Method for preparing 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate

A technology of dimethylbenzyl and isocyanurate, applied in the direction of organic chemistry, can solve the problems of increased production cost, uneconomical, high processing cost, etc., and achieve the goal of simplifying the production operation process, reducing costs, and reducing production costs Effect

Active Publication Date: 2013-12-04
RIANLON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] This method has used organic bases such as triethylamine of higher price, has produced a large amount of waste water that contains triethylamine hydrochloride, although can reclaim organic bases such as triethylamine by common method, process is complicated, in order to reach It is an uneconomical method to apply circularly to require high quality and high processing costs, which will lead to an increase in production costs.

Method used

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  • Method for preparing 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate
  • Method for preparing 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate
  • Method for preparing 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a 500ml four-neck flask equipped with a stirrer, reflux condenser, and thermometer, add 19.8g (0.1mol) of trisodium cyanurate, 4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl Chlorine 71g (0.31mol), N,N-dimethylformamide 200ml and phase transfer catalyst 1g, nitrogen protection was continuously passed through, stirring was raised to 120°C, and the reaction was kept for 14h. Then cool down to 50-60°C and filter, the filtrate is distilled under reduced pressure of 0.005-0.015MPa to remove N,N-dimethylformamide, add 200ml of toluene and 100ml of water to the residue, stir and heat up until the material is completely dissolved, static Separate the water phase, distill the remaining water and about 160ml of toluene from the organic phase, slowly add 150ml of methanol to the residue, dissolve the material under stirring and reflux, add 5g of activated carbon for decolorization, heat filter, cool down and crystallize, filter, rinse with methanol, and dry 54.6 g of 1,3,5-tris(4-te...

Embodiment 2

[0028] In the same four-neck flask as in Example 1, add 19.8 g (0.1 mol) of trisodium cyanurate, 71 g (0.31 mol) of 4-tert-butyl-3-hydroxyl-2,6-dimethylbenzyl chloride , 200ml of N,N-dimethylacetamide and 1g of phase transfer catalyst, continuously fed with nitrogen protection, stirring and raising the temperature to 120°C, and keeping the reaction for 14h. Then cool down to 50-60°C and filter, the filtrate is distilled under reduced pressure of 0.005-0.015MPa to remove N,N-dimethylacetamide, add 200ml xylene and 100ml water to the residue, stir and heat up until the material is completely dissolved, Stand still to separate the water phase, distill the remaining water and about 150ml of xylene from the organic phase, slowly add 150ml of methanol to the residue, stir and reflux the material to dissolve, add 5g of activated carbon for decolorization, heat filter, cool down and crystallize, filter, rinse with methanol, 52.5 g of dry 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylb...

Embodiment 3

[0030] In the same four-neck flask as in Example 1, 19.8 g (0.1 mol) of trisodium cyanurate, 75.5 g (0.33 mol) of 4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl chloride were added ), N, N-dimethylformamide 200ml and a phase transfer catalyst 2g, continue to feed nitrogen protection, stir and raise the temperature to 100°C, and keep the reaction for 20h. Then cool down to 50-60°C and filter, the filtrate is distilled under reduced pressure of 0.005-0.015MPa to remove N,N-dimethylformamide, add 200ml of toluene and 100ml of water to the residue, stir and heat up until the material is completely dissolved, static Separate the water phase, distill the remaining water and about 160ml of toluene from the organic phase, slowly add 150ml of methanol to the residue, dissolve the material under stirring and reflux, add 5g of activated carbon for decolorization, cool down and crystallize, filter, rinse with methanol to obtain dry 1, 50.8 g of 3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzy...

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Abstract

The invention discloses a method for preparing 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate. The method includes the following steps: first, adding cyanuric acid trisodium salt and 4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl into a polar aprotic solvent, second, adding a phase transfer catalyst, third, heating the mixture to 100-120 DEG C and leaving the mixture to carry out thermal reaction for 8-20h under the protection of nitrogen, fourth, cooling the mixture to 50-60 DEG C and filtering out the salt, fifth, distilling off the solvent under a pressure of 0.005-0.015MPa, sixth, adding a non-polar solvent and water for solution and washing, seventh, distilling off residual water and a large part of solvent after settlement water diversion, eighth, adding methyl alcohol for dissolution, ninth, adding activated carbon for decoloration, tenth, cooling filtrate to achieve separation by crystallization after hot filtration, and eleventh, carrying out filtration to obtain the 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate. The method simplifies production operation processes and reduces cost for the treatment of three wastes greatly.

Description

technical field [0001] The invention relates to the field of polymer material additives, and relates to a preparation method of 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate. It belongs to the preparation technology of antioxidant. Background technique [0002] 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate specifically refers to the following formula (I): [0003] [0004] The above formula (I) is a high-efficiency hindered phenol primary antioxidant, which has the characteristics of no pollution and no coloring. It is suitable for polypropylene, polyethylene, polyamide, polystyrene, ABS resin, polyester, fiber resin, etc., especially Suitable for polypropylene. Only 0.02-0.1% of this product can effectively inhibit its thermo-oxidative degradation during high-temperature processing and use, and it has an excellent synergistic effect when used in combination with phosphite secondary antioxidants. [0005] The method described in...

Claims

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Application Information

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IPC IPC(8): C07D251/34
Inventor 云会霞孙春光汤翠祥李海平范小鹏彭啸徐丁
Owner RIANLON
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