CN103138005A - Morpholines ionic liquid containing carbonic ester perssad and preparation method and application thereof - Google Patents

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

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CN103138005A
CN103138005A CN2011103933986A CN201110393398A CN103138005A CN 103138005 A CN103138005 A CN 103138005A CN 2011103933986 A CN2011103933986 A CN 2011103933986A CN 201110393398 A CN201110393398 A CN 201110393398A CN 103138005 A CN103138005 A CN 103138005A
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ionic liquid
carbonate
containing group
preparation
morpholine
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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 ionic liquid field and discloses a morpholines 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 morpholines 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 an 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 electrochemistry stability of the ionic liquid electrolyte solution can be improved.

Description

Morpholine class ionic 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 morpholine class ionic 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 designer, thereby ionic liquid is called as designer'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 electrolyte 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 stable temperature scope, preferably chemical stability and wider electrochemical stability potential window; (4) good dissolution characteristics all shows good solvability to a lot of inorganic matters and organic substance; (5) without ignition point 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 application studies.Ionic liquid is as the novel solvent of a class, medium, catalyst, and the research in fields such as organic synthesis, catalytic reaction, extract and separate, 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 morpholine class ionic liquid of novel carbonate-containing group.
A kind of morpholine class ionic liquid of carbonate-containing group, it comprises following structural formula:
Figure BDA0000115156720000021
In formula, R is
Figure BDA0000115156720000022
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 morpholine class ionic liquid of above-mentioned carbonate-containing group, comprise the steps:
S1, be that 1: 1.1～1.2 N-methylmorpholine and RX carry out synthetic reaction with mol ratio, make structural formula after reaction finishes and be
Figure BDA0000115156720000023
The morpholine halide of carbonate-containing group; Wherein, R is
Figure BDA0000115156720000024
0≤n≤4; X is halogen element, is selected from Cl or Br;
Morpholine halide and the inorganic salts MY of S2, described carbonate-containing group that step S1 is made carry out ion-exchange reactions according to the mol ratio of 1: 1, make structural formula after reaction finishes and are
Figure BDA0000115156720000025
The morpholine class ionic liquid of described carbonate-containing group; Wherein, in MY, M +For the ease of solubility cation, 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 synthetic reaction 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 synthetic reaction stirs 48～72h and carries out under 60～80 ℃.
The morpholine class ionic 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 electrolyte.
The morpholine class ionic liquid of carbonate-containing group provided by the invention by introduce carbonate group in cation, 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 electrolyte, this carbonic ester structure has good dissolving and the effect of dissociating to lithium salts; The ionic liquid that contains on the other hand the carbonic ester structure can generate SEI film (being solid-electrolyte interface film) preferably, thereby improves the electrochemical stability of il electrolyte.
The morpholine class ionic liquid preparation method of carbonate group provided by the invention, preparation technology is simple, is suitable for large-scale production production.
Description of drawings
Fig. 1 is preparation technology's flow chart of the morpholine class ionic 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 morpholine class ionic liquid of carbonate-containing group provided by the invention, it comprises following structural formula:
Figure BDA0000115156720000031
In formula, R is
Figure BDA0000115156720000032
0≤n≤4; Y -Be selected from BF 4 -, PF 6 -, (CF 3SO 2) 2N -Or CF 3SO 3 -
The preparation method of the morpholine class ionic liquid of above-mentioned carbonate-containing group as shown in Figure 1, comprises the steps:
S1, be that 1: 1.1～1.2 N-methylmorpholine and RX (being the halo carbonic ester) carry out synthetic reaction with mol ratio, make structural formula after reaction finishes and be
Figure BDA0000115156720000041
The morpholine halide morpholine halogen of carbonate-containing group (or be called) of carbonate-containing group; Wherein, R is
Figure BDA0000115156720000042
0≤n≤4; X is halogen element, is selected from Cl or Br; Its reaction equation is as follows:
Figure BDA0000115156720000043
Wherein, RX is
Figure BDA0000115156720000044
Be selected from chlorocarbonic acid vinyl acetate, chlorocarbonic acid propylene, chlorocarbonic acid butene esters, chlorocarbonic acid amylene ester, chlorocarbonic acid hexene ester, bromo ethylene carbonate, bromo propene 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;
Morpholine halide and the inorganic salts MY of S2, described carbonate-containing group that step S1 is made carry out ion-exchange reactions according to the mol ratio of 1: 1, make structural formula after reaction finishes and are
Figure BDA0000115156720000045
The morpholine class ionic liquid of described carbonate-containing group; Wherein, in MY, M +For the ease of solubility cation, 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 equation is as follows:
In above-mentioned preparation method, in step S1: synthetic reaction 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 synthetic reaction stirs 48～72h and carries out under 60～80 ℃.
In above-mentioned preparation method, the synthetic reaction in step S1 also comprises the halid purification step of the morpholine of carbonate-containing group after finishing:
Reactant liquor is standing cooling, then with the ethyl acetate washing repeatedly; 80 ℃ of lower vacuumizes, obtain lurid pure solid subsequently, i.e. the morpholine halide of carbonate-containing group;
In above-mentioned preparation method, the ion-exchange reactions in step S2 also comprises the purification step to the morpholine class ionic 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, carrene is concentrated with Rotary Evaporators, obtains colourless liquid after 80 ℃ of vacuumize 48h, is the morpholine class ionic liquid of carbonate-containing group.
The morpholine class ionic liquid of above-mentioned carbonate-containing group in ultracapacitor or lithium ion battery as the application of electrolyte.
The morpholine class ionic liquid of carbonate-containing group provided by the invention by introduce carbonate group in cation, improves the performance of ionic liquid, is containing lithium salts (LiBF on the one hand 4, LiPF 6, LiTFSI, (CF 3SO 2) 2NLi or CF 3SO 3Li) in electrolyte, this carbonic ester structure has good dissolving and the effect of dissociating to lithium salts; The ionic liquid that contains on the other hand the carbonic ester structure can generate SEI film (being solid-electrolyte interface film) preferably, thereby improves the electrochemical stability of il electrolyte.
The morpholine class ionic liquid preparation method of carbonate group provided by the invention, preparation technology is simple, is suitable for large-scale production production.
The below is described in further detail preferred embodiment of the present invention.
Synthesizing of embodiment 1 N-propylene carbonate ester group-N-methylmorpholine tetrafluoroborate
1, add respectively (101g, 1mol) N-methylmorpholine 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 synthetic reaction 72h; Standing cooling subsequently, wash product 3 times with ethyl acetate, and 80 ℃ of lower vacuumizes, obtain lurid N-propylene carbonate ester group-N-methylmorpholine villaumite, yield is 72%;
2, with the above-mentioned N-propylene carbonate ester group that makes-N-methylmorpholine villaumite (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 liquor; Then, mixed liquor 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 carrene was concentrated with Rotary Evaporators, 80 ℃ of vacuumize 48h obtained colourless liquid, are N-propylene carbonate ester group-N-methylmorpholine tetrafluoroborate ion liquid.
The nuclear magnetic resoance spectrum diagram data of N-propylene carbonate ester group-N-methylmorpholine tetrafluoroborate is as follows:
1H?NMR(CDCl 3，400MHz，ppm)：4.52(m，1H)，4.40(d，2H)，3.73(m，2H)，3.62(m，2H)，2.95(s，3H)，2.88(d，2H)，2.78(m，2H)，2.56(m，2H).
Synthesizing of embodiment 2 N-ethylene carbonate ester group-N-methylmorpholine hexafluorophosphates
1, add respectively (101g, 1mol) N-methylmorpholine and (182.6g, 1.1mol) bromo ethylene carbonate in the flask of 250mL; Then at Ar 2Under the atmosphere protection, be warming up to 80 ℃, stir synthetic reaction 48h; Standing cooling subsequently, with ethyl acetate washing 3 times, and 80 ℃ of lower vacuumizes, obtain lurid N-ethylene carbonate ester group-N-methylmorpholine bromine salt, yield is 74%;
2, with the above-mentioned N-ethylene carbonate ester group that makes-N-methylmorpholine bromine 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 reactions 24h; The reaction complete after, or mixed solution; Then, mixed liquor 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 carrene was concentrated with Rotary Evaporators, 80 ℃ of vacuumize 48h obtained colourless liquid, are N-ethylene carbonate ester group-N-methylmorpholine hexafluorophosphate ionic liquid.
Synthesizing of two (fluoroform sulfimide) salt of embodiment 3 N-butylene carbonate ester group-N-methylmorpholines
1, add respectively (101g, 1mol) N-methylmorpholine 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 vacuumizes, obtain lurid N-butylene carbonate ester group-N-methylmorpholine bromine salt, yield is 78%.
2, add (147.5g, 0.5mol) N-butylene carbonate ester group-N-methylmorpholine 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 mixed solution; Then, mixed liquor 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 carrene was concentrated with Rotary Evaporators, 80 ℃ of vacuumize 48h obtained colourless liquid, were two (fluoroform sulfimide) the salt ion liquid of N-butylene carbonate ester group-N-methylmorpholine.
Synthesizing of embodiment 4 N-carbonic acid amylene ester group-N-methylmorpholine fluoroform sulphonates
1, add respectively (101g, 1mol) N-methylmorpholine 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 vacuumizes, obtain lurid N-carbonic acid amylene ester group-N-methylmorpholine villaumite, yield is 77%.
2, add (131.5g, 0.5mol) N-carbonic acid amylene ester group-N-methylmorpholine 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 liquor 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.Carrene is concentrated with Rotary Evaporators, obtains colourless liquid after 80 ℃ of vacuumize 48h, is N-carbonic acid amylene ester group-N-methylmorpholine fluoroform sulphonate ionic liquid.
Synthesizing of embodiment 5 N-carbonic acid hexene ester group-N-methylmorpholine tetrafluoroborates
1, add respectively (101g, 1mol) N-methylmorpholine and (266.4g, 1.2mol) bromo carbonic acid hexene ester in the flask of 250mL.At N 2And Ar 2Form under the protection of mist atmosphere, be warming up to 60 ℃, stirring reaction 72h.Standing cooling, with ethyl acetate washing 3 times.80 ℃ of lower vacuumizes, obtain lurid N-carbonic acid hexene ester group-N-methylmorpholine bromine salt, yield is 79%.
2, add (161.5g, 0.5mol) N-carbonic acid hexene ester group-N-methylmorpholine 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 liquor 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.Carrene is concentrated with Rotary Evaporators, obtains colourless liquid after 80 ℃ of vacuumize 48h, is N-carbonic acid hexene ester group-N-methylmorpholine tetrafluoroborate ion liquid.
Embodiment 6
The present embodiment is take two (fluoroform sulfimide) salt of N-butylene carbonate ester group-N-methylmorpholine of embodiment 3 as ionic liquid.
Take Graphene as electrode material, electrolyte used is two (fluoroform sulfimide) salt of 1mol/L LiTFSI/N-butylene carbonate ester group-N-methylmorpholine+10wt.% acetonitrile, is assembled into button cell.The process for preparation of electrolyte: under nitrogen protection; LiTFSI (i.e. two (trimethyl fluoride sulfonyl) imine lithium) is joined in two (fluoroform sulfimide) salt of N-butylene carbonate ester group-N-methylmorpholine; stir, the concentration that makes LiTFSI is 1mol/L.Then, add the acetonitrile that accounts for gross 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 1.0A/g records its charging and discharging curve, as can be seen from Figure 2, the electrolyte 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 morpholine class ionic liquid of a carbonate-containing group, is characterized in that, it comprises following structural formula:
Figure FDA0000115156710000011
In formula, R is 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 morpholine class ionic liquid of a carbonate-containing group, is characterized in that, comprises the steps:
S1, be that 1: 1.1～1.2 N-methylmorpholine and RX carry out synthetic reaction with mol ratio, make structural formula after reaction finishes and be
Figure FDA0000115156710000013
The morpholine halide of carbonate-containing group; Wherein, R is 0≤n≤4; X is halogen element;
Morpholine halide and the inorganic salts MY of S2, described carbonate-containing group that step S1 is made carry out ion-exchange reactions according to the mol ratio of 1: 1, make structural formula after reaction finishes and are
Figure FDA0000115156710000015
The morpholine class ionic liquid of described carbonate-containing group; Wherein, in MY, M +Be the ease of solubility cation; Y -Be selected from BF 4 -, PF 6 -, (CF 3SO 2) 2N -Or CF 3SO 3 -
3. the preparation method of the morpholine class ionic 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 morpholine class ionic liquid of carbonate-containing group according to claim 2, is characterized in that, the synthetic reaction in step S1 is carried out under inert atmosphere.
5. the preparation method of the morpholine class ionic 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 morpholine class ionic liquid, it is characterized in that, in described step S1, described synthetic reaction stirs 48～72h and carries out under 60～80 ℃.
7. the preparation method of the morpholine class ionic liquid of carbonate-containing group according to claim 6, is characterized in that, the synthetic reaction in described step S1 also comprises the halid purification step of the morpholine of described carbonate-containing group after finishing.
8. the preparation method of the morpholine class ionic 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 morpholine class ionic liquid of according to claim 2 or 8 described carbonate-containing groups, it is characterized in that, ion-exchange reactions in described step S2 also comprises the purification step that contains the morpholine class ionic liquid of carbonate-containing group to described after finishing.
The morpholine class ionic liquid of carbonate-containing group claimed in claim 1 in ultracapacitor or lithium ion battery as the application of electrolyte.
CN2011103933986A 2011-12-01 2011-12-01 Morpholines ionic liquid containing carbonic ester perssad and preparation method and application thereof Pending CN103138005A (en)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102015666A (en) * 2008-04-29 2011-04-13 默克专利有限公司 Reactive ionic liquids

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102015666A (en) * 2008-04-29 2011-04-13 默克专利有限公司 Reactive ionic liquids

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* Cited by examiner, † Cited by third party
Title
TETSUYA TSUDA, ET AL.: "Design, Synthesis, and Electrochemistry of Room-Temperature Ionic Liquids Functionalized with Propylene Carbonate", 《ANGEWANDTE CHEMIE INTERNATIONAL EDITION》, vol. 50, 5 January 2011 (2011-01-05), pages 1310 - 1313 *

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Application publication date: 20130605