Preparation method of cyclic sulfate

A technology of cyclic sulfate and acid binding agent, applied in the direction of organic chemistry, etc., can solve the problems of low quality of crude product, increased cost of raw and auxiliary materials, difficulty in preparation of reagents, etc.

Active Publication Date: 2018-01-26
SHANGHAI CHEMSPEC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] 1. The reaction steps are long, the manufacturing cost is high, and the complexity of the process and the difficulty of post-processing are increased;
[0012] 2. The chloride ion content of the product is relatively high, and the process of removing chloride ion needs to increase the manufacturing cost of the project;
[0013] 3. The quality of the crude product is low and difficult to purify;
[0014] 4. The oxidation reaction uses expensive catalysts such as ruthenium metal oxide or ruthenium salt, which increases the cost of raw and auxiliary materials;
[0015] 5. It is necessary to contact with water during the manufacturing process, and the intermediate vinyl sulfite and the product vinyl sulfate are unstable in aqueous solution, which will easily lead to the reduction of p

Method used

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preparation example Construction

[0050]One aspect of the present invention provides a method for preparing a cyclic sulfuric acid ester. The structural formula of the cyclic sulfuric acid ester is shown in formula I, comprising the following steps: combining the compound of formula II with the presence of an acid-binding agent and a catalyst. Sulfuryl fluoride reaction is prepared to obtain the compound of formula I, and the reaction equation is as follows:

[0051]

[0052] In the preparation method of described cyclic sulfuric acid ester, n in formula I and / or formula II can be selected from 0, 1, 2, 3 or 4, thereby can constitute the corresponding number of carbon atoms in the formed formula I compound For ring structures, n can preferably be selected from 0 or 1.

[0053] In the preparation method of the cyclic sulfuric acid ester, R1, R2, R3, R4, R5, R6 can be independently selected from H, C1~C8 alkyl, aryl, C1~C8 alkoxy, halogen (for example, Fluorine, chlorine, bromine, iodine) or sulfate group, a...

Embodiment 1

[0072] The preparation of vinyl sulfate (formula III compound):

[0073]

[0074]Add 40g of ethylene glycol, 400mL of dichloromethane, 108g of solid potassium hydroxide, and 1.7g of tetra-n-butylammonium fluoride into a 1000mL reaction flask, keep the internal temperature at 0-5°C, and slowly introduce 98g of sulfuryl fluoride gas under stirring , reacted for 1 hour, blown nitrogen for 1 hour, filtered, and the filtrate was precipitated under reduced pressure to obtain a solid crude product. At room temperature, filter and dry to obtain 54.1 g of the product, with a yield of 67.6%. Test results: GC (%): >99.0%; AAS (ppm): Na 0.2, K 3, Fe 0.3, Ca 0.5; IC (ppm): SO 4 2- 49,F - 0.3, Cl - 0.1.

Embodiment 2

[0076] Preparation of vinyl sulfate:

[0077] In a 1000mL autoclave, add 40g of ethylene glycol, 250mL of methyl tert-butyl ether, 59g of solid sodium hydroxide, 20g of sodium sulfate, and 4.3g of tetra-n-butylammonium hydrogensulfate. 72 g of sulfuryl fluoride gas was introduced, and the reaction was sealed for 1 hour. After the reaction was completed, nitrogen was blown for 1 hour, filtered, and the filtrate was desolvated under reduced pressure to obtain a solid crude product. Add 100 mL of dichloromethane, 0.05 g of 15-crown-5, and 0.05 g of 18-crown-6, heat up and reflux to dissolve, and then slowly cool down to room temperature. After filtering and drying, 65.5 g of the product was obtained, with a yield of 81.8%. Test results: GC (%): >99.9%; AAS (ppm): Na 4, K 0.5, Fe 0.4, Ca 0.4; IC (ppm): SO 4 2- 55,F - 0.5, Cl - 0.2.

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Abstract

The invention relates to the field of organic synthesis, in particular to a preparation method of cyclic sulfate. The structural formula of cyclic sulfate is shown as formula I. The preparation methodof cyclic sulfate comprises the following step: cyclic sulfate in the formula I is prepared from a compound in formula II and sulfuryl fluoride by reacting in the presence of an acid binding agent and a catalyst. The preparation method of cyclic sulfate adopts short reaction step, cyclic sulfate can be prepared with the one-step reaction, cost of raw and auxiliary materials is low, and expensiveraw materials and oxidizing agent are not used.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of cyclic sulfuric acid ester. Background technique [0002] The diol compound shown in formula II is esterified to obtain the cyclic sulfuric acid ester shown in formula I. This cyclic sulfuric acid ester is a kind of additive that can make the electrolyte solution of lithium-ion batteries more effective. For example, vinyl sulfate (CAS No.: 1072-53-3) added to the lithium-ion battery electrolyte can inhibit the decline in the initial capacity of the battery, increase the initial discharge capacity, reduce the expansion of the battery after being placed at high temperature, and improve the charging capacity of the battery. Discharge performance and cycle times. Propylene sulfate (CAS No.: 1073-05-8) is used as an electrolyte additive for lithium batteries, which can improve the low-temperature performance of the electrolyte and prevent propylene carbonate m...

Claims

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Application Information

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IPC IPC(8): C07D327/10
Inventor 李晓亮何立田中肖航
Owner SHANGHAI CHEMSPEC CORP
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