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Synthesis method of antioxidant 1790

A synthesis method and antioxidant technology, which is applied in the synthesis field of antioxidant 1790, can solve the problems of high cost, low utilization rate of raw materials, heavy pollution, etc., and achieve the effects of increasing yield, convenient post-processing, and reducing production cost

Inactive Publication Date: 2017-05-24
兰州精细化工有限责任公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of this invention is to provide a kind of synthetic method of antioxidant 1790, to solve the problems of large pollution, low utilization rate of raw materials and high cost in existing methods

Method used

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  • Synthesis method of antioxidant 1790
  • Synthesis method of antioxidant 1790
  • Synthesis method of antioxidant 1790

Examples

Experimental program
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Effect test

Embodiment 1

[0036] In the three-necked flask, add 2,4-dimethyl-6 tert-butylphenol (1.78g, 0.01mol) and concentrated hydrochloric acid 1.78g, stir, then add paraformaldehyde (0.6g, 0.02mol), and heat up to 38°C , heat preservation reaction for 50 hours, TLC detection raw material still remains. After the reaction, the reaction system was extracted three times with ethyl acetate, the organic layer was collected, dried over anhydrous sodium sulfate, and distilled under reduced pressure to obtain a light yellow oil, the product 4-tert-butyl-3-hydroxy-2,6-dimethyl Benzyl alcohol was directly used in the preparation of 4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl chloride.

Embodiment 2-- Embodiment 4

[0038] Change respectively the temperature described in embodiment 1 and the add-on of concentrated hydrochloric acid, all the other steps and process conditions are identical with embodiment 1, specifically see table 3. As can be seen from Table 3, the result of embodiment 4 is the best, being the best embodiment.

[0039] table 3

[0040] Numbering Concentrated hydrochloric acid (g) temperature(°C) result Example 1 1.78 38 There are surplus raw materials Example 2 1.78 40 There are surplus raw materials Example 3 1.78 42 There are surplus raw materials Example 4 3.56 40 Raw material reaction is complete

[0041] The second big step, the embodiment of preparing intermediate 4-tert-butyl-3-hydroxyl-2,6-dimethylbenzyl chloride:

Embodiment 5

[0043]In the three-necked flask, add 4-tert-butyl-3-hydroxyl-2,6-dimethylbenzyl alcohol (2.08g, 0.01mol), triethylamine (1.21g, 0.012mol) and benzene obtained in Example 4 Thionyl chloride (1.78g, 0.015mol) was added dropwise to 25mL with stirring at 0°C. When the concentration of the raw material was no longer changed by TLC, the reaction was quenched by adding water and extracted three times with ethyl acetate. The organic layer was collected and distilled under reduced pressure to obtain a yellow The oil was dried over anhydrous sodium sulfate, and crystallized with ethyl acetate and petroleum ether as the crystallization solvent to obtain 1.16 g of off-white needle crystals, with a yield of 51%. The proton nuclear magnetic resonance spectrum verified that the substance was the target product 4-tert-butyl-3-hydroxyl-2,6-dimethylbenzyl chloride. Spectral data: 1H NMR (400MHz, CDCl3) δ7.19(s, 1H), 4.73-4.65(m, 2H), 2.59(s, 3H), 2.46(s, 3H), 1.50(s, 9H) .

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Abstract

The invention discloses a synthesis method of an antioxidant 1790 and belongs to chemical field. By adoption of the synthesis method, the problems of serious pollution, low raw material utilization ratio and high cost in the existing method are solved. The synthesis method is implemented by three steps of: (1) preparation of 4-tert-butyl-3-hydroxyl-2,6-dimethyl benzyl alcohol, wherein 2,4-dimethyl-6-tert-butyl phenol, concentrated hydrochloric acid and paraformaldehyde are stirred at the temperature of 40 DEG C and return for 50 hours to obtain 4-tert-butyl-3-hydroxyl-2,6-dimethyl benzyl alcohol, and the product does not need to be purified; (2) preparation of 4-tert-butyl-3-hydroxyl-2,6-dimethyl benzyl chloride, wherein hydroxyl groups of the 4-tert-butyl-3-hydroxyl-2,6-dimethyl benzyl alcohol are chloro-substituted by thionyl chloride to obtain the 4-tert-butyl-3-hydroxyl-2,6-dimethyl benzyl chloride, the product can be obtained by crystallization of methyl benzene and methyl alcohol, and after removal of a solvent, the crystallized mother liquor can be continuously used as a raw material; and (3) preparation of a 1790 product. The synthesis method disclosed by the invention has the advantages that the production cost is effectively reduced, the steps are simple and easy to operate, and the generated waste water is less, so that the industrial production is easy.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a synthesis method of antioxidant 1790. Background technique [0002] The chemical name of antioxidant 1790 is 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4, 6-(1H,3H,5H)-trione, the structural formula is as follows: [0003] [0004] Antioxidant 1790 is a hindered phenolic antioxidant, which has the characteristics of high resistance to boiling water and washing liquid, no pollution, no coloring, etc. It can be applied to nylon series, polyester, ABS, polyolefin pipes, agricultural film, household appliances, styrene plastics and polyester. [0005] At present, the method for preparing antioxidant 1790 is mainly divided into two steps. In the process of preparing the intermediate 4-tert-butyl-3-hydroxyl-2,6-dimethylbenzyl chloride in the first step, there is always moisture This leads to the decomposition of the chlorinated reagent an...

Claims

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Application Information

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IPC IPC(8): C07D251/32
CPCC07D251/32
Inventor 王晓霞刘荣何开宇刘云利刘生丽
Owner 兰州精细化工有限责任公司
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