CN101210000A - Ionic liquid with high electrochemical stability and preparing method thereof - Google Patents
Ionic liquid with high electrochemical stability and preparing method thereof Download PDFInfo
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Abstract
The invention discloses a functional ionic liquid that has high electrochemical stability and a preparation method thereof. Positive ion of the ionic liquid is selected from nitrile-functionalized quaternary ammonium positive ion and negative ion thereof from one of chlorine, bromine, iodine, fluoborate, fluorophosphates, sulfate radical, nitrate radical, trifluoroacetic radical, trifluorochloromethane sulfonic acid group, bi (perfluoroalkyl group sulfonyl) imino negative ion, dinitrile amic radical and saccharin acid radical. Nitrile functional ionic liquid, the negative ion of which is halogen negative ion, is firstly prepared through reaction of pentagons or hexatomic tertiary amine with the alkyl halide that has nitrile functional groups, then ionic liquid that contains different negative ions is prepared by exchange of the negative ions. The ionic liquid has very low melting temperature, can bear the high temperature of 150 DEG C and be stable to water, hardly has vapor pressure but has good electrochemical stability, thereby the invention can be taken as solvent, catalyst ligand, electrochemical electrolyte, etc. that are applied in the fields of organic synthesis, catalytic reaction and lithium-ion battery, etc.
Description
Technical field
The present invention relates to a kind of functionalized ion liquid and preparation method thereof, belong to new chemical material and preparing technical field thereof with high electrochemical stability.
Background technology
Ionic liquid generally refers to by the relatively large organic cation of volume relative with volume less inorganic or organic anion constitutes in room temperature or be bordering on the material that is in a liquid state under the room temperature, and normally, they are also referred to as ionic liquid at room temperature.Compare with traditional molecule-type medium, ionic liquid has many distinct physicochemical properties, as low melting point, wide liquid journey, no vapour pressure, high conductivity, wide electrochemical window, designability etc.The not available peculiar property of these other traditional sucroses makes ionic liquid become and has " solid " liquid of liquid and solid dual-use function and characteristic concurrently, thereby demonstrated great potential and application prospect in the greenization process of current chemical.
Research the earliest can be traced back to the initial stage of eighties of last century about ionic liquid, and for example fusing point just once was in the news in 1914 at 12 ℃ nitric acid ethylamine ionic liquid.United States Patent (USP) had been reported aluminum chloride and the ethyl-magnesium-halide pyridine ion liquid that is mainly used in field of electroplating in 1948, can be referred to as first-generation ionic liquid at room temperature.This type of ionic liquid has a shortcoming, meets the water capacity exactly and easily decomposes rotten.To the sixties, the relevant researchist of United States Air Force research institute (U.S.Air Force Academy) has synthesized that a class fusing point is lower, the better chlorine aluminic acid of electrochemical stability dialkylimidazolium class ionic liquid.Because dialkylimidazolium positive ion structure and chemical property are particularly suitable as ion liquid positive ion, so dialkylimidazolium class ionic liquid is a class positive ion that is studied the most extensively, gos deep into and still be studied up to now and use.To the beginning of the nineties, United States Air Force research institute improves above-mentioned ionic liquid, a series of ionic liquids have been synthesized to water, air-stable, be dialkylimidazolium class Tetrafluoroboric acid, phosphofluoric acid, trifluoromethane sulfonic acid, tartrate, acetic acid plasma liquid, such ion liquid appearance also begins to cause the interest of large quantities of chemists.After this type of ionic liquid successfully is used as catalyzer and organic synthesis medium, ion liquid research has expanded to fields such as compartment analysis, clean energy, life science and functional materials fast and successfully over nearly two, three years, becomes one of focus in natural science and the technical study field.
Ionic liquid has a wide range of applications in electrochemistry, and at the beginning of the ionic liquid researchdevelopment with the main purpose that is applied as in electrochemistry.Nineteen fifty-one Hurley etc. has realized electrochemical deposition of metal aluminium first in ionic liquid after, the research of ionic liquid in electrochemistry is just carried out rapidly, especially after the Phosphorus dialkylimidazolium ionic liquid of the nineties fluorine boron fluorine in last century was found, this process had obtained great quickening.Why ionic liquid gains great popularity in electrochemical research, and be because ionic liquid has the incomparable physicochemical property of conventional solvent: the electrochemical window that (1) has broad is enough to carry out non-noble metal electrochemical deposition; (2) have quite high specific conductivity and mobility of ions; (3) temperature range in broadness is in a liquid state; (4) organic and inorganic and organometallic compound had good dissolving ability; (5) have the pure ionic environment that is different from solution, can obtain the result that in conventional ion solution, can not obtain.In recent years, people have carried out considerable research in electrochemical deposition and " tradition " field such as electrochemistry organic synthesis in ionic liquid, have obtained many achievements in research that important value is arranged.Yet (electrochemical window＜4V) has become and has hindered the major obstacle that ionic liquid is further used in electrochemical field the electrochemical stability that ionic liquid itself is lower.If by the combination of different zwitterion, the synthetic class of design has high electrochemical stability, and (ionic liquid at room temperature of electrochemical window＞5V) will have very big application potential in electrochemical field undoubtedly.
Summary of the invention
The object of the present invention is to provide a kind of functionalized ion liquid and preparation method thereof with high electrochemical stability.
A kind of ionic liquid with high electrochemical stability; it is characterized in that the ionic liquid cationic moiety is selected from the quaternary ammonium cation of itrile group functionalization, anionicsite is selected from chlorine, bromine; iodine; the fluoroboric acid root, hexafluorophosphoric acid root, sulfate radical; nitrate radical; the trifluoracetic acid root, trifluoromethayl sulfonic acid root, a kind of in two (perfluoroalkyl group sulfonyl) imido grpup negative ion, dintrile amine root and the asccharin acid group.
The structural formula of quaternary ammonium cation is:
Wherein, n is the integer of 0-15, and X is O, and C, a kind of among the N, R are a kind of in methyl, ethyl, propyl group, butyl, sec.-propyl or the isobutyl-.
Ionic liquid disclosed by the invention specifically has:
N-methyl-N-butyronitrile base tetramethyleneimine villaumite
Two (perfluoroalkyl group sulfonyl) inferior amine salts of N-methyl-N-butyronitrile base tetramethyleneimine
N-methyl-N-butyronitrile base tetramethyleneimine a tetrafluoro borate
N-methyl-N-acetonitrile-base morphine quinoline villaumite
Two (perfluoroalkyl group sulfonyl) inferior amine salts of N-methyl-N-acetonitrile-base morphine quinoline
N-methyl-N-acetonitrile-base morphine quinoline hexafluorophosphate
N-methyl-N-butyronitrile base morphine quinoline villaumite
Two (perfluoroalkyl group sulfonyl) inferior amine salts of N-methyl-N-butyronitrile base morphine quinoline
N-methyl-N-butyronitrile phenylpiperidines villaumite
Two (perfluoroalkyl group sulfonyl) inferior amine salts of N-methyl-N-butyronitrile phenylpiperidines
We have very low melt temperature by disclosed ionic liquid, anti-150 ℃ of high temperature, stable to water, almost there is not vapour pressure, has good electrochemical stability, therefore might be as solvent, catalyst ligand, electrochemical electrolysis matter etc. in organic synthesis, fields such as catalyzed reaction, lithium ion battery are applied.
Ionic liquid is by the tertiary amine and the haloalkane reaction that contains itrile group functionalization group of five-ring or six-ring, at first generating negatively charged ion is the itrile group functionalized ion liquid of halogen anion, obtains containing the ionic liquid of different anions then by anionresin.
Certainly, the introducing of itrile group will make ion liquid electrochemical stability great changes will take place.For example, the electrochemical window of two (perfluoroalkyl group sulfonyl) inferior amine salts of trimethylammonium butyl ammonium is 4.8V, and after introducing itrile group, the electrochemical window of two (perfluoroalkyl group sulfonyl) inferior amine salts of trimethylammonium butyronitrile base ammonium is up to 5.8V.
According to anionic difference, ionic liquid of the present invention can be divided into two classes: halogen and other classes.
The halogen preparation method of ionic liquid is as follows:
With excessive exsiccant R
1(X represents halogen to X, R
1Representative contains the hydrocarbon of itrile group), with exsiccant five-ring or six-ring tertiary amine in molar ratio 1.1: 1-1.9: 1 mixes mutually, keep 10-100 ℃, allow it react several hours to tens hours, vacuumize then, slough volatile composition, just obtain the ionic liquid that purity can satisfy general application requiring.
The active degree of concrete hybrid mode and temperature of reaction visual response thing and deciding.For example,,, can once all add reactant, be heated to 60-100 ℃ then, back flow reaction because reaction is slow for chloride reactant; And for reactant brominated, iodine, because the reaction ratio is very fast, should be with R
1X dropwise joins in the tertiary amine solution, at room temperature or under the ice-water bath condition reacts.
Making on the ion liquid basis of halogen, can make the ionic liquid of other type by the reaction of second step.The ionic liquid preparation method who for example contains tetrafluoroborate, nitrate radical is as follows:
Under the room temperature, equimolar halogen ionic liquid and sodium tetrafluoroborate or SODIUMNITRATE are dissolved in ethanol, allowed halide-ions all generate precipitation in mechanical stirring 24-48 hour, through ageing, after the filtration treatment,, promptly obtain containing required anion ion liquid with the filtrate evaporate to dryness.
The ionic liquid preparation method who contains hexafluoro-phosphate radical, two (trifluoromethane sulphonyl) imines acid group is as follows:
Under the room temperature, equimolar halogen ionic liquid and ammonium hexafluorophosphate or two (trifluoromethane sulphonyl) imido grpup lithium is soluble in water, under 0-10 ℃ lesser temps stirring reaction 2-24 hour,, therefore be easy to separate and purify because target product is water insoluble.
Functionalized ion liquid with high electrochemical stability of the present invention is stablized water and air, compares with present widely used imidazoles ionic liquid at room temperature, and following characteristics are arranged:
1, has higher refractive index, can be used as novel photoelectric material and be applied in the photoelectricity field;
2, have wideer electrochemical window, can be used as novel liquid dielectric and be used for electrochemical research;
3, generate transition metal complex catalyst with the transition metal ion complexing according to demand, can be used as novel green solvent and be applied in the compartment analysis.
Embodiment
In order to further specify details of the present invention, enumerate some embodiment below, but should not be so limited.
Embodiment 1
Synthesizing of N-methyl-N-butyronitrile base tetramethyleneimine villaumite
Taking by weighing N-crassitude 21.30g (0.25mol) is dissolved in the 50ml dehydrated alcohol, after stirring makes it thorough mixing under the room temperature, 31.1g chlorobutyronitrile (0.30mol) is added in the above-mentioned solution, under stirring, continue 70 ℃ of lower magnetic forces reaction 48h, rotary evaporation is removed etoh solvent and other volatile component, add the 40ml re-crystallizing in ethyl acetate, the gained white solid is washed respectively three times with anhydrous diethyl ether, suction filtration, solid was vacuumized under 100 ℃ 8 hours, get ionic liquid N-methyl-N-butyronitrile base tetramethyleneimine villaumite, productive rate is 88.4%.
Embodiment 2
Synthesizing of two (perfluoroalkyl group sulfonyl) inferior amine salts of N-methyl-N-butyronitrile base tetramethyleneimine
Taking by weighing N-methyl-N-butyronitrile base tetramethyleneimine villaumite 18.9g (0.1mol) is dissolved in the 50ml distilled water; add two (perfluoroalkyl group sulfonyl) imido grpup lithium salts 43.0g (0.15mol) under the stirring at room; react after 4 hours, leave standstill layering; tell lower floor's oil phase with separating funnel; behind distilled water wash 3 times, under 100 ℃, vacuumized 4 hours, get two (perfluoroalkyl group sulfonyl) inferior amine salts of colourless liquid N-methyl-N-butyronitrile base tetramethyleneimine; productive rate is 78.2%, and electrochemical window is 5.4V.
Embodiment 3
Synthesizing of N-methyl-N-butyronitrile base tetramethyleneimine a tetrafluoro borate
Taking by weighing N-methyl-N-butyronitrile base tetramethyleneimine villaumite 18.9g (0.1mol) is dissolved in the 50ml dehydrated alcohol, add sodium tetrafluoroborate 16.5g (0.15mol) under the stirring at room, continue stirring reaction after 48 hours, through ageing, after filtration waits and handles,, get white solid N-methyl-N-butyronitrile base tetramethyleneimine a tetrafluoro borate with the filtrate evaporate to dryness, productive rate is 86.1%, and electrochemical window is 5.3V.
Embodiment 4
Synthesizing of N-methyl-N-acetonitrile-base morphine quinoline villaumite
Taking by weighing N-methylmorpholine 25.3g (0.25mol) is dissolved in the 50ml dehydrated alcohol, after stirring makes it thorough mixing under the room temperature, 22.7g chloromethyl cyanide (0.30mol) is added in the above-mentioned solution, under stirring, continue 50 ℃ of lower magnetic forces reaction 48h, rotary evaporation is removed etoh solvent and other volatile component, add the 40ml re-crystallizing in ethyl acetate, the gained white solid is washed respectively three times with anhydrous diethyl ether, suction filtration, solid was vacuumized under 100 ℃ 8 hours, get ionic liquid N-methyl-N-acetonitrile-base morphine quinoline villaumite, productive rate is 82.5%.
Embodiment 5
Synthesizing of two (perfluoroalkyl group sulfonyl) inferior amine salts of N-methyl-N-acetonitrile-base morphine quinoline
Taking by weighing N-methyl-N-acetonitrile-base morphine quinoline villaumite 17.7g (0.1mol) is dissolved in the 50ml distilled water; add two (perfluoroalkyl group sulfonyl) imido grpup lithium salts 43.0g (0.15mol) under the stirring at room; react after 4 hours, leave standstill layering; tell lower floor's oil phase with separating funnel; behind distilled water wash 3 times, under 100 ℃, vacuumized 4 hours, get two (perfluoroalkyl group sulfonyl) inferior amine salts of colourless liquid N-methyl-N-acetonitrile-base morphine quinoline; productive rate is 76.4%, and electrochemical window is 5.5V.
Embodiment 6
Synthesizing of N-methyl-N-acetonitrile-base morphine quinoline hexafluorophosphate
Taking by weighing N-methyl-N-acetonitrile-base morphine quinoline villaumite 17.7g (0.1mol) is dissolved in the 50ml distilled water, add ammonium hexafluorophosphate 24.5g (0.15mol) under the stirring at room, react after 4 hours, leave standstill layering, tell lower floor's oil phase with separating funnel, behind distilled water wash 3 times, under 100 ℃, vacuumized 4 hours, get white solid N-methyl-N-acetonitrile-base morphine quinoline hexafluorophosphate, productive rate is 85.4%, and electrochemical window is 5.3V.
Embodiment 7
Synthesizing of N-methyl-N-butyronitrile base morphine quinoline villaumite
Taking by weighing N-methylmorpholine 25.3g (0.25mol) is dissolved in the 50ml dehydrated alcohol, after stirring makes it thorough mixing under the room temperature, 31.1g chlorobutyronitrile (0.30mol) is added in the above-mentioned solution, under stirring, continue 50 ℃ of lower magnetic forces reaction 48h, rotary evaporation is removed etoh solvent and other volatile component, add the 40ml re-crystallizing in ethyl acetate, the gained white solid is washed respectively three times with anhydrous diethyl ether, suction filtration, solid was vacuumized under 100 ℃ 8 hours, get ionic liquid N-methyl-N-butyronitrile base morphine quinoline villaumite, productive rate is 82.5%.
Embodiment 8
Synthesizing of two (perfluoroalkyl group sulfonyl) inferior amine salts of N-methyl-N-butyronitrile base morphine quinoline
Taking by weighing N-methyl-N-butyronitrile base morphine quinoline villaumite 20.5g (0.1mol) is dissolved in the 50ml distilled water; add two (perfluoroalkyl group sulfonyl) imido grpup lithium salts 43.0g (0.15mol) under the stirring at room; react after 4 hours, leave standstill layering; tell lower floor's oil phase with separating funnel; behind distilled water wash 3 times, under 100 ℃, vacuumized 4 hours, get two (perfluoroalkyl group sulfonyl) inferior amine salts of colourless liquid N-methyl-N-butyronitrile base morphine quinoline; productive rate is 79.2%, and electrochemical window is 5.3V.
Embodiment 9
Synthesizing of N-methyl-N-butyronitrile phenylpiperidines villaumite
With embodiment 1, but replace 21.30g (0.25mol) N-crassitude with 24.8g (0.25mol) N-methyl piperidine, all the other conditions are constant.Reaction obtains white solid after finishing, and is product N-methyl-N-butyronitrile phenylpiperidines villaumite, and productive rate is 74.8%.
Embodiment 10
Synthesizing of two (perfluoroalkyl group sulfonyl) inferior amine salts of N-methyl-N-butyronitrile phenylpiperidines
With embodiment 2, but replace 18.9g (0.1mol) N-methyl-N-butyronitrile base tetramethyleneimine villaumite with 20.3g (0.1mol) N-methyl-N-butyronitrile phenylpiperidines villaumite, all the other conditions are constant.Reaction obtains colourless liquid after finishing, and is two (perfluoroalkyl group sulfonyl) inferior amine salts of product N-methyl-N-butyronitrile phenylpiperidines, and productive rate is 83.2%, and electrochemical window is 5.4V.
Claims (4)
1. ionic liquid with high electrochemical stability, it is characterized in that the ionic liquid cationic moiety is selected from the quaternary ammonium cation of itrile group functionalization, anionicsite is selected from chlorine, bromine, iodine, the fluoroboric acid root, hexafluorophosphoric acid root, sulfate radical, nitrate radical, the trifluoracetic acid root, trifluoromethayl sulfonic acid root, a kind of in two (perfluoroalkyl group sulfonyl) imido grpup negative ion, dintrile amine root and the asccharin acid group; The structural formula of quaternary ammonium cation is:
Wherein, n is the integer of 0-15, and X is O, and C, a kind of among the N, R are a kind of in methyl, ethyl, propyl group, butyl, sec.-propyl or the isobutyl-.
2. preparation method of ionic liquid according to claim 1, it is characterized in that: with excessive exsiccant R1X, wherein X represents halogen, R
1Representative contains the hydrocarbon of itrile group, and exsiccant five-ring or six-ring tertiary amine in molar ratio 1.1: 1-1.9: 1 mixes mutually, keeps 10-100 ℃, reacted several hours to tens hours, vacuumize then, slough volatile composition, obtain the ionic liquid that anionicsite is chlorine, bromine or iodine.
3. preparation method of ionic liquid according to claim 1 is characterized in that: with excessive exsiccant R
1X, wherein X represents halogen, R
1Representative contains the hydrocarbon of itrile group, and exsiccant five-ring or six-ring tertiary amine in molar ratio 1.1: 1-1.9: 1 mixes mutually, keeps 10-100 ℃, reacted several hours to tens hours, vacuumize then, slough volatile composition, obtain the ionic liquid that anionicsite is chlorine, bromine or iodine; Under the room temperature, with equimolar anionicsite is the ionic liquid of chlorine, bromine or iodine, be dissolved in ethanol with sodium tetrafluoroborate or SODIUMNITRATE, allowed halide-ions all generate precipitation in mechanical stirring 24-48 hour, through ageing, after the filtration treatment,, obtain containing the ionic liquid of tetrafluoroborate, nitrate radical with the filtrate evaporate to dryness.
4. preparation method of ionic liquid according to claim 1 is characterized in that: with excessive exsiccant R
1X, wherein X represents halogen, R
1Representative contains the hydrocarbon of itrile group, and exsiccant five-ring or six-ring tertiary amine in molar ratio 1.1: 1-1.9: 1 mixes mutually, keeps 10-100 ℃, reacted several hours to tens hours, vacuumize then, slough volatile composition, obtain the ionic liquid that anionicsite is chlorine, bromine or iodine; Under the room temperature, with equimolar anionicsite is the ionic liquid of chlorine, bromine or iodine, soluble in water with ammonium hexafluorophosphate or two (trifluoromethane sulphonyl) imido grpup lithium, under 0-10 ℃ lesser temps stirring reaction 2-24 hour, separate the ionic liquid that obtains containing hexafluoro-phosphate radical, two (trifluoromethane sulphonyl) imines acid group.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009132740A2 (en) * | 2008-04-29 | 2009-11-05 | Merck Patent Gmbh, | Reactive ionic liquids |
| CN102097213A (en) * | 2011-01-30 | 2011-06-15 | 中国科学院广州能源研究所 | Sulfur-based ion liquid based multi-sulfur electrolyte for quantum dot sensitized solar cell and preparation method thereof |
| CN103113242A (en) * | 2012-12-28 | 2013-05-22 | 中国科学院广州能源研究所 | Functional choline chloride ionic liquid and preparation method and application in electrochemical energy storage device thereof |
| CN103618111A (en) * | 2013-12-13 | 2014-03-05 | 东莞市凯欣电池材料有限公司 | Ion liquid electrolytic solution and secondary lithium battery containing electrolytic solution |
-
2006
- 2006-12-26 CN CN 200610105394 patent/CN101210000A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009132740A2 (en) * | 2008-04-29 | 2009-11-05 | Merck Patent Gmbh, | Reactive ionic liquids |
| WO2009132740A3 (en) * | 2008-04-29 | 2010-02-25 | Merck Patent Gmbh, | Reactive ionic liquids |
| US9006457B2 (en) | 2008-04-29 | 2015-04-14 | Basf Se | Reactive ionic liquids |
| US9624160B2 (en) | 2008-04-29 | 2017-04-18 | Basf Se | Reactive ionic liquids |
| CN102097213A (en) * | 2011-01-30 | 2011-06-15 | 中国科学院广州能源研究所 | Sulfur-based ion liquid based multi-sulfur electrolyte for quantum dot sensitized solar cell and preparation method thereof |
| CN102097213B (en) * | 2011-01-30 | 2012-07-25 | 中国科学院广州能源研究所 | Sulfur-based ion liquid based multi-sulfur electrolyte for quantum dot sensitized solar cell and preparation method thereof |
| CN103113242A (en) * | 2012-12-28 | 2013-05-22 | 中国科学院广州能源研究所 | Functional choline chloride ionic liquid and preparation method and application in electrochemical energy storage device thereof |
| CN103113242B (en) * | 2012-12-28 | 2015-04-22 | 中国科学院广州能源研究所 | Functional choline chloride ionic liquid and preparation method and application in electrochemical energy storage device thereof |
| CN103618111A (en) * | 2013-12-13 | 2014-03-05 | 东莞市凯欣电池材料有限公司 | Ion liquid electrolytic solution and secondary lithium battery containing electrolytic solution |
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