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

Integration method for preparing o-methyl allyloxyphenol

A technology for substituted allyloxyphenol and methallyl chloride is applied in the integrated field of producing o-methallyloxyphenol, and can solve the problems of difficulty, high separation difficulty, low yield of monoether, and the like, Achieve the effect of reducing the formation of by-products, shortening the reaction time, and improving the reaction efficiency

Inactive Publication Date: 2008-07-09
XIANGTAN UNIV
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is the low yield of monoether and high consumption of methallyl chloride
In Chinese patent 86102956 embodiment 1A, the mol ratio of pyrocatechol and methallyl chloride is 1: 0.6, and implementation result shows that the selectivity of reaction is 95.6%, and the conversion ratio of pyrocatechol is 45.8%, There is a large amount of catechol that needs to be recovered, and at the same time, the patent does not propose a recovery method and recovery efficiency for unreacted catechol
Therefore, in the reaction with catechol and methallyl chloride as raw materials, it is difficult to obtain high conversion rate and selectivity of catechol at the same time.
At the same time, because the nature of the by-products produced is close to that of o-methallyloxyphenol, the separation is relatively difficult, thus affecting the quality of the product to a certain extent
Even if the by-products are finally separated at the cost of sacrificing the product yield, the by-products are difficult to degrade and cause major environmental problems.

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

[0021] Embodiment 1: in a 500ml glass reactor with magnetic stirring equipped with stirring, thermometer, condenser, add ethylene glycol monomethyl ether 300g, pyrocatechol 55.0g (0.5mol), sodium carbonate 31.8g. After stirring and raising the temperature to 90°C, start to add 54.3g (0.6mol) of methallyl chloride dropwise. The dropwise addition time is 1 hour. After the dropwise addition, react at 90°C for 2 hours (including the dropwise addition time) Stop the reaction, cool the reactant to 20°C, filter to remove the generated solid sodium chloride, and wash the filter cake twice with 100g ethylene glycol monomethyl ether, and mix the washing liquid with the filtered mother liquor. Analysis by high-performance liquid chromatography showed that there were 66.68 g of o-methallyloxyphenol and 8.8 g of catechol in the mixed solution, the conversion rate of catechol was 84.0%, and the selectivity was 96.81%. Then, under the vacuum degree of 600-720mmHg, the ethylene glycol monomet...

Embodiment 2

[0022] Example 2: Repeat the reaction of Example 1, precipitation and solution preparation after precipitation, except that 80.0 g of degassed distilled water is divided into 30 g, 30 g, and 20 g for three extractions. Each extraction was well stirred at 20°C for 0.5 hours, then the solution was poured into a separatory funnel and allowed to stand for 1.5 hours. The water layer is collected and mixed each time, and the mixed water layer and the oil layer are analyzed by high-performance liquid chromatography. The weight percentage of catechol in the oil layer is 0.35%, and o-methallyloxyphenol is not detected in the water layer. .

Embodiment 3

[0023] Embodiment 3: add ethylene glycol monomethyl ether 1650g, catechol 275.0g (2.5mol), sodium carbonate 127.2g, carbonic acid Sodium hydrogen 8.4g. Stir and heat up to 100°C and start to add 339.38g (3.75mol) of methallyl chloride dropwise. The dropwise addition time is 1 hour, and then react at 100°C after the dropwise addition is completed, and stop after 1.8 hours (including the dropwise addition time) For reaction, the temperature of the reactant was lowered to 20°C, and the generated solid sodium chloride was removed by filtration, and the filter cake was washed twice with 500 g of ethylene glycol monomethyl ether, and the washing liquid was mixed with the filtered mother liquor. According to high-performance liquid chromatography analysis, there were 302.89 g of o-methallyloxyphenol and 68.75 g of catechol in the mixed solution, the conversion rate of catechol was 75.0%, and the selectivity was 98.5%. Then remove the ethylene glycol monomethyl ether in the mixed liq...

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 discloses an integrated process for preparing monoether. Pyrocatechol is in conversion reaction with methallyl chloride in reaction solvent and conversion rate of the pyrocatechol is controlled between 60-85%. Reaction solution is mixed with nonaqueous solvent to form a solution after being removed from the reaction solvent. Extracting agent is used to extract pyrocatechol which are not reacted completely in the solution to recycle, and extraction raffinate of monoether containing reaction products is obtained. The invention largely improves yield coefficient calculated by the pyrocatechol, and simultaneously decreases the loss of methylallyl chloride.

Description

technical field [0001] The invention relates to an integrated method for producing o-methallyloxyphenol by using catechol and methallyl chloride as raw materials. Background technique [0002] O-methallyloxyphenol synthesized from catechol and methallyl chloride is an important intermediate for the production of furanol. Furanol is an important intermediate of many pesticides, such as carbofuran, carbosulfan, carbosulfan, and furosecarb. [0003] Many patents have been reported on the synthesis process of o-methallyloxyphenol. Most of the patents use an excess of methallyl chloride, and select the optimal process to improve its selectivity under the condition that the conversion of catechol is as complete as possible. As in Example 1 of US Patent 4,982,012, the molar ratio of catechol and methallyl chloride is 1:12.2, the conversion rate of catechol is 100%, and the yield of monoether is 58%. The disadvantage of this method is the low yield of monoether and the high consu...

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): C07C43/23C07C41/01
CPCY02P20/10
Inventor 罗和安蒋彪孔祥云
Owner XIANGTAN UNIV
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