CN117986162B - Preparation method of ethyl sulfonyl chloride - Google Patents
Preparation method of ethyl sulfonyl chloride Download PDFInfo
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- CN117986162B CN117986162B CN202410391695.4A CN202410391695A CN117986162B CN 117986162 B CN117986162 B CN 117986162B CN 202410391695 A CN202410391695 A CN 202410391695A CN 117986162 B CN117986162 B CN 117986162B
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- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 claims description 31
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 19
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- KQFAFFYKLIBKDE-UHFFFAOYSA-M sodium;ethanesulfonate Chemical compound [Na+].CCS([O-])(=O)=O KQFAFFYKLIBKDE-UHFFFAOYSA-M 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000005660 chlorination reaction Methods 0.000 claims description 11
- 235000010265 sodium sulphite Nutrition 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000012295 chemical reaction liquid Substances 0.000 claims description 7
- 239000012320 chlorinating reagent Substances 0.000 claims description 7
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 7
- 229960003750 ethyl chloride Drugs 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 239000012065 filter cake Substances 0.000 claims description 4
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000000413 hydrolysate Substances 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 claims description 2
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 claims description 2
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 2
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- WFCLYEAZTHWNEH-UHFFFAOYSA-N ethylthiocyanate Chemical compound CCSC#N WFCLYEAZTHWNEH-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- QEHKBHWEUPXBCW-UHFFFAOYSA-N nitrogen trichloride Chemical compound ClN(Cl)Cl QEHKBHWEUPXBCW-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of ethyl sulfonyl chloride. The preparation method is simple, the raw materials are easy to obtain, the product yield is high, the cost is low, and the industrialization is easy to realize.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to a preparation method of ethyl sulfonyl chloride.
Background
The ethyl sulfonyl chloride or ethane sulfonyl chloride with the structural formula CH 3CH2SO2 Cl is mainly used for organic synthesis and is an important intermediate of sulfonamide medicines and sulfonylurea herbicides.
The synthesis methods reported in the current domestic and foreign literature include an ethanethiol chlorination method, a diethyl sulfur chlorination method, an ethyl thiocyanate chlorination method, a sodium thiosulfate chlorination method and a diethyl sulfur electrolytic oxidation method.
EP0645357A1 reports that ethylsulfonyl chloride is obtained by continuously adding ethylthio alcohol and water into a reactor in proportion, simultaneously introducing chlorine gas, controlling the temperature to 29 ℃. The process requires continuous feeding and discharging and recycling of micro-reacted ethanethiol, achieves complete conversion, and has higher requirements on equipment, operation and automatic control. Meanwhile, ethanethiol has a strong odor and poses a great challenge to the operating environment.
Similar to the ethanethiol process, the description of modern general chemical reagents: diethyl disulfide is used as a raw material, and chlorine is used as a chlorinating agent, so that the ethyl sulfonyl chloride with higher purity is obtained. The process also has the problems of high equipment requirement and difficult solution of goods source supply.
The ethyl thiocyanate chlorination method is a synthesis method widely used in industry at present, and is reported that ethyl thiocyanate is added into water, cooled to 0-5 ℃ and chlorine is introduced until the reaction is in a lasting yellow-green color. The organic layer was separated, washed with sodium carbonate, dried over calcium chloride, and distilled under reduced pressure to give the product. The method has low yield, and the wastewater contains a large amount of oily liquid drops with pungent smell. Secondly, nitrogen trichloride with high explosion performance can be generated in the chlorination process, and the safety production is greatly influenced.
The sodium thiosulfate method is to add dimethyl sulfate into an aqueous solution of sodium thiosulfate, and to introduce chlorine gas for chlorination. The process has low yield of about 50%.
Disclosure of Invention
In order to overcome the problems in the synthesis, the invention provides a synthesis method suitable for industrialized production of ethyl sulfonyl chloride, the yield of the ethyl sulfonyl chloride reaches more than 90%, and the content of the ethyl sulfonyl chloride reaches more than 99%, so that the method has great production value.
The invention provides a preparation method of ethyl sulfonyl chloride, which is characterized in that the method comprises the following steps:
step 1, adding a solvent, sodium sulfite and a catalyst into a kettle through a feed inlet of the autoclave;
Step 2, introducing chloroethane into the kettle for catalytic sulfonation reaction;
Step 3, after the reaction is finished, post-treating the reaction liquid to obtain sodium ethyl sulfonate;
Step 4, putting sodium ethyl sulfonate into a reaction kettle, and adding a chlorinating agent and a catalyst for chlorination reaction;
And 5, carrying out post-treatment on the obtained chlorination reaction liquid to obtain ethyl sulfonyl chloride.
In the steps 1 and 2, the molar ratio of the addition amount of the chloroethane to the addition amount of the sodium sulfite is 1 (0.8-1.5), more preferably 1 (0.8-1.1).
The solvent used in the step 1 is one or a mixture of more of water, methanol, ethanol and isopropanol. Wherein the mass ratio of sodium sulfite to solvent is 1 (1-5), more preferably 1 (2-3).
The catalyst used in the step 1 is one or a mixture of more of tetramethyl ammonium bromide, tetraethyl ammonium bromide, tetrabutyl phosphonium chloride and tetraphenyl phosphonium bromide.
The chlorinating agent used in the step 4 is one of thionyl chloride, chlorosulfonic acid and phosphorus oxychloride. Preferably thionyl chloride. Wherein the molar ratio of the ethyl chloride to the thionyl chloride is 1: (1-2).
The catalyst used in the step 4 is one of N, N-dimethylformamide, pyridine and triethylamine, and preferably pyridine.
And 4, absorbing sulfur dioxide generated in the step 5 by sodium hydroxide to obtain a product sodium sulfite, wherein the sodium sulfite can be reused in the reaction, so that the generation of waste materials is greatly reduced, and the method is economical and environment-friendly.
The sodium ethyl sulfonate obtained in the step 3 needs to be used after the procedures of desolventizing, dehydrating and the like, and the treatment steps are as follows:
Step 3-1, cooling the reaction solution to room temperature and filtering;
step 3-2, washing the filtered filter cake by using a mixed solvent of isopropanol/water;
And 3-3, drying and dehydrating the washed filter cake to obtain sodium ethyl sulfonate.
The ethyl sulfonyl chloride obtained in the step 5 needs to be subjected to the procedures of hydrolysis, water washing, desolventizing and the like, and the treatment steps are as follows:
step 5-1, continuously heating the reaction liquid, and steaming out excessive chlorinating agent;
Step 5-2, after distillation is finished, the reaction solution is put into water for hydrolysis;
Step 5-3, washing and drying the hydrolysate;
and 5-4, concentrating the solvent to obtain the refined ethyl sulfonyl chloride.
The preparation process route of the ethyl sulfonyl chloride comprises the following steps:
Compared with the prior art, the ethyl sulfonyl chloride obtained by the method provided by the invention has the purity of more than 99%, the yield of more than 90%, and the preparation method is simple, the raw materials are easy to obtain, the cost is low, the industrialization is easy to realize, and the method has extremely high application value.
Detailed Description
Example 1: to a 2L autoclave, 347.1g of sodium sulfite, 395g of water, 300g of methanol and 3g of tetramethylammonium bromide were added, and the autoclave was closed to lower the temperature in the autoclave to 10℃or lower. 300g of ethyl chloride was introduced into the autoclave using a steel cylinder. Heating to 100-105 deg.c inside the reactor, maintaining the temperature for 4 hr and reaction pressure of 1MPa maximum. After the reaction, the temperature in the kettle is reduced to room temperature, and the reaction liquid is poured out and centrifuged. The centrifuged solids were slurried with 1:1 methanol/water solution and then centrifuged. And transferring the solid material into an oven for drying, wherein the dried solid is sodium ethyl sulfonate.
The sodium ethylsulfonate obtained was put into a 2L four-necked glass bottle with thermometer and mechanical stirring, 327.82g of thionyl chloride and 3g of N, N-dimethylformamide were added, the temperature was raised to reflux, and the temperature was kept for 2 hours. And after the heat preservation is finished, evaporating excessive thionyl chloride under negative pressure. The contents of the kettle were added to 1000g of water for hydrolysis. After hydrolysis, 294g of ethyl sulfonyl chloride is obtained by water washing, calcium chloride drying and solvent concentration and final distillation, and the molar yield is 83%, and the GC detection content is 99.15%.
Example 2: the method for preparing ethylsulfonyl chloride of this example differs from that of example 1 in that: the synthetic solvent of the sodium ethyl sulfonate is changed into water: isopropanol=1:1 ratio, the other steps being unchanged. 311.7g of ethylsulfonyl chloride were obtained, the molar yield was 88% and the GC content was 99.13%.
Example 3: the method for preparing ethylsulfonyl chloride of this example differs from that of example 1 in that: 347.1g of sodium sulfite, 695g of water and 3g of tetramethyl ammonium bromide are added into a reaction kettle, and 300g of chloroethane is introduced for reaction. The other steps are unchanged. 226.7g of ethylsulfonyl chloride were obtained, the molar yield was 64% and the GC content was 98.53%.
Example 4: the method for preparing ethylsulfonyl chloride of this example differs from that of example 2 in that: the obtained sodium ethylsulfonate was put into a 2L four-necked glass bottle, 327.82g of thionyl chloride and 3g of pyridine were added, and the temperature was raised to reflux and the temperature was kept for 2 hours. The other steps are unchanged. 319.1g of ethylsulfonyl chloride was obtained in a molar yield of 90.1% and a GC content of 99.3%.
Example 5: the method for preparing ethylsulfonyl chloride of this example differs from that of example 4 in that: the obtained sodium ethylsulfonate was put into a 2L four-necked glass bottle, 491.7g of thionyl chloride and 3g of pyridine were added, and the temperature was raised to reflux and the temperature was kept for 2 hours. The other steps are unchanged. 328.3g of ethylsulfonyl chloride were obtained, the molar yield was 92.6%, GC content detection: 99.35%.
The foregoing is merely exemplary embodiments of the present invention and is not intended to limit the scope of the invention, which is defined by the appended claims.
Claims (3)
1. A process for the preparation of ethylsulfonyl chloride, said process comprising the steps of:
step1, adding a solvent, sodium sulfite and a catalyst I into a kettle through a feed inlet of the autoclave;
Step 2, introducing chloroethane into the kettle for catalytic sulfonation reaction;
Step 3, after the reaction is finished, post-treating the reaction liquid to obtain sodium ethyl sulfonate;
Step 4, putting sodium ethyl sulfonate into a reaction kettle, and adding a chlorinating agent and a catalyst II for chlorination reaction;
Step 5, carrying out post-treatment on the obtained chlorination reaction liquid to obtain ethyl sulfonyl chloride, wherein the solvent used in the step 1 is a mixed solvent of one or more of methanol, ethanol and isopropanol and water, and the mass ratio of sodium sulfite to the solvent is 1 (1-5); the catalyst I used in the step 1 is one or a mixture of more of tetramethyl ammonium bromide, tetraethyl ammonium bromide, tetrabutyl phosphonium chloride and tetraphenyl phosphonium bromide; the second catalyst used in the step 4 is pyridine; the reaction temperature in the step 4 is 100-105 ℃, the reaction is carried out for 4 hours at a temperature and a maximum reaction pressure of 1MPa; the chlorinating agent used in the step 4 is thionyl chloride; step 4, absorbing sulfur dioxide generated in the step 5 by sodium hydroxide, and reusing the obtained sodium sulfite product into the reaction; the ethyl sulfonyl chloride obtained in the step 5 needs to be subjected to the procedures of hydrolysis, water washing and desolventizing, and the treatment steps are as follows:
step 5-1, continuously heating the reaction liquid, and steaming out excessive chlorinating agent;
Step 5-2, after distillation is finished, the reaction solution is put into water for hydrolysis;
Step 5-3, washing and drying the hydrolysate;
step 5-4, concentrating the solvent to obtain refined ethyl sulfonyl chloride; the purity of the ethyl sulfonyl chloride obtained by the method reaches more than 99 percent, and the yield is more than 90 percent.
2. The method according to claim 1, wherein in the step1 and the step 2, the molar ratio of the addition amount of ethyl chloride to the addition amount of sodium sulfite is 1 (0.8-1.5).
3. The method of claim 1, wherein the sodium ethyl sulfonate obtained in the step 3 is used after a desolventizing and dehydrating process, and the treatment steps are as follows:
Step 3-1, cooling the reaction solution to room temperature and filtering;
step 3-2, washing the filtered filter cake by using a mixed solvent of isopropanol/water;
And 3-3, drying and dehydrating the washed filter cake to obtain sodium ethyl sulfonate.
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| CN101875623A (en) * | 2009-11-17 | 2010-11-03 | 武汉工业学院 | Method for preparing methylsulphonic acid from halogenated methane |
| CN103992251A (en) * | 2014-05-19 | 2014-08-20 | 景立秋 | Preparation method of chloroalkyl sulfonyl chloride |
| CN114956990A (en) * | 2021-02-26 | 2022-08-30 | 上海惠和化德生物科技有限公司 | Continuous synthesis method of acyl chloride product |
| CN115920774A (en) * | 2022-12-30 | 2023-04-07 | 江西国化实业有限公司 | Autoclave for preparing ethylsulfonyl chloride |
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| DE2545644A1 (en) * | 1975-10-11 | 1977-04-14 | Bayer Ag | PROCESS FOR THE PRODUCTION OF SULPHONIC ACIDS |
| JP2005179325A (en) * | 2003-12-24 | 2005-07-07 | Sumitomo Chemical Co Ltd | Manufacturing method of sulfonic acid chloride |
| CN101698653B (en) * | 2009-10-30 | 2013-09-04 | 衢州中科精细化学有限公司 | Process for preparing high-purity methylsulfonic acid |
| CN102241613B (en) * | 2011-05-09 | 2013-06-05 | 南通维立科化工有限公司 | Method for preparing high-purity methylsulfonyl chloride from sodium methyl sulfonate |
| CN102584645A (en) * | 2011-12-24 | 2012-07-18 | 杭州庆丰农化有限公司 | Method for producing methanesulfonyl chloride by using sodium methanesulfonate under solvent-free condition |
| WO2024034520A1 (en) * | 2022-08-08 | 2024-02-15 | 住友精化株式会社 | Non-aqueous electrolyte for secondary battery, lithium ion battery, and lithium ion capacitor |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101875623A (en) * | 2009-11-17 | 2010-11-03 | 武汉工业学院 | Method for preparing methylsulphonic acid from halogenated methane |
| CN103992251A (en) * | 2014-05-19 | 2014-08-20 | 景立秋 | Preparation method of chloroalkyl sulfonyl chloride |
| CN114956990A (en) * | 2021-02-26 | 2022-08-30 | 上海惠和化德生物科技有限公司 | Continuous synthesis method of acyl chloride product |
| CN115920774A (en) * | 2022-12-30 | 2023-04-07 | 江西国化实业有限公司 | Autoclave for preparing ethylsulfonyl chloride |
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