CN105541783A - Production method of high-purity fluoroethylene carbonate - Google Patents
Production method of high-purity fluoroethylene carbonate Download PDFInfo
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- CN105541783A CN105541783A CN201510994441.2A CN201510994441A CN105541783A CN 105541783 A CN105541783 A CN 105541783A CN 201510994441 A CN201510994441 A CN 201510994441A CN 105541783 A CN105541783 A CN 105541783A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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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Abstract
The invention relates to a production method of high-purity fluoroethylene carbonate. The production method comprises the following steps of (a) performing chlorination on dry chlorine and ethylene carbonate under the irradiation of ultraviolet light, then rectifying to obtain chloroethylene carbonate; (b) placing the chloroethylene carbonate at one side of a membrane, and placing mixed liquid of organic amine and dimethyl carbonate at the other side of the membrane, performing a membrane reaction at 40 to 50 DEG C for dechloridation, performing decompression distillation to obtain vinylene carbonate; (c) performing an addition reaction on the vinylene carbonate and hydrogen fluoride, and performing decompression distillation to obtain the high-purity fluoroethylene carbonate. A by-product generated by a reaction in each step is timely excluded from the system, further complication of the reaction and a medium process is avoided, and the foundation is laid for purification; residues of reactants are completely eradicated, separating work is reduced, and the complexity and cost of the production are lowered.
Description
Technical field
The present invention relates to a kind of production method of fluorinated ethylene carbonate, be specifically related to a kind of production method of high-purity fluorinated ethylene carbonate.
Background technology
Fluorinated ethylene carbonate is the important additives material of lithium battery electrolytes, and this material can form form compact and stable organic membrane at battery surface.This organic membrane is not losing specific conductivity, under not increasing the condition of the internal resistance of cell, produce poly-alkylcarbonic acid lithium compound, this compound can effectively suppress solvent molecule and solvation lithium ion to insert in graphite, reduce the decomposition of electrolytic solution, improve the stability of graphite cathode, and then improve the charge-discharge performance of lithium cell, and lithium cell industry needs high-purity fluorinated ethylene carbonate.
The conventional production process of fluorinated ethylene carbonate has multiple: a kind of is fluorine gas and NSC 11801 direct reaction, (a fluoro thing, polyfluoro is had for thing etc. because the preparation difficulty of fluorine gas is large, reactive behavior is higher, reaction is violent, control difficulty is comparatively large, generation product is comparatively complicated, even NSC 11801 Direct Resolution is tetrafluoro-methane), the productive rate of reaction is lower, accomplish to stablize high-purity fluorinated ethylene carbonate, cost is higher and pollution is larger; Another is that chlorocarbonic acid vinyl acetate and Potassium monofluoride react, and reaction strictly will control moisture content, and Potassium monofluoride will carry out corresponding spraying dry, simultaneously, Potassium monofluoride reacts the problems such as same control overflow is high, and productive rate is low under needing to be dissolved into the anhydrous polar solvent such as acetonitrile and tetramethylene sulfone condition.If publication number is the production method that 101676282A discloses a kind of fluorinated ethylene carbonate, it directly replaces with chlorine or carries out chloro by other chlorinating agent such as SULPHURYL CHLORIDE etc., produce chlorocarbonic acid vinyl acetate, chlorocarbonic acid vinyl acetate is after polishing purification, halogen exchange reaction is carried out with fluorination reagent in suitable solvent, generate fluorinated ethylene carbonate, the productive rate of fluorinated ethylene carbonate is all less than 70%, and purity is lower.
Summary of the invention
The present invention seeks to the production method that a kind of high-purity fluorinated ethylene carbonate is provided to overcome the deficiencies in the prior art.
For achieving the above object, the technical solution used in the present invention is: a kind of production method of high-purity fluorinated ethylene carbonate, and it comprises the following steps:
A the chlorine of drying and NSC 11801 are carried out chlorination by () under the irradiation of UV-light, rectifying subsequently obtains chlorocarbonic acid vinyl acetate;
The opposite side that b described chlorocarbonic acid vinyl acetate is placed in the side of barrier film by (), the mixed solution of organic amine and methylcarbonate is placed in barrier film, carry out barrier film reaction dechlorination at 40 ~ 50 DEG C, decompression is refining to obtain vinylene carbonate;
C described vinylene carbonate and hydrogen fluoride are carried out addition reaction by (), decompression is refining.
Optimally, the volume ratio of described organic amine and described methylcarbonate is 1:1 ~ 6.
Further, described organic amine is the mixture of one or more compositions in triethylamine, thanomin, α-amino isopropyl alcohol, diethylenetriamine, methane amide and ethanamide.
Optimally, the mixed solution free ammonia content of described organic amine and methylcarbonate is less than 100ppm and water-content is less than 10ppm.
Optimally, in described step (a), the flow velocity of chlorine is 10000 ~ 20000L/h, and the flow of NSC 11801 is 30-60L/h, and ultraviolet radiation power is 5 ~ 10w/cm
2, the temperature of reaction of chlorination is 35 ~ 50 DEG C and reaction times 2 ~ 4h.
Optimally, in step (a), the temperature of described rectifying is 130 ~ 140 DEG C, and reflux ratio is 1:1 ~ 6.
Further, step (b) is with in step (c), and the absolute pressure that described decompression is refined is 0.1 ~ 200KPa, extraction temperature 35 ~ 55 DEG C.
Further, described rectifying and described decompression are refined and are all carried out in nitrogen-sealed environment, and in nitrogen, moisture content is less than 0.5ppm.
Optimally, described barrier film is Membrane Used In Chlor-alkali Cell or lithium battery diaphragm.
Optimally, in step (c), described hydrogen fluoride is dry state hydrogen fluoride, the addition reaction temperature 35 ~ 50 DEG C of itself and vinylene carbonate.
Because technique scheme is used, the present invention compared with prior art has following advantages: the production method of the high-purity fluorinated ethylene carbonate of the present invention, can carry out continuous seepage on the whole, save the time; And get rid of often walking the byproduct that reaction produces in time outside system, avoid reacting and pilot process complicated further, thus improve productive rate and the purity of product; And stopped the residual of reactant, decrease mask work, reduce complicacy and the cost of production, the key technical index such as moisture are controlled to lower level.
Embodiment
The production method of the high-purity fluorinated ethylene carbonate of the present invention, it comprises the following steps: the chlorine of drying and NSC 11801 are carried out chlorination by (a) under the irradiation of UV-light, and rectifying subsequently obtains chlorocarbonic acid vinyl acetate; The opposite side that b described chlorocarbonic acid vinyl acetate is placed in the side of barrier film by (), the mixed solution of organic amine and methylcarbonate is placed in barrier film, carry out barrier film reaction dechlorination at 40 ~ 50 DEG C, decompression is refining to obtain vinylene carbonate; C described vinylene carbonate and hydrogen fluoride are carried out addition reaction by (), decompression is refining.All carry out purification operations after each step, and the secondary pollution introduced in purification process can be avoided, the byproduct often walking reaction generation is got rid of in time outside system, avoid reacting and pilot process complicated further, laying the foundation for purifying, the key technical index such as moisture can be controlled to lower level simultaneously; And adopt ion diaphragm to carry out dechlorination, stop the residual of reactant, decreased mask work, reduce complicacy and the cost of production.Compared with prior art, the method can obtain higher-quality target product with lower energy consumption, higher productive rate.
The volume ratio of described organic amine and described methylcarbonate is preferably 1:1 ~ 6, and described organic amine can select conventional those, as the mixture of one or more compositions in triethylamine, thanomin, α-amino isopropyl alcohol, diethylenetriamine, methane amide and ethanamide; The mixed solution free ammonia content of the organic amine selected and methylcarbonate is preferably less than 100ppm and water-content is less than 10ppm; What these measures all can improve dechlorination reaction carries out degree.In step (a), the flow velocity of chlorine is preferably 10000 ~ 20000L/h, and the flow of NSC 11801 is preferably 30-60L/h, and ultraviolet radiation power is preferably 5 ~ 10w/cm
2, the temperature of reaction of chlorination is preferably 35 ~ 50 DEG C and the reaction times is preferably 2 ~ 4h; The wavelength region of UV-light is 10nm ~ 400nm, and it can adopt fluorescent lamp, high voltage mercury lamp and other all kinds ultraviolet source.And the temperature of rectifying is preferably 130 ~ 140 DEG C, reflux ratio is preferably 1:1 ~ 6, and obtainable like this chlorocarbonic acid vinyl acetate purity is greater than 99.9%wt, and wherein the content of water is less than 1ppm.In step (a), the refining absolute pressure of described decompression is 0.1 ~ 200KPa, and extraction temperature 35 ~ 55 DEG C, can obtain high-purity vinylene carbonate that purity is greater than 99.9wt% like this, and wherein moisture content is less than 10ppm and free chlorine contents is less than 5ppm.Rectifying and decompression are refined and are all carried out in totally-enclosed environment (high pure nitrogen sealed environment), and in high pure nitrogen, moisture content is less than 0.5ppm, thus the key technical index such as moisture are controlled to lower level, guarantees the quality of product.Ion diaphragm is Membrane Used In Chlor-alkali Cell or lithium battery diaphragm, as perfluorocarboxylic acid film, 800 series high-performance perfluorocarboxylic acid perfluor sulfonic acid composite membranes of Japan AGC company, the perfluorinated ionic membrane etc. of Eastern Mountain, Shandong group of 900 series high-performance perfluorocarboxylic acid perfluor sulfonic acid composite membranes of E.I.Du Pont Company, Japanese Asahi Kasei Corporation, or the microporous polyolefin film such as polyethylene, polypropylene.In step (c), described hydrogen fluoride is high-purity dry state hydrogen fluoride (water-content is less than 10ppm), and the addition reaction temperature of itself and vinylene carbonate is preferably 35 ~ 50 DEG C.
Below in conjunction with embodiment, the present invention is further described.
Embodiment 1
The present embodiment provides a kind of continuous production method of fluoro ethylene carbonate with high purity, and it comprises the following steps:
A flow velocity is the dry chlorine gas of 10000L/h and flow by () is that the NSC 11801 of 30L/h is at UV-light (100 ~ 200nm, 7.5w/cm
2) irradiation under carry out chlorination in 35 DEG C, react 3 hours; Subsequently 130 DEG C, under the condition of reflux ratio 1:1 rectifying obtain chlorocarbonic acid vinyl acetate;
B chlorocarbonic acid vinyl acetate is placed in the side of barrier film by (), and the mixed solution of triethylamine and methylcarbonate (this mixed solution free ammonia content is less than 100ppm, and water-content is less than 10ppm; The volume ratio of triethylamine and methylcarbonate is 1:1.2, the volume ratio of chlorocarbonic acid vinyl acetate and mixed solution is 1:1) be placed in the opposite side of barrier film, carry out barrier film reaction dechlorination at 40 DEG C, 35 DEG C, under the condition of 150KPa decompression refine and obtain the vinylene carbonate that purity is greater than 99.9wt%;
C vinylene carbonate and high-purity dry state hydrogen fluoride (water-content is less than 10ppm) are carried out addition reaction at 35 DEG C by (), subsequently 35 DEG C, decompression is refining under the condition of 150KPa removes excessive hydrogen fluoride, obtain purity and be greater than 99.9wt% and water-content is less than the fluorinated ethylene carbonate of 4.2ppm, productive rate is greater than 85%(in chlorocarbonic acid vinyl acetate); Above-mentioned rectifying, decompression treating process all adopt totally-enclosed purification process, and this technique adopts high pure nitrogen sealed environment, and high pure nitrogen moisture content is less than 0.5ppm.
Embodiment 2 to 5
Embodiment 2 to embodiment 5 provides a kind of continuous production method of fluoro ethylene carbonate with high purity respectively, their step and substantially identical in embodiment 1, inconsistent unlike its design parameter, as shown in table 1.
The design parameter of fluoro ethylene carbonate with high purity continuous production method in table 1 embodiment 2 to embodiment 5
Comparative example 1
Be embodiment in 101676282A 1 with reference to publication number and implement profit 2, be specially: in the 2000ml glass reaction bottle of drying, add 1350g NSC 11801, reacting by heating system, when temperature in reaction system reaches 80 DEG C, start the SULPHURYL CHLORIDE dripping 1700ml, and in reaction process, add the AIBN that total amount is 4.2g in batches, SULPHURYL CHLORIDE added in 5 hours, in the dropping process of SULPHURYL CHLORIDE, temperature of reaction system remains on 80 ~ 85 DEG C, drips and terminates rear continuation stirring reaction 1 hour.Reaction terminates rear cooling, and products in water washs, and is neutralized to system in neutral with sodium carbonate, separates organic layer, with anhydrous magnesium sulfate drying, filters, and the method for shunting of reducing pressure in filtrate collects the cut of 120 ~ 122 DEG C/22mmHg, is chlorocarbonic acid vinyl acetate.250ml(375g is added in the 1500ml there-necked flask of drying) chlorocarbonic acid vinyl acetate, add 500ml methyl-sulphoxide simultaneously, 250g Potassium monofluoride, reacting by heating, react 15 hours at 90 DEG C, after reaction terminates, cooling, filtration, with chlorocarbonic acid vinyl acetate timing productive rate for 56.48%, and purity is 95.5%.
Above-described embodiment is only for illustrating technical conceive of the present invention and feature; its object is to person skilled in the art can be understood content of the present invention and implement according to this; can not limit the scope of the invention with this; all equivalences done according to spirit of the present invention change or modify, and all should be encompassed within protection scope of the present invention.
Claims (10)
1. a production method for high-purity fluorinated ethylene carbonate, is characterized in that, it comprises the following steps:
A the chlorine of drying and NSC 11801 are carried out chlorination by () under the irradiation of UV-light, rectifying subsequently obtains chlorocarbonic acid vinyl acetate;
The opposite side that b described chlorocarbonic acid vinyl acetate is placed in the side of barrier film by (), the mixed solution of organic amine and methylcarbonate is placed in barrier film, carry out barrier film reaction dechlorination at 40 ~ 50 DEG C, decompression is refining to obtain vinylene carbonate;
C described vinylene carbonate and hydrogen fluoride are carried out addition reaction by (), decompression is refining.
2. the production method of high-purity fluorinated ethylene carbonate according to claim 1, is characterized in that: the volume ratio of described organic amine and described methylcarbonate is 1:1 ~ 6.
3. the production method of high-purity fluorinated ethylene carbonate according to claim 1 and 2, is characterized in that: described organic amine is the mixture of one or more compositions in triethylamine, thanomin, α-amino isopropyl alcohol, diethylenetriamine, methane amide and ethanamide.
4. the continuous production method of high-purity fluorinated ethylene carbonate according to claim 3, is characterized in that: the mixed solution free ammonia content of described organic amine and methylcarbonate is less than 100ppm and water-content is less than 10ppm.
5. the continuous production method of high-purity fluorinated ethylene carbonate according to claim 1, it is characterized in that: in described step (a), the flow velocity of chlorine is 10000 ~ 20000L/h, and the flow of NSC 11801 is 30-60L/h, and ultraviolet radiation power is 5 ~ 10w/cm
2, the temperature of reaction of chlorination is 35 ~ 50 DEG C and reaction times 2 ~ 4h.
6. the continuous production method of high-purity fluorinated ethylene carbonate according to claim 1, is characterized in that: in step (a), and the temperature of described rectifying is 130 ~ 140 DEG C, and reflux ratio is 1:1 ~ 6.
7. the continuous production method of the high-purity fluorinated ethylene carbonate according to claim 1 or 6, is characterized in that: step (b) is with in step (c), and the absolute pressure that described decompression is refined is 0.1 ~ 200KPa, extraction temperature 35 ~ 55 DEG C.
8. the continuous production method of high-purity fluorinated ethylene carbonate according to claim 7, is characterized in that: described rectifying and described decompression are refined and all carried out in nitrogen-sealed environment, and in nitrogen, moisture content is less than 0.5ppm.
9. the continuous production method of high-purity fluorinated ethylene carbonate according to claim 1, is characterized in that: described barrier film is Membrane Used In Chlor-alkali Cell or lithium battery diaphragm.
10. the continuous production method of high-purity fluorinated ethylene carbonate according to claim 1, is characterized in that: in step (c), and described hydrogen fluoride is dry state hydrogen fluoride, the addition reaction temperature 35 ~ 50 DEG C of itself and vinylene carbonate.
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Cited By (9)
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| CN109134421A (en) * | 2018-02-26 | 2019-01-04 | 江苏长园华盛新能源材料有限公司 | The method of vinylene carbonate is recycled from fluorinated ethylene carbonate front-end volatiles |
| CN112500388A (en) * | 2020-12-21 | 2021-03-16 | 苏州华一新能源科技有限公司 | Preparation method of fluorine-containing ethylene carbonate |
| CN113105429A (en) * | 2021-03-26 | 2021-07-13 | 珠海理文新材料有限公司 | Synthetic method of fluoroethylene carbonate |
| CN113896705A (en) * | 2021-11-09 | 2022-01-07 | 青岛科技大学 | Synthetic method for co-production of 1-fluoro-2-chloroethylene carbonate and 1, 2-difluoroethylene carbonate |
| CN115433155A (en) * | 2022-09-25 | 2022-12-06 | 青岛科技大学 | Synthetic method of fluoroethylene carbonate |
| CN115466242A (en) * | 2022-10-03 | 2022-12-13 | 青岛科技大学 | Synthetic method of fluoroethylene carbonate |
| CN115611845A (en) * | 2022-09-20 | 2023-01-17 | 大连华一锂电科技有限公司 | Continuous production process of chlorinated ethylene carbonate |
| CN115626907A (en) * | 2022-11-03 | 2023-01-20 | 多氟多新材料股份有限公司 | Preparation method of 4-trifluoromethyl vinyl carbonate |
| CN115925669A (en) * | 2022-11-21 | 2023-04-07 | 青岛科技大学 | Preparation method of fluoro ethylene carbonate |
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Cited By (12)
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|---|---|---|---|---|
| CN109134421A (en) * | 2018-02-26 | 2019-01-04 | 江苏长园华盛新能源材料有限公司 | The method of vinylene carbonate is recycled from fluorinated ethylene carbonate front-end volatiles |
| CN112500388A (en) * | 2020-12-21 | 2021-03-16 | 苏州华一新能源科技有限公司 | Preparation method of fluorine-containing ethylene carbonate |
| CN113105429A (en) * | 2021-03-26 | 2021-07-13 | 珠海理文新材料有限公司 | Synthetic method of fluoroethylene carbonate |
| CN113896705A (en) * | 2021-11-09 | 2022-01-07 | 青岛科技大学 | Synthetic method for co-production of 1-fluoro-2-chloroethylene carbonate and 1, 2-difluoroethylene carbonate |
| CN115611845A (en) * | 2022-09-20 | 2023-01-17 | 大连华一锂电科技有限公司 | Continuous production process of chlorinated ethylene carbonate |
| CN115611845B (en) * | 2022-09-20 | 2024-06-11 | 大连华一锂电科技有限公司 | Continuous production process of chloroethylene carbonate |
| CN115433155A (en) * | 2022-09-25 | 2022-12-06 | 青岛科技大学 | Synthetic method of fluoroethylene carbonate |
| CN115466242A (en) * | 2022-10-03 | 2022-12-13 | 青岛科技大学 | Synthetic method of fluoroethylene carbonate |
| CN115466242B (en) * | 2022-10-03 | 2024-06-21 | 青岛科技大学 | Synthetic method of fluoroethylene carbonate |
| CN115626907A (en) * | 2022-11-03 | 2023-01-20 | 多氟多新材料股份有限公司 | Preparation method of 4-trifluoromethyl vinyl carbonate |
| CN115626907B (en) * | 2022-11-03 | 2024-04-16 | 多氟多新材料股份有限公司 | Preparation method of 4-trifluoro methyl ethylene carbonate |
| CN115925669A (en) * | 2022-11-21 | 2023-04-07 | 青岛科技大学 | Preparation method of fluoro ethylene carbonate |
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Application publication date: 20160504 |