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Preparation method of p-bromophenylalkyl ether

A technology of bromophenyl alkyl ether and phenyl alkyl ether, which is applied in the field of preparation of p-bromophenyl alkyl ether, can solve the problems of life safety of difficult operators, low production efficiency, unfavorable economic benefits, etc., and achieve low process pollution, Less dangerous, the effect of solving potential safety hazards

Active Publication Date: 2020-06-30
BEIJING GREENCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are following problems in the preparation method of this etherification route: the one, needs to use poisonous diethyl sulfate in the etherification process, is more dangerous, therefore exists safety problem, is difficult to guarantee the life safety of operator; A large amount of waste water will be produced, and it will cost a certain amount to treat the waste water, so the overall cost is relatively high; the third is that the amount of water used as a reaction solvent in the reaction process is very large, and the molar ratio of water to raw materials is as high as 200 times, and water occupies most of the reactor space, resulting in a very small amount of raw materials loaded in the reactor, resulting in low production efficiency
Therefore, the preparation method of this etherification route has problems such as high safety risk, high comprehensive cost, long production time, and low production efficiency, which is not conducive to the improvement of economic benefits of enterprises

Method used

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  • Preparation method of p-bromophenylalkyl ether
  • Preparation method of p-bromophenylalkyl ether
  • Preparation method of p-bromophenylalkyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation of p-bromophenetole

[0046] Add 500g of industrially pure phenetole, 507g of dichloroethane, and 883g of 45% hydrobromic acid into the reaction flask, control the temperature at -5-5°C, add 557g of 30% hydrogen peroxide dropwise, and keep stirring for 3 hours. GC detection, there are raw materials remaining, heat preservation and continue to stir for 3 hours, GC detection, the remaining raw materials are about 1%, and then heat preservation and stirring for 1 hour, GC detection, the reaction is over, liquid separation, the organic phase is adjusted to alkaline with NaOH aqueous solution, and then sulfur Wash with sodium sulfite aqueous solution, let stand, separate liquids, desolventize the organic phase, and finally carry out rectification to obtain 534.8 g of colorless to pale yellow liquid p-bromophenethyl ether, the calculated yield is 65.0%, and the purity detected by GC is 99.0% above.

Embodiment 2

[0048] Preparation of p-bromophenetole

[0049] Add 500g of industrially pure phenetole, 1kg of dichloroethane, and 883g of 45% hydrobromic acid into the reaction flask, control the temperature at -5-5°C, add 557g of 30% hydrogen peroxide dropwise, and keep stirring for 3 hours. GC detection, there are raw materials remaining, heat preservation and continue to stir for 3 hours, GC detection, the remaining raw materials are about 1%, and then heat preservation and stirring for 1 hour, GC detection, the reaction is over, liquid separation, the organic phase is adjusted to alkaline with NaOH aqueous solution, and then sulfur Wash with sodium sulfite aqueous solution, stand still, separate liquids, desolventize the organic phase, and finally carry out rectification to obtain 740.6 g of colorless to light yellow liquid p-bromophenethyl ether, the calculated yield is 90.0%, and the purity detected by GC is 99.0% above.

Embodiment 3

[0051] Preparation of p-bromophenetole

[0052] Add 500g of industrially pure phenetole, 2kg of dichloroethane, and 883g of 45% hydrobromic acid into the reaction flask, control the temperature at -5-5°C, add 557g of 30% hydrogen peroxide dropwise, and keep stirring for 3 hours. GC detection, there are raw materials remaining, heat preservation and continue to stir for 3 hours, GC detection, the remaining raw materials are about 1%, and then heat preservation and stirring for 1 hour, GC detection, the reaction is over, liquid separation, the organic phase is adjusted to alkaline with NaOH aqueous solution, and then sulfur Wash with sodium sulfite aqueous solution, stand still, separate liquids, desolventize the organic phase, and finally carry out rectification to obtain 741.6 g of colorless to light yellow liquid p-bromophenethyl ether, the calculated yield is 90.1%, and the purity detected by GC is 99.0% above.

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Abstract

The invention relates to a preparation method of p-bromophenylalkyl ether, wherein the preparation method comprises the steps: carrying out bromination reaction on phenylalkyl ether, hydrobromic acidand an oxidant in an organic solvent to prepare p-bromophenylalkyl ether. A chlorinated non-polar solvent is used as a reaction solvent, so that the para-position substitution selectivity of the bromination reaction is greatly improved, the yield of the bromination reaction is remarkably improved, p-bromophenylalkyl ether is prepared by replacing an etherification reaction route with the bromination reaction, toxic diethyl sulfate does not need to be used in the preparation process, and potential safety hazards are avoided; meanwhile, the dosage of the solvent is greatly reduced, the loading capacity of the raw materials of a reaction kettle is greatly improved, the production efficiency is greatly improved, and the production time is shortened; the post-treatment is simple, the reaction solvent can be recycled, and the comprehensive production cost is reduced; the method has the advantages of easily available raw materials, simple operation, low risk, high yield, high product purity,small pollution of the whole process, and suitableness for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of p-bromophenyl alkyl ether, which belongs to the technical field of organic synthesis. Background technique [0002] P-bromophenyl alkyl ether shown in formula (I) [0003] [0004] Among them, R is C 1-3 Alkyl hydrocarbons are an important class of raw materials for organic synthesis. For example, p-bromoanisole is an important pharmaceutical intermediate; More and more widely used in daily life, the industrial production of p-bromophenetole has great research value. [0005] At present, the preparation of p-bromophenyl ether mainly adopts the etherification route. For example, the current method of preparing p-bromophenethyl ether is to use p-bromophenol as a raw material, and obtain the product through etherification, washing and distillation. There are following problems in the preparation method of this etherification route: the one, needs to use poisonous diethyl sulfate in the etherification ...

Claims

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Application Information

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IPC IPC(8): C07C41/22C07C43/225
CPCC07C41/22C07C43/225
Inventor 宫宁瑞
Owner BEIJING GREENCHEM TECH