Process for the preparation of n-(fluorosulfonyl)dimethylamine

Abstract

This invention relates to a method for preparing N-(fluorosulfonyl)dimethylamine, the method comprising: contacting thioyl fluoride with dimethylamine in the presence of an inorganic base to react and form N-(fluorosulfonyl)dimethylamine. The method of this invention allows for the simpler, more efficient, and lower-cost preparation of N-(fluorosulfonyl)dimethylamine.

Description

Technical Field

[0001] This invention relates to the field of electrolytes for secondary batteries, and specifically to a method for preparing N-(fluorosulfonyl)dimethylamine. Background Technology

[0002] In the 1930s, N-(fluorosulfonyl)dimethylamine (FSO2NMe2) was first prepared by a substitution reaction between N-(chlorosulfonyl)dimethylamine (ClSO2NMe2) and potassium, sodium, or zinc fluorides in water. FSO2NMe2 was also prepared by reacting ClSO2NMe2 with antimony trifluoride (SbF3) in the presence of antimony pentafluoride (SbF5), and by reacting ClSO2NMe2 with anhydrous HF at 80-90°C. Furthermore, FSO2NMe2 was also prepared by reacting N,N-dimethylaminosulfonamide (Me2NSO2NH2) with fluorosulfonyl isocyanate (FSO2N=C=O) at 80°C. In addition, four other examples exist of the reaction of sulfuryl fluoride (SO2F2) with secondary amines, which utilize a refrigerant (or catalyst). In 1948, the first reaction of SO2F2 with a secondary amine was carried out: diethylamine (Et2NH) was added dropwise to a cooled (-78°C) ether solution of SO2F2 to give the product FSO2NEt2 in a yield of 35%. In 1982, the reaction of SO2F2 with piperidine (HN(CH2)5) was carried out: SO2F2 was added to piperidine in ether at liquid nitrogen temperature, and then heated; depending on the amount of piperidine used, FSO2N(CH2)5 or SO2(N(CH2)5)2 was obtained.

[0003] WO2015 / 188120 describes the reactions of two other secondary amines with SO2F2 under ambient conditions. Specifically, diallylamine and dialysylamine react with SO2F2 in a solvent in the presence of an equimolar amount of an activator, such as tetrahydrofuran (THF) or dichloromethane. Furthermore, WO2015 / 188120 mentions that the activated amines can react in a buffer solution at pH 8, but no examples of activated amines are given.

[0004] CN109563031A provides a method for synthesizing N-(fluorosulfonyl)dimethylamine: dimethylamine (Me2NH) is reacted with sulfuryl fluoride (SO2F2) to form at least a first phase, the first phase comprising N-(fluorosulfonyl)dimethylamine (FSO2NMe2), tetramethylsulfonamide (SO2(NMe2)2), or a combination thereof. The reaction can also form a second phase, which may contain dimethylamine hydrofluoride (Me2NH2F), which can be separated from the first phase. Subsequently, FSO2NMe2 and SO2(NMe2)2 are separated from the first phase. However, due to limitations in the reactants and starting materials, the fluorine conversion rate is low. Furthermore, this reaction employs a two-step process, requiring the dimethylamine hydrofluoride (Me2NH2F) in the second phase to be recovered and reused using organic or inorganic alkaline solutions. That is, the remaining product Me2NH2F needs to be recovered and reused, increasing the complexity of the reaction and reducing its efficiency.

[0005] Therefore, there is a need for a simpler, more efficient, and lower-cost method for preparing N-(fluorosulfonyl)dimethylamine. Summary of the Invention

[0006] The purpose of this invention is to provide a method for preparing N-(fluorosulfonyl)dimethylamine (FSA). This method involves adding an appropriate amount of inorganic base (such as NaOH or LiOH) as an acid-binding agent to a reactor to promote the reaction of dimethylamine (Me2NH) with sulfuryl fluoride (SO2F2), thereby generating N-(fluorosulfonyl)dimethylamine efficiently and selectively.

[0007] On one hand, the present invention provides a method for preparing N-(fluorosulfonyl)dimethylamine, the method comprising: contacting thioyl fluoride with dimethylamine in the presence of an inorganic base to react and form N-(fluorosulfonyl)dimethylamine.

[0008] In a specific implementation, the method includes:

[0009] (1) The inorganic base is mixed with dimethylamine to form a homogeneous mixture comprising the inorganic base and dimethylamine; and

[0010] (2) Thionyl fluoride is introduced into the mixture to form N-(fluorosulfonyl)dimethylamine.

[0011] In a specific embodiment, step (2) includes: introducing thioyl fluoride into the mixture at a rate sufficient to control the temperature of the reaction between -30°C and 110°C; and / or

[0012] Under stirring and / or aeration, thioyl fluoride is introduced into the mixture, and the reaction forms N-(fluorosulfonyl)dimethylamine.

[0013] In a specific implementation, the method includes:

[0014] (a) An inorganic base is added to dimethylamine to form a heterogeneous mixture comprising a first inorganic phase and a second organic phase, wherein the first inorganic phase comprises an inorganic base and the second organic phase comprises dimethylamine; and

[0015] (b) Introducing thioyl fluoride into the second organic phase, reacting to form a product containing N-(fluorosulfonyl)dimethylamine.

[0016] In a specific embodiment, step (b) includes: introducing thioyl fluoride into a second organic phase at a location adjacent to the first organic phase, causing a local reaction in the second organic phase to form N-(fluorosulfonyl)dimethylamine; and / or

[0017] Thionyl fluoride is introduced into the second organic phase at a rate sufficient to control the temperature of the reaction between -30°C and 110°C.

[0018] In a specific implementation, the method further includes:

[0019] (c) The product formed in step (b) of stirring promotes the continued reaction.

[0020] In a specific embodiment, the inorganic base is selected from at least one of LiOH, KOH, NaOH, Na2CO3, and NaHCO3.

[0021] In a specific embodiment, the inorganic base, dimethylamine, and thioyl fluoride react in a molar ratio of 0.1:1:0.1 to 2:1:2.

[0022] In a specific embodiment, the dimethylamine is selected from pure dimethylamine or a polar solution of dimethylamine.

[0023] In a specific embodiment, the reaction uses a solvent as a carrier, and the solvent is selected from water, methanol, ethanol, and any combination thereof.

[0024] In a specific implementation, the reaction is carried out in a batch process or a continuous process.

[0025] Compared with the prior art, the dimethylamine utilization rate of the method described in this invention can be increased to 100%, and the preparation process of N-(fluorosulfonyl)dimethylamine is simplified and made more efficient.

[0026] Other features and aspects will become clear from the following detailed description and the claims. Detailed Implementation

[0027] Unless otherwise defined, the technical or scientific terms used in the claims and description shall have the ordinary meaning as understood by one of ordinary skill in the art to which this invention pertains.

[0028] In this document, the term “about” used to modify, for example, the amount, concentration, process temperature, process time, flow rate, and similar values ​​and ranges of an ingredient in a composition, or the scale and similar values ​​and ranges of a component, refers to possible changes in numerical values, such as those arising from routine measurements and operations used in the manufacture or use of formulations for preparing materials, compositions, complexes, concentrates, components, articles; accidental errors in these processes; differences in the purity or composition of the manufacturing, source, or starting materials used to carry out the method; and similar factors.

[0029] In this document, when a numerical range such as 5-25 is given, this means at least 5 or not less than 5 and separately and independently not greater than or less than 25. In some embodiments, such a range may be independently defined as not less than 5 and separately and independently not greater than 25. Values ​​having such a range, such as 10, -15, or 10-20, also include the lower and upper limits of the range separately and independently in the same manner.

[0030] As used herein, unless otherwise specified, “% by weight” or “percentage by weight” for a component refers to the total weight of the composition or article containing that component. Terms such as “comprising” or “including” indicate that the elements or articles preceding “comprising” or “including” encompass the elements or articles listed following “comprising” or “including” and their equivalents, and do not exclude other elements or articles.

[0031] In this invention, the term "pure dimethylamine" generally refers to dimethylamine with a purity of 99% or higher. The term "pure FSO2NMe2" generally refers to FSO2NMe2 with a purity of 99% or higher.

[0032] In existing technologies for preparing FSA using SO2F2, direct contact between SO2F2 and inorganic alkalis is avoided (i.e., inorganic alkalis such as NaOH are not used as acid-binding agents). This is because SO2F2 can undergo unpredictable chemical reactions with inorganic alkali solutions, generating unwanted byproducts and potentially producing toxic, harmful, or explosive gases, increasing the safety risks of the preparation process. On the other hand, existing technologies for preparing FSA using SO2F2 often employ organic alkalis for the reaction, or divide the reaction into two steps or two pots, adding inorganic alkalis such as NaOH to the generated Me2NH2F for MeNH2 recovery, making the operation process relatively complex. In this invention, the inventors cleverly utilize the high solubility of SO2F2 in DMA. When DMA and inorganic base are directly mixed, SO2F2 is slowly introduced, allowing SO2F2 and DMA to react fully first. At the same time, the product Me2NH2F after the reaction comes into contact with and reacts with inorganic base (e.g., NaOH / LiOH) to generate Me2NH, H2O, and NaF / LiF. NaF / LiF has very low solubility and can be removed by direct filtration, while Me2NH can be directly recycled.

[0033] Furthermore, compared to the technical approach of adding an organic base in the reaction of SO2F2 and dimethylamine, this invention uses an inorganic base such as NaOH for the reaction, eliminating the step of further reaction and recovery of the organic base in the reactants. It also eliminates the need for distillation, purification, and concentration steps, simplifying the operation. Moreover, since organic bases are prone to volatilization during long-term recovery, this invention, using an inorganic base such as NaOH, also avoids the generation of waste gas.

[0034] As mentioned above, the reaction products with low solubility, such as NaF, generated by the reaction with inorganic bases such as NaOH are easily filtered out directly. The remaining reaction products, FSO2NMe2, are organic matter and water, which can be separated into layers for easy classification and treatment. This simplifies the reaction operation steps, reduces the amount of reaction equipment, lowers energy consumption, and reduces costs.

[0035] Furthermore, compared with conventional techniques involving SO2F2 and dimethylamine (such as CN109563031A), this invention can improve the utilization rate of dimethylamine, increasing it from 50% to 100%.

[0036] Finally, this invention utilizes the high solubility of SO2F2 in DMA to achieve a highly efficient reaction by directly mixing it with an inorganic base (such as NaOH / LiOH) and slowly introducing SO2F2. This avoids the safety risks that may result from direct contact between SO2F2 and the inorganic base, simplifies the reaction process, eliminates the need for organic base recovery and subsequent treatment, reduces waste gas emissions, and makes the generated byproducts easy to filter and separate, thus reducing energy consumption and costs and improving the overall economic and environmental benefits of the process.

[0037] This invention provides a method for preparing N-(fluorosulfonyl)dimethylamine, the method comprising: contacting thioyl fluoride with dimethylamine in the presence of an inorganic base to react and form N-(fluorosulfonyl)dimethylamine.

[0038] In one embodiment of the present invention, the preparation method of N-(fluorosulfonyl)dimethylamine can be carried out by a homogeneous reaction method, comprising: (1) mixing the inorganic base with dimethylamine to form a homogeneous mixture containing the inorganic base and dimethylamine; and (2) introducing thioyl fluoride into the mixture to react and form N-(fluorosulfonyl)dimethylamine. In a specific embodiment, the inorganic base is selected from at least one of LiOH, KOH, NaOH, Na2CO3, and NaHCO3. In a specific embodiment, the inorganic base, dimethylamine, and thioyl fluoride react in a molar ratio of 0.1:1:0.1 to 2:1:2, 0.3:1:0.3 to 1.8:1:1.8, 0.5:1:0.5 to 1.5:1:1.5, or 0.8:1:0.8 to 1.2:1:1.2. In this invention, the inorganic base, dimethylamine, and thiosulfate fluoride, when arranged in the aforementioned molar ratio range, can more effectively improve the utilization rate of dimethylamine in the reaction raw materials, increasing its theoretical utilization rate to 100%. In a specific embodiment, the dimethylamine is selected from pure dimethylamine or a polar solution of dimethylamine, wherein the polar solvent can be selected from water, methanol, ethanol, and any combination thereof. In a specific embodiment, the reaction can be carried out in a solvent, wherein the solvent is selected from water, methanol, ethanol, and any combination thereof. In a specific embodiment, the reaction is carried out in a batch process (batch reactor) or a continuous process (continuous flow reactor). In some embodiments, the reaction is carried out in an open or sealed reactor. In a specific embodiment, step (2) includes: introducing thioyl fluoride into the mixture at a rate sufficient to control the temperature of the reaction between -30°C and 110°C, between -20°C and 100°C, between -10°C and 90°C, between 0°C and 80°C, between 10°C and 70°C, between 20°C and 60°C, or between room temperature and 50°C; and / or introducing thioyl fluoride into the mixture under stirring and / or aeration conditions, reacting to form N-(fluorosulfonyl)dimethylamine.

[0039] In some embodiments, the preparation method of N-(fluorosulfonyl)dimethylamine further includes: (3) post-treatment of the reaction solution (e.g., filtration, distillation, extraction, etc.) to separate and purify N-(fluorosulfonyl)dimethylamine (FSO2NMe2). By filtration, insoluble substances such as NaF / LiF generated in the reaction are separated, while the generated Me2NH and H2O are recycled and reused in the reactor, which improves the utilization rate of the reactants and does not generate wastewater.

[0040] In a specific embodiment, the preparation method of N-(fluorosulfonyl)dimethylamine includes: (i) adding an appropriate amount of inorganic base (such as NaOH, LiOH) and dimethylamine (Me2NH) solution to a reactor, stirring thoroughly to ensure that the two are fully miscible; (ii) slowly introducing an appropriate amount of sulfuryl fluoride (SO2F2) gas, controlling the introduction rate to maintain the temperature of the reaction system and avoid local overheating or explosion; (iii) under stirring and gas-purifying conditions, allowing dimethylamine (Me2NH) and sulfuryl fluoride (SO2F2) to react fully under the catalysis of the inorganic base until the reaction is completed; (iv) filtering, distilling and extracting the reaction solution to separate and purify N-(fluorosulfonyl)dimethylamine (FSO2NMe2).

[0041] During the reaction, thorough stirring ensures that dimethylamine and sulfuryl fluoride react fully. Simultaneously, the generated Me2NH2F comes into contact with and reacts with the inorganic base NaOH / LiOH to produce Me2NH, H2O, and NaF / LiF.

[0042] In another embodiment of the present invention, the preparation method of N-(fluorosulfonyl)dimethylamine can be carried out according to a heterogeneous reaction method, comprising: (a) adding an inorganic base to dimethylamine to form a heterogeneous mixture comprising a first inorganic phase and a second organic phase, wherein the first inorganic phase comprises an inorganic base and the second organic phase comprises dimethylamine; and (b) introducing thioyl fluoride into the second organic phase to react and form a product comprising N-(fluorosulfonyl)dimethylamine. In a specific embodiment, the inorganic base is selected from at least one of LiOH, KOH, NaOH, Na2CO3, and NaHCO3. In a specific embodiment, the inorganic base, dimethylamine, and thioyl fluoride react in a molar ratio of 0.1:1:0.1 to 2:1:2, 0.3:1:0.3 to 1.8:1:1.8, 0.5:1:0.5 to 1.5:1:1.5, or 0.8:1:0.8 to 1.2:1:1.2. In this invention, the inorganic base, dimethylamine, and thiosulfonyl fluoride, when in the aforementioned molar ratio range, can more effectively improve the utilization rate of dimethylamine in the reaction raw materials, increasing its theoretical utilization rate to 100%. In a specific embodiment, the dimethylamine is selected from pure dimethylamine or a polar solution of dimethylamine, wherein the polar solvent can be selected from water, methanol, ethanol, and any combination thereof. In a specific embodiment, the reaction can be carried out in a solvent, wherein the solvent is selected from water, methanol, ethanol, and any combination thereof. In a specific embodiment, the reaction is carried out in a batch process (batch reactor) or a continuous process (continuous flow reactor). In some embodiments, the reaction is carried out in an open or sealed reactor. In a specific embodiment, step (b) includes: introducing thiosulfonyl fluoride into a second organic phase adjacent to the first organic phase, where a local reaction occurs to form N-(fluorosulfonyl)dimethylamine. In a specific embodiment, step (2) includes: introducing thioyl fluoride into the mixture at a rate sufficient to control the temperature of the reaction between -30°C and 110°C, between -20°C and 100°C, between -10°C and 90°C, between 0°C and 80°C, between 10°C and 70°C, between 20°C and 60°C, or between room temperature and 50°C; and / or introducing thioyl fluoride into the mixture under stirring and / or aeration conditions, reacting to form N-(fluorosulfonyl)dimethylamine.

[0043] In specific embodiments, the method further includes: (c) stirring the product formed in step (b) to promote the continued reaction. In some embodiments, the method for preparing N-(fluorosulfonyl)dimethylamine further includes: (d) post-treatment of the reaction solution (e.g., filtration, distillation, extraction, etc.) to separate and purify N-(fluorosulfonyl)dimethylamine (FSO2NMe2). Filtration separates insoluble substances such as NaF / LiF generated in the reaction, while the generated Me2NH and H2O are recycled in the reactor, improving the utilization rate of the reactants and preventing wastewater generation.

[0044] In the following, the preparation of N-(fluorosulfonyl)dimethylamine using the method of the present invention is characterized based on specific embodiments. However, it should be specifically noted that the scope of protection of this application is defined by the claims, and not limited to the specific embodiments.

[0045] Example

[0046] General steps:

[0047] Dimethylamine was added to the reactor, along with an inorganic base as an acid-binding agent (in the comparative example, an organic base was added or no base was added), the reactor was cooled, and evacuated to a constant static pressure. Thionyl fluoride was introduced into the mixture under maximum stirring, and the reactor was cooled to maintain the temperature. At the end of the reaction, the high-pressure reactor was vented, opened, and the contents were separated using a funnel. The lower layer was subjected to vacuum distillation to obtain pure FSO2NMe2.

[0048] Example 1.

[0049] Example 1: Uniform mixing method, NaOH is added as an inorganic base as an acid-binding agent in the initial reaction.

[0050] Reactants: SO2F2 and Me2NH,

[0051] Reaction process: SO2F2 + Me2NH + NaOH = FSO2NMe2 + NaF

[0052] As shown in Table 1, dimethylamine was added to the reactor, along with NaOH aqueous solution as an acid-binding agent. The reactor was cooled and evacuated to a constant static pressure. Thionyl fluoride was introduced into the mixture under stirring, and the reactor was cooled to maintain a reaction temperature of T = 30°C. The pressure was set to P = 20 kPa, and the reaction time was t = 30 minutes. At the end of the reaction, the high-pressure reactor was vented, opened, filtered, and the contents were separated using a funnel. The lower layer was subjected to vacuum distillation to obtain pure FSO₂NMe₂. The yield of FSO₂NMe₂ and the utilization rate of dimethylamine were measured.

[0053] Final products: Only the final products of the first phase, H2O and NaF insoluble substances, with no other byproducts.

[0054] Technical benefits: In Example 1, the utilization rate of dimethylamine was increased to 96%, eliminating the need for recycling and reuse of intermediate products, making the reaction simpler and saving processing time.

[0055] Example 2: Uniform mixing method, KOH is added as an inorganic base as an acid-binding agent in the initial reaction.

[0056] Reactants: SO2F2 and Me2NH,

[0057] Reaction process: SO2F2 + Me2NH + KOH = FSO2NMe2 + KF

[0058] As shown in Table 1, dimethylamine was added to the reactor, along with KOH aqueous solution as an acid-binding agent. The reactor was cooled and evacuated to a constant static pressure. Thionyl fluoride was introduced into the mixture under maximum stirring, and the reactor was cooled to maintain a reaction temperature of T = 30°C. The pressure was set to P = 20 kPa, and the reaction time was t = 30 minutes. At the end of the reaction, the high-pressure reactor was vented, opened, filtered, and the contents were separated using a funnel. The lower layer was subjected to vacuum distillation to obtain pure FSO₂NMe₂. The yield of FSO₂NMe₂ and the utilization rate of dimethylamine were measured.

[0059] Final products: Only the final products of the first phase, H2O and KF insoluble substances, with no other byproducts.

[0060] Technical benefits: In Example 2, the utilization rate of dimethylamine was increased to 94%, eliminating the need for recycling and reuse of intermediate products, making the reaction simpler and saving processing time.

[0061] Example 3: Heterogeneous mixing homogenization method, in which NaOH is added as an inorganic base as an acid-binding agent in the initial reaction.

[0062] Reactants: SO2F2 and Me2NH,

[0063] Reaction process: SO2F2 + Me2NH + NaOH = FSO2NMe2 + NaF

[0064] As shown in Table 1, dimethylamine and methanol were added to the reactor, and NaOH aqueous solution was added as an acid-binding agent to cause it to separate into layers. The reactor was cooled and evacuated to a constant static pressure. Thionyl fluoride was introduced into the layer containing dimethylamine under stirring, and the reactor was cooled to maintain the reaction temperature at T = 30°C. The pressure was set at P = 20 kPa, and the reaction time was t = 30 minutes. At the end of the reaction, the high-pressure reactor was vented, opened, filtered, and the contents were separated using a funnel. The lower layer was subjected to vacuum distillation to obtain pure FSO2NMe2. The yield of FSO2NMe2 and the utilization rate of dimethylamine were measured.

[0065] Final products: Only the final products of the first phase, H2O and NaF insoluble substances, with no other byproducts.

[0066] Technical benefits: In Example 3, the utilization rate of dimethylamine was increased to 95%, eliminating the need for recycling and reuse of intermediate products, making the reaction simpler and saving processing time.

[0067] Example 4: Heterogeneous mixing homogenization method, adding KOH as an inorganic base as an acid-binding agent in the initial reaction.

[0068] Reactants: SO2F2 and Me2NH,

[0069] Reaction process: SO2F2 + Me2NH + NaOH = FSO2NMe2 + NaF

[0070] As shown in Table 1, dimethylamine and methanol were added to the reactor, and NaOH aqueous solution was added as an acid-binding agent to cause stratification. The reactor was cooled and evacuated to a constant static pressure. Thionyl fluoride was introduced into the reactor containing dimethylamine under stirring, and the reactor was cooled to maintain the reaction temperature at T = 30°C. The pressure was set at P = 20 kPa, and the reaction time was t = 30 minutes. At the end of the reaction, the high-pressure reactor was vented, opened, filtered, and the contents were separated using a funnel. The lower layer was subjected to vacuum distillation to obtain pure FSO2NMe2. The yield of FSO2NMe2 and the utilization rate of dimethylamine were measured.

[0071] Final products: Only the final products of the first phase, H2O and KF insoluble substances, with no other byproducts.

[0072] Technical benefits: In Example 4, the utilization rate of dimethylamine was increased to 95%, eliminating the need for recycling and reuse of intermediate products, making the reaction simpler and saving processing time.

[0073] Example 5: Uniform mixing method, adding Na2CO3 as an inorganic base as an acid-binding agent in the initial reaction.

[0074] Reactants: SO2F2 and Me2NH,

[0075] Reaction process: 2SO₂F₂ + 2Me₂NH₃ + Na₂CO₃ = 2FSO₂NMe₂ + 2NaF + H₂O + CO₂

[0076] As shown in Table 1, dimethylamine was added to the reactor, and Na2CO3 aqueous solution was added as an acid-binding agent to cause it to separate into layers. The reactor was cooled and evacuated to a constant static pressure. Thionyl fluoride was introduced into the mixture under stirring, and the reactor was cooled to maintain the reaction temperature at T = 30°C. The pressure was set at P = 20 kPa, and the reaction time was t = 30 minutes. At the end of the reaction, the high-pressure reactor was vented, opened, filtered, and the contents were separated using a funnel. The lower layer was subjected to vacuum distillation to obtain pure FSO2NMe2. The yield of FSO2NMe2 and the utilization rate of dimethylamine were measured.

[0077] Final products: Only the final products of the first phase, H2O and NaF insoluble substances, with no other byproducts.

[0078] Technical benefits: In Example 5, the utilization rate of dimethylamine was increased to 91%, eliminating the need for recycling and reuse of intermediate products, making the reaction simpler and saving processing time.

[0079] Example 6: Uniform mixing method, adding NaHCO3 as an inorganic base as an acid-binding agent in the initial reaction.

[0080] Reactants: SO2F2 and Me2NH,

[0081] Reaction process: SO2F2 + Me2NH + NaHCO3 = FSO2NMe2 + NaF + H2O + CO2

[0082] As shown in Table 1, dimethylamine was added to the reactor, and NaHCO3 aqueous solution was added as an acid-binding agent to cause stratification. The reactor was cooled and evacuated to a constant static pressure. Thionyl fluoride was introduced into the mixture under stirring, and the reactor was cooled to maintain a reaction temperature of T = 30°C. The pressure was set to P = 20 kPa, and the reaction time was t = 30 minutes. At the end of the reaction, the high-pressure reactor was vented, opened, filtered, and the contents were separated using a funnel. The lower layer was subjected to vacuum distillation to obtain pure FSO2NMe2. The yield of FSO2NMe2 and the utilization rate of dimethylamine were measured.

[0083] Final products: Only the final products of the first phase, H2O and NaF insoluble substances, with no other byproducts.

[0084] Technical benefits: In Example 6, the utilization rate of dimethylamine was increased to 92%, eliminating the need for recycling and reuse of intermediate products, making the reaction simpler and saving processing time.

[0085] Comparative Example 1: No inorganic or organic catalysts added

[0086] Reactants: SO2F2 and Me2NH,

[0087] Reaction process: SO₂F₂ + 2Me₂NH₃ = FSO₂NMe₂ + Me₂NH₂F

[0088] As shown in Table 1, dimethylamine was added to the reactor, cooled, and evacuated to a constant static pressure. Thionyl fluoride was introduced into the mixture under stirring, and the mixture was cooled to maintain a reaction temperature of T = 30°C. The pressure was set to P = 20 kPa, and the reaction time was t = 30 minutes. At the end of the reaction, the high-pressure reactor was vented, opened, filtered, and the contents were separated using a funnel. The lower layer was subjected to vacuum distillation to obtain pure FSO2NMe2. The yield of FSO2NMe2 and the utilization rate of dimethylamine were measured.

[0089] Final products: Only the first phase final products and the second phase products (which need to be recycled).

[0090] Technical benefits: In Comparative Example 1, the utilization rate of dimethylamine was 46%, eliminating the need for recycling and reuse of intermediate products, making the reaction simpler and saving on processing steps.

[0091] Comparative Example 2: Adding an organic base

[0092] Reactants: SO2F2 and Me2NH,

[0093] Reaction process: SO2F2 + Me2NH + Et3N = FSO2NMe2 + Et3NHF

[0094] As shown in Table 1, dimethylamine and an organic base (triethylamine) were added to the reactor as an acid-binding agent. The reactor was cooled and evacuated to a constant static pressure. Thionyl fluoride was introduced into the mixture under stirring, and the reactor was cooled to maintain a reaction temperature of T = 30°C. The pressure was set to P = 20 kPa, and the reaction time was t = 30 minutes. At the end of the reaction, the high-pressure reactor was vented, opened, and water was added. The contents were then separated using a funnel. The lower layer was subjected to vacuum distillation to obtain pure FSO2NMe2. The yield of FSO2NMe2 and the utilization rate of dimethylamine were measured.

[0095] Reaction process: SO2F2 is introduced into Me2NH, and organic alkali solution is added to allow the fluorine-containing reactants to react completely, generating a second phase, which needs to be recovered and reused.

[0096] Final products: The final products of the first phase and the products of the second phase must be recycled separately.

[0097] Technical benefits: The utilization rate of dimethylamine is 46.5%, but the reaction process is relatively complex and contains organic products, requiring the recovery of the first and second phase products.

[0098] Comparative Example 3: An inorganic base was added to the base of Comparative Example 2.

[0099] Reactants: SO2F2 and Me2NH,

[0100] Reaction process: SO2F2 + Me2NH + Et3N = FSO2NMe2 + Et3NHF

[0101] As shown in Table 1, dimethylamine and an organic base (triethylamine) were added to the reactor as an acid-binding agent. The reactor was cooled and evacuated to a constant static pressure. Thionyl fluoride was introduced into the mixture under stirring and cooled to maintain the reaction temperature at T = 30°C. The pressure was set at P = 20 kPa and the reaction time was t = 30 minutes. At the end of the reaction, the high-pressure reactor was vented, opened, filtered, and the contents were separated using a funnel.

[0102] Then, NaOH aqueous solution was added to the upper layer obtained by separation to release Me2NH. Then, sulfuryl fluoride was continued to be passed into the mixture, and the mixture was cooled to maintain the reaction temperature at T = 30°C, the pressure was set at P = 20 kPa, and the reaction time was t = 30 minutes. At the end of the reaction, the high-pressure reactor was vented, opened, filtered, and the contents were separated by a funnel. The lower layers obtained from the two reactions were combined and subjected to vacuum distillation to obtain pure FSO2NMe2. The yield of FSO2NMe2 and the utilization rate of dimethylamine were measured.

[0103] Reaction process: SO2F2 is introduced into Me2NH. After the reaction, the utilization rate of F is 50%. An inorganic base is added to the second phase generated by the reaction for recycling.

[0104] Final products: The final products of the first phase and the products of the second phase must be recycled separately.

[0105] Technical benefits: The reaction efficiency of dimethylamine is increased to 88%, but the reaction process is relatively complex and contains organic products, requiring the recovery of the first and second phase products.

[0106] Table 1:

[0107]

[0108] Although the invention has been described in conjunction with specific embodiments, those skilled in the art will understand that many modifications and variations can be made to the invention. Therefore, it is to be appreciated that the claims are intended to cover all such modifications and variations that fall within the true concept and scope of the invention.

Claims

1. A method of preparing N-(fluorosulfonyl)dimethylamine, the method comprising: In the presence of an inorganic base, thioyl fluoride is brought into contact with dimethylamine to react and form N-(fluorosulfonyl)dimethylamine.

2. The method according to claim 1, wherein, The method includes: (1) The inorganic base is mixed with dimethylamine to form a homogeneous mixture comprising the inorganic base and dimethylamine; and (2) Thionyl fluoride is introduced into the mixture to form N-(fluorosulfonyl)dimethylamine.

3. The method according to claim 2, wherein, Step (2) includes: introducing thioyl fluoride into the mixture at a rate sufficient to control the temperature of the reaction between -30°C and 110°C; and / or Under stirring and / or aeration, thioyl fluoride is introduced into the mixture, and the reaction forms N-(fluorosulfonyl)dimethylamine.

4. The method according to claim 1, wherein, The method includes: (a) An inorganic base is added to dimethylamine to form a heterogeneous mixture comprising a first inorganic phase and a second organic phase, wherein the first inorganic phase comprises an inorganic base and the second organic phase comprises dimethylamine; and (b) Introducing thioyl fluoride into the second organic phase, reacting to form a product containing N-(fluorosulfonyl)dimethylamine.

5. The method according to claim 4, wherein, Step (b) includes: introducing thioyl fluoride into a second organic phase at a location adjacent to the first organic phase, where a local reaction occurs to form N-(fluorosulfonyl)dimethylamine; and / or Thionyl fluoride is introduced into the second organic phase at a rate sufficient to control the temperature of the reaction between -30°C and 110°C.

6. The method according to claim 4, wherein, The method further includes: (c) The product formed in step (b) of stirring promotes the continued reaction.

7. The method according to claim 1, 2 or 4, wherein, The inorganic base is selected from at least one of LiOH, KOH, NaOH, Na2CO3, and NaHCO3.

8. The method according to claim 1, 2 or 4, wherein, The inorganic base, dimethylamine, and thioyl fluoride react in a molar ratio of 0.1:1:0.1 to 2:1:

2.

9. The method according to claim 1, 2 or 4, wherein, The dimethylamine is selected from pure dimethylamine or a polar solution of dimethylamine.

10. The method according to claim 1, 2 or 4, wherein, The reaction uses a solvent as a carrier, which is selected from water, methanol, ethanol, and any combination thereof.

11. The method according to claim 1, 2 or 4, wherein, The reaction is carried out in a batch process or a continuous process.

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