Preparation process of antioxidant AO3353
By making 2,2'-ethylene bis(4,6-diteopentyl)phenol and synthesizing antioxidant AO3353 by one pot method, the problems of short service life of BHT and environmental pollution are solved, and efficient and low-cost antioxidant preparation is achieved.
Patent Information
- Application Number
- CN202411683755.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-11-22
- Publication Date
- 2025-03-07
AI Technical Summary
In the prior art, the antioxidant BHT has a short service life in rubber due to its small molar weight and strong volatile properties, and its environmental pollution and threat to human health need to be found to reduce costs and environmental impacts.
By making 2,2'-ethylene bis(4,6-diteopentyl)phenol and directly synthesizing the antioxidant AO3353 by one pot method, the production cost of the antioxidant AO3353 is reduced.
The efficient preparation of the antioxidant AO3353 is achieved, which reduces production costs, and has a simple process, low energy consumption, and high purity of the generated product and is convenient to operate.
Smart Images
Figure BDA0005148961980000031 
Figure HDA0005148961990000011 
Figure HDA0005148961990000012
Abstract
Description
Technical Field
[0001] The invention relates to the technical field of organic synthesis, in particular to a preparation process of an antioxidant AO3353. Background Art
[0002] The rapid development of the synthetic rubber industry has promoted the transformation of the rubber additive industry to a large-scale industrialized production mode. The manufacture and use of such chemicals will inevitably have a negative impact on the ecological environment and human health. It is urgent to solve the pollution problem of synthetic rubber additive chemicals.
[0003] BHT is usually used as an antioxidant in butadiene rubber. Studies have shown that due to its small molar weight, strong volatility, and easy diffusion and migration from the polymer to the surface, the antioxidant in the rubber is eventually consumed. Moreover, when the antioxidant BHT enters the environment, it will threaten human health. In order to solve the above technical problems, the prior art uses antioxidant AO3353 to replace antioxidant BHT. The main raw material for the synthesis of antioxidant AO3353 is 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol, which is relatively scarce in the market, resulting in a high price for antioxidant AO3353. Summary of the invention
[0004] In order to solve the problems in the prior art, the present invention provides a preparation process of antioxidant AO3353, homemade 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol, and then directly synthesizing antioxidant AO3353 by a one-pot method, so that the cost of using antioxidant AO3353 is greatly reduced.
[0005] The preparation process of an antioxidant AO3353 provided by the present invention adopts the following technical scheme: A preparation process of antioxidant AO3353 comprises the following steps: Step 1, Synthesis of 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol Step 1.1, mixing 2,4-di-tert-amylphenol and an organic solvent, and then adding a catalyst and stirring evenly; Step 1.2, adding a toluene solution containing triacetaldehyde to step 1.1 at a temperature of 80-100° C., and then reacting for 3-6 hours; Step 2, Synthesis of Antioxidant AO3353 After the reaction of step 2.1 and step 1.2 is completed, the temperature is raised to 115-120°C, the organic solvent is distilled off, and then the reaction temperature is lowered to 25-35°C, and then triethylamine is added and stirred; Step 2.2, prepare a mixture of acryloyl chloride and an organic solvent, add the mixture dropwise into step 2.1 at a temperature of 30-60°C, react for 2-4 hours, then add water to recover triethylamine, distill under reduced pressure to remove the solvent, crystallize, and filter to obtain antioxidant AO3353.
[0006] Preferably, the weight ratio of 2,4-di-tert-amylphenol to paraldehyde is 9:(1-2).
[0007] Preferably, the weight ratio of paraldehyde to toluene in step 1.2 is (1-2):5.
[0008] Preferably, the amount of the catalyst in step 1.1 is 1.67-3.89% by weight of 2,4-di-tert-amylphenol.
[0009] Preferably, the catalyst in step 1.1 comprises Span 80 and p-toluenesulfonic acid in a weight ratio of 1:1.
[0010] Preferably, in step 1.1, Span 80 is first added and stirred for 10-15 minutes, and then p-toluenesulfonic acid is added and stirred evenly.
[0011] Preferably, the weight ratio of triethylamine to 2,4-di-tert-amylphenol is (11-13):18.
[0012] Preferably, the weight ratio of acryloyl chloride to organic solvent in step 2.2 is (35-40):50.
[0013] In summary, the present invention has the following beneficial effects: 1. In the present application, in step 1, 2,4-di-tert-amylphenol and an organic solvent are mixed, a catalyst is added, and a toluene solution containing tri-acetaldehyde is added dropwise at a temperature of 80-100° C., followed by reaction for 3-6 hours. It can be seen that the synthesis process of 2,2'-ethylenebis(4,6-di-tert-amyl)phenol in the present application is simple, with low energy consumption, and the generated 2,2'-ethylenebis(4,6-di-tert-amyl)phenol has high purity.
[0014] 2. After synthesizing 2'-ethylenebis(4,6-di-tert-pentyl)phenol, the present application distills out the organic solvent, directly adds the acid-binding agent triethylamine after the reaction temperature is lowered, and then drops the mixed solution containing acryloyl chloride, reacts for 2-4 hours, generates the antioxidant AO3353 and hydrochloric acid, and the hydrochloric acid reacts with the acid-binding agent triethylamine to generate triethylamine hydrochloride, which is dissolved in water and separated in the form of triethylamine hydrochloride, and then the organic solvent is removed by reduced pressure distillation, and then the antioxidant AO3353 is obtained by crystallization and filtration. The whole production process has low energy consumption, convenient operation, high recovery rate of triethylamine, and effectively reduces production costs. BRIEF DESCRIPTION OF THE DRAWINGS
[0015] Figure 1 It is the TGA spectrum of antioxidant AO3353 in Example 1.
[0016] Figure 2 It is the DSC spectrum of antioxidant AO3353 in Example 1.
[0017] Figure 3 It is the NMR spectrum of antioxidant AO3353 in Example 1.
[0018] Figure 4 It is the infrared spectrum of antioxidant AO3353 in Example 1. DETAILED DESCRIPTION
[0019] The present invention is further described in detail below with reference to the embodiments.
[0020] The raw materials used in the examples of this application are all commercially available.
[0021] A preparation process of antioxidant AO3353 comprises the following steps: Step 1, Synthesis of 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol Step 1.1, mixing 2,4-di-tert-amylphenol and an organic solvent, and then adding a catalyst and stirring evenly; Step 1.2, adding a toluene solution containing triacetaldehyde to step 1.1 at a temperature of 80-100° C., and then reacting for 3-6 hours; Step 2, Synthesis of Antioxidant AO3353 After the reaction of step 2.1 and step 1.2 is completed, the temperature is raised to 115-120°C, the organic solvent is distilled off, and then the reaction temperature is lowered to 25-35°C, and then triethylamine is added and stirred; Step 2.2, prepare a mixture of acryloyl chloride and an organic solvent, add the mixture dropwise into step 2.1 at a temperature of 30-60°C, react for 2-4 hours, then add water to recover triethylamine, distill under reduced pressure to remove the solvent, crystallize, and filter to obtain antioxidant AO3353.
[0022] Preferably, the weight ratio of 2,4-di-tert-amylphenol to paraldehyde is 9:(1-2).
[0023] Preferably, the weight ratio of paraldehyde to toluene in step 1.2 is (1-2):5.
[0024] Preferably, the amount of the catalyst in step 1.1 is 1.67-3.89% by weight of 2,4-di-tert-amylphenol.
[0025] Preferably, the catalyst in step 1.1 comprises Span 80 and p-toluenesulfonic acid in a weight ratio of 1:1.
[0026] Preferably, in step 1.1, Span 80 is first added and stirred for 10-15 minutes, and then p-toluenesulfonic acid is added and stirred evenly.
[0027] Preferably, the weight ratio of triethylamine to 2,4-di-tert-amylphenol is (11-13):18.
[0028] Preferably, the weight ratio of acryloyl chloride to organic solvent in step 2.2 is (35-40):50.
[0029] The synthesis process of the antioxidant AO3353 of the present application is as follows: The specific preparation process is described in the examples.
[0030] Example 1 A preparation process of antioxidant AO3353 comprises the following steps: Step 1, Synthesis of 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol Step 1.1, add 180g of 2,4-di-tert-amylphenol and 400g of organic solvent toluene into a reaction bottle and stir and mix for 10 minutes, then add a catalyst and stir evenly, the amount of the catalyst added is 1.67% of the weight of 2,4-di-tert-amylphenol, wherein the catalyst uses p-toluenesulfonic acid; Step 1.2, adding 20 g of paraldehyde to 100 g of toluene and stirring to obtain a mixed solution A (i.e., the weight ratio of paraldehyde to toluene is 1:5), and adding the mixed solution A dropwise to the mixture obtained in step 1.1 at a temperature of 800° C., and then reacting for 3 hours, i.e., the weight ratio of 2,4-di-tert-amylphenol to paraldehyde is 9:1; Step 2, Synthesis of Antioxidant AO3353 After the reaction of step 2.1 and step 1.2 is completed, the temperature in the reaction flask is raised to 115° C., toluene is distilled to remove water, and the distillation is stopped until there is no water in the distilled toluene. Then, the reaction temperature is lowered to 25° C., 110 g of triethylamine (i.e., the weight ratio of triethylamine to 2,4-di-tert-amylphenol is 11:18) is added to the reaction flask, and stirred for 30 minutes; Step 2.2, 35g of acryloyl chloride and 50g of organic solvent toluene are mixed to obtain a mixed solution B (the weight ratio of acryloyl chloride and toluene is 35:50), and the mixed solution B is added dropwise to the mixture obtained in step 2.1, and the addition is completed at a temperature of 30°C, and the reaction is carried out for 2h. After the reaction is completed, 180g of water is added to the reaction bottle, and the water is stirred for 25 minutes after the addition of water, and then allowed to stand for 1 hour to separate the aqueous phase, which is the triethylamine to be recovered. The remaining reaction solution is then distilled under reduced pressure at an internal temperature of less than 80°C to evaporate the toluene solvent, and toluene is recovered. After the toluene is completely recovered, 280g of ethanol is added to the reaction bottle, and the product in the reaction bottle is completely dissolved by heating and reflux, and then the temperature is reduced to 5-10°C. Crystallization, insulation for 1h, and filtration to obtain antioxidant AO3353, the purity of antioxidant AO3353 is 98.2%, the yield is 91.3%, and the spectrum of antioxidant AO3353 is referenced Figure 1-Figure 4 .
[0031] Example 2 A preparation process of antioxidant AO3353 comprises the following steps: Step 1, Synthesis of 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol Step 1.1, add 180g of 2,4-di-tert-amylphenol and 500g of organic solvent toluene into a reaction bottle and stir and mix for 10 minutes, then add a catalyst and stir evenly, the amount of the catalyst added is 2.67% of the weight of 2,4-di-tert-amylphenol, wherein the catalyst uses p-toluenesulfonic acid; Step 1.2, adding 30 g of paraldehyde to 100 g of toluene, stirring and mixing to obtain a mixed solution A (i.e., the weight ratio of paraldehyde to toluene is 1.5:5), adding the mixed solution A dropwise to the mixture obtained in step 1.1 at a temperature of 90° C., and then reacting for 4.5 hours, i.e., the weight ratio of 2,4-di-tert-amylphenol to paraldehyde is 9:1.5; Step 2, Synthesis of Antioxidant AO3353 After the reaction of step 2.1 and step 1.2 is completed, the temperature in the reaction flask is raised to 115° C., toluene is distilled to remove water, and the distillation is stopped until there is no water in the distilled toluene. Then, the reaction temperature is lowered to 25° C., 110 g of triethylamine (i.e., the weight ratio of triethylamine to 2,4-di-tert-amylphenol is 11:18) is added to the reaction flask, and stirred for 30 minutes; Step 2.2, 35g of acryloyl chloride and 50g of organic solvent toluene are mixed to obtain a mixed solution B (the weight ratio of acryloyl chloride and toluene is 35:50), and the mixed solution B is added dropwise to the mixture obtained in step 2.1 at a temperature of 30°C. The reaction is carried out for 2h. After the reaction is completed, 180g of water is added to the reaction bottle, and the water is stirred for 25 minutes after the water is added. Then, it is allowed to stand for 1 hour to separate the aqueous phase, which is the triethylamine to be recovered. The remaining reaction solution is then distilled under reduced pressure at an internal temperature of less than 80°C to evaporate the toluene solvent and recover the toluene. After the toluene is completely recovered, 280g of ethanol is added to the reaction bottle, and the product in the reaction bottle is completely dissolved by heating and reflux. Then, the temperature is lowered and crystallized. When the temperature drops to 5-10°C, it is kept warm for 1h and filtered to obtain antioxidant AO3353. The purity of antioxidant AO3353 is 98.5% and the yield is 92.2%.
[0032] Example 3 A preparation process of antioxidant AO3353 comprises the following steps: Step 1, Synthesis of 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol Step 1.1, add 180g of 2,4-di-tert-amylphenol and 600g of organic solvent toluene into a reaction bottle and stir and mix for 10 minutes, then add a catalyst and stir evenly, the amount of the catalyst added is 1.67% of the weight of 2,4-di-tert-amylphenol, wherein the catalyst uses p-toluenesulfonic acid; Step 1.2, adding 40 g of paraldehyde to 100 g of toluene, stirring and mixing to obtain a mixed solution A (i.e., the weight ratio of paraldehyde to toluene is 2:5), and adding the mixed solution A dropwise to the mixture obtained in step 1.1 at a temperature of 100° C., and then reacting for 6 hours, i.e., the weight ratio of 2,4-di-tert-amylphenol to paraldehyde is 9:2; Step 2, Synthesis of Antioxidant AO3353 After the reaction of step 2.1 and step 1.2 is completed, the temperature in the reaction flask is raised to 115° C., toluene is distilled to remove water, and the distillation is stopped until there is no water in the distilled toluene. Then, the reaction temperature is lowered to 25° C., 110 g of triethylamine (i.e., the weight ratio of triethylamine to 2,4-di-tert-amylphenol is 11:18) is added to the reaction flask, and stirred for 30 minutes; Step 2.2, 35g of acryloyl chloride and 50g of organic solvent toluene are mixed to obtain a mixed solution B (the weight ratio of acryloyl chloride and toluene is 35:50), and the mixed solution B is added dropwise to the mixture obtained in step 2.1 at a temperature of 30°C. The reaction is carried out for 2h. After the reaction is completed, 180g of water is added to the reaction bottle, and the water is stirred for 25 minutes after the water is added. Then, it is allowed to stand for 1 hour to separate the aqueous phase, which is the triethylamine to be recovered. The remaining reaction solution is then distilled under reduced pressure at an internal temperature of less than 80°C to evaporate the toluene solvent and recover the toluene. After the toluene is completely recovered, 280g of ethanol is added to the reaction bottle, and the product in the reaction bottle is completely dissolved by heating and reflux. Then, the temperature is lowered and crystallized. When the temperature drops to 5-10°C, it is kept warm for 1h and filtered to obtain antioxidant AO3353. The purity of antioxidant AO3353 is 98.5% and the yield is 91.9%.
[0033] Example 4 A preparation process of antioxidant AO3353 comprises the following steps: Step 1, Synthesis of 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol Step 1.1, add 180g of 2,4-di-tert-amylphenol and 500g of organic solvent toluene into a reaction bottle and stir and mix for 10 minutes, then add a catalyst and stir evenly, the amount of the catalyst added is 2.67% of the weight of 2,4-di-tert-amylphenol, wherein the catalyst uses p-toluenesulfonic acid; Step 1.2, adding 30 g of paraldehyde to 100 g of toluene, stirring and mixing to obtain a mixed solution A (i.e., the weight ratio of paraldehyde to toluene is 1.5:5), adding the mixed solution A dropwise to the mixture obtained in step 1.1 at a temperature of 90° C., and then reacting for 4.5 hours, i.e., the weight ratio of 2,4-di-tert-amylphenol to paraldehyde is 9:1.5; Step 2, Synthesis of Antioxidant AO3353 After the reaction of step 2.1 and step 1.2 is completed, the temperature in the reaction flask is raised to 120° C., toluene is distilled to remove water, and the distillation is stopped until there is no water in the distilled toluene. Then, the reaction temperature is lowered to 30° C., 120 g of triethylamine (i.e., the weight ratio of triethylamine to 2,4-di-tert-amylphenol is 12:18) is added to the reaction flask, and stirred for 30 minutes; Step 2.2, 38g of acryloyl chloride and 50g of organic solvent toluene are mixed to obtain a mixed solution B (the weight ratio of acryloyl chloride and toluene is 38:50), and the mixed solution B is added dropwise to the mixture obtained in step 2.1 at a temperature of 50°C. The reaction is carried out for 3h. After the reaction is completed, 250g of water is added to the reaction bottle, and the water is stirred for 25 minutes after the water is added. Then, it is allowed to stand for 1.5 hours to separate the aqueous phase, which is the triethylamine to be recovered. The remaining reaction solution is then distilled under reduced pressure at an internal temperature of less than 80°C to evaporate the toluene solvent, and toluene is recovered. After the toluene is completely recovered, 340g of ethanol is added to the reaction bottle, and the product in the reaction bottle is completely dissolved by heating and reflux. Then, the temperature is lowered and crystallized. When the temperature drops to 5-10°C, it is kept warm for 1h and filtered to obtain antioxidant AO3353. The purity of antioxidant AO3353 is 99.1% and the yield is 92.9%.
[0034] Example 5 A preparation process of antioxidant AO3353 comprises the following steps: Step 1, Synthesis of 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol Step 1.1, add 180g of 2,4-di-tert-amylphenol and 500g of organic solvent toluene into a reaction bottle and stir and mix for 10 minutes, then add a catalyst and stir evenly, the amount of the catalyst added is 2.67% of the weight of 2,4-di-tert-amylphenol, wherein the catalyst uses p-toluenesulfonic acid; Step 1.2, adding 30 g of paraldehyde to 100 g of toluene, stirring and mixing to obtain a mixed solution A (i.e., the weight ratio of paraldehyde to toluene is 1.5:5), adding the mixed solution A dropwise to the mixture obtained in step 1.1 at a temperature of 90° C., and then reacting for 4.5 hours, i.e., the weight ratio of 2,4-di-tert-amylphenol to paraldehyde is 9:1.5; Step 2, Synthesis of Antioxidant AO3353 After the reaction of step 2.1 and step 1.2 is completed, the temperature in the reaction flask is raised to 120° C., toluene is distilled to remove water, and the distillation is stopped until there is no water in the distilled toluene. Then, the reaction temperature is lowered to 35° C., 130 g of triethylamine (i.e., the weight ratio of triethylamine to 2,4-di-tert-amylphenol is 13:18) is added to the reaction flask, and stirred for 30 minutes; Step 2.2, 40g of acryloyl chloride and 50g of organic solvent toluene are mixed to obtain a mixed solution B (the weight ratio of acryloyl chloride and toluene is 40:50), and the mixed solution B is added dropwise to the mixture obtained in step 2.1 at a temperature of 50°C. The reaction is carried out for 4h. After the reaction is completed, 300g of water is added to the reaction bottle, and the mixture is stirred for 25 minutes after the addition of water. The mixture is allowed to stand for 2 hours to separate the aqueous phase, which is the triethylamine to be recovered. The remaining reaction solution is then distilled under reduced pressure at an internal temperature of less than 80°C to remove the toluene solvent and toluene is recovered. After the toluene is completely recovered, 400g of ethanol is added to the reaction bottle, and the reaction bottle is heated to reflux to dissolve all the products in the reaction bottle. Then, the temperature is lowered to crystallize. When the temperature drops to 5-10°C, the mixture is kept warm for 1h and filtered to obtain antioxidant AO3353. The purity of antioxidant AO3353 is 99.1% and the yield is 92.8%.
[0035] Example 6 A preparation process of antioxidant AO3353 comprises the following steps: Step 1, Synthesis of 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol Step 1.1, add 180g of 2,4-di-tert-amylphenol and 500g of organic solvent toluene into a reaction bottle and stir for 10 minutes, then add a catalyst and stir evenly, the amount of the catalyst added is 2.67% of the weight of 2,4-di-tert-amylphenol, wherein the catalyst is a mixture of p-toluenesulfonic acid and Span 80 in a weight ratio of 1:1; Step 1.2, adding 30 g of paraldehyde to 100 g of toluene, stirring and mixing to obtain a mixed solution A (i.e., the weight ratio of paraldehyde to toluene is 1.5:5), adding the mixed solution A dropwise to the mixture obtained in step 1.1 at a temperature of 90° C., and then reacting for 4.5 hours, i.e., the weight ratio of 2,4-di-tert-amylphenol to paraldehyde is 9:1.5; Step 2, Synthesis of Antioxidant AO3353 After the reaction of step 2.1 and step 1.2 is completed, the temperature in the reaction flask is raised to 120° C., toluene is distilled to remove water, and the distillation is stopped until there is no water in the distilled toluene. Then, the reaction temperature is lowered to 30° C., 120 g of triethylamine (i.e., the weight ratio of triethylamine to 2,4-di-tert-amylphenol is 12:18) is added to the reaction flask, and stirred for 30 minutes; Step 2.2, 38g of acryloyl chloride and 50g of organic solvent toluene are mixed to obtain a mixed solution B (the weight ratio of acryloyl chloride and toluene is 38:50), and the mixed solution B is added dropwise to the mixture obtained in step 2.1 at a temperature of 50°C. The reaction is carried out for 3h. After the reaction is completed, 250g of water is added to the reaction bottle, and the water is stirred for 25 minutes after the water is added. Then, it is allowed to stand for 1.5 hours to separate the aqueous phase, which is the triethylamine to be recovered. The remaining reaction solution is then distilled under reduced pressure at an internal temperature of less than 80°C to evaporate the toluene solvent, and toluene is recovered. After the toluene is completely recovered, 340g of ethanol is added to the reaction bottle, and the product in the reaction bottle is completely dissolved by heating and reflux. Then, the temperature is lowered and crystallized. When the temperature drops to 5-10°C, it is kept warm for 1h and filtered to obtain antioxidant AO3353. The purity of antioxidant AO3353 is 99.3%, and the yield is 93.7%.
[0036] Example 7 A preparation process of antioxidant AO3353 comprises the following steps: Step 1, Synthesis of 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol Step 1.1, add 180g of 2,4-di-tert-amylphenol and 500g of organic solvent toluene into a reaction bottle and stir for 10 minutes, then add the catalyst Span 80 and stir for 10-15 minutes, then add p-toluenesulfonic acid and stir evenly, the total amount of catalyst added is 2.67% of the weight of 2,4-di-tert-amylphenol, wherein the weight ratio of the catalyst to p-toluenesulfonic acid and Span 80 is 1:1; Step 1.2, adding 30 g of paraldehyde to 100 g of toluene, stirring and mixing to obtain a mixed solution A (i.e., the weight ratio of paraldehyde to toluene is 1.5:5), adding the mixed solution A dropwise to the mixture obtained in step 1.1 at a temperature of 90° C., and then reacting for 4.5 hours, i.e., the weight ratio of 2,4-di-tert-amylphenol to paraldehyde is 9:1.5; Step 2, Synthesis of Antioxidant AO3353 After the reaction of step 2.1 and step 1.2 is completed, the temperature in the reaction flask is raised to 120° C., toluene is distilled to remove water, and the distillation is stopped until there is no water in the distilled toluene. Then, the reaction temperature is lowered to 30° C., 120 g of triethylamine (i.e., the weight ratio of triethylamine to 2,4-di-tert-amylphenol is 12:18) is added to the reaction flask, and stirred for 30 minutes; Step 2.2, 38g of acryloyl chloride and 50g of organic solvent toluene are mixed to obtain a mixed solution B (the weight ratio of acryloyl chloride and toluene is 38:50), and the mixed solution B is added dropwise to the mixture obtained in step 2.1 at a temperature of 50°C. The reaction is carried out for 3h. After the reaction is completed, 250g of water is added to the reaction bottle, and the water is stirred for 25 minutes after the water is added. Then, it is allowed to stand for 1.5 hours to separate the aqueous phase, which is the triethylamine to be recovered. The remaining reaction solution is then distilled under reduced pressure at an internal temperature of less than 80°C to evaporate the toluene solvent, and toluene is recovered. After the toluene is completely recovered, 340g of ethanol is added to the reaction bottle, and the product in the reaction bottle is completely dissolved by heating and reflux. Then, the temperature is lowered and crystallized. When the temperature drops to 5-10°C, it is kept warm for 1h and filtered to obtain antioxidant AO3353. The purity of antioxidant AO3353 is 99.4% and the yield is 93.9%.
[0037] The embodiments of this specific implementation method are all preferred embodiments of the present invention, and are not intended to limit the protection scope of the present invention. Therefore, any equivalent changes made based on the structure, shape, and principle of the present invention should be included in the protection scope of the present invention.
Claims
1. A preparation process of antioxidant AO3353, characterized in that: The steps include: Step 1. Synthesis of 2,2'-ethylenebis(4,6-di-tert-pentyl)phenol Step 1.1, mixing 2,4-di-tert-amylphenol and an organic solvent, and then adding a catalyst and stirring evenly; Step 1.2, adding a toluene solution containing triacetaldehyde to step 1.1 at a temperature of 80-100° C., and then reacting for 3-6 hours; Step 2, Synthesis of Antioxidant AO3353 After the reaction of step 2.1 and step 1.2 is completed, the temperature is raised to 115-120°C, the organic solvent is distilled off, and then the reaction temperature is lowered to 25-35°C, and then triethylamine is added and stirred; Step 2.2, prepare a mixture of acryloyl chloride and an organic solvent, add the mixture dropwise into step 2.1 at a temperature of 30-60°C, react for 2-4 hours, then add water to recover triethylamine, distill under reduced pressure to remove the solvent, crystallize, and filter to obtain antioxidant AO3353.
2. The preparation process of an antioxidant AO3353 according to claim 1, characterized in that: The weight ratio of the 2,4-di-tert-amylphenol to paraldehyde is 9:(1-2).
3. The preparation process of an antioxidant AO3353 according to claim 1, characterized in that: The weight ratio of triacetaldehyde to toluene in step 1.2 is (1-2):
5.
4. The preparation process of an antioxidant AO3353 according to claim 1, characterized in that: The amount of the catalyst in step 1.1 is 1.67-3.89% of the weight of 2,4-di-tert-amylphenol.
5. The preparation process of an antioxidant AO3353 according to claim 1, characterized in that: The catalyst in step 1.1 includes Span 80 and p-toluenesulfonic acid in a weight ratio of 1:
1.
6. The preparation process of an antioxidant AO3353 according to claim 5, characterized in that: In the step 1.1, first add Span 80 and stir for 10-15 minutes, then add p-toluenesulfonic acid and stir evenly.
7. The preparation process of an antioxidant AO3353 according to claim 1, characterized in that: The weight ratio of the triethylamine to 2,4-di-tert-amylphenol is (11-13):
18.
8. The preparation process of an antioxidant AO3353 according to claim 1, characterized in that: The weight ratio of acryloyl chloride to the organic solvent in step 2.2 is (35-40):50.