CN103130786B - Oxazolidine class ionic liquid of carbonate-containing group and its preparation method and application - Google Patents

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

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CN103130786B
CN103130786B CN201110393404.8A CN201110393404A CN103130786B CN 103130786 B CN103130786 B CN 103130786B CN 201110393404 A CN201110393404 A CN 201110393404A CN 103130786 B CN103130786 B CN 103130786B
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ionic liquid
carbonate
oxazolidine
containing group
liquid
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CN103130786A (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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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Electric Double-Layer Capacitors Or The Like (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention belongs to field of ionic liquid, oxazolidine class ionic liquid that it discloses a kind of carbonate-containing group and its preparation method and application；This ionic liquid has a following structural formula:In formula, R is0≤n≤4；Y‑Selected from BF4 ‑、PF6 ‑、(CF3SO2)2N‑Or CF3SO3 ‑.The oxazolidine class ionic liquid of the carbonate-containing group that the present invention provides, by introducing carbonate group in cation, the performance making ionic liquid is improved, and on the one hand in the electrolyte containing lithium salts, this structural carbonate has good dissolving and dissociation to lithium salts；On the other hand the ionic liquid containing structural carbonate can preferably generate SEI film, thus improves the electrochemical stability of il electrolyte.

Description

Oxazolidine class 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 oxazolidine class ionic liquid and the system thereof of a kind of carbonate-containing group Preparation Method and application.
Background technology
Ionic liquid (Ionic liquids) refers to that (generally less than 100 DEG C) are in a liquid state, by organic in the range of room temperature Cation and inorganic anion (or organic anion) are constituted.Ionic liquid has adjustability, needs to change it according to difference Zwitterion structure can reach the purpose of designer, thus ionic liquid is referred to as the solvent of designer.As far back as 1914 just It is found that first ionic liquid----nitro ethamine；But thereafter, the progress in this field is slow.Until 1992, Wikes The research group of leader has synthesized low melting point, resistant to hydrolysis, 1-ethyl-3-methylimidazole tetrafluoroborate ionic liquid that stability is strong Body ([EMIM] BF4After), the research of ionic liquid is just developed rapidly, has been subsequently developed that were a series of ionic liquid body System.Initial ionic liquid is mainly used in electrochemical research, and ionic liquid is used for organic and high score as green solvent in recent years Son synthesis comes into one's own.Compared with traditional organic solvent and electrolyte, ionic liquid has a series of prominent advantage: (1) Fusing point is below or near to room temperature, the temperature range width being in a liquid state；(2) steam force down, hardly volatilization, colourless, odorless；(3) tool There are bigger equilibrium temperature scope, preferable chemical stability and wider electrochemically stable potential window；(4) good dissolving A lot of inorganic matters and Organic substance are all shown good solvability by characteristic；(5) without ignition point and nonflammable；(6) can follow Ring uses, free from environmental pollution etc..
At present, the research to ionic liquid is concentrated mainly on the synthesis of novel ion liquid, ionic liquid physics and chemistry Characterizing and as the aspect such as applied research of solvent and electrolyte of characteristic.Ionic liquid is as the novel solvent of a class, Jie Matter, catalyst, prepare at organic synthesis, catalytic reaction, extract and separate, material, the research in the field such as natural polymer, electrochemistry Achieve many gratifying results, of great interest.
Summary of the invention
Based on the problems referred to above, an object of the present invention be the oxazolidine class that a kind of novel carbonate-containing group is provided from Sub-liquid.
A kind of oxazolidine class ionic liquid of carbonate-containing group, it includes following structural formula:
In formula, R is0≤n≤4；Y-Selected from BF4 -、PF6 -、(CF3SO2)2N-Or CF3SO3 -。
Another object of the present invention is to provide the preparation method of the oxazolidine class ionic liquid of above-mentioned carbonate-containing group, bag Include following steps:
S1, with RX, N-methyl oxazolidine that mol ratio is 1: 1.1～1.2 being carried out synthetic reaction, reaction prepares knot after terminating Structure formula isThe N-methyl oxazolidine halogenide of carbonate-containing group；Wherein, R is0≤n≤4；X is Halogen element, selected from Cl or Br；
S2, the N-methyl oxazolidine halogenide of described carbonate-containing group step S1 prepared and inorganic salt MY are according to 1: 1 Mol ratio carry out ion-exchange reactions, reaction prepares structural formula after terminating and isThe azoles of described carbonate-containing group Alkanes ionic liquid；Wherein, in MY, M+For ease of solubility cation, selected from Na+、K+Or NH4 +；Y-Selected from BF4 -、PF6 -、 (CF3SO2)2N-Or CF3SO3 -。
In above-mentioned preparation method, the synthetic reaction in step S1 is carried out in an inert atmosphere；This inert atmosphere is bag Include and be made up of at least one gas in nitrogen and argon；In described step S1, described synthetic reaction is to stir at 60～80 DEG C 48～72h are carried out.
A further object of the present invention is that the oxazolidine class ionic liquid providing above-mentioned carbonate-containing group is at ultracapacitor Or as the application of electrolyte in lithium ion battery.
The oxazolidine class ionic liquid of the carbonate-containing group that the present invention provides, by introducing carbonate group in cation Group, makes the performance of ionic liquid be improved, on the one hand containing lithium salts (e.g., LiBF4、LiPF6、LiTFSI、(CF3SO2)2NLi or CF3SO3Li), in electrolyte, this structural carbonate has good dissolving and dissociation to lithium salts；On the other hand containing carbon The ionic liquid of acrylate structure can preferably generate SEI film (i.e. solid-electrolyte interface film), thus improves ionic liquid electricity Solve the electrochemical stability of liquid.
The oxazolidine class ionic liquid preparation method of the carbonate group that the present invention provides, preparation technology is simple, is suitable for big Scale production produces.
Accompanying drawing explanation
Fig. 1 is the preparation technology flow chart of the oxazolidine class ionic liquid of the 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 preparation.
Detailed description of the invention
The oxazolidine class ionic liquid of carbonate-containing group that the present invention provides, it includes following structural formula:
In formula, R is0≤n≤4；Y-Selected from BF4 -、PF6 -、(CF3SO2)2N-Or CF3SO3 -。
The preparation method of the oxazolidine class ionic liquid of above-mentioned carbonate-containing group, as it is shown in figure 1, comprise the steps:
S1, N-methyl oxazolidine that mol ratio is 1: 1.1～1.2 is carried out synthetic reaction, instead with RX (i.e. halocarbonate) Should prepare structural formula after terminating isN-methyl oxazolidine halogenide (or the referred to as carbonate-containing base of carbonate-containing group The N-methyl oxazolidine halogen of group)；Wherein, R is0≤n≤4；X is halogen element, selected from Cl or Br；Its reaction equation As follows:
Wherein, RX isSelected from chlorocarbonic acid vinyl acetate, chlorocarbonic acid propylene, chlorocarbonic acid butene esters, Chlorocarbonic acid amylene ester, chlorocarbonic acid hexene ester, bromo ethylene carbonate, bromo Allyl carbonate, bromo butylene, bromine For carbonic acid amylene ester or bromo carbonic acid hexene ester etc.；When n is 0, it is simply that chlorocarbonic acid vinyl acetate；When n is 4, it it is chlorocarbonic acid Hexene ester；Remaining, analogize；
S2, the N-methyl oxazolidine halogenide of described carbonate-containing group step S1 prepared and inorganic salt MY are according to 1: 1 Mol ratio carry out ion-exchange reactions, reaction prepares structural formula after terminating and isThe azoles of described carbonate-containing group Alkanes ionic liquid；Wherein, in MY, M+For ease of solubility cation, selected from Na+、K+Or NH4 +；Y-Selected from BF4 -、PF6 -、 (CF3SO2)2N-Or CF3SO3 -；Its reaction equation is as follows:
In above-mentioned preparation method, in step S1: synthetic reaction is carried out in an inert atmosphere；This inert atmosphere is to include The inert atmosphere being made up of the arbitrary gas of nitrogen or argon, and described synthetic reaction is to stir 48～72h to enter at 60～80 DEG C Row.
In above-mentioned preparation method, after the synthetic reaction in step S1 terminates, also include the oxazolidine halogen to carbonate-containing group The purification step of compound:
Reactant liquor is stood cooling, then washs repeatedly by ethyl acetate；It is vacuum dried at 80 DEG C subsequently, obtains pale yellow The oxazolidine halogenide of the neat solid of color, i.e. carbonate-containing group；
In above-mentioned preparation method, after the ion-exchange reactions in step S2 terminates, also include the azoles to carbonate-containing group The purification step of alkanes ionic liquid:
Reaction mixture 250mL dichloromethane extracts repeatedly, combining extraction liquid；Every time the most straight with deionized water back extraction Extremely with saturated AgNO3Till aqueous solution titration aqueous phase produces without precipitation；Then, dichloromethane Rotary Evaporators concentrates, Obtain colourless liquid after 80 DEG C of vacuum drying 48h, be the oxazolidine class ionic liquid of carbonate-containing group.
The oxazolidine class ionic liquid of above-mentioned carbonate-containing group in ultracapacitor or lithium ion battery as electrolyte Application.
The oxazolidine class ionic liquid of the carbonate-containing group that the present invention provides, by introducing carbonate group in cation Group, makes the performance of ionic liquid be improved, on the one hand containing lithium salts (e.g., LiBF4、LiPF6、LiTFSI、(CF3SO2)2NLi or CF3SO3Li), in electrolyte, this structural carbonate has good dissolving and dissociation to lithium salts；On the other hand containing carbon The ionic liquid of acrylate structure can preferably generate SEI film (i.e. solid-electrolyte interface film), thus improves ionic liquid electricity Solve the electrochemical stability of liquid.
The oxazolidine class ionic liquid preparation method of the carbonate group that the present invention provides, preparation technology is simple, is suitable for big Scale production produces.
Below presently preferred embodiments of the present invention is described in further detail.
The synthesis of embodiment 1 N-propylene carbonate ester group-N-methyl oxazolidine tetrafluoroborate
1, in the flask of 250mL, it is separately added into (87g, 1mol) N-methyl oxazolidine and (149.6g, 1.1mol) chloro carbon Acid propylene ester；Then at N2Under atmosphere protection, it is warming up to 60 DEG C, stirs synthetic reaction 72h；Stand cooling subsequently, use acetic acid second Ester washing product 3 times, and be vacuum dried at 80 DEG C, obtain lurid N-propylene carbonate ester group-N-methyl oxazolidine villaumite, Yield is 75%；
2, by above-mentioned prepared N-propylene carbonate ester group-N-methyl oxazolidine villaumite (111.5g, 0.5mol), NaBF4(or KBF4) (55g, 0.5mol) and 100mL deionized water add in the flask of 500mL, is stirred at room temperature reaction 10h；React Cheng Hou, it is thus achieved that mixed liquor；Then, mixed liquor 250mL dichloromethane extracts 3 times, combining extraction liquid；The most each 60mL goes Ionized water back extraction is until with saturated AgNO3Till aqueous solution titration aqueous phase produces without precipitation；Dichloromethane uses rotary evaporation mutually After instrument concentrates, 80 DEG C of vacuum drying 48h obtain colourless liquid, are N-propylene carbonate ester group-N-methyl oxazolidine Tetrafluoroboric acid Ionic liquid.
The nuclear magnetic resoance spectrum diagram data of N-propylene carbonate ester group-N-methyl oxazolidine tetrafluoroborate is as follows:
1H NMR(CDCl3, 400MHz, ppm): 4.83 (s, 2H), 4.72 (m, 1H), 4.40 (d, 2H), 3.82 (m, 2H), 3.73 (d, 2H), 3.41 (m, 2H), 3.29 (s, 3H).
The synthesis of embodiment 2 N-ethylene carbonate ester group-N-methyl oxazolidine hexafluorophosphate
1, in the flask of 250mL, it is separately added into (87g, 1mol) N-methyl oxazolidine and (182.6g, 1.1mol) bromo carbon Vinyl acetate；Then at Ar2Under atmosphere protection, it is warming up to 80 DEG C, stirs synthetic reaction 48h；Stand cooling subsequently, use acetic acid second Ester washs 3 times, and is vacuum dried at 80 DEG C, obtains lurid N-ethylene carbonate ester group-N-methyl oxazolidine bromide, and yield is 74%；
2, by above-mentioned prepared N-ethylene carbonate ester group-N-methyl oxazolidine bromide (126.5g, 0.5mol), KPF6(92g, 0.5mol) add in 500mL flask with 150mL deionized water, be stirred at room temperature ion-exchange reactions 24h；After having reacted, Or mixed solution；Then, mixed liquor 250mL dichloromethane extracts 3 times, combining extraction liquid；The most each 60mL go from Sub-water back extraction is until with saturated AgNO3Till aqueous solution titration aqueous phase produces without precipitation；Dichloromethane uses Rotary Evaporators mutually After concentration, 80 DEG C of vacuum drying 48h obtain colourless liquid, are N-ethylene carbonate ester group-N-methyl oxazolidine hexafluorophosphate Ionic liquid.
The synthesis of double (fluoroform sulfimide) salt of embodiment 3N-butylene carbonate ester group-N-methyl oxazolidine
1, in the flask of 250mL, it is separately added into (87g, 1mol) N-methyl oxazolidine and (213.4g, 1.1mol) bromo carbon Acid butene esters.At N2Under atmosphere protection, it is warming up to 65 DEG C, stirring reaction 60h；Stand cooling, wash 3 times by ethyl acetate.? Being vacuum dried at 80 DEG C, obtain lurid N-butylene carbonate ester group-N-methyl oxazolidine bromide, yield is 78%.
2, in 500mL flask add (140.5g, 0.5mol) N-butylene carbonate ester group-N-methyl oxazolidine bromide, (159.5g, 0.5mol) fluoroform sulfimide potassium (CF3SO2)2NK and 120mL deionized water, is stirred at room temperature reaction 12h. After having reacted, it is thus achieved that mixed solution；Then, mixed liquor 250mL dichloromethane extracts 3 times, combining extraction liquid；The most each With 60mL deionized water back extraction until with saturated AgNO3Till aqueous solution titration aqueous phase produces without precipitation；Dichloromethane is used mutually After Rotary Evaporators concentrates, 80 DEG C of vacuum drying 48h obtain colourless liquid, are N-butylene carbonate ester group-N-methyl oxazolidine Double (fluoroform sulfimide) ionic liquid.
The synthesis of embodiment 4 N-carbonic acid amylene ester group-N-methyl oxazolidine fluoroform sulphonate
1, in the flask of 250mL, it is separately added into (87g, 1mol) N-methyl oxazolidine and (196.8g, 1.2mol) chloro carbon Acid amylene ester.At N2Under atmosphere protection, it is warming up to 70 DEG C, stirring reaction 50h；Stand cooling, wash 3 times by ethyl acetate；? Being vacuum dried at 80 DEG C, obtain lurid N-carbonic acid amylene ester group-N-methyl oxazolidine villaumite, yield is 77%.
2, in a 250mL flask add (124.5g, 0.5mol) N-carbonic acid amylene ester group-N-methyl oxazolidine villaumite, (86g, 0.5mol) CF3SO3Na and 140mL deionized water, is stirred at room temperature reaction 18h.After having reacted, mixed liquor is used 250mL dichloromethane extracts 3 times, combining extraction liquid；The most every time with 60mL deionized water back extraction until with saturated AgNO3Water Till solution titration aqueous phase produces without precipitation.Dichloromethane Rotary Evaporators concentrates, and obtains nothing after 80 DEG C of vacuum drying 48h The liquid of color, is N-carbonic acid amylene ester group-N-methyl oxazolidine trifluoromethanesulfonic acid ionic liquid.
The synthesis of embodiment 5 N-carbonic acid hexene ester group-N-methyl oxazolidine tetrafluoroborate
1, in the flask of 250mL, it is separately added into (87g, 1mol) N-methyl oxazolidine and (266.4g, 1.2mol) bromo carbon Acid hexene ester.At N2And Ar2Under composition mixed gas atmosphere protection, it is warming up to 60 DEG C, stirring reaction 72h.Stand cooling, use second Acetoacetic ester washs 3 times.It is vacuum dried at 80 DEG C, obtains lurid N-carbonic acid hexene ester group-N-methyl oxazolidine bromide, yield It is 79%.
2, in a 250mL flask add (154.5g, 0.5mol) N-carbonic acid hexene ester group-N-methyl oxazolidine bromide, (52.5g, 0.5mol) NH4BF4With 130mL deionized water, it is stirred at room temperature reaction 15h；After having reacted, mixed liquor is used 250mL dichloromethane extracts 3 times, combining extraction liquid；The most every time with 60mL deionized water back extraction until with saturated AgNO3Water Till solution titration aqueous phase produces without precipitation.Dichloromethane Rotary Evaporators concentrates, and obtains nothing after 80 DEG C of vacuum drying 48h The liquid of color, is N-carbonic acid hexene ester group-N-methyl oxazolidine tetrafluoroborate ion liquid.
Embodiment 6
The present embodiment with double (fluoroform sulfimide) salt of the N-butylene carbonate ester group-N-methyl oxazolidine of embodiment 3 for from Sub-liquid.
With Graphene as electrode material, electrolyte used is 1mol/L LiTFSI/N-butylene carbonate ester group-N-methyl azoles Double (fluoroform sulfimide) salt+10wt.% acetonitrile of alkane, is assembled into button cell.
The process for preparation of electrolyte: under nitrogen protection, adds LiTFSI (i.e. two (trimethyl fluoride sulfonyl) imine lithium) In double (fluoroform sulfimide) salt of N-butylene carbonate ester group-N-methyl oxazolidine, stirring, the concentration making LiTFSI is 1mol/L.Then, in system, add the acetonitrile accounting for gross mass 10%, and be uniformly mixed.
Utilize CHI660A electrochemical workstation that it is carried out constant current charge-discharge test, at the electrochemical window of 0～2.7V In, record its charging and discharging curve with the electric current of 0.25A/g, figure it is seen that the electrolyte that the embodiment of the present invention is prepared exists Up in the charging voltage of 2.7V, there is preferable cyclical stability.
It should be appreciated that the above-mentioned statement for present pre-ferred embodiments is more detailed, can not therefore think Being the restriction to scope of patent protection of the present invention, the scope of patent protection of the present invention should be as the criterion with claims.

Claims (3)

1. the oxazolidine class ionic liquid of a carbonate-containing group, it is characterised in that it includes following structural formula:
In formula, R isN=2；Y-For (CF3SO2)2N-。
2. the preparation method of the oxazolidine class ionic liquid of a carbonate-containing group, it is characterised in that comprise the steps:
S1, the N-methyl oxazolidine being separately added into 1mol in the flask of 250mL and the bromo butylene of 1.1mol, at N2Atmosphere Enclose under protection, be warming up to 65 DEG C, stirring reaction 60h；Stand cooling, wash 3 times by ethyl acetate, be vacuum dried at 80 DEG C, Obtain lurid N-butylene carbonate ester group-N-methyl oxazolidine bromide；
S2, in 500mL flask, add the N-butylene carbonate ester group-N-methyl oxazolidine bromide of 0.5mol, the fluoroform of 0.5mol Sulfimide potassium and 120mL deionized water, be stirred at room temperature reaction 12h；After having reacted, it is thus achieved that mixed solution；Then, mixed Close liquid 250mL dichloromethane to extract 3 times, combining extraction liquid；The most every time with 60mL deionized water back extraction until with saturated AgNO3Till aqueous solution titration aqueous phase produces without precipitation；After dichloromethane concentrates with Rotary Evaporators, 80 DEG C of vacuum drying 48h obtains colourless liquid, is double (the fluoroform sulphonyl of N-butylene carbonate ester group-N-methyl oxazolidine with following structural formula Imines) ionic liquid:
In formula, R isN=2；Y-For (CF3SO2)2N-。
3. the oxazolidine class ionic liquid of the carbonate-containing group described in claim 1 is made in ultracapacitor or lithium ion battery Application for electrolyte.
CN201110393404.8A 2011-12-01 2011-12-01 Oxazolidine class ionic liquid of carbonate-containing group and its preparation method and application Expired - Fee Related CN103130786B (en)

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