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CN116854051B - Method for efficiently synthesizing difluoro sulfonyl imide by using eutectic solvent - Google Patents

Method for efficiently synthesizing difluoro sulfonyl imide by using eutectic solvent Download PDF

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CN116854051B
CN116854051B CN202310590151.6A CN202310590151A CN116854051B CN 116854051 B CN116854051 B CN 116854051B CN 202310590151 A CN202310590151 A CN 202310590151A CN 116854051 B CN116854051 B CN 116854051B
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reaction
tert
eutectic solvent
fluorosulfonyl
butyl
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CN116854051A (en
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毛卫青
孙鹏
章浩
陈盛团
曹国斌
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Feili Intelligent Equipment Zhejiang Co ltd
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    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01BNON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B21/00Nitrogen; Compounds thereof
    • C01B21/082Compounds containing nitrogen and non-metals and optionally metals
    • C01B21/087Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
    • C01B21/093Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01PINDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00Crystal-structural characteristics
    • C01P2002/80Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70
    • C01P2002/86Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70 by NMR- or ESR-data
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01PINDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00Physical properties of inorganic compounds
    • C01P2006/80Compositional purity

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Abstract

The invention discloses a method for efficiently synthesizing difluoro sulfonyl imide by using a eutectic solvent, which takes tert-butyl carbamate and sulfuryl fluoride gas as raw materials to react to generate di (fluoro sulfonyl) carbamic acid tert-butyl ester, and then efficiently deprotecting a protecting group in the eutectic solvent to generate difluoro sulfonyl imide, and has the advantages of mild reaction condition, simple post-treatment operation, high purity and yield, and very good industrial production application prospect.

Description

Method for efficiently synthesizing difluoro sulfonyl imide by using eutectic solvent
Technical Field
The invention relates to the field of fine chemical synthesis, in particular to a method for efficiently synthesizing difluoro sulfimide by using a eutectic solvent.
Background
The lithium ion battery has the advantages of high energy density, high working voltage, long cycle life and the like, and is widely applied to the fields of mobile phones, notebook computers, electric automobiles and the like, and the application field of the lithium ion battery is continuously expanded along with the continuous development of society. Lithium bis (fluorosulfonyl imide) (LiFSI) is one of the new lithium salts with a clear prospect of development at present, and is considered to be a new fluorine-containing lithium salt that is likely to become the main component of the next-generation electrolyte. Compared with lithium hexafluorophosphate, the decomposition temperature of LiFSI is higher, and the corrosion of electrolyte to the current collector can be reduced. The bisfluorosulfonyl imide is an important intermediate for preparing lithium bisfluorosulfonyl imide (LiFSI), and has the structural formula: The current preparation method for preparing the difluoro sulfimide mainly comprises the following steps: sulfuryl chloride reacts with ammonia gas, aromatic amine or hydroxylamine reacts with fluoro sulfuryl; and reacting the dichlorosulfimide with fluoride ions.
CN104925765A discloses a method for preparing bis (fluorosulfonyl) imide by high-temperature and high-pressure fluorination of bis (chlorosulfonyl) imide and hydrogen fluoride, which has high requirements on equipment and high process risk; chlorosulfonic acid often remains in the synthesized bischlorosulfimide, and is extremely difficult to remove.
CN106044718a discloses a process for preparing bischlorosulfonimide from chlorosulfonic acid and isonitrile chlorosulfonate in the presence of catalyst (NiCl 2, concentrated sulfuric acid, anhydrous FeCl 3), reacting at 100-150 ℃ for 20-30 h, yield 83-95%, but the process requires catalyst and has long reaction time.
CN104925765A discloses that dichlorosulfimide and a catalyst (SbCl 5, tiCl4, snCl4, moCl5, etc.) are placed in a reaction apparatus, and HF gas is introduced to react, with a yield of 90%. However, the method has higher requirements on equipment, and the use of the catalyst introduces impurity ions, so that the process is complicated in operation and high in risk.
CN114044497B discloses a synthesis method of bis-fluoro-sulfonyl imide, comprising the following steps: 1) Reacting benzylamine compounds with sulfuryl fluoride in the presence of a catalyst and alkali in a solvent to generate N-benzyl difluoro sulfimide compounds; 2) And carrying out catalytic hydrogenation reaction on the N-benzyl difluoro sulfonimide compound to obtain difluoro sulfonimide. However, the first step of the method requires an additional catalyst in addition to the base; the deprotection groups in the second step have strict requirements on reaction conditions, long reaction time, use of hydrogen, need to be carried out in a high-temperature and high-pressure environment, and have high requirements on equipment and strong dangers.
Aiming at the problems of harsh reaction conditions, low yield and purity, strong danger and the like in the prior art, the development of a method for efficiently synthesizing difluoro sulfimide is needed.
Disclosure of Invention
The invention aims to provide a method for efficiently synthesizing difluoro-sulfonyl imide by using a eutectic solvent.
In order to achieve the above purpose, the present invention provides the following specific technical solutions:
a method for efficiently synthesizing difluoro sulfonyl imide by using a eutectic solvent, which is characterized by comprising the following steps of:
1) Reacting tert-butyl carbamate with sulfuryl fluoride gas in the presence of a base to produce di (fluorosulfonyl) tert-butyl carbamate;
2) Heating choline chloride and propionic acid to 40-70 ℃ to form a eutectic solvent, and then reacting with di (fluorosulfonyl) carbamic acid tert-butyl ester to generate difluoro-sulfonyl imide;
The reaction route is as follows:
in some embodiments, the base of step 1) is selected from sodium hydroxide, potassium hydroxide, sodium hydrogen sodium or potassium hydride, preferably sodium hydroxide, sodium hydride.
In some embodiments, the molar ratio of t-butyl carbamate to sulfuryl fluoride of step 1) is 1 (2-5), preferably 1 (2-3); the molar ratio of tert-butyl carbamate to base is 1 (1-3), preferably 1:2.
In some embodiments, step 1) reaction solvent is selected from DMSO, DMF, THF, toluene, ethyl acetate, dichloromethane, chloroform.
In some embodiments, the reaction temperature is 30 to 60 ℃, preferably 50 ℃. The reaction time is preferably overnight.
In some embodiments, step 1) operates specifically as: adding tert-butyl carbamate into a reaction solvent, adding alkali at 0-10 ℃ and stirring for a period of time, then introducing sulfuryl fluoride gas, and stirring at 30-60 ℃ for reaction overnight; adding water to quench reaction, extracting, concentrating and drying to obtain the di (fluorosulfonyl) carbamic acid tert-butyl ester.
In some embodiments, the post-treatment operation of step 1) and its conditions are all selectable by one skilled in the art. The extraction solvent is preferably ethyl acetate.
In some embodiments, the choline chloride and propionic acid in step 2) are in a molar ratio of 1 (1-3), preferably 1 (1-2).
In some embodiments, step 2) is performed at a reaction temperature of 40 to 80℃for a reaction time of 10 to 30 minutes.
In some embodiments, step 2) specifically operates as: adding choline chloride and propionic acid into a round-bottomed flask, heating to 50-70 ℃ and stirring for a period of time to form a uniform and clear eutectic solvent; then adding the crude product of the tertiary butyl bis (fluorosulfonyl) carbamate for reaction; after the reaction, adding a proper amount of 5% sodium bicarbonate aqueous solution, extracting, concentrating under reduced pressure, and drying in vacuum to obtain the difluoro sulfimide.
In some embodiments, the post-treatment operation of step 2) and its conditions are all selectable by one skilled in the art. The extraction solvent is preferably ethyl acetate.
The invention has the following beneficial effects:
1) According to the invention, tert-butyl carbamate and sulfuryl fluoride gas are used as raw materials to react to generate di (fluoro sulfonyl) carbamic acid tert-butyl ester, and then deprotection is carried out to generate difluoro sulfonyl imide, the reaction condition is mild, the post-treatment operation is simple, and the reaction process can be carried out at low temperature without hydrogen.
2) According to the invention, choline chloride is used as a hydrogen bond acceptor, acetic acid is used as a hydrogen bond donor, and the uniform eutectic solvent is formed by heating, and the melting point of the eutectic solvent is obviously lower than that of each single component, so that the eutectic solvent can be regarded as a novel ionic liquid. The eutectic solvent can be used as a solvent, has the advantages of low cost, easy preparation, low toxicity and the like, can be used as a catalyst for efficiently catalyzing di (fluorosulfonyl) carbamic acid tert-butyl ester to remove boc protecting groups to generate difluoro sulfonyl imide, has mild reaction conditions, can be completed in a short time at a low temperature, has high yield and purity, and has good industrial production application prospect.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be further described in detail with reference to specific examples and comparative examples. The specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. Those skilled in the art will recognize that: the chemical reactions described herein may be used to suitably prepare other compounds of the present invention, and other methods for preparing compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of those non-exemplified compounds according to the invention can be successfully accomplished by modification methods, such as appropriate protection of interfering groups, by use of other known reagents in addition to those described herein, or by some conventional modification of the reaction conditions, by those skilled in the art. In addition, the reactions disclosed herein or known reaction conditions are also well-known to be applicable to the preparation of other compounds of the present invention.
Example 1:
Tert-butyl carbamate (11.7 g,0.1 mol) was added to dichloromethane (200 mL), naH (4.8 g,0.2 mol) was added at 0deg.C and stirred for 0.5h, followed by sulfuryl fluoride gas (25.5 g,0.25 mol), and the reaction was heated to 50deg.C and stirred overnight. The reaction was quenched with water (100 mL), extracted with ethyl acetate (200 mL. Times.3), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude t-butyl bis (fluorosulfonyl) carbamate, which was then directly subjected to the next reaction.
Choline chloride (13.95 g,0.1 mol) and propionic acid (14.8 g,0.2 mol) were added to a 100mL round bottom flask, heated to 50 ℃ and stirred for 0.5h to form a homogeneous clear eutectic solvent. Then adding the crude product of the di (fluorosulfonyl) carbamic acid tert-butyl ester, and stirring and reacting for 15min at 50 ℃. After the reaction, 100mL of 5% aqueous sodium hydrogencarbonate solution was added, extracted with ethyl acetate (200 mL. Times.3), and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and dried under vacuum to give 17.32g of difluorosulfimide in a yield of 95.7% and a purity of 99.7%.
LC-MS(ESI):[M+H]+=182.2。
1HNMR(500MHz,CDCl3)δ:7.80(s,1H);19FNMR(500MHz,CDCl3)δ:54.1。
Example 2
Tert-butyl carbamate (11.7 g,0.1 mol) was added to chloroform (200 mL), sodium hydroxide (8.0 g,0.2 mol) was added at 0deg.C and stirred for 0.5h, followed by sulfuryl fluoride gas (30.6 g,0.30 mol), and the mixture was heated to 50deg.C and stirred overnight. The reaction was quenched with water (100 mL), extracted with ethyl acetate (200 mL. Times.3), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude t-butyl bis (fluorosulfonyl) carbamate, which was then directly subjected to the next reaction.
Choline chloride (13.95 g,0.1 mol) and propionic acid (14.8 g,0.2 mol) were added to a 100mL round bottom flask, heated to 60 ℃ and stirred for 0.5h to form a homogeneous clear eutectic solvent. Then adding the crude product of the di (fluorosulfonyl) carbamic acid tert-butyl ester, and stirring and reacting for 30min at 60 ℃. After the reaction, 100mL of 5% aqueous sodium hydrogencarbonate was added, extracted with ethyl acetate (200 mL. Times.3), and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and dried under vacuum to give 16.92g of bisfluorosulfonyl imide in 93.5% yield and 99.4% purity.
Example 3
Tert-butyl carbamate (11.7 g,0.1 mol) was added to tetrahydrofuran (200 mL), sodium hydroxide (8.0 g,0.2 mol) was added at 0deg.C and stirred for 0.5h, followed by sulfuryl fluoride gas (30.6 g,0.30 mol), and the reaction was heated to 50deg.C and stirred overnight. The reaction was quenched with water (100 mL), extracted with ethyl acetate (200 mL. Times.3), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude t-butyl bis (fluorosulfonyl) carbamate, which was then directly subjected to the next reaction.
Choline chloride (13.95 g,0.1 mol) and propionic acid (7.4 g,0.1 mol) were added to a 100mL round bottom flask, heated to 55 ℃ and stirred for 0.5h to form a homogeneous clear eutectic solvent. Then adding the crude product of the di (fluorosulfonyl) carbamic acid tert-butyl ester, and stirring and reacting for 20min at 60 ℃. After the reaction, 100mL of 5% aqueous sodium hydrogencarbonate was added, extracted with ethyl acetate (200 mL. Times.3), and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and dried under vacuum to give 16.72g of bisfluorosulfonyl imide in 92.4% yield and 99.5% purity.
Comparative example 1
The common amino deprotection reagent trifluoroacetic acid was replaced with a eutectic solvent of choline chloride and propionic acid, and the other conditions were substantially the same as in example 1, specifically as follows:
Tert-butyl carbamate (11.7 g,0.1 mol) was added to dichloromethane (200 mL), naH (4.8 g,0.2 mol) was added at 0deg.C and stirred for 0.5h, followed by sulfuryl fluoride gas (25.5 g,0.25 mol), and the reaction was heated to 50deg.C and stirred overnight. The reaction was quenched with water (100 mL), extracted with ethyl acetate (200 mL. Times.3), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude t-butyl bis (fluorosulfonyl) carbamate, which was then directly subjected to the next reaction.
Trifluoroacetic acid (22.8 g,0.2 mol) was added to a 100mL round bottom flask, followed by the above crude t-butyl bis (fluorosulfonyl) carbamate and the reaction stirred at 50℃for 15min. After the reaction, 100mL of 5% aqueous sodium hydrogencarbonate was added, extracted with ethyl acetate (200 mL. Times.3), and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and dried under vacuum to give 7.62g of difluorosulfimide in a yield of 42.1% and a purity of 97.5%.
The above examples are presented for clarity of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. And thus obvious variations or modifications to the disclosure are within the scope of the invention.

Claims (8)

1. A method for efficiently synthesizing difluoro sulfonyl imide by using a eutectic solvent, which is characterized by comprising the following steps of:
1) Reacting tert-butyl carbamate with sulfuryl fluoride gas in the presence of strong alkali to generate di (fluorosulfonyl) tert-butyl carbamate;
2) Heating choline chloride and propionic acid to 40-70 ℃ to form a uniform eutectic solvent, and then reacting with di (fluorosulfonyl) carbamic acid tert-butyl ester to generate difluoro-sulfonyl imide;
The reaction route is as follows:
2. The method according to claim 1, characterized in that: the strong base in step 1) is selected from sodium hydroxide, potassium hydroxide, sodium hydride or potassium hydride.
3. The method according to claim 1, characterized in that: the molar ratio of the tert-butyl carbamate to the sulfuryl fluoride in the step 1) is 1 (2-5); the molar ratio of the tert-butyl carbamate to the alkali is 1 (1-3).
4. The method according to claim 1, characterized in that: step 1) the reaction solvent is selected from DMSO, DMF, THF, toluene, ethyl acetate, methylene dichloride, chloroform and acetonitrile; the reaction temperature is 30-60 ℃.
5. The method according to claim 1, characterized in that: step 1) is specifically performed as follows: adding tert-butyl carbamate into a reaction solvent, adding alkali at 0-10 ℃ and stirring for a period of time, then introducing sulfuryl fluoride gas, and stirring at 30-60 ℃ for reaction overnight; adding water to quench reaction, extracting, concentrating and drying to obtain the di (fluorosulfonyl) carbamic acid tert-butyl ester.
6. The method according to claim 1, characterized in that: the mol ratio of the choline chloride to the propionic acid in the step 2) is 1 (1-3).
7. The method according to claim 1, characterized in that: the reaction temperature of the step 2) is 40-80 ℃ and the reaction time is 10-30 min.
8. The method according to claim 1, characterized in that: the specific operation of the step 2) is as follows: adding choline chloride and propionic acid into a round-bottomed flask, heating to 50-70 ℃ and stirring for a period of time to form a uniform eutectic solvent; then adding the crude product of the tertiary butyl bis (fluorosulfonyl) carbamate for reaction; after the reaction, adding a proper amount of 5% sodium bicarbonate aqueous solution, extracting, concentrating under reduced pressure, and drying in vacuum to obtain the difluoro sulfimide.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN114506829A (en) * 2022-03-01 2022-05-17 国药集团化学试剂有限公司 Preparation method of lithium bis (fluorosulfonyl) imide

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JP6343364B2 (en) * 2017-04-19 2018-06-13 日東電工株式会社 Adhesive composition and adhesive sheet
CN108946686A (en) * 2018-07-31 2018-12-07 九江天赐高新材料有限公司 A kind of preparation method of double fluorine sulfimide lithiums
WO2022017975A1 (en) * 2020-07-18 2022-01-27 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
KR20220057144A (en) * 2020-10-29 2022-05-09 엘티소재주식회사 Method for producing bisfluorosulfonyl imide alkali metal salt and bisfluorosulfonyl imide alkali metal salt produced by same
CN115974013A (en) * 2022-12-30 2023-04-18 浙江研一新能源科技有限公司 Preparation method of bis (fluorosulfonyl) imide and preparation method of bis (fluorosulfonyl) imide salt

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN114506829A (en) * 2022-03-01 2022-05-17 国药集团化学试剂有限公司 Preparation method of lithium bis (fluorosulfonyl) imide

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