Preparation method of fluorosulfonyl cyanamide salt
By using sulfonyl fluoride to react with cyanamide and triethylamine in an aqueous solvent, combined with extraction and alkaline washing steps, the problems of low purity and yield of fluorosulfonyl cyanamide salt in traditional methods are solved, and efficient and environmentally friendly preparation of fluorosulfonyl cyanamide salt is achieved.
Patent Information
- Application Number
- CN202510815130.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-06-18
- Publication Date
- 2025-09-19
AI Technical Summary
Traditional synthesis methods cannot ensure the selectivity of the reaction when preparing fluorosulfonyl cyanamide salts, resulting in low product purity, product yield and reaction efficiency.
The method uses low-cost sulfonyl fluoride as a raw material, reacts with cyanamide and acid-binding agent triethylamine in solvent water to generate fluorosulfonyl cyanamide triethylamine salt, and improves the reaction selectivity through extraction, water washing, alkali washing and other steps to avoid the polymerization side reaction of cyanamide, and further reacts with an organic base to generate fluorosulfonyl cyanamide metal salt.
The selectivity and yield of the reaction are improved, the polymerization side reaction of cyanamide is avoided, and the process is environmentally friendly.
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Abstract
Description
Technical Field
[0001] The present application relates to the technical field of reaction processes, and in particular to a method for preparing fluorosulfonyl cyanamide salt. Background Art
[0002] Sulfonyl cyanamide salts are a new class of compounds with anionic structures, which have important potential applications in new energy and other fields. Among them, fluorosulfonyl cyanamide salts, as a key component of sulfonyl cyanamide salts, have attracted much attention. However, due to the presence of fluorosulfonyl groups in their structures, traditional synthesis strategies cannot ensure reaction selectivity during the synthesis process, resulting in low product purity, product yield, and reaction efficiency. Summary of the Invention
[0003] Based on this, it is necessary to provide a method for preparing fluorosulfonyl cyanamide salt to improve the reaction efficiency, product purity and yield of fluorosulfonyl cyanamide salt.
[0004] The present application provides a method for preparing fluorosulfonyl cyanamide salt, comprising the following steps:
[0005] S1, cyanamide, triethylamine and water are mixed to prepare a mixed solution;
[0006] S2. Sulfonyl fluoride is introduced into the mixed solution until it reaches saturation, and the mixture is extracted, concentrated and dried to prepare triethylamine salt of fluorosulfonyl cyanamide.
[0007] In some embodiments, in S2, the molar ratio of cyanamide to triethylamine and sulfonyl fluoride is 1:(1-2):(0.46-0.95).
[0008] In some embodiments, in S2, the molar ratio of cyanamide to triethylamine and sulfonyl fluoride is 1:(1-1.5):(0.46-0.7).
[0009] In some embodiments, in S2, the extraction process comprises:
[0010] The mixed solution into which sulfonyl fluoride is introduced until saturated is mixed with the extractant, and after the two phases are separated, the organic phase is washed with water and then with alkali.
[0011] In some embodiments, the extractant is selected from one or more of dichloromethane and dichloroethane.
[0012] In some embodiments, the water washing and alkali washing treatments are performed multiple times.
[0013] In some embodiments, the alkaline washing treatment is performed using a saturated sodium bicarbonate solution.
[0014] In some embodiments, the method for preparing fluorosulfonyl cyanamide salt further comprises the following steps:
[0015] S3, reacting fluorosulfonyl cyanamide triethylamine salt with the first solvent and an organic base at a preset temperature, filtering and drying, to prepare fluorosulfonyl cyanamide metal salt;
[0016] Wherein, the first solvent is selected from one or more of methyl tert-butyl ether, diethyl ether, and tetrahydrofuran;
[0017] The organic base is selected from one or more of sodium tert-butoxide, potassium tert-butoxide and lithium tert-butoxide;
[0018] The preset temperature is below 15℃.
[0019] In the present application, the prepared fluorosulfonyl cyanamide triethylamine salt is reacted with an organic base to further generate a fluorosulfonyl cyanamide metal salt.
[0020] In some embodiments, in S3, the molar ratio of fluorosulfonyl cyanamide triethylamine salt to the organic base is 1:(1-1.5).
[0021] In some embodiments, S3 includes: mixing fluorosulfonyl cyanamide triethylamine salt with methyl tert-butyl ether to prepare a mixed solution; and adding an organic base to the mixed solution in batches.
[0022] In some embodiments, in S3, after filtering and drying, the following steps are further included:
[0023] The product obtained by filtration and drying is mixed with ethyl acetate and activated carbon to prepare a mixed solution; the mixed solution is filtered to prepare a filtrate; and the filtrate is concentrated to dryness.
[0024] In some embodiments, in S3, after filtering and drying, the following steps are further included:
[0025] The product obtained by filtration and drying is mixed with methyl tert-butyl ether, slurried, filtered, and rinsed with methyl tert-butyl ether.
[0026] Compared with the existing technology, this application has the following beneficial effects:
[0027] The present invention uses low-cost sulfonyl fluoride as a raw material and reacts it with cyanamide in a solvent water and an acid-binding agent triethylamine to generate fluorosulfonyl cyanamide triethylamine salt. In the preparation process, water is used as a solvent and triethylamine is used as an acid-binding agent, which improves the selectivity of the reaction while avoiding the self-polymerization side reaction of cyanamide, thereby improving the reaction yield and being environmentally friendly. BRIEF DESCRIPTION OF THE DRAWINGS
[0028] In order to more clearly illustrate the technical solutions in the embodiments of the present application or related technologies, the following briefly introduces the drawings required for use in the embodiments or related technical descriptions. Obviously, the drawings described below are only some embodiments of the present application. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying any creative work.
[0029] Figure 1 The present invention is a flow chart of a method for preparing fluorosulfonyl cyanamide salt in some embodiments of the present application.
[0030] Figure 2 The present invention is a flow chart of a method for preparing fluorosulfonyl cyanamide salt in other embodiments of the present application. DETAILED DESCRIPTION
[0031] To facilitate understanding of the present application, a more comprehensive description of the present application will be provided below with reference to the accompanying drawings. The accompanying drawings illustrate preferred embodiments of the present application. However, the present application may be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a more thorough and comprehensive understanding of the disclosure of the present application.
[0032] Therefore, it is intended that this application covers such modifications and variations that fall within the scope of the appended claims and their equivalents. Other objects, features, and aspects of the present application are disclosed in or are apparent from the following detailed description. Those skilled in the art will appreciate that this discussion is merely a description of exemplary embodiments and is not intended to limit the broader aspects of the present application.
[0033] In this application, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.
[0034] In this application, when referring to numerical ranges, unless otherwise specified, the numerical ranges are considered continuous and include the minimum and maximum values of the range, as well as every value between such minimum and maximum values. Further, when a range refers to an integer, every integer between the minimum and maximum values of the range is included. In addition, when multiple ranges are provided to describe a feature or characteristic, the ranges can be combined. In other words, unless otherwise specified, all ranges disclosed herein should be understood to include any and all subranges subsumed therein.
[0035] In this article, when referring to the units of a data range, if the unit is followed only by the right endpoint, it means that the units of the left and right endpoints are the same.
[0036] Unless otherwise specified, all embodiments and optional embodiments of the present application can be combined with each other to form a new technical solution.
[0037] Unless otherwise specified, all technical features and optional technical features of this application can be combined with each other to form a new technical solution.
[0038] Unless otherwise specified, all steps of the present application may be performed sequentially or randomly, preferably sequentially. For example, a statement that a method includes steps (a) and (b) indicates that the method may include steps (a) and (b) performed sequentially, or may include steps (b) and (a) performed sequentially. For example, a statement that a method may also include step (c) indicates that step (c) may be added to the method in any order, for example, the method may include steps (a), (b), and (c), or may include steps (a), (c), and (b), or may include steps (c), (a), and (b), etc.
[0039] Unless otherwise specified, the terms "include" and "comprising" used in this application may be open-ended or closed-ended. For example, "include" and "comprising" may indicate that other components not listed may also be included or that only the listed components are included.
[0040] Unless otherwise specified, the term "or" is used in this application to be inclusive. For example, the phrase "A or B" means "A, B, or both A and B." More specifically, the condition "A or B" is satisfied if any of the following conditions are met: A is true (or exists) and B is false (or does not exist); A is false (or does not exist) and B is true (or exists); or both A and B are true (or exist).
[0041] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art to which this application pertains. The terms used herein in the specification of this application are for the purpose of describing specific embodiments only and are not intended to limit this application.
[0042] Due to the presence of fluorosulfonyl groups in the structure of fluorosulfonyl cyanamide salts, the selectivity of the reaction cannot be ensured during the synthesis process using traditional synthesis methods, resulting in low product purity, product yield and reaction efficiency.
[0043] Based on the above technical defects of the traditional synthesis method, the present application provides a preparation method of fluorosulfonyl cyanamide salt.
[0044] It should be noted that the fluorosulfonyl cyanamide salt in the present application may be fluorosulfonyl cyanamide triethylamine salt or fluorosulfonyl cyanamide metal salt.
[0045] like Figure 1 As shown, the preparation method of fluorosulfonyl cyanamide salt comprises the following steps:
[0046] S1, cyanamide, triethylamine and water are mixed to prepare a mixed solution;
[0047] S2. Sulfonyl fluoride is introduced into the mixed solution until it reaches saturation, and the mixture is extracted, concentrated and dried to prepare triethylamine salt of fluorosulfonyl cyanamide.
[0048] In the present application, the chemical formula of cyanamide is CH2N2, and the structural formula is shown in the following formula (I).
[0049] .
[0050] In this application, the chemical formula of triethylamine is C6H 15 N, the structural formula is shown in the following formula (II).
[0051] .
[0052] In the present application, the chemical formula of sulfonyl fluoride is SO2F2, and the structural formula is shown in the following formula (III).
[0053] .
[0054] In this application, the chemical formula of triethylamine salt of fluorosulfonyl cyanamide is C7H 16 FN3O2S, the structural formula is shown in the following formula (IV).
[0055] .
[0056] It is understood that the raw materials cyanamide, triethylamine and sulfonyl fluoride used in this application can be purchased directly from merchants or synthesized in a laboratory.
[0057] The term "saturated state" in this application means that under specific temperature and pressure conditions, the rate at which gas molecules enter the solution and the rate at which they escape from the solution per unit time reach a dynamic equilibrium, at which point the concentration of the gas dissolved in the solution reaches its maximum value under these conditions and no longer changes with time.
[0058] The present invention uses low-cost sulfonyl fluoride as a raw material and reacts it with cyanamide in a water solvent and an acid-binding agent, triethylamine, to generate fluorosulfonyl cyanamide triethylamine salt. In the preparation process, water is used as a solvent and triethylamine is used as an acid-binding agent, which improves the selectivity of the reaction while avoiding the self-polymerization side reaction of cyanamide, thereby improving the reaction yield and being more environmentally friendly.
[0059] In some embodiments, the above step S1 specifically includes the following steps: dissolving cyanamide in solvent water, adding triethylamine, and stirring at room temperature to prepare a mixed solution.
[0060] It is understood that, in the present application, there is no particular limitation on the time of stirring at room temperature, and it can be adjusted according to the actual reaction conditions, as long as cyanamide and triethylamine can be uniformly mixed in water.
[0061] In some embodiments, "room temperature" in this application refers to a temperature range of 10°C to 30°C, including but not limited to 10°C, 12°C, 15°C, 17°C, 20°C, 22°C, 25°C, 27°C, and 30°C.
[0062] It should be noted that, in the specific examples and comparative examples of the present application, when room temperature is mentioned without any special explanation, the "room temperature" at this time refers to 25°C.
[0063] In some embodiments, the concentration of cyanamide in water is 28% to 50%, including but not limited to 28%, 30%, 35%, 38%, 40%, 43%, 45%, 48%, and 50%.
[0064] When the concentration of cyanamide in water is too high, self-polymerization side reaction will occur, and when the concentration of cyanamide in water is too low, the reaction rate will slow down.
[0065] It is understandable that the water mentioned in this application can be deionized water, distilled water or ultrapure water, and is not particularly limited here.
[0066] In some embodiments, in S2, the molar ratio of cyanamide to triethylamine and sulfonyl fluoride is 1:(1-2):(0.46-0.95), including but not limited to 1:1:0.46, 1:1.5:0.7, 1:1.5:0.95, and 1:2:0.95.
[0067] Furthermore, the molar ratio of cyanamide to triethylamine and sulfonyl fluoride is 1:(1-1.5):(0.46-0.7). For example, the molar ratio may be 1:1:0.46 or 1:1.5:0.7.
[0068] In some embodiments, in step S2 above, the extraction process specifically includes the following steps:
[0069] The mixed solution into which sulfonyl fluoride is introduced until saturated is mixed with the extractant, and after the two phases are separated, the organic phase is sequentially washed with water and then with alkali.
[0070] In the present application, water washing is used to remove residual water-soluble impurities in the organic phase.
[0071] In the present application, alkaline washing is used to remove acidic substances remaining in the reaction.
[0072] In some embodiments, the extractant is selected from one or more of dichloromethane (DCM) and dichloroethane (DCE).
[0073] In some embodiments, the water washing and alkali washing treatments are performed multiple times.
[0074] It is understood that the number of water washing and alkali washing treatments includes but is not limited to 2 times, 3 times, and 4 times. Among them, water washing can be performed multiple times, and then alkali washing can be performed multiple times; or the water washing and alkali washing processes can be cyclically operated multiple times.
[0075] It can also be understood that in the present application, the specific method of alkaline washing treatment is not particularly limited. Without violating the overall inventive concept of the present application, any known treatment method capable of alkaline washing can be applied to the present application. The following is only an example of using saturated sodium bicarbonate solution for alkaline washing treatment.
[0076] In some embodiments, in the above step S2, the extracted solution is concentrated and dried using anhydrous sodium sulfate.
[0077] When using the traditional sodium cyanamide synthesis strategy to prepare fluorosulfonylcyanamide metal salts, the presence of the fluorosulfonyl group in the structure prevents the reaction from ensuring selectivity, resulting in low product purity, yield, and reaction efficiency. Furthermore, the traditional process uses non-aqueous solvents, which can cause severe environmental pollution.
[0078] Therefore, the present invention reacts the prepared triethylamine salt of fluorosulfonyl cyanamide with an organic base to further generate a metal salt of fluorosulfonyl cyanamide, thereby avoiding the above-mentioned defects in the traditional process of sodium cyanamide synthesis strategy.
[0079] like Figure 2 As shown, in some embodiments, the preparation method of fluorosulfonyl cyanamide salt may further include the following steps:
[0080] S3, reacting fluorosulfonyl cyanamide triethylamine salt with a first solvent and an organic base at a preset temperature, filtering and drying, to prepare fluorosulfonyl cyanamide salt.
[0081] In some embodiments, the first solvent is selected from one or more of methyl tert-butyl ether (MTBE), diethyl ether, and tetrahydrofuran (THF).
[0082] In some embodiments, the organic base is selected from one or more of sodium tert-butoxide (C4H9NaO), potassium tert-butoxide (C4H9OK), and lithium tert-butoxide (C4H9LiO).
[0083] In some embodiments, the preset temperature is below 15°C.
[0084] It is understandable that the preset temperature is below 15°C, including but not limited to 15°C, 14°C, 13°C, 12°C, 11°C, 10°C, 9°C, and 8°C.
[0085] In some embodiments, in the above step S3, the molar ratio of fluorosulfonyl cyanamide triethylamine salt to the organic base is 1:(1-1.5), including but not limited to 1:1, 1:2, 1:3, 1:4, and 1:5.
[0086] In some embodiments, the above step S3 specifically includes the following steps: mixing fluorosulfonyl cyanamide triethylamine salt with methyl tert-butyl ether to prepare a mixed solution; and adding an organic base to the mixed solution in batches.
[0087] It is understandable that the number of times the organic base is added and the amount added each time can be adjusted according to actual needs, as long as the reaction temperature can be maintained at a certain level.
[0088] In some embodiments, an ice bath or a cold water bath is used for stirring during the process of adding the organic base to the mixed solution in batches.
[0089] Since a violent exotherm will occur after adding an organic base to the mixed liquid, if a large amount of organic base is added at one time, the sequential accumulation of heat may cause the reaction temperature to get out of control, the side reactions to intensify, and even cause boiling. Therefore, in this application, the organic base is added in batches, and an ice bath or a cold water bath is used for stirring at the same time, so that the reaction heat can be released step by step and the heat can be quickly dissipated, so as to maintain the reaction temperature below 15°C.
[0090] In some embodiments, in the above step S3, after filtering and drying, the following steps are further included:
[0091] The product obtained by filtration and drying is mixed with ethyl acetate and activated carbon to prepare a mixed solution; the mixed solution is filtered to prepare a filtrate; and the filtrate is concentrated to dryness.
[0092] This application uses ethyl acetate to separate the target product from the impurities in the solid mixture and allow it to enter the liquid phase. At the same time, activated carbon is added to adsorb pigments and small molecular impurities in the liquid phase to prepare a high-purity target product.
[0093] In some embodiments, diatomaceous earth may also be added during the step of adding activated carbon for filtration.
[0094] It is understandable that diatomaceous earth, as an inert filter aid, can be used to prevent activated carbon from clogging filter paper, thereby speeding up filtration and improving production efficiency.
[0095] In some embodiments, in the above step S3, after filtering and drying, the following steps are further included:
[0096] The product obtained by filtration and drying is mixed with methyl tert-butyl ether, slurried, filtered, and rinsed with methyl tert-butyl ether.
[0097] The present application uses beating and eluting steps to further remove residual impurities and improve the purity of the target product.
[0098] The present invention first uses low-cost sulfonyl fluoride as a raw material and reacts it with cyanamide in a solvent of water and an acid-binding agent of triethylamine to generate fluorosulfonyl cyanamide triethylamine salt. On this basis, the prepared fluorosulfonyl cyanamide triethylamine salt is reacted with an organic base to further synthesize fluorosulfonyl cyanamide sodium salt, fluorosulfonyl cyanamide potassium salt, etc. In the entire preparation process, water is used as a solvent and triethylamine is used as an acid-binding agent, which improves the selectivity of the reaction while avoiding the self-polymerization side reaction of cyanamide, thereby improving the reaction efficiency and reaction yield, and is very environmentally friendly.
[0099] Furthermore, the present application also provides the following specific embodiments and comparative examples to further illustrate the specific implementation of the present application and its advantages.
[0100] Example 1
[0101] This example prepared triethylamine salt of fluorosulfonyl cyanamide.
[0102] The raw materials were weighed according to the molar ratio of cyanamide, triethylamine and sulfonyl fluoride being 1:1.5:0.7.
[0103] 84 g of cyanamide was dissolved in 300 mL of aqueous solvent, and 303 g of triethylamine was added to prepare a mixed solution. The reaction was stirred at room temperature.
[0104] 150 g of sulfonyl fluoride was added to the mixed solution until saturated, and the mixture was stirred at 25 ° C for 12 h. 300 mL of dichloromethane was added and mixed, and the two phases were separated to prepare an organic phase; the organic phase was washed with 300 mL of water, saturated sodium bicarbonate solution, and 300 mL of water in sequence, and then concentrated and dried with anhydrous sodium sulfate to prepare triethylamine salt of fluorosulfonyl cyanamide (224 g, product yield: 67%). 19 F NMR (400MHz, CDCl3): δ 56.39 (s, F).
[0105] The reaction process diagram is shown below:
[0106] .
[0107] Example 2
[0108] This embodiment prepares sodium fluorosulfonyl cyanamide, potassium fluorosulfonyl cyanamide and lithium fluorosulfonyl cyanamide.
[0109] (1) Sodium fluorosulfonyl cyanamide
[0110] The raw materials were weighed according to a molar ratio of fluorosulfonyl cyanamide triethylamine salt cyanamide and sodium tert-butoxide of 1:1.08.
[0111] 313 g of triethylamine salt of fluorosulfonyl cyanamide was added to 1 L of methyl tert-butyl ether, stirred in an ice bath, and 130 g of sodium tert-butoxide was added in several portions. The mixture was stirred in an ice bath for 1 hour, and then filtered and dried. 1 L of ethyl acetate and 10 g of activated carbon were added, and filtration was assisted by diatomaceous earth. The filter cake was concentrated and dried to obtain a filter cake. The filter cake was added to 0.5 L of methyl tert-butyl ether, pulped and filtered, rinsed with 0.1 L of methyl tert-butyl ether, and dried under reduced pressure to obtain sodium fluorosulfonyl cyanamide (165 g, product yield: 73%). 19 F NMR (400MHz, d6-acetone): δ55.1(s, F).
[0112] The reaction process diagram is shown below:
[0113] .
[0114] (2) Potassium fluorosulfonyl cyanamide
[0115] The raw materials were weighed according to a molar ratio of fluorosulfonyl cyanamide triethylamine salt cyanamide and potassium tert-butoxide of 1:1.21.
[0116] 22.5 g of triethylamine salt of fluorosulfonyl cyanamide was added to 100 mL of methyl tert-butyl ether, stirred in an ice bath, and 13.4 g of potassium tert-butoxide was added in several portions. After continuing to stir in an ice bath for 1 hour, the mixture was filtered and dried; the dried product was added to 0.1 L of methyl tert-butyl ether, pulped and filtered, rinsed with 0.1 L of methyl tert-butyl ether, and dried under reduced pressure to obtain potassium fluorosulfonyl cyanamide (16 g, product yield: 99%). 19 F NMR (400MHz, d6-DMSO): δ 57.1(s, F).
[0117] The reaction process diagram is shown below:
[0118] .
[0119] (3) Lithium fluorosulfonyl cyanamide
[0120] The raw materials were weighed so that the molar ratio of fluorosulfonyl cyanamide triethylamine salt cyanamide and lithium tert-butoxide was 1:1.
[0121] 11.2 g of triethylamine salt of fluorosulfonyl cyanamide was added to 100 mL of methyl tert-butyl ether and stirred in an ice bath. 4 g of lithium tert-butoxide was added in several portions. After continuing to stir in an ice bath for 1 h, the mixture was filtered and the filtrate was concentrated and dried to obtain lithium fluorosulfonyl cyanamide (3.9 g, product yield: 60%). 19 F NMR (400MHz, d6-acetone): δ55.8(s, F).
[0122] The reaction process diagram is shown below:
[0123] .
[0124] Example 3
[0125] The preparation method of this embodiment is basically the same as that of Example 1, except that the molar ratio of cyanamide, triethylamine and sulfonyl fluoride is about 1:1.04:0.46. The specific reaction process is as follows:
[0126] The raw materials were weighed according to the molar ratio of cyanamide, triethylamine and sulfonyl fluoride being 1:1.04:0.46.
[0127] 42 g of cyanamide was dissolved in 100 mL of solvent water, and 105 g of triethylamine was added to prepare a mixed solution. The reaction was carried out under stirring at 25°C.
[0128] 47 g of sulfonyl fluoride was added to the mixed solution, stirred at 25°C for 12 h, 100 mL of dichloromethane was added and mixed, and the two phases were separated to prepare an organic phase; the organic phase was washed with 100 mL of water, 100 mL of saturated sodium bicarbonate solution, and 100 mL of water in sequence, and then concentrated and dried with anhydrous sodium sulfate to prepare triethylamine salt of fluorosulfonyl cyanamide (71 g, product yield: 68%).
[0129] Example 4
[0130] The preparation method of this embodiment is basically the same as that of Example 1, except that the molar ratio of cyanamide, triethylamine and sulfonyl fluoride is 1:1.5:0.7. The specific reaction process is as follows:
[0131] 42 g of cyanamide was dissolved in 100 mL of solvent water, and 151 g of ethylamine was added to prepare a mixed solution. The reaction was carried out under stirring at 25°C.
[0132] 71 g of sulfonyl fluoride was added to the mixed solution, stirred at 25°C for 12 h, 100 mL of dichloromethane was added and mixed, and the two phases were separated to prepare an organic phase; the organic phase was washed with 100 mL of water, 100 mL of saturated sodium bicarbonate solution, and 100 mL of water in sequence, and then concentrated and dried with anhydrous sodium sulfate to prepare triethylamine salt of fluorosulfonyl cyanamide (107 g, product yield: 68%).
[0133] Comparative Example 1 This comparative example adopts the traditional sodium cyanamide synthesis process to prepare sodium fluorosulfonyl cyanamide.
[0134] To 50 mL of tetrahydrofuran, 20 g of sodium cyanamide was added to prepare a mixed solution; the mixed solution was cooled to about -30°C using dry ice ethanol.
[0135] 23 g of sulfonyl fluoride was added to the mixed solution, and the temperature was slowly raised to room temperature. The reaction was stopped immediately after reaching room temperature to obtain sodium fluorosulfonyl cyanamide (3.8 g, product yield: 17%).
[0136] By comparing Example 2 with Comparative Example 1, it can be seen that compared with the traditional sodium cyanamide synthesis process in Comparative Example 1, the product yield of sodium fluorosulfonyl cyanamide prepared by the preparation process provided in the present application is significantly higher.
[0137] The technical features of the above-mentioned embodiments can be combined arbitrarily. In order to make the description concise, not all possible combinations of the technical features in the above-mentioned embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.
[0138] The above-described embodiments merely represent several implementation methods of the present application. While the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the present invention. It should be noted that a person skilled in the art could make various modifications and improvements without departing from the spirit of the present application, all of which fall within the scope of protection of the present application. Therefore, the scope of protection of the present patent application shall be determined by the appended claims.
Claims
1. A method for preparing a fluorosulfonyl cyanamide salt, characterized in that: The following steps are involved: S1, cyanamide, triethylamine and water are mixed to prepare a mixed solution; S2. Sulfonyl fluoride is introduced into the mixed solution until it reaches saturation, and the mixed solution is extracted, concentrated and dried to prepare triethylamine salt of fluorosulfonyl cyanamide.
2. The method for preparing fluorosulfonyl cyanamide salt according to claim 1, wherein In the S2, the molar ratio of the cyanamide to triethylamine and the sulfonyl fluoride is 1:(1-2):(0.46-0.95).
3. The method for preparing fluorosulfonyl cyanamide salt according to claim 1, wherein: In said S2, the extraction process comprises: The mixed solution into which sulfonyl fluoride is introduced until saturated is mixed with the extractant, and after the two phases are separated, the organic phase is washed with water and then with alkali.
4. The method for preparing fluorosulfonyl cyanamide salt according to claim 3, wherein: The extractant is selected from one or more of dichloromethane and dichloroethane.
5. The method for preparing fluorosulfonyl cyanamide salt according to claim 3, wherein: The water washing and alkali washing treatments are performed multiple times.
6. The method for preparing fluorosulfonyl cyanamide salt according to claim 1, wherein: The following steps are also included: S3, reacting the triethylamine salt of fluorosulfonyl cyanamide with a first solvent and an organic base at a preset temperature, filtering and drying, to prepare a metal salt of fluorosulfonyl cyanamide; Wherein, the first solvent is selected from one or more of methyl tert-butyl ether, diethyl ether, and tetrahydrofuran; The organic base is selected from one or more of sodium tert-butoxide, potassium tert-butoxide and lithium tert-butoxide; The preset temperature is below 15°C.
7. The method for preparing fluorosulfonyl cyanamide salt according to claim 6, characterized in that: In the S3, the molar ratio of the triethylamine salt of fluorosulfonyl cyanamide to the organic base is 1:(1-1.5).
8. The method for preparing fluorosulfonyl cyanamide salt according to any one of claims 6 to 7, characterized in that: The step S3 comprises: mixing the triethylamine salt of fluorosulfonyl cyanamide with methyl tert-butyl ether to prepare a mixed solution; and adding the organic base to the mixed solution in batches.
9. The method for preparing fluorosulfonyl cyanamide salt according to any one of claims 6 to 7, characterized in that: In the S3, after the filtration and drying, the following steps are further included: The product obtained by filtration and drying is mixed with ethyl acetate and activated carbon to prepare a mixed solution; the mixed solution is filtered to prepare a filtrate; and the filtrate is concentrated to dryness.
10. The method for preparing fluorosulfonyl cyanamide salt according to any one of claims 6 to 7, characterized in that: In the S3, after the filtration and drying, the following steps are further included: The product obtained by filtration and drying is mixed with methyl tert-butyl ether, slurried, filtered, and rinsed with methyl tert-butyl ether.