CN103130776A - Imidazoles ionic liquid containing carbonic ester perssad and preparation method and application thereof - Google Patents

Imidazoles ionic liquid containing carbonic ester perssad and preparation method and application thereof Download PDF

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CN103130776A
CN103130776A CN2011103934014A CN201110393401A CN103130776A CN 103130776 A CN103130776 A CN 103130776A CN 2011103934014 A CN2011103934014 A CN 2011103934014A CN 201110393401 A CN201110393401 A CN 201110393401A CN 103130776 A CN103130776 A CN 103130776A
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carbonate
containing group
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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 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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Abstract

The invention belongs to the field of ionic liquid and discloses an imidazoles ionic liquid containing carbonic ester perssad and a preparation method and application thereof. The ionic liquid has the following structural formula. In the formula, R is 0<=n<=4, Y- is selected from BF4-, PF6-, (CF3SO2)2N- or CF3SO3-. According to the imidazoles ionic liquid containing the carbonic ester perssad, by bringing the carbonic ester perssad into positive ions, the performance of the ionic liquid can be improved. On one hand, in electrolyte solution containing lithium salt, the carbonic ester structure has a good dissolving and dissociation function on the lithium salt; on the other hand, the ionic liquid containing the carbonic ester structures can generate an SEI film well, so that electrochemical stability of the ionic liquid electrolyte solution can be improved.

Description

Glyoxaline ion liquid of carbonate-containing group and its preparation method and application
Technical field
The present invention relates to the ionic liquid field, relate in particular to glyoxaline ion liquid of a kind of carbonate-containing group and its preparation method and application.
Background technology
Ionic liquid (Ionic liquids) refers to (be generally below 100 ℃) in room temperature range and is in a liquid state, and is made of organic cation and inorganic anion (or organic anion).Ionic liquid has adjustability, change according to different needs the purpose that its zwitterion structure can reach the planner, thereby ionic liquid is called as planner's solvent.Just found first ionic liquid----nitro ethamine as far back as 1914; But thereafter, the progress in this field is slow.Until 1992, Wikes leader's research group has synthesized low melting point, resistant to hydrolysis, stable strong 1-ethyl-3-methylimidazole tetrafluoroborate ion liquid ([EMIM] BF 4) after, the research of ionic liquid is just developed rapidly, has developed subsequently a series of ion liquid system.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 advantages of a series of outstanding: (1) fusing point lower than or near room temperature, the temperature range that is in a liquid state is wide; (2) steam force down, hardly the volatilization, colourless, odorless; (3) has larger equilibrium temperature scope, preferably chemical stability and wider electrochemical stability potential window; (4) good dissolution characteristics all shows good dissolving power to a lot of inorganicss and organism; (5) without point of ignition and nonflammable; (6) can be recycled, free from environmental pollution etc.
At present, to the research of ionic liquid mainly concentrate on novel ion liquid synthetic, ionic liquid physics and chemistry characteristic sign and as aspects such as solvent and electrolytical applied researcies.Ionic liquid is as the novel solvent of a class, medium, catalyzer, and the research in fields such as organic synthesis, catalyzed reaction, extracting and separating, material preparation, natural polymer, electrochemistry has obtained many gratifying results, has been subject to paying close attention to widely.
Summary of the invention
Based on the problems referred to above, one of purpose of the present invention is to provide a kind of glyoxaline ion liquid of novel carbonate-containing group.
A kind of glyoxaline ion liquid of carbonate-containing group, it comprises following structural formula:
Figure BDA0000115159880000021
In formula, R is
Figure BDA0000115159880000022
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 provide the preparation method of the glyoxaline ion liquid of above-mentioned carbonate-containing group, comprise the steps:
S1, be that 1: 1.1～1.2 3-Methylimidazole and RX carry out building-up reactions with mol ratio, make structural formula after reaction finishes and be
Figure BDA0000115159880000023
The 3-Methylimidazole halogenide of carbonate-containing group; Wherein, R is
Figure BDA0000115159880000024
0≤n≤4; X is halogen element, is selected from Cl or Br;
3-Methylimidazole halogenide and the inorganic salt MY of S2, described carbonate-containing group that step S1 is made carry out ion exchange reaction according to the mol ratio of 1: 1, make structural formula after reaction finishes and are The glyoxaline ion liquid of described carbonate-containing group; Wherein, in MY, M +For the 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 under inert atmosphere; This inert atmosphere is to comprise by at least a gas composition in nitrogen and argon gas; In described step S1, described building-up reactions stirs 48～72h and carries out under 60～80 ℃.
The glyoxaline ion liquid that another purpose of the present invention is to provide above-mentioned carbonate-containing group in ultracapacitor or lithium ion battery as the application of electrolytic solution.
The glyoxaline ion liquid of carbonate-containing group provided by the invention by introduce carbonate group in positively charged ion, improves the performance of ionic liquid, is on the one hand containing lithium salts (as, LiBF 4, LiPF 6, LiTFSI, (CF 3SO 2) 2NLi or CF 3SO 3Li) in electrolytic solution, this carbonic ether structure has good dissolving and the effect of dissociating to lithium salts; The ionic liquid that contains on the other hand the carbonic ether structure can generate SEI film (being solid-electrolyte interface film) preferably, thereby improves the electrochemical stability of il electrolyte.
The glyoxaline ion liquid preparation method of carbonate group provided by the invention, preparation technology is simple, is suitable for scale operation production.
Description of drawings
Fig. 1 is preparation technology's schema of the glyoxaline ion liquid of carbonate-containing group of the present invention;
Fig. 2 is the charging and discharging curve of the button cell of the embodiment of the present invention 6 preparations.
Embodiment
The glyoxaline ion liquid of carbonate-containing group provided by the invention, it comprises following structural formula:
Figure BDA0000115159880000031
In formula, R is
Figure BDA0000115159880000041
0≤n≤4; Y -Be selected from BF 4 -, PF 6 -, (CF 3SO 2) 2N -Or CF 3SO 3 -
The preparation method of the glyoxaline ion liquid of above-mentioned carbonate-containing group as shown in Figure 1, comprises the steps:
S1, be that 1: 1.1～1.2 3-Methylimidazole and RX (being the halo carbonic ether) carry out building-up reactions with mol ratio, make structural formula after reaction finishes and be
Figure BDA0000115159880000042
The 3-Methylimidazole halogenide 3-Methylimidazole halogen of carbonate-containing group (or be called) of carbonate-containing group; Wherein, R is
Figure BDA0000115159880000043
0≤n≤4; X is halogen element, is selected from Cl or Br; Its reaction formula is as follows:
Figure BDA0000115159880000044
Wherein, RX is
Figure BDA0000115159880000045
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 the chlorocarbonic acid vinyl acetate; N is 4 o'clock, is chlorocarbonic acid hexene ester; All the other are analogized;
3-Methylimidazole halogenide and the inorganic salt MY of S2, described carbonate-containing group that step S1 is made carry out ion exchange reaction according to the mol ratio of 1: 1, make structural formula after reaction finishes and are
Figure BDA0000115159880000051
The glyoxaline ion liquid of described carbonate-containing group; Wherein, in MY, M +For the 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:
Figure BDA0000115159880000052
In above-mentioned preparation method, in step S1: building-up reactions is carried out under inert atmosphere; This inert atmosphere is the inert atmosphere that comprises by nitrogen or the arbitrary gas composition of argon gas, and described building-up reactions stirs 48～72h and carries out under 60～80 ℃.
In above-mentioned preparation method, the building-up reactions in step S1 also comprises the purification step to the imidazolium halides of carbonate-containing group after finishing:
Reaction solution is standing cooling, then with the ethyl acetate washing repeatedly; 80 ℃ of lower vacuum-dryings, obtain lurid pure solid, i.e. the imidazolium halides of carbonate-containing group subsequently;
In above-mentioned preparation method, the ion exchange reaction in step S2 also comprises the purification step to the glyoxaline ion liquid of carbonate-containing group after finishing:
Reaction mixture is used the 250mL dichloromethane extraction repeatedly, combining extraction liquid; Then at every turn with the deionized water back extraction until with saturated AgNO 3Till aqueous solution titration water produces without precipitation; Then, methylene dichloride is concentrated with Rotary Evaporators, obtains colourless liquid after 80 ℃ of vacuum-drying 48h, is the glyoxaline ion liquid of carbonate-containing group.
The glyoxaline ion liquid of above-mentioned carbonate-containing group in ultracapacitor or lithium ion battery as the application of electrolytic solution.
The glyoxaline ion liquid of carbonate-containing group provided by the invention by introduce carbonate group in positively charged ion, improves the performance of ionic liquid, is on the one hand containing lithium salts (as, LiBF 4, LiPF 6, LiTFSI, (CF 3SO 2) 2NLi or CF 3SO 3Li) in electrolytic solution, this carbonic ether structure has good dissolving and the effect of dissociating to lithium salts; The ionic liquid that contains on the other hand the carbonic ether structure can generate SEI film (being solid-electrolyte interface film) preferably, thereby improves the electrochemical stability of il electrolyte.
The glyoxaline ion liquid preparation method of carbonate group provided by the invention, preparation technology is simple, is suitable for scale operation production.
The below is described in further detail preferred embodiment of the present invention.
Synthesizing of embodiment 1 1-propylene carbonate ester group-3-methyl imidazolium tetrafluoroborate
1, add respectively (83g, 1mol) 3-Methylimidazole and (149.6g, 1.1mol) chlorocarbonic acid propylene in the flask of 250mL; Then at N 2Under the atmosphere protection, be warming up to 60 ℃, stir building-up reactions 72h; Standing cooling subsequently, wash resultant 3 times with ethyl acetate, and 80 ℃ of lower vacuum-dryings, obtain lurid 1-propylene carbonate ester group-3-Methylimidazole villaumite, yield is 71%;
2, with the above-mentioned 1-propylene carbonate ester group that makes-3-Methylimidazole villaumite (109.5g, 0.5mol), NaBF 4(or KBF 4) (55g, 0.5mol) and 100mL deionized water add in the flask of 500mL, stirring reaction 10h at room temperature; After reaction is completed, obtain mixed solution; Then, mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then at every turn with 60mL deionized water back extraction until with saturated AgNO 3Till aqueous solution titration water produces without precipitation; After methylene dichloride was concentrated with Rotary Evaporators, 80 ℃ of vacuum-drying 48h obtained colourless liquid, are 1-propylene carbonate ester group-3-methyl imidazolium tetrafluoroborate ionic liquid.
The nuclear magnetic resonance spectrum diagram data of 1-propylene carbonate ester group-3-methyl imidazolium tetrafluoroborate is as follows:
1H?NMR(CDCl 3，400MHz，ppm)：9.12(s，1H)，7.71(s，1H)，7.78(s，1H)，4.88(d，2H)，4.82(m，1H)，4.72(d，2H)，3.93(s，3H).
Synthesizing of embodiment 2 1-ethylene carbonate ester groups-3-Methylimidazole hexafluorophosphate
1, add respectively (83g, 1mol) 3-Methylimidazole and (182.6g, 1.1mol) bromo NSC 11801 in the flask of 250mL; Then at Ar 2Under the atmosphere protection, be warming up to 80 ℃, stir building-up reactions 48h; Standing cooling subsequently, with ethyl acetate washing 3 times, and 80 ℃ of lower vacuum-dryings, obtain lurid 1-ethylene carbonate ester group-3-Methylimidazole bromine salt, yield is 74%;
2, with the above-mentioned 1-ethylene carbonate ester group that makes-3-Methylimidazole bromine salt (124.5g, 0.5mol), KPF 6(92g, 0.5mol) and 150mL deionized water add in the 500mL flask, at room temperature stir ion exchange reaction 24h; The reaction complete after, or mixing solutions; Then, mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then at every turn with 60mL deionized water back extraction until with saturated AgNO 3Till aqueous solution titration water produces without precipitation; After methylene dichloride was concentrated with Rotary Evaporators, 80 ℃ of vacuum-drying 48h obtained colourless liquid, are 1-ethylene carbonate ester group-3-Methylimidazole hexafluorophosphate ionic liquid.
Synthesizing of two (fluoroform sulfimide) salt of embodiment 3 1-butylene carbonate ester group-3-Methylimidazoles
1, add respectively (83g, 1mol) 3-Methylimidazole and (213.4g, 1.1mol) bromo butylene in the flask of 250mL.At N 2Under the atmosphere protection, be warming up to 65 ℃, stirring reaction 60h; Standing cooling, with ethyl acetate washing 3 times.80 ℃ of lower vacuum-dryings, obtain lurid 1-butylene carbonate ester group-3-Methylimidazole bromine salt, yield is 78%.
2, add (138.5g, 0.5mol) 1-butylene carbonate ester group-3-Methylimidazole bromine salt, (159.5g, 0.5mol) fluoroform sulfimide potassium (CF in the 500mL flask 3SO 2) 2NK and 120mL deionized water, at room temperature stirring reaction 12h.After reaction is completed, obtain mixing solutions; Then, mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then at every turn with 60mL deionized water back extraction until with saturated AgNO 3Till aqueous solution titration water produces without precipitation; After methylene dichloride was concentrated with Rotary Evaporators, 80 ℃ of vacuum-drying 48h obtained colourless liquid, were two (fluoroform sulfimide) the salt ion liquid of 1-butylene carbonate ester group-3-Methylimidazole.
Synthesizing of embodiment 4 1-carbonic acid amylene ester group-3-Methylimidazole fluoroform sulphonates
1, add respectively (83g, 1mol) 3-Methylimidazole and (196.8g, 1.2mol) chlorocarbonic acid amylene ester in the flask of 250mL.At N 2Under the atmosphere protection, be warming up to 70 ℃, stirring reaction 50h; Standing cooling, with ethyl acetate washing 3 times; 80 ℃ of lower vacuum-dryings, obtain lurid 1-carbonic acid amylene ester group-3-Methylimidazole villaumite, yield is 77%.
2, add (122.5g, 0.5mol) 1-carbonic acid amylene ester group-3-Methylimidazole villaumite, (86g, 0.5mol) CF in a 250mL flask 3SO 3Na and 140mL deionized water, at room temperature stirring reaction 18h.After reaction is completed, mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then at every turn with 60mL deionized water back extraction until with saturated AgNO 3Till aqueous solution titration water produces without precipitation.Methylene dichloride is concentrated with Rotary Evaporators, obtains colourless liquid after 80 ℃ of vacuum-drying 48h, is 1-carbonic acid amylene ester group-3-Methylimidazole fluoroform sulphonate ionic liquid.
Synthesizing of embodiment 5 1-carbonic acid hexene ester group-3-methyl imidazolium tetrafluoroborate
1, add respectively (83g, 1mol) 3-Methylimidazole and (266.4g, 1.2mol) bromo carbonic acid hexene ester in the flask of 250mL.At N 2And Ar 2Form under the protection of mixed gas atmosphere, be warming up to 60 ℃, stirring reaction 72h.Standing cooling, with ethyl acetate washing 3 times.80 ℃ of lower vacuum-dryings, obtain lurid 1-carbonic acid hexene ester group-3-Methylimidazole bromine salt, yield is 79%.
2, add (152.5g, 0.5mol) 1-carbonic acid hexene ester group-3-Methylimidazole bromine salt, (52.5g, 0.5mol) NH in a 250mL flask 4BF 4With the 130mL deionized water, stirring reaction 15h at room temperature; After reaction is completed, mixed solution 250mL dichloromethane extraction 3 times, combining extraction liquid; Then at every turn with 60mL deionized water back extraction until with saturated AgNO 3Till aqueous solution titration water produces without precipitation.Methylene dichloride is concentrated with Rotary Evaporators, obtains colourless liquid after 80 ℃ of vacuum-drying 48h, is 1-carbonic acid hexene ester group-3-methyl imidazolium tetrafluoroborate ionic liquid.
Embodiment 6
The present embodiment is take two (fluoroform sulfimide) salt of the 1-butylene carbonate ester group of embodiment 3-3-Methylimidazole as ionic liquid.
Take Graphene as electrode materials, electrolytic solution used is two (fluoroform sulfimide) salt of 1mol/L LiTFSI/1-butylene carbonate ester group-3-Methylimidazole+10wt.% acetonitrile, 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-3-Methylimidazole; stir, the concentration that makes LiTFSI is 1mol/L.Then, add the acetonitrile that accounts for total mass 10% in system, and mix.
Utilize the CHI660A electrochemical workstation to carry out the constant current charge-discharge test to it, in the electrochemical window of 0～3.0V, electric current with 0.5A/g records its charging and discharging curve, as can be seen from Figure 2, the electrolytic solution prepared of the embodiment of the present invention has cyclical stability preferably in the charging voltage up to 3.0V.
Should be understood that, above-mentioned statement for preferred embodiment of the present invention is comparatively detailed, can not therefore think the restriction to scope of patent protection of the present invention, and scope of patent protection of the present invention should be as the criterion with claims.

Claims (10)

1. the glyoxaline ion liquid of a carbonate-containing group, is characterized in that, it comprises following structural formula:
Figure FDA0000115159870000011
In formula, R is
Figure FDA0000115159870000012
0≤n≤4; Y -Be selected from BF 4 -, PF 6 -, (CF 3SO 2) 2N -Or CF 3SO 3 -
2. the preparation method of the glyoxaline ion liquid of a carbonate-containing group, is characterized in that, comprises the steps:
S1, be that 1: 1.1～1.2 3-Methylimidazole and RX carry out building-up reactions with mol ratio, make structural formula after reaction finishes and be
Figure FDA0000115159870000013
The 3-Methylimidazole halogenide of carbonate-containing group; Wherein, R is 0≤n≤4; X is halogen element;
3-Methylimidazole halogenide and the inorganic salt MY of S2, described carbonate-containing group that step S1 is made carry out ion exchange reaction according to the mol ratio of 1: 1, make structural formula after reaction finishes and are
Figure FDA0000115159870000015
The glyoxaline ion liquid of described carbonate-containing group; Wherein, in MY, M +Be the processable positively charged ion; Y -Be selected from BF 4 -, PF 6 -, (CF 3SO 2) 2N -Or CF 3SO 3 -
3. the preparation method of the glyoxaline ion liquid of carbonate-containing group according to claim 2, is characterized in that, in step S1, X is Cl or Br.
4. the preparation method of the glyoxaline ion liquid of carbonate-containing group according to claim 2, is characterized in that, the building-up reactions in step S1 is carried out under inert atmosphere.
5. the preparation method of the glyoxaline ion liquid of carbonate-containing group according to claim 4, is characterized in that, described inert atmosphere is to comprise by at least a gas composition in nitrogen and argon gas.
According to claim 2 to 5 arbitrary described carbonate-containing group the preparation method of glyoxaline ion liquid, it is characterized in that, in described step S1, described building-up reactions stirs 48～72h and carries out under 60～80 ℃.
7. the preparation method of the glyoxaline ion liquid of carbonate-containing group according to claim 6, is characterized in that, the building-up reactions in described step S1 also comprises the purification step to the imidazolium halides of described carbonate-containing group after finishing.
8. the preparation method of the glyoxaline ion liquid of carbonate-containing group according to claim 2, is characterized in that, in step S2, and M +Be selected from Na +, K +Or NH 4 +
9. the preparation method of the glyoxaline ion liquid of according to claim 2 or 8 described carbonate-containing groups, it is characterized in that, ion exchange reaction in described step S2 also comprises the purification step that contains the glyoxaline ion liquid of carbonate-containing group to described after finishing.
The glyoxaline ion liquid of carbonate-containing group claimed in claim 1 in ultracapacitor or lithium ion battery as the application of electrolytic solution.
CN2011103934014A 2011-12-01 2011-12-01 Imidazoles ionic liquid containing carbonic ester perssad and preparation method and application thereof Pending CN103130776A (en)

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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

Patent Citations (6)

* 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
US20060210876A1 (en) * 2005-03-17 2006-09-21 Takashi Kuboki Electrochemical device
CN101679292A (en) * 2007-06-12 2010-03-24 日宝化学株式会社 Ionic liquid and method for producing the same
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Application publication date: 20130605