CN114456067B - Synthesis method of di (2, 2-trifluoroethyl) carbonate - Google Patents
Synthesis method of di (2, 2-trifluoroethyl) carbonate Download PDFInfo
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- CN114456067B CN114456067B CN202210159240.0A CN202210159240A CN114456067B CN 114456067 B CN114456067 B CN 114456067B CN 202210159240 A CN202210159240 A CN 202210159240A CN 114456067 B CN114456067 B CN 114456067B
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- carbonate
- trifluoroethyl
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- trifluoroethanol
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title claims abstract description 28
- 238000001308 synthesis method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 33
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims abstract description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 58
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 19
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 238000005809 transesterification reaction Methods 0.000 claims description 12
- 238000005191 phase separation Methods 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 5
- 150000002148 esters Chemical group 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000002000 Electrolyte additive Substances 0.000 abstract description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 8
- 229910001416 lithium ion Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000003682 fluorination reaction Methods 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of bis (2, 2-trifluoroethyl) carbonate, and relates to the technical field of battery electrolyte additives. According to the invention, diphenyl carbonate is taken as a raw material and is pre-reacted with imidazole, so that the ester exchange reaction difficulty of trifluoro ethoxy is reduced, and meanwhile, compared with the reaction which is carried out by directly taking N, N-carbonyl diimidazole as a raw material, the reaction is milder, byproducts are fewer, and the yield is higher.
Description
Technical Field
The invention relates to the technical field of battery electrolyte additives, in particular to a synthesis method of bis (2, 2-trifluoroethyl) carbonate.
Background
The lithium ion battery has the advantages of high energy density, high output voltage, long cycle life, no memory effect, small environmental pollution and the like, and is the secondary battery with the most attractive and development potential. At present, the solvents used in the lithium ion battery electrolyte are generally carbonates, and the solvents can improve the charge-discharge capacity and the cycle life of the lithium ion battery, but have lower flash points, and in recent years, reports about fires and even explosions caused by the lithium ion battery are very common. The safety problem of lithium ion batteries is generally concerned by people, and the safety is a bottleneck which restricts the development of the lithium ion batteries to the high energy and large-scale directions.
Fluorinated solvents generally have a relatively high flash point or even no flash point, and thus the use of fluorinated solvents is advantageous for improving the safety of lithium ion batteries. The fluorocarbonate compound has the advantages of stable physical and chemical properties, high dielectric constant and flash point, good intersolubility with electrolyte salt and other organic solvents, and the like, and becomes a preferred substitute of the electrolyte solvent of the lithium ion battery.
Bis (2, 2-trifluoroethyl) carbonate is used as an important carbonate additive in lithium battery electrolyte, can obviously reduce the combustion self-extinguishing time of the electrolyte and improve the safety performance of the battery, and therefore becomes a hot spot for current research.
The current methods for synthesizing the di (2, 2-trifluoroethyl) carbonic ester mainly comprise a phosgene method, a direct fluorination method, a halogenation fluorination method and an ester exchange method. The phosgene process results in lower yields of bis (2, 2-trifluoroethyl) carbonate due to poor selectivity and is less studied. Although the conversion rate of the direct fluorination method is high, the method is not easy to control the products, byproducts and impurities, so that the method is less researched. The most studied transesterification and halofluorination processes are currently the most studied, and these two processes are believed to be of higher yields. Although the halogenation fluorination method has a high yield, the reaction process is relatively complicated. The transesterification method is a relatively green synthetic method, but since the base-catalyzed transesterification reaction is a nucleophilic substitution reaction, once the alkyl alcohol is changed into fluorocarbon alcohol, steric hindrance increases, catalytic activity decreases, and the ability to undergo the exchange reaction deteriorates.
Disclosure of Invention
The present invention is directed to a method for synthesizing bis (2, 2-trifluoroethyl) carbonate, which solves the problems set forth in the background art.
In order to achieve the above purpose, the present invention provides the following technical solutions:
The synthesis method is characterized in that diphenyl carbonate is taken to react with imidazole in advance under the catalysis of aluminum chloride under the protection of inactive gas, the reaction is cooled to room temperature, methylene dichloride solution containing trifluoroethanol is dropwise added, after the dropwise addition is finished, the reflux is carried out for transesterification, hydrochloric acid is dropwise added to adjust the reaction to be acidic after the reaction is finished, phase separation is carried out, and the obtained methylene dichloride phase is concentrated and rectified to obtain the di (2, 2-trifluoroethyl) carbonate, wherein the specific chemical reaction formula is as follows:
Further, the molar ratio of diphenyl carbonate to imidazole is 1:6 to 7.
Further, the molar ratio of diphenyl carbonate to trifluoroethanol is 1:2.3 to 2.5.
Further, the weight ratio of diphenyl carbonate to aluminum chloride is 1:0.1 to 0.15.
Further, the temperature of the pre-reaction is 70-80 ℃ and the time is 2-3 h.
Further, the transesterification reaction time is 2 to 3 hours.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, diphenyl carbonate is taken as a raw material and is pre-reacted with imidazole, so that the ester exchange reaction difficulty of trifluoro ethoxy is reduced, and meanwhile, compared with the reaction which is carried out by directly taking N, N-carbonyl diimidazole as a raw material, the reaction is milder, byproducts are fewer, and the yield is higher;
The synthesis method has the advantages of simple operation, fewer reaction steps and easy purification, the control of the reaction conditions at each stage ensures the maximization of the product yield and the product purity in the production process, and the yield of the product is further improved by reasonably controlling the consumption of the reaction raw materials and the reaction process.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Embodiment one:
the synthesis method of the bis (2, 2-trifluoroethyl) carbonate comprises the following synthesis steps:
24g (0.24 mol) of trifluoroethanol was added to 100mL of methylene chloride to prepare a methylene chloride solution of trifluoroethanol;
Under the protection of nitrogen, 21.4g (0.1 mol) of diphenyl carbonate and 40.95g (0.65 mol) of imidazole are taken and mixed, 2.6g of aluminum chloride is added, the mixture is heated to 80 ℃, the mixture is kept at 80 ℃ and stirred for pre-reaction for 2 hours, then the mixture is cooled to room temperature, methylene dichloride solution containing trifluoroethanol is dropwise added, after the dropwise addition is finished, the mixture is refluxed for transesterification for 2 hours, hydrochloric acid is dropwise added to adjust the pH to be 1 after the reaction is finished, phase separation is carried out, and the obtained methylene dichloride phase is concentrated and rectified to obtain 19.57g of bis (2, 2-trifluoroethyl) carbonate, the yield is 86.59%, the purity is 99.97%, and the specific chemical reaction formula is as follows:
embodiment two:
the synthesis method of the bis (2, 2-trifluoroethyl) carbonate comprises the following synthesis steps:
23g (0.23 mol) of trifluoroethanol was added to 80mL of methylene chloride to prepare a methylene chloride solution of trifluoroethanol;
Under the protection of nitrogen, 21.4g (0.1 mol) of diphenyl carbonate and 41.58g (0.66 mol) of imidazole are taken and mixed, 2.14g of aluminum chloride is added, the mixture is heated to 70 ℃, the mixture is kept at 70 ℃ and stirred for pre-reaction for 3 hours, then the mixture is cooled to room temperature, methylene dichloride solution containing trifluoroethanol is dripped, after the dripping is finished, the mixture is refluxed for transesterification for 2.5 hours, hydrochloric acid is dripped to adjust the pH to be 1.5 after the reaction is finished, phase separation is carried out, and the obtained methylene dichloride phase is concentrated and rectified, thus 19.14g of bis (2, 2-trifluoroethyl) carbonate is obtained, the yield is 84.69%, and the purity is 99.91%.
Embodiment III:
the synthesis method of the bis (2, 2-trifluoroethyl) carbonate comprises the following synthesis steps:
24g (0.24 mol) of trifluoroethanol was added to 90mL of dichloromethane to prepare a dichloromethane solution of trifluoroethanol;
under the protection of nitrogen, 21.4g (0.1 mol) of diphenyl carbonate and 44.1g (0.7 mol) of imidazole are taken and mixed, 3.21g of aluminum chloride is added, the mixture is heated to 75 ℃, the mixture is kept at 75 ℃ and stirred for pre-reaction for 2.5 hours, then the mixture is cooled to room temperature, methylene dichloride solution containing trifluoroethanol is dripped, after the dripping is finished, the mixture is refluxed for transesterification for 3 hours, hydrochloric acid is dripped to adjust the pH to be 2 after the reaction is finished, and the obtained methylene dichloride phase is concentrated and rectified to obtain 19.29g of bis (2, 2-trifluoroethyl) carbonate, and the yield is 85.35 percent and the purity is 99.93 percent.
Embodiment four:
the synthesis method of the bis (2, 2-trifluoroethyl) carbonate comprises the following synthesis steps:
25g (0.25 mol) of trifluoroethanol was added to 110mL of dichloromethane and the mixture was used as a dichloromethane solution of trifluoroethanol;
Under the protection of nitrogen, 21.4g (0.1 mol) of diphenyl carbonate and 37.8g (0.6 mol) of imidazole are stirred and mixed, 2.8g of aluminum chloride is added, the mixture is heated to 78 ℃, the mixture is kept at 78 ℃ and stirred for pre-reaction for 2.8 hours, then the mixture is cooled to room temperature, methylene dichloride solution containing trifluoroethanol is dripped, after the dripping is finished, the mixture is refluxed for transesterification for 2.8 hours, hydrochloric acid is dripped to adjust the pH to be 1.2 after the reaction is finished, phase separation is carried out, and the obtained methylene dichloride phase is concentrated and rectified, thus 19.11g of bis (2, 2-trifluoroethyl) carbonate is obtained, and the yield is 84.56% and the purity is 99.94%.
Fifth embodiment:
the synthesis method of the bis (2, 2-trifluoroethyl) carbonate comprises the following synthesis steps:
24g (0.25 mol) of trifluoroethanol was added to 100mL of methylene chloride to prepare a methylene chloride solution of trifluoroethanol;
under the protection of nitrogen, 21.4g (0.1 mol) of diphenyl carbonate and 40.32g (0.64 mol) of imidazole are taken and mixed, 3g of aluminum chloride is added, the mixture is heated to 79 ℃, the mixture is maintained at 79 ℃ and stirred for pre-reaction for 2.6 hours, then the mixture is cooled to room temperature, methylene dichloride solution containing trifluoroethanol is dropwise added, after the dropwise addition is finished, the mixture is refluxed for transesterification for 2.4 hours, hydrochloric acid is dropwise added to adjust the pH to be 1.5 after the reaction is finished, phase separation is carried out, and the obtained methylene dichloride phase is concentrated and rectified to obtain 19.34g of bis (2, 2-trifluoroethyl) carbonate, the yield is 85.58%, and the purity is 99.95%.
Comparative example:
The product bis (2, 2-trifluoroethyl) carbonate was purchased commercially and was found to have a yield of 69.1% and a purity of 98%.
The yields and purities of the final products of examples one to five were compared with those of the comparative examples, and the comparison results are shown in table 1:
As can be seen from Table 1, the yield and purity of the produced bis (2, 2-trifluoroethyl) carbonate were higher than those of commercial products by the synthesis method of the bis (2, 2-trifluoroethyl) carbonate of the present invention.
TABLE 1
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (5)
1. A synthesis method of di (2, 2-trifluoroethyl) carbonate is characterized in that: under the protection of inactive gas, diphenyl carbonate is taken to react with imidazole under the catalysis of aluminum chloride, the reaction is cooled to room temperature, methylene dichloride solution containing trifluoroethanol is dripped, after the dripping is finished, the reflux is carried out, the transesterification reaction is carried out, hydrochloric acid is dripped to adjust the reaction to acidity, the phase separation is carried out, and the obtained methylene dichloride phase is concentrated and rectified to obtain the di (2, 2-trifluoroethyl) carbonate, wherein the specific chemical reaction formula is as follows:
the pre-reaction temperature is 70-80 ℃ and the pre-reaction time is 2-3 h.
2. The method for synthesizing bis (2, 2-trifluoroethyl) carbonate according to claim 1, wherein: the molar ratio of diphenyl carbonate to imidazole is 1:6 to 7.
3. The method for synthesizing bis (2, 2-trifluoroethyl) carbonate according to claim 1 or 2, wherein: the molar ratio of diphenyl carbonate to trifluoroethanol is 1:2.3 to 2.5.
4. The method for synthesizing bis (2, 2-trifluoroethyl) carbonate according to claim 1 or 2, wherein: the weight ratio of diphenyl carbonate to aluminum chloride is 1:0.1 to 0.15.
5. The method for synthesizing bis (2, 2-trifluoroethyl) carbonate according to claim 1 or 2, wherein: the transesterification reaction time is 2-3 h.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496908A (en) * | 2014-12-24 | 2015-04-08 | 江苏康乐新材料科技有限公司 | Preparation method of carbonyl diimidazole |
| CN112898157A (en) * | 2019-11-18 | 2021-06-04 | 石家庄圣泰化工有限公司 | Synthesis method of di (2,2, 2-trifluoroethyl) carbonate |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104496908A (en) * | 2014-12-24 | 2015-04-08 | 江苏康乐新材料科技有限公司 | Preparation method of carbonyl diimidazole |
| CN112898157A (en) * | 2019-11-18 | 2021-06-04 | 石家庄圣泰化工有限公司 | Synthesis method of di (2,2, 2-trifluoroethyl) carbonate |
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