CN116120215A - Preparation method of p-hydroxybenzenesulfonyl chloride - Google Patents
Preparation method of p-hydroxybenzenesulfonyl chloride Download PDFInfo
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- CN116120215A CN116120215A CN202310154756.0A CN202310154756A CN116120215A CN 116120215 A CN116120215 A CN 116120215A CN 202310154756 A CN202310154756 A CN 202310154756A CN 116120215 A CN116120215 A CN 116120215A
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- hydroxybenzenesulfonyl
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- XKQZGGLHJYTXJA-UHFFFAOYSA-N 4-hydroxybenzenesulfonyl chloride Chemical compound OC1=CC=C(S(Cl)(=O)=O)C=C1 XKQZGGLHJYTXJA-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 22
- BYMHXIQVEAYSJD-UHFFFAOYSA-M sodium;4-sulfophenolate Chemical compound [Na+].OC1=CC=C(S([O-])(=O)=O)C=C1 BYMHXIQVEAYSJD-UHFFFAOYSA-M 0.000 claims abstract description 7
- 230000035484 reaction time Effects 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 239000012074 organic phase Substances 0.000 claims description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 16
- 238000000605 extraction Methods 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 13
- 238000002425 crystallisation Methods 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 9
- 238000002390 rotary evaporation Methods 0.000 claims description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 8
- 238000010791 quenching Methods 0.000 claims description 8
- 230000000171 quenching effect Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000003792 electrolyte Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
- YIPHYCQSJTXLFM-UHFFFAOYSA-N 4-hydroxybenzoyl chloride Chemical compound OC1=CC=C(C(Cl)=O)C=C1 YIPHYCQSJTXLFM-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002000 Electrolyte additive Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910010941 LiFSI Inorganic materials 0.000 description 2
- 229910013870 LiPF 6 Inorganic materials 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000003411 electrode reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000002761 liquid phase assay Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- -1 p-hydroxybenzoyl sulfonyl chloride Chemical compound 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
The invention discloses a preparation method of p-hydroxy benzene sulfonyl chloride, which takes sodium p-hydroxy benzene sulfonate and thionyl chloride as reaction raw materials to generate the p-hydroxy benzene sulfonyl chloride through DMF catalysis. The preparation method effectively shortens the reaction time and improves the yield, the yield and the purity of the p-hydroxy benzenesulfonyl chloride.
Description
Technical Field
The invention relates to the field of battery electrolyte additives, in particular to a preparation method of p-hydroxy benzenesulfonyl chloride.
Background
Electrolyte additives refer to small amounts of additives added to the electrolyte to improve the electrochemical performance of the electrolyte and to improve the quality of the cathode deposition. The electrolyte additive is some natural or artificial organic or inorganic compound, which does not participate in the electrode reaction in the electrolysis process, but can replace the electrochemical performance of the electrolyte system to influence the ion discharge condition, so that the electrolysis process is in a better state.
The p-hydroxy benzene sulfonyl chloride is an important medical intermediate and a modifier of a solid silicon-containing battery. The p-hydroxy benzenesulfonyl chloride is a widely used film forming additive, and compared with the traditional carbonate solvent, the S element has stronger electronegativity, so electrons are easier to be absorbed, and the reducibility of the S element on the surface of the negative electrode is stronger. The electrolyte film forming additive can form a protective layer on the surface of the electrode in preference to solvolysis, inhibit further oxidation of the electrolyte and greatly improve the stability of the battery. The existing synthesis method has low conversion rate of raw materials, about 50 percent, the obtained product is oily and can not be crystallized into solid, and the product yield is low, so that the preparation method of the p-hydroxy benzenesulfonyl chloride is established.
Disclosure of Invention
The invention aims to solve the problems of low yield and low yield of p-hydroxy benzenesulfonyl chloride in the prior art, and provides a preparation method of p-hydroxy benzenesulfonyl chloride.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the preparation method of the p-hydroxybenzenesulfonyl chloride comprises the following steps:
the preparation method is characterized in that sodium p-hydroxybenzenesulfonate and thionyl chloride are used as reaction raw materials under the protection of nitrogen, N-dimethylformamide is dropwise added, the reaction temperature and the reaction time are controlled, ice quenching reaction is carried out, the collected organic phase is washed and dried through extraction, the filtered filtrate is subjected to rotary evaporation, and then crystallization, filtration and drying are carried out, so that the p-hydroxybenzenesulfonyl chloride is obtained.
As an improved technical scheme, the sodium p-hydroxybenzenesulfonate and the thionyl chloride are added according to the mol ratio of 1:5-7.
As a modified technical scheme, the N, N-dimethylformamide is added according to the dosage of 80-150ml in every 100g of sodium parahydroxybenzenesulfonate.
As an improved technical scheme, the reaction temperature is controlled to be 40-50 ℃ and the reaction time is controlled to be 2-3h.
As an improved technical scheme, ethyl acetate is used as an extractant in extraction, the extraction times are 2 times, and the collected organic phase is washed 3 times with saturated brine.
As an improved technical scheme, anhydrous magnesium sulfate is added into an organic phase for drying, and then anhydrous sodium bicarbonate is added; wherein the addition amount of the anhydrous magnesium sulfate is 10-20% of the weight of the organic phase, and the addition amount of the anhydrous sodium bicarbonate is 5-10% of the weight of the organic phase.
As an improved technical scheme, the rotary steaming temperature is 35-60 ℃.
As an improved technical scheme, adding methylene dichloride into the product obtained by rotary distillation, and crystallizing at the temperature of-80-0 ℃; wherein the addition amount of the methylene dichloride is 1-5 times of the weight of the organic phase.
The reaction equation involved in the invention is as follows:
compared with the prior art, the invention has the beneficial effects that:
sodium p-hydroxybenzenesulfonate and thionyl chloride are used as reaction raw materials, N-dimethylformamide is dropwise added, the reaction temperature and the reaction time are controlled, ice quenching reaction is carried out, the collected organic phase is washed and dried through extraction, the filtered filtrate is subjected to rotary evaporation, and then crystallization, filtration and drying are carried out, so that the p-hydroxybenzenesulfonyl chloride is obtained. The method greatly improves the yield, the yield and the purity of the target product, and has simple process, and the target product is convenient for crystallization and drying.
Drawings
FIG. 1 is a liquid chromatography-mass spectrometry detection spectrum of p-hydroxybenzenesulfonyl chloride;
FIG. 2 is a solid mass spectrometry detection spectrum of p-hydroxybenzenesulfonyl chloride according to the present invention;
FIG. 3 is a liquid phase assay of p-hydroxybenzenesulfonyl chloride according to the present invention;
Detailed Description
The following description of the embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is evident that the embodiments described are only some, but not all embodiments of the invention.
Example 1
Under the protection of nitrogen, 196.16g of sodium p-hydroxybenzosulfonate is added into a reaction bottle, 594.9ml of thionyl chloride is added under the condition of 12 ℃, 80ml of N, N-dimethylformamide is dripped, the reaction temperature is controlled at 40 ℃, ice quenching reaction is added after 2h of reaction, ethyl acetate is added for extraction (extraction for 2 times), the collected organic phase is washed 3 times by saturated ice salt water, anhydrous magnesium sulfate (the added amount is 10% of the weight of the organic phase) is added for drying, anhydrous sodium bicarbonate solid (the added amount is 6.5% of the weight of the organic phase) is added, the filtrate collected after filtration is subjected to rotary evaporation (the temperature is 35 ℃) and the distilled product is added with dichloroethane with the weight of 1 time of the weight of the organic phase for crystallization, filtration and drying under the condition of-80 ℃ to obtain 178.17g of p-hydroxybenzoyl chloride with the yield of 92.5% and the purity of 99.91%.
Example 2
Under the protection of nitrogen, 196.16g of sodium p-hydroxybenzosulfonate is added into a reaction bottle, 654.3ml of thionyl chloride is added after cooling, 100ml of N, N-dimethylformamide is added dropwise, the reaction temperature is controlled at 43 ℃, ice quenching reaction is added after 2.3h of reaction, ethyl acetate is added for extraction (extraction for 2 times), the collected organic phase is washed 3 times with saturated ice salt water, anhydrous magnesium sulfate (the added amount is 12% of the weight of the organic phase) is added for drying, anhydrous sodium bicarbonate solid (the added amount is 7.5% of the weight of the organic phase) is added, the filtrate collected after filtration is subjected to rotary evaporation (the temperature is 45 ℃) and 180.68g of p-hydroxybenzoyl chloride is obtained after crystallization, filtration and drying at-50 ℃ under the condition that the weight of the organic phase is 2 times of dichloroethane, and the yield is 93.8% and the purity is 99.89%.
Example 3
Under the protection of nitrogen, 196.16g of sodium p-hydroxybenzosulfonate is added into a reaction bottle, 713.8ml of thionyl chloride is added after cooling, 120ml of N, N-dimethylformamide is added dropwise, the reaction temperature is controlled at 45 ℃, ice quenching reaction is added after 2.5h of reaction, ethyl acetate is added for extraction (extraction for 2 times), the collected organic phase is washed 3 times by saturated ice salt water, anhydrous magnesium sulfate (the added amount is 15% of the weight of the organic phase) is added for drying, anhydrous sodium bicarbonate solid (the added amount is 8% of the weight of the organic phase) is added, the filtrate collected after filtering is subjected to rotary evaporation (the temperature is 50 ℃) and the obtained product is added with 3 times of dichloroethane by weight of the organic phase, and crystallization, filtration and drying are carried out at the temperature of minus 30 ℃ to obtain 188.38g of p-hydroxybenzoyl chloride with the yield of 97.8% and the purity of 99.95%.
Example 4
Under the protection of nitrogen, 196.16g of sodium p-hydroxybenzosulfonate is added into a reaction bottle, 773.3ml of thionyl chloride is added after cooling, 135ml of N, N-dimethylformamide is added dropwise, the reaction temperature is controlled at 48 ℃, ice quenching reaction is added after 2.8h of reaction, ethyl acetate is added for extraction (extraction for 2 times), the collected organic phase is washed 3 times by saturated ice salt water, anhydrous magnesium sulfate (the addition amount is 18% of the weight of the organic phase) is added for drying, anhydrous sodium bicarbonate solid (the addition amount is 9% of the weight of the organic phase) is added, the filtrate collected after filtration is subjected to rotary evaporation (the temperature is 55 ℃) and the obtained product is added with 4 times of dichloroethane by weight of the organic phase, and crystallization, filtration and drying are carried out at the temperature of minus 20 ℃ to obtain 182.03g of p-hydroxybenzoyl chloride with the yield of 94.5% and the purity of 99.92%.
Example 5
Under the protection of nitrogen, 196.16g of sodium p-hydroxybenzosulfonate is added into a reaction bottle, 832.8ml of thionyl chloride is added after cooling, 150ml of N, N-dimethylformamide is added dropwise, the reaction temperature is controlled at 50 ℃, ice quenching reaction is added after 3h of reaction, ethyl acetate is added for extraction (extraction for 2 times), the collected organic phase is washed with saturated ice salt water for 3 times, anhydrous magnesium sulfate (the addition amount is 20% of the weight of the organic phase) is added for drying, anhydrous sodium bicarbonate solid (the addition amount is 10% of the weight of the organic phase) is added, the filtrate collected after filtration is subjected to rotary evaporation (the temperature is 60 ℃), dichloroethane with 5 times of the weight of the organic phase is added into the distilled product, crystallization, filtration and drying are carried out at 0 ℃ to obtain 183.18g of p-hydroxybenzosulfonyl chloride with the yield of 95.1% and the purity of 99.90%.
In order to better demonstrate the preparation method of the invention, the yield and purity of the p-hydroxybenzoyl sulfonyl chloride can be improved, and 2 comparative examples are given with reference to example 3;
comparative example 1
Unlike example 3, petroleum ether was used instead of methylene chloride for crystallization, and the rest was the same; 164.88g of p-hydroxybenzenesulfonyl chloride is obtained, the yield is 85.6%, and the purity is 98.93%.
Comparative example 2
Unlike example 3, petroleum ether was used instead of methylene chloride for crystallization, and the rest was the same; 135.03g of p-hydroxybenzenesulfonyl chloride is obtained, the yield is 70.1%, and the purity is 97.90%.
Application experiment:
ternary material NCM (622) lithium is used as a positive electrode material, a negative electrode adopts intermediate phase carbon microspheres, positive and negative current collectors are distributed into aluminum foils and copper foils, a diaphragm adopts a ceramic diaphragm to form a soft-package battery, after electrolyte is injected, the soft-package battery is assembled in a glove box, and after standing for 8 hours, the soft-package battery is tested. And respectively charging and discharging at the constant temperature of 25 ℃ at the room temperature by 1/10C 3.0V to over 4.2V to activate the battery, thus obtaining the battery to be tested. The electrolyte tested included a base electrolyte E1 and an electrolyte E2, the composition of which is shown below:
1. basic electrolyte E1
EC：Solution-1：DEC＝3：3：4(v:v:v)，LiPF 6 ：1.0M，0.5％LiFSI，
1％VC
2. Electrolyte E2
EC：Solution-1：DEC＝3：3：4(v:v:v)，LiPF 6 ：1.0M，0.5％LiFSI，
1% of VC and 1% of p-hydroxy benzenesulfonyl chloride;
test results:
1. the test results after 60℃cycle are as follows:
TABLE 2
2. The battery was placed in a low temperature cabinet at-30 ℃ or-40 ℃ for 240min, respectively, and then the capacity retention rate of the battery was measured.
TABLE 3 Table 3
The present invention is not limited to the above-mentioned embodiments, and any person skilled in the art, based on the technical solution of the present invention and the inventive concept thereof, can be replaced or changed within the scope of the present invention.
Claims (8)
1. The preparation method is characterized in that sodium p-hydroxybenzenesulfonate and thionyl chloride are used as reaction raw materials under the protection of nitrogen, N-dimethylformamide is dropwise added, the reaction temperature and the reaction time are controlled, ice quenching reaction is added, the collected organic phase is washed and dried through extraction, the filtered filtrate is subjected to rotary evaporation, and then crystallization, filtration and drying are carried out, so that the p-hydroxybenzenesulfonyl chloride is obtained.
2. The method for preparing p-hydroxybenzenesulfonyl chloride according to claim 1, characterized in that the sodium p-hydroxybenzenesulfonate and thionyl chloride are added in a molar ratio of 1:5-7.
3. A process for the preparation of p-hydroxy benzenesulfonyl chloride as claimed in claim 1, wherein said N, N-dimethylformamide is added in an amount of 80-150ml per 100g of sodium p-hydroxy benzenesulfonate.
4. The method for preparing p-hydroxybenzenesulfonyl chloride according to claim 1, characterized in that the reaction temperature is controlled to be 40-50 ℃ and the reaction time is controlled to be 2-3h.
5. The method for preparing p-hydroxybenzenesulfonyl chloride according to claim 1, characterized in that ethyl acetate is used as an extractant in the extraction for 2 times, and the collected organic phase is washed with saturated brine for 3 times.
6. The method for preparing p-hydroxy benzenesulfonyl chloride according to claim 1, wherein the anhydrous magnesium sulfate is added into the organic phase for drying, and then the anhydrous sodium bicarbonate is added; wherein the addition amount of the anhydrous magnesium sulfate is 10-20% of the weight of the organic phase, and the addition amount of the anhydrous sodium bicarbonate is 5-10% of the weight of the organic phase.
7. The method for preparing p-hydroxybenzenesulfonyl chloride according to claim 1, characterized in that the temperature of the rotary evaporation is 35-60 ℃.
8. The process for producing p-hydroxybenzenesulfonyl chloride according to claim 4, characterized in that methylene chloride is added to the product obtained by the spin distillation, and crystallization is carried out at-80 to 0 ℃; wherein the addition amount of the methylene dichloride is 1-5 times of the weight of the organic phase.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130078570A1 (en) * | 2011-09-26 | 2013-03-28 | Atsushi Hieno | Method of forming pattern and laminate |
| CN105439914A (en) * | 2014-09-17 | 2016-03-30 | 复旦大学 | 4-aminoacylphenoxyacetamide compound and medicine uses thereof |
| CN109369476A (en) * | 2018-11-30 | 2019-02-22 | 嘉兴市秀洲区洪合镇中学 | A kind of preparation method of medicine intermediate parachloroben-zenesulfonyl chloride |
-
2023
- 2023-02-23 CN CN202310154756.0A patent/CN116120215A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130078570A1 (en) * | 2011-09-26 | 2013-03-28 | Atsushi Hieno | Method of forming pattern and laminate |
| CN105439914A (en) * | 2014-09-17 | 2016-03-30 | 复旦大学 | 4-aminoacylphenoxyacetamide compound and medicine uses thereof |
| CN109369476A (en) * | 2018-11-30 | 2019-02-22 | 嘉兴市秀洲区洪合镇中学 | A kind of preparation method of medicine intermediate parachloroben-zenesulfonyl chloride |
Non-Patent Citations (2)
| Title |
|---|
| HENRIK C. HANSEN ET AL: "Stilbene analogs as inducers of apolipoprotein-I transcription", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》, vol. 45, 31 December 2010 (2010-12-31), pages 2018 - 2023, XP026976525 * |
| ROBERT W.CAMPBELL ET AL: "4-Hydroxybenzenesulfonyl chloride", 《J.ORG.CHEM》, vol. 38, no. 5, 31 December 1973 (1973-12-31), pages 1047 * |
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