CN115259112B - Difluorosulfonyl imide and method for producing lithium salt thereof - Google Patents
Difluorosulfonyl imide and method for producing lithium salt thereof Download PDFInfo
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Abstract
The invention discloses a production method of difluoro-sulfonyl imide and lithium salt thereof, belonging to the technical field of difluoro-sulfonyl imide and lithium salt thereof, comprising the following steps: (1) Under the nitrogen atmosphere, sulfuryl chloride fluoride is taken as a raw material, ammonia gas is introduced into the aprotic solvent under the action of an organic alkaline catalyst to obtain an alkaline reaction solution of difluoro sulfimide, the solvent is recovered by reduced pressure distillation, and the obtained reaction concentrated solution is directly used for the next lithiation reaction without further purification after being washed with water; (2) Adding a solvent into the reaction solution obtained in the step (1) for dissolution, adding lithium salt under the nitrogen atmosphere, stirring for reaction, and obtaining lithium difluorosulfimide after purification operation; the invention has the advantages of high yield, good purity, safety and high efficiency.
Description
Technical Field
The invention relates to a method for producing difluoro sulfimide and lithium salt thereof.
Background
In recent years, with the national support of new energy automobile industry, the new energy automobile market is rapidly developed, and the lithium ion power battery industry is rapidly advancing on a high-quality development road. Currently, liPF takes into consideration factors such as battery cost, safety performance and the like 6 Lithium hexafluorophosphate is the lithium salt of lithium battery solute most widely used commercially, but during use, liPF 6 The problems of poor thermal stability, easiness in hydrolysis and the like exist, so that the capacity of the battery is quickly attenuated, and potential safety hazards are brought. For many years, the lithium battery industry has remained onNew materials are sought to optimize electrolyte performance. Under the environment, the novel electrolyte solute LiFeSI (lithium bis (fluorosulfonyl imide)) with the advantages of better thermal stability, hydrolysis resistance and the like is the novel lithium salt with the best industrialization prospect at present, and becomes the core competitiveness of lithium battery enterprises in the high nickel age.
Early, liSSI in the laboratory was synthesized by a multi-step reaction starting from sulfamic acid and phosphorus pentachloride (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 and the production cost is high, and the commercialized use of the process is restricted. In recent years, along with the breakthrough of LiFSI production technology and the reduction of cost, liFSI has the conditions of industrial production and large-scale commercial application.
Currently, liFSI is distinguished by a synthesis process using a synthetic route applied to production, mainly by two:
the first synthesis route is based on the optimization of the traditional synthesis process, by changing the selection of raw materials, chlorosulfonic acid and sulfamic acid or chlorosulfonyl isocyanate are used as raw materials to synthesize dichloro-sulfonyl imide (HClSI), then difluoro-sulfonyl imide (HFSI) is synthesized by fluorine, and finally LiFSI (for example, CN105731399B, CN 106044728B) is obtained by three-step reaction through lithiation. Compared with the traditional process, the optimized process reduces the reaction steps and the types of reaction products, remarkably reduces the production difficulty and the production cost compared with the traditional process, and most enterprises at present, such as polyfluorodon and the like, use the process to produce LiFSI. However, the above production process still requires three steps to synthesize lithium bis (fluorosulfonyl) imide, and the single step yield of the first step of synthesizing bis (chlorosulfonyl) imide is generally only about 80%, and the production process is still complex and the yield is relatively low. In addition, the process is usually carried out by adopting hydrogen fluoride, fluorine gas and other raw materials with extremely strong corrosiveness to react at high temperature and high pressure, so that the reaction process has high risk and high production equipment requirement. The above drawbacks limit further improvement of the overall capacity of LiFSI in the industry.
The second synthesis route is to directly synthesize difluoro-sulfonyl-imide (HFSI) from sulfuryl fluoride and ammonia gas, and then to synthesize LiFSI (e.g. CN 111620315A) by lithiation in two steps. Although the process has high yield and few steps, the two gases are involved in the simultaneous reaction, the reaction control difficulty is high, the safety accident is easily caused by improper operation, and only a small part of enterprises currently adopt the production process.
Disclosure of Invention
The invention aims to solve part of defects in the current production process of the difluoro sulfonyl imide and the lithium salt thereof, and provides a safe and efficient production method of the difluoro sulfonyl imide and the lithium salt thereof, which has high yield and good purity.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a method for producing bis-fluorosulfonyl imide, comprising the steps of:
(1) Introducing ammonia gas in an aprotic solvent under the action of an organic alkaline catalyst by taking sulfuryl chloride fluoride with a structure shown as (I) as a raw material in a nitrogen atmosphere to obtain difluoro sulfimide with a structure shown as (II);
the production method of the lithium bis (fluorosulfonyl) imide salt is characterized by comprising the following steps:
(1) In nitrogen atmosphere, sulfuryl chloride fluoride with the structure shown in (I) is taken as a raw material, ammonia gas is introduced into the raw material under the action of an organic alkaline catalyst in an aprotic solvent to obtain an alkaline reaction solution of difluoro sulfimide with the structure shown in (II), the solvent is recovered by reduced pressure distillation, and the obtained reaction concentrated solution is directly used for the next lithiation reaction without further purification after water washing;
(2) And (3) adding a solvent into the reaction solution obtained in the step (1) for dissolution, adding lithium salt under the 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 arrangement is that:
in step (1):
the aprotic solvent is: 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., preferably acetonitrile;
the organic alkaline catalyst is as follows: any one of trimethylamine, triethylamine, N-diisopropylethylamine, tripropylamine, tributylamine, pyridine and the like, preferably triethylamine;
the molar ratio of the sulfuryl chloride fluoride, the organic alkaline catalyst and the ammonia gas is 1:1-10:0.4-1, preferably 1:1.5:0.5;
the reaction temperature in the step (1) is-30-50 ℃, preferably 0-5 ℃;
in the step (2):
the solvent is as follows: any one of 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 methylene chloride, dichloroethane, etc.;
the lithium salt is as follows: 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 (calculated by lithium atoms) to the sulfuryl fluoride is 1:1.5-3, preferably 1:2;
the reaction temperature of the step (2) is-30-50 ℃;
compared with the prior art, the invention has the beneficial effects that:
1. the invention provides a production method of difluoro sulfimide and lithium salt thereof, which has the advantages of few reaction steps, high product yield and good purity.
2. The invention avoids the high-temperature high-pressure fluorination step, does not use high-risk materials such as hydrogen fluoride, fluorine gas and the like, has high reaction safety, and is suitable for industrial production, and the operation and equipment requirements are not harsh.
3. The raw materials are easy to obtain, the main reaction raw material sulfuryl chloride fluoride can reach a liquid state through simple condition control, 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 the following specific examples, but the scope of the invention is not limited thereto:
example 1:
in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, controlling the temperature to 0 ℃, sequentially pumping 91.1g of triethylamine, 120g of acetonitrile and 71.1g of sulfuryl chloride fluoride, stirring for 0.5h, slowly introducing 5.1g of ammonia gas at the temperature of 0 ℃, and continuously preserving the temperature for 12h after the ventilation is finished to finish the reaction. The solvent was recovered by distillation under reduced pressure, and the concentrated solution was washed with water to give 85g of an organic phase, which was directly used for the next lithiation reaction without further purification.
The reaction solution in the last step is transferred into a 500ml four-neck flask, 100g of acetonitrile is added for dissolution, 7.2g of lithium hydroxide is added in batches under the nitrogen atmosphere and the temperature is controlled to be 0 ℃, and the mixture is stirred for 12 hours under the heat preservation. The reaction solution was filtered, and the filtrate was distilled under reduced pressure to obtain 50.5g of lithium difluorosulfimide with a yield of 90%.
Example 2:
in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, controlling the temperature to minus 10 ℃, sequentially pumping 151.8g of triethylamine, 118.5g of sulfuryl chloride fluoride, stirring for 0.5h, slowly introducing 8.5g of ammonia gas at minus 10 ℃, and continuously preserving the temperature for 12h after the ventilation is finished to finish the reaction. The reaction solution was washed with water to obtain 142g, which was used directly in the next lithiation reaction without further purification.
Transferring the reaction solution in the last 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 at a constant temperature. The reaction solution was filtered, and the filtrate was distilled under reduced pressure to obtain 82.3g of lithium difluorosulfimide in 88% yield.
Example 3:
in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, controlling the temperature to minus 10 ℃, pumping 116.3g of N, N-diisopropylethylamine, 120g of acetonitrile, 71.1g of sulfuryl chloride fluoride, stirring for 0.5h, slowly introducing 5.1g of ammonia gas at the temperature of minus 10 ℃, and continuing to keep the temperature for 12h after the ventilation is finished to finish the reaction. The solvent was recovered by distillation under reduced pressure, and the concentrate was washed with water to give 94g of an organic phase, which was used directly in the next lithiation reaction without further purification.
The reaction solution in the last step is transferred into a 500ml four-neck flask, 100g of acetonitrile is added for dissolution, 11.1g of lithium carbonate is added in batches under the nitrogen atmosphere and the temperature is controlled to be 0 ℃, and the mixture is stirred for 12 hours under the heat preservation. The reaction solution was filtered, and the filtrate was distilled under reduced pressure to obtain 49.3g of lithium difluorosulfimide in 88% yield.
Example 4:
in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, controlling the temperature to minus 10 ℃, pumping 71.2g of pyridine, 120g of tetrahydrofuran and 71.1g of sulfuryl chloride fluoride in sequence, stirring for 0.5h, slowly introducing 5.1g of ammonia at minus 10 ℃ and controlling the temperature to minus 10 ℃, and continuously preserving the heat for 12h after the ventilation is finished to finish the reaction. The solvent was recovered by distillation under reduced pressure, and the concentrated solution was washed with water to give 79g of an organic phase, which was used directly for the next lithiation reaction without further purification.
The reaction solution in the last step is transferred into a 500ml four-neck flask, 100g of tetrahydrofuran is added for dissolution, 12.7g of lithium chloride is added in batches under the nitrogen atmosphere at room temperature, and the temperature is kept and the stirring is carried out for 12h. The reaction solution is filtered, and the filtrate is distilled under reduced pressure to obtain 46g of the product lithium bis (fluorosulfonyl) imide with the yield of 82%.
Example 5:
in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, controlling the temperature to minus 20 ℃, sequentially pumping 118.7g of pyridine, 118.5g of sulfuryl chloride fluoride, stirring for 0.5h, slowly introducing 5.1g of ammonia gas at the temperature of minus 20 ℃, slowly heating to room temperature after the ventilation is finished, and preserving heat for 12h to finish the reaction. The solvent was recovered by distillation under reduced pressure, and the concentrate was washed with water to give 125g of an organic phase, which was used directly for the next lithiation reaction without further purification.
The reaction solution in the previous step is transferred into a 500ml four-necked flask, 250g of methyl tertiary butyl ether is added for dissolution, 12.7g of lithium chloride is added in batches under the nitrogen atmosphere at room temperature, and the temperature is kept and the stirring is carried out for 12 hours. The reaction solution was filtered, and the filtrate was distilled under reduced pressure to obtain 74.8g of lithium difluorosulfimide with a yield of 80%.
Example 6:
in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, controlling the temperature to minus 10 ℃, sequentially pumping 147.8g of trimethylamine and 118.5g of sulfuryl chloride fluoride, stirring for 0.5h, slowly introducing 5.1g of ammonia gas at the temperature of minus 10 ℃, and continuing to keep the temperature for 12h after the ventilation is finished to finish the reaction. The solvent was recovered by distillation under reduced pressure, and the concentrated solution was washed with water to give 120g of an organic phase, which was used directly for the next lithiation reaction without further purification.
The reaction solution in the previous step is transferred into a 500ml four-necked flask, 100g of ethyl acetate is added for dissolution, 11.1g of lithium carbonate is added in batches under the nitrogen atmosphere at room temperature, and the temperature is kept and the stirring is carried out for 12h. The reaction solution was filtered, and the filtrate was distilled under reduced pressure to obtain 47.7g of lithium difluorosulfimide with a yield of 85%.
Example 7:
in a 500mL high-pressure reaction kettle under the nitrogen atmosphere, 88.7g of trimethylamine, 120g of acetonitrile and 71.1g of sulfuryl chloride fluoride are pumped in sequence under the temperature controlled to 0 ℃, the mixture is stirred for 0.5h, 5.1g of ammonia gas is slowly introduced under the temperature controlled to 0 ℃, after the ventilation is finished, the mixture is slowly heated to room temperature, and the reaction is completed after the heat preservation is carried out for 12h. The solvent was recovered by distillation under reduced pressure, and the concentrate was washed with water to give 73g of an organic phase, which was used directly in the next lithiation reaction without further purification.
The reaction solution in the last step is transferred into a 500ml four-neck flask, 100g of acetonitrile is added for dissolution, 7.2g of lithium hydroxide is added in batches under the nitrogen atmosphere and the temperature is controlled to be 0 ℃, and the mixture is stirred for 12 hours under the heat preservation. The reaction solution was filtered, and the filtrate was distilled under reduced pressure to obtain 47.1g of lithium difluorosulfimide, with a yield of 84%.
Summary analysis:
reference is made to examples 1, 3 and 7: by adjusting the types of the organic alkaline catalysts in the first step of reaction, the comparison effect can find that the types of the organic alkaline catalysts have larger influence on the reaction.
Reference is made 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 has certain influence on the reaction, and the reaction yield can be effectively improved by selecting a proper solvent.
Reference is made to examples 1, 2, 6 and 7: the solvent of the first reaction, the reaction temperature, and the choice of the solvent of the second reaction have a great influence. Wherein, when the reaction temperature of the first step is not more than 0 ℃, the difference of reaction results is not large and is more than 0 ℃, which has adverse effect on the reaction; the solvent of the second step has a certain influence on the reaction, and the selection of a proper solvent is favorable for improving the reaction yield.
The preferred embodiments are: example 1.
Claims (10)
1. The production method of the lithium bis (fluorosulfonyl) imide salt is characterized by comprising the following steps:
(1) In nitrogen atmosphere, sulfuryl chloride fluoride shown in a structural formula (I) is taken as a raw material, ammonia gas is introduced under the action of an organic alkaline catalyst in an aprotic solvent to obtain an alkaline reaction solution of difluoro sulfimide shown in a structural formula (II), the solvent is recovered by reduced pressure distillation, and the obtained reaction concentrated solution is directly used for the next lithiation reaction without further purification after water washing;
the molar ratio of the sulfuryl chloride fluoride to the organic alkaline catalyst to the ammonia gas is 1:1.5:0.5;
the reaction temperature of the step (1) is 0-5 ℃;
(2) Dissolving the difluoro sulfonimide alkaline reaction liquid obtained in the step (1) in a solvent, adding lithium salt in a nitrogen atmosphere, stirring for reaction, and purifying to obtain the difluoro sulfonimide lithium shown in the structural formula (III);
2. the method for producing a lithium difluorosulfimide salt according to claim 1, characterized in that: in step (1): the aprotic solvent is selected from any one of the following: acetonitrile, acetone, dimethyl carbonate, diethyl carbonate, ethyl acetate, tetrahydrofuran, methyl tert-butyl ether, ethylene glycol dimethyl ether, dimethyl sulfoxide or sulfolane.
3. The method for producing a lithium difluorosulfimide salt according to claim 2, characterized in that: in step (1): the aprotic solvent is acetonitrile.
4. The method for producing a lithium difluorosulfimide salt according to claim 1, characterized in that: the organic alkaline catalyst is as follows: trimethylamine, triethylamine, N-diisopropylethylamine, tripropylamine, tributylamine, pyridine.
5. The method for producing a lithium difluorosulfimide salt according to claim 4, wherein: the organic basic catalyst is triethylamine.
6. The method for producing a lithium difluorosulfimide salt according to claim 1, characterized in that: in the step (2): the solvent is selected from any one of the following: acetonitrile, acetone, dimethyl carbonate, diethyl carbonate, ethyl acetate, tetrahydrofuran, methyl tert-butyl ether, ethylene glycol dimethyl ether, dimethyl sulfoxide, sulfolane, methylene chloride or dichloroethane.
7. The method for producing a lithium difluorosulfimide salt according to claim 1, characterized in that: the lithium salt is as follows: any one of lithium hydroxide, lithium carbonate, lithium acetate, lithium chloride, lithium fluoride, lithium oxalate, and lithium phosphate.
8. The method for producing a lithium difluorosulfimide salt according to claim 1, characterized in that: the molar ratio of the lithium salt to the sulfuryl fluoride is 1:1.5-3.
9. The method for producing a lithium difluorosulfimide salt according to claim 8, wherein: the molar ratio of the lithium salt to the sulfuryl fluoride is 1:2.
10. The method for producing a lithium difluorosulfimide salt according to claim 1, characterized in that: the reaction temperature of the step (2) is-30-50 ℃.
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