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Preparation method of methylene methanedisulfonate

A technology of methylene disulfonate and methylene disulfonyl chloride, applied in the direction of organic chemistry, etc., can solve the problems of low efficiency of methylene disulfonate, achieve high product yield, high economic benefit, meet the Apply the desired effect

Active Publication Date: 2021-03-30
烟台海川化学制品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The invention aims at the problem of low efficiency in the existing synthesis of methylene disulfonate, and provides a method for preparing methylene disulfonate. The method uses methylene disulfonyl chloride and dichloromethane as raw materials, and uses carbon The acid salt is an oxygen donor, using 4-dimethylaminopyridine (DMAP) as a catalyst, reacting at 0-50°C for 12-36h, and obtaining it after recrystallization. The synthetic route is as follows:

Method used

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  • Preparation method of methylene methanedisulfonate
  • Preparation method of methylene methanedisulfonate
  • Preparation method of methylene methanedisulfonate

Examples

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Embodiment 1

[0020] A kind of preparation method of methylene disulfonate, concrete operation steps are: take by weighing 70.3g methylene disulfonyl chloride, 112.1g dichloromethane, 91.2g potassium carbonate, 1.6g DMAP join in the 500ml there-necked bottle, pass Into a dry and stable nitrogen flow, the reaction system was stirred at 10°C for 12h, and then filtered; the filter cake was extracted with 200g of dimethyl carbonate, the insoluble matter was removed by filtration, the filtrate was distilled to remove the solvent until a white solid was precipitated, then cooled to 5°C and stirred for 0.5 h Filtration gave 42.4 g of white crystal methylene disulfonate.

[0021] 99.7% detected by GC, the yield is 68.3%. The melting point is 148.05-153.02°C.

[0022] 1 HNMR (400MHZ, deuterated acetone) δ (ppm): 5.82 (s, 2H), 6.19 (s, 2H); 13CNMR (100MHZ, deuterated acetone) δ (ppm): 68.76, 91.76.HRMS (ESI) for C2H4O6S2 ,calcd:188,found:188.

Embodiment 2

[0024] A kind of preparation method of methylene disulfonate, concrete operation steps are: take by weighing 42.6g methylene disulfonyl chloride, 67.9g dichloromethane, 53g sodium carbonate, 1.2g DMAP join in the 500ml there-necked flask, pass into Dry and stable nitrogen flow, the reaction system was stirred at 30°C for 12h, then filtered; the filter cake was extracted with 230g of ethyl acetate, filtered to remove insoluble matter, the filtrate was distilled to remove solvent until a white solid was precipitated, then cooled to -5°C, stirred for 0.5h and filtered , The filter cake was dried to obtain 23.8 g of white crystal methylene disulfonate.

[0025] GC detection 99.6%, the yield is 63.2%. The melting point is 148.05-153.02°C.

[0026] 1 HNMR (400MHZ, deuterated acetone) δ (ppm): 5.82 (s, 2H), 6.19 (s, 2H); 13CNMR (100MHZ, deuterated acetone) δ (ppm): 68.76, 91.76.HRMS (ESI) for C2H4O6S2 ,calcd:188,found:188.

Embodiment 3

[0028] A preparation method of methylene disulfonate, the specific operation steps are: Weigh 70.3 methylene disulfonyl chloride, 168.2 g dichloromethane, 268.8 g cesium carbonate, 2.0 g DMAP into a 500 ml three-necked bottle, pass into Stir the reaction system at 40°C for 12 hours in a dry and stable nitrogen flow, then filter; use 400g of ethyl acetate to extract the filter cake, filter to remove insoluble matter, distill the filtrate to remove the solvent until a white solid is precipitated, then cool down to -10°C and stir for 0.5h Filter and dry the filter cake to obtain 48.2 g of white crystal methylene disulfonate.

[0029] GC detection 99.7%, the yield is 77.6%. The melting point is 148.05-153.02°C.

[0030] 1 HNMR (400MHZ, deuterated acetone) δ (ppm): 5.82 (s, 2H), 6.19 (s, 2H); 13CNMR (100MHZ, deuterated acetone) δ (ppm): 68.76, 91.76.HRMS (ESI) for C2H4O6S2 ,calcd:188,found:188.

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Abstract

The invention discloses a preparation method of methylene methanedisulfonate, which comprises the following steps: by using methylene disulfonyl chloride and dichloromethane as raw materials, carbonate as an oxygen donor and 4dimethylaminopyridine as a catalyst, reacting at 0-50 DEG C for 12-36 hours, and recrystallizing a reaction product to obtain the methylene methanedisulfonate. Herein, the raw materials for synthesizing methylene methanedisulfonate are cheap and easy to obtain, so that the cost for producing methylene methanedisulfonate is low, the economic benefit is high, phosphorus pentoxide is not needed, viscous phosphoric acid is not generated, and phosphate treatment is avoided. According to the method, dichloromethane is used as a reaction raw material, carbonate is used as anoxygen donor, paraformaldehyde is not used, and formaldehyde wastewater difficult to treat is avoided; therefore, the method is mild in reaction process condition, simple and safe in operation process, high in product yield and short in production period, a high-purity product is obtained, and the application requirement of the lithium battery can be met.

Description

technical field [0001] The present invention relates to organic synthesis, in particular to a preparation method of methylene disulfonate. Background technique [0002] The battery added with methylene disulfonate (MMDS) has good high-temperature cycle performance and is suitable for power batteries, especially power batteries with lithium manganate as the positive electrode material. MMDS can prevent the Mn melted out at high temperature from being adsorbed on the negative electrode On the surface, the impedance rise is suppressed, the cycle characteristics are effectively improved, and the cycle life can be greatly increased. [0003] Patent CN101426776 (Japan Sumitomo Seika Co., Ltd.), this patent uses solid methylene disulfonic acid and paraformaldehyde as reaction raw materials, 10h reaction at 120 ° C to obtain MMDS, is a solvent-free solid phase reaction, the reaction is difficult to control, and the reaction is not stable. Full, lower yield. The patent synthetic ro...

Claims

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Application Information

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IPC IPC(8): C07D327/00
CPCC07D327/00
Inventor 李军张钊冯绍全赵青山宫振山衣凯华韦俨珊
Owner 烟台海川化学制品有限公司
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