Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF2 Cites 17 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this way, not only the system is large and the efficiency is low, but also the separation of the products is difficult, especially the diepoxide product with a higher boiling point.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing aliphatic diepoxides
  • Method for synthesizing aliphatic diepoxides
  • Method for synthesizing aliphatic diepoxides

Examples

Experimental program
Comparison scheme
Effect test

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.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com