CN115010694B - Fluoroethylene carbonate and preparation method thereof - Google Patents
Fluoroethylene carbonate and preparation method thereof Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
- B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
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- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
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Abstract
The invention relates to the field of organic synthesis, and particularly discloses fluoroethylene carbonate and a preparation method thereof. The preparation method of fluoroethylene carbonate comprises the following steps: step 1, under the protection of inert gas, adding an anhydrous solvent, anhydrous carbonate, anhydrous potassium fluoride and a catalyst into a reaction kettle, raising the temperature to 120-135 ℃, and then dripping 1, 2-trichloroethane liquid for 1-2h for reaction; step 2, after the reaction is carried out for 1-2 hours at the temperature, stopping the reaction, cooling to the room temperature, filtering, and taking filtrate for standby; step 3, distilling to remove the solvent; step 4, continuing distillation to distill out a crude product; and 5, rectifying to obtain fluoroethylene carbonate. The preparation method has the advantages of accurate substitution position, less byproducts and easy purification. The fluoroethylene carbonate prepared by the preparation method has the advantages of low production cost and high economic value.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to fluoroethylene carbonate and a preparation method thereof.
Background
The fluoroethylene carbonate is a chemical substance, is mainly applied to an electrolyte additive of a lithium ion battery, and can prevent the electrolyte from further decomposition and improve the low-temperature performance of the electrolyte.
At present, fluoroethylene carbonate is mainly prepared by direct fluorination, namely, ethylene carbonate, fluorine gas and inert gas are directly mixed at a certain temperature to carry out substitution reaction, but the method has higher cost and lower economic value.
In addition, there is a more common method at present: the method is characterized in that the vinyl carbonate is taken as a raw material, chloroethylene carbonate is obtained through chlorine chlorination, and then potassium fluoride is used for fluorination, so that fluoroethylene carbonate is obtained, but in the preparation method, the conversion rate and the selectivity in the step of chloridizing the vinyl carbonate by the chlorine are low, the general conversion rate is about 90%, the selectivity is about 80%, and the byproduct of the chloroethylene carbonate is more, generally 5-8%, so that the content of the subsequent fluorination reaction is easily reduced, great trouble is easily caused to the purification of a reaction product, and the yield of the two steps is generally only about 65%, so that the improvement still remains.
Disclosure of Invention
In order to better improve the purity of fluoroethylene carbonate and simplify the purification operation of reaction products, the application provides fluoroethylene carbonate and a preparation method thereof.
In a first aspect, the present application provides a method for preparing fluoroethylene carbonate, which adopts the following technical scheme:
a method for preparing fluoroethylene carbonate, comprising the following steps:
step 1, under the protection of inert gas, adding an anhydrous solvent, anhydrous carbonate, anhydrous potassium fluoride and a catalyst into a reaction kettle, raising the temperature to 120-135 ℃, and then dripping 1, 2-trichloroethane liquid for 1-2h for reaction;
wherein the catalyst is any one of R-2,2 '-bis (dimethylphosphine) -3,3' -bis (formylisopropylimine) -1,1 '-binaphthyl-6, 6' -disulfonate or R-2,2 '-bis (dimethylphosphine) -3,3' -bis (formylphenylimine) -1,1 '-binaphthyl-6, 6' -disulfonate;
step 2, after the reaction is carried out for 1-2 hours at the temperature, stopping the reaction, cooling to the room temperature, filtering, and taking filtrate for standby;
step 3, distilling the filtrate obtained in the step 2, and removing the solvent;
step 4, when no liquid flows out in the step 3, continuously increasing the temperature and distilling the residual filtrate in the step 3 to obtain a crude product;
and 5, rectifying the crude product to obtain fluoroethylene carbonate.
The preparation method of the catalyst comprises the following steps: (R) -2, 2-bis (dimethylphosphine) -1, 1-binaphthyl (0.01 mol), bromine (0.022 mol) and 100mL of acetone are added into a reaction bottle, the mixture is reacted at the temperature of minus 20 ℃ to obtain (R) -6,6' -dibromo-2, 2' -bis (dimethylphosphine) -1,1' -binaphthyl (0.01 mol), and then 50mL of sodium sulfite solution with the mass concentration of 0.2mol/L is added, and the corresponding sodium sulfonate salt is obtained after the reaction.
The sodium sulfonate (0.05 mol), LDA (0.12 mol), DMF (0.13 mol) and 50-100mL diethyl ether obtained from the above reaction were mixed and reacted at-65℃to obtain sodium diformyl sulfonate. Refluxing diformyl sodium sulfonate and corresponding alkylamine (0.11 mol) in ethanol to obtain ligand, mixing ligand 0.01mol and palladium chloride 0.02mol, refluxing and stirring in acetone for 12-15h, evaporating most of solvent, cooling to room temperature, adding 100-150g diethyl ether under stirring, standing for crystallization, filtering, collecting filter cake, rinsing with diethyl ether to obtain the catalyst.
The molecular formula of the catalyst is shown as follows:
by creatively adopting 1, 2-trichloroethane, anhydrous carbonate and anhydrous potassium fluoride as reactants, under the conditions of inert gas and reflux, under the induction of catalyst catalysis and strong polar aprotic solvent, the 1, 2-trichloroethane and the carbonate preferentially catalyze C-O coupling reaction to generate chloroethylene carbonate, the selectivity of the reaction is close to 100 percent, no chloroethylene carbonate is generated, and meanwhile, the anhydrous potassium fluoride in a reaction system can further react with the generated chloroethylene carbonate to obtain fluoroethylene carbonate, so that the substitution position of the fluoroethylene carbonate is more accurate, the generation of byproducts is reduced, the subsequent purification operation is simpler and more convenient, the conversion rate of the reaction is improved, and the purity of the product is improved.
In addition, by creatively adopting any one of R-2,2 '-di (dimethylphosphine) -3,3' -di (formylisopropylimine) -1,1 '-binaphthyl-6, 6' -disulfonate or R-2,2 '-di (dimethylphosphine) -3,3' -di (formylphenylimine) -1,1 '-binaphthyl-6, 6' -disulfonate as a catalyst, the catalyst has unique catalytic specificity, so that the 1, 2-trichloroethane and carbonate preferentially catalyze C-O coupling reaction to generate chloroethylene carbonate, thereby being beneficial to reducing byproducts of the reaction, and leading the purity and yield of reaction products to be higher.
Preferably, the solvent comprises at least one of N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and hexamethylphosphoric triamide.
Preferably, the solvent is any one of N, N-dimethylformamide and N-methylpyrrolidone.
Preferably, the solvent is N, N-dimethylformamide.
By adopting the specific solvent as the reaction solvent, the solvents are all strong polar aprotic solvents, so that the induction effect on the reaction is more obvious, the reaction is better promoted, and the conversion rate of the reaction is higher.
Preferably, the anhydrous carbonate comprises at least one of lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, calcium carbonate, cesium carbonate.
Preferably, the anhydrous carbonate is potassium carbonate.
The substances are cheap and easily available, and at least one of the substances is used as anhydrous carbonate, so that the production cost is reduced, and the economic value of the product is higher.
Preferably, the molar ratio of the 1, 2-trichloroethane, anhydrous potassium fluoride, anhydrous carbonate and the catalyst is 1:1.05-1.1:1.02-1.05:0.002-0.005.
By controlling the molar ratio of reactants, the method is beneficial to better controlling the progress of the reaction, and simultaneously is beneficial to better improving the conversion rate of the reaction, so that the yield of the reaction is higher.
Preferably, the distillation temperature in the step 3 is 80-90 ℃, and the distillation pressure is (-0.08) - (-0.09) MPa.
Preferably, the distillation temperature in the step 4 is 100-110 ℃, and the distillation pressure is (-0.095) - (-0.098) MPa.
Preferably, the rectification temperature in the step 5 is 120-125 ℃, and the rectification pressure is (-0.095) - (-0.098) MPa.
The distillation temperature and the distillation pressure of each step are controlled, so that the solvent, byproducts and impurities in the reaction product can be removed better, and the purity of the reaction product is higher.
Preferably, the inert gas in the step 1 is nitrogen.
The nitrogen is adopted as inert gas, so that the production cost is reduced better, and the economic benefit is higher.
In a second aspect, the present application provides fluoroethylene carbonate, which adopts the following technical scheme:
fluoroethylene carbonate prepared by adopting the preparation method of fluoroethylene carbonate
The fluoroethylene carbonate prepared by the preparation method has the advantages of easy control of reaction process, easy removal of impurities, safe production operation, high yield, high purity and higher economic value.
In summary, the present application has the following beneficial effects:
1. the 1, 2-trichloroethane and the anhydrous carbonate are subjected to catalytic C-O coupling reaction under the catalysis of a catalyst and the induction of a strong polar aprotic solvent to generate chloroethylene carbonate, and meanwhile, anhydrous potassium fluoride in a reaction system is further reacted with the generated chloroethylene carbonate to obtain the fluoroethylene carbonate.
2. Because the catalyst used in the patent has unique catalytic specificity, the 1, 2-trichloroethane and carbonate react preferentially, which is beneficial to reducing byproducts of the reaction, and the purity and yield of the reaction product are higher.
3. The fluoroethylene carbonate prepared by the preparation method has the advantages of easy control of reaction process, easy removal of impurities, safe production operation, high yield, high purity and higher economic value.
Detailed Description
The present application is described in further detail below with reference to examples.
Example 1
A method for preparing fluoroethylene carbonate, comprising the following steps:
step 1, adding 300.00g of anhydrous solvent, 105.66g of anhydrous carbonate, 47.90g of anhydrous potassium fluoride and 1.60g of catalyst into a reaction bottle, filling nitrogen for replacement for 3 times, raising the temperature to 135 ℃, and then dripping 100.00g of 1, 2-trichloroethane liquid at constant temperature for 2 hours to perform reaction.
In this example, the anhydrous solvent is N, N-dimethylformamide; the anhydrous carbonate is potassium carbonate; the catalyst is R-2,2 '-di (dimethylphosphine) -3,3' -di (formylisopropylimine) -1,1 '-binaphthyl-6, 6' -disulfonic acid sodium salt. Namely, the mole ratio of 1, 2-trichloroethane, anhydrous potassium fluoride, anhydrous carbonate and catalyst is 1:1.1:1.02:0.002.
and 2, after the reaction is carried out for 2 hours in a heat preservation way, stopping the reaction, cooling to room temperature under natural conditions, opening a valve to balance the pressure in the high-pressure reaction kettle with the atmospheric pressure, discharging, filtering the reaction liquid, and taking filtrate for later use.
And 3, distilling the filtrate obtained by filtering in the step 2 at the temperature of 80-90 ℃ and the pressure of-0.08 MPa, collecting the solvent distilled out in the temperature range, and recovering and utilizing the solvent after drying.
And 4, continuously increasing the temperature to 100-110 ℃ when no liquid flows out during the distillation in the step 3, adjusting the pressure to-0.095 MPa, continuously distilling the residual filtrate in the step 3, and collecting the fraction distilled out in the secondary temperature range to obtain a crude product.
And 5, placing the crude product in a rectification bottle, regulating the rectification temperature to 120-125 ℃ and the rectification pressure to-0.095 MPa, and collecting distilled fractions to obtain fluoroethylene carbonate.
The product purified in this example had a mass of 71.48g, a conversion of 98.28%, a yield of 89.93% (excluding the front and rear fractions) and a purity of 99.99%.
Example 2
The difference from example 1 is that:
the reaction temperature in step 1 was 120℃and the 1, 2-trichloroethane dropwise addition time in step 1 was 1h.
And the addition amounts of the reactants in the step 1 are different, specifically as follows:
500.00g of N, N-dimethylformamide, 108.77g of anhydrous potassium carbonate, 47.90g of anhydrous potassium fluoride, 4.00g of R-2,2 '-bis (dimethylphosphino) -3,3' -bis (formylisopropylimine) -1,1 '-binaphthyl-6, 6' -disulfonate and 100.00g of 1, 2-trichloroethane. Namely, the mole ratio of the 1, 2-trichloroethane, the anhydrous potassium fluoride, the anhydrous potassium carbonate and the catalyst is 1:1.1:1.05:0.005.
in the step 2, the reaction is stopped after the reaction is kept for 2 hours.
The distillation temperature in the step 3 is 80-90 ℃, and the distillation pressure is-0.09 MPa.
The distillation temperature in the step 4 is 100-110 ℃, and the distillation pressure is-0.098 MPa.
The rectification temperature in the step 5 is 120-125 ℃, and the rectification pressure is-0.098 MPa.
The product purified in this example had a mass of 67.83g, a conversion of 95.02%, a yield of 85.33% and a purity of 99.99%.
Example 3
The difference from example 1 is that:
the amounts of the reactants added in step 1 are different, and specifically are as follows:
300.00g of N, N-dimethylformamide, 105.66g of anhydrous potassium carbonate, 45.72g of anhydrous potassium fluoride, 2.00g of sodium R-2,2 '-bis (dimethylphosphino) -3,3' -bis (formylisopropylimine) -1,1 '-binaphthyl-6, 6' -disulfonate and 100.00g of 1, 2-trichloroethane. Namely, the mole ratio of the 1, 2-trichloroethane, the anhydrous potassium fluoride, the anhydrous potassium carbonate and the catalyst is 1:1.05:1.02:0.0025.
the incubation reaction time of step 2 was 1h.
The product purified in this example had a mass of 72.50g, a conversion of 99.04%, a yield of 91.21% and a purity of 99.99%.
Example 4
The difference from example 1 is that:
the amounts of the reactants added in step 1 are different, and specifically are as follows:
300.00g of anhydrous solvent, 105.66g of anhydrous carbonate, 45.72g of anhydrous potassium fluoride, 2.13g of catalyst and 100.00g of 1, 2-trichloroethane.
In this example, the anhydrous solvent is N-methylpyrrolidone; the anhydrous carbonate is potassium carbonate; the catalyst is R-2,2 '-di (dimethylphosphine) -3,3' -di (formylphenyl imine) -1,1 '-binaphthyl-6, 6' -disulfonic acid sodium salt. Namely, the mole ratio of 1, 2-trichloroethane, anhydrous potassium fluoride, anhydrous carbonate and catalyst is 1:1.05:1.02:0.0025.
the incubation reaction time of step 2 was 1h.
The product purified in this example had a mass of 71.00g, a conversion of 98.23%, a yield of 89.33% and a purity of 99.99%.
Comparative example 1
The difference from example 3 is that: the catalyst was palladium acetylacetonate, and the catalyst was added in an amount of 0.43g.
The product purified in this example had a mass of 22.76g, a conversion of 32.20%, a yield of 28.63% and a purity of 95.58%.
The foregoing are all preferred embodiments of the present application, and are not intended to limit the scope of the present application in any way, therefore: all equivalent changes in structure, shape and principle of this application should be covered in the protection scope of this application.
Claims (9)
1. A preparation method of fluoroethylene carbonate is characterized in that: the method comprises the following steps:
step 1, under the protection of inert gas, adding an anhydrous solvent, anhydrous carbonate, anhydrous potassium fluoride and a catalyst into a reaction kettle, raising the temperature to 120-135 ℃, and then dripping 1, 2-trichloroethane liquid for 1-2h for reaction;
wherein the catalyst is any one of R-2,2 '-bis (dimethylphosphine) -3,3' -bis (formylisopropylimine) -1,1 '-binaphthyl-6, 6' -disulfonate or R-2,2 '-bis (dimethylphosphine) -3,3' -bis (formylphenylimine) -1,1 '-binaphthyl-6, 6' -disulfonate;
step 2, after the reaction is carried out for 1-2 hours at the temperature, stopping the reaction, cooling to the room temperature, filtering, and taking filtrate for standby;
step 3, distilling the filtrate obtained in the step 2, and removing the solvent;
step 4, when no liquid flows out in the step 3, continuously increasing the temperature and distilling the residual filtrate in the step 3 to obtain a crude product;
and 5, rectifying the crude product to obtain fluoroethylene carbonate.
2. The method for producing fluoroethylene carbonate according to claim 1, characterized in that: the solvent comprises at least one of N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and hexamethylphosphoric triamide.
3. The method for producing fluoroethylene carbonate according to claim 2, characterized in that: the solvent is any one of N, N-dimethylformamide and N-methylpyrrolidone.
4. The method for producing fluoroethylene carbonate according to claim 1, characterized in that: the anhydrous carbonate comprises at least one of lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, calcium carbonate and cesium carbonate.
5. A process for the preparation of fluoroethylene carbonate according to any one of claims 1 to 4, characterized in that: the molar ratio of the 1, 2-trichloroethane to the anhydrous potassium fluoride to the anhydrous carbonate to the catalyst is 1:1.05-1.1:1.02-1.05:0.002-0.005.
6. A process for the preparation of fluoroethylene carbonate according to any one of claims 1 to 4, characterized in that: the distillation temperature in the step 3 is 80-90 ℃, and the distillation pressure is (-0.08) - (-0.09) MPa.
7. The method for producing fluoroethylene carbonate according to claim 6, characterized in that: the distillation temperature in the step 4 is 100-110 ℃, and the distillation pressure is (-0.095) - (-0.098) MPa.
8. The method for producing fluoroethylene carbonate according to claim 7, characterized in that: the rectification temperature in the step 5 is 120-125 ℃, and the rectification pressure is (-0.095) - (-0.098) MPa.
9. A process for the preparation of fluoroethylene carbonate according to any one of claims 1 to 4, characterized in that: the inert gas in the step 1 is nitrogen.
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| CN110845467A (en) * | 2018-03-20 | 2020-02-28 | 上海华谊（集团）公司 | Production method of fluoroethylene carbonate |
| CN112321558A (en) * | 2020-11-10 | 2021-02-05 | 湖北省宏源药业科技股份有限公司 | Preparation method of fluoroethylene carbonate |
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| JP5358974B2 (en) * | 2008-02-28 | 2013-12-04 | ダイキン工業株式会社 | Method for producing fluorinated 1,3-dioxolan-2-one |
| US20120209010A1 (en) * | 2009-10-21 | 2012-08-16 | Solvay Fluor Gmbh | Method for the Manufacture of Fluorinated Ethylene Carbonates |
| CN106916136B (en) * | 2017-03-01 | 2019-06-14 | 山东永浩新材料科技有限公司 | A kind of synthetic method of fluorinated ethylene carbonate |
| CN113135888B (en) * | 2021-03-29 | 2021-11-02 | 珠海理文新材料有限公司 | Preparation method of fluoroethylene carbonate |
| CN113620924A (en) * | 2021-08-30 | 2021-11-09 | 泰兴华盛精细化工有限公司 | Rapid continuous flow synthesis process of fluoroethylene carbonate |
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| CN110845467A (en) * | 2018-03-20 | 2020-02-28 | 上海华谊（集团）公司 | Production method of fluoroethylene carbonate |
| CN112321558A (en) * | 2020-11-10 | 2021-02-05 | 湖北省宏源药业科技股份有限公司 | Preparation method of fluoroethylene carbonate |
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Effective date of registration: 20230927 Address after: No. 137, Building B, Industrial Building, Xizhong Island Petrochemical Industrial Park Management Committee, Changxing Island Economic Zone, Dalian, Liaoning Province, 116318 Patentee after: Dalian Huayi Lithium Technology Co.,Ltd. Address before: 215400 middle GCL Road, petrochemical District, taicanggang port area, Taicang City, Suzhou City, Jiangsu Province Patentee before: Suzhou Huayi New Energy Technology Co.,Ltd. |