A trifluoromethyl-containing sultone derivative, and a preparation method and application thereof

By preparing a method containing trifluoromethyl sultone derivatives, the problem of lack of innovation in the molecular structure of alkyl sultones is solved, and the preparation of functional materials is realized, especially the application as electrolyte additives.

CN119390678BActive Publication Date: 2025-10-17HUBEI BIOPESTICIDE ENG RES CENT +1
View PDF 2 Cites 0 Cited by

Patent Information

Application Number
CN202410052348.9
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-01-12
Publication Date
2025-10-17
Estimated Expiration
2044-01-12

AI Technical Summary

Technical Problem

The existing alkyl sulfone molecular structure lacks innovation and cannot meet the electronics industry's demand for functional materials.

Method used

The intermediate 3-hydroxypropenyl sulfonate is generated by reacting propargyl alcohol with alkali metal sulfite or alkali metal bisulfite. After acidification, the intermediate 3-hydroxypropenyl sulfonate is subjected to a ring-closure reaction to obtain 1-propylene-1,3-sultone. The intermediate 1-propene-1,3-sultone is then subjected to a fluorination reaction to introduce a trifluoromethyl group to prepare a novel trifluoromethyl-containing sultone derivative.

Benefits of technology

The invention provides a simple and easy preparation method with cheap and readily available raw materials. The prepared trifluoromethane sultone derivative can be used as an electrolyte additive and has broad application prospects.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN119390678B_ABST
    Figure CN119390678B_ABST
Patent Text Reader

Abstract

The present application relates to the technical fields of organic compound synthesis method, and particularly relates to a trifluoromethyl-containing sultone derivative and a preparation method and application thereof.The preparation method of the trifluoromethyl-containing sultone derivative of the present application comprises the following steps: (1) sulfonation reaction: addition reaction of propargyl alcohol and alkali metal sulfite or alkali metal bisulfite to obtain an intermediate 3-hydroxy propenyl sulfonate; (2) cyclization reaction: acidification treatment of the intermediate 3-hydroxy propenyl sulfonate to obtain 3-hydroxy propenyl sulfonic acid, and then ring closure reaction to obtain 1-propen-1, 3-sultone; (3) fluorination reaction: reaction of 1-propen-1, 3-sultone with a suitable fluorination reagent to obtain the trifluoromethyl-containing sultone derivative.The preparation method of the compound is simple and easy to operate, the raw materials are cheap and easy to obtain, the reaction conditions are mild, and the compound is a functional material with wide application prospect and can be applied as an electrolyte additive.
Need to check novelty before this filing date? Find Prior Art

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of synthesis method of organic compounds and materials, and particularly relates to a trifluoromethyl-containing sultone derivative and a preparation method and application thereof. BACKGROUND

[0002] Alkyl sultone is a kind of fine organic chemical with special structure, which can carry out various organic conversion reactions with many compounds under relatively mild conditions and accurately provide sulfonic acid groups. Such compounds are widely used as drug intermediates, brighteners, electroplating alloys, electrolyte additives, dyes, zwitterionic surfactants and sulfonating agents, etc. In particular, in recent years, various alkyl sultones have played an important role in metal printed circuit board electroplating.

[0003] Fluorine-containing organic chemicals usually have some unusual and even very special physical and chemical properties due to the high electronegativity and small atomic radius of fluorine atoms, and they have been widely used in many subject fields such as pharmaceutical chemistry and material science. It is particularly worth pointing out that fluorinated products play a very important role in the electronic industry, such as fluoride crystals are key components for manufacturing optical fiber communication systems and laser equipment, fluoropolymers are widely used for manufacturing protective films of electronic components, and fluorides are also used for manufacturing insulation layers and dielectric layers in semiconductors and electronic devices.

[0004] Therefore, it is a very meaningful work to develop novel fluorine-containing alkyl sultone derivatives with new structures through special organic conversion reactions based on the molecular structure of existing alkyl sultones, which can provide new strategies and molecular basis for the sustainable development and application of alkyl sultone derivative products. SUMMARY

[0005] Therefore, in view of the above-mentioned deficiencies in the prior art, the present application provides a novel trifluoromethyl-containing sultone derivative with a new structure and a preparation method and application thereof, so as to solve or at least partially solve the defects existing in the prior art.

[0006] In a first aspect, the present application provides a trifluoromethyl-containing sultone derivative, and the chemical structure formula of the derivative is as follows:

[0007]

[0008] In a second aspect, the present application further provides a preparation method of the trifluoromethyl-containing sultone derivative, comprising the following steps:

[0009] The addition reaction of propargyl alcohol and alkali metal sulfite or alkali metal bisulfite obtains an intermediate 3-hydroxy propenyl sulfonate;

[0010] The intermediate 3-hydroxy propenyl sulfonate is treated by acidification to obtain 3-hydroxy propenyl sulfonic acid;

[0011] The 3-hydroxy propenyl sulfonic acid is subjected to a ring closure reaction to obtain 1-propene-1,3-sulfolactone;

[0012] The 1-propene-1,3-sulfolactone is subjected to a fluorination reaction to obtain a trifluoromethyl-containing sulfolactone derivative.

[0013] Preferably, in the preparation method of the trifluoromethyl-containing sulfolactone derivative, the alkali metal sulfite includes 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, in the preparation method of the trifluoromethyl-containing sulfolactone derivative, the propargyl alcohol, the alkali metal sulfite or the alkali metal bisulfite is added to a first solvent to perform an addition reaction at 25-80°C to obtain the intermediate 3-hydroxy propenyl sulfonate;

[0016] The first solvent includes at least one of methanol, ethanol, tetrahydrofuran, acetonitrile, ethyl acetate, diethyl ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, and water.

[0017] Preferably, in the preparation method of the trifluoromethyl-containing sulfolactone derivative, the intermediate 3-hydroxy propenyl sulfonate is treated by acidification to a pH of 3-4 to obtain 3-hydroxy propenyl sulfonic acid, wherein the acid used includes at least one of hydrochloric acid, sulfuric acid, and nitric acid.

[0018] Preferably, in the preparation method of the trifluoromethyl-containing sulfolactone derivative, the 3-hydroxy propenyl sulfonic acid is added to a second solvent and subjected to a ring closure reaction under acidic conditions at 25-80°C to obtain 1-propene-1,3-sulfolactone, or the 3-hydroxy propenyl sulfonic acid is added to a second solvent and subjected to a ring closure reaction at 110-130°C to obtain 1-propene-1,3-sulfolactone.

[0019] The second solvent includes at least one of methanol, ethanol, toluene, chlorobenzene, benzene, tetrahydrofuran, acetonitrile, ethyl acetate, diethyl ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, and water.

[0020] Preferably, in the preparation method of the trifluoromethyl-containing sulfolactone derivative, the 1-propene-1,3-sulfolactone is added to a third solvent, and an oxidizing agent and a fluorinating agent are added to perform an addition reaction to obtain the trifluoromethyl-containing sulfolactone derivative.

[0021] Preferably, the preparation method of the trifluoromethyl-containing sulfolene derivative, the oxidant comprises at least one of hydrogen peroxide, tert-butyl hydroperoxide;

[0022] The fluorinating agent comprises at least one of sodium trifluoromethanesulfinic acid and potassium trifluoromethanesulfinic acid.

[0023] Preferably, in the step of fluorination of the 1-propenyl-1,3-sulfonic acid lactone in the preparation method of the trifluoromethyl-containing sulfolene derivative, the fluorination temperature is 0-60℃.

[0024] In a third aspect, the present application further provides an application of the trifluoromethyl-containing sulfolene derivative or the trifluoromethyl-containing sulfolene derivative prepared by the preparation method as an electrolyte additive.

[0025] The trifluoromethyl-containing sulfolene derivative and the preparation method thereof have the following advantages over the prior art

[0026] Advantages:

[0027] The trifluoromethyl-containing sulfolene derivative of the present application has the following chemical structure: The trifluoromethyl-containing sulfolene derivative of the present application can be used as an electrolyte additive; the preparation method of the trifluoromethyl-containing sulfolene derivative of the present application is simple and easy to operate, the raw materials are cheap and easy to obtain, and the reaction conditions are mild, so the trifluoromethyl-containing sulfolene derivative is a functional material with broad application prospect and can be used as an electrolyte additive. BRIEF DESCRIPTION OF DRAWINGS

[0028] In order to more clearly illustrate the technical solutions in the embodiments of the present application or the prior art, the following will briefly introduce the drawings needed to be used in the embodiments or the prior art description. Obviously, the drawings in the following description are only some embodiments of the present application, and for those skilled in the art, other drawings can also be obtained without creative labor on the basis of these drawings.

[0029] Figure 1 The nuclear magnetic resonance spectrum of the 1-propenyl-1,3-sulfonic acid lactone prepared in the embodiment 1 of the present application;

[0030] Figure 2 The nuclear magnetic resonance spectrum of the trifluoromethyl-containing sulfolene derivative prepared in the embodiment 1 of the present application. DETAILED DESCRIPTION

[0031] The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments of the present application. Based on the embodiments of the present application, all other embodiments obtained by those skilled in the art without creative work fall within the scope of the present application.

[0032] It should be noted that the sequence of the following embodiments is not limited as the preferred sequence of the embodiments. In addition, in the description of the present application, the term "comprising" means "including but not limited to". Various embodiments of the present application can exist in the form of a range; it should be understood that the description in the form of a range is only for the convenience and brevity, and should not be understood as a rigid limitation on the scope of the present application; therefore, it should be considered that the described range has been specifically disclosed all possible sub-ranges and single values in 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 in the range, such as 1, 2, 3, 4, 5 and 6, which applies to any range. In addition, whenever a numerical range is indicated in this document, it refers to any cited number (fraction or integer) within the indicated range.

[0033] The present application provides a trifluoromethyl-containing sultone derivative, and the chemical structural formula of the derivative is as follows:

[0034]

[0035] The present application provides a trifluoromethyl-containing sultone derivative, and the chemical structural formula of the derivative is as follows:

[0036] Based on the same inventive concept, the present application also provides a preparation method of the above-mentioned trifluoromethyl-containing sultone derivative, comprising the following steps:

[0037] S1, addition reaction of propargyl alcohol and alkali metal sulfite or alkali metal bisulfite to obtain an intermediate 3-hydroxy propenyl sulfonate;

[0038] S2, acidification treatment of the intermediate 3-hydroxy propenyl sulfonate to obtain 3-hydroxy propenyl sulfonic acid;

[0039] S3, ring closure reaction of 3-hydroxy propenyl sulfonic acid to obtain 1-propene-1,3-sultone;

[0040] S4, fluorination reaction of 1-propene-1,3-sultone to obtain a trifluoromethyl-containing sultone derivative.

[0041] Specifically, the reaction flow of the preparation method of the trifluoromethyl-containing sultone derivative of the present application is shown as follows:

[0042]

[0043] Propynol (i.e. the above structural formula 1) is subjected to addition reaction with various alkali metal sulfite or bisulfite to obtain an intermediate 3-hydroxy propenyl sulfonate, then the intermediate is subjected to acidification treatment to obtain 3-hydroxy propenyl sulfonic acid (the above structural formula 2); the 3-hydroxy propenyl sulfonic acid is subjected to ring-closing reaction in a suitable solvent, and after separation and purification, a key intermediate 1-propen-1,3-sultone (the above structural formula 3) is obtained; the 1-propen-1,3-sultone is subjected to fluorination reaction under suitable 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, the step S1 specifically includes: adding the alkali metal sulfite or alkali metal bisulfite into a first solvent, stirring and dissolving, heating to 30-40°C, then slowly adding propynol under vigorous stirring, controlling the temperature at 35-45°C after the dropping is completed, reacting for 3-6 hours, reducing and concentrating the reaction liquid to precipitate solids, cooling, adding a certain amount of anhydrous ethanol, and standing to obtain an intermediate 3-hydroxy propenyl sulfonate solution;

[0047] The first solvent includes at least one of methanol, ethanol, tetrahydrofuran, acetonitrile, ethyl acetate, diethyl ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, and water.

[0048] In some embodiments, the step S2 specifically includes: filtering the above immersion liquid (i.e. the intermediate 3-hydroxy propenyl sulfonate solution), reducing and concentrating the filtrate to one-third of the volume, cooling, and using a suitable acid to acidify the intermediate 3-hydroxy propenyl sulfonate to pH 3-4 to obtain 3-hydroxy propenyl sulfonic acid, wherein the acid used includes at least one of hydrochloric acid, sulfuric acid, and nitric acid.

[0049] In some embodiments, the step S3 specifically includes: adding the 3-hydroxy propenyl sulfonic acid into a second solvent, and performing ring-closing reaction under acidic catalysis conditions at 25-80°C to obtain 1-propen-1,3-sultone; or adding the 3-hydroxy propenyl sulfonic acid into a second solvent, and performing ring-closing reaction at 110-130°C to obtain 1-propen-1,3-sultone.

[0050] The second solvent includes at least one of methanol, ethanol, toluene, chlorobenzene, benzene, tetrahydrofuran, acetonitrile, ethyl acetate, diethyl ether, dichloromethane, trichloromethane, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, and water.

[0051] In some embodiments, step S4 specifically includes: adding 1-propene-1,3-sulfinic acid lactone into the third solvent, then adding a fluorinating agent under stirring, controlling the temperature of an ice water bath at 0-10℃, and slowly dropping an oxidizing agent; after dropping, removing the ice water bath, and then slowly increasing the temperature to 30-50℃ for reaction; after the reaction is completed, performing conventional water treatment, drying, and concentration to obtain a yellowish oil, which is a crude product of the sulfolactone derivative containing a trifluoromethyl group; and performing oil pump vacuum distillation to obtain an oil, which is the target compound.

[0052] In some embodiments, the oxidizing agent includes at least one of hydrogen peroxide and tert-butyl hydroperoxide.

[0053] In some embodiments, the fluorinating agent includes at least one of sodium trifluoromethanesulfinic acid and potassium trifluoromethanesulfinic acid.

[0054] In some embodiments, in the step of fluorination reaction of 1-propene-1,3-sulfinic acid lactone, the fluorination reaction temperature is 0-60℃.

[0055] Based on the same inventive concept, the present application also provides an application of the above-mentioned sulfolactone derivative containing a trifluoromethyl group or the sulfolactone derivative containing a trifluoromethyl group prepared by the above-mentioned preparation method as an electrolyte additive.

[0056] The preparation method of the sulfolactone derivative containing a trifluoromethyl group of the present application is further described below with specific embodiments. This part further describes the content of the present application in combination with specific embodiments, but should not be understood as a limitation of the present application. If not specifically stated, the technical means adopted in the embodiments are conventional means familiar to those skilled in the art. Unless specifically stated, the reagents, methods, and equipment adopted by the present application are conventional reagents, methods, and equipment in the art.

[0057] Embodiment 1

[0058] The present application embodiment provides a preparation method of a sulfolactone derivative containing a trifluoromethyl group, and the reaction formula thereof is as follows:

[0059]

[0060] Specifically, the preparation method includes the following steps:

[0061] S1, dissolve sodium bisulfite in a certain amount of water, stir and dissolve, heat to 35°C, then slowly add propargyl alcohol under vigorous stirring, control the temperature at 40°C after dropping, react for 5 hours, reduce pressure to concentrate the reaction liquid to have solid precipitate, cool, add appropriate anhydrous ethanol, stand; filter the above soaking liquid, reduce pressure to concentrate the filtrate to one third of the volume, cool, use appropriate acid to acidify the intermediate 3-hydroxyallyl sulfonate to pH 3.5 to obtain 3-hydroxyallyl sulfonic acid; then, add 3-hydroxyallyl sulfonic acid to a second solvent (specifically methanol) and perform ring closure reaction under hydrochloric acid catalysis at 60°C, after the reaction is completed, distill under reduced pressure to obtain 1-propen-1,3-sulfonyl lactone as a white crystalline powder;

[0062] S2, weigh 0.12g (1mmol) of intermediate 1-propen-1,3-sulfonyl lactone, dissolve it in 10mL dichloromethane, then add 0.312g (2mmol) of sodium trifluoromethanesulfinate aqueous solution (4mL) and 0.39g (3mmol) of tert-butyl hydroperoxide solution (mass concentration 70%) dropwise under continuous stirring and ice bath conditions, about half an hour to drop completely, slowly heat to 32 degrees and keep overnight, then perform conventional water treatment to obtain a crude product, and distill under reduced pressure by oil pump to obtain an oil as the target compound trifluoromethyl-containing sulfolactone derivative.

[0063] Example 2

[0064] The embodiment of the present application provides a preparation method of a trifluoromethyl-containing sulfolactone derivative, comprising the following steps:

[0065] S1, dissolve sodium bisulfite in a certain amount of water, stir and dissolve, heat to 35°C, then slowly add propargyl alcohol under vigorous stirring, control the temperature at 40°C after dropping, react for 5 hours, reduce pressure to concentrate the reaction liquid to have solid precipitate, cool, add appropriate anhydrous ethanol, stand; filter the above soaking liquid, reduce pressure to concentrate the filtrate to one third of the volume, cool, use appropriate acid to acidify the intermediate 3-hydroxyallyl sulfonate to pH 3.5 to obtain 3-hydroxyallyl sulfonic acid; then, add 3-hydroxyallyl sulfonic acid to a second solvent (specifically methanol) and perform ring closure reaction under hydrochloric acid catalysis at 60°C, after the reaction is completed, distill under reduced pressure to obtain 1-propen-1,3-sulfonyl lactone as a white crystalline powder;

[0066] S2, weigh 0.24g (2mmol) of intermediate 1-propen-1, 3-sulfinic acid lactone, dissolve it in 15mL of ethyl acetate, then add 0.936g (6mmol) of sodium trifluoromethanesulfinate aqueous solution (8mL) under continuous stirring, then slowly drop 1.13g (10mmol) of hydrogen peroxide aqueous solution (mass concentration of 30%) under ice bath condition, drop for about 20min, slowly heat to 40 degrees and keep overnight, then get the crude product through conventional water treatment, then get the target compound of trifluoromethyl-containing sulfolactone derivative through column chromatography separation and purification.

[0067] Example 3

[0068] The embodiment of the present application provides a preparation method of a trifluoromethyl-containing sulfolactone derivative, which comprises the following steps:

[0069] S1, dissolve sodium bisulfite in a certain amount of water, stir and dissolve, heat to 35℃, then slowly drop propargyl alcohol under vigorous stirring, control the temperature at 40℃ for 5 hours after dropping, reduce pressure and concentrate the reaction liquid to precipitate solids, cool, add appropriate anhydrous ethanol, and stand still; filter the above soaking liquid, reduce pressure and concentrate the filtrate to one third of the volume, cool, and acidify the intermediate 3-hydroxyallyl sulfonate to pH 3.5 with appropriate acid to obtain 3-hydroxyallyl sulfonic acid; then, add 3-hydroxyallyl sulfonic acid to a second solvent (specifically methanol) and perform ring closure reaction under hydrochloric acid catalysis at 60℃, after the reaction is completed, distill under reduced pressure to obtain 1-propen-1, 3-sulfinic acid lactone as a white crystalline powder;

[0070] S2, weigh 0.24g (2mmol) of intermediate 1-propen-1, 3-sulfinic acid lactone, dissolve it in 15mL of ethyl acetate, then add 0.936g (6mmol) of sodium trifluoromethanesulfinate aqueous solution (8mL) under continuous stirring, then slowly drop 1.13g (10mmol) of hydrogen peroxide aqueous solution (mass concentration of 30%) under ice bath condition, drop for about 20min, slowly heat to 40 degrees and keep overnight, then get the crude product through conventional water treatment, then get the target compound of trifluoromethyl-containing sulfolactone derivative through column chromatography separation and purification.

[0071] Example 4

[0072] The embodiment of the present application provides a preparation method of a trifluoromethyl-containing sulfolactone derivative, which comprises the following steps:

[0073] S1, dissolve sodium bisulfite in a certain amount of water, stir and dissolve, heat to 35°C, then slowly add propargyl alcohol under vigorous stirring, control the temperature at 40°C after dropping, react for 5 hours, reduce pressure to concentrate the reaction liquid to have solid precipitate, cool, add appropriate anhydrous ethanol, stand; filter the above soaking liquid, reduce pressure to concentrate the filtrate to one third of the volume, cool, use appropriate acid to acidify the intermediate 3-hydroxyallyl sulfonate to pH 3.5 to obtain 3-hydroxyallyl sulfonic acid; then, add 3-hydroxyallyl sulfonic acid to a second solvent (specifically methanol), and perform ring closure reaction under hydrochloric acid catalysis at 60°C, after the reaction is completed, distill under reduced pressure to obtain 1-propenyl-1,3-sulfolactone as a white crystalline powder;

[0074] S2, weigh 0.60 g (5 mmol) of intermediate 1-propenyl-1,3-sulfolactone 3, suspend it in 40 mL of dichloromethane, then add 1.56 g (10 mmol) of sodium trifluoromethanesulfinate aqueous solution (15 mL) under continuous stirring, then slowly add 1.92 g (15 mmol) of tert-butyl hydroperoxide solution (mass concentration 70%) dropwise under ice bath conditions, about 30 min for dropping, slowly heat to 40 degrees and keep overnight, then stand and separate, the aqueous phase is extracted with dichloromethane, the organic phases are combined, washed with water, saturated brine, dried, and concentrated to obtain a crude product, which is distilled under reduced pressure to obtain the target compound trifluoromethyl-containing sulfolactone derivative.

[0075] Example 5

[0076] The embodiment of the present application provides a preparation method of a trifluoromethyl-containing sulfolactone derivative, which comprises the following steps:

[0077] S1, dissolve sodium bisulfite in a certain amount of water, stir and dissolve, heat to 35°C, then slowly add propargyl alcohol under vigorous stirring, control the temperature at 40°C after dropping, react for 5 hours, reduce pressure to concentrate the reaction liquid to have solid precipitate, cool, add appropriate anhydrous ethanol, stand; filter the above soaking liquid, reduce pressure to concentrate the filtrate to one third of the volume, cool, use appropriate acid to acidify the intermediate 3-hydroxyallyl sulfonate to pH 3.5 to obtain 3-hydroxyallyl sulfonic acid; then, add 3-hydroxyallyl sulfonic acid to a second solvent (specifically methanol), and perform ring closure reaction under hydrochloric acid catalysis at 60°C, after the reaction is completed, distill under reduced pressure to obtain 1-propenyl-1,3-sulfolactone as a white crystalline powder;

[0078] S2, 0.12 g (1 mmol) of intermediate 1-propen-1, 3-sulfinic acid lactone 3 was weighed and dissolved in 10 mL of dichloromethane, then 0.516 g (3 mmol) of potassium trifluoromethanesulfinate aqueous solution (4 mL) was added under continuous stirring and ice bath conditions, followed by slowly dropping 0.39 g (3 mmol) of tert-butyl hydroperoxide solution (mass concentration of 70%), the dropping process controlled the system temperature not more than 45 degrees, after dropping, incubated at 40 degrees overnight, then treated with water, dried and concentrated to obtain a light yellow oil as a crude product, and then oil pump vacuum distillation to obtain an oil as the target compound trifluoromethyl-containing sulfolactone derivative.

[0079] Figure 1 The nuclear magnetic resonance spectrum of 1-propen-1, 3-sulfinic acid lactone prepared in Example 1; specifically, the spectral data thereof are as follows: 1 H NMR (600 MHz, Chloroform-d) δ 7.00 (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 The nuclear magnetic resonance spectrum of the target compound trifluoromethyl-containing sulfolactone derivative prepared in Example 1; the spectral data thereof are as follows: 1 H NMR (600 MHz, Chloroform-d) δ 4.57 (dd, J = 10.2, 8.0 Hz, 1H), 4.47 (dd, J = 10.2, 5.8 Hz, 1H), 3.74 - 3.63 (m, 1H), 3.58 (dd, J = 13.7, 9.6 Hz, 1H), 3.32 (dd, J = 13.7, 7.4 Hz, 1H).

[0081] The above only describes the preferred embodiments of the present application and is not intended to limit the present application. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application shall be included in the protection scope of the present application.

Claims

1. A method for preparing a trifluoromethyl-containing sultone derivative, characterized in that: The chemical structural formula of the trifluoromethyl-containing sultone derivative is as follows: The preparation method of the trifluoromethyl-containing sultone derivative comprises the following steps: Propargyl alcohol 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-Hydroxypropenesulfonic acid undergoes a ring-closure reaction to obtain 1-propene-1,3-sultone; 1-Propene-1,3-sultone is subjected to fluorination reaction to obtain a sultone derivative containing a trifluoromethyl group.

2. The method for preparing a trifluoromethyl sultone derivative according to claim 1, wherein: 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.

3. The method for preparing a trifluoromethyl sultone derivative according to claim 1, wherein: Propargyl alcohol, alkali metal sulfite or alkali metal bisulfite are added to the first solvent, and an addition reaction is carried out at 25 to 80° C. to obtain an intermediate 3-hydroxypropenyl sulfonate; The first solvent is selected from at least one of methanol, ethanol, tetrahydrofuran, acetonitrile, ethyl acetate, ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, and water.

4. The method for preparing a trifluoromethyl sultone derivative according to claim 1, wherein: The intermediate 3-hydroxypropene sulfonate is acidified to a pH of 3-4 to obtain 3-hydroxypropene sulfonic acid, wherein the acid used is selected from at least one of hydrochloric acid, sulfuric acid and nitric acid.

5. The method for preparing a trifluoromethyl sultone derivative according to claim 1, wherein: 3-hydroxypropenylsulfonic acid is added to a second solvent and subjected to a ring-closure reaction at 25 to 80° C. under acidic conditions to obtain 1-propene-1,3-sultone; or 3-hydroxypropenylsulfonic acid is added to a second solvent and subjected to a ring-closure reaction at 110 to 130° C. to obtain 1-propene-1,3-sultone; The second solvent is selected from at least one of methanol, ethanol, toluene, chlorobenzene, benzene, tetrahydrofuran, acetonitrile, ethyl acetate, ether, dichloromethane, chloroform, acetone, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, and water.

6. The method for preparing a trifluoromethyl sultone derivative according to claim 1, wherein: 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 a trifluoromethyl-containing sultone derivative.

7. The method for preparing a trifluoromethyl sultone derivative according to claim 6, wherein: The oxidant is selected from at least one of hydrogen peroxide and tert-butyl hydroperoxide; The fluorinating agent is selected from at least one of sodium trifluoromethanesulfinate and potassium trifluoromethanesulfinate.

8. The method for preparing a trifluoromethyl sultone derivative according to claim 6, wherein: In the step of fluorinating 1-propylene-1,3-sultone, the fluorination reaction temperature is 0 to 60°C.

Citation Information

Patent Citations

  • Electrolyte formulation for high voltage and wide temperature lithium-ion cells

    CN104662716A

  • Perfluoro alkylated derivative

    CN1528722A