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Preparation method and application of thiomethylphenol derivatives based on dual catalytic system

A technology of thiomethylphenol and derivatives, which is applied in the field of preparation of thiomethylphenol derivatives based on a dual-catalysis system, can solve the problems of difficult acquisition or preparation of catalysts, difficulty in adapting to industrial production, and excessive generation of "three wastes", achieving The effect of controlling pollutant discharge, easy access, and reducing pollutant discharge

Active Publication Date: 2019-06-11
JIANGSU FEIYA CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the processes mentioned in these documents have some shortcomings, such as many side reactions, difficulty in obtaining or preparing catalysts, large amount of raw materials, complicated post-treatment, and many "three wastes", etc., which are difficult to adapt to industrial production

Method used

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  • Preparation method and application of thiomethylphenol derivatives based on dual catalytic system
  • Preparation method and application of thiomethylphenol derivatives based on dual catalytic system
  • Preparation method and application of thiomethylphenol derivatives based on dual catalytic system

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preparation example Construction

[0018] One aspect of the present invention provides a method for the preparation of thiomethylphenol derivatives based on a dual catalyst system, which may include: reacting phenol, aldehyde and mercaptan in the presence of a porous material as a catalyst and an amine, After post-treatment to obtain sulfur methyl phenol derivatives.

[0019] In some embodiments, the preparation method specifically includes: mixing phenol, aldehyde, mercaptan, solvent that may or may not be added, porous material, and amine, reacting in a closed environment, and then post-processing to obtain Thiomethylphenol derivatives.

[0020] Wherein, the structure of the thiomethylphenol derivative is shown in the following formula (I):

[0021]

[0022] where R 1 , R 2 , R 3 Respectively represent H, C1~C20 straight chain or branched alkyl or benzene ring substituents or alkyl or aryl containing O, S, N, P and / or Si, R 4 Represents a C1-C20 straight-chain or branched alkyl group or a benzene ring...

Embodiment 1

[0052] Example 1 Dissolve 2.0-2.5g of 2,6-di-tert-butylphenol, 0.5-1.0g of paraformaldehyde, 1.0-1.5g of methyl thioglycolate, 50-100mg of diethylamine and 1-3g of montmorillonite in Add about 5mL of DMF into a thick-walled pressure-resistant glass bottle with a magnet, and react for 3-8 hours at a reaction temperature of 50-110°C. After the reaction is complete, cool the reaction mixture to room temperature and filter with suction Isolate the catalyst to obtain the reaction crude product solution, and then remove the solvent and amine under reduced pressure to obtain the target product (3,5-di-tert-butyl-4-hydroxyl-)methyl benzyl mercaptoacetate, and its characterization data are as follows : 1 HNMR (CDCl 3 ):7.11(s,2H,C 6 h 2 ), 5.17(s,1H,Ph-OH),3.76(s,2H,PhCH 2 S),3.73(s,3H,-OCH 3 ),3.12(s,2H,PhCH 2 SCH 2 ),1.44(s,18H,C(CH 3 ) 3 ). Present embodiment product yield is more than 90% on average, and preferred product yield is greater than 95%, and product purity is g...

Embodiment 2

[0053] Example 2 Dissolve 1.0-1.5g of 2,6-dimethylphenol, 1.5-2.0g of formaldehyde solution (37%), 1.5-2.0g of n-octyl mercaptan, 50-100mg of dibutylamine and 1-2g of zeolite Add about 5mL DMSO into a thick-walled pressure-resistant glass bottle with a magnet, and react at a reaction temperature of 140-200°C for 1-5 hours. After the reaction, cool the reaction mixture to room temperature and pump The catalyst is separated by filtration to obtain a crude reaction product solution, and the target product can be obtained by removing the solvent under reduced pressure. The product yield is greater than 90%, and the product purity is greater than 95%.

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Abstract

The invention discloses a dual catalytic system based sulfur methyl phenol derivative preparation method and application. The preparation method includes: phenol, aldehyde and mercaptan undergo a reaction with the existence of porous material and amine as catalyst, and then the sulfur methyl phenol derivative is obtained through the post process. The preparation method adopts catalytic reaction of dual catalyst, on the one hand, the catalysts have wide source, easy access without beforehand synthesis and low cost. On the other hand, the catalytic efficiency is high with high production yield and purity (both are over 95%), resultant of reaction and catalysts are easy in separation, and thereby the process after reaction is simplified greatly. Meanwhile, the preparation method has simple operation and easy control method without any by-product, the post-process operation is also very simple, the production does not need to be washed accordingly waste water is not produced. By using the preparation method which is a green and environment-friendly technology, pollutant discharge can be controlled and reduced greatly.

Description

technical field [0001] The invention relates to a preparation method of thiomethylphenol derivatives, in particular to a preparation method and application of thiomethylphenol derivatives based on a dual catalyst system. Background technique [0002] Lubricating oils are mostly composed of base oils and additives. Lubricating oil additives are special chemical substances added to the base oil to make the lubricating oil acquire some new characteristics or improve some existing characteristics of the lubricating oil. For example, during the long-term storage and use of automobile engine oil (that is, automobile engine lubricating oil), it will inevitably come into contact with air, and then react with oxygen in the air to cause oxidation, especially when lubricated under high temperature and metal catalysis. The hydrocarbons in the oil will be converted into various oxidation products, including acidic substances, deposits, sludge, etc., which will seriously affect the norma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C323/52C07C323/16B01J31/26B01J31/02
Inventor 俞莎莎王立敏郑健马玉杰曾红玲刘升高
Owner JIANGSU FEIYA CHEM IND
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