Process for the preparation of organic sulfinate salts and their use

Abstract

The application relates to the technical field of organic synthesis, and discloses a preparation method of an organic sulfinate salt, characterized in that the method comprises the following steps: performing a nucleophilic addition reaction by contacting a compound shown in formula I or a compound shown in formula I' with a compound shown in formula II; and the nucleophilic reagent is at least one selected from nitrogen-substituted or unsubstituted dithionous acid and esters and salts thereof. The preparation method has high yield and excellent selectivity, and no organic sulfonic acid sodium salt is generated in by-products. The solubility difference between urea in the by-products and the product sulfinate sodium salt is large, subsequent recrystallization and purification operations are simple, the solvent consumption is small, and the separation efficiency is high.

Description

Technical Field

[0001] This invention relates to the field of organic synthesis technology, and specifically to a method for preparing an organic sulfinate and its application. Background Technology

[0002] Vinyl acetate-ethylene copolymer emulsion (VAE) is a copolymer of vinyl acetate (VAc) and ethylene (Ethylene) as monomers, produced by emulsion polymerization at temperatures of 30℃-150℃ and pressures of 3.0MPa-90.0MPa. Due to its excellent adhesion, flexibility, acid and alkali resistance, and film-forming properties, it is widely used in home decoration, construction and other industries.

[0003] The most widely used reducing agent in VAE emulsion polymerization is formaldehyde hyposulfite, but it produces formaldehyde during the reaction and remains in the final product, which does not meet the requirements of green environmental protection.

[0004] Brüggemann Chemicals in Germany has disclosed a sulfinic acid derivative, its preparation, and its applications. This compound can form a redox system with common oxidants for use in environmentally friendly VAE emulsion polymerization. As a reducing agent, this compound significantly lowers the activation energy of the reaction and increases the reaction rate. Furthermore, it contains no formaldehyde and does not produce formaldehyde during the reaction, making it suitable for the synthesis of low-VOC emulsions. However, the disclosed technique generates a certain amount of sulfonate byproducts along with the target product, sulfinic acid. These two substances are quite similar in properties and difficult to separate. Therefore, there is an urgent need to develop a new method for synthesizing organic sulfinates, which is of great significance to the development of VAE emulsion technology. Summary of the Invention

[0005] The purpose of this invention is to overcome the problems of low yield and purity of sulfinate compounds in the prior art, and to provide a method for preparing the compound and its application.

[0006] To achieve the above objectives, the present invention provides a method for preparing a compound, characterized in that the method comprises: contacting a compound of formula I or a compound of formula I' with a compound of formula II to carry out a nucleophilic addition reaction;

[0007]

[0008] Among them, R 1 Selected from H or C1-C6 alkyl, R 2 Selected from H, C1-C6 alkyl or M 1 ;

[0009] R 3 R 4 Each is independently H or C1-C6 alkyl;

[0010] When R 2 Selected from M 1 When the compound shown in Formula I has the same structure as the compound shown in Formula I',

[0011] M 1 Selected from NH4, monovalent metal cations or divalent metal cations, wherein the divalent metal cations are selected from divalent metal cations of Group IIA, IIB, IVA or VIII;

[0012] M is selected from divalent metal cations of groups IIA, IIB, IVA, or VIII.

[0013] The second aspect of the present invention provides the application of the method described in the first aspect of the present invention in improving the yield and purity of sulfinate compounds.

[0014] The preparation method described in this invention achieves high yield and excellent selectivity, with no organic sulfonate sodium salts among the byproducts. The byproduct urea and the product sodium sulfite salt have significantly different solubilities, simplifying subsequent recrystallization and purification operations, requiring less solvent, and resulting in high separation efficiency. Detailed Implementation

[0015] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0016] To achieve the above objectives, the present invention provides a method for preparing a compound, characterized in that the method comprises: contacting a compound of formula I or a compound of formula I' with a compound of formula II to carry out a nucleophilic addition reaction;

[0017]

[0018] Among them, R 1 Selected from H or C1-C6 alkyl, R 2 Selected from H, C1-C6 alkyl or M 1 ;

[0019] R 3 R 4 Each is independently H or C1-C6 alkyl;

[0020] M 1 Selected from NH4 or monovalent metal cations;

[0021] M is selected from divalent metal cations of groups IIA, IIB, IVA, or VIII.

[0022] In some embodiments of the present invention, preferably, R 1 Selected from H or C1-C5 alkyl groups.

[0023] In some embodiments of the present invention, preferably, R 2 Selected from H, C1-C3 alkyl or M 1 .

[0024] In some embodiments of the present invention, preferably, R 3 R 4 Each is independently H or C1-C3 alkyl.

[0025] In some embodiments of the present invention, preferably, M 1 Selected from monovalent metal cations.

[0026] In some embodiments of the present invention, preferably, R 1 Selected from H or C1-C3 alkyl groups.

[0027] In some embodiments of the present invention, preferably, R 2 Selected from H, methyl, ethyl or M 1 .

[0028] In some embodiments of the present invention, preferably, R 3 R 4 Each can be H, methyl, or ethyl independently.

[0029] In some embodiments of the present invention, preferably, M 1 Selected from sodium ions or potassium ions.

[0030] In some embodiments of the present invention, preferably, M is selected from magnesium ions, calcium ions, zinc ions or ferrous ions.

[0031] In some embodiments of the present invention, preferably, the nucleophilic reaction is carried out in the presence of a basic substance.

[0032] In some embodiments of the present invention, preferably, the alkaline substance is selected from at least one of hydroxides, carbonates, bicarbonates, basic carbonates and metal oxides, and more preferably from at least one of sodium hydroxide, sodium carbonate, sodium bicarbonate, potassium hydroxide, potassium carbonate, potassium bicarbonate, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium oxide, magnesium hydroxide, magnesium carbonate, magnesium bicarbonate, calcium oxide, calcium hydroxide, calcium carbonate, calcium bicarbonate, zinc oxide, zinc hydroxide, zinc carbonate, aluminum oxide, aluminum hydroxide and basic aluminum carbonate.

[0033] In some embodiments of the present invention, preferably, the alkaline substance is selected from at least one of sodium hydroxide, sodium carbonate, potassium hydroxide, and potassium carbonate.

[0034] In some embodiments of the present invention, preferably, the reaction is carried out in the presence of a solvent. The amount of solvent used may be 2-25 g relative to 1 g of the compound represented by Formula II.

[0035] In some embodiments of the present invention, preferably, the solvent is water.

[0036] In some embodiments of the present invention, preferably, the molar ratio of the alkaline substance to the compound represented by Formula I (or the compound represented by Formula I') is 1-4.5:1, which can be any value in the range of this molar ratio or a range between any two values, for example, any value or a range between any two values ​​of 1:1, 2:1, 3:1, 4:1 and 4.5:1.

[0037] In some embodiments of the present invention, preferably, the molar ratio of the compound represented by Formula II to the compound represented by Formula I (or the compound represented by Formula I') is 0.5-3.5:1, which can be any value in the range of this molar ratio or a range between any two values, for example, any value or a range between any two values ​​of 0.5:1, 1:1, 2:1, 3:1 and 3.5:1.

[0038] In some embodiments of the present invention, preferably, the temperature of the nucleophilic addition reaction is 0-90°C, which can be any value in this temperature range or a range between any two values. For example, it can be any value or a range between any two values ​​among 0°C, 10°C, 20°C, 30°C, 40°C, 50°C, 60°C, 70°C, 80°C, and 90°C.

[0039] In some embodiments of the present invention, preferably, the nucleophilic addition reaction time is 0.5-8h, which can be any value within this time range or a range between any two values. For example, it can be any value or a range between any two values ​​among 0.5h, 1h, 2h, 3h, 4h, 5h, 6h, 7h, and 8h.

[0040] In this invention, the reaction system obtained after the nucleophilic addition reaction can be separated and purified by cooling, filtration, recrystallization and drying to obtain the final product, the compound shown in Formula III.

[0041]

[0042] In some embodiments of the present invention, preferably, the cooling is to reduce the reaction system to 20-30°C.

[0043] In some embodiments of the present invention, preferably, the recrystallization temperature is -10 to 80°C.

[0044] In some embodiments of the present invention, preferably, the solvent used for recrystallization can be at least one of methanol, ethanol, acetonitrile, acetone and isopropanol.

[0045] In some embodiments of the present invention, preferably, the drying temperature is 40-65°C.

[0046] In some embodiments of the present invention, the recrystallization process can be carried out in a Y-type mixer.

[0047] In this invention, p and m are selected from 1 or 2.

[0048] The preparation method of the compound described in this invention is applicable to both continuous reaction processes and batch reaction processes.

[0049] In some embodiments of the present invention, preferably, the nucleophilic addition reaction is carried out in a microreactor.

[0050] The second aspect of the present invention provides the application of the method described in the first aspect of the present invention in improving the yield and purity of sulfinate compounds.

[0051] The present invention will be described in detail below through examples. In the following examples, the yield of disodium 2-hydroxy-2-sulfinic acid acetate is calculated as: actual mass / theoretical mass × 100%; the purity of disodium 2-hydroxy-2-sulfinic acid acetate is determined by the ratio of the peaks in a proton NMR spectrum. Specifically, 50 mg of the product is added to potassium hydrogen phthalate and heavy water as internal standards, and then NMR is performed. The purity is determined by the ratio of the peak area of ​​the product to that of potassium hydrogen phthalate. Unless otherwise specified, the following raw materials are all commercially available products. The compound with the structure shown in Formula II (R) 3 For H, R 4 The preparation of (methyl) is described in Aslabban, Merfat M., et al., "Detailed mechanistic studies into the reactivities of thiourea and substituted thiourea oxoacids: decompositions and hydrolyses of dioxides in basic media." The Journal of Physical Chemistry A 118.47(2014):11145-11154. The compound with the structure shown in Formula II (R) is prepared by referring to the synthetic method described in the article. 3 It is methyl, R 4The preparation of iodine (dimethyl) is described in Otoikhian A, Simoyi RH, Petersen JL. Oxidation of a dimethylthiourea metabolite by iodine and acidified iodate: N,N'-dimethylaminoiminomethanesulfinic acid (1). Chem Res Toxicol. 2005 Jul; 18(7): 1167-77.

[0052] Example 1

[0053] 110 mmol of thiourea dioxide was weighed and added to 3 mol of deionized water. 225 mmol of 50% sodium hydroxide solution was added dropwise to obtain solution A. 100 mmol of 50% glyoxylic acid solution was used as solution B. Solutions A and B were fed into a Y-type mixer at 0 °C using a feed pump at a flow rate of 10 ml / min. The products were continuously collected at the outlet of the channel and used as solution C. 100 g of methanol was used as solvent D. Solutions C and D were fed into the Y-type mixer at 0 °C using a feed pump at a flow rate of 10 ml / min. The products were continuously collected at the outlet of the channel, filtered, and the resulting solid product was dried in a vacuum drying oven at 45 °C for 12 h to finally obtain disodium 2-hydroxy-2-sulfinic acid acetate.

[0054] The reaction process is as follows:

[0055]

[0056] Among them, R 1 For H, R 2 H is H, and M is Na.

[0057] The product obtained in Example 1 was characterized by NMR: 13 C NMR (125MHz, D2O):

[0058] δ(ppm): 94.0(s), 177.9(s)

[0059] 1 H NMR (500MHz, D2O): δ (ppm): 4.18 (s, 1H)

[0060] Analysis revealed that the yield of disodium 2-hydroxy-2-sulfinate acetate was 83.4% of the obtained product, and the purity of the target product was calculated to be 78.2% by iodine reduction titration. No disodium 2-hydroxy-2-sulfinate acetate byproduct was detected by NMR spectroscopy.

[0061] Example 2

[0062] Weigh 110 mmol of thiourea dioxide, add 3 mol of deionized water, add 100 mmol of 50% glyoxylic acid solution, maintain at 25°C, add 225 mmol of 50% sodium hydroxide solution, and after the addition is complete, raise the temperature to 50°C and react for 4 h. After the reaction is complete, restore the temperature to 25°C, filter to obtain a solid crude product, and recrystallize the solid from water and methanol to obtain disodium 2-hydroxy-2-sulfinic acid acetate.

[0063] The reaction process is as follows:

[0064]

[0065] Among them, R 1 For H, R 2 H is H, and M is Na.

[0066] The product obtained in Example 1 was characterized by NMR: 13 C NMR (125MHz, D2O):

[0067] δ(ppm): 94.0(s), 177.9(s)

[0068] 1 H NMR (500MHz, D2O): δ (ppm): 4.18 (s, 1H)

[0069] Analysis revealed that the yield of disodium 2-hydroxy-2-sulfinate acetate was 82.5%, and the purity of the target product was calculated to be 74.1% using iodine reduction titration. No disodium 2-hydroxy-2-sulfinate acetate byproduct was detected by NMR spectroscopy.

[0070] Example 3

[0071] 110 mmol of thiourea dioxide was weighed and added to 3 mol of deionized water. 225 mmol of 50% sodium hydroxide solution was added dropwise to obtain solution A. 100 mmol of 50% zinc glyoxylate solution was used as solution B. Solutions A and B were fed into a Y-type mixer at 0 °C using a feed pump at a flow rate of 10 ml / min. The products were continuously collected at the outlet of the channel and used as solution C. 100 g of methanol was used as solvent D. Solutions C and D were fed into the Y-type mixer at 0 °C using a feed pump at a flow rate of 10 ml / min. The products were continuously collected at the outlet of the channel, filtered, and the resulting solid product was dried in a vacuum drying oven at 45 °C for 12 h to finally obtain a mixture of 2-hydroxy-2-sulfinic acid and zinc 2-hydroxy-2-sulfinic acid salt.

[0072] The yield of the mixed salt was 88.3%, and the purity of the target product was calculated to be 72.6% by iodine reduction titration. No sulfonate byproducts were detected in the NMR spectrum.

[0073] Example 4

[0074] 150 mmol of thiourea dioxide was weighed and added to 3 mol of deionized water. 225 mmol of 50% sodium hydroxide solution was added dropwise to obtain solution A. 100 mmol of 50% pyruvate aqueous solution was used as solution B. Solutions A and B were fed into a Y-type mixer at 50 °C using a feed pump at a flow rate of 20 ml / min. The product was continuously collected at the outlet and used as solution C. 100 g of methanol was used as solvent D. At 0 °C, solutions C and solvent D were fed into a Y-type mixer using a feed pump at a flow rate of 10 ml / min. The product was continuously collected at the outlet, filtered, and the resulting solid product was dried in a vacuum drying oven at 45 °C for 12 h to finally obtain disodium 2-hydroxy-2-sulfinic acid propionate, wherein R... 1 It is methyl, R 2 H is H, and M is Na.

[0075] The yield of disodium 2-hydroxy-2-sulfinic acid propionate was 78.6% in the obtained product, and the purity of the target product was calculated to be 72.3% by iodine reduction titration. No disodium 2-hydroxy-2-sulfinic acid propionate byproduct was detected by NMR spectroscopy.

[0076] Example 5

[0077] 130 mmol of thiourea dioxide was weighed and added to 2.5 mol of deionized water. 210 mmol of 50% sodium hydroxide solution was added dropwise to obtain solution A. 100 mmol of 50% glyoxylic acid solution was used as solution B. Solutions A and B were fed into a Y-type mixer at 10 °C using a feed pump at a flow rate of 20 ml / min. The product was continuously collected at the outlet of the channel and used as solution C. 100 g of ethanol was used as solvent D. Solutions C and D were fed into the Y-type mixer at 10 °C using a feed pump at a flow rate of 10 ml / min. The product was continuously collected at the outlet of the channel, filtered, and the resulting solid product was dried in a vacuum drying oven at 45 °C for 12 h to finally obtain disodium 2-hydroxy-2-sulfinic acid acetate, wherein R... 1 For H, R 2 H is H, and M is Na.

[0078] The yield of disodium 2-hydroxy-2-sulfinate acetate was 79.2% in the obtained product, and the purity of the target product was calculated to be 68.8% by iodine reduction titration. No disodium 2-hydroxy-2-sulfinate acetate byproduct was detected by NMR spectroscopy.

[0079] Example 6

[0080] Weigh 300 mmol of thiourea dioxide, add 5 mol of deionized water, and dropwise add 160 mmol of 50% sodium hydroxide solution to obtain solution A. Use 100 mmol of 50% glyoxylic acid solution as solution B. At 30°C, solutions A and B are fed into a Y-type mixer separately using a feed pump at a flow rate of 80 ml / min. The products are continuously collected at the outlet and used as solution C. Use 200 g of methanol as solvent D. At 30°C, solutions C and D are fed into a Y-type mixer separately using a feed pump at a flow rate of 80 ml / min. After continuous collection at the outlet, the products are filtered, and the resulting solid product is dried in a vacuum drying oven at 45°C for 12 h to finally obtain disodium 2-hydroxy-2-sulfinic acid acetate product, wherein R... 1 For H, R 2 H is H, and M is Na.

[0081] The yield of disodium 2-hydroxy-2-sulfinate acetate was 67.8% in the obtained product, and the purity of the target product was calculated to be 64.3% by iodine reduction titration. Disodium 2-hydroxy-2-sulfinate acetate was not detected in the NMR spectrum.

[0082] Example 7

[0083] 50 mmol of thiourea dioxide was weighed and added to 2 mol of deionized water. 300 mmol of 50% sodium hydroxide solution was added dropwise to obtain solution A. 100 mmol of 50% pyruvate aqueous solution was used as solution B. Solutions A and B were fed into a Y-type mixer at 70°C using a feed pump at a flow rate of 5 ml / min. The products were continuously collected at the outlet and used as solution C. 100 g of methanol was used as solvent D. Solutions C and D were fed into the Y-type mixer at 70°C using a feed pump at a flow rate of 80 ml / min. The products were continuously collected at the outlet, filtered, and the resulting solid product was dried in a vacuum drying oven at 45°C for 12 h to finally obtain disodium 2-hydroxy-2-sulfinic acid propionate, wherein R... 1 It is methyl, R 2 H is H, and M is Na.

[0084] Analysis revealed that the yield of disodium 2-hydroxy-2-sulfinic acid propionate was 71.5%, and the purity of the target product was calculated to be 65.7% using iodine reduction titration. No disodium 2-hydroxy-2-sulfinic acid propionate byproduct was detected by NMR spectroscopy.

[0085] Example 8

[0086] Weigh out the compound (R) with the structure shown in Formula II. 3 For H, R 4 Methanol (110 mmol) was added to deionized water (3 mol), and 50% sodium hydroxide solution (225 mmol) was added dropwise to obtain solution A. A 50% glyoxylic acid solution (100 mmol) was used as solution B. Solutions A and B were fed into a Y-type mixer at 0°C using a feed pump at a flow rate of 10 ml / min. The products were continuously collected at the outlet of the channel and used as solution C. 100 g of methanol was used as solution D. Solutions C and D were fed into the Y-type mixer at 0°C using a feed pump at a flow rate of 10 ml / min. The products were continuously collected at the outlet of the channel, filtered, and the resulting solid product was dried in a vacuum drying oven at 45°C for 12 h to finally obtain disodium 2-hydroxy-2-sulfinic acid acetate.

[0087] The reaction process is as follows:

[0088]

[0089] Among them, R 1 For H, R 2 For H, R 3 For H, R 4 M is methyl, and M is Na.

[0090] The product obtained in Example 10 was characterized by NMR: 13 C NMR (125MHz, D2O):

[0091] δ(ppm): 94.0(s), 177.9(s)

[0092] 1 H NMR (500MHz, D2O): δ (ppm): 4.18 (s, 1H)

[0093] The yield of disodium 2-hydroxy-2-sulfinate acetate was 79.2% in the obtained product, and the purity of the target product was calculated to be 73.1% by iodine reduction titration. No disodium 2-hydroxy-2-sulfinate acetate byproduct was detected in the NMR spectrum.

[0094] Example 9

[0095] Weigh out the compound (R) with the structure shown in Formula II. 3 It is methyl, R 4 Methanol (110 mmol) was added to deionized water (3 mol), and 50% sodium hydroxide solution (225 mmol) was added dropwise to obtain solution A. A 50% glyoxylic acid solution (100 mmol) was used as solution B. Solutions A and B were fed into a Y-type mixer at 0°C using a feed pump at a flow rate of 10 ml / min. The products were continuously collected at the outlet of the channel and used as solution C. 100 g of methanol was used as solution D. Solutions C and D were fed into the Y-type mixer at 0°C using a feed pump at a flow rate of 10 ml / min. The products were continuously collected at the outlet of the channel, filtered, and the resulting solid product was dried in a vacuum drying oven at 45°C for 12 h to finally obtain disodium 2-hydroxy-2-sulfinic acid acetate.

[0096] The reaction process is as follows:

[0097]

[0098] Among them, R 1 For H, R 2 For H, R 3 It is methyl, R 4 M is methyl, and M is Na.

[0099] The product obtained in Example 11 was characterized by NMR: 13 C NMR (125MHz, D2O):

[0100] δ(ppm): 94.0(s), 177.9(s)

[0101] 1 H NMR (500MHz, D2O): δ (ppm): 4.18 (s, 1H)

[0102] Analysis revealed that the yield of disodium 2-hydroxy-2-sulfinate acetate was 75.8%, and the purity of the target product was calculated to be 69.9% using iodine reduction titration. No disodium 2-hydroxy-2-sulfinate acetate byproduct was detected by NMR spectroscopy.

[0103] Comparative Example 1

[0104] Weigh out 100 mmol of sodium dithionite, add 2 mol of deionized water, and dropwise add 100 mmol of 50% glyoxylic acid solution. Maintain the temperature at 25°C, then dropwise add 200 mmol of 50% sodium hydroxide solution. After the addition is complete, raise the temperature to 50°C and react for 4 hours. After the reaction is complete, restore the temperature to 25°C, filter to obtain a solid crude product, and recrystallize the solid from water and methanol to obtain disodium 2-hydroxy-2-sulfinic acid propionate product, wherein R... 1 For H, R 2 H is H, and M is Na.

[0105] The yield of the obtained product, disodium 2-hydroxy-2-sulfinic acid acetate, was 33.5%, and the purity of the target product was calculated to be 64.6% by iodine reduction titration. NMR spectroscopy revealed a sodium sulfonate byproduct content of 23.7%.

[0106] The results above demonstrate that the method of this invention reacts aldehyde and / or keto acid compounds and their derivatives with a sulfinating reagent under alkaline conditions to generate sodium sulfite. The reaction yield is high, the selectivity is excellent, and no organic sulfonate sodium salts are found as byproducts. The byproduct urea has a significant difference in solubility from the product sodium sulfite, simplifying subsequent recrystallization purification, requiring less solvent, and achieving high separation efficiency.

[0107] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A method for preparing an organic sulfinate, characterized in that, The method includes: contacting the compound of Formula I or the compound of Formula I' with the compound of Formula II to carry out a nucleophilic addition reaction; Among them, R 1 Selected from H or C1-C6 alkyl, R 2 Selected from H, C1-C6 alkyl or M 1 ; R 3 R 4 Each is independently H or C1-C6 alkyl; M 1 Selected from NH4 or monovalent metal cations; M is selected from divalent metal cations of groups IIA, IIB, IVA, or VIII.

2. The method according to claim 1, wherein, R 1 Selected from H or C1-C5 alkyl groups; And / or, R 2 Selected from H, C1-C3 alkyl or M 1 ; And / or, R 3 R 4 Each is independently H or C1-C3 alkyl; And / or, M 1 Selected from monovalent metal cations.

3. The method according to claim 2, wherein, R 1 Selected from H or C1-C3 alkyl groups; And / or, R 2 Selected from H, methyl, ethyl or M 1 ; And / or, R 3 R 4 Each independently of H, methyl, or ethyl; And / or, M 1 Selected from sodium ions or potassium ions; And / or, M is selected from magnesium ions, calcium ions, zinc ions, or ferrous ions.

4. The method according to any one of claims 1-3, wherein, The nucleophilic reaction is carried out in the presence of a basic substance.

5. The method according to claim 4, wherein, The alkaline substance is selected from at least one of hydroxides, carbonates, bicarbonates, basic carbonates, and metal oxides, preferably from at least one of sodium hydroxide, sodium carbonate, sodium bicarbonate, potassium hydroxide, potassium carbonate, potassium bicarbonate, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium oxide, magnesium hydroxide, magnesium carbonate, magnesium bicarbonate, calcium oxide, calcium hydroxide, calcium carbonate, calcium bicarbonate, zinc oxide, zinc hydroxide, zinc carbonate, aluminum oxide, aluminum hydroxide, and basic aluminum carbonate.

6. The method according to claim 5, wherein, The alkaline substance is selected from at least one of sodium hydroxide, sodium carbonate, potassium hydroxide, and potassium carbonate.

7. The method according to claim 6, wherein, The reaction is carried out in the presence of a solvent; Preferably, the solvent is water.

8. The method according to any one of claims 4-7, wherein, The molar ratio of the alkaline substance to the compound shown in Formula I or Formula I' is 1-4.5:1; Preferably, the molar ratio of the compound represented by Formula II to the compound represented by Formula I or Formula I' is 0.5-3.5:

1.

9. The method according to any one of claims 1-8, wherein, The temperature for the nucleophilic addition reaction is 0-90℃; Preferably, the nucleophilic addition reaction takes 0.5-8 hours.

10. The use of the method according to any one of claims 1-9 in improving the yield and purity of sulfinate compounds.

Images