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Method for synthesizing beta-(3,5-di-tert-butyl-4-hydroxyphenyl)methyl propionate

A technology of di-tert-butylphenol and hydroxyphenyl, which is applied in the field of synthesis of intermediate beta-methyl propionate, can solve the problems of increasing production cost, increasing cost, intensifying side reactions, etc., and improving product quality and yield , the effect of saving production costs and reducing reaction time

Active Publication Date: 2011-05-18
营口风光新材料股份有限公司
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AI Technical Summary

Problems solved by technology

[0004] However, the synthesis of the intermediate β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate methyl ester is relatively complicated, and the reaction cycle is long, and the control is not good. The reaction product is easily oxidized, thereby affecting the next step. reaction
The main problems existing in the existing synthetic method are: 1. solvent has been added in the addition reaction process, which increases the cost for the reaction, and the solvent recovery is difficult, which easily causes environmental pollution
② The cost of the catalyst used is high, such as potassium tert-butoxide, which increases the production cost
3. Due to the limitation of catalyst activity conditions, the reaction temperature is controlled between 80-130°C. Those skilled in the art know that methyl acrylate is prone to self-polymerization to form dimers or multimers. This dimer and 2, 6-Di-tert-butylphenol reacts to form a diester, which increases by-products. As the temperature rises, the reaction speed will increase, but when the temperature rises to a certain value, the side reactions such as p-phenol and p-quinone will be intensified, thus affecting The quality and yield of intermediate β-(3,5-di-tert-butyl-4-hydroxyphenyl) methyl propionate, and further affect the quality and yield of follow-up transesterification and antioxidant 1010 products
④In order to fully react 2,6-di-tert-butylphenol in the reversible reaction during the reaction, an excess of methyl acrylate is often used, and the excess is usually a minimum of 1.08:1 [molar ratio], which undoubtedly increases the occurrence of side reactions Possibility and production cost, and affect product purity and final yield

Method used

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  • Method for synthesizing beta-(3,5-di-tert-butyl-4-hydroxyphenyl)methyl propionate
  • Method for synthesizing beta-(3,5-di-tert-butyl-4-hydroxyphenyl)methyl propionate

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Embodiment 1

[0017] To the airtight with reflux condenser, mechanical stirring, trap, nitrogen gas line, vacuum line and inserted into the bottom of the reaction kettle, such as figure 1 with figure 2 Add 309 g (1.5 mol) of 2,6-di-tert-butylphenol into the 1-liter stainless steel reaction kettle of the circular dropper shown (number 1 in the figure is the drop hole), vacuumize, replace with nitrogen for more than 3 times, and give Heat the reactor to 55~60°C, continue vacuuming, add 3.71g (0.033mol, about 0.6% of the weight of 2,6-di-tert-butylphenol) 50% KOH aqueous solution under negative pressure, and start Stir, then continue to heat up to 90-115 ℃, remove the reaction system and the water generated by the reaction of the catalyst and 2.6-di-tert-butylphenol (subject to the fact that the water does not flow out) is collected in the cold trap, and the obtained Cool down the temperature of the slurry to 95°C, and start to add 131.6g (1.53mol) methyl acrylate dropwise into the reactor. ...

Embodiment 2

[0020] Add 400 g (1.94 mol) of 2,6- Di-tert-butylphenol, vacuumize, replace with nitrogen more than 3 times, heat the reactor to between 55°C and 60°C, continue vacuuming, and add 5g (0.045mol, weight about 2,6-di 0.625% of tert-butylphenol) 50% KOH aqueous solution, start stirring, and then continue to heat up to 90-110 ℃, remove the reaction system and the water generated by the reaction of the catalyst and 2.6-di-tert-butylphenol (water does not flow out ) collected in the cold trap, cooled the slurry obtained in the reactor to 95°C, and began to add 175g (2.03 mol) of methyl acrylate dropwise to the reactor, and controlled the rate of addition, and the dripping was completed within about 30 minutes. During the exothermic reaction, the temperature is controlled between 95-105°C. After the dropwise addition is completed, nitrogen gas is filled to a pressure of 0.4MP, and the temperature is kept between 95-105°C for 3 hours. Cool the system down to about 80°C, vacuum the sys...

Embodiment 3

[0023]Add 309 g (1.5 mol) of 2,6- Di-tert-butylphenol, vacuumize, replace with nitrogen more than 3 times, heat the reactor to 55~60°C, continue vacuuming, and add 6.18g (0.055mol, weight about 2,6- 1% of di-tert-butylphenol) 50% KOH aqueous solution, start stirring, and then continue to heat up to 90-115 ℃, remove the reaction system and the water generated by the reaction of the catalyst and 2.6-di-tert-butylphenol (water will come out flow) into the cold trap, lower the temperature of the slurry obtained in the reactor to 90°C, and start to add 135g (1.57mol) methyl acrylate dropwise to the reactor, and control the dropping rate, and the drop will be completed within about 30 minutes During the exothermic reaction, the temperature is controlled between 95-105°C during the dropwise addition. After the dropwise addition is completed, nitrogen gas is filled to a pressure of 0.6MP, and the temperature is kept between 90-100°C for 3 hours. Cool the reaction system to about 80°C...

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Abstract

The invention relates to a method for synthesizing beta-(3,5-di-tert-butyl-4-hydroxyphenyl)methyl propionate. The technical scheme comprises the following steps of: adding 2,6-di-tert-butyl phenol into a reaction kettle, vacuumizing, displacing hydrogen for more than three times, raising the temperature to be between 55 and 60 DEG C, adding a catalyst, stirring, continuously raising the temperature to be between 90 and 115 DEG C, and dehydrating to obtain slurry; reducing the temperature of the obtained slurry to be between 90 and 97 DEG C, dripping methyl acrylate into the reaction kettle by using an annular dropper which is inserted into the bottom of the reaction kettle, controlling the temperature to be between 95 and 105 DEG C, filling the nitrogen until pressure is between 0.4 and 0.6MPa after dripping is finished, controlling the temperature to be between 95 and 105 DEG C, preserving heat and reacting for 1.5 to 2.5 hours; and reducing the temperature to be between 75 and 85 DEG C, vacuumizing, adding organic acid, reacting for 10 to 20 minutes, filtering, and purifying to obtain a product. By the method, the reaction temperature can be reduced, reaction time is shortened, side reaction is reduced, and the quality and yield of the product are improved.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing an intermediate β-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate methyl ester for producing hindered phenolic antioxidants. Background technique [0002] Antioxidants can delay or prevent the oxidation or automatic oxidation process of synthetic materials, thereby prolonging the service life of materials, and their applications involve almost all polymer products. Antioxidants are generally used in small amounts, and have little effect on the mechanical properties of polymers after being added. Polyphenol antioxidants 1010 and 1076 are currently the leading products of relatively good antioxidants, and their consumption accounts for about 40% of the total consumption of antioxidants. [0003] Methyl β-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate is a good hindered phenolic inhibitor, which is suitable for polyethylene, polypropylene, poly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/612C07C67/303
Inventor 王磊
Owner 营口风光新材料股份有限公司
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