Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for preparing dioxidized 4-vinyl cyclohexene

A technology of vinyl cyclohexene and carbon dioxide, which is applied in the direction of organic chemistry, can solve the problems of high cost and low yield of double epoxidation products, and achieve the effects of low energy consumption, simple and fast reaction process, and cost reduction

Inactive Publication Date: 2008-10-29
EAST CHINA NORMAL UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wherein, the peroxyacetic acid with mass fraction greater than 40% is the oxidant most, the single epoxidation product yield reaches more than 70%, and the double epoxidation product is at most 25% (Jiao Jiajun, Wu Xiaofeng. 4-vinyl cyclohexene epoxidation Reaction Research. Fine Chemical Industry, 1997, 14(1): 41~42) The yield of the double epoxidation product in this method is too low, so it is not suitable for the production of this product
Oxidation with molecular oxygen has also been reported (Kiyotomi Kaneda, Shigeru Hartuna, Toshinobu Imanaka. A Convenient Synthesis of Epoxides from Olefins Using Molecular Oxygen in the Absence of Metal Catalysts. Tetrahedron Lett, 1992, 33 (45): 6827-6830; Endura S P A Company .New Process for the Preparation of 5-AlkyIbenzo[1,3]Dioxoles from 4-Vinylcyclohexenes.Ital, IT1299067.2000), but this method needs to add isobutyraldehyde in the system, and the cost is very high

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] In the first step, add 242 ml of 1.775 mol / L sodium hypochlorite solution into a 2000 ml three-neck flask, cool in an ice-water bath, keep the solution temperature at 2-3°C, and add 25 ml of 4-vinylcyclohexene under vigorous stirring. Keep stirring vigorously, add 484 ml of 0.5 mol / L sulfuric acid dropwise, complete the dropwise addition within 40 minutes, continue the reaction for 5 minutes to complete the reaction, and keep the temperature below 10°C during this process.

[0015] In the second step, keep stirring vigorously, the temperature is less than 10°C, add 45 milliliters of 17% NaOH solution to the above-mentioned reaction solution, so that the Ph value of the reaction system is 9, and 20 grams of sodium sulfite solid consumes excessive sodium hypochlorite solution, and the reaction ends in 15 minutes. The product was extracted with 80 ml of dichloromethane.

[0016] In the third step, the yield of 4-vinylcyclohexene dioxide is 36.9% (calculated as 4-vinylcyclo...

Embodiment 2

[0018] In the first step, add 388ml of 1.996mol / L sodium hypochlorite solution into a 2000ml three-neck flask, cool in an ice-water bath, keep the solution temperature at 2-3°C, and add 40ml of 4-vinylcyclohexene under vigorous stirring. Keep stirring vigorously, add 898 ml of 0.5mol / L sulfuric acid dropwise, the dropwise addition is completed within 34 minutes, and continue to react for 5 minutes to complete the reaction. During this process, keep the temperature below 10°C.

[0019] In the second step, keep stirring vigorously, the temperature is less than 10°C, add 64 milliliters of 17% NaOH solution to the above reaction solution, so that the Ph value of the reaction system is 9, 30 grams of sodium sulfite solid consumes excessive sodium hypochlorite solution, and the reaction ends in 15 minutes. The product was extracted with 250 ml of dichloromethane.

[0020] In the third step, the yield of 4-vinylcyclohexene dioxide is 49.2% (calculated as 4-vinylcyclohexene) through G...

Embodiment 3

[0022] In the first step, add 480 ml of 1.76 mol / L sodium hypochlorite solution into a 10,000 ml three-neck flask, cool in an ice-water bath, maintain the solution temperature at 2-3°C, and add 50 ml of 4-vinylcyclohexene under vigorous stirring. Keep stirring vigorously, add 1350 ml of 0.5 mol / L sulfuric acid dropwise, the dropwise addition is completed within 51 minutes, and continue to react for 5 minutes to complete the reaction. During this process, keep the temperature below 10°C.

[0023] In the second step, keep stirring vigorously, the temperature is less than 10°C, add 80 milliliters of 50% NaOH solution to the above-mentioned reaction solution, so that the Ph value of the reaction system is 9.3, 45 grams of sodium sulfite solid consumes excessive sodium hypochlorite solution, and the reaction ends in 30 minutes. The product was extracted with 400 ml of dichloromethane.

[0024] In the third step, the yield of 4-vinylcyclohexene dioxide is 51.6% (calculated as 4-viny...

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 relates to a method for synthesizing dioxide 4-vinylcyclohexene, particularly to a method for synthesizing dioxide 4-vinylcyclohexene with 4-vinylcyclohexene and sodium hypochlorite as raw materials under certain conditions, belonging to the technology field of organic synthesis. The specific steps comprise reacting sodium hypochlorite solution and 4-vinylcyclohexene, adding dilute sulfuric acid, adding sodium bisulfite under basic condition, and purifying by distillation to obtain dioxide 4-vinylcyclohexene. The method has the advantages of low cost of raw materials, easily accessible raw materials, recycled solvent, low cost, mild reaction conditions, simple and rapid reaction process, remarkably improved production efficiency, and low energy consumption.

Description

technical field [0001] The invention relates to a method for synthesizing 4-vinylcyclohexene dioxide. To be precise, 4-vinylcyclohexene dioxide is synthesized under certain conditions using 4-vinylcyclohexene and sodium hypochlorite as raw materials. The method belongs to the technical field of organic synthesis. Background technique [0002] 4-vinylcyclohexene dioxide (4-vinylcyclohexene dioxide) is a colorless transparent liquid, belonging to alicyclic epoxy resin, with good weather resistance and arc resistance, high temperature resistance, ultraviolet resistance, low viscosity and good process performance specialty. It can be used to make casting plastics, composite materials, coatings, adhesives, etc. for high-voltage insulation, rocket engine casings, and transformer sealants. It can also be used as a reactive diluent and PVC stabilizer, and its application is becoming more and more extensive. (See: "Dictionary of Chemical Engineering"; Jiao Jiajun, Wu Xiaofeng. Res...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/12C07D303/04
Inventor 单永奎孟静张恒强李疆候亚伟王文娟贺峥
Owner EAST CHINA NORMAL UNIV