Method for catalytically synthesizing 3,4'-dichlorodiphenyl ether by using microwaves

A technology of dichlorodiphenyl ether and microwave catalysis, applied in 3 fields, can solve the problems of Ullmann's application limitations, harsh reaction conditions, long reaction time, etc., and achieve the effect of easy operation, less side reactions and fast reaction

Active Publication Date: 2015-12-30
HUANGSHAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the Ullmann reaction is widely used, the general yield of this type of reaction is not high and the reaction conditions are relatively harsh. Most of them need to be reacted under the conditions of high temperature and strong alkali for a long time, which greatly limits the application of Ullmann.
[0005] However, some new techniques and methods have been applied to this reaction, such as the use of ultrasound assistance or the use of more selective reagents, but the yield of these methods is still not high

Method used

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  • Method for catalytically synthesizing 3,4'-dichlorodiphenyl ether by using microwaves
  • Method for catalytically synthesizing 3,4'-dichlorodiphenyl ether by using microwaves
  • Method for catalytically synthesizing 3,4'-dichlorodiphenyl ether by using microwaves

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] First prepare the organic solvent, the specific method is as follows:

[0026] (11) In a 100mL three-necked flask equipped with a reflux condenser, add 0.1mol of 1-methylimidazole, 0.1mol of bromobutane and 0.1mol of KPF 6 , stirred and reacted at 80°C for 3h;

[0027] (12) Cool to room temperature after the reaction, add 20-50mL of water, stir well and let it stand to separate the water phase;

[0028] (13) The separated ionic liquid is then repeatedly washed with distilled water until no halogen ions are detected with silver nitrate in the washing water;

[0029] (14) Vacuum drying at 120° C. for 4 hours to obtain an oily ionic liquid;

[0030] (15) Mix the ionic liquid and dipropylene glycol dimethyl ether in a mass ratio of 1:1 to 100 to obtain an organic solvent.

[0031] The ionic liquid in this example and dipropylene glycol dimethyl ether were mixed at a mass ratio of 1:1 to prepare an organic solvent.

[0032] Present embodiment prepares 3, the method for 4...

Embodiment 2

[0036] The ionic liquid of this example and dipropylene glycol methyl ethyl ether were mixed at a mass ratio of 1:20 to prepare an organic solvent.

[0037] Present embodiment prepares 3, the method for 4'-dichlorodiphenyl ether is as follows:

[0038] (1) m-dichlorobenzene, p-chlorophenol, alkali and organic solvent are mixed, add copper salt simultaneously as catalyzer; Described m-dichlorobenzene: p-chlorophenol: potassium carbonate alkali: the mol ratio of cuprous chloride salt is 6:1:1.2:0.01, the organic solvent accounts for 10% of the total material mass ratio;

[0039] (2) Under microwave catalysis, the above mixture was stirred and reacted for 2 hours at a power of 500W, and the reaction temperature was 60-110° C. under normal pressure. Stand to cool, filter, and rectify the filtrate under reduced pressure to collect a colorless transparent liquid, with a conversion rate of 99% and a yield of 93%.

Embodiment 3

[0041] The ionic liquid of this example and dipropylene glycol methyl propyl ether were mixed at a mass ratio of 1:100 to prepare an organic solvent.

[0042] Present embodiment prepares 3, the method for 4'-dichlorodiphenyl ether is as follows:

[0043] (1) m-dichlorobenzene, p-chlorophenol, sodium hydroxide and organic solvent are mixed, and copper acetate is added as a catalyst; the m-dichlorobenzene: p-chlorophenol: alkali: the molar ratio of copper salt is 6:1 : 2: 0.1, the organic solvent accounts for 20% of the total material mass ratio;

[0044] (2) Under microwave catalysis, the above mixture was stirred and reacted for 2 hours at a power of 1000W, and the reaction temperature was 60-130° C. under normal pressure. Stand to cool, filter, and rectify the filtrate under reduced pressure to collect a colorless transparent liquid, with a conversion rate of 97% and a yield of 90%.

[0045] Other implementations are the same as in Example 1.

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Abstract

The invention discloses a method for catalytically synthesizing 3,4'-dichlorodiphenyl ether by using microwaves, which comprises the following steps: mixing m-dichlorobenzene, parachlorophenol, an alkali and an organic solvent, and meanwhile, adding a copper salt as a catalyst, wherein the m-dichlorobenzene:parachlorophenol:alkali:copper salt mole ratio is (1-10):(1-10):(1-2):(0.001-0.1), and the organic solvent accounts for 5-20 wt% of the total materials; and under the catalytic actions of microwaves with the power of 200-1000W, stirring the mixture to react at 60-130 DEG C under atmospheric pressure for 1-3 hours. The microwave-organic solvent combination is utilized to catalytically synthesize the 3,4'-dichlorodiphenyl ether, so that the reaction temperature is lowered. The reaction selectivity is 96%, and the yield can reach 93%. Meanwhile, the catalyst can be recycled. The microwave-assisted synthesis has the characteristics of high reaction speed, high yield, high safety, environment friendliness, fewer side reactions and the like, is easy to operate, enhances the production efficiency, and lowers the production cost.

Description

technical field [0001] The present invention relates to a method for synthesizing 3,4'-dichlorodiphenyl ether, in particular to a method for utilizing microwave catalysis to synthesize 3,4'-dichlorodiphenyl ether. Background technique [0002] In 1960, Rohm & Haas first developed diaryl ether insecticides. In 1968, Itaya introduced a diaryl ether structure into the pyrethroid alcohol part, which greatly improved the photostability and biological activity of pyrethroids. The development boom of diaryl ether pesticides. Introducing a diaryl ether structure into a pesticide molecule can significantly improve the physical and chemical properties and biological activity of the pesticide, mainly in terms of improving photostability, biological activity, reducing toxicity to mammals, and expanding the spectrum of biological activity. With its excellent physical and chemical properties and biological activity, diaryl ethers are widely used in pyrethroids, organophosphorus, carbamat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/16C07C43/29
CPCY02P20/584C07C41/16C07C43/29
Inventor 崔秀云
Owner HUANGSHAN UNIV
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