Phase-transfer catalytic synthesis method of 3, 4-epoxy cyclohexyl methyl-3', 4'-epoxy cyclohexyl formate

A technology of phase transfer catalysis and hexylmethyl, which is applied in the field of organic synthesis, can solve the problems of complex catalyst preparation process, unavailable raw materials, and low catalytic yield, and achieve the effect of large market application value, low cost, and simple process

Pending Publication Date: 2022-01-04
QUANZHOU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have the following characteristics: (1) the 3,4-epoxy cyclohexyl formic acid-3,4'-epoxy cyclohexyl methyl ester resin appearance of (1) preparation is yellow, and there are more catalyst residues
(2) The preparation process of solvent-free catalyst is complicated, the raw material is not easy to get, and its catalytic yield is low
Therefore, how to prepare 3,4-epoxycyclohexylcarboxylate-3,4'-epoxycyclohexyl methyl ester resin with high yield and high quality is a technical challenge

Method used

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  • Phase-transfer catalytic synthesis method of 3, 4-epoxy cyclohexyl methyl-3', 4'-epoxy cyclohexyl formate
  • Phase-transfer catalytic synthesis method of 3, 4-epoxy cyclohexyl methyl-3', 4'-epoxy cyclohexyl formate
  • Phase-transfer catalytic synthesis method of 3, 4-epoxy cyclohexyl methyl-3', 4'-epoxy cyclohexyl formate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) In the reaction vessel, add 20g of dichloromethane and 0.2g of sodium ethoxide catalyst, under stirring, rise to 35°C, add 100g of 3-cyclohexene-1-carbaldehyde dropwise through the constant pressure funnel, and react at constant temperature for 1h after dropping. After washing with 3.7% dilute hydrochloric acid, separating liquid and distilling under reduced pressure, the epoxidized intermediate 3,4-cyclohexenecarboxylate-3',4'-cyclohexene methyl ester was obtained.

[0042] (2) 50g 3,4-cyclohexenecarboxylic acid-3',4'-cyclohexene methyl ester, 100g dichloroethane, 2.8g phase transfer catalyst [C 16 h 33 N(CH 3 ) 3 ] 3 PW 4 o 24 , 0.16g recovering agent cetyltrimethylammonium bromide, 0.4g buffering agent sodium bicarbonate were added to the reaction vessel, the temperature was raised to 55°C and refluxed, 75g 30% hydrogen peroxide was added dropwise at constant pressure and reacted at constant temperature for 1 hour, and the reaction was completed Cool to roo...

Embodiment 2

[0048] (1) In the reaction vessel, add 15g of dichloroethane and 0.5g of aluminum isopropoxide catalyst, under stirring, rise to 37°C, add 100g of 3-cyclohexene-1-carbaldehyde dropwise into the constant pressure funnel, and keep the temperature constant After reacting for 1 h, washing with 3.7% dilute hydrochloric acid, separating liquid and distilling under reduced pressure, the epoxidized intermediate 3,4-cyclohexenecarboxylate-3',4'-cyclohexene methyl ester was obtained.

[0049] (2) 50g 3,4-cyclohexenecarboxylic acid-3', 4'-cyclohexene methyl ester, 100g dichloroethane, 3g phase transfer catalyst [C 18 h 37 N(CH 3 ) 3 ] 3 PW 4 o 24 , 0.18g recovering agent octadecyltrimethylammonium bromide, 0.5g buffering agent dipotassium hydrogen phosphate were added to the reaction vessel, the temperature was raised to 60°C and refluxed, 75g 30% hydrogen peroxide was added dropwise at constant pressure for 1 hour at constant temperature, and the reaction After cooling to room tem...

Embodiment 3

[0053] (1) In the reaction vessel, add 18g of chloroform and 0.15g of sodium methoxide catalyst, under stirring, rise to 40°C, add 100g of 3-cyclohexene-1-carbaldehyde dropwise into the constant pressure funnel, and react at constant temperature for 1h after dropping. After washing with 3.7% dilute hydrochloric acid, separating liquid and distilling under reduced pressure, the epoxidized intermediate 3,4-cyclohexenecarboxylate-3',4'-cyclohexene methyl ester was obtained.

[0054] (2) 50g 3,4-cyclohexenecarboxylic acid-3', 4'-cyclohexene methyl ester, 100g chloroform, 2.8g phase transfer catalyst [C 16 h 33 N(CH 3 ) 3 ] 3 PW 4 o 24 , 0.16g recovery agent cetyltrimethylammonium bromide, 0.35g buffering agent sodium acetate were added to the reaction vessel, the temperature was raised to 65°C and refluxed, 75g 30% hydrogen peroxide was added dropwise at constant pressure to complete the constant temperature reaction for 1h, and the reaction was completed and cooled to room ...

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Abstract

The invention discloses a phase transfer catalytic synthesis method of 3, 4-epoxy cyclohexyl methyl-3', 4'-epoxy cyclohexyl formate. The method comprises the following steps of: carrying out Tischenko reaction on 3-cyclohexene-1-formaldehyde as a raw material to obtain an epoxidized raw material 3, 4-cyclohexene formic acid-3', 4'-cyclohexene methyl ester, and performing epoxidation on double bonds of the 3, 4-cyclohexene formic acid-3', 4'-cyclohexene methyl ester by taking hydrogen peroxide as a green oxygen source under the catalysis of a phase transfer catalyst peroxy phosphotungstic acid (peroxy phosphomolybdic acid) quaternary ammonium salt, thereby obtaining cationic epoxy resin 3, 4-epoxy cyclohexyl methyl-3', 4'-epoxy cyclohexyl formate for 3D printing. According to the preparation method, the peroxy phosphotungstic acid (peroxy phosphomolybdic acid) quaternary ammonium salt phase transfer catalyst is applied, a buffer agent inhibits hydrolysis of the product, so that high yield is achieved, efficient recovery of the catalyst is achieved, and the prepared product has the advantages of being resistant to weather, high in purity, colorless, resistant to yellowing, good in electric insulativity and low in viscosity and has good application values in the fields of 3D printing, coatings, packaging, electronics, automobiles and the like.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a phase-transfer catalytic synthesis method of 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexyl carboxylate. Background technique [0002] Epoxy resin refers to a class of organic polymer compounds containing two or more epoxy groups in its molecular structure, and is an important thermosetting resin. Since the advent of epoxy resin for more than 60 years, due to its excellent characteristics, epoxy resin products have been widely used in many fields, especially the continuous development of new varieties and curing agents, as well as the innovation of deep processing technology for epoxy resin products. All these make the epoxy resin industry develop rapidly. At present, ordinary bisphenol A epoxy resins account for more than 90% of the market volume. However, with the development of high-tech industries, some performance defects of ordinary bisphenol A epoxy resins ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/12C07D303/44B01J27/19B01J31/02
CPCC07D301/12C07D303/44B01J27/19B01J31/0239B01J2231/72
Inventor 卓东贤陈少云王铭清徐伟达瞿波王睿郑燕玉刘小英李文杰
Owner QUANZHOU NORMAL UNIV
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