Preparation of 4-fluoro-1,3-dioxolane-2-one

A manufacturing method and technology of dioxolane, applied in the direction of organic chemistry, etc., can solve the problems of high dielectric constant, low cycle characteristics, chlorine radicals easily remaining in solvents or refined products, etc., and achieve high-purity effects

Inactive Publication Date: 2009-09-02
DAIKIN IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] If such F-EC with remaining chlorine radicals is used for secondary batteries, etc., the cycle characteristics will be lowered, so it is necessary to control the concentration of chlorine radicals in the purified F-EC to 100ppm or less in terms of chloride ions , preferably below 50ppm, more preferably below 20ppm, but due to the high dielectric constant of F-EC, and the Cl in these chloride radicals - , HCl, Cl 2 Cannot be sufficiently removed by distillation, so these chloride groups tend to remain in the solvent or in the refined product

Method used

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  • Preparation of 4-fluoro-1,3-dioxolane-2-one
  • Preparation of 4-fluoro-1,3-dioxolane-2-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] Example 1 (antacid treatment before step (A))

[0099] Antacid treatment process (C)

[0100] To 500g (4.08mol, pH1~2) Cl-EC (manufactured by Aldrich), add 100g of amorphous silica-alumina gel (secado KW produced by Shinagawa Chemical Co., Ltd., neutral silica gel, trade name), in Stir at room temperature for 2 hours.

[0101] Solid component removal process (E)

[0102] After the stirring was completed, the amorphous silica-alumina gel was removed by filtration to prepare antacid-treated Cl-EC (pH 6-7).

[0103] Fluorination process (A)

[0104] A reflux tube was attached to the upper part of a 3L glass three-necked flask equipped with a stirring device, 355 g (6.12 mol) of spray-dried potassium fluoride was added, and the water was removed by flame drying while stirring under vacuum. Then, 1.3 L of acetonitrile and 500 g (4.08 mol) of antacid-treated Cl-EC were added and stirred using a syringe. The reaction was carried out at a reaction temperature of 85°C, and ...

Embodiment 2

[0123] Example 2 (antacid treatment after step (A))

[0124] Fluorination process (A)

[0125] A reflux tube was attached to the upper part of a 3L glass three-necked flask equipped with a stirring device, 355 g (6.12 mol) of spray-dried potassium fluoride was added, and the water was removed by flame drying while stirring under vacuum. Then, 1.3 L of acetonitrile and 500 g (4.08 mol) of untreated Cl-EC were added and stirred using a syringe. The reaction was carried out at a reaction temperature of 85°C, and the progress was analyzed by gas chromatography (GC). After reacting for 6 hours, it was confirmed that the peak of the raw material disappeared, and the reaction ended. After the reaction, the salt in the reaction product was filtered to obtain a reaction product liquid (pH 1-2).

[0126] Antacid treatment process (C)

[0127] 100 g of silica gel (Silica gel 60 manufactured by Merck, trade name, particle size 0.063 to 0.200 mm) was added to the obtained filtrate, and...

Embodiment 3

[0135] Example 3 (antacid treatment after step (A))

[0136] In addition to using amorphous silica-alumina gel (secado KW manufactured by Shinagawa Kasei Co., Ltd., neutral silica gel, trade name) instead of the silica gel used in the antacid treatment step (C) of Example 2, In the same manner as in Example 2, colorless and transparent F-EC was obtained as a fraction at 74°C (1 mmHg), with a yield of 65% and a GC purity of 99.6%.

[0137] The purified F-EC was carried out in the same manner as in Example 1, and the presence or absence of coloration, anion analysis, metal ion analysis, and pH measurement were performed. The results are shown in Table 1.

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Abstract

The present invention provides a method for preparing 4-fluoro-1,3-dioxolane-2-one with reduced halide content at high yield. The preparation of 4-fluoro-1,3-dioxolane-2-one is characterized in that the preparation comprises: the process (A) of fluorizating 4-chloro-1,3-dioxolane-2-one by fluridizer in organic solvent; the process (B) of distilling reaction form solution 4-chloro-1,3-dioxolane-2-one; and the process (C) of treating by antacid.

Description

technical field [0001] The present invention relates to a method for producing 4-fluoro-1,3-dioxolan-2-ones with reduced halide content in high yield. Background technique [0002] 4-Fluoro-1,3-dioxolan-2-one (hereinafter also referred to as "F-EC") is used as a solvent for electrolyte solutions of various batteries, taking advantage of its high dielectric constant. [0003] As a method for producing such F-EC, in addition to the method of directly fluorinating 1,3-dioxolan-2-one with fluorine gas as a starting material, it is also known to use a metal fluoride in approximately the same amount As a fluorinating agent, a method of substituting a chlorine atom at the 4-position of 4-chloro-1,3-dioxolane-2-one (hereinafter also referred to as "Cl-EC") with a fluorine atom (Patent Documents 1 to 3 ). [0004] In Patent Document 1, it is described that Cl-EC and potassium fluoride are mixed and reacted to obtain F-EC in a yield of 70%, but basic conditions such as reaction solv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/42
Inventor 高明天山内昭佳谷明范贺川米基璐中园葵坂田英郎中泽瞳富田真裕
Owner DAIKIN IND LTD
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