxvethoxvmethvl, and X is chlorine, bromine or iodine; The molar ratio of this pyridine and haloalkane is 1: 1.05-1.2, is preferably 1: 1.1; This step S01 temperature of reaction is 60-80 DEG C, is preferably 60-70 DEG C; Reaction times is 48-72 hour, is preferably 48-60 hour; The reaction of step S01 is carried out under agitation, and concrete alr mode does not limit.After having reacted, leave standstill cooling, reaction product ethyl acetate is washed more than 3 times, then completely dry in vacuum environment more than 80 DEG C, namely obtain yellow solid is the alky pyridinium halides that formula II I represents.This methoxy ethoxy methyl chloride structural formula is:
This methoxy ethoxy monobromethane structural formula is:
This step S01 reaction formula is expressed as:
Particularly, in step S02, by ion exchange reaction, change the halide-ions in alky pyridinium halides into desired anion, generate target product.Positively charged ion (M) in these inorganic salt (MY) is selected from Na
+, K
+or NH
4 +in one, negatively charged ion (Y) is selected from BF
4 -, PF
6 -, (CF
3sO
2)
2n
-or CF
3sO
3 -in one, the array mode of this positively charged ion and negatively charged ion does not limit, such as, NaBF
4, Na (CF
3sO
2)
2n, K PF
6, K CF
3sO
3, NH
4cF
3sO
3; This step S02 temperature of reaction is room temperature, does not specifically limit, such as 20 DEG C, and the reaction times is 8-24 hour, is preferably 8-16 hour; The alky pyridinium halides that this formula II I represents and inorganic salt mol ratio are 1: 1, and this reaction is also carried out under agitation, and concrete alr mode does not limit.After having reacted, reaction product carried out extract, strip, concentrated and dry, be specially, after product dichloromethane extraction will be reacted more than three times, combining extraction liquid, then strips with deionized water, until with saturated silver nitrate aqueous solution titration aqueous phase, till not precipitating generation, collect organic phase (methylene dichloride phase), will concentrate with Rotary Evaporators, then more than 80 DEG C in vacuum environment drying 48 hours, obtain colourless liquid, namely containing pyridine ion liquid.
The embodiment of the present invention is containing pyridine ion liquid preparation method, by preparing in alky pyridinium halides step, ehter bond (C-O) is introduced in alky pyridinium halides, make prepared greatly strengthening containing pyridine ion liquid performance, on the one hand its fusing point is significantly reduced, promote on the other hand its in electrochemical applications with the complex ability of lithium ion; The embodiment of the present invention is containing pyridine ion liquid preparation method, and productivity effect is high, can not produce the material of contaminate environment, and environmentally friendly, productivity effect is high, is very suitable for suitability for industrialized production.
The embodiment of the present invention provides above-mentioned containing the application of pyridine ion liquid in ultracapacitor or battery further.
Be described in detail containing pyridine ion liquid preparation method above-mentioned below in conjunction with specific embodiment.
In following embodiment one to seven, R is methoxvethoxvmethvl (i.e.-C
4h
9o
2), its structural formula is :-CH
2-O-CH
2-CH
2-O-CH
3.
Embodiment one
The embodiment of the present invention, containing pyridine ion liquid, has following structural formula:
The embodiment of the present invention, containing pyridine ion liquid preparation method, comprises the steps:
Step one, preparation chlorination 1-methoxvethoxvmethvl pyridine villaumite
At N
2(or Ar
2) atmosphere protection under, pyridine (79g, 1mol) and methoxy ethoxy methyl chloride (136.4g, 1.1mol) are added in reactor, temperature are adjusted to 60 DEG C, stirring reaction 48 hours; Leave standstill cooling, then reaction product ethyl acetate is washed three times, vacuum-drying at 80 DEG C, obtain lurid solid, productive rate is 85%;
Step 2, preparation 1-methoxvethoxvmethvl pyridinium tetrafluoroborate salt
Chlorination 1-methoxvethoxvmethvl pyridine (112.5g, 0.5mol), NaBF that step one is obtained
4(55g, 0.5mol), and 100mL deionized water is added in reactor, at room temperature stirs 8 hours, and will react solution 250mL dichloromethane extraction 3 times afterwards, combining extraction liquid, then uses the back extraction of 60mL deionized water repeatedly, until with saturated AgNO
3till aqueous solution titration aqueous phase produces without precipitation, collect methylene dichloride phase, this methylene dichloride Rotary Evaporators is concentrated, then carries out 80 DEG C of vacuum-dryings 48 hours, obtain colourless liquid, i.e. 1-methoxvethoxvmethvl pyridinium tetrafluoroborate salt (containing pyridine ion liquid).
1H MR(CDCl3，400MHz，ppm)：9.12(d，2H)，8.60(t，1H)，8.15(t，2H)，5.92(s，2H)，3.84(m，2H)，3.38(m，2H)，3.24(s，3H)。
Embodiment two
The embodiment of the present invention, containing pyridine ion liquid, has following structural formula:
The embodiment of the present invention, containing pyridine ion liquid preparation method, comprises the steps:
Step one, preparation bromination 1-methoxvethoxvmethvl pyridine
At N
2(or Ar
2) atmosphere protection under, pyridine (79g, 1mol) and methoxy ethoxy monobromethane (184.8g, 1.1mol) are added in reactor, temperature are adjusted to 70 DEG C, stirring reaction 60 hours; Leave standstill cooling, then reaction product ethyl acetate is washed three times, vacuum-drying at 80 DEG C, obtain lurid solid, productive rate is 86%;
Step 2, preparation 1-methoxvethoxvmethvl pyridinium tetrafluoroborate salt
Bromination 1-methoxvethoxvmethvl pyridine (0.5mol), NaBF that step one is obtained
4(55g, 0.5mol), and 120mL deionized water is added in reactor, at room temperature stirs 12 hours, and will react solution 250mL dichloromethane extraction 3 times afterwards, combining extraction liquid, then uses the back extraction of 60mL deionized water repeatedly, until with saturated AgNO
3till aqueous solution titration aqueous phase produces without precipitation, collect methylene dichloride phase, this methylene dichloride Rotary Evaporators is concentrated, then carries out 80 DEG C of vacuum-dryings 48 hours, obtain colourless liquid, namely prepare 1-methoxvethoxvmethvl pyridinium tetrafluoroborate salt (containing pyridine ion liquid).
Embodiment three
The embodiment of the present invention, containing pyridine ion liquid, has following structural formula:
The embodiment of the present invention, containing pyridine ion liquid preparation method, comprises the steps:
Step one, preparation chlorination 1-methoxvethoxvmethvl pyridine
At N
2(or Ar
2) atmosphere protection under, pyridine (79g, 1mol) and methoxy ethoxy methyl chloride (130.2g, 1.05mol) are added in reactor, temperature are adjusted to 80 DEG C, stirring reaction 72 hours; Leave standstill cooling, then reaction product ethyl acetate is washed three times, vacuum-drying at 80 DEG C, obtain lurid solid, productive rate is 84%;
Step 2, preparation 1-methoxvethoxvmethvl pyridine hexafluorophosphate
Chlorination 1-methoxvethoxvmethvl pyridine (112.5g, 0.5mol), KPF that step one is obtained
6(92g, 0.5mol), and 150mL deionized water is added in reactor, at room temperature stirs 24 hours, and will react solution 250mL dichloromethane extraction 3 times afterwards, combining extraction liquid, then uses the back extraction of 60mL deionized water repeatedly, until with saturated AgNO
3till aqueous solution titration aqueous phase produces without precipitation, collect methylene dichloride phase, this methylene dichloride Rotary Evaporators is concentrated, then carries out 80 DEG C of vacuum-dryings 48 hours, obtain colourless liquid, i.e. 1-methoxvethoxvmethvl pyridine hexafluorophosphate (containing pyridine ion liquid).
Embodiment four
The embodiment of the present invention, containing pyridine ion liquid, has following structural formula:
The embodiment of the present invention, containing pyridine ion liquid preparation method, comprises the steps:
Step one, preparation bromination 1-methoxvethoxvmethvl pyridine
At N
2(or Ar
2) atmosphere protection under, pyridine (79g, 1mol) and methoxy ethoxy monobromethane (176.4g, 1.05mol) are added in reactor, temperature are adjusted to 65 DEG C, stirring reaction 54 hours; Leave standstill cooling, then reaction product ethyl acetate is washed three times, vacuum-drying at 80 DEG C, obtains light yellow solid, and productive rate is 84%;
Step 2, preparation 1-methoxvethoxvmethvl pyridine hexafluorophosphate
Bromination 1-methoxvethoxvmethvl pyridine (0.5mol), KPF that step one is obtained
6(92g, 0.5mol), and 125mL deionized water is added in reactor, at room temperature stirs 16 hours, and will react solution 250mL dichloromethane extraction 3 times afterwards, combining extraction liquid, then uses the back extraction of 60mL deionized water repeatedly, until with saturated AgNO
3till aqueous solution titration aqueous phase produces without precipitation, collect methylene dichloride phase, this methylene dichloride Rotary Evaporators is concentrated, then carries out 80 DEG C of vacuum-dryings 48 hours, obtain colourless liquid, i.e. 1-methoxvethoxvmethvl pyridine hexafluorophosphate (containing pyridine ion liquid).
Embodiment five
The embodiment of the present invention, containing pyridine ion liquid, has following structural formula:
The embodiment of the present invention, containing pyridine ion liquid preparation method, comprises the steps:
Step one, preparation chlorination 1-methoxvethoxvmethvl pyridine
At N
2(or Ar
2) atmosphere protection under, pyridine (79g, 1mol) and methoxy ethoxy methyl chloride (148.8g, 1.2mol) are added in reactor, temperature are adjusted to 75 DEG C, stirring reaction 65 hours; Leave standstill cooling, then reaction product ethyl acetate is washed three times, vacuum-drying at 80 DEG C, obtain lurid solid, productive rate is 86%;
Step 2, preparation 1-methoxvethoxvmethvl pyridine fluoroform sulfimide salt
The chlorination 1-methoxvethoxvmethvl pyridine (112.5g that step one is obtained, 0.5mol), fluoroform sulfimide potassium TFSI-K (55g, 0.5mol), and 135mL deionized water is added in reactor, at room temperature stir 20 hours, solution 250mL dichloromethane extraction 3 times after reacting, combining extraction liquid, then the back extraction of 60mL deionized water is used repeatedly, until with saturated AgNO
3till aqueous solution titration aqueous phase produces without precipitation, collect methylene dichloride phase, this methylene dichloride Rotary Evaporators is concentrated, carry out 80 DEG C of vacuum-dryings 48 hours again, obtain colourless liquid, i.e. 1-methoxvethoxvmethvl pyridine fluoroform sulfimide salt (containing pyridine ion liquid).
Embodiment six
The embodiment of the present invention, containing pyridine ion liquid, has following structural formula:
The embodiment of the present invention, containing pyridine ion liquid preparation method, comprises the steps:
Step one, preparation bromination 1-methoxvethoxvmethvl pyridine
At N
2(or Ar
2) atmosphere protection under, pyridine (79g, 1mol) and methoxy ethoxy monobromethane (176.4g, 1.05mol) are added in reactor, temperature are adjusted to 78 DEG C, stirring reaction 68 hours; Leave standstill cooling, then reaction product ethyl acetate is washed three times, vacuum-drying at 80 DEG C, obtains light yellow solid, and productive rate is 84%;
Step 2, preparation 1-methoxvethoxvmethvl pyridine fluoroform sulphonate
Bromination 1-methoxvethoxvmethvl pyridine (0.5mol), CF that step one is obtained
3sO
3na (86g, 0.5mol), and 135mL deionized water is added in reactor, at room temperature stir 14 hours, solution 250mL dichloromethane extraction 3 times after reacting, combining extraction liquid, then the back extraction of 60mL deionized water is used repeatedly, until with saturated AgNO
3till aqueous solution titration aqueous phase produces without precipitation, collect methylene dichloride phase, this methylene dichloride Rotary Evaporators is concentrated, then carries out 80 DEG C of vacuum-dryings 48 hours, obtain colourless liquid, i.e. 1-methoxvethoxvmethvl pyridine fluoroform sulphonate (containing pyridine ion liquid).
Embodiment seven
The embodiment of the present invention, containing pyridine ion liquid, has following structural formula:
The embodiment of the present invention, containing pyridine ion liquid preparation method, comprises the steps:
Step one, preparation iodate 1-methoxvethoxvmethvl pyridine
At N
2(or Ar
2) atmosphere protection under, pyridine (79g, 1mol) and methoxy ethoxy methyl iodide (237.6g, 1.1mol) are added in reactor, temperature are adjusted to 70 DEG C, stirring reaction 68 hours; Leave standstill cooling, then reaction product ethyl acetate is washed three times, vacuum-drying at 80 DEG C, obtains light yellow solid, and productive rate is 87%;
Step 2, preparation 1-methoxvethoxvmethvl pyridine fluoroform sulphonate
Iodate 1-methoxvethoxvmethvl pyridine (0.5mol), CF that step one is obtained
3sO
3na (86g, 0.5mol), and 135mL deionized water is added in reactor, at room temperature stir 14 hours, solution 250mL dichloromethane extraction 3 times after reacting, combining extraction liquid, then the back extraction of 60mL deionized water is used repeatedly, until with saturated AgNO
3till aqueous solution titration aqueous phase produces without precipitation, collect methylene dichloride phase, this methylene dichloride Rotary Evaporators is concentrated, then carries out 80 DEG C of vacuum-dryings 48 hours, obtain colourless liquid, i.e. 1-methoxvethoxvmethvl pyridine fluoroform sulphonate (containing pyridine ion liquid).
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, all any amendments done within the spirit and principles in the present invention, equivalent replacement and improvement etc., all should be included within protection scope of the present invention.
Claims (3)
1., containing a pyridine ion liquid preparation method, comprise the steps:
Under anhydrous and oxygen-free condition, by pyridine and haloalkane 1:1.05-1:1.2 mixing in molar ratio, stirring reaction 48-72 hour under temperature is 60-80 DEG C of condition, washing obtains the alky pyridinium halides that structure formula III represents, wherein, described haloalkane is selected from methoxy ethoxy methyl chloride, methoxy ethoxy monobromethane or methoxy ethoxy methyl iodide a kind of, and structure formula III is:
The alky pyridinium halides that described structure formula III is represented and inorganic salt soluble in water, stirring reaction 8-24 hour, pass through ion exchange reaction, change the halide-ions in alky pyridinium halides into desired anion, obtain containing pyridine ion liquid, wherein, in described inorganic salt, negatively charged ion is BF
4 -, PF
6 -, (CF
3sO
2)
2n
-or CF
3sO
3 -; R is methoxvethoxvmethvl; X is chlorine, bromine or iodine, and reaction formula is expressed as:
wherein, the alky pyridinium halides that represents of described structure formula III and inorganic salt mol ratio are 1:1;
After the reactions steps of the alky pyridinium halides that described structure formula III represents and inorganic salt, also comprise solution after reaction carried out extract, strip, concentrated and dry.
2. as claimed in claim 1 containing pyridine ion liquid preparation method, it is characterized in that, the positively charged ion in described inorganic salt is Na
+, K
+or NH
4 +.
3. as claimed in claim 1 containing pyridine ion liquid preparation method, it is characterized in that, the reaction times of the alky pyridinium halides that described structure formula III represents and inorganic salt is 8-24 hour.
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|---|---|---|---|---|
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| US4886735A (en) * | 1987-05-21 | 1989-12-12 | Basf Aktiengesellschaft | Photopolymerizable recording materials and photoresist layers and lithographic printing plates based thereon |
| CN101765939A (en) * | 2007-07-23 | 2010-06-30 | 赢创德固赛有限责任公司 | Electrolyte preparations for energy stores based on ionic liquids |
| CN102015666A (en) * | 2008-04-29 | 2011-04-13 | 默克专利有限公司 | Reactive ionic liquids |
-
2011
- 2011-07-18 CN CN201110200821.6A patent/CN102887855B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2991285A (en) * | 1958-09-09 | 1961-07-04 | Rohm & Haas | Process of cyanation and nitriles produced thereby |
| US4886735A (en) * | 1987-05-21 | 1989-12-12 | Basf Aktiengesellschaft | Photopolymerizable recording materials and photoresist layers and lithographic printing plates based thereon |
| CN101765939A (en) * | 2007-07-23 | 2010-06-30 | 赢创德固赛有限责任公司 | Electrolyte preparations for energy stores based on ionic liquids |
| CN102015666A (en) * | 2008-04-29 | 2011-04-13 | 默克专利有限公司 | Reactive ionic liquids |
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| Title |
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