CN102372732A - Organosiloxane room temperature ionic liquid electrolyte material and its application in electrochemical power storage device - Google Patents
Organosiloxane room temperature ionic liquid electrolyte material and its application in electrochemical power storage device Download PDFInfo
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Abstract
The present invention provides a kind of organic silicon ether ionic liquid at room temperature electrolyte and its applications in electrochemical energy storing device. It is ionic liquid at room temperature of the cationic chemical structural formula containing organic silicon ether, and the chemical structural formula of the cation is as shown in following formula I: wherein R1, R2 and R3 are selected from the alkyl of identical or different C1-C10; M is the ether chain such as (CH2) nO [(CH2) mO] x (CH2) y structure, and n, m are the integer of 0-10, and x, y are the integer of 0-10; R4, R5 and R6 are selected from the alkyl or hydrogen that identical or different C1-C10 alkyl or alkoxy grp or-O-SiR7R8R9, R7, R8 and R9 are C1-C10, and wherein at least one is alkyl. Organic silicon ether ionic liquid at room temperature of the present invention can be used as electrolyte or additive application lithium ion battery, and the oxygen atom of ether chain can generate complexing with lithium ion Li+ in ionic liquid cation chemical structure, promote lithium salts in the degree of dissociation wherein. In addition, containing hydrophobic organosilicon radical and hydrophilic ether (polyethers) segment in cation matrix simultaneously, be conducive to the interface performance for improving battery.
Description
Technical field
The present invention relates to technical field of chemistry, especially relate to one type of organic silicon ether ionic liquid at room temperature electrolyte and the application in electrochemical energy storing device thereof.
Technical background
At present; Employed organic electrolysis material mainly is alkyl carbonate compounds and LiPF6 lithium salts system in the lithium cell industry; High temperature (more than 60 ℃) its performance down descends greatly, and requires higher operating temperature range (being about-30 to 80 ℃) like the used for electric vehicle power cell; And alkyl carbonate class organic electrolysis material has very high combustibility, so there is huge hidden danger in security; Especially in hybrid power and full electric car Application Areas, safety issue is the important factor of these material practical applications of restriction.Concerning super capacitor, because (the E=1/2CV that square is directly proportional of energy stored and electrolytical charging voltage
2), therefore improving the electrolyte electrochemical window will improve the energy of being stored greatly.The used electrolyte of super capacitor mainly contains aqueous electrolyte, organic electrolyte, ionic liquid and solid polymer electrolyte material.Organic electrolyte mainly contains alkyl carbonate (Europe and Japan) and acetonitrile (Acetonitrile, the U.S.), and these ionogen have higher specific conductivity; But the alkyl carbonate material is inflammable, has safety issue, although and acetonitrile has good low-temperature performance, have high volatile volatile and high toxicity.In addition, the electrochemical window of these organic materialss is about 2.7V, and the electrochemical window of water system material is lower, about 1.2V.
Ionic liquid (Ionic Liquid) claim the room temperature melting salt again, is the compound that is made up of ion that under near the temperature room temperature or the room temperature, is in a liquid state, and is made up of negatively charged ion and heteroatomic organic cation such as nitrogenous (quaternary amine type), phosphorus (season phosphonium salt type) usually.Ionic liquid is to belong to and the diverse one type of novel substance crowd of other electrolytes, conventional organic solvents and electrolytic solution; It has caused as the novel green electrolyte and the very big expectation of the extensive interest and the lithium ion battery industrial community of academia very likely has been applied in the electrochemical device (lithium secondary battery, ultracapacitor, dye-sensitized solar cells and fuel cell) as novel green electrolytic solution of future generation in recent years.The ionic liquid kind is a lot, through changing positive anionic various combination, can synthesize the ionic liquid of different structure.Ionic liquid has the physicochemical property of many excellences: (1) vapour pressure is extremely low; (2) thermotolerance is high, liquid temperature wide ranges (can reach 300 ℃); (3) difficult combustion; (4) chemicalstability is high, and good to the solubility property of other polar material; (5) electrochemical window is wide, the decomposition voltage height (can reach～6V); (6) physicochemical property can be through designing adjusting to cationic chemically modified or change negatively charged ion.Ion liquid these special performances make it obtain progressively and widely using in electrochemical field as electrolyte.
A.Balducci etc. reported ionic liquid be the research that is applied to the hydridization super capacitor of green electrolyte (Applied Physics, 2006,627-632), and use (CF has been discussed
3SO
2)
2N
-For anionic cyclic alkyl quaternary ammonium cation is applied to super capacitor as ionogen.People such as Yang Li have reported a kind of N-of containing itrile group-N alkyl morpholine cationic liquid, and its application in lithium ion battery has been discussed, and itrile group helps the dissolving of lithium salts, thereby improve ionic conductivity (Chinese patent, 200710043429.9).Z.Li etc. have reported a kind of new ionic liquid of trimethyl silicon based imidazoles that contains, and as extraction solvent (Talanta, 71,2007,68-72).R.West etc. are in U.S. Pat 7679884B2 and US2009088583-A1; Reported organosilicon season phosphine and the ionic liquid electrolyte material of quaternary ammonium cation class respectively; The organosilicon ionic liquid has some unique character as electrolyte, is suitable for electrochemical energy storing device and uses.
But people also do not have clear understanding to the relation between ion liquid chemical structure composition and material physical and chemical performance and the chemical property so far; Especially as super capacitor and lithium ion battery electrolyte materials; The difficulty of attempting to let ionic liquid possess high ionic conductivity and high electrochemical stability simultaneously also fails to solve, and the consistency of il electrolyte and electrode materials is still waiting to improve.Therefore, for addressing the above problem, also need research and develop ionic liquid with new chemical structure.
Summary of the invention
One of the object of the invention provides one type of organic silicon ether ionic liquid at room temperature electrolyte.
Another object of the present invention provides the application of above-mentioned organic silicon ether ionic liquid at room temperature electrolyte in electrochemical energy storing device.
Organic silicon ether ionic liquid at room temperature electrolyte of the present invention is the ionic liquid at room temperature that the cationic chemical structural formula contains organic silicon ether, and said cationic chemical structural formula is as shown in the formula shown in the I:
R wherein
1, R
2And R
3Be selected from the alkyl of identical or different C1-C10; M is as (CH
2)
nO [(CH
2)
mO]
x(CH
2)
yThe ether chain of structure, n, m are the integer of 0-10, x, y are the integer of 1-10; R
4, R
5And R
6Be selected from identical or different C1-C10 alkyl or alkoxy grp or-O-SiR
7R
8R
9, R
7, R
8And R
9Be alkyl or the hydrogen of C1-C10, wherein at least one is an alkyl.
Formula I compound of the present invention can be used as the quaternary ammonium salt ion liquid electrolyte, and chemical structural formula is as shown in the formula shown in the II:
Negatively charged ion A wherein
-Kind can have a variety of, like various halide anions, BF
4 -, PF
6 -, (CF
3SO
2)
2N
-, and B (C
2O
4)
2Deng, but be not limited to above cited negatively charged ion.
Organic silicon ether ionic liquid at room temperature of the present invention can be used as electrolyte or additive is applied to lithium ion battery, in the ionic liquid cationic chemical structure Sauerstoffatom of ether chain can with lithium ion Li
+Produce complexing, promote lithium salts dissociation degree therein.In addition, contain hydrophobic organosilicon group and hydrophilic ether (polyethers) segment in the positively charged ion skeleton simultaneously, help improving the interface performance of battery.
Description of drawings
Fig. 1 be add 10wt%C1EN1TFSI electrolytic solution (1M LiPF6 EC/DEC/C1EN1TFSI=1/2/0.1) reference cell charge and discharge cycle performance and efficiency curve.
Fig. 2 is the ac impedance spectroscopy (3.4V, 25 ℃) of 10wt%C1EN1TFSI electrolytic solution and commercial electrolyte battery.
Embodiment
The synthetic instance of organic silicon ether ionic liquid electrolyte material of the present invention shown in reaction formula 1, contain ether chain organosilicon amine in THF (THF) solvent with iodomethane reaction, what obtain corresponding negatively charged ion and be iodide ion contains the organic silicon ether quaternary ammonium salt.Concrete synthesis step sees following embodiment for details to be described.
The said ether chain organosilicon amine electrolyte that contains can prepare through following method: excessive alcoxyl alcohol amine compound and sodium Metal 99.5 reaction conversion are corresponding sodium salts, at room temperature add chlorosilane cpd then, reaction system temperature reaction 48h.Use the n-hexane extraction reacting coarse product, air distillation obtains colorless liquid product (like reaction formula 2).When the n in the reaction formula 2 was 0, the embodiment product can react in the refluxed that exists of little metal sodium through hexamethyldisilane amine and corresponding alcoxyl hydramine, and straight run distillation obtains product then.
The synthetic of compound that contains longer polyether chain also can carry out through route shown in reaction formula 3.At first; The glycol of respective chain length and sodium Metal 99.5 and chlorosilane reaction conversion are the organosilicon alkylol cpd; Be corresponding methane sulfonate with the methane sulfonyl chloride reaction conversion then; Be corresponding organosilicon iodide with Soiodin NaI reaction conversion again, last and dimethylamine hydrochloride reaction obtains corresponding organosilicon amine compound.
Reaction formula 3
Work as R
3, R
4And R
5Have in the structure more than one and be equal to ANR
1R
2Or during the structure of polyether chain, the synthetic of embodiment can react at tetrahydrofuran solvent through corresponding chlorosilane and corresponding hydramine and methoxypolyethylene glycol, uses triethylamine to be acid absorber, obtains product at last.Shown in reaction formula 4.
Reaction formula 4
Embodiment 1:C1EN1ILI
N, (7g 40mmol) and methyl iodide (6.8g, 1.2 equivalents) back flow reaction 8 hours in the 50mLTHF solvent, is precipitated out with anhydrous diethyl ether TMSDMA N dimethylamine base oxethyl methyl trimethoxy base silane (TMSC1EN1), is using CH then
2Cl
2/ Et
2The O recrystallization obtains white solid ([CH
3]
3SiCH
2OCH
2CH
2) N [CH
3]
+ 3I
-
1H-NMR(600MHz，CDCl
3)：0.033(s，9H，TMS)，3.188(s，2H，TMSCH2)，3.488(s，9H，NCH3)3)，3.91(m，4H，CH2CH2).
13C?NMR(600MHz，CDCl3)：：0.0000，57.970(t，J＝3.6Hz)，69.052(t，J＝2.7)，69.391，72.183.
Embodiment 2:C1EN2ILI
Adopt embodiment 1 identical compound method to obtain product, [CH
3]
3SiCH
2OCH
2CH
2OCH
2CH
2N [CH
3]
+ 3I
-
1H-NMR(600MHz，CDCl
3)：0.055(s，9H，SiCH3)，3.148(s，2H，TMSCH2)，3.514(s，9H，NCH3)，3.58(t，J＝4.5，2H，NCH2)，3.67(t，J＝4.5，2H，SiCH2N)，3.993(s，4H，TMSC1OCH2CH2O).
13CNMR(600MHz，CDCl3)：0.00，58.0(t，J
C-N＝3.5Hz)，68.04，68.58，68.77(t，J
C-N＝2.8Hz)，73.476，77.191.
Embodiment 3:C1EN3ILI
Adopt embodiment 1 identical compound method to obtain product [CH
3]
3SiCH
2O (CH
2CH
2O)
2CH
2CH
2N [CH
3]
+ 3I
-
1H-NMR (600MHz, CDCl
3) :-0.052 (s, 9H, SiCH3), 0.388 (m, 2H, TMSCH2), 1.515 (m, 2H, TMSCCH2); 3.349 (t, J=7.2,2H, CH2NMe2), 3.468 (s, 9H, NCH3), product 3.523 (m; 2H, CH2N (CH3) 2), 3.50 (m, 2H, CH2CH2N (CH3) 3), 3.995 (s, 4H, CH2CH2O).
13C?NMR(600MHz，CDCl3)：0.001，14.160，25.717，56.70，66.785，67.480，71.245，72.348，75.998.
Embodiment 4:C3EN1ILI
Adopt embodiment 1 identical compound method to obtain product [CH
3]
3Si (CH
2)
3OCH
2CH
2N [CH
3]
+ 3I
-
1H-NMR(600MHz，CDCl
3)：-0.052(s，9H，SiCH3)，0.402(m，2H，TMSCH2)，1.50(m，2H，TMSCCH2)，3.408(t，J＝6.9Hz，2H，CH2OEN1)，3.472(s，9H，N(CH3)3)，3.872(sbr.，4H，OCH2CH2N).
13C?NMR(600MHz，CDCl3)：-0.002，14.360，25.651，56.682(t，J＝3.45Hz)，66.432，67.665(t，J＝2.4)，76.339.
Embodiment 5:C3EN2ILI
Adopt embodiment 1 identical compound method to obtain product [CH
3]
3Si (CH
2)
3OCH
2CH
2OCH
2CH
2N [CH
3]
+ 3I
-
1H-NMR(600MHz，CDCl
3)：-0.052(s，9H，SiCH3)，0.388(m，2H，TMSCH2)，1.515(m，2H，TMSCCH2)，3.349(t，J＝7.2，2H，CH2NMe2)，3.468(s，9H，NCH3)，3.523(m，2H，CH2N(CH3)2)，3.50(m，2H，CH2CH2N(CH3)3)，3.995(s，4H，CH2CH2O).
13C?NMR(600MHz，CDCl3)：0.001，14.160，25.717，56.70，66.785，67.480，71.245，72.348，75.998.
Embodiment 6:C1PrEN1ILI
Adopt embodiment 1 identical compound method to obtain product [CH
3]
3SiCH
2OCH
2CH
2CH
2N [CH
3]
+ 3I
-
1H-NMR(600MHz，CDCl
3)：-0.01(s，9H，TMS)，2.201(m，2H，OCH2)，3.060(s，2H，TMSCH2)，3.431(s，9H，NMe3)，3.478(m，4H，OCH2CH2)，3.607(t，2H，J＝7.8Hz，CH2N).
13C?NMR(600MHz，CDCl3)：0.002，27.078，56.936(t，J＝3.5Hz)，68.477，73.829.
The organic silicon ether ionic liquid at room temperature can the method shown in reaction formula 1 carry out the IX preparation through the lithium salts with respective anionic.For example, contain ether chain organosilicon iodine negatively charged ion quaternary ammonium salt (20g) and be dissolved in 50ml dry acetone, room temperature reaction 4 hours with respective anionic lithium salts (1.1 equivalents, the embodiment of the invention are TFSI, and the preparation method is identical for other anion ion liquids).Rotary evaporation removes and desolvates, and is dissolved in CH then
2Cl
2In, separate organic phase, organic phase is washed several times with deionized water, anhydrous MgSO
4Drying obtains product after desolvating, 100 ℃ in last vacuum dry 48 hours down, thereby corresponding ionic liquid embodiment below obtaining.
Embodiment 7:C1EN1TFSII
I ion through with TFSI ionic replacement embodiment 1 compound obtains.
1H-NMR(600MHz，CDCl
3)：0.069(s，9H，TMS)，3.212(s，2H，TMSCH2)，3.242(s，9H，NCH3)3)，3.60(m，2H，CH2CH2)，3.84(m，2H，)
13C?NMR(600MHz，CDCl3)：：-0.002，57.72(t，J＝3.8Hz)，69.418(t，J＝2.6)，72.109，123.180(q，J＝319.35Hz).
29Si?NMR(600MHz，CDCl3)：-2.111.
Embodiment 8:C1EN2TFSII
I ion through with TFSI ionic replacement embodiment 2 compounds obtains.
1H-NMR(600MHz，CDCl
3)：-0.017(s，9H，SiCH3)，3.082(s，2H，TMSCH2)，3.189(s，9H，NCH3)，3.55(m，6H，TMSC1OCH2CH2O?CH2)，3.88(m，2H，NCH2).C13：.3.66(m，2H，O
CH2CH2N)，3.95(m，2H，OCH2
CH2N).
13C?NMR(600MHz，CDCl3)：-0.001，57.68(t，J＝3.82)，67.95，68.68，69.10(t，J＝3.0)，73.54，77.47，123.01(q，J
C-F＝319.5).
29Si?NMR(600MHz，CDCl3)：-2.624.
Embodiment 9:C1EN3TFSI
I ion through with TFSI IX embodiment 3 compounds obtains.
1H-NMR：0.055(s，9H，SiCH3)，3.148(s，2H，TMSCH2)，3.514(s，9H，NCH3)，3.58(t，J＝4.5，2H，NCH2)，3.67(t，J＝4.5，2H，SiCH2N)，3.993(s，4H，TMSC1OCH2CH2O).
13C?NMR(600MHz，CDCl3)：-3.11，54.54(t，J
C-N＝3.4Hz)，64.78，65.34，65.97，70.20(t，J
C-N＝3.0Hz)，74.65，76.84，77.06，77.27，119.77(q，J
C-F＝321.2Hz).
Embodiment 10:C3EN1TFSI
I ion through with TFSI ionic replacement embodiment 4 compounds obtains.
1H-NMR(600MHz，CDCl
3)：-0.049(s，9H，SiCH3)，0.40(m，2H，TMSCH2)，1.51(m，2H，TMSCCH2)，3.195(s，9H，N(CH3)3)，3.40(t，J＝6.9Hz，2H，OCH2CH2N)，3.54(t，2H，J＝4.8Hz，CH2N).
13C?NMR(600MHz，CDCl3)：0.001，14.418，25.728，56.364(t，J＝3.9)，66.206，67.963(t，J＝3.0Hz).76.442，121.713(q，J＝319.35Hz).
29Si?NMR(600MHz，CDCl3)：0.722.
Embodiment 11:C3EN2TFSI
I ion through with TFSI ionic replacement embodiment 5 compounds obtains.
1H-NMR(600MHz，CDCl
3)：-0.007(s，9H，SiCH
3)，0.455(m，2H，TMSCH
2)，1.56(m，2H，TMSCCH
2)，3.265(s，6H，NCH
3)，3.418(t，J＝7.2，2H，SiCH
2N)，3.59(m，4H，TMSC
3O
CH 2 CH 2 OCH2)；
13C?NMR(600MHz，CDCl3)：0.003，14.288，25.87，56.344，66.596，67.786，71.360，72.384，76.091，121.64(q，J＝319.5Hz).
29Si?NMR(600MHz，CDCl3)：0.700.
Embodiment 12:C1PrEN1TFSI
I ion through with TFSI ionic replacement embodiment 6 compounds obtains.
1H-NMR(600MHz，CDCl
3)：0.041(s，9H，TMS)，2.037(m，2H，OCH2)，3.114(s，2H，TMSCH2)，3.186(s，9H，NMe3)，3.422(m，2H，O
CH2CH2)，3.504(t，2H，J＝5.4Hz，CH2N).
13C?NMR(600MHz，CDCl3)：0.004，26.996，56.662，68.647，73.968，123.028(q，J＝319.35).
29Si?NMR(600MHz，CDCl3)：-2.361。
Table 1 is an embodiment 7-12 ion liquid compound physical performance data form.List data comprises the ionic conductivity of viscosity, second-order transition temperature, incendivity and 25 ℃ of following materials of measurement, and these materials do not burn, and has higher specific conductivity and suitable second-order transition temperature and viscosity performance.
Table 1
Compound η (cP) T
g(℃) σ (mS/cm) incendivity
C1EN1TFSI 174-67 0.73 is not
C1EN2TFSI 125-72 0.78 is not
C1EN3TFSI 152-0.75 is not
C3EN1TFSI 178-68 0.25 is not
C3EN2TFSI 148-71 0.63 is not
C1PrEN1TFSI 230-64 0.62 is not
In battery performance test, employed electrolytic solution, LiPF
6From Guotai Huarong Chemical New Material Co., Ltd., Zhangjiagang City, LiFePO
4Be Tianjin Si Telan energy technology ltd, barrier film is an Asashi Chemical Industry Company products.The preparation of electrolytic solution and the assembling of battery are all carried out under argon gas (purity is greater than 99.9999%) atmosphere.With LiPF
6Be dissolved in ethyl-carbonate and diethyl carbonate (EC: DEC=1: be made into the electrolytic solution that concentration is 1M 2), in this electrolytic solution, add the embodiment of the invention 7 Compound C 1EN1TFSI of 10wt%.Utilize LiFePO
4Do positive and negative electrode respectively with metallic lithium, be assembled into button cell (2025), under room temperature (25 ℃), carry out charge/discharge in the new prestige battery charging and discharging test macro then and test charging/discharging voltage 2.5V-4.1V with Shenzhen.To battery charge, carry out constant current charge with the constant current of 0.1C or 0.2C then, discharge-rate is 0.1C or 0.2C.
Fig. 1 charges and discharge cycle performance and battery efficiency curve for the 0.2C of above-mentioned battery, and battery table reveals 100% efficient and stable cycle performance, and the specific storage of battery reaches 147mAh/g.
For doing contrast, use commercial electrolytic solution (1M LiPF
6(EC: DEC=1: 2, contain 1% vinylene carbonate VC and 1% NSC 11801 VEC), the method assembling button cell (2025) by identical carries out the charge/discharge compare test with the 0.2C multiplying power then.Control cell have suitable basically specific storage, efficient and a cycle performance, but the test result of the ac impedance spectroscopy after two batteries circulations 50 times is shown, add the interface performance that 10wt% embodiment 7 Compound C 1EN1TFSI can significantly improve battery.As shown in Figure 2,10wt% embodiment 7 compound batteries are less than commercial electrolyte battery (185 Ω) at high frequency region corresponding to the impedance (127 Ω) of solid electrolyte interface film (SEI), have better dynamic characteristic.
Claims (4)
1. an organic silicon ether ionic liquid at room temperature electrolyte is characterized in that it is the ionic liquid at room temperature that the cationic chemical structural formula contains organic silicon ether, and said cationic chemical structural formula is as shown in the formula shown in the I:
R wherein
1, R
2And R
3Be selected from the alkyl of identical or different C1-C10; M is as (CH
2)
nO [(CH
2)
mO]
x(CH
2)
yThe ether chain of structure, n, m are the integer of 0-10, x, y are the integer of 1-10; R
4, R
5And R
6Be selected from identical or different C1-C10 alkyl or alkoxy grp or-O-SiR
7R
8R
9, R
7, R
8And R
9Be alkyl or the hydrogen of C1-C10, wherein at least one is an alkyl.
2. the application of organic silicon ether ionic liquid at room temperature electrolyte as claimed in claim 1 in electrochemical energy storing device.
3. the application of organic silicon ether ionic liquid at room temperature electrolyte as claimed in claim 2 in electrochemical energy storing device is characterized in that said organic silicon ether ionic liquid at room temperature electrolyte is used as the quaternary ammonium salt ion liquid electrolyte.
4. like claim 2 or 3 application of described organic silicon ether ionic liquid at room temperature electrolyte in electrochemical energy storing device, it is characterized in that said organic silicon ether ionic liquid at room temperature electrolyte is applied to lithium ion battery as electrolyte or additive.
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| CN102723528A (en) * | 2012-06-06 | 2012-10-10 | 中国科学院广州能源研究所 | Amphoteric ionic liquid electrolyte material, preparation method thereof and application thereof to lithium battery electrolyte |
| CN103113242A (en) * | 2012-12-28 | 2013-05-22 | 中国科学院广州能源研究所 | Functional choline chloride ionic liquid and preparation method and application in electrochemical energy storage device thereof |
| CN103855425A (en) * | 2012-12-04 | 2014-06-11 | 中国科学院大连化学物理研究所 | Electrolyte solution of lithium-sulfur battery |
| US20150093655A1 (en) * | 2012-04-05 | 2015-04-02 | HYDRO-QUéBEC | Ionic compounds having a silyloxy group |
| CN108682567A (en) * | 2018-05-09 | 2018-10-19 | 中国科学院兰州化学物理研究所 | A method of constructing high-performance super capacitor by adjusting electrode voltage range |
| CN108701866A (en) * | 2015-12-14 | 2018-10-23 | 诺姆斯科技有限公司 | Silane-functionalised ionic liquid |
| WO2018221676A1 (en) * | 2017-06-01 | 2018-12-06 | 日立化成株式会社 | Electrolytic solution and electrochemical device |
| WO2018220997A1 (en) * | 2017-06-01 | 2018-12-06 | 日立化成株式会社 | Electrolytic solution and electrochemical device |
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