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Synthetic method of 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione compound

A technology of dimethylbenzyl, synthesis method, applied in 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5- In the field of synthesis of triazine-2,4,6(1H,3H,5H)-triketone compounds, it can solve the problems of many by-products, high industrial energy consumption, and long reaction time, and achieve less by-products, low industrial energy consumption, The effect of short reaction times

Inactive Publication Date: 2015-04-29
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has a particularly long reaction time, high energy consumption in industrial applications, and more by-products of the reaction

Method used

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  • Synthetic method of 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione compound
  • Synthetic method of 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione compound
  • Synthetic method of 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0027] Embodiment 11, the synthesis of 4-tert-butyl-2,6-dimethyl-3-hydroxyl benzyl chloride

[0028] Add 49g of 32% hydrochloric acid and 49g of 2-tert-butyl-4,6-dimethylphenol at one time into the reaction flask, add 13.1g of paraformaldehyde under stirring, then heat up to 37°C, and keep it warm at this temperature for 2 After 1 hour, TLC followed the reaction to the end. After the heat preservation was finished, 17.3 g of phosphorus trichloride was started to be added dropwise, and the temperature of the kettle was controlled to 40° C., and the drop was completed in about 1 hour, and kept at this temperature for about 4 hours, and the TLC tracking reaction ended.

[0029] After the reaction, add 50g of toluene, stir for 15min and then let stand for 20min, separate the lower aqueous phase, wash the organic phase with saturated brine at 30°C (20ml x 2 times), evaporate the toluene under reduced pressure.

[0030] Cool to 35-40°C, and drop DMF under control at this temperatur...

Embodiment 21

[0031] Example 21, 3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H, Synthesis of 5H)-triketone

[0032] Add 39g of DMF and 10.5g of cyanuric acid into the reaction bottle at one time, add 40.5g of triethylamine under stirring, and then heat up to 90°C, add the pre-prepared 1,4-tert-butyl-2,6- A mixture of 62.3 g of dimethyl-3-hydroxybenzyl chloride and 32.7 g of DMF was dropped into it. There is slight reflux during the process, and the temperature of the kettle will rise slowly, and it is required not to exceed 102°C, and the dripping will be completed in about 11 / 2 hours. Then incubate and react at 100-120° C. for about 5 hours, and follow up the reaction by TLC to complete.

[0033] After the reaction, the salt was removed by filtration at room temperature, rinsed with a small amount of DMF, and dried by filtration. Recover the solvent under reduced pressure, add 115g methanol, distill 60g under normal pressure reflux, drop to 1-2°C and kee...

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Abstract

The invention discloses a synthetic method of a 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione compound, wherein the synthetic method comprises the steps of adding DMF, cyanuric acid and triethylamine into a reaction kettle, then heating up to 80-100 DEG C, next dropwise adding a mixed solution of 4-tert-butyl-2,6-dimethyl-3-hydroxy benzyl chloride and DMF, after reaction, filtering, evaporating to dryness, dissolving with methanol and precipitating, and thus obtaining the synthetic product. The synthetic method has the advantages of simple operation, short reaction time, few by-products, and high product yield.

Description

technical field [0001] The present invention relates to a production method of chemical products, in particular to a 1,3,5-tri(4-tert-butyl-3-hydroxyl-2,6-dimethylbenzyl)-1,3,5 -Technological synthesis method of triazine-2,4,6(1H,3H,5H)-trione (antioxidant TH-1790). Background technique [0002] 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H) -Triketone, the commercial name is antioxidant TH-1790, its traditional preparation method is: add the mixed solution of 4-tert-butyl-2,6-dimethyl-3-hydroxybenzyl chloride and DMF at one time in the reaction kettle , triethylamine and cyanuric acid, stirred and reacted at 40 degrees for 18 hours. The reaction time of this method is particularly long, the industrial energy consumption is high, and the by-products of the reaction are also many. Contents of the invention [0003] In order to overcome the above-mentioned deficiencies in the prior art, the present invention provides a new preparation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/30
CPCC07D251/32
Inventor 陈达洪镛裕刘乃兴苏云清石婷婷
Owner EAST CHINA NORMAL UNIV
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