CN115259112A - Production method of bis-fluorosulfonyl imide and lithium salt thereof - Google Patents
Production method of bis-fluorosulfonyl imide and lithium salt thereof Download PDFInfo
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Abstract
The invention discloses a production method of difluoride sulfimide and lithium salt thereof, belonging to the technical field of difluoride sulfimide and lithium salt thereof, and comprising the following steps: (1) Under the nitrogen atmosphere, taking sulfuryl chloride fluoride as a raw material, introducing ammonia gas in an aprotic solvent under the action of an organic basic catalyst to obtain an alkaline reaction solution of the difluoride sulfimide, carrying out reduced pressure distillation to recover the solvent, washing the obtained reaction concentrated solution, and directly using the reaction concentrated solution for the next lithiation reaction without further purification; (2) Adding a solvent into the reaction liquid obtained in the step (1) for dissolving, adding a lithium salt in a nitrogen atmosphere, stirring for reacting, and purifying to obtain lithium bis (fluorosulfonyl) imide; the method has the advantages of high yield, good purity, safety and high efficiency.
Description
Technical Field
The invention relates to a method for producing difluoride sulfimide and lithium salt thereof.
Background
In recent years, with the national support of the new energy automobile industry and the rapid development of the new energy automobile market, the lithium ion power battery industry is rapidly advancing on a high-quality development road. Currently, liPF is used in consideration of battery cost, safety performance, and the like6(lithium hexafluorophosphate) is the lithium solute salt of lithium batteries which is most widely used commercially, but in use, liPF6The problems of poor thermal stability, easy hydrolysis and the like exist, the capacity of the battery is rapidly attenuated, and potential safety hazards are brought. For many years, the lithium battery industry has continued to search for new materials to optimize electrolyte performance. Under the environment, the novel electrolyte solute LiFSI (lithium bis (fluorosulfonyl imide)) with the advantages of better thermal stability, hydrolysis resistance and the like is a novel lithium salt with the current industrial prospect, and becomes the core competitiveness of lithium battery enterprises in the high-nickel age.
Early LiFSI was synthesized in the laboratory from sulfamic acid and phosphorus pentachloride by multiple reactions (J.K. Ruff et al, inorg. Synth.1968,11, 138). The process has complex route, various intermediate products and difficult product extraction, so that the production difficulty is high, the production cost is high, and the commercial use of the process is restricted. In recent years, with the breakthrough of LiFSI production technology and the cost reduction, liFSI has been the condition for industrial production and large-scale commercial application.
At present, liFSI is applied to the synthesis route of production, and the synthesis process is divided into two main routes:
the first synthesis route is based on the optimization of the traditional synthesis process, and comprises the steps of synthesizing the bis-chlorosulfonyl imide (HClSI) by changing the selection of raw materials and taking chlorosulfonic acid and sulfamic acid or chlorosulfonyl isocyanate as raw materials, then synthesizing the bis-fluorosulfonyl imide (HFSI) by fluorination, and finally obtaining LiFSI (for example: CN105731399B, CN 106044728B) by three-step reaction through lithiation. Compared with the traditional process, the optimized process reduces the reaction steps and the types of reaction products, obviously reduces the production difficulty and the production cost compared with the traditional process, and most enterprises such as polyfluoride and the like use the process to produce LiFSI at present. However, the production process still needs to synthesize the lithium bis (fluorosulfonyl) imide through three steps of reaction, and the single-step yield of the first step of synthesizing the lithium bis (chlorosulfonyl) imide can only reach about 80%, and the production process is still complex and the yield is relatively low. In addition, in the fluorination process, hydrogen fluoride and fluorine gas which are extremely corrosive raw materials are generally adopted to react at high temperature and high pressure, so that the reaction process has high risk and high requirements on production equipment. The defects limit the further improvement of the overall production capacity of LiFSI in the industry.
The second synthesis route is to directly synthesize bis-fluorosulfonyl imide (HFSI) by using sulfuryl fluoride and ammonia gas as raw materials, and then synthesize LiFSI (for example, CN 111620315A) by two steps of lithiation. Although the process has high yield and few steps, the reaction control difficulty is high and safety accidents are easily caused by improper operation because two gases are involved in simultaneous reaction, and only a small part of enterprises adopt the production process at present.
Disclosure of Invention
The invention aims to solve part of defects in the production process of the prior bis-fluorosulfonyl imide and lithium salt thereof, and provides a safe and efficient method for producing the bis-fluorosulfonyl imide and the lithium salt thereof, and the method has the advantages of high yield and good purity.
In order to achieve the purpose, the invention adopts the technical scheme that:
the production method of the bis-fluorosulfonyl imide is characterized by comprising the following steps:
(1) Under the atmosphere of nitrogen, taking sulfuryl chloride fluoride with a structure shown as (I) as a raw material, and introducing ammonia gas in an aprotic solvent under the action of an organic basic catalyst to obtain bis (fluorosulfonyl) imide with a structure shown as (II);
a production method of lithium bis (fluorosulfonyl) imide is characterized by comprising the following steps:
(1) Under the nitrogen atmosphere, taking sulfuryl chloride fluoride with the structure shown as (I) as a raw material, introducing ammonia gas in an aprotic solvent under the action of an organic basic catalyst to obtain an alkaline reaction solution of bis (fluorosulfonyl) imide with the structure shown as (II), carrying out reduced pressure distillation to recover the solvent, washing the obtained reaction concentrated solution, and directly using the reaction concentrated solution for the next lithiation reaction without further purification;
(2) And (2) adding a solvent into the reaction liquid obtained in the step (1) for dissolving, adding a lithium salt in a nitrogen atmosphere, stirring for reaction, and purifying to obtain the lithium bis (fluorosulfonyl) imide shown in the structure (III).
The synthetic route of the invention is as follows:
the further setting is that:
in the step (1):
the aprotic solvent is: acetonitrile, acetone, esters such as dimethyl carbonate, diethyl carbonate, ethyl acetate and the like, ethers such as tetrahydrofuran, methyl tert-butyl ether, ethylene glycol dimethyl ether and the like, sulfones such as dimethyl sulfoxide, sulfolane and the like, preferably acetonitrile;
the organic basic catalyst is as follows: any one of trimethylamine, triethylamine, N-diisopropylethylamine, tripropylamine, tributylamine, pyridine, etc., preferably triethylamine;
the molar ratio of the sulfuryl chloride fluoride to the organic basic catalyst to the ammonia gas is 1-10, and is preferably 1;
the reaction temperature of the step (1) is-30 to 50 ℃, and preferably 0 to 5 ℃;
in the step (2):
the solvent is as follows: acetonitrile, acetone, esters such as dimethyl carbonate, diethyl carbonate, ethyl acetate, etc., ethers such as tetrahydrofuran, methyl tert-butyl ether, ethylene glycol dimethyl ether, etc., sulfones such as dimethyl sulfoxide, sulfolane, etc., halogenated alkanes such as dichloromethane, dichloroethane, etc.;
the lithium salt is: any one of lithium hydroxide, lithium carbonate, lithium acetate, lithium chloride, lithium fluoride, lithium oxalate and lithium phosphate;
the molar ratio of the lithium salt (in terms of lithium atoms) to sulfuryl fluoride is 1.5 to 3, preferably 1;
the reaction temperature of the step (2) is-30 to 50 ℃;
compared with the prior art, the invention has the following beneficial effects:
1. the invention provides a method for producing difluoride sulfimide and lithium salt thereof, which has the advantages of few reaction steps, high product yield and good purity.
2. The method avoids the step of high-temperature and high-pressure fluorination, does not use high-risk materials such as hydrogen fluoride, fluorine gas and the like, has high reaction safety and low requirements on operation and equipment, and is suitable for industrial production.
3. The raw materials are easy to obtain, and the main reaction raw material sulfuryl chloride fluoride can reach a liquid state through simple condition control, so that the simultaneous use of various gas raw materials is avoided, and the reaction control difficulty and the reaction risk are effectively reduced.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of protection of the invention is not limited thereto:
example 1:
controlling the temperature to 0 ℃ in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, pumping 91.1g of triethylamine, 120g of acetonitrile and 71.1g of sulfuryl chloride fluoride in sequence, stirring for 0.5h, controlling the temperature to 0 ℃, slowly introducing 5.1g of ammonia gas, and keeping the temperature for 12h after the gas introduction is finished, thereby finishing the reaction. The reaction solution is decompressed, distilled and recycled, the concentrated solution is washed by water to obtain 85g of organic phase, and the organic phase is directly used for the next lithiation reaction without further purification.
Transferring the reaction solution in the previous step into a 500ml four-neck flask, adding 100g of acetonitrile for dissolution, controlling the temperature to be 0 ℃ under the nitrogen atmosphere, adding 7.2g of lithium hydroxide in batches, preserving the temperature and stirring for 12 hours. And filtering the reaction solution, and distilling the filtrate under reduced pressure to obtain 50.5g of the product lithium bis (fluorosulfonyl) imide, wherein the yield is 90%.
Example 2:
controlling the temperature to-10 ℃ in a 500mL high-pressure reaction kettle under the atmosphere of nitrogen, pumping 151.8g of triethylamine and 118.5g of sulfuryl chloride fluoride in sequence, stirring for 0.5h, controlling the temperature to-10 ℃, slowly introducing 8.5g of ammonia gas, and keeping the temperature for 12h after the introduction of the ammonia gas is finished, thereby finishing the reaction. The reaction solution was washed with water to obtain 142g, which was used in the next lithiation reaction without further purification.
Transferring the reaction solution in the previous step into a 500ml four-neck flask, adding 200g of dimethyl carbonate for dissolution, controlling the temperature to be 0 ℃ under the nitrogen atmosphere, adding 12g of lithium hydroxide in batches, and stirring for 12 hours under the heat preservation condition. And filtering the reaction solution, and distilling the filtrate under reduced pressure to obtain 82.3g of the product lithium bis (fluorosulfonyl) imide with the yield of 88%.
Example 3:
controlling the temperature to-10 ℃ in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, pumping in 116.3g of N, N-diisopropylethylamine, 120g of acetonitrile and 71.1g of sulfuryl chlorofluoro, stirring for 0.5h, controlling the temperature to-10 ℃, slowly introducing 5.1g of ammonia gas, and keeping the temperature for 12h after the gas introduction is finished, thereby finishing the reaction. The reaction solution is decompressed, distilled and recycled to obtain the solvent, and the concentrated solution is washed by water to obtain 94g of organic phase which is directly used for the next lithiation reaction without further purification.
And transferring the reaction solution in the previous step into a 500ml four-neck flask, adding 100g of acetonitrile for dissolution, controlling the temperature to be 0 ℃ under the nitrogen atmosphere, adding 11.1g of lithium carbonate in batches, and stirring for 12 hours under heat preservation. The reaction solution was filtered, and the filtrate was subjected to distillation under reduced pressure to give 49.3g of lithium bis (fluorosulfonyl) imide, a yield of 88%.
Example 4:
controlling the temperature to-10 ℃ in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, pumping 71.2g of pyridine, 120g of tetrahydrofuran and 71.1g of sulfuryl chloride fluoride in sequence, stirring for 0.5h, controlling the temperature to-10 ℃, slowly introducing 5.1g of ammonia gas, controlling the temperature to-10 ℃, keeping the temperature for 12h after the gas introduction is finished, and finishing the reaction. The reaction solution is decompressed, distilled and recycled, and the concentrated solution is washed by water to obtain 79g of organic phase which is directly used for the next lithiation reaction without further purification.
Transferring the reaction solution in the previous step into a 500ml four-neck flask, adding 100g of tetrahydrofuran for dissolving, adding 12.7g of lithium chloride in batches at room temperature under the nitrogen atmosphere, and stirring for 12 hours under the heat preservation condition. And filtering the reaction solution, and distilling the filtrate under reduced pressure to obtain 46g of the product lithium bis (fluorosulfonyl) imide with the yield of 82%.
Example 5:
controlling the temperature to-20 ℃ in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, pumping 118.7g of pyridine and 118.5g of sulfuryl chloride fluoride in sequence, stirring for 0.5h, controlling the temperature to-20 ℃, slowly introducing 5.1g of ammonia gas, after the introduction of the ammonia gas is finished, slowly raising the temperature to the room temperature, and preserving the temperature for 12h to finish the reaction. The reaction solution is decompressed and distilled to recover the solvent, and the concentrated solution is washed by water to obtain 125g of organic phase which is directly used for the next lithiation reaction without further purification.
Transferring the reaction solution in the previous step into a 500ml four-neck flask, adding 250g of methyl tert-butyl ether for dissolving, adding 12.7g of lithium chloride in batches at room temperature under the nitrogen atmosphere, and stirring for 12 hours under the heat preservation condition. And filtering the reaction solution, and distilling the filtrate under reduced pressure to obtain 74.8g of the product lithium bis (fluorosulfonyl) imide with the yield of 80%.
Example 6:
controlling the temperature to-10 ℃ in a 500mL high-pressure reaction kettle under the atmosphere of nitrogen, pumping 147.8g of trimethylamine and 118.5g of sulfuryl chloride fluoride in sequence, stirring for 0.5h, controlling the temperature to-10 ℃, slowly introducing 5.1g of ammonia gas, and after the introduction of the ammonia gas is finished, keeping the temperature for 12h to finish the reaction. The reaction solution is decompressed and distilled to recover the solvent, and the concentrated solution is washed by water to obtain 120g of organic phase which is directly used for the next lithiation reaction without further purification.
And transferring the reaction solution in the previous step into a 500ml four-neck flask, adding 100g of ethyl acetate to dissolve, adding 11.1g of lithium carbonate in batches at room temperature under a nitrogen atmosphere, and stirring for 12 hours under heat preservation. And filtering the reaction solution, and distilling the filtrate under reduced pressure to obtain 47.7g of the product lithium bis (fluorosulfonyl) imide with the yield of 85%.
Example 7:
controlling the temperature to 0 ℃ in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, pumping 88.7g of trimethylamine, 120g of acetonitrile and 71.1g of sulfuryl chloride fluoride in sequence, stirring for 0.5h, controlling the temperature to 0 ℃, slowly introducing 5.1g of ammonia gas, slowly raising the temperature to room temperature after the gas introduction is finished, and preserving the temperature for 12h to finish the reaction. The reaction solution was distilled under reduced pressure to recover the solvent, and the concentrated solution was washed with water to obtain 73g of an organic phase, which was used in the next lithiation reaction without further purification.
Transferring the reaction solution in the previous step into a 500ml four-neck flask, adding 100g of acetonitrile for dissolution, controlling the temperature to be 0 ℃ under the nitrogen atmosphere, adding 7.2g of lithium hydroxide in batches, preserving the temperature and stirring for 12 hours. The reaction solution was filtered, and 47.1g of lithium bis (fluorosulfonyl) imide was obtained from the filtrate by distillation under reduced pressure, with a yield of 84%.
Summary analysis:
reference examples 1, 3 and 7 show: by adjusting the type of the organic basic catalyst in the first step of reaction, the contrast effect shows that the type of the organic basic catalyst has a large influence on the reaction.
Referring to examples 4 and 5: the heat preservation temperature of the first step reaction and the solvent type of the second step reaction are adjusted, and comparison shows that the heat preservation temperature of the first step reaction is high, and the yield of the first step reaction is reduced; the solvent of the second step reaction has certain influence on the reaction, and the reaction yield can be effectively improved by selecting a proper solvent.
Referring to examples 1, 2, 6 and 7: the solvent and reaction temperature for the first reaction step and the choice of the solvent for the second reaction step have a great influence. When the reaction temperature in the first step is not more than 0 ℃, the difference of the reaction results is not large, and is more than 0 ℃, so that the reaction is adversely affected; the solvent of the second step reaction has certain influence on the reaction, and the selection of proper solvent is favorable for improving the reaction yield.
The best embodiment is as follows: example 1.
Claims (15)
1. The production method of the bis (fluorosulfonyl) imide is characterized by comprising the following steps:
(1) Under the atmosphere of nitrogen, taking sulfuryl chloride fluoride shown in a structural formula (I) as a raw material, and introducing ammonia gas in an aprotic solvent under the action of an organic basic catalyst to obtain bis (fluorosulfonyl) imide shown in a structural formula (II);
2. the production method of the lithium bis (fluorosulfonyl) imide salt is characterized by comprising the following steps of:
(1) Under the atmosphere of nitrogen, taking sulfuryl chloride fluoride shown in a structural formula (I) as a raw material, introducing ammonia gas in an aprotic solvent under the action of an organic alkaline catalyst to obtain an alkaline reaction liquid of bis (fluorosulfonyl) imide shown in a structural formula (II), distilling under reduced pressure to recover the solvent, washing the obtained reaction concentrated liquid, and directly using the reaction concentrated liquid for the next lithiation reaction without further purification;
(2) Adding a solvent into the alkali reaction liquid of the bis (fluorosulfonyl) imide obtained in the step (1) for dissolving, adding a lithium salt in a nitrogen atmosphere, stirring for reaction, and purifying to obtain the bis (fluorosulfonyl) imide lithium shown in the structural formula (III);
3. the method for producing a lithium salt of bis (fluorosulfonyl) imide according to claim 1 or 2, wherein: in the step (1): the aprotic solvent is selected from any one of: acetonitrile, acetone, esters selected from dimethyl carbonate, diethyl carbonate or ethyl acetate, ethers selected from tetrahydrofuran, methyl tert-butyl ether or ethylene glycol dimethyl ether, and sulfones selected from dimethyl sulfoxide or sulfolane.
4. The method for producing a lithium salt of bis (fluorosulfonyl) imide according to claim 3, wherein: in the step (1): the aprotic solvent is acetonitrile.
5. The method for producing a lithium salt of bis (fluorosulfonyl) imide according to claim 1 or 2, wherein: the organic basic catalyst is as follows: trimethylamine, triethylamine, N-diisopropylethylamine, tripropylamine, tributylamine and pyridine.
6. The method for producing a lithium salt of bis (fluorosulfonyl) imide according to claim 5, wherein: the organic basic catalyst is triethylamine.
7. The method for producing a lithium bis (fluorosulfonyl) imide salt according to claim 1 or 2, wherein: the molar ratio of the sulfuryl chloride fluoride to the organic alkaline catalyst to the ammonia gas is 1-10.
8. The method for producing lithium bis (fluorosulfonyl) imide according to claim 7, wherein: the molar ratio of the sulfuryl chloride fluoride to the organic alkaline catalyst to the ammonia gas is 1.5.
9. The method for producing a lithium bis (fluorosulfonyl) imide salt according to claim 1 or 2, wherein: the reaction temperature of the step (1) is-30 to 50 ℃.
10. The method for producing lithium bis (fluorosulfonyl) imide salt according to claim 9, wherein: the reaction temperature in the step (1) is 0-5 ℃.
11. The method for producing lithium bis (fluorosulfonyl) imide according to claim 2, wherein: in the step (2): the solvent is selected from any one of the following: acetonitrile, acetone, esters selected from dimethyl carbonate, diethyl carbonate or ethyl acetate, ethers selected from tetrahydrofuran, methyl tert-butyl ether or ethylene glycol dimethyl ether, sulfones selected from dimethyl sulfoxide or sulfolane, and halogenated alkanes selected from dichloromethane or dichloroethane.
12. The method for producing lithium bis (fluorosulfonyl) imide according to claim 2, wherein: the lithium salt is: any one of lithium hydroxide, lithium carbonate, lithium acetate, lithium chloride, lithium fluoride, lithium oxalate and lithium phosphate.
13. The method for producing lithium bis (fluorosulfonyl) imide according to claim 2, wherein: the molar ratio of the lithium salt to the sulfuryl fluoride is 1.5-3.
14. The method for producing a lithium salt of bis (fluorosulfonyl) imide according to claim 13, wherein: the molar ratio of the lithium salt to the sulfuryl fluoride is 1.
15. The method for producing lithium bis (fluorosulfonyl) imide according to claim 2, wherein: the reaction temperature in the step (2) is-30 to 50 ℃.
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