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Synthesis technology for 2, 4, 6-trimethylbenzene acetyl chloride

A technology of trimethylphenylacetyl and trimethylphenylacetic acid, applied in 2 fields, can solve problems such as difficult rectification, difficult production control, ozonide explosion, etc., to achieve full reaction and avoid mutual isolation

Active Publication Date: 2012-08-15
SUQIAN COSMOS CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, these synthetic processes all have room for improvement. For example, method 1 is difficult to rectify in the subsequent treatment, and a large amount of hydrogen cyanide generated by the reaction at the same time causes a greater safety hazard; The production cost is high, and it is not suitable for industrial production; the ozonide produced in the method 3 reaction is prone to explosion, and the production is difficult to control

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] 2400mL of 37% hydrochloric acid and 486g (4mol) of mesitylene are placed in the reactor, and then 347.6g (4.4mol) of 37% formaldehyde solution is added dropwise at a temperature of 55 to 58°C. React at 75°C, check the progress of the reaction with GC, after the reaction is complete, cool the reaction solution to room temperature to obtain a solution containing 2,4,6-trimethylbenzyl chloride. Then add toluene for extraction, and obtain a toluene solution of 2,4,6-trimethylbenzyl chloride after washing, and the yield of 2,4,6-trimethylbenzyl chloride reaches about 90%.

[0064] Add 199.98g (3.96mol) of sodium cyanide into the reactor, stir to dissolve the sodium cyanide, then add 16g of phase transfer catalyst dodecyltrimethylammonium chloride and the 2,4,6-trimethylammonium obtained above The toluene solution of benzyl chloride is heated to reflux at a temperature of 68-72°C to carry out the cyanation reaction, and then the reaction is kept at this temperature for 6-7 ho...

Embodiment 2

[0069] 2400mL of 37% hydrochloric acid and 486g (4mol) of mesitylene are placed in the reactor, and then 379.2g (4.8mol) of 37% formaldehyde solution is added dropwise at a temperature of 56 to 58°C. The reaction was carried out at ℃, and the progress of the reaction was checked by GC. After the reaction was complete, the reaction solution was cooled to room temperature to obtain a solution containing 2,4,6-trimethylbenzyl chloride. Then add toluene for extraction, and obtain a toluene solution of 2,4,6-trimethylbenzyl chloride after washing.

[0070] Add 202g (4mol) of sodium cyanide into the reactor, stir to dissolve the sodium cyanide, then add 14g of phase transfer catalyst hexadecyltri-n-butylammonium bromide and the 2,4,6-trimethylammonium obtained above The toluene solution of benzyl chloride is heated to reflux at a temperature of 69-73° C. for cyanation reaction, and then kept at this temperature for 8 to 9 hours. After the reaction is completed, add water, stir and ...

Embodiment 3

[0075] 2400mL of 37% hydrochloric acid and 486g (4mol) of mesitylene are placed in the reactor, and then 363.4g (4.6mol) of 37% formaldehyde solution is added dropwise at a temperature of 55 to 57°C. The reaction was carried out at ℃, and the progress of the reaction was checked by GC. After the reaction was complete, the reaction solution was cooled to room temperature to obtain a solution containing 2,4,6-trimethylbenzyl chloride. Then add toluene for extraction, and obtain a toluene solution of 2,4,6-trimethylbenzyl chloride after washing.

[0076] Add 218.16g (4.32mol) of sodium cyanide into the reactor, stir to dissolve the sodium cyanide, then add 12g of phase transfer catalyst tetradecyltrimethylammonium chloride and the 2,4,6-trimethylammonium obtained above The toluene solution of benzyl chloride is heated to reflux at a temperature of 65-68° C. for cyanation reaction, and then the reaction is kept at this temperature for 6 to 7 hours. After the reaction is completed...

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Abstract

The invention relates to a synthesis technology for 2, 4, 6-trimethylbenzene acetyl chloride, comprising the following steps of: putting thionyl chloride, a catalyst and 2, 4, 6-trimethylbenzene acetic acid into a reaction kettle in batches, and controlling temperature to carry out reaction; and after the reaction, distilling (high vacuum) in a heating way in the reaction kettle, and acquiring a final product. The preparation method of the 2, 4, 6-trimethylbenzene acetic acid can comprise the following steps of: carrying out chloromethylation reaction by taking trimethylbenzene, formaldehyde and concentrated hydrochloric acid as raw materials, adding toluene to extract after reacting, and washing to obtain a toluene solution of 2, 4, 6-trimethyl benzyl chloride; taking the toluene solution of 2, 4, 6-trimethyl benzyl chloride and the sodium cyanide as raw materials, adding a phase transfer catalyst, reflowing in a heating way to carry out cyanation reaction, washing by adding water after reacting, distilling oil phase to recover toluene and mesitylene, and rectifying to obtain 2, 4, 6-trimethylbenzene acetonitrile; and hydrolyzing the 2, 4, 6-trimethylbenzene acetonitrile, centrifuging to obtain a 2, 4, 6-trimethylbenzeneacetic acid crude product, and optionally selecting and carrying out the aftertreatment to obtain the 2, 4, 6-trimethylbenzeneacetic acid. The content of the 2, 4, 6-trimethylbenzene acetyl chloride synthesized by the method disclosed by the invention is more than or equal to 98.0%, and the content of the 2, 4, 6-trimethylbenzene acetonitrile is less than or equal to 0.5%.

Description

technical field [0001] The invention relates to a preparation method of an organic intermediate, in particular to a synthesis process of 2,4,6-trimethylphenylacetyl chloride. Background technique [0002] 2,4,6-Trimethylphenylacetyl chloride is an intermediate in organic synthesis. The consumption in the global market is mainly concentrated in some developed countries and regions such as Europe, America, Japan, and South Korea. It is mainly used in the synthesis of organic products. , dyes also have important applications. The total annual market demand is large. The global demand for this product in 2009 was over 500 tons. For example, Chinese patent 200810060254 discloses a preparation method of spiromethimen, which uses 2,4,6-trimethylphenylacetyl chloride as the main raw material. [0003] CN101633607 A discloses a method for synthesizing fluorine-substituted naphthols, which involves subjecting fluorine-substituted phenylacetic acid to acid halide to form fluorine-su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/72C07C51/60
Inventor 沈宏宇李焕成
Owner SUQIAN COSMOS CHEM
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