CN103130778B - Pyrazine ionic liquid of carbonate-containing group and its preparation method and application - Google Patents

Pyrazine ionic liquid of carbonate-containing group and its preparation method and application Download PDF

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Publication number
CN103130778B
CN103130778B CN201110393186.8A CN201110393186A CN103130778B CN 103130778 B CN103130778 B CN 103130778B CN 201110393186 A CN201110393186 A CN 201110393186A CN 103130778 B CN103130778 B CN 103130778B
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pyrazine
carbonate
ionic liquid
containing group
preparation
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CN103130778A (en
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周明杰
刘大喜
王要兵
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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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
    • Y02E60/10—Energy storage using batteries
    • 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

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Abstract

The invention belongs to field of ionic liquid, it discloses pyrazine ionic liquid of a kind of carbonate-containing group and its preparation method and application; This ionic liquid has following structural formula: in formula, R is 0≤n≤4; Y -be selected from BF 4 -, PF 6 -, (CF 3sO 2) 2n -or CF 3sO 3 -.The pyrazine ionic liquid of carbonate-containing group provided by the invention, by introducing carbonate group in positively charged ion, the performance of ionic liquid is improved, and on the one hand in the electrolytic solution containing lithium salts, this structural carbonate has good dissolving and dissociation to lithium salts; Ionic liquid on the other hand containing structural carbonate can generate SEI film preferably, thus improves the electrochemical stability of il electrolyte.

Description

Pyrazine ionic liquid of carbonate-containing group and its preparation method and application
Technical field
The present invention relates to field of ionic liquid, particularly relate to pyrazine ionic liquid of a kind of carbonate-containing group and its preparation method and application.
Background technology
Ionic liquid (Ionicliquids) 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).Ionic liquid has adjustability, and need to change the object that its zwitterion structure can reach planner according to difference, thus ionic liquid is called as the solvent of planner.First ionic liquid has just been found as far back as 1914----nitro ethamine; But thereafter, the progress in this field is slow.Until 1992, the research group of Wikes leader has synthesized low melting point, resistant to hydrolysis, 1-ethyl-Ji tetrafluoroborate ionic liquid ([EMIM] BF that stability is strong 4) after, the research of ionic liquid is just developed rapidly, have developed a series of ion liquid system subsequently.Initial ionic liquid is mainly used in electrochemical research, and ionic liquid comes into one's own for organic and Polymer Synthesizing as green solvent in recent years.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.
At present, the synthesis of novel ion liquid, the sign of ionic liquid physics and chemistry characteristic and as the aspect such as solvent and electrolytical applied research are mainly concentrated on to the research of ionic liquid.Ionic liquid, as novel solvent, medium, the catalyzer of a class, achieves many gratifying results in the research in the fields such as organic synthesis, catalyzed reaction, extracting and separating, material preparation, natural polymer, electrochemistry, receives and pay close attention to widely.
Summary of the invention
Based on the problems referred to above, an object of the present invention is the pyrazine ionic liquid providing a kind of novel carbonate-containing group.
A pyrazine ionic liquid for carbonate-containing group, it comprises following structural formula:
In formula, R is 0≤n≤4; Y -be selected from BF 4 -, PF 6 -, (CF 3sO 2) 2n -or CF 3sO 3 -.
Another object of the present invention is to the preparation method of the pyrazine ionic liquid that above-mentioned carbonate-containing group is provided, comprise the steps:
S1, by mol ratio be 1: 1.1 ~ 1.2 pyrazine and RX carry out building-up reactions, reaction terminates rear obtained structural formula and is the pyrazine halogenide of carbonate-containing group; Wherein, R is 0≤n≤4; X is halogen element, is selected from Cl or Br;
S2, the pyrazine halogenide of described carbonate-containing group obtained by step S1 and inorganic salt MY carry out ion exchange reaction according to the mol ratio of 1: 1, and reaction terminates rear obtained structural formula and is the pyrazine ionic liquid of described carbonate-containing group; Wherein, in MY, M +for processable positively charged ion, be selected from Na +, K +or NH 4 +; Y -be selected from BF 4 -, PF 6 -, (CF 3sO 2) 2n -or CF 3sO 3 -.
In above-mentioned preparation method, the building-up reactions in step S1 is carried out in an inert atmosphere; This inert atmosphere comprises by least one gas composition in nitrogen and argon gas; In described step S1, described building-up reactions stirs 48 ~ 72h and carries out at 60 ~ 80 DEG C.
Another object of the present invention is to provide the pyrazine ionic liquid of above-mentioned carbonate-containing group in ultracapacitor or lithium ion battery as the application of electrolytic solution.
The pyrazine ionic liquid of carbonate-containing group provided by the invention, by introducing carbonate group in positively charged ion, makes the performance of ionic liquid improve, and is containing lithium salts (e.g., LiBF on the one hand 4, LiPF 6, LiTFSI, (CF 3sO 2) 2nLi or CF 3sO 3li), in electrolytic solution, this structural carbonate has good dissolving and dissociation to lithium salts; Ionic liquid on the other hand containing structural carbonate can generate SEI film (i.e. solid-electrolyte interface film) preferably, thus improves the electrochemical stability of il electrolyte.
The pyrazine ionic liquid preparation method of carbonate group provided by the invention, preparation technology is simple, is suitable for scale operationization and produces.
Accompanying drawing explanation
Fig. 1 is preparation technology's schema of the pyrazine ionic liquid of carbonate-containing group of the present invention;
Fig. 2 is the charging and discharging curve of button cell prepared by the embodiment of the present invention 6.
Embodiment
The pyrazine ionic liquid of carbonate-containing group provided by the invention, it comprises following structural formula:
In formula, R is 0≤n≤4; Y -be selected from BF 4 -, PF 6 -, (CF 3sO 2) 2n -or CF 3sO 3 -.
The preparation method of the pyrazine ionic liquid of above-mentioned carbonate-containing group, as shown in Figure 1, comprises the steps:
S1, by mol ratio be 1: 1.1 ~ 1.2 pyrazine and RX (i.e. halocarbonate) carry out building-up reactions,
Reaction terminates rear obtained structural formula and is the pyrazine halogenide (or being called the pyrazine halogen of carbonate-containing group) of carbonate-containing group; Wherein, R is 0≤n≤4; X is halogen element, is selected from Cl or Br; Its reaction formula is as follows:
Wherein, RX is be selected from chlorocarbonic acid vinyl acetate, chlorocarbonic acid propylene, chlorocarbonic acid butene esters, chlorocarbonic acid amylene ester, chlorocarbonic acid hexene ester, bromo NSC 11801, bromo propylene carbonate, bromo butylene, bromo carbonic acid amylene ester or bromo carbonic acid hexene ester etc.; When n is 0, it is exactly chlorocarbonic acid vinyl acetate; When n is 4, it is chlorocarbonic acid hexene ester.All the other, analogize;
S2, the pyrazine halogenide of described carbonate-containing group obtained by step S1 and inorganic salt MY carry out ion exchange reaction according to the mol ratio of 1: 1, and reaction terminates rear obtained structural formula and is the pyrazine ionic liquid of described carbonate-containing group; Wherein, in MY, M +for processable positively charged ion, be selected from Na +, K +or NH 4 +; Y -be selected from BF 4 -, PF 6 -, (CF 3sO 2) 2n -or CF 3sO 3 -; Its reaction formula is as follows:
In above-mentioned preparation method, in step S1: building-up reactions is carried out in an inert atmosphere; This inert atmosphere is the inert atmosphere comprised by nitrogen or the arbitrary gas composition of argon gas, and described building-up reactions stirs 48 ~ 72h at 60 ~ 80 DEG C carries out.
In above-mentioned preparation method, after the building-up reactions in step S1 terminates, also comprise the halid purification step of the pyrazine of carbonate-containing group:
Reaction solution is left standstill cooling, then washs repeatedly by ethyl acetate; Vacuum-drying at 80 DEG C subsequently, obtains lurid neat solid, i.e. the pyrazine halogenide of carbonate-containing group;
In above-mentioned preparation method, after the ion exchange reaction in step S2 terminates, also comprise the purification step of the pyrazine ionic liquid to carbonate-containing group:
Reaction mixture with 250mL dichloromethane extraction repeatedly, combining extraction liquid; Then use deionized water back extraction until with saturated AgNO at every turn 3till aqueous solution titration aqueous phase produces without precipitation; Then, methylene dichloride Rotary Evaporators concentrates, and obtains colourless liquid, be the pyrazine ionic liquid of carbonate-containing group after 80 DEG C of vacuum-drying 48h.
The pyrazine ionic liquid of above-mentioned carbonate-containing group in ultracapacitor or lithium ion battery as the application of electrolytic solution.
The pyrazine ionic liquid of carbonate-containing group provided by the invention, by introducing carbonate group in positively charged ion, makes the performance of ionic liquid improve, and is containing lithium salts (e.g., LiBF on the one hand 4, LiPF 6, LiTFSI, (CF 3sO 2) 2nLi or CF 3sO 3li), in electrolytic solution, this structural carbonate has good dissolving and dissociation to lithium salts; Ionic liquid on the other hand containing structural carbonate can generate SEI film (i.e. solid-electrolyte interface film) preferably, thus improves the electrochemical stability of il electrolyte.
The pyrazine ionic liquid preparation method of carbonate group provided by the invention, preparation technology is simple, is suitable for scale operationization and produces.
Below preferred embodiment of the present invention is described in further detail.
The synthesis of embodiment 11-propylene carbonate ester group pyrazine a tetrafluoro borate
1, in the flask of 250mL, add (80g, 1mol) pyrazine and (149.6g, 1.1mol) chlorocarbonic acid propylene respectively; Then at N 2under atmosphere protection, be warming up to 60 DEG C, stir building-up reactions 72h; Leave standstill cooling subsequently, wash resultant 3 times by ethyl acetate, and vacuum-drying at 80 DEG C, obtain lurid 1-propylene carbonate ester group pyrazine villaumite, yield is 71%;
2, by above-mentioned obtained 1-propylene carbonate ester group pyrazine villaumite (108g, 0.5mol), NaBF 4(or KBF 4) (55g, 0.5mol) and 100mL deionized water add in the flask of 500mL, at room temperature stirring reaction 10h; After having reacted, obtain mixed solution; Then, mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then use the back extraction of 60mL deionized water until with saturated AgNO at every turn 3till aqueous solution titration aqueous phase produces without precipitation; After methylene dichloride is concentrated with Rotary Evaporators, 80 DEG C of vacuum-drying 48h obtain colourless liquid, are 1-propylene carbonate ester group pyrazine tetrafluoroborate ion liquid.
The nuclear magnetic resonance spectrum diagram data of 1-propylene carbonate ester group pyrazine a tetrafluoro borate is as follows:
1HNMR(CDCl 3，400MHz，ppm)：8.78(d，2H)，8.65(d，2H)，4.88(d，2H)，4.82(m，1H)，4.72(d，2H).
The synthesis of embodiment 21-ethylene carbonate ester group pyrazine hexafluorophosphate
1, in the flask of 250mL, add (80g, 1mol) pyrazine and (182.6g, 1.1mol) bromo NSC 11801 respectively; Then at Ar 2under atmosphere protection, be warming up to 80 DEG C, stir building-up reactions 48h; Leave standstill cooling subsequently, wash 3 times by ethyl acetate, and vacuum-drying at 80 DEG C, obtain lurid 1-ethylene carbonate ester group pyrazine bromine salt, yield is 74%;
2, by above-mentioned obtained 1-ethylene carbonate ester group pyrazine bromine salt (123g, 0.5mol), KPF 6(92g, 0.5mol) and 150mL deionized water add in 500mL flask, at room temperature stir ion exchange reaction 24h; After having reacted, or mixing solutions; Then, mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then use the back extraction of 60mL deionized water until with saturated AgNO at every turn 3till aqueous solution titration aqueous phase produces without precipitation; After methylene dichloride is concentrated with Rotary Evaporators, 80 DEG C of vacuum-drying 48h obtain colourless liquid, are 1-ethylene carbonate ester group pyrazine phosphofluoric acid ionic liquid.
The synthesis of two (fluoroform sulfimide) salt of embodiment 31-butylene carbonate ester group pyrazine
1, in the flask of 250mL, add (80g, 1mol) pyrazine and (213.4g, 1.1mol) bromo butylene respectively.At N 2under atmosphere protection, be warming up to 65 DEG C, stirring reaction 60h; Leave standstill cooling, wash 3 times by ethyl acetate.Vacuum-drying at 80 DEG C, obtain lurid 1-butylene carbonate ester group pyrazine bromine salt, yield is 78%.
2, in 500mL flask, add (137g, 0.5mol) 1-butylene carbonate ester group pyrazine bromine salt, (159.5g, 0.5mol) fluoroform sulfimide potassium (CF 3sO 2) 2nK and 120mL deionized water, at room temperature stirring reaction 12h.After having reacted, obtain mixing solutions; Then, mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then use the back extraction of 60mL deionized water until with saturated AgNO at every turn 3till aqueous solution titration aqueous phase produces without precipitation; After methylene dichloride is concentrated with Rotary Evaporators, 80 DEG C of vacuum-drying 48h obtain colourless liquid, are two (fluoroform sulfimide) ionic liquid of 1-butylene carbonate ester group pyrazine.
The synthesis of embodiment 41-carbonic acid amylene ester group pyrazine fluoroform sulphonate
1, in the flask of 250mL, add (80g, 1mol) pyrazine and (196.8g, 1.2mol) chlorocarbonic acid amylene ester respectively.At N 2under atmosphere protection, be warming up to 70 DEG C, stirring reaction 50h; Leave standstill cooling, wash 3 times by ethyl acetate; Vacuum-drying at 80 DEG C, obtain lurid 1-carbonic acid amylene ester group pyrazine villaumite, yield is 77%.
2, in a 250mL flask, add (121g, 0.5mol) 1-carbonic acid amylene ester group pyrazine villaumite, (86g, 0.5mol) CF 3sO 3na and 140mL deionized water, at room temperature stirring reaction 18h.After having reacted, mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then use the back extraction of 60mL deionized water until with saturated AgNO at every turn 3till aqueous solution titration aqueous phase produces without precipitation.Methylene dichloride Rotary Evaporators concentrates, and obtains colourless liquid after 80 DEG C of vacuum-drying 48h, is 1-carbonic acid amylene ester group pyrazine trifluoromethanesulfonic acid ionic liquid.
The synthesis of embodiment 51-carbonic acid hexene ester group pyrazine a tetrafluoro borate
1, in the flask of 250mL, add (80g, 1mol) pyrazine and (266.4g, 1.2mol) bromo carbonic acid hexene ester respectively.At N 2and Ar 2under the protection of composition mixed gas atmosphere, be warming up to 60 DEG C, stirring reaction 72h.Leave standstill cooling, wash 3 times by ethyl acetate.Vacuum-drying at 80 DEG C, obtain lurid 1-carbonic acid hexene ester group pyrazine bromine salt, yield is 79%.
2, in a 250mL flask, add (151g, 0.5mol) 1-carbonic acid hexene ester group pyrazine bromine salt, (52.5g, 0.5mol) NH 4bF 4with 130mL deionized water, at room temperature stirring reaction 15h; After having reacted, mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then use the back extraction of 60mL deionized water until with saturated AgNO at every turn 3till aqueous solution titration aqueous phase produces without precipitation.Methylene dichloride Rotary Evaporators concentrates, and obtains colourless liquid after 80 DEG C of vacuum-drying 48h, is 1-carbonic acid hexene ester group pyrazine tetrafluoroborate ion liquid.
Embodiment 6
The present embodiment with two (fluoroform sulfimide) salt of the 1-butylene carbonate ester group pyrazine of embodiment 3 for ionic liquid.
Take Graphene as electrode materials, electrolytic solution used is two (fluoroform sulfimide) salt+10wt.% acetonitrile of 1mol/LLiTFSI/1-butylene carbonate ester group pyrazine, is assembled into button cell.
The process for preparation of electrolytic solution: under nitrogen protection; LiTFSI (i.e. two (trimethyl fluoride sulfonyl) imine lithium) is joined in two (fluoroform sulfimide) salt of 1-butylene carbonate ester group pyrazine; stir, make the concentration of LiTFSI be 1mol/L.Then, in system, add the acetonitrile accounting for total mass 10%, and be uniformly mixed.
CHI660A electrochemical workstation is utilized to carry out constant current charge-discharge test to it, in the electrochemical window of 0 ~ 2.7V, its charging and discharging curve is recorded with the electric current of 1.0A/g, as can be seen from Figure 2, the electrolytic solution prepared of the embodiment of the present invention is having good cyclical stability up in the charging voltage of 2.7V.
Should be understood that, the above-mentioned statement for present pre-ferred embodiments is comparatively detailed, and therefore can not think the restriction to scope of patent protection of the present invention, scope of patent protection of the present invention should be as the criterion with claims.

Claims (3)

1. a pyrazine ionic liquid for carbonate-containing group, is characterized in that, it comprises following structural formula:
In formula, R is n is 2; Y -for (CF 3sO 2) 2n -.
2. a preparation method for the pyrazine ionic liquid of carbonate-containing group, is characterized in that, comprises the steps:
S1, at N 2under atmosphere protection, be that pyrazine and the RX of 1:1.1 is warming up to 65 DEG C, stirring reaction 60h, carry out building-up reactions by mol ratio, reaction terminates rear standing cooling, and wash 3 times by ethyl acetate, vacuum-drying at 80 DEG C, obtained structural formula is the pyrazine halogenide of carbonate-containing group; Wherein, R is n is 2; X is bromo element;
S2, the pyrazine halogenide of described carbonate-containing group obtained by step S1 and inorganic salt MY carry out ion exchange reaction according to the mol ratio of 1:1, after having reacted, obtain mixing solutions, then, and mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then use the back extraction of 60mL deionized water until with saturated AgNO at every turn 3till aqueous solution titration aqueous phase produces without precipitation, after methylene dichloride is concentrated with Rotary Evaporators, 80 DEG C of vacuum-drying 48h obtain structural formula and are the pyrazine ionic liquid of described carbonate-containing group; Wherein, in MY, M +for K +; Y -for (CF 3sO 2) 2n -.
3. the pyrazine ionic liquid of carbonate-containing group according to claim 1 in ultracapacitor or lithium ion battery as the application of electrolytic solution.
CN201110393186.8A 2011-12-01 2011-12-01 Pyrazine ionic liquid of carbonate-containing group and its preparation method and application Expired - Fee Related CN103130778B (en)

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CN1934212A (en) * 2004-04-19 2007-03-21 Lg化学株式会社 Gel polymer electrolyte containing ionic liquid and electrochromic device using the same
CN101640291A (en) * 2008-07-29 2010-02-03 三星Sdi株式会社 Electrolyte and lithium ion secondary battery including the same
CN101679292A (en) * 2007-06-12 2010-03-24 日宝化学株式会社 Ionic liquid and method for producing the same
CN102138235A (en) * 2008-08-29 2011-07-27 法国原子能及替代能源委员会 Lithium-ion rechargeable accumulators including an ionic liquid electrolyte

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
JP4202334B2 (en) * 2005-03-17 2008-12-24 株式会社東芝 Electrochemical devices

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005027157A2 (en) * 2003-09-09 2005-03-24 Nat Inst Of Advanced Ind Scien Salt fusible at ordinary temperature and electrochemical device
CN1934212A (en) * 2004-04-19 2007-03-21 Lg化学株式会社 Gel polymer electrolyte containing ionic liquid and electrochromic device using the same
CN101679292A (en) * 2007-06-12 2010-03-24 日宝化学株式会社 Ionic liquid and method for producing the same
CN101640291A (en) * 2008-07-29 2010-02-03 三星Sdi株式会社 Electrolyte and lithium ion secondary battery including the same
CN102138235A (en) * 2008-08-29 2011-07-27 法国原子能及替代能源委员会 Lithium-ion rechargeable accumulators including an ionic liquid electrolyte

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