CN114958389A - High-birefringence mixed liquid crystal for lithium ion battery and preparation method thereof - Google Patents
High-birefringence mixed liquid crystal for lithium ion battery and preparation method thereof Download PDFInfo
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- CN114958389A CN114958389A CN202210679549.2A CN202210679549A CN114958389A CN 114958389 A CN114958389 A CN 114958389A CN 202210679549 A CN202210679549 A CN 202210679549A CN 114958389 A CN114958389 A CN 114958389A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 105
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 229910001416 lithium ion Inorganic materials 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000000178 monomer Substances 0.000 claims abstract description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000012752 auxiliary agent Substances 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 10
- 239000011261 inert gas Substances 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004185 ester group Chemical group 0.000 claims description 9
- 239000002994 raw material Substances 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 7
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 claims description 5
- 101150003085 Pdcl gene Proteins 0.000 claims description 5
- YRAZAPPRLGWDNZ-UHFFFAOYSA-N but-1-ene;carbonic acid Chemical compound CCC=C.OC(O)=O YRAZAPPRLGWDNZ-UHFFFAOYSA-N 0.000 claims description 5
- RAKJQLQDHITSCW-UHFFFAOYSA-N carbonic acid;prop-2-en-1-ol Chemical compound OCC=C.OC(O)=O RAKJQLQDHITSCW-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000007810 chemical reaction solvent Substances 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000005540 biological transmission Effects 0.000 abstract description 7
- 150000002500 ions Chemical class 0.000 abstract description 6
- FXPHJTKVWZVEGA-UHFFFAOYSA-N ethenyl hydrogen carbonate Chemical group OC(=O)OC=C FXPHJTKVWZVEGA-UHFFFAOYSA-N 0.000 abstract description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 3
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 abstract description 3
- 239000011244 liquid electrolyte Substances 0.000 abstract description 3
- 229910052744 lithium Inorganic materials 0.000 abstract description 3
- 238000012545 processing Methods 0.000 abstract description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 abstract description 2
- 238000006266 etherification reaction Methods 0.000 abstract description 2
- 239000007784 solid electrolyte Substances 0.000 abstract description 2
- 239000003792 electrolyte Substances 0.000 description 6
- -1 n-propoxy, n-pentoxy, n-heptoxy Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000002001 electrolyte material Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0216—Super Birefringence Effect (S.B.E.); Electrically Controlled Birefringence (E.C.B.)
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
-
- 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
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Primary Cells (AREA)
Abstract
The invention discloses a high-birefringence mixed liquid crystal for a lithium ion battery and a preparation method thereof, wherein a tolane structure is introduced into a monomer liquid crystal intermediate, and then a vinyl carbonate structure is introduced into monomer liquid crystal molecules through an etherification reaction; the obtained high-birefringence mixed liquid crystal for the lithium ion battery has the advantages of both solid electrolyte and liquid electrolyte, has the characteristics of safety, easy processing, good electrochemical stability, good interface compatibility and the like, has good wettability with electrodes, and can inhibit the growth of dendritic crystals to a certain extent; the monomer liquid crystal contains a vinyl carbonate group and tolane, and can obtain Li + 、Na + The dissolving capacity of alkali metal ions is equal, and the mixed liquid crystal system forms a single domain with a larger area, so that the orientation capacity of liquid crystal molecules is improved,therefore, effective transmission of lithium battery ions is realized, and the comprehensive efficiency of the mixed liquid crystal is improved.
Description
Technical Field
The invention relates to the field of battery electrolyte materials, in particular to a high-birefringence mixed liquid crystal material for a lithium ion battery.
Background
In order to reduce the dependence of human beings on fossil fuels, batteries with high energy and high power density are urgently needed in the field of new energy, and energy conversion and storage become key problems restricting the development of the batteries. For the most commonly used ion batteries at present, the electrolyte has an important influence on the performance of the battery, in addition to the factors of the electrode material. The development of electrolytes with high ion transmission rate, high thermodynamic stability and high electrochemical stability has been receiving attention and is becoming a focus of international research. The liquid crystal material can realize the working temperature of the battery (0-40 ℃ C.) through molecular design) Has excellent thermodynamic and electrochemical stability, and can obtain Li by introducing ethylene carbonate and other groups into liquid crystal molecular structure + 、Na + And the dissolving capacity of the metal salt is equal, so that the liquid crystal material can be applied to the research and development of the electrolyte field to obtain the liquid crystal electrolyte.
The high-birefringence liquid crystal material is used as the electrolyte of the lithium ion battery, and the ethylene carbonate group is grafted at the tail end, so that the transmission capability of the lithium ion is greatly improved, and further, the lithium ion battery has good performance, has the characteristics of safety, easiness in processing, good electrochemical stability, good interface compatibility and the like, has good wettability with an electrode, and can inhibit the growth of dendritic crystals to a certain extent. At present, the mixed liquid crystal system for the lithium ion battery is rarely reported at home and abroad, and particularly, the mixed liquid crystal system with high birefringence is hardly reported in the aspect of a preparation method of a mixed liquid crystal with high birefringence.
Disclosure of Invention
In order to solve the above problems, an object of the present invention is to provide a high birefringence mixed liquid crystal for a lithium ion battery and a method for preparing the same, which can achieve effective transmission of ions in a liquid electrolyte and enhance the ion transmission performance of the electrolyte.
The following specific technical scheme is adopted for achieving the purpose:
a high-birefringence mixed liquid crystal for a lithium ion battery has a structural formula as follows:
wherein: r is C 1 -C 12 Straight-chain saturated alkyl radical or C 1 -C 12 Straight-chain saturated alkoxy radical or C 1 -C 12 Straight-chain saturated ester groups.
A preparation method of high-birefringence mixed liquid crystal for a lithium ion battery comprises the following steps:
wherein: r is C 1 -C 12 Straight-chain saturated alkyl radical or C 1 -C 12 Straight chain saturated alkoxy radicals or C 1 -C 12 Straight-chain saturated ester groups.
Further, the method comprises the following steps:
firstly, dissolving 0.1mol of raw material A in a mixed solvent of 100mL of Tetrahydrofuran (THF) and 100mL of Triethylamine (TEA), placing the mixture in a reactor, introducing inert gas for protection, then adding 0.1mol of raw material p-iodophenol, controlling the reaction temperature at 30-50 ℃, and adding 0.1g of bis (triphenylphosphine) palladium dichloride (Pdcl) 2 (PPh 3 ) 2 ) And 0.2g of cuprous iodide (CuI) as a catalyst, reacting for 12-16h under the protection of inert gas, stopping the reaction, and distilling under reduced pressure to obtain a compound B;
secondly, dissolving 0.06mol of the compound B, 0.06-0.08mol of hydroxymethyl ethylene carbonate and 2-5g of p-toluenesulfonic acid in 500mL of toluene, heating to 110-130 ℃ for dehydration reaction for 5-8h, removing the reaction solvent toluene after the reaction is finished, and purifying a crude product to obtain a monomer liquid crystal in the high-birefringence mixed liquid crystal for the lithium ion battery;
and thirdly, adding the monomer liquid crystal prepared in the third part into a commercial liquid crystal SLC 1717 as a diluent, adding ethyl ethylene carbonate as a functional auxiliary agent, and uniformly stirring to prepare a mixed liquid crystal system, thereby obtaining the high-birefringence mixed liquid crystal for the lithium ion battery.
Further, the mixed liquid crystal system in the third step comprises the following components in percentage by mass: the mass percent of the monomer liquid crystal is 65-80%, the mass percent of the diluent is 10-15%, and the mass percent of the functional auxiliary agent is 5-25%.
Further, the crude product in the second step is purified by adopting a column chromatography method.
The invention has the following advantages:
1. the method respectively prepares R as C 1 -C 12 A straight chain saturated alkyl group of C 1 -C 12 A straight-chain saturated alkoxy radical and is C 1 -C 12 The monomer liquid crystal of linear saturated ester group can finally obtain lithium ion30-40 monomer liquid crystals in the high-birefringence mixed liquid crystal for the sub-battery. Mixing a plurality of monomer liquid crystals containing ethylene carbonate and high-birefringence groups, and adding an accelerant and a regulator at the same time to finally obtain the high-birefringence mixed liquid crystal for the lithium ion battery; the high-birefringence mixed liquid crystal for the lithium ion battery has the advantages of both solid electrolyte and liquid electrolyte, has the characteristics of safety, easiness in processing, good electrochemical stability, good interface compatibility and the like, has good wettability with electrodes, and can inhibit dendritic crystal growth to a certain extent.
2. According to the invention, a tolane structure is introduced into a monomer liquid crystal intermediate through a Sonogashira coupling reaction, and then a vinyl carbonate structure is introduced into monomer liquid crystal molecules through an etherification reaction. The monomer liquid crystal in the high-birefringence mixed liquid crystal for the lithium ion battery contains the vinyl carbonate group, and can obtain the p-Li + 、Na + The dissolving capacity of alkali metal ions is equal, so that the effective transmission of lithium battery ions is realized, and the comprehensive efficiency of the mixed liquid crystal is improved.
3. The monomer liquid crystal in the high-birefringence mixed liquid crystal for the lithium ion battery prepared by the method contains high-birefringence groups, so that the orientation capability of liquid crystal molecules can be improved, a mixed liquid crystal system forms a single domain with a larger area, and the transmission capability of lithium ions is improved.
Detailed Description
In order to facilitate an understanding of the invention, the invention will now be described in detail and individual embodiments of the invention will be given.
A synthetic route of high-birefringence mixed liquid crystal for a lithium ion battery is as follows:
wherein: r is C 1 -C 12 Straight chain saturated alkyl radical or C 1 -C 12 Straight-chain saturated alkoxy radical or C 1 -C 12 Straight chain saturated ester groups.
Example 1
Firstly, dissolving 0.1mol of raw material A in a mixed solvent of 100mL of Tetrahydrofuran (THF) and 100mL of Triethylamine (TEA), placing the mixture in a reactor, introducing inert gas for protection, then adding 0.1mol of raw material p-iodophenol, controlling the reaction temperature at 30 ℃, and adding 0.1g of bis (triphenylphosphine) palladium dichloride (Pdcl) 2 (PPh 3 ) 2 ) And 0.2g of cuprous iodide (CuI) as a catalyst, and reacting for 16h under the protection of inert gas. After the reaction was stopped, the reaction mixture was distilled under reduced pressure to obtain Compound B.
And secondly, dissolving 0.06mol of the compound B, 0.08mol of hydroxymethyl ethylene carbonate and 2g of p-toluenesulfonic acid in 500mL of toluene, heating to 130 ℃ for dehydration reaction for 6h, removing a reaction solvent toluene after the reaction is finished, and purifying a crude product by adopting a column chromatography method to obtain a monomer liquid crystal in the high-birefringence mixed liquid crystal for the lithium ion battery.
According to the first and second steps, R is C 1 -C 12 A straight chain saturated alkyl group of C 1 -C 12 A straight-chain saturated alkoxy radical and is C 1 -C 12 30-40 monomer liquid crystals in the high-birefringence mixed liquid crystal for the lithium ion battery can be finally obtained by using the monomer liquid crystal with the linear chain saturated ester group.
Thirdly, taking 9 monomer liquid crystals in the prepared monomer liquid crystal series, wherein R in the 9 monomer liquid crystals is respectively as follows: n-propyl, n-pentyl, n-heptyl, n-propoxy, n-pentoxy, n-heptoxy, n-propionate, n-valerate, n-heptoate. Meanwhile, adding a commercial liquid crystal SLC 1717 as a diluent, and adding ethyl ethylene carbonate as a functional auxiliary agent to prepare a mixed liquid crystal system, wherein the mixed liquid crystal system comprises the following components in percentage by mass: the total mass percentage of the monomer liquid crystal is 80 percent (wherein the mass of each monomer liquid crystal is the same), the mass percentage of the diluent is 15 percent, and the mass percentage of the functional auxiliary agent is 5 percent. And respectively adding the monomer liquid crystal, the diluent and the functional auxiliary agent into the round-bottom flask, and uniformly stirring to obtain the high-birefringence mixed liquid crystal for the lithium ion battery.
Example 2
In the first step, 0.1mol of starting material A was dissolved in a mixed solvent of 100mL of Tetrahydrofuran (THF) and 100mL of Triethylamine (TEA),placing the mixture in a reactor, introducing inert gas for protection, adding 0.1mol of p-iodophenol as a raw material, controlling the reaction temperature at 50 ℃, and adding 0.1g of bis (triphenylphosphine) palladium dichloride (Pdcl) 2 (PPh 3 ) 2 ) And 0.2g of cuprous iodide (CuI) as a catalyst, and reacting for 12 hours under the protection of inert gas. After the reaction was stopped, the reaction mixture was distilled under reduced pressure to obtain Compound B.
And secondly, dissolving 0.06mol of the compound B, 0.06mol of hydroxymethyl ethylene carbonate and 5g of p-toluenesulfonic acid in 500mL of toluene, heating to 110 ℃ to perform dehydration reaction for 8h, removing a reaction solvent toluene after the reaction is finished, and purifying a crude product by adopting a column chromatography method to obtain a monomer liquid crystal in the high-birefringence mixed liquid crystal for the lithium ion battery.
According to the first and second steps, R is C 1 -C 12 A straight chain saturated alkyl group of C 1 -C 12 A straight-chain saturated alkoxy radical and is C 1 -C 12 30-40 monomer liquid crystals in the high-birefringence mixed liquid crystal for the lithium ion battery can be finally obtained by using the monomer liquid crystal with the linear chain saturated ester group.
Thirdly, 11 monomer liquid crystals are taken from the prepared monomer liquid crystal series, and R in the 11 monomer liquid crystals is respectively as follows: methyl, n-propyl, n-pentyl, n-heptyl, methoxy, n-propoxy, n-pentoxy, n-heptoxy, n-propionate, n-valerate, n-heptoate. Meanwhile, adding a commercial liquid crystal SLC 1717 as a diluent, and adding ethyl ethylene carbonate as a functional auxiliary agent to prepare a mixed liquid crystal system, wherein the mixed liquid crystal system comprises the following components in percentage by mass: the total mass percentage of the monomer liquid crystal is 75 percent (wherein the mass of each monomer liquid crystal is the same), the mass percentage of the diluent is 13 percent, and the mass percentage of the functional auxiliary agent is 12 percent. And respectively adding the monomer liquid crystal, the diluent and the functional auxiliary agent into the round-bottom flask, and uniformly stirring to obtain the high-birefringence mixed liquid crystal for the lithium ion battery.
Example 3
Firstly, 0.1mol of raw material A is dissolved in a mixed solvent of 100mL Tetrahydrofuran (THF) and 100mL Triethylamine (TEA), the mixture is placed in a reactor and is protected by inert gas, then 0.1mol of raw material p-iodophenol is added, and the reaction is carried outThe temperature was controlled at 40 ℃ and 0.1g of bis-triphenylphosphine palladium dichloride (Pdcl) was added 2 (PPh 3 ) 2 ) And 0.2g of cuprous iodide (CuI) as a catalyst, and reacting for 15 hours under the protection of inert gas. After the reaction was stopped, the reaction mixture was distilled under reduced pressure to obtain Compound B.
And secondly, dissolving 0.06mol of the compound B, 0.07mol of hydroxymethyl ethylene carbonate and 4g of p-toluenesulfonic acid in 500mL of toluene, heating to 120 ℃ for dehydration reaction for 5h, removing a reaction solvent toluene after the reaction is finished, and purifying a crude product by adopting a column chromatography method to obtain a monomer liquid crystal in the high-birefringence mixed liquid crystal for the lithium ion battery.
According to the first and second steps, R is C 1 -C 12 A straight chain saturated alkyl group of C 1 -C 12 A straight-chain saturated alkoxy radical and is C 1 -C 12 30-40 monomer liquid crystals in the high-birefringence mixed liquid crystal for the lithium ion battery can be finally obtained by using the monomer liquid crystal with the linear chain saturated ester group.
Thirdly, taking 15 monomer liquid crystals in the prepared monomer liquid crystal series, wherein R in the 15 monomer liquid crystals is respectively as follows: ethyl, n-butyl, n-hexyl, n-octyl, n-decyl, ethoxy, n-butoxy, n-hexyloxy, n-octyloxy, n-decyloxy, acetate, n-butyrate, n-hexanoate, n-octylate, n-decanoate. Meanwhile, adding a commercial liquid crystal SLC 1717 as a diluent, and adding ethyl ethylene carbonate as a functional auxiliary agent to prepare a mixed liquid crystal system, wherein the mixed liquid crystal system comprises the following components in percentage by mass: the total mass percentage of the monomer liquid crystal is 65 percent (wherein the mass of each monomer liquid crystal is the same), the mass percentage of the diluent is 10 percent, and the mass percentage of the functional auxiliary agent is 25 percent. And respectively adding the monomer liquid crystal, the diluent and the functional auxiliary agent into the round-bottom flask, and uniformly stirring to obtain the high-birefringence mixed liquid crystal for the lithium ion battery.
Claims (5)
1. A high-birefringence mixed liquid crystal for a lithium ion battery is characterized in that the structural formula is as follows:
wherein: r is C 1 -C 12 Straight-chain saturated alkyl radical or C 1 -C 12 Straight-chain saturated alkoxy radical or C 1 -C 12 Straight-chain saturated ester groups.
2. A preparation method of high-birefringence mixed liquid crystal for a lithium ion battery is characterized in that the synthesis route of the high-birefringence mixed liquid crystal for the lithium ion battery is as follows:
wherein: r is C 1 -C 12 Straight-chain saturated alkyl radical or C 1 -C 12 Straight chain saturated alkoxy radicals or C 1 -C 12 Straight-chain saturated ester groups.
3. The method for preparing a high birefringence mixed liquid crystal for a lithium ion battery according to claim 2, comprising the steps of:
firstly, dissolving 0.1mol of raw material A in a mixed solvent of 100mL of Tetrahydrofuran (THF) and 100mL of Triethylamine (TEA), placing the mixture in a reactor, introducing inert gas for protection, then adding 0.1mol of raw material p-iodophenol, controlling the reaction temperature at 30-50 ℃, and adding 0.1g of bis (triphenylphosphine) palladium dichloride (Pdcl) 2 (PPh 3 ) 2 ) And 0.2g of cuprous iodide (CuI) as a catalyst, reacting for 12-16h under the protection of inert gas, stopping the reaction, and distilling under reduced pressure to obtain a compound B;
secondly, dissolving 0.06mol of the compound B, 0.06-0.08mol of hydroxymethyl ethylene carbonate and 2-5g of p-toluenesulfonic acid in 500mL of toluene, heating to 110-130 ℃ for dehydration reaction for 5-8h, removing the reaction solvent toluene after the reaction is finished, and purifying a crude product to obtain a monomer liquid crystal in the high-birefringence mixed liquid crystal for the lithium ion battery;
and thirdly, adding the monomer liquid crystal prepared in the third part into a commercial liquid crystal SLC 1717 as a diluent, adding ethyl ethylene carbonate as a functional auxiliary agent, and uniformly stirring to prepare a mixed liquid crystal system, thereby obtaining the high-birefringence mixed liquid crystal for the lithium ion battery.
4. The high birefringence mixed liquid crystal for lithium ion batteries according to claim 3 and the method for preparing the same, wherein: the third step is that the mixed liquid crystal system comprises the following components in percentage by mass: the mass percent of the monomer liquid crystal is 65-80%, the mass percent of the diluent is 10-15%, and the mass percent of the functional auxiliary agent is 5-25%.
5. The high birefringence mixed liquid crystal for lithium ion batteries according to claim 3 and the method for preparing the same, wherein: and purifying the crude product in the second step by adopting a column chromatography method.
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