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A kind of efficient and continuous synthesis method and device of p-chlorophenyl tert-butyl ether

A technology of chlorophenyl tert-butyl ether and a synthesis method, which is applied in chemical instruments and methods, ether preparation, ether preparation by addition of unsaturated compounds, etc., can solve the problem of low single-pass reaction rate between raw materials and protective groups, and limitation of industrial scale production. , the difficulty of recycling p-chlorophenol, etc., to achieve the effect of being conducive to large-scale industrial production, improving the total conversion rate, and improving environmental protection characteristics

Active Publication Date: 2021-06-18
HENGHE MATERIALS & SCI TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be known by querying the public literature that the protection of hydroxyl groups with groups such as tert-butyl, allyl, benzyl, and silyl ether groups is a common organic synthesis process; Among them, the one-way reaction rate of raw materials and protecting groups is low, the reaction time is long, and the recovery of p-chlorophenol is difficult, all of which limit industrial scale production. At the same time, a large amount of oily and acidic wastewater is produced during the process, causing environmental hazards

Method used

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  • A kind of efficient and continuous synthesis method and device of p-chlorophenyl tert-butyl ether
  • A kind of efficient and continuous synthesis method and device of p-chlorophenyl tert-butyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) Evenly mix p-chlorophenol and toluene in a molar ratio of 1:1.1 and then continuously send them into the agitated etherification reaction kettle R101, and load the activated clay with AlCl 3 Catalyst with N 2 Continuously put into etherification reactor R101 as a carrier gas, and at the same time, continuously put in isobutylene with a molar ratio of 1:1.2 to p-chlorophenol for reaction; the reaction temperature is 15°C, and the reaction residence time is 3h; activated clay supports AlCl 3 The consumption of catalyst is 0.75wt% of p-chlorophenol quality;

[0033] (2) The continuously discharged reaction solution enters the first flash tank V101 after being heated to 90°C. The operating pressure of the first flash tank V101 is 75kPa. After compressed by the compressor, it is mixed with fresh isobutene raw materials and recycled, and the condensed components are returned to the first flash tank V101, and the bottom material of the first flash tank V101 is pumped to t...

Embodiment 2～8

[0038] Examples 2-8 and Comparative Examples 1-2 all adopt activated clay with 0.75 wt% p-chlorophenol raw material to load AlCl 3Catalyst carries out the etherification reaction of step (1), and raw material molar proportion, reaction temperature, residence time are not identical, and test is to the impact of etherification reaction conversion rate, and result is as follows:

[0039]

[0040] From Examples 2 to 3, it can be seen that when the amount of isobutylene in the polymerization raw material is slightly more, the conversion rate of the etherification reaction will be significantly improved; from Examples 4 to 7, it can be seen that prolonging the reaction time has a lower impact on the conversion rate, and increasing the reaction temperature p-Chlorophenol etherification conversion rate is adversely affected; From Example 6, Example 8 and Comparative Examples 1 to 2, it can be seen that controlling the appropriate p-Chlorophenol and isobutylene molar ratio in the raw...

Embodiment 9～12

[0042] Embodiments 9 to 12 limit the molar ratio of raw materials: (p-chlorophenol: isobutylene: toluene) = 1: 1.2: 1, the reaction temperature is 15 ° C, and the reaction time is 3.5 hours. Different catalyst consumption and prefabricated AlCl 3 The impact of the concentration of the exchange agent solution on the conversion rate of the etherification reaction, the results are as follows:

[0043] serial number AlCl 3 Solution concentration, %

[0044] Prefabricated AlCl 3 The solvent of the catalyst exchanger solution can be methanol, ethanol or a mixed solution of the two. From the above examples, it can be known that when the concentration of the prefabricated exchanger solution is too low, the content of the supported catalyst will be reduced, thereby affecting the conversion rate of the etherification reaction; but when the concentration of the prefabricated solution is ≥ 30%, its concentration has little effect on the final conversion rate . Etherificati...

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Abstract

The invention relates to a high-efficiency and continuous synthesis method and device of p-chlorophenyl tert-butyl ether, comprising: mixing p-chlorophenol and toluene and continuously feeding them into a stirred etherification reaction kettle, and loading activated clay with AlCl 3 The catalyst is continuously put into the reactor, and isobutylene is continuously put into the reaction at the same time; the continuously discharged reaction liquid enters the flash tank after being heated to 50-70 °C, and the material at the bottom of the tank is separated from the reaction liquid and the slurry catalyst by a cyclone separator; the reaction liquid High-purity p-chlorophenyl tert-butyl ether can be obtained by alkaline washing, neutralization, water washing, and flash evaporation. The process of the present invention has the advantages of high efficiency and continuous, high conversion rate of raw materials, small environmental impact, and is beneficial to large-scale industrial production. The key intermediate of Lohr et al.

Description

technical field [0001] The invention belongs to the field of pharmaceutical intermediates, in particular to a high-efficiency and continuous synthesis method and device of p-chlorophenyl tert-butyl ether. Background technique [0002] The p-chlorophenyl tert-butyl ether synthesized with p-chlorophenol as the starting raw material can prepare 4-(2'-methoxyethyl)phenol, which is used in many raw materials such as metoprolol, premedolol, Key intermediates of Talol, Metoprolol succinate, etc. The protection of the phenolic hydroxyl group of p-chlorophenol generally adopts tert-butyl or benzyl methods, such as patent CN200410065416.8, which uses p-chlorophenol as a raw material and reacts with isobutylene under acid catalysis to obtain p-chlorophenyl tert-butyl ether; CN200610023436 discloses a A kind of p-chlorophenol or p-bromophenol is used as the starting material, under the catalysis of concentrated sulfuric acid, reacts with methyl, benzyl or tert-butyl to protect the phen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/06C07C43/225B01J27/125
CPCB01J27/125C07C41/06C07C43/225
Inventor 王斌孙向东
Owner HENGHE MATERIALS & SCI TECH CO LTD
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