Trifluoromethyl-containing sultone derivative as well as preparation method and application thereof
By introducing trifluoromethyl groups into alkylsulfonolide, a new type of trifluoromethyl-containing sulfonolide derivative was developed, which solved the existence of existing alkylsulfonolides in the electronics industry. Performance limitations problem, high-performance electrolyte additives are realized.
Patent Information
- Application Number
- CN202410052348.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-01-12
- Publication Date
- 2025-02-07
- Estimated Expiration
- 2044-01-12
AI Technical Summary
The molecular structure of the existing alkylsulfonolide has certain limitations in its application and is difficult to meet the demand for high-performance materials in the modern electronics industry.
By introducing trifluoromethyl groups into the molecular structure of alkylsulfonolide, a novel sulfonolide containing trifluoromethyl is developed, and a new type of sulfonolide containing trifluoromethyl is provided, including addition reaction, acidification treatment, Preparation method of ring-closing reaction and fluorination reaction.
This new sulfonolactone derivative has excellent performance in electrolyte additive application, and has a simple preparation method, easy raw materials, mild reaction conditions, and has broad application prospects.
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Figure CN119390678A_ABST
Abstract
Description
Technical Field
[0001] The invention relates to the technical field of synthetic methods of organic compounds and materials, and in particular to a trifluoromethyl-containing sultone derivative and a preparation method and application thereof. Background Art
[0002] Alkyl sultones are a class of fine organic chemicals with special structures. They can react with many compounds under mild conditions to undergo various organic transformation reactions and accurately provide sulfonic acid groups. These compounds are also widely used as pharmaceutical intermediates, brighteners, electroplating alloys, electrolyte additives, dyes, diionic surfactants and sulfonating agents. In particular, in recent years, various alkyl sultones have played an important role in the electroplating of metal printed circuit boards.
[0003] Fluorine-containing organic chemicals usually have some unusual or even very special physical and chemical properties due to the high electronegativity and small atomic radius of fluorine atoms. They have been widely used in many disciplines such as pharmaceutical chemistry and materials science. It is particularly worth noting that fluorine chemical products play a very important role in the electronics industry. For example, fluoride crystals are key components used in the manufacture of optical fiber communication systems and laser equipment, fluoropolymers are widely used to manufacture protective films for electronic components, and fluorides are also used to manufacture insulating layers and dielectrics in semiconductors and electronic devices.
[0004] Therefore, it is a very meaningful task to develop novel fluorinated alkyl sultone derivatives based on the molecular structure of existing alkyl sultones through special organic transformation reactions, which can provide new strategies and molecular basis for the sustainable development and application of alkyl sultone derivatives. Summary of the invention
[0005] In view of this, in view of the above-mentioned deficiencies in the prior art, the present invention provides a novel trifluoromethyl-containing sultone derivative and a preparation method and application thereof, so as to solve or at least partially solve the deficiencies in the prior art.
[0006] In a first aspect, the present invention provides a trifluoromethyl-containing sultone derivative, the chemical structural formula of the derivative is as follows:
[0007]
[0008] In a second aspect, the present invention further provides a method for preparing the trifluoromethyl-containing sultone derivative, comprising the following steps:
[0009] Propynol is subjected to an addition reaction with an alkali metal sulfite or an alkali metal bisulfite to obtain an intermediate 3-hydroxypropenyl sulfonate;
[0010] The intermediate 3-hydroxypropylene sulfonate is subjected to acidification treatment to obtain 3-hydroxypropylene sulfonic acid;
[0011] 3-Hydroxypropylene sulfonic acid undergoes a ring-closing reaction to obtain 1-propylene-1,3-sultone;
[0012] 1-Propene-1,3-sultone is subjected to fluorination reaction to obtain a sultone derivative containing a trifluoromethyl group.
[0013] Preferably, in the method for preparing the trifluoromethyl sultone derivative, the alkali metal sulfite comprises at least one of sodium sulfite and potassium sulfite;
[0014] The alkali metal bisulfite includes at least one of sodium bisulfite and potassium bisulfite.
[0015] Preferably, the method for preparing the trifluoromethyl sultone derivative comprises adding propargyl alcohol, alkali metal sulfite or alkali metal bisulfite to a first solvent, and performing an addition reaction at 25 to 80° C. to obtain an intermediate 3-hydroxypropenyl sulfonate;
[0016] The first solvent includes at least one of methanol, ethanol, tetrahydrofuran, acetonitrile, ethyl acetate, ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide and water.
[0017] Preferably, in the method for preparing the trifluoromethyl sultone derivative, the intermediate 3-hydroxypropylene sulfonate is acidified to a pH of 3 to 4 to obtain 3-hydroxypropylene sulfonic acid, wherein the acid used includes at least one of hydrochloric acid, sulfuric acid and nitric acid.
[0018] Preferably, the method for preparing the trifluoromethyl sultone derivative comprises adding 3-hydroxypropylene sulfonic acid to a second solvent and performing a ring-closing reaction at 25 to 80° C. under acidic conditions to obtain 1-propylene-1,3-sultone; or adding 3-hydroxypropylene sulfonic acid to a second solvent and performing a ring-closing reaction at 110 to 130° C. to obtain 1-propylene-1,3-sultone;
[0019] The second solvent includes at least one of methanol, ethanol, toluene, chlorobenzene, benzene, tetrahydrofuran, acetonitrile, ethyl acetate, ethyl ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, and water.
[0020] Preferably, in the method for preparing the trifluoromethyl sultone derivative, 1-propylene-1,3-sultone is added to a third solvent, and then an oxidizing agent and a fluorinating agent are added to carry out an addition reaction to obtain the trifluoromethyl-containing sultone derivative.
[0021] Preferably, in the method for preparing the trifluoromethyl sultone derivative, the oxidant comprises at least one of hydrogen peroxide and tert-butyl hydroperoxide;
[0022] The fluorinating agent includes at least one of sodium trifluoromethanesulfinate and potassium trifluoromethanesulfinate.
[0023] Preferably, in the method for preparing the trifluoromethyl sultone derivative, in the step of subjecting 1-propylene-1,3-sultone to fluorination reaction, the fluorination reaction temperature is 0 to 60°C.
[0024] In a third aspect, the present invention further provides a use of the trifluoromethyl-containing sultone derivative or the trifluoromethyl-containing sultone derivative prepared by the preparation method as an electrolyte additive.
[0025] Compared with the prior art, the trifluoromethyl-containing sultone derivatives and the preparation method thereof of the present invention have the following advantages:
[0026] Beneficial effects:
[0027] The trifluoromethyl-containing sultone derivative of the present invention has the chemical structural formula: The trifluoromethyl-containing sultone derivative of the present invention can be used as an electrolyte additive; the preparation method of the trifluoromethyl-containing sultone derivative of the present invention is simple and easy, the raw materials are cheap and easy to obtain, and the reaction conditions are mild. The trifluoromethyl-containing sultone derivative of the present invention is a functional material with broad application prospects and can be used as an electrolyte additive. BRIEF DESCRIPTION OF THE DRAWINGS
[0028] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the following briefly introduces the drawings required for use in the embodiments or the prior art descriptions. Obviously, the drawings described below are only some embodiments of the present invention, and for ordinary technicians in this field, other drawings can be obtained based on these drawings without creative work.
[0029] Figure 1 This is the nuclear magnetic resonance spectrum of 1-propylene-1,3-sultone prepared in Example 1 of the present invention;
[0030] Figure 2 This is the nuclear magnetic resonance spectrum of the trifluoromethyl-containing sultone derivative prepared in Example 1 of the present invention. DETAILED DESCRIPTION
[0031] The following will be combined with the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.
[0032] It should be noted that the order of description of the following embodiments is not intended to limit the preferred order of the embodiments. In addition, in the description of the present application, the term "including" means "including but not limited to". Various embodiments of the present invention may be in the form of a range; it should be understood that the description in the form of a range is only for convenience and brevity and should not be understood as a rigid limitation on the scope of the present invention; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values within the range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the numbered ranges, such as 1, 2, 3, 4, 5 and 6, which apply regardless of the range. In addition, whenever a numerical range is indicated in this article, it is meant to include any cited numbers (fractions or integers) within the indicated range.
[0033] The present application provides a trifluoromethyl-containing sultone derivative, the chemical structure of which is shown below:
[0034]
[0035] The trifluoromethyl-containing sultone derivative of the present invention can be used as an electrolyte additive.
[0036] Based on the same inventive concept, the present invention also provides a method for preparing the above-mentioned trifluoromethyl-containing sultone derivative, comprising the following steps:
[0037] S1, subjecting propargyl alcohol to an addition reaction with an alkali metal sulfite or an alkali metal bisulfite to obtain an intermediate 3-hydroxypropenyl sulfonate;
[0038] S2, subjecting the intermediate 3-hydroxypropylene sulfonate to acid treatment to obtain 3-hydroxypropylene sulfonic acid;
[0039] S3 and 3-hydroxypropylene sulfonic acid undergo a ring-closing reaction to obtain 1-propylene-1,3-sultone;
[0040] S4, 1-propylene-1,3-sultone is subjected to fluorination reaction to obtain a sultone derivative containing a trifluoromethyl group.
[0041] Specifically, the reaction flow of the method for preparing the trifluoromethyl-containing sultone derivative of the present invention is as follows:
[0042]
[0043] Propynol (i.e., the above structural formula 1) undergoes addition reaction with various alkali metal sulfites or bisulfites to obtain an intermediate 3-hydroxypropylene sulfonate, and then the intermediate is subjected to acidification treatment to obtain 3-hydroxypropylene sulfonic acid (the above structural formula 2); 3-hydroxypropylene sulfonic acid undergoes a ring-closing reaction in an appropriate solvent, and after separation and purification, a key intermediate 1-propylene-1,3-sultone (the above structural formula 3) is obtained; 1-propylene-1,3-sultone undergoes a fluorination reaction under appropriate reaction conditions to obtain the target compound 4.
[0044] In some embodiments, the alkali metal sulfite includes at least one of sodium sulfite and potassium sulfite;
[0045] The alkali metal bisulfite includes at least one of sodium bisulfite and potassium bisulfite.
[0046] In some embodiments, step S1 specifically comprises: adding an alkali metal sulfite or an alkali metal bisulfite to a first solvent, stirring to dissolve, heating to 30-40° C., then slowly dropping propargyl alcohol under vigorous stirring, controlling the temperature at 35-45° C. to react for 3-6 hours after the dropwise addition, concentrating the reaction solution under reduced pressure until solids precipitate, cooling, adding a certain amount of anhydrous ethanol, and standing to obtain an intermediate 3-hydroxypropylene sulfonate solution;
[0047] The first solvent includes at least one of methanol, ethanol, tetrahydrofuran, acetonitrile, ethyl acetate, ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide and water.
[0048] In some embodiments, step S2 specifically includes: filtering the above-mentioned soaking liquid (i.e., the intermediate 3-hydroxypropylene sulfonate solution), concentrating the filtrate under reduced pressure to one-third of the volume, cooling, and acidifying the intermediate 3-hydroxypropylene sulfonate with an appropriate acid to a pH of 3 to 4 to obtain 3-hydroxypropylene sulfonic acid, wherein the acid used includes at least one of hydrochloric acid, sulfuric acid, and nitric acid.
[0049] In some embodiments, step S3 specifically comprises: adding 3-hydroxypropene sulfonic acid to the second solvent, and carrying out a ring-closing reaction at 25 to 80° C. under acidic catalytic conditions, and after the reaction is completed, performing reduced pressure distillation to obtain 1-propylene-1,3-sultone; or adding 3-hydroxypropene sulfonic acid to the second solvent, and carrying out a ring-closing reaction at 110 to 130° C. to obtain 1-propylene-1,3-sultone;
[0050] The second solvent includes at least one of methanol, ethanol, toluene, chlorobenzene, benzene, tetrahydrofuran, acetonitrile, ethyl acetate, ethyl ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, and water.
[0051] In some embodiments, step S4 specifically includes: adding 1-propylene-1,3-sultone to a third solvent, then adding a fluorinating agent while stirring, controlling the temperature at 0-10°C in an ice-water bath, and slowly dropping an oxidant; after the dropwise addition, removing the ice-water bath, and then slowly heating to 30-50°C for reaction, after the reaction is completed, conventional water treatment, drying, and concentration are performed to obtain a light yellow oily substance, which is a crude product of a trifluoromethyl-containing sultone derivative, and the oily substance obtained by reduced-pressure distillation with an oil pump is the target compound.
[0052] In some embodiments, the oxidant comprises at least one of hydrogen peroxide and tert-butyl hydroperoxide;
[0053] In some embodiments, the fluorinating agent includes at least one of sodium trifluoromethanesulfinate and potassium trifluoromethanesulfinate.
[0054] In some embodiments, in the step of fluorinating 1-propylene-1,3-sultone, the fluorination reaction temperature is 0 to 60°C.
[0055] Based on the same inventive concept, the present invention also provides a use of the above-mentioned trifluoromethyl-containing sultone derivative or the trifluoromethyl-containing sultone derivative prepared by the above-mentioned preparation method as an electrolyte additive.
[0056] The following further illustrates the preparation method of the trifluoromethyl-containing sultone derivative of the present application with specific examples. This section further illustrates the content of the present invention in conjunction with specific examples, but should not be construed as limiting the present invention. Unless otherwise specified, the technical means used in the examples are conventional means known to those skilled in the art. Unless otherwise specified, the reagents, methods and equipment used in the present invention are conventional reagents, methods and equipment in the art.
[0057] Example 1
[0058] The present application example provides a method for preparing a trifluoromethyl-containing sultone derivative, and the reaction formula is:
[0059]
[0060] Specifically, the preparation method comprises the following steps:
[0061] S1. Dissolve sodium bisulfite in a certain amount of water, stir to dissolve, heat to 35°C, then slowly drop propargyl alcohol under vigorous stirring, control the temperature at 40°C for 5 hours after the dropwise addition, concentrate the reaction solution under reduced pressure until solid precipitates, cool, add appropriate anhydrous ethanol, and let stand; filter the above soaking solution, concentrate the filtrate under reduced pressure to one-third of the volume, cool, and acidify the intermediate 3-hydroxypropylene sulfonate with an appropriate acid to a pH of 3.5 to obtain 3-hydroxypropylene sulfonic acid; then, add 3-hydroxypropylene sulfonic acid to a second solvent (specifically methanol), and carry out a ring-closing reaction at 60°C under hydrochloric acid catalysis. After the reaction is completed, 1-propylene-1,3-sultone is obtained by reduced pressure distillation as a white crystalline powder;
[0062] S2. Weigh 0.12 g (1 mmol) of the intermediate 1-propylene-1,3-sultone and dissolve it in 10 mL of dichloromethane. Then, add 0.312 g (2 mmol) of an aqueous solution of sodium trifluoromethanesulfinate (4 mL) and 0.39 g (3 mmol) of a tert-butyl hydroperoxide solution (mass concentration 70%) dropwise under continuous stirring and an ice bath. The addition is completed in about half an hour. The mixture is slowly heated to 32 degrees and kept warm for reaction overnight. The crude product is then treated with conventional water to obtain an oily product, which is a trifluoromethyl-containing sultone derivative of the target compound obtained by reduced pressure distillation with an oil pump.
[0063] Example 2
[0064] The present invention provides a method for preparing a trifluoromethyl-containing sultone derivative, comprising the following steps:
[0065] S1. Dissolve sodium bisulfite in a certain amount of water, stir to dissolve, heat to 35°C, then slowly drop propargyl alcohol under vigorous stirring, control the temperature at 40°C for 5 hours after the dropwise addition, concentrate the reaction solution under reduced pressure until solid precipitates, cool, add appropriate anhydrous ethanol, and let stand; filter the above soaking solution, concentrate the filtrate under reduced pressure to one-third of the volume, cool, and acidify the intermediate 3-hydroxypropylene sulfonate with an appropriate acid to a pH of 3.5 to obtain 3-hydroxypropylene sulfonic acid; then, add 3-hydroxypropylene sulfonic acid to a second solvent (specifically methanol), and carry out a ring-closing reaction at 60°C under hydrochloric acid catalysis. After the reaction is completed, 1-propylene-1,3-sultone is obtained by reduced pressure distillation as a white crystalline powder;
[0066] S2. Weigh 0.24 g (2 mmol) of the intermediate 1-propylene-1,3-sultone and dissolve it in 15 mL of ethyl acetate. Then, add 0.936 g (6 mmol) of an aqueous solution (8 mL) of sodium trifluoromethanesulfinate under continuous stirring. Then, slowly dropwise add 1.13 g (10 mmol) of an aqueous hydrogen peroxide solution (mass concentration is 30%) in an ice bath. The addition takes about 20 minutes. Slowly heat to 40 degrees and keep the reaction overnight. Then, perform conventional water treatment to obtain a crude product, and then separate and purify by column chromatography to obtain the target compound, a trifluoromethyl-containing sultone derivative.
[0067] Example 3
[0068] The present invention provides a method for preparing a trifluoromethyl-containing sultone derivative, comprising the following steps:
[0069] S1. Dissolve sodium bisulfite in a certain amount of water, stir to dissolve, heat to 35°C, then slowly drop propargyl alcohol under vigorous stirring, control the temperature at 40°C for 5 hours after the dropwise addition, concentrate the reaction solution under reduced pressure until solid precipitates, cool, add appropriate anhydrous ethanol, and let stand; filter the above soaking solution, concentrate the filtrate under reduced pressure to one-third of the volume, cool, and acidify the intermediate 3-hydroxypropylene sulfonate with an appropriate acid to a pH of 3.5 to obtain 3-hydroxypropylene sulfonic acid; then, add 3-hydroxypropylene sulfonic acid to a second solvent (specifically methanol), and carry out a ring-closing reaction at 60°C under hydrochloric acid catalysis. After the reaction is completed, 1-propylene-1,3-sultone is obtained by reduced pressure distillation as a white crystalline powder;
[0070] S2. Weigh 0.12 g (1 mmol) of the intermediate 1-propylene-1,3-sultone 3 and suspend it in 10 mL of water. Then, add 0.468 g (3 mmol) of an aqueous solution of sodium trifluoromethanesulfinate (4 mL) under continuous stirring. Then, slowly dropwise add 0.64 g (5 mmol) of tert-butyl hydroperoxide solution (mass concentration is 70%) in an ice bath. The addition takes about 20 minutes. Slowly heat to 40 degrees and keep the reaction overnight. Then, perform conventional water treatment to obtain a crude product. The crude product is then decolorized by activated carbon. The filtrate is concentrated to obtain the target compound, a trifluoromethyl-containing sultone derivative.
[0071] Example 4
[0072] The present invention provides a method for preparing a trifluoromethyl-containing sultone derivative, comprising the following steps:
[0073] S1. Dissolve sodium bisulfite in a certain amount of water, stir to dissolve, heat to 35°C, then slowly drop propargyl alcohol under vigorous stirring, control the temperature at 40°C for 5 hours after the dropwise addition, concentrate the reaction solution under reduced pressure until solid precipitates, cool, add appropriate anhydrous ethanol, and let stand; filter the above soaking solution, concentrate the filtrate under reduced pressure to one-third of the volume, cool, and acidify the intermediate 3-hydroxypropylene sulfonate with an appropriate acid to a pH of 3.5 to obtain 3-hydroxypropylene sulfonic acid; then, add 3-hydroxypropylene sulfonic acid to a second solvent (specifically methanol), and carry out a ring-closing reaction at 60°C under hydrochloric acid catalysis. After the reaction is completed, 1-propylene-1,3-sultone is obtained by reduced pressure distillation as a white crystalline powder;
[0074] S2. Weigh 0.60 g (5 mmol) of the intermediate 1-propylene-1,3-sultone 3 and suspend it in 40 mL of dichloromethane. Then, add 1.56 g (10 mmol) of an aqueous solution of sodium trifluoromethanesulfinate (15 mL) under continuous stirring. Then, slowly dropwise add 1.92 g (15 mmol) of tert-butyl hydroperoxide solution (mass concentration 70%) in an ice bath. The addition is completed in about 30 minutes. Slowly heat to 40 degrees and keep the reaction overnight. Then stand and separate the liquids. The aqueous phase is extracted with dichloromethane, and the organic phases are combined. The organic phases are washed with water, washed with saturated brine, dried, and concentrated to obtain a crude product. The crude product is then distilled under reduced pressure to obtain the target compound, a trifluoromethyl-containing sultone derivative.
[0075] Example 5
[0076] The present invention provides a method for preparing a trifluoromethyl-containing sultone derivative, comprising the following steps:
[0077] S1. Dissolve sodium bisulfite in a certain amount of water, stir to dissolve, heat to 35°C, then slowly drop propargyl alcohol under vigorous stirring, control the temperature at 40°C for 5 hours after the dropwise addition, concentrate the reaction solution under reduced pressure until solid precipitates, cool, add appropriate anhydrous ethanol, and let stand; filter the above soaking solution, concentrate the filtrate under reduced pressure to one-third of the volume, cool, and acidify the intermediate 3-hydroxypropylene sulfonate with an appropriate acid to a pH of 3.5 to obtain 3-hydroxypropylene sulfonic acid; then, add 3-hydroxypropylene sulfonic acid to a second solvent (specifically methanol), and carry out a ring-closing reaction at 60°C under hydrochloric acid catalysis. After the reaction is completed, 1-propylene-1,3-sultone is obtained by reduced pressure distillation as a white crystalline powder;
[0078] S2. Weigh 0.12 g (1 mmol) of the intermediate 1-propylene-1,3-sultone 3 and dissolve it in 10 mL of dichloromethane. Then, add 0.516 g (3 mmol) of an aqueous solution of potassium trifluoromethanesulfinate (4 mL) under continuous stirring and an ice bath. Subsequently, slowly dropwise add 0.39 g (3 mmol) of a tert-butyl hydroperoxide solution (mass concentration of 70%). During the dropping process, the temperature of the system is controlled not to exceed 45 degrees. After the dropping is completed, keep the temperature at 40 degrees to react overnight. Subsequently, after conventional water treatment, drying and concentration, a light yellow oily substance is obtained as a crude product. The oily substance is obtained by vacuum distillation with an oil pump, which is the target compound, a trifluoromethyl-containing sultone derivative.
[0079] Figure 1 is the nuclear magnetic resonance spectrum of 1-propylene-1,3-sultone prepared in Example 1; specifically, its spectrum data is: 1 H NMR (600MHz, Chloroform-d) δ7.00 (d, J = 6.7 Hz, 1H), 6.81 (d, J = 6.7 Hz, 1H), 5.12 (d, J = 0.6 Hz, 2H).
[0080] Figure 2 This is the nuclear magnetic resonance spectrum of the trifluoromethyl-containing sultone derivative of the target compound prepared in Example 1; its spectrum data are: 1 H NMR(600MHz,Chloroform-d)δ4.57(dd,J=10.2,8.0Hz,1H),4.47(dd,J=10.2,5.8Hz ,1H),3.74–3.63(m,1H),3.58(dd,J=13.7,9.6Hz,1H),3.32(dd,J=13.7,7.4Hz,1H).
[0081] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.
Claims
1. A trifluoromethyl-containing sultone derivative, characterized in that: The chemical structural formula of the derivative is shown below:
2. A method for preparing a trifluoromethyl-containing sultone derivative according to claim 1, characterized in that: The following steps are involved: Propynol is subjected to an addition reaction with an alkali metal sulfite or an alkali metal bisulfite to obtain an intermediate 3-hydroxypropenyl sulfonate; The intermediate 3-hydroxypropylene sulfonate is subjected to acidification treatment to obtain 3-hydroxypropylene sulfonic acid; 3-Hydroxypropylene sulfonic acid undergoes a ring-closing reaction to obtain 1-propylene-1,3-sultone; 1-Propene-1,3-sultone is subjected to fluorination reaction to obtain a sultone derivative containing a trifluoromethyl group.
3. The method for preparing a trifluoromethyl sultone derivative according to claim 2, characterized in that: The alkali metal sulfite includes at least one of sodium sulfite and potassium sulfite; The alkali metal bisulfite includes at least one of sodium bisulfite and potassium bisulfite.
4. The method for preparing a trifluoromethyl sultone derivative according to claim 2, characterized in that: Adding propargyl alcohol, alkali metal sulfite or alkali metal bisulfite to the first solvent, and performing an addition reaction at 25 to 80° C. to obtain an intermediate 3-hydroxypropenyl sulfonate; The first solvent includes at least one of methanol, ethanol, tetrahydrofuran, acetonitrile, ethyl acetate, ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide and water.
5. The method for preparing a trifluoromethyl sultone derivative according to claim 2, characterized in that: The intermediate 3-hydroxypropylene sulfonate is subjected to acidification treatment to a pH of 3 to 4 to obtain 3-hydroxypropylene sulfonic acid, wherein the acid used includes at least one of hydrochloric acid, sulfuric acid and nitric acid.
6. The method for preparing a trifluoromethyl sultone derivative according to claim 2, characterized in that: 3-hydroxypropene sulfonic acid is added to the second solvent, and a ring-closing reaction is carried out at 25 to 80° C. under acidic conditions to obtain 1-propene-1,3-sultone; or 3-hydroxypropene sulfonic acid is added to the second solvent, and a ring-closing reaction is carried out at 110 to 130° C. to obtain 1-propene-1,3-sultone; The second solvent includes at least one of methanol, ethanol, toluene, chlorobenzene, benzene, tetrahydrofuran, acetonitrile, ethyl acetate, ethyl ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, and water.
7. The method for preparing a trifluoromethyl sultone derivative according to claim 2, characterized in that: 1-propylene-1,3-sultone is added to the third solvent, and then an oxidizing agent and a fluorinating agent are added to carry out an addition reaction to obtain a trifluoromethyl-containing sultone derivative.
8. The method for preparing a trifluoromethyl sultone derivative according to claim 7, characterized in that: The oxidant includes at least one of hydrogen peroxide and tert-butyl hydroperoxide; The fluorinating agent includes at least one of sodium trifluoromethanesulfinate and potassium trifluoromethanesulfinate.
9. The method for preparing a trifluoromethyl sultone derivative according to claim 7, characterized in that: In the step of subjecting 1-propylene-1,3-sultone to fluorination reaction, the fluorination reaction temperature is 0 to 60°C.
10. Use of the trifluoromethyl-containing sultone derivative according to claim 1 or the trifluoromethyl-containing sultone derivative prepared by the preparation method according to any one of claims 2 to 9 as an electrolyte additive.
Citation Information
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