CN108975292A - A kind of preparation method of double fluorine sulfonyl imide compounds - Google Patents
A kind of preparation method of double fluorine sulfonyl imide compounds Download PDFInfo
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- CN108975292A CN108975292A CN201811078921.4A CN201811078921A CN108975292A CN 108975292 A CN108975292 A CN 108975292A CN 201811078921 A CN201811078921 A CN 201811078921A CN 108975292 A CN108975292 A CN 108975292A
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/086—Compounds containing nitrogen and non-metals and optionally metals containing one or more sulfur atoms
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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Abstract
The invention discloses a kind of preparation method of double fluorine sulfonyl imide compounds, the preparation method the following steps are included: (1) by FSO2X, nitrogen source, acid binding agent and aprotic solvent are mixed to get mixture；(2) heating makes mixture back flow reaction, sustained response 12h~72h；(3) cooling after back flow reaction, pressure release is spin-dried for solvent, water washing is added to filter, and obtains crude product；(4) crude product is recrystallized, obtains the finished product of double fluorine sulfonyl imide compounds.A kind of raw material that the preparation method of double fluorine sulfonyl imide compounds needs of the present invention is easy to get, and step is simple, no danger, pollution-free；Yield is high, easily separated purification；It is not harsh to operate equipment requirement, is suitble to industrialized production.
Description
Technical field
The present invention relates to double fluorine sulfimide class preparation fields, especially a kind of preparation of double fluorine sulfonyl imide compounds
Method.
Background technique
It is excellent that lithium secondary battery has high storage energy density, long service life, environmentally protective, high/low temperature is adaptable etc.
Point is widely used in the fields such as electronic product, electric car, aerospace, energy storage.However, extensive with lithium secondary battery
Using to its cycle performance, energy density, high/low temperature conformability, more stringent requirements are proposed for high rate performance.
Electrolysis additive is the important component of lithium secondary battery, and excellent electrolysis additive is in lithium secondary battery
It is middle that positive electrochemical action occurs, the kinetic characteristics of battery can be improved, to be obviously improved the comprehensive performance of battery.
Such as application No. is 201611174656.0, entitled " a kind of nonaqueous electrolytic solution and the secondary electricity of lithium using the electrolyte
Pond ", it discloses a kind of nonaqueous electrolytic solution, including non-aqueous organic solvent, lithium salts and additive, additive includes pyridine boronic acid frequency
Which alkoxide compound and phenyl boric acid pinacol ester type compound.Such compound is applied to lithium secondary cell electrolyte, hence it is evident that
Improve the circulation, multiplying power and high/low temperature properties of lithium secondary battery.Application No. is 201610208000.X, entitled
" a kind of electrolyte and the lithium secondary battery including the electrolyte ", it discloses a kind of nonaqueous electrolytic solution, including it is non-aqueous organic
Solvent, lithium salts and additive, additive include two nitrile compounds of silicon oxygen and cathode film formation additive compound.Such compound
It applied to lithium secondary cell electrolyte, can be oxidized to avoid electrolyte composition, can also effectively remove and be produced in electrolyte generation
Raw Bronsted acid and lewis acid promotes the stability that lithium secondary battery recycles under high-temperature and high-pressure conditions.
However, pyridine boronic acid pinacol ester type compound and phenyl boric acid pinacol esters compound synthesis are difficult, purifying at
This height does not utilize extensive use.The passivation membrane impedance that nitrile electrolysis additive is formed is larger, is unfavorable for the multiplying power of battery and low
Temperature electric discharge.Therefore a kind of development technology is simple, the preparation method of non-environmental-pollution, product easy purification has great importance.
Summary of the invention
The defects of in view of the prior art, a kind of preparation method of double fluorine sulfonyl imide compounds is provided.
The present invention is realized by following proposal:
A kind of preparation method of double fluorine sulfonyl imide compounds, the preparation method the following steps are included:
(1) by FSO2X, nitrogen source, acid binding agent and aprotic solvent are mixed to get mixture；Wherein, nitrogen source is primary amine, ties up acid
Agent is non-proton organic amine；Acid binding agent and FSO2The molar ratio of X is 1:2~5；Nitrogen source and the molar ratio of acid binding agent be 1:3~
8；The X is F or CnF2n+1, n=1-5；
(2) heating makes mixture back flow reaction, sustained response 12h~72h；
(3) cooling after back flow reaction, pressure release is spin-dried for solvent, water washing is added to filter, and obtains crude product；
(4) crude product is recrystallized, obtains the finished product of double fluorine sulfonyl imide compounds.
The acid binding agent is at least one of triethylamine, tetramethylethylenediamine, tetramethyl -1,3- propane diamine.
The aprotic solvent is acetone, methylene chloride, acetonitrile, dimethyl sulfoxide, N,N-dimethylformamide, carbonic acid second
Enester, butylene, tetrahydrofuran, methyl formate, methyl acetate, methyl propionate, dimethyl carbonate, methyl ethyl carbonate, carbon
Diethyl phthalate, sulfolane, ethyl acetate or butyl acetate.
The nitrogen source is aniline, meta-aminotoluene, phenyl ethylamine, 4- hexamethylene aniline, cyclohexylamine, 4- phenylbenzylamine, 2- amino connection
Benzene, 2-aminopyridine, 2- amino -3- picoline, 2-AMINO-4-PICOLINE, 2- amino -6- picoline, 2- amino pyrrole
It coughs up, (S) -1-Cbz-3- amino-pyrrolidine, 4- pyrrolidines butylamine, (R) -1-BOC-3- aminomethyl pyrrolidine, N- ethyl -2- ammonia first
Base pyrrolidines, (S) -2- (aminomethyl) pyrrolidines, 1- amino piperidine, 4- amino -1- methyl piperidine, 4- amino -1- benzyl piepridine,
(S) -1- benzyl -3- amino piperidine, (R) -3- amino -1-BOC- piperidines, in (S) -1- tertbutyloxycarbonyl -3- amino piperidine
It is a kind of or several.
The back flow reaction carries out at a temperature of -50 DEG C~100 DEG C, and reflux time is 18h~36h.
The solvent of the recrystallization is ethyl alcohol, methanol, acetonitrile, ethyl acetate, 1,4- dioxane, toluene, one in benzene
Kind is several.
The molecular formula of double fluorine sulfonyl imide compounds finished products is RN (XSO2)2。
The invention has the benefit that
A kind of raw material that the preparation method of double fluorine sulfonyl imide compounds needs of the present invention is easy to get, and step is simple, no danger
Danger, it is pollution-free；Yield is high, easily separated purification；It is not harsh to operate equipment requirement, is suitble to industrialized production.
Specific embodiment
The preferred embodiment of the invention is further illustrated below:
A kind of preparation method of double fluorine sulfonyl imide compounds, the preparation method the following steps are included:
(1) by FSO2X, nitrogen source, acid binding agent and aprotic solvent are mixed to get mixture；Wherein, nitrogen source is primary amine, ties up acid
Agent is non-proton organic amine；Acid binding agent and FSO2The molar ratio of X is 1:2~5；Nitrogen source and the molar ratio of acid binding agent be 1:3~
8；The X is F or CnF2n+1, n=1-5；
(2) heating makes mixture back flow reaction, sustained response 12h~72h；
(3) cooling after back flow reaction, pressure release is spin-dried for solvent, water washing is added to filter, and obtains crude product；
(4) crude product is recrystallized, obtains the finished product of double fluorine sulfonyl imide compounds.
The acid binding agent is at least one of triethylamine, tetramethylethylenediamine, tetramethyl -1,3- propane diamine.
The aprotic solvent is acetone, methylene chloride, acetonitrile, dimethyl sulfoxide, N, N-dimethylformamide, carbonic acid second
Enester, butylene, tetrahydrofuran, methyl formate, methyl acetate, methyl propionate, dimethyl carbonate, methyl ethyl carbonate, carbon
Diethyl phthalate, sulfolane, ethyl acetate or butyl acetate.
The nitrogen source is aniline, meta-aminotoluene, phenyl ethylamine, 4- hexamethylene aniline, cyclohexylamine, 4- phenylbenzylamine, 2- amino connection
Benzene, 2-aminopyridine, 2- amino -3- picoline, 2-AMINO-4-PICOLINE, 2- amino -6- picoline, 2- amino pyrrole
It coughs up, (S) -1-Cbz-3- amino-pyrrolidine, 4- pyrrolidines butylamine, (R) -1-BOC-3- aminomethyl pyrrolidine, N- ethyl -2- ammonia first
Base pyrrolidines, (S) -2- (aminomethyl) pyrrolidines, 1- amino piperidine, 4- amino -1- methyl piperidine, 4- amino -1- benzyl piepridine,
(S) -1- benzyl -3- amino piperidine, (R) -3- amino -1-BOC- piperidines, in (S) -1- tertbutyloxycarbonyl -3- amino piperidine
It is a kind of or several.
The back flow reaction carries out at a temperature of -50 DEG C~100 DEG C, and reflux time is 18h~36h.
The solvent of the recrystallization is ethyl alcohol, methanol, acetonitrile, ethyl acetate, 1,4- dioxane, toluene, one in benzene
Kind is several.
The molecular formula of double fluorine sulfonyl imide compounds finished products is RN (XSO2)2。
The present invention provides a kind of reaction raw materials and synthetic route unlike the prior art to prepare electrolysis additive pair
The method of fluorine sulfonyl imide compounds.The raw material that the present invention uses is easy to get, non-environmental-pollution；Reaction product yield is high,
Easily separated purification, purity is high；Reaction step is simple, and operation and equipment requirement condition be not harsh, is suitble to industrialized production, with aobvious
The market application value of work；The double fluorine sulfonyl imide compounds of electrolysis additive of method preparation provided by the invention can be used for
Lithium secondary battery can significantly improve normal temperature circulation, high temperature circulation, multiplying power and the cryogenic property of lithium secondary battery.
The application is further elaborated below with reference to comparative example and embodiment.
Comparative example
Solvent ethylene carbonate/methyl ethyl carbonate/acetic acid propylene 1:2:1 in mass ratio is mixed, by electrolyte gross mass
Calculate in intermixture addition 1% vinylene carbonate, 12% lithium hexafluoro phosphate and 1% double fluorine sulfimide lithiums, obtain
Electrolyte: by the injection of gained electrolyte comprising the secondary electricity of lithium is made in the non-fluid injection battery core of anode pole piece, diaphragm and cathode pole piece
Pond obtains the battery of the present embodiment.
Embodiment 1
(1) 200g acetonitrile and 150.2g triethylamine are added into 1L autoclave, 45.9g aniline is added, while stirring
It is slowly added to 100g vikane (F2SO2) it is mixed to get mixture；Aniline, F2SO2Molar ratio with triethylamine is 1:2:3；It will be high
Reaction kettle heating is pressed, is warming up to 80 DEG C, is persistently stirred at reflux reaction 36h；It then is cooled to room temperature, washs, filtrate is obtained by extraction；
The solvent in filtrate is steamed into removing with Rotary Evaporators, obtains crude product, crude product is put into heating, vacuum drying in baking oven,
Obtain final product, weight 110g, yield 87%.
(2) final product can be purified further, obtain double fluorine sulfonyl imide compounds that purity is greater than 99%, tool
Steps are as follows for body: with 220g methanol by final product stirring and dissolving described in 110g, -24 DEG C stand filtering for 24 hours, obtain solid precipitating
It is put into vacuum drying in baking oven, obtains the double fluorine sulfimides of N- phenyl after purification, purity reaches 99% or more.
(3) the double fluorine sulfimides of the 0.5g N- phenyl of above method preparation are added in the electrolyte in comparative example, are made
At lithium secondary battery, the battery of embodiment 1 is obtained.
It is applied in lithium battery by the lithium battery electrolytes that method in embodiment 1 is prepared, by testing lithium battery
It is as shown in table 1 to obtain parameter.
Embodiment 2
(1) 300g methylene chloride and 145.2g tetramethylethylenediamine are added into 1L autoclave, 40g 2- ammonia is added
Yl pyridines are slowly added to 85g sulfuryl fluoride (F while stirring2SO2) it is mixed to get mixture；2-aminopyridine, F2SO2With tetramethyl
The molar ratio of ethylenediamine is 1:2:3；Autoclave is heated, is warming up to 40 DEG C, is persistently stirred at reflux reaction 36h；Then cold
But it to room temperature, washs, filtrate is obtained by extraction；The solvent in filtrate is steamed into removing with Rotary Evaporators, obtains crude product, it will be thick
Product is put into heating, vacuum drying in baking oven, obtains final product, weight 96g, yield 89%.
(2) final product can be purified further, obtain double fluorine sulfonyl imide compounds that purity is greater than 99%, tool
Steps are as follows for body: the final product stirring and dissolving described in 192g methanol 96g, -24 DEG C of standing 36h, filtering, obtains solid precipitating and is put into
Vacuum drying in baking oven, obtains double fluorine sulfonyl imide compounds after purification, and purity reaches 99% or more.
(3) the double fluorine sulfimides of the 7g N- pyridyl group of above method preparation are added in the electrolyte in comparative example, are made
At lithium secondary battery, the battery of the present embodiment is obtained.
It is applied in lithium battery by the lithium battery electrolytes that method in embodiment 2 is prepared, by testing lithium battery
It is as shown in table 1 to obtain parameter.
Embodiment 3
(1) 230g acetone and 191.3g tetramethyl-1,3-propane diamine are added into 1L autoclave, 40.2g2- is added
Amino-pyrroles are slowly added to 100g vikane (F while stirring2SO2) it is mixed to get mixture；Aniline, F2SO2With tetramethyl second
The molar ratio of diamines is 1:2:3；Autoclave is heated, is warming up to 60 DEG C, is persistently stirred at reflux reaction 36h；Then it cools down
To room temperature, washs, filtrate is obtained by extraction；The solvent in filtrate is steamed into removing with Rotary Evaporators, crude product is obtained, will slightly produce
Object is put into heating, vacuum drying in baking oven, obtains final product, weight 118.3g, yield 91%.
(2) final product can be purified further, obtain double fluorine sulfimide salts that purity is greater than 99%, specific steps
As follows: with 236.6g methanol by final product stirring and dissolving described in 118.3g, -24 DEG C stand filtering for 24 hours, obtain solid precipitating and put
Enter vacuum drying in baking oven, obtain double fluorine sulfimide salts after purification, purity reaches 99% or more.
(3) the double fluorine sulfimides of the 3g N- pyrrole radicals of above method preparation are added in the electrolyte in comparative example, are made
At lithium secondary battery, the battery of the present embodiment 3 is obtained.
It is applied in lithium battery by the lithium battery electrolytes that method in embodiment 2 is prepared, by testing lithium battery
It is as shown in table 1 to obtain parameter.
Embodiment 4
On the basis of the electrolyte of comparative example addition account for the 0.4g of electrolyte gross mass the double fluorine sulfimides of N- phenyl and
The double methyl fluoride sulfimides of 1gN-3- picoline, obtain the electrolyte of the present embodiment.
It is applied in lithium battery by the lithium battery electrolytes that method in embodiment 4 is prepared, by testing lithium battery
It is as shown in table 1 to obtain parameter.
Embodiment 5
The double fluorine sulfimides of N- phenyl of 0.9g, the N- butyl -4- pyrrole of 0.6g are added on the basis of the electrolyte of comparative example
The double fluorine sulfimides of alkyl and the double fluorine sulfimides of N- piperidyl of 2g are coughed up, the electrolyte of the present embodiment is obtained.
It is applied in lithium battery by the lithium battery electrolytes that method in embodiment 5 is prepared, by testing lithium battery
It is as shown in table 1 to obtain parameter.
By comparative example and implement the battery testing room temperature 1C circulation performance of 1-5,45 DEG C of high temperature 1C circulation performances,
25 DEG C of 5C multiplying power discharging properties and -20 DEG C of low temperature 0.5C multiplying power discharging properties, test data are as shown in table 1:
1 the performance test results of table
As known from Table 1, the present invention can be bright by the electrolyte of the double fluorine sulfonyl imide compounds of addition electrolysis additive
Aobvious normal temperature circulation, high temperature circulation, multiplying power and the cryogenic property for improving lithium secondary battery.
Although having done more detailed elaboration to technical solution of the present invention and having enumerated, it should be understood that for ability
For field technique personnel, modifications to the embodiments described above may be made or uses equivalent alternative solution, this is to those skilled in the art
It is it is clear that these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to the present invention for member
Claimed range.
Claims (7)
1. a kind of preparation method of double fluorine sulfonyl imide compounds, which is characterized in that the preparation method the following steps are included:
(1) by FSO2X, nitrogen source, acid binding agent and aprotic solvent are mixed to get mixture；Wherein, nitrogen source is primary amine, and acid binding agent is
Non-proton organic amine；Acid binding agent and FSO2The molar ratio of X is 1:2~5；Nitrogen source and the molar ratio of acid binding agent are 1:3~8；Institute
Stating X is F or CnF2n+1, n=1-5；
(2) heating makes mixture back flow reaction, sustained response 12h~72h；
(3) cooling after back flow reaction, pressure release is spin-dried for solvent, water washing is added to filter, and obtains crude product；
(4) crude product is recrystallized, obtains the finished product of double fluorine sulfonyl imide compounds.
2. a kind of preparation method of double fluorine sulfonyl imide compounds according to claim 1, it is characterised in that: described to tie up
Sour agent is at least one of triethylamine, tetramethylethylenediamine, tetramethyl -1,3- propane diamine.
3. a kind of preparation method of double fluorine sulfonyl imide compounds according to claim 1, it is characterised in that: described non-
Proton solvent is acetone, methylene chloride, acetonitrile, dimethyl sulfoxide, N,N-dimethylformamide, ethylene carbonate, butylene carbonate
Ester, tetrahydrofuran, methyl formate, methyl acetate, methyl propionate, dimethyl carbonate, methyl ethyl carbonate, diethyl carbonate, ring fourth
Sulfone, ethyl acetate or butyl acetate.
4. a kind of preparation method of double fluorine sulfonyl imide compounds according to claim 1, it is characterised in that: the nitrogen
Source be aniline, meta-aminotoluene, phenyl ethylamine, 4- hexamethylene aniline, cyclohexylamine, 4- phenylbenzylamine, 2- aminobphenyl, 2-aminopyridine,
2- amino -3- picoline, 2-AMINO-4-PICOLINE, 2- amino -6- picoline, 2- amino-pyrroles, (S) -1-Cbz-3-
Amino-pyrrolidine, 4- pyrrolidines butylamine, (R) -1-BOC-3- aminomethyl pyrrolidine, N- ethyl-2-aminomethylpentazaneand, (S) -2-
(aminomethyl) pyrrolidines, 1- amino piperidine, 4- amino -1- methyl piperidine, 4- amino -1- benzyl piepridine, (S) -1- benzyl -3- ammonia
One of phenylpiperidines, (R) -3- amino -1-BOC- piperidines, (S) -1- tertbutyloxycarbonyl -3- amino piperidine are several.
5. a kind of preparation method of double fluorine sulfonyl imide compounds according to claim 1, it is characterised in that: described time
Stream reaction carries out at a temperature of -50 DEG C~100 DEG C, and reflux time is 18h~36h.
6. a kind of preparation method of double fluorine sulfonyl imide compounds according to claim 1, it is characterised in that: described heavy
The solvent of crystallization is one of ethyl alcohol, methanol, acetonitrile, ethyl acetate, 1,4- dioxane, toluene, benzene or several.
7. a kind of preparation method of double fluorine sulfonyl imide compounds according to claim 1, it is characterised in that: described double
The molecular formula of fluorine sulfonyl imide compounds finished product is RN (XSO2)2。
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110176631A (en) * | 2019-06-12 | 2019-08-27 | 广州天赐高新材料股份有限公司 | A kind of lithium secondary cell electrolyte and lithium secondary battery reducing the internal resistance of cell |
| CN111620315A (en) * | 2020-07-22 | 2020-09-04 | 上海华谊（集团）公司 | Preparation method of lithium bis (fluorosulfonyl) imide |
| CN113277487A (en) * | 2021-06-03 | 2021-08-20 | 上海如鲲新材料有限公司 | Preparation method of bis (fluorosulfonyl) imide salt solution |
| CN114044497A (en) * | 2022-01-13 | 2022-02-15 | 江苏笃行致远新材料科技有限公司 | Synthesis method of bis (fluorosulfonyl) imide |
| CN114560793A (en) * | 2022-03-11 | 2022-05-31 | 中山大学 | Free radical type fluorosulfonation reagent and preparation method and application thereof |
| US11591218B2 (en) | 2019-12-17 | 2023-02-28 | Honeywell International Inc. | Integrated processes for producing bis(fluorosulfonyl) imide |
| US11772967B2 (en) | 2021-01-07 | 2023-10-03 | Honeywell International Inc. | Integrated processes for treatment of an ammonium fluorosulfate byproduct of the production of bis (fluorosulfonyl) imide |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110176631A (en) * | 2019-06-12 | 2019-08-27 | 广州天赐高新材料股份有限公司 | A kind of lithium secondary cell electrolyte and lithium secondary battery reducing the internal resistance of cell |
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| CN111620315A (en) * | 2020-07-22 | 2020-09-04 | 上海华谊（集团）公司 | Preparation method of lithium bis (fluorosulfonyl) imide |
| US11772967B2 (en) | 2021-01-07 | 2023-10-03 | Honeywell International Inc. | Integrated processes for treatment of an ammonium fluorosulfate byproduct of the production of bis (fluorosulfonyl) imide |
| CN113277487A (en) * | 2021-06-03 | 2021-08-20 | 上海如鲲新材料有限公司 | Preparation method of bis (fluorosulfonyl) imide salt solution |
| CN114044497A (en) * | 2022-01-13 | 2022-02-15 | 江苏笃行致远新材料科技有限公司 | Synthesis method of bis (fluorosulfonyl) imide |
| CN114044497B (en) * | 2022-01-13 | 2022-03-22 | 江苏笃行致远新材料科技有限公司 | Synthesis method of bis (fluorosulfonyl) imide |
| CN114560793A (en) * | 2022-03-11 | 2022-05-31 | 中山大学 | Free radical type fluorosulfonation reagent and preparation method and application thereof |
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