Method for synthesizing aliphatic diepoxides

A technology of a diepoxide compound and a synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of difficult product separation, large system, low efficiency, etc., and achieve the effects of improving safety, improving efficiency, and inhibiting hydrolysis

Active Publication Date: 2008-08-27
DALIAN TRICO CHEM
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

In this way, not only the system is large and the efficiency is low, but also the separation

Method used

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  • Method for synthesizing aliphatic diepoxides
  • Method for synthesizing aliphatic diepoxides
  • Method for synthesizing aliphatic diepoxides

Examples

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Embodiment 1

[0041] Catalytic double epoxidation synthesis of embodiment 1 CER-4221

[0042] 44g of 3-cyclohexenecarboxylic acid-3'-cyclohexene methyl ester, 2.6g of [C 16 h 33 N(CH 3 ) 3 ] 3 [W 2 o 3 (O 2 ) 4 ], 88g dichloroethane heated and stirred to 50 degrees together. Add 35% hydrogen peroxide (H 2 o 2 0.5mol, 2.5eq), the reaction is exothermic. The reaction was stirred for 1 hour, and a sample was taken for detection. The conversion rate is 99%, and the ratio of single to double is 1:18. After cooling to room temperature, the aqueous layer was separated. The organic layer was washed three times with saturated brine, dried over anhydrous sodium sulfate, passed through a short silica gel column, and concentrated to obtain 33.5 g of a colorless or pale yellow viscous liquid. The yield is 67%, and the epoxy equivalent is about 154.

example 2

[0043] Catalytic double epoxidation synthesis of example 2 CER-4221

[0044] 44g of 3-cyclohexenecarboxylic acid-3'-cyclohexene methyl ester, 3.3g of [C 5 h 5 NC 16 h 33 ] 2 [W 2 o 3 (O 2 ) 4 ], 88g chloroform is heated and stirred to 50 degrees together. 25% hydrogen peroxide (H 2 o 2 After the pH value of 0.5mol, 2.5eq) is adjusted to about 4, it is added dropwise in the reaction solution, and the reaction exotherm is violent. The reaction was stirred for 1 hour, and a sample was taken for detection. The conversion rate is 99%, and the ratio of single to double is 1:18. Cool to room temperature and separate the liquids. The organic layer was washed three times with water, dried over anhydrous sodium sulfate, passed through a short silica gel column, and concentrated to obtain 38.8 g of a colorless or pale yellow viscous liquid. The yield is 77%, and the epoxy equivalent is about 135.

example 3

[0045] Catalytic double epoxidation synthesis of example 3 CER-4221

[0046] 44g of 3-cyclohexenecarboxylic acid-3'-cyclohexene methyl ester, 2.64g of [C 5 h 5 NC 16 h 33 ] 2 [W 2 o 3 (O 2 ) 4 ], 1g sodium bicarbonate, and 88g dichloroethane were heated and stirred to 60 degrees together. 35% hydrogen peroxide (H 2 o 2 0.5mol, 2.5eq)) was added dropwise to the system, and the reaction was exothermic violently. The reaction was stirred for 1 hour, and a sample was taken for detection. The conversion rate is 99%, and the ratio of single to double is 1:17. Cool to room temperature and separate the liquids. The organic layer was washed three times with water and saturated salt, dried over anhydrous sodium sulfate, passed through a short silica gel column, and concentrated to obtain 45 g of a colorless or light yellow viscous liquid. The yield is 90%, and the epoxy equivalent is about 138.

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Abstract

The invention provides a method for synthesizing aliphatic diepoxide safely and effectively in large scale. The synthesis method uses hydrogen peroxide as oxygen resource and uses heteropoly acid containing molybdenum or tungsten as phase transfer catalyst, in solvent to convert diolefin substrate completely into aliphatic diepoxide. The content of single expoy product in the product is 5-7% at mol ratio to effectively control the epoxy equivalent of product. The invention uses safe hydrogen peroxide as oxygen resource, to avoid using dangerous and explosive peroxy acetic acid, to improve production safety. And in the reaction, the invention eliminates over olefin and uses buffer to adjust the pH value of the solution to inhibit the hydrolysis of product, thereby improving production efficiency. The invention adds hydrogen peroxide via premixing emulsion and dropping method to eliminate the initiation of epoxidation, therefore the reaction is gentle and controllable and is suitable for industrial large production.

Description

technical field [0001] The invention relates to a method for synthesizing aliphatic epoxy compounds by catalytic epoxidation, especially the synthesis of diepoxides. Background technique [0002] Aliphatic diepoxy compound is a kind of epoxy resin developed by United Carbon Corporation. Compared with bisphenol A epoxy resin, it has the characteristics of good thermal stability, high weather resistance, and excellent electrical insulation performance. Therefore, aliphatic Diepoxides are widely used in coatings, packaging, electronics, automobiles and other fields, and are in great demand in the world. At present, the industry mostly adopts peracid method to synthesize aliphatic diepoxides. However, due to the use of high-concentration peracetic acid as an oxidant, and high-concentration peracetic acid is prone to explosion, there is a great potential safety hazard in the production process. Aliphatic diepoxides are a class of acid-sensitive substances, and the peracid metho...

Claims

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Application Information

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IPC IPC(8): C07D301/12C07D407/12C07D407/04
Inventor 王军伟张长晔隋立军史超锋夏胜远马国栋
Owner DALIAN TRICO CHEM
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