CN115772151A - Preparation method of 4-fluoro-1,3-dioxolane-2-one - Google Patents
Preparation method of 4-fluoro-1,3-dioxolane-2-one Download PDFInfo
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Abstract
The invention relates to the field of preparation of fluorine-containing compounds, and discloses a preparation method of 4-fluoro-1,3-dioxolane-2-one, wherein ethylene carbonate dissolved in a solvent reacts with fluoride under the action of a strong alkaline substance to obtain fluoroethylene carbonate, namely 4-fluoro-1,3-dioxolane-2-one. The fluoroethylene carbonate is obtained by taking ethylene carbonate and a proper fluorinating reagent as raw materials and reacting in a one-pot method in the presence of a strong alkaline substance, so that the chlorination step of the conventional main process is omitted, the process is simple, the reaction is safe and controllable, the yield is high, and the method is very favorable for large-scale production.
Description
Technical Field
The invention relates to a preparation method of 4-fluoro-1,3-dioxolane-2-one, belonging to the field of preparation of fluorine-containing compounds.
Background
Fluoroethylene carbonate (4-fluoro-1,3-dioxolane-2-one, FEC) is a colorless transparent liquid at normal temperature, can be used as an intermediate of medicines and pesticides, and is mainly applied as an important additive of lithium ion battery electrolyte at present. The FEC can inhibit the decomposition of partial electrolyte, and a layer of SEI film with excellent performance is formed, so that the impedance of the battery is reduced, the specific capacity of the battery can be obviously improved, and the cycling stability of the battery is improved. In addition, fluoroethylene carbonate also has a flame retardant effect, so that the safety of the battery is greatly improved by using FEC as an additive of lithium ion battery electrolyte, and the development of a green and low-cost FEC synthesis method is particularly important under the large background of double carbons in national implementation.
The synthesis route of FEC is more, for example, the industrial production of FEC is carried out by directly adopting a method of fluorine gas to fluorinate and replace ethylene carbonate. Chinese patent CN113121491A and Japanese patent JP2000-309583 describe a compound represented by F 2 Or F 2 /N 2 The mixed gas directly carries out fluorine substitution reaction on the Ethylene Carbonate (EC) under the conditions of ultraviolet light and the like to obtain the fluoroethylene carbonate. However, because fluorine gas has extremely strong activity, the reaction is difficult to control in the production process, and fluoroethylene carbonate further performs fluorine substitution reaction in the reaction process to generate a plurality of polyfluorinated byproducts, thereby reducing the product yield and increasing the difficulty of product purification. In addition, the method has very high requirements on production equipment and production process, the fluorine gas has strong toxicity, excessive fluorine gas causes great pollution to the environment, and the post-treatment is difficult.
The method for synthesizing FEC by halogen exchange is also a common method at present, namely vinyl carbonate is taken as a raw material, and chlorination is carried out to obtain chloroethylene carbonate in two steps, and then fluorination is carried out to obtain a target product FEC; or directly fluorinating the chloroethylene carbonate to obtain FEC. Chinese patent No. CN103113345a describes that chloroethylene carbonate and hydrogen fluoride are used as raw materials, and are reacted under the protection of nitrogen to obtain a mixture of fluoroethylene carbonate, and then the mixture is distilled and purified to obtain fluoroethylene carbonate. The method has the advantages of no generation of solid waste, simple process route, absorption of waste gas hydrogen fluoride and hydrogen chloride by alkali liquor, basically no environmental pollution and product yield of more than 95 percent. However, the use of hydrogen fluoride gas is highly dangerous and corrosive, and the method is disadvantageous in that the reaction temperature is high and the reaction time is long. Chinese patent CN101210005A describes that chloroethylene carbonate and fluoride (sodium fluoride and the like) are used as raw materials, a phase transfer catalyst (crown ether or polyethylene glycol) is added for reaction to obtain a fluoroethylene carbonate mixture, and the mixture is subjected to solid-liquid separation and rectification purification to obtain fluoroethylene carbonate with the required purity. It has been found by way of comparative example that the use of a phase transfer catalyst allows the reaction to proceed more quickly and more thoroughly. However, the method has low yield of only about 55 percent, and the catalyst price is still relatively high, thus leading to higher production cost. In addition, the electrolytic fluorination method is also one of the methods for synthesizing FEC. Chinese patent CN104328455a describes that an anhydrous hydrogen fluoride solution of ethylene carbonate is subjected to electrolytic fluorination, after the reaction is finished, the electrolyte is fully stood, the product deposited from the bottom of the electrolytic cell is a fluoroethylene carbonate crude product, and fluoroethylene carbonate is obtained after reduced pressure distillation. The obvious disadvantages of the method are that the cost is extremely high, the requirement on equipment is extremely high, and the large-scale production is difficult to realize compared with other methods.
Disclosure of Invention
The invention aims to provide a preparation method of 4-fluoro-1,3-dioxolane-2-one, which has the advantages of simple reaction process, high product yield, easily controlled reaction rate and suitability for industrial amplification.
In order to achieve the above purpose, the invention provides the following technical scheme:
a preparation method of 4-fluoro-1,3-dioxolane-2-ketone is characterized in that ethylene carbonate dissolved in a solvent reacts with fluoride under the action of a strong alkaline substance to obtain fluoroethylene carbonate.
Preferably, the solvent is one or more of tetrahydrofuran, diethyl ether, ethylene glycol dimethyl ether, triethylene glycol dimethyl ether and tetraethylene glycol dimethyl ether, cyclopentyl methyl ether, tert-butyl methyl ether, toluene and xylene, and more preferably one or more of tetrahydrofuran, ethylene glycol dimethyl ether and cyclopentyl methyl ether.
Preferably, the molar ratio of the ethylene carbonate to the fluoride is 1:0.3 to 5, preferably 1:1 to 1.5.
Preferably, the fluoride is selected from one or more of 1,3,2-benzodithiazole, 2-fluoro-, 1,1,3,3-tetraoxide (N-fluoro-orthophthalimide, NFOBS), N-fluorobenzenesulfonylimide (NFSI), 1-chloromethyl-4-fluoro-1,4-diazotized bicyclic 2.2.2 octane bis (tetrafluoroborate) salt (Selectfluor), N-fluoropyridinium heptafluorodiboron ester (NFPy), and N, N '-difluoro-2,2' -bipyridinium bistetrafluoroborate.
Preferably, the strong alkaline substance is one or a mixture of Lithium Diisopropylamide (LDA), calcium hydride and sodium hydride, and more preferably LDA. Preferably, the molar ratio of the ethylene carbonate to the strongly basic substance is 1:1 to 1.3, more preferably 1:1 to 1.2. The reaction rate can be effectively controlled under low temperature and strong alkaline conditions, the reaction is stably and safely promoted, and the reaction conditions are safe and controllable.
Preferably, the reaction temperature is-85 to 0 ℃, more preferably-60 to-20 ℃. The invention has low reaction temperature, can stabilize the activity of the generated intermediate and is beneficial to the stable operation of the fluorination reaction.
Preferably, the reaction time is 2 to 16 hours, more preferably 2 to 10 hours.
Preferably, the reaction is carried out under an inert atmosphere, and the gas inside the reactor is replaced with an inert gas before the reaction, and the inert gas is nitrogen or argon, more preferably high-purity nitrogen.
Preferably, the preparation method comprises the steps of dissolving ethylene carbonate in a solvent, pre-reacting the ethylene carbonate with a strong base substance for a certain time, and then adding fluoride to perform a fluorination reaction. Preferably, the pre-reaction time is 1-5 h, and the pre-reaction temperature is-80 to-10 ℃. The time of the fluorination reaction is 5 to 8 hours, and the temperature of the fluorination reaction is minus 80 to minus 10 ℃.
In the preparation method of fluoroethylene carbonate, ethylene carbonate and a proper fluorination reagent are used as raw materials, and fluoroethylene carbonate is synthesized under the action of a proper amount of strong alkaline substances. The method has the advantages of simple synthesis process, high reaction conversion rate, high product yield, easily controlled reaction rate, high product purity of over 99.9 percent after simple post-treatment, and suitability for large-scale industrial production.
The invention has the beneficial effects that:
compared with the prior art, the preparation method of fluoroethylene carbonate provided by the invention has the following advantages:
1. the invention selects the fluorinating reagent and the ethylene carbonate to directly synthesize the fluoroethylene carbonate, omits the complicated steps of firstly generating the chloroethylene carbonate and then using the fluorinating reagent in the prior art, greatly shortens the reaction time, saves the cost, reduces the introduction of chloride ion impurities, and improves the conversion rate of the ethylene carbonate.
2. Compared with other direct fluorination methods, the fluorination reagent adopted by the invention has no toxicity, less influence on the environment, no corrosivity, less damage to reaction equipment, safety and controllability.
3. The content of chloride ions in the prepared fluoroethylene carbonate is less than 2 ppm.
Detailed Description
In order to further illustrate the present invention, the following examples are provided to describe the preparation method of fluoroethylene carbonate provided by the present invention in detail.
Example 1
A2L glass flask used for the reaction is firstly replaced and cleaned by nitrogen, then 500g of ethylene carbonate is added into the flask and dissolved by a proper amount of tetrahydrofuran solvent, 620g of LDA is added at the reaction temperature of-80 ℃ for pre-reaction for 2 hours (the molar ratio EC: LDA = 1:1), and then 1,3,2-benzodithiazole, 2-fluorine-, 1,1,3,3-tetraoxide (N-fluorine-o-phenylenedisulfonyl imide, NFOBS) is continuously added for reaction. The molar ratio of ethylene carbonate to NFOBS is 1: and (3) 1.5, reacting for 8 hours, purging the reaction system through positive pressure protection of nitrogen, and then introducing paraffin oil for liquid seal. The reaction liquid is distilled and rectified to obtain the fluoroethylene carbonate product, wherein the yield is 97.33 percent, and the purity is 99.95 percent.
Example 2
A 2L glass flask used for the reaction was first purged with nitrogen gas, and then 500g of ethylene carbonate was added to the flask and dissolved in an appropriate amount of tetrahydrofuran solvent, and 740g of LDA was added at a reaction temperature of-60 ℃ for pre-reaction for 3 hours (molar ratio EC: LDA = 1.2), followed by continuous addition of N-fluorobenzenesulfonylimide (NFSI) for reaction. The molar ratio of ethylene carbonate to N-fluorobenzenesulfonylimide (NFSI) is 1:1.2, reacting for 6h, purging the reaction system through positive pressure protection of nitrogen, and then introducing paraffin oil for liquid seal. The reaction liquid is distilled and rectified to obtain the fluoroethylene carbonate product, wherein the yield is 94.16 percent, and the purity is 99.90 percent.
Example 3
Firstly, a 2L glass flask used for the reaction is replaced and cleaned by nitrogen, then 500g of ethylene carbonate is added into the flask, and dissolved by a proper amount of glycol dimethyl ether solvent, 240g of calcium hydride is added at the reaction temperature of-20 ℃ for pre-reaction for 1 hour (the molar ratio EC: caH) 2 =1: 1) Followed by the addition of 1-chloromethyl-4-fluoro-1,4-diazotized bicyclo 2.2.2 octane bis (tetrafluoroborate) salt (Selectfluor) continuously. The molar ratio of ethylene carbonate and 1-chloromethyl-4-fluoro-1,4-diazotized bicyclo 2.2.2 octane bis (tetrafluoroborate) salt (Selectfluor) was 1: and 1.3, reacting for 8 hours, purging the reaction system through positive pressure protection of nitrogen, and then introducing paraffin oil for liquid seal. The reaction solution is distilled and rectified to obtain the fluoroethylene carbonate product, wherein the yield is 97.85 percent, and the purity is 99.95 percent.
Example 4
A2L glass flask used for the reaction was first purged with nitrogen, then 500g of ethylene carbonate was charged into the flask, dissolved in an appropriate amount of cyclopentyl methyl ether solvent, and pre-reacted for 5 hours with 651g of LDA added at-70 deg.C (molar ratio EC: LDA = 1.07), followed by continuous addition of N-fluoropyridinium heptafluorodiboron ester (NFPy). The molar ratio of ethylene carbonate to N-fluoropyridinium heptafluorodiboron (NFPy) was 1:1.1, reacting for 5h, purging the reaction system through positive pressure protection of nitrogen, and then introducing paraffin oil for liquid seal. The reaction solution is distilled and rectified to obtain the fluoroethylene carbonate product, the yield is 96.42 percent, and the purity is 99.92 percent.
Example 5
First, a 2L glass flask used for the reaction was purged with nitrogen gas, then 500g of ethylene carbonate was added to the flask and dissolved in an appropriate amount of tetrahydrofuran solvent, and 140g of sodium hydride was added at a reaction temperature of-20 ℃ to pre-react for 2 hours (molar ratio EC: naH = 1.02), followed by continuous addition of N, N '-difluoro-2,2' -bipyridine bistetrafluoroborate to react. The molar ratio of ethylene carbonate to N, N '-difluoro-2,2' -bipyridine bistetrafluoroborate is 1:1.1, reacting for 6h, purging the reaction system through positive pressure protection of nitrogen, and then introducing paraffin oil for liquid seal. The reaction liquid is distilled and rectified to obtain the fluoroethylene carbonate product, wherein the yield is 95.57 percent, and the purity is 99.93 percent.
Example 6
A2L glass flask used for the reaction is replaced and cleaned by nitrogen, 500g of ethylene carbonate is added into the flask, dissolved by a proper amount of tetrahydrofuran solvent, and added with 252g of calcium hydride for pre-reaction for 2 hours at the reaction temperature of-10 ℃ (the molar ratio EC: caH) 2 =1:1.05 1,3,2-benzodithiazole, 2-fluoro-, 1,1,3,3-tetraoxide (N-fluoro-phthalimide, NFOBS) was added continuously for reaction. Ethylene carbonate and 1,3,2-benzodithiazole, 2-fluoro-, 1,1,3,3-tetraoxide (N-fluoro-phthalimide, NFOBS) in a molar ratio of 1: and (3) 1.2, reacting for 8 hours, purging the reaction system through positive pressure protection of nitrogen, and then introducing paraffin oil for liquid seal. The reaction solution is distilled and rectified to obtain the fluoroethylene carbonate product, wherein the yield is 97.45 percent, and the purity is 99.94 percent.
Comparative example 1
Firstly, a 2L glass flask used for the reaction is replaced and cleaned by nitrogen, then 500g of ethylene carbonate is added into the flask, and dissolved by a proper amount of tetrahydrofuran solvent, and 1,3,2-benzodithiazole, 2-fluoro-, 1,1,3,3-tetraoxide (N-fluoro-o-phenylenedisulfonyl imide, NFOBS) is continuously added for reaction at the reaction temperature of-10 ℃. Ethylene carbonate and 1,3,2-benzodithiazole, 2-fluoro-, 1,1,3,3-tetraoxide (N-fluoro-phthalimide, NFOBS) in a molar ratio of 1:1.2, the reaction time is 8h, and the yield of fluoroethylene carbonate is 8.12%; the reaction time is 20h, and the yield of the fluoroethylene carbonate is 14.77%.
Comparative example 2
Firstly, a 2L glass flask used for the reaction is replaced and cleaned by nitrogen, then 500g of ethylene carbonate is added into the flask, dissolved by a proper amount of tetrahydrofuran solvent, and continuously added with 1,3,2-benzodithiazole, 2-fluoro-, 1,1,3,3-tetraoxide (N-fluoro-o-phenylenedisulfonyl imide, NFOBS) for reaction at the reaction temperature of 50 ℃. Ethylene carbonate and 1,3,2-benzodithiazole, 2-fluoro-, 1,1,3,3-tetraoxide (N-fluoro-phthalimide, NFOBS) in a molar ratio of 1:1.2, the reaction time is 8 hours, and the yield of fluoroethylene carbonate is 10.41 percent; the reaction time is 20 hours, and the yield of fluoroethylene carbonate is 18.52 percent.
Comparative example 3
A2L glass flask used for the reaction was first purged with nitrogen, then 100g of ethylene carbonate was added to the flask, 390g N-fluorobenzenesulfonylimide (NFSI) was added thereto, and stirred uniformly. The reaction time is 1.2h at 120 ℃, and the fluoroethylene carbonate product is obtained by distilling and rectifying the reaction liquid, with the yield of 6.53%. The reaction time is 5 hours, and the yield of fluoroethylene carbonate is 13.57%.
Comparative example 4
First, a 2L glass flask used for the reaction is cleaned by nitrogen displacement, then 500g of ethylene carbonate is added into the flask, dissolved by a proper amount of ethylene glycol dimethyl ether solvent, and added with 240g of calcium hydride for pre-reaction for 1 hour at the reaction temperature of 120 ℃ (molar ratio EC: caH) 2 =1: 1) Followed by the addition of 1-chloromethyl-4-fluoro-1,4-diazotized bicyclo 2.2.2 octane bis (tetrafluoroborate) salt (Selectfluor) continuously. The molar ratio of ethylene carbonate and 1-chloromethyl-4-fluoro-1,4-diazotized bicyclo 2.2.2 octane bis (tetrafluoroborate) salt (Selectfluor) was 1: and 1.3, reacting for 8 hours, purging the reaction system through positive pressure protection of nitrogen, and then introducing paraffin oil for liquid seal. The reaction liquid is distilled and rectified to obtain the fluoroethylene carbonate product with the yield of 15.86 percent.
As can be seen from the above examples and comparative examples, the high temperature is not favorable for the production of fluoroethylene carbonate. The invention firstly uses the strong alkaline substance to treat the ethylene carbonate, can improve the reaction activity of the ethylene carbonate, reduces the reaction barrier of the fluorination reagent fluorinated ethylene carbonate to fluorinated ethylene carbonate, and obtains higher yield.
The foregoing is directed to preferred embodiments of the present invention, other and further embodiments of the invention may be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow. However, any simple modification, equivalent change and modification of the above embodiments according to the technical essence of the present invention are within the protection scope of the technical solution of the present invention.
Claims (10)
1. A preparation method of 4-fluoro-1,3-dioxolane-2-ketone is characterized in that ethylene carbonate dissolved in a solvent reacts with fluoride under the action of a strong alkaline substance to obtain fluoroethylene carbonate.
2. The preparation method according to claim 1, wherein the solvent is one or more of tetrahydrofuran, diethyl ether, ethylene glycol dimethyl ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, cyclopentyl methyl ether, tert-butyl methyl ether, toluene and xylene.
3. The preparation method according to claim 1, characterized in that the molar ratio of ethylene carbonate to fluoride is 1:0.3 to 5, preferably 1:1 to 1.5.
4. The method of claim 1, wherein the fluoride is selected from one or more of 1,3,2-benzodithiazole, 2-fluoro-, 1,1,3,3-tetraoxide, N-fluorobenzenesulfonylimide, 1-chloromethyl-4-fluoro-1,4-diazotized bicyclic 2.2.2 octane bis (tetrafluoroborate) salt, N-fluoropyridinium heptafluorodiboron ester, N '-difluoro-2,2' -bipyridinium bistetrafluoroborate.
5. The preparation method according to claim 1, wherein the strongly basic substance is one or more of lithium diisopropylamide, calcium hydride and sodium hydride.
6. The method according to claim 1, wherein the molar ratio of the ethylene carbonate to the strongly basic substance is 1:1 to 1.3.
7. The process according to claim 1, wherein the reaction temperature is-85 to 0 ℃, preferably-60 to-20 ℃.
8. The process according to claim 1, wherein the reaction time is between 2 and 16 hours, preferably between 2 and 10 hours.
9. The method of claim 1, wherein the reaction is carried out under an inert atmosphere.
10. The preparation method according to any one of claims 1 to 9, wherein ethylene carbonate is dissolved in a solvent, pre-reacted with a strong basic substance, and then added with fluoride to perform a fluorination reaction; the pre-reaction time is 1-5 h, and the pre-reaction temperature is-80 to-10 ℃; the time of the fluorination reaction is 5 to 8 hours, and the temperature of the fluorination reaction is-80 to-10 ℃.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117247368A (en) * | 2023-11-20 | 2023-12-19 | 上海如鲲新材料股份有限公司 | Preparation method of trans-difluoro ethylene carbonate compounds |
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