CN101747213A - Ionic liquid taking diether quaternary ammonium as cation and synthetic method thereof - Google Patents
Ionic liquid taking diether quaternary ammonium as cation and synthetic method thereof Download PDFInfo
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- CN101747213A CN101747213A CN200810189017A CN200810189017A CN101747213A CN 101747213 A CN101747213 A CN 101747213A CN 200810189017 A CN200810189017 A CN 200810189017A CN 200810189017 A CN200810189017 A CN 200810189017A CN 101747213 A CN101747213 A CN 101747213A
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Abstract
The invention belongs to quaternary ammonium ionic liquid with low viscosity and low melting point. The structure formula of the ionic liquid is represented by formula (I). The invention comprises the following steps: taking secondary amine and halogenether as raw material, generating diether quaternary ammonium ionic liquid with anion being halogen through the synthesis and quaternization of tertiary amine containing ether bond, and then obtaining ionic liquid containing different anions through ion exchange. The ionic liquid generally is liquid under room temperature, and the curing temperature of part of ionic liquid is even lower than 90 DEG C below zero. The invention provides a selectable way for developing ionic liquid with low viscosity, and in addition, the cost of raw material is lower, the operation is simple and the yield is high.
Description
Technical field
The present invention relates to a kind of low viscous diether quaternary ammonium ionic liquid and synthetic method thereof, belong to new chemical material and preparing technical field thereof.
Background technology
Ionic liquid is meant fully by the yin, yang ion and constitutes that fusing point is usually less than 100 ℃ organic molten salt.To constituting the basic demand of ion liquid yin, yang ionic be: electric charge degree of scatter height, symmetry is poor, and molecular size is moderate.Only in this way, could reduce the interionic interaction force of yin, yang, weaken interionic and get in order and pile up, not hinder the ionic migration simultaneously again, thereby make ionic liquid show the characteristics that low melting point, low viscosity, high electricity are led etc.Because do not contain electroneutral molecule in the system, ionic liquid is non-volatile, and is also incombustible, it is wide to have the liquid journey simultaneously, Heat stability is good, feature such as electrochemical window is wide, and the higher and designability of specific conductivity is strong.Therefore, since the nineties in last century, ionic liquid has obtained the especially extensive approval of chemist of scientists as " green solvent ", is the potential substitute of traditional volatile organic solvent.Moreover, ion liquid These characteristics makes its range of application exceed traditional organic solvent from far away, for example, as dielectric medium, as the stratographic stationary phase, and can be applicable to ultrahigh vacuum(HHV) operation etc.
Can trace back to 1914 about ion liquid research, the first nitric acid ethylamine of synthetic ionic liquid fusing point was at 12 ℃ at that time.1948, people such as Hurley can be referred to as first-generation ionic liquid at room temperature in having reported aluminum chloride and the ethyl-magnesium-halide pyridine ion liquid that is mainly used in field of electroplating.Early 1980s, people such as Wilkes find 1, and 3-dialkylimidazolium chloro-aluminate has more negative electrochemical reduction current potential than N-Fixanol, and has synthesized 1 on this basis, 3-dialkylimidazolium chlorine aluminic acid class ionic liquid has further expanded ion liquid kind.In the eighties in 20th century, Seddon and Hussey etc. is used as chlorine aluminic acid ionic liquid as the non-aqueous polar solvent of a class, studies different transition metal complexes electrochemical behavior, fluorescent property and chemical reaction etc. therein.But this class ionic liquid is unfavorable for using widely to the water and air sensitivity.The rise of ionic liquid research appears at the beginning of the nineties, and at that time, United States Air Force research institute had reported a class with 1, and 3-dialkylimidazolium a tetrafluoro borate or hexafluorophosphate are the ionic liquid to water, air-stable of representative, can be described as s-generation ionic liquid.The ion liquid appearance of the s-generation makes ion liquid research and range of application be able to rapid expansion, all closely combines with ionic liquid as fields such as synthetic, the extracting and separating of catalysis, organic synthesis, nano material, electrochemistry.The proposition of functionalized ion liquid notion is the abundant of ionic liquid kind, optionally increase and range of application widen the thought motive that provides new.This class ionic liquid is called as third generation ionic liquid, the main functional group that introduces on zwitterion as special purpose.But the introducing of functional group often causes that ion liquid fusing point rises, and viscosity raises, and stability reduces, and therefore, its range of application is greatly limited.
Compare with dialkylimidazolium class ionic liquid, relatively cheap based on the ionic liquid price of quaternary ammonium cation, chemistry and electrochemical stability are better, but because viscosity is higher, have limited its practical application.It is reported, replace alkane chain (monoether base quaternary ammonium ion liquid), can not only reduce the fusing point of quaternary ammonium ion liquid, can also reduce viscosity effectively, improve specific conductivity, and to other physico-chemical property such as thermostability, the electrochemical stability influence is little with ether.By introducing ether, the improved while of the performance of quaternary ammonium ion liquid, it is too high that price also is unlikely to, and be that cationic ionic liquid is not seen bibliographical information at present with diether quaternary ammonium.
Summary of the invention
The object of the invention be to provide a kind of low viscous be anion ion liquid with the diether quaternary ammonium, and provide this ion liquid synthetic method.
The present invention introduces two ehter bonds at the quaternary ammonium cation center, having formed a class is positively charged ion with the diether quaternary ammonium, with chlorine, and bromine, tetrafluoroborate, hexafluoro-phosphate radical, nitrate radical, perchlorate, the methane sulfate radical, the ethane sulfate radical, Dyhard RU 100, two-(trifluoromethane sulphonyl)-imido grpup are anionic novel low viscosity ionic liquid.
Provided by the invention is that cationic ion liquid structural formula is represented with formula (I) with bis ether key quaternary ammonium:
N is 1 to 5 integer in formula (I) ionic liquid, and m is 1 to 5 integer; R
1, R
2, R
3, R
4Get CH independently of one another
3, CH
2CH
3, CH
2CH
2CH
3, CH
2CH
2CH
2CH
3Perhaps CH
2CH
2CH
2CH
2CH
3In a kind of;
Negatively charged ion X in formula (I) ionic liquid
-Be [Cl]
-, [Br]
-, [BF
4]
-, [PF
6]
-, [NO
3]
-, [ClO
4]
-, [CH
3OSO
3]
-, [C
2H
5OSO
3]
-, [N (CN)
2]
-, [(CF
3SO
2)
2N]
-In a kind of.
Described ion liquid characteristics are that its quaternary ammonium cation center is connected with two ehter bonds that can reduce viscosity, can be described as " diether quaternary ammonium ionic liquid ".
Among the present invention, the ionic liquid of representative with the diether quaternary ammonium is cation group has:
(1) .N, N-dimethyl-N, N-two (2-methoxy ethyl) quaternary ammonium Dyhard RU 100 salt ([N
11,1O2,1O2]
+[N (CN)
2]
-)
Fusing point is-18 ℃, and second-order transition temperature is-84 ℃; Under 25 ℃, its density is 1.07g/ml, and viscosity is 62cP, and electricity is led and is that 4.9mS/cm, electrochemical window are 4.3V (glass-carbon electrode).
(2) .N, N-dimethyl-N, N-two (2-methoxy ethyl) quaternary ammonium is two-(trifluoromethane sulphonyl)-imido grpup salt ([N
11,1O2,1O2]
+[NTF
2]
-)
No fusing point, second-order transition temperature are one 82 ℃; Under 25 ℃, its density is 1.42g/ml, and viscosity is 67cP, and electricity is led and is that 2.5mS/cm, electrochemical window are 5.5V (glass-carbon electrode).
(3) .N, N-dimethyl-N, N-two (2-methoxy ethyl) quaternary ammonium a tetrafluoro borate ([N
11,1O2,1O2]
+[BF
4]
-)
36 ℃ of fusing points; Under 25 ℃, its density is 1.21g/ml, and viscosity is 338cP, and electricity is led and is that 1.0mS/cm, electrochemical window are 5.4V (glass-carbon electrode).
It is raw material that the present invention adopts secondary amine and halogen ether, passes through the synthetic and quaternized of ether-containing key tertiary amine, and generating negatively charged ion is the diether quaternary ammonium ionic liquid of halogen, then by ion-exchange, obtains containing the ionic liquid of different anions.
Provided by the invention is that cationic ion liquid synthesis step is as follows with bis ether key quaternary ammonium:
In the formula (II), step (1) is the tertiary amine that feedstock production contains an ether with halogen ether and secondary amine;
In the formula (II), the diether quaternary ammonium haloid of step (2) gained is raw material with the ether tertiary amine with corresponding halogen ether;
In the formula (II), step (3) is a triethyl oxygen a tetrafluoro borate in order to the material of ion-exchange, methyl-sulfate, ethyl sulfate, dicyandiamide sodium, Potassium Hexafluorophosphate SODIUMNITRATE, SODIUMNITRATE, a kind of in sodium perchlorate or two-(trifluoromethane the sulphonyl)-imido grpup lithium.
In the formula (II), the mol ratio of step (1) halogen ether and secondary amine is 1: 2～1: 3.
In the formula (II), step (2) diether quaternary ammonium haloid is 1: 1～1: 1.2 with the mol ratio of ether tertiary amine and halogen ether.
Of the present invention all with the diether quaternary ammonium be the ionic liquid of cation group all pass through infrared spectra (IR), proton nmr spectra (
1H-NMR), carbon-13 nmr spectra (
13C-NMR), structural characterization and affirmation are carried out in mass spectrum (MS) and ultimate analysis.All ion liquid fusing points and second-order transition temperature are measured with the differential scanning calorimeter DSC Q100 of U.S. TA company.Density of liquid adopts weighting method to measure with the standard capacity bottle down at 25 ℃, electrochemical window is measured with U.S. CHI660A electrochemical workstation, 25 ℃ of mensuration, specific conductivity uses Mettler-Toledo Seven Mulitimeter 25 ℃ of mensuration to absolute viscosity with StabingerViscosimeter SVM 3000/GR.
Of the present invention is that the ionic liquid of cation group has viscosity and the specific conductivity suitable with dialkylimidazolium class ionic liquid with the diether quaternary ammonium, and the ion liquid electrochemical window that with the diether quaternary ammonium is cation group far is wider than dialkylimidazolium class ionic liquid, can be used as liquid electrolyte and is used for electrochemical research.The present invention introduces two high ethers of rotary freedom in the quaternary ammonium salt cationic simultaneously, compares with the tetraalkyl quaternary ammonium or the monoether based quaternary ammonium salt of structural similitude, be that the ionic liquid of cation group has following characteristics with the diether quaternary ammonium:
1. described ionic liquid has lower solidification value.
2. described ionic liquid has lower viscosity and the specific conductivity of Geng Gao.
3. described ionic liquid has the electrochemical window of working as with tetraalkyl quaternary ammonium ion liquid phase, can be used as liquid electrolyte and is used for electrochemical device.
4. the present invention is the ion liquid synthetic alternative approach of having developed of low viscosity.
Embodiment
In order to further specify details of the present invention, enumerate some embodiment below, but should not be so limited.
Embodiment 1:N, N-dimethyl N-(2-methoxy ethyl) amine (N
11,1O2) synthetic
278g (2.0 moles) 2-bromotrifluoromethane methyl ether is added dropwise to the dimethylamine agueous solution (containing 5.0 moles of dimethylamine) of (12 hours) 684g 33% under 30 ℃, after dropwising, temperature of reaction is risen to 40 ℃, stop behind the 12h.Add 2.0 moles of NaOH with the acid that neutralization generates, add an amount of NaCl and make it into saturated solution.80～90 ℃ of cuts are collected in air distillation, successively use CaCl
2With the KOH drying, all use (3 * 100ml) anhydrous diethyl ethers flushing during filtration.96～98 ℃ of cuts are collected in air distillation once more, get product N, N-dimethyl-N-(2-methoxy ethyl) amine (N
11,1O2) 129g, productive rate 63%.
Embodiment 2:N, N-dimethyl-N-methoxymethyl-N-(2-methoxy ethyl) quaternary ammonium villaumite ([N
11,1O1,1O2]
+[Cl]
-) synthetic
Under condition of ice bath,, 0.80 mole of (60.8ml) chloromethyl methyl ether slowly is added dropwise to contains 0.80 mole of (82.5g) N by 1: 1 mol ratio
11,1O2With the mixed solution of 100ml methylene dichloride, then 30 ℃ of reactions 4 hours (reaction system palpus connection drying tube is with the moisture in the secluding air) down.50 ℃ of removal of solvent under reduced pressure get weak yellow liquid [N
11,1O1,1O2]
+[Cl]
-147g, productive rate＞99%.
Embodiment 3:N, N-dimethyl-N, N-two (2-methoxy ethyl) quaternary ammonium villaumite ([N
11,1O2,1O2]
+[Cl]
-) synthetic
With 0.80 mole of (82.5g) N
11,1O2Add in the sealed reaction jar with 0.8 mole of (76g) 2-chloroethyl methyl ether and 80ml dehydrated alcohol, 120 ℃ were reacted 48 hours.After the taking-up, molecular impurity is removed in 70 ℃ of decompressions, gets white solid [N
11,1O2,1O2]
+[Cl]
-168g, productive rate: 85%.
Embodiment 4:[N
11,1O2,1O2]
+[Br]
-Synthetic
With 0.80 mole of (82.5g) N
11,1O2Add in the 500ml round-bottomed flask with 0.8 mole of (111g) 2-bromotrifluoromethane methyl ether and 120ml dehydrated alcohol, 40 ℃ were reacted 48 hours.Molecular impurity is removed in 70 ℃ of decompressions, and recrystallization in acetone gets white solid [N again
11,1O2,1O2]
+[Br]
-188g, productive rate: 90%.
Embodiment 5:[N
11,1O2,1O2]
+[N (CN)
2]
-Synthetic
1: 1.1 in molar ratio, take by weighing 0.25 mole of (60.5g) [N
11,1O2,1O2]
+[Br]
-Soluble in water, add 0.275 mole of (47.8g) AgN (CN) subsequently
2, magnetic agitation 2h filters, with (twice, 70 ℃ of decompression of water flushing of 2 * 100ml) gets weak yellow liquid [N to remove moisture
11,1O2,1O2]
+[N (CN)
2]
-48.5g, productive rate: 85%.
Embodiment 6:[N
11,1O2,1O2]
+[PF
6]
-Synthetic
1: 1.2 in molar ratio, get 0.25 mole of (49.4g) [N
11,1O2,1O2]
+[Cl]
-, 0.30 mole of (50.4g) NaPF
6And 100ml acetone adds in the 250ml round-bottomed flask mechanical stirring 48 hours.Filter, with (3 * 50ml) acetone rinsing three times, 70 ℃ of decompressions get product [N to remove acetone
11,1O2,1O2]
+[PF
6]
-82g, productive rate: 89%.
Embodiment 7:[N
11,1O2,1O2]
+[NO
3]
-Synthetic
1: 1.2 in molar ratio, get 0.25 mole of (49.4g) [N
11,1O2,1O2]
+[Cl]
-, 0.30 mole of (25.5g) NaNO
3And 100ml acetone adds in the 250ml round-bottomed flask mechanical stirring 48 hours.Filter, with (3 * 50ml) acetone rinsing three times, 70 ℃ of decompressions get product [N to remove acetone
111O2,1O2]
+[NO
3]
-34.6g, productive rate: 85%.
Embodiment 8:[N
11,1O2,1O2]
+[ClO
4]
-Synthetic
1: 1.2 in molar ratio, get 0.25 mole of (49.4g) [N
11,1O2,1O2]
+[Cl]
-, 0.30 mole of (36.7g) NaClO
4And 100ml acetone adds in the 250ml round-bottomed flask mechanical stirring 48 hours.Filter, with (3 * 50ml) acetone rinsing three times, 70 ℃ of decompressions get product [N to remove acetone
11,1O2,1O2]
+[ClO
4]
-56.3g, productive rate: 86%.
Embodiment 9:[N
11,1O2,1O2]
+[NTf
2]
-Synthetic
Under magnetic agitation, contain 0.101 mole of (28.7g) LiNTf toward 30ml
2The aqueous solution in be added dropwise to 30ml and contain 0.10 mole of (24.2g) [N
11,1O1,1O2]
+[Br]
-, after dropwising, continue to stir 4h.Reaction stops, and is static, and system is divided into two-layer.Separatory takes off layer, with (twice of 2 * 30ml) water washing.Residual water-content is removed in decompression under 70 ℃, gets colourless liquid [N
11,1O2,1O2]
+[NTf
2]
-38.1g, productive rate: 89%.
Embodiment 10:[N
11,1O2,1O2]
+[BF
4]
-Synthetic
By 1: 1 mol ratio, with 0.2512 mole of (47.73g) [N
11,1O2,1O2]
+[Br]
-With 0.2512 mole of (47.73g) triethyl oxygen a tetrafluoro borate [Et
3O]
+[BF
4]
-Be added to simultaneously in the 50ml methylene dichloride, put drying tube with the moisture in the secluding air, magnetic agitation 2h.70 ℃ of decompressions get [N to remove molecular solvent
11,1O2,1O2]
+[BF
4]
-: 62.6g, productive rate＞99%.
Embodiment 11:[N
11,1O2,1O2]
+[CH
3OSO
3]
-Synthetic
By 1: 1 mol ratio, with 0.30 mole of (72.65g) [N
11,1O2,1O2]
+[Br]
-Successively be added in the 80ml methylene dichloride with 0.30 mole of (37.84g) methyl-sulfate, the room temperature lower magnetic force stirs 2h.70 ℃ of decompressions get [N to remove molecular solvent
11,1O2,1O2]
+[CH
3OSO
3]
-: 93.4g, productive rate＞99%.
Embodiment 12:[N
11,1O2,1O2]
+[C
2H
5OSO
3]
-Synthetic
By 1: 1 mol ratio, with 0.30 mole of (72.65g) [N
11,1O2,1O2]
+[Br]
-Successively be added in the 80ml methylene dichloride with 0.30 mole of (46.25g) ethyl sulfate, the room temperature lower magnetic force stirs 2h.70 ℃ of decompressions get [N to remove molecular solvent
11,1O2,1O2]
+[C
2H
5OSO
3]
-: 93.4g, productive rate＞99%.
Claims (4)
1. one kind is cationic ionic liquid with diether quaternary ammonium, and structural formula is represented with formula (I):
N is 1 to 5 integer in formula (I) ionic liquid, and m is 1 to 5 integer; R
1, R
2, R
3, R
4Get CH independently of one another
3, CH
2CH
3, CH
2CH
2CH
3, CH
2CH
2CH
2CH
3Perhaps CH
2CH
2CH
2CH
2CH
3In a kind of;
Negatively charged ion X in formula (I) ionic liquid
-Be [Cl]
-, [Br]
-, [BF
4]
-, [PF
6]
-, [NO
3]
-, [ClO
4]
-, [CH
3OSO
3]
-, [C
2H
5OSO
3]
-, [N (CN)
2]
-, [(CF
3SO
2)
2N]
-In a kind of.
2. ion liquid synthetic method as claimed in claim 1 is characterized in that synthesis step is as follows:
In the formula (II), step (1) is the tertiary amine that feedstock production contains an ether with halogen ether and secondary amine;
In the formula (II), the diether quaternary ammonium haloid of step (2) gained is raw material with the ether tertiary amine with corresponding halogen ether;
In the formula (II), step (3) is a triethyl oxygen a tetrafluoro borate in order to the material of ion-exchange, methyl-sulfate, ethyl sulfate, dicyandiamide sodium, Potassium Hexafluorophosphate SODIUMNITRATE, SODIUMNITRATE, a kind of in sodium perchlorate or two-(trifluoromethane the sulphonyl)-imido grpup lithium.
3. method as claimed in claim 2 is characterized in that: in the formula (II), the mol ratio of step (1) halogen ether and secondary amine is 1: 2～1: 3.
4. method as claimed in claim 2 is characterized in that: in the formula (II), step (2) diether quaternary ammonium haloid is 1: 1～1: 1.2 with the mol ratio of ether tertiary amine and halogen ether.
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|---|---|---|---|
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ID=42474903
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102789903A (en) * | 2012-01-06 | 2012-11-21 | 华东理工大学 | Preparation process, electrolyte and electrochemical element of electrolytic salt |
| CN102956360A (en) * | 2011-08-17 | 2013-03-06 | 海洋王照明科技股份有限公司 | Capacitor electrolyte and capacitor using same |
| CN110003023A (en) * | 2019-04-24 | 2019-07-12 | 常州沃腾化工科技有限公司 | A kind of environmental-friendly N,N-dimethylformamide dimethylacetal preparation method |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005042466A1 (en) * | 2003-10-31 | 2005-05-12 | Otsuka Chemical Co., Ltd. | Quaternary ammonium salt, electrolyte, electrolyte solution and electrochemical device |
-
2008
- 2008-12-19 CN CN200810189017A patent/CN101747213A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005042466A1 (en) * | 2003-10-31 | 2005-05-12 | Otsuka Chemical Co., Ltd. | Quaternary ammonium salt, electrolyte, electrolyte solution and electrochemical device |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102956360A (en) * | 2011-08-17 | 2013-03-06 | 海洋王照明科技股份有限公司 | Capacitor electrolyte and capacitor using same |
| CN102789903A (en) * | 2012-01-06 | 2012-11-21 | 华东理工大学 | Preparation process, electrolyte and electrochemical element of electrolytic salt |
| CN102789903B (en) * | 2012-01-06 | 2015-05-20 | 华东理工大学 | Preparation process, electrolyte and electrochemical element of electrolytic salt |
| CN110003023A (en) * | 2019-04-24 | 2019-07-12 | 常州沃腾化工科技有限公司 | A kind of environmental-friendly N,N-dimethylformamide dimethylacetal preparation method |
| CN110003023B (en) * | 2019-04-24 | 2021-10-19 | 常州沃腾化工科技有限公司 | Preparation method of environment-friendly N, N-dimethylformamide dimethyl acetal |
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Application publication date: 20100623 |