Preparation method of 2,4-di(n-octyl thiomethylene)-6-methylphenol

A technology of n-octylsulfamethylene and cresol, which is applied in the field of preparation of phenolic antioxidants, can solve problems such as long reaction time, unfavorable reaction, and reduced yield, so as to simplify the production operation process and improve the reaction rate. Efficiency, the effect of controlling emissions

Active Publication Date: 2021-01-15
JIANGSU JIYI NEW MATERIAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When using the first two methods to prepare, the raw materials 4,6-chloromethyl-o-cresol and 4,6-hydroxymethyl-o-cresol need to be synthesized respectively, and the synthesis steps are many, the reaction time is longer, and the yield is lower.
The traditional catalytic synthesis of alkylphenol, formaldehyde, and octyl mercaptan requires a 33% dimethylamine aqueous solution as a catalyst. Studies have shown that the water contained in the dimethylamine solution is not conducive to the occurrence of the reaction, resulting in a decrease in yield
Also use the dimethylamine ethanol of massfraction 38% as catalyst in the prior art, yield reaches 90%, but catalyst preparation process is loaded down with trivial details (Zhou Qin etc. novel antioxidant 2.4-(n-octylsulfamethylene)- Synthesis of 6-hydroxyphenol, Chemical World, 2007, 48(2):107-109)

Method used

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  • Preparation method of 2,4-di(n-octyl thiomethylene)-6-methylphenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Replace the reaction flask with stirrer, condenser and thermometer with nitrogen, add 34.7g o-cresol, 89.5g n-octyl mercaptan and 36.5g paraformaldehyde therein, and add 40% dimethylamine aqueous solution 340g and 8.5 g sodium didodecyl diphenyl ether disulfonate, under stirring conditions, raise the temperature to 100°C to reflux, the reaction solution forms a uniform emulsion state, and continue to react for 5 hours. After the reaction is finished, the temperature of the reaction system is lowered by 5° C., and left to stand for 10 hours, the crystallization of the antioxidant 1520 2,4-bis(n-octylthiomethylene)-6-methylphenol is cooled in the reaction system, and the obtained White powdery product, kept at a low temperature of 5-10°C, filtered to separate the solid powder, washed with ethanol solution, and dried to obtain the target compound 2,4-bis(n-octylthiomethylene)-6-methylphenol 127.7 g, its reaction yield is 97.1%, and the product purity is 98.8%.

Embodiment 2

[0020] Replace the reaction flask with stirrer, condenser and thermometer with nitrogen, add 34.7g o-cresol, 135g n-octyl mercaptan and 36.5g paraformaldehyde therein, and add 40% dimethylamine aqueous solution 340g and 8.5g Didodecyl diphenyl ether sodium disulfonate, under the condition of stirring, raise the temperature to 100°C to reflux, the reaction liquid forms a uniform emulsion state, and continue to react for 6 hours. After the reaction is finished, the temperature of the reaction system is lowered by 5° C., and left to stand for 12 hours, the crystallization of the antioxidant 1520 2,4-bis(n-octylthiomethylene)-6-methylphenol is cooled in the reaction system, and the obtained White powdery product, kept at a low temperature of 5-10°C, filtered to separate the solid powder, washed with ethanol solution, and dried to obtain the target compound 2,4-bis(n-octylthiomethylene)-6-methylphenol 127.0 g, its reaction yield is 96.5%, and the product purity is 98.0%.

Embodiment 3

[0022] Replace the reaction flask with stirrer, condenser and thermometer with nitrogen, add 34.8g o-cresol, 89.5g n-octyl mercaptan and 46.2g paraformaldehyde therein, and add 280g and 7g of 33% dimethylamine aqueous solution Didodecyl diphenyl ether sodium disulfonate, under the condition of stirring, raise the temperature to 100°C to reflux, the reaction liquid forms a uniform emulsion state, and continue to react for 4 hours. After the reaction is finished, the temperature of the reaction system is lowered by 10° C., and left to stand for 10 hours, the crystallization of the antioxidant 1520 2,4-bis(n-octylthiomethylene)-6-methylphenol that is cooled down is generated in the reaction system to obtain White powdery product, kept at a low temperature of 5-10°C, filtered to separate the solid powder, washed with ethanol solution, and dried to obtain the target compound 2,4-bis(n-octylthiomethylene)-6-methylphenol 126.2 g, its reaction yield is 96.0%, and the product purity is...

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Abstract

The invention provides a preparation method of an antioxidant 1520 2,4-di(n-octyl thiomethylene)-6-methylphenol. The method comprises the following steps: reacting o-cresol, n-octyl mercaptan and paraformaldehyde, adding a dimethylamine water solution and an emulsifier to the reaction solution to form a uniform emulsion state, cooling the reaction system, standing, and generating the antioxidant 1520 2,4-di(n-octyl thiomethylene)-6-methylphenol crystal in the reaction system to obtain the white powdery product. According to the present invention, with the method, the reaction conditions are mild, the product purity and the yield are excellent, the post-treatment is simple, and the cost is low.

Description

technical field [0001] The invention relates to a preparation method of a phenolic antioxidant, in particular to a preparation method of antioxidant 1520 2,4-bis(n-octylthiomethylene)-6-methylphenol. Background technique [0002] Phenolic antioxidants are a very important class of primary antioxidants, which can prevent polymer materials from losing strength and toughness due to oxidative degradation, and are widely used in high molecular polymers such as rubber, plastics and adhesives. 2,4-bis(n-octylthiomethylene)-6-methylphenol, also known as antioxidant 1520, is a hindered phenolic antioxidant containing a thiol alkyl group, which has thioether and Hindered phenol has two functional groups, which have the advantages of low toxicity, low color pollution and strong compatibility, so its application is becoming more and more extensive. [0003] The chemical structural formula of 2,4-bis(n-octylthiomethylene)-6-methylphenol (antioxidant 1520) is as follows: [0004] [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C323/16
CPCC07C319/14C07C323/16
Inventor 郭骄阳赵崇鑫
Owner JIANGSU JIYI NEW MATERIAL CO LTD
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