CN103130764A - Quaternary ammonium salt ionic liquid containing carbonic ester group and preparation method and application thereof - Google Patents

Quaternary ammonium salt ionic liquid containing carbonic ester group and preparation method and application thereof Download PDF

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CN103130764A
CN103130764A CN2011103931887A CN201110393188A CN103130764A CN 103130764 A CN103130764 A CN 103130764A CN 2011103931887 A CN2011103931887 A CN 2011103931887A CN 201110393188 A CN201110393188 A CN 201110393188A CN 103130764 A CN103130764 A CN 103130764A
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carbonate
containing group
quaternaries
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quaternary ammonium
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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 liquids and discloses a quaternary ammonium salt ionic liquid containing a carbonic ester group and a preparation method and application of the quaternary ammonium salt ionic liquid. The ionic liquid has the following structural formula. In the formula, R is 0<=n<=4, Y- is selected from BF4-, PF6- and (CF3SO2)2N- or CF3SO3-. According to the quaternary ammonium salt ionic liquid containing the carbonic ester group, through the method of introducing the carbonic ester group into positive ions, the performance of the ionic liquid can be improved. On one hand, in an electrolyte solution containing lithium salt, the carbonic ester structure has a good dissolving and dissociation function on the lithium salt; and on the other hand, the ionic liquid containing the carbonic ester structure can generate an SEI film well, so that electrochemical stability of the ionic liquid electrolyte solution is improved.

Description

Ion liquid of quaternaries 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 ion liquid of quaternaries 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 ion liquid of quaternaries of novel carbonate-containing group.
A kind of ion liquid of quaternaries of carbonate-containing group, it comprises following structural formula:
In formula, R is
Figure BDA0000115155460000022
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 ion liquid of quaternaries of above-mentioned carbonate-containing group, comprise the steps:
S1, be that 1: 1.1～1.2 triethylamine and RX carry out building-up reactions with mol ratio, make structural formula after reaction finishes and be
Figure BDA0000115155460000023
The quaternary ammonium halide (being perhaps the quaternary ammonium halides salt of carbonate-containing group) of carbonate-containing group; Wherein, R is
Figure BDA0000115155460000024
0≤n≤4; X is halogen element, is selected from Cl or Br;
Quaternary ammonium halide 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 BDA0000115155460000025
The ion liquid of quaternaries 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 ion liquid of quaternaries 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 ion liquid of quaternaries 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 ion liquid of quaternaries 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 ion liquid of quaternaries 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 ion liquid of quaternaries of carbonate-containing group provided by the invention, it comprises following structural formula:
Figure BDA0000115155460000031
In formula, R is
Figure BDA0000115155460000032
0≤n≤4; Y -Be selected from BF 4 -, PF 6 -, (CF 3SO 2) 2N -Or CF 3SO 3 -The preparation method of the ion liquid of quaternaries of above-mentioned carbonate-containing group as shown in Figure 1, comprises the steps:
S1, be that 1: 1.1～1.2 triethylamine and RX (being the halo carbonic ether) carry out building-up reactions with mol ratio, make structural formula after reaction finishes and be
Figure BDA0000115155460000041
The quaternary ammonium halide (perhaps being called halogenation carbonate-containing group quaternary ammonium salt) of carbonate-containing group; Wherein, R is
Figure BDA0000115155460000042
0≤n≤4; X is halogen element, is selected from Cl or Br; Its reaction formula is as follows:
Figure BDA0000115155460000043
Wherein, RX is
Figure BDA0000115155460000044
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;
Quaternary ammonium halide 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 BDA0000115155460000045
The ion liquid of quaternaries 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:
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 quaternary ammonium halide 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 quaternary ammonium halide of carbonate-containing group subsequently;
In above-mentioned preparation method, the ion exchange reaction in step S2 also comprises the purification step to the ion liquid of quaternaries 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 ion liquid of quaternaries of carbonate-containing group.
The ion liquid of quaternaries of above-mentioned carbonate-containing group in ultracapacitor or lithium ion battery as the application of electrolytic solution.
The ion liquid of quaternaries 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 ion liquid of quaternaries 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.
Embodiment 1N-propylene carbonate ester group-N, N, N-triethyl quaternary ammonium salt a tetrafluoro borate synthetic
1, add respectively (101g, 1mol) triethylamine 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 chlorination N-propylene carbonate ester group-N, N, N-triethyl quaternary ammonium salt, yield are 72%;
2, with the above-mentioned chlorination N-propylene carbonate ester group-N that makes, N, N-triethyl quaternary ammonium salt (118.5g, 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 N-propylene carbonate ester group-N, N, N-triethyl quaternary ammonium salt tetrafluoroborate ion liquid.
N-propylene carbonate ester group-N, N, the nuclear magnetic resonance spectrum diagram data of N-triethyl quaternary ammonium salt a tetrafluoro borate is as follows:
1H?NMR(CDCl 3，400MHz，ppm)：4.52(m，1H)，4.40(d，2H)，2.88(d，2H)，2.53(m，6H)，1.05(t，9H).
Embodiment 2N-ethylene carbonate ester group-N, N, N-triethyl quaternary ammonium salt hexafluorophosphate synthetic
1, add respectively (101g, 1mol) triethylamine 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 bromination N-ethylene carbonate ester group-N, N, N-triethyl quaternary ammonium salt, yield are 74%;
2, with the above-mentioned bromination N-ethylene carbonate ester group-N that makes, N, N-triethyl quaternary ammonium salt (133.5g, 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 N-ethylene carbonate ester group-N, N, N-triethyl quaternary ammonium salt hexafluorophosphate ionic liquid.
Embodiment 3N-butylene carbonate ester group-N, N, two (fluoroform sulfimide) salt of N-triethyl quaternary ammonium salt synthetic
1, add respectively (101g, 1mol) triethylamine 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 bromination N-butylene carbonate ester group-N, N, N-triethyl quaternary ammonium salt, yield are 78%.
2, add (147.5g, 0.5mol) bromination N-butylene carbonate ester group-N in the 500mL flask, N, N-triethyl quaternary ammonium salt, (159.5g, 0.5mol) fluoroform sulfimide potassium (CF 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, are N-butylene carbonate ester group-N, N, two (fluoroform sulfimide) the salt ion liquid of N-triethyl quaternary ammonium salt.
Synthesizing of embodiment 4N-carbonic acid amylene ester based quaternary ammonium salt fluoroform sulphonate
1, add respectively (101g, 1mol) triethylamine 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 chlorination N-carbonic acid amylene ester group-N, N, N-triethyl quaternary ammonium salt, yield are 77%.
2, add (121g, 0.5mol) chlorination N-carbonic acid amylene ester group-N, N, N-triethyl quaternary ammonium salt, (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 N-carbonic acid amylene ester group-N, N, N-triethyl quaternary ammonium salt fluoroform sulphonate ionic liquid.
Synthesizing of embodiment 5N-carbonic acid hexene ester based quaternary ammonium salt a tetrafluoro borate
1, add respectively (101g, 1mol) triethylamine 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 bromination N-carbonic acid hexene ester group-N, N, N-triethyl quaternary ammonium salt, yield are 79%.
2, add (151g, 0.5mol) bromination N-carbonic acid hexene ester group-N, N, N-triethyl quaternary ammonium 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 N-carbonic acid hexene ester group-N, N, N-triethyl quaternary ammonium salt tetrafluoroborate ion liquid.
Embodiment 6
The present embodiment is with N-butylene carbonate ester group-N of embodiment 3, N, and two (fluoroform sulfimide) salt of N-triethyl quaternary ammonium salt are ionic liquid.
Take Graphene as electrode materials, electrolytic solution used is 1mol/L LiTFSI/N-butylene carbonate ester group-N, N, and two (fluoroform sulfimide) salt of N-triethyl quaternary ammonium salt+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 N-butylene carbonate ester group-N, and N is in two (fluoroform sulfimide) salt of N-triethyl quaternary ammonium salt; 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 ion liquid of quaternaries of a carbonate-containing group, is characterized in that, it comprises following structural formula:
Figure FDA0000115155450000011
In formula, R is
Figure FDA0000115155450000012
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 ion liquid of quaternaries of a carbonate-containing group, is characterized in that, comprises the steps:
S1, be that 1: 1.1～1.2 triethylamine and RX carry out building-up reactions with mol ratio, make structural formula after reaction finishes and be
Figure FDA0000115155450000013
The quaternary ammonium halide of carbonate-containing group; Wherein, R is
Figure FDA0000115155450000014
0≤n≤4; X is halogen element;
Quaternary ammonium halide 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 FDA0000115155450000015
The ion liquid of quaternaries 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 ion liquid of quaternaries 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 ion liquid of quaternaries 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 ion liquid of quaternaries 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 ion liquid of quaternaries, 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 ion liquid of quaternaries 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 quaternary ammonium halide of described carbonate-containing group after finishing.
8. the preparation method of the ion liquid of quaternaries 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 ion liquid of quaternaries 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 ion liquid of quaternaries of carbonate-containing group to described after finishing.
The ion liquid of quaternaries of carbonate-containing group claimed in claim 1 in ultracapacitor or lithium ion battery as the application of electrolytic solution.
CN2011103931887A 2011-12-01 2011-12-01 Quaternary ammonium salt ionic liquid containing carbonic ester group and preparation method and application thereof Pending CN103130764A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113316570A (en) * 2019-01-18 2021-08-27 巴斯夫欧洲公司 Method for producing compounds having cyclic monothiocarbonate groups

Citations (2)

* 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
US20060210876A1 (en) * 2005-03-17 2006-09-21 Takashi Kuboki Electrochemical device

Patent Citations (2)

* 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
US20060210876A1 (en) * 2005-03-17 2006-09-21 Takashi Kuboki Electrochemical device

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113316570A (en) * 2019-01-18 2021-08-27 巴斯夫欧洲公司 Method for producing compounds having cyclic monothiocarbonate groups
US11897861B2 (en) 2019-01-18 2024-02-13 Basf Se Method for the preparation of compounds with cyclic monothiocarbonate groups

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Application publication date: 20130605