CN112250550A - Preparation method of antioxidant 330 - Google Patents
Preparation method of antioxidant 330 Download PDFInfo
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- CN112250550A CN112250550A CN202011236186.2A CN202011236186A CN112250550A CN 112250550 A CN112250550 A CN 112250550A CN 202011236186 A CN202011236186 A CN 202011236186A CN 112250550 A CN112250550 A CN 112250550A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
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Abstract
The invention relates to the technical field of chemical material processing, in particular to a synthesis method for preparing a hindered phenol antioxidant 330, which takes 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material, reduces the initial raw material into 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, and then condenses the 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol and mesitylene under the action of an acid catalyst to generate the antioxidant 330. In the condensation reaction process, the phase transfer catalyst polyethylene glycol is utilized to improve the catalytic effect of concentrated sulfuric acid, and the consumption of the concentrated sulfuric acid is reduced, so that the method has great industrial value. The reaction yield is high, the optimal yield can reach 95%, the purity of the obtained reduction product is high, and the post-treatment is simple in the industrial process. Therefore, the synthesis of the antioxidant 330 by using 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material and reducing the initial raw material into alcohol is a process route with great industrial value.
Description
Technical Field
The invention relates to the technical field of chemical material processing, in particular to a synthesis method for preparing a hindered phenol antioxidant 330, which takes 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material, reduces the initial raw material into 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, and then condenses the 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol and mesitylene under the action of an acid catalyst to generate the antioxidant 330.
Background
Antioxidant 330, CAS No.: 1709-70-2, the name of Chinese is 1,3, 5-trimethyl-2, 4,6- (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene, which is a high molecular weight hindered phenol antioxidant and is widely applied to polyolefin, PET, PBT, polyamide, styrene resin, polyurethane, natural rubber and other elastomer materials. The antioxidant is developed and popularized by American Shell company in 1960, has the characteristics of good compatibility with resin, extraction resistance, low volatilization, high antioxidant efficiency, good electrical insulation and the like, is particularly suitable for the processing field of products such as polyolefin pipes, injection-molded products, wires and cables and the like processed at high temperature, and has good synergistic effect with auxiliary antioxidants such as phosphite ester, thioester and the like and a carbon free radical trapping agent.
Due to such excellent properties of the antioxidant 330, a great deal of research has been conducted on its synthetic route. So far, there are many reports on the preparation process and synthesis method of antioxidant 330, and these reports are largely divided into two types: the first type uses 2, 6-di-tert-butyl phenol and formaldehyde (or paraformaldehyde) to produce 2, 6-di-tert-butyl-4-hydroxybenzyl alcohol (or 2, 6-di-tert-butyl-4-hydroxybenzyl methyl ether) under the action of a catalyst, and then the 2, 6-di-tert-butyl-4-hydroxybenzyl methyl ether and the mixture are mixed under the condition of an acid catalyst to prepare an antioxidant 330, and the research of the type mostly focuses on the selection of the catalyst in the preparation process of the 2, 6-di-tert-butyl-4-hydroxybenzyl alcohol (or 2, 6-di-tert-butyl-4-hydroxybenzyl methyl ether); the selection of acid catalyst in the latter step and during the condensation reaction of mesitylene. The second type uses 4, 6-trihalomethyl-1, 3, 5-trimethylbenzene (halogen can be chlorine and bromine) and 2, 6-di-tert-butylphenol as raw materials to prepare the antioxidant 330 under the action of an acid catalyst.
Although researchers have developed methods for synthesizing hindered phenol antioxidants 330, these methods still have many drawbacks, such as problems of reaction yield being improved, reaction process being simplified, and catalyst variety being exploited. In view of the above, the present inventors have developed a novel synthesis process of hindered phenol antioxidant 330 through research and experimental exploration of the existing literature, so as to effectively overcome the problems in the prior art, thereby satisfying the wide demand of antioxidants in the field of polymer materials, and having good industrial application potential and popularization value.
Disclosure of Invention
The invention provides 1, a preparation method of an antioxidant 330, which is characterized in that: 3, 5-di-tert-butyl-4-hydroxybenzoic acid is used as an initial raw material, 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol is prepared by reduction, and then the 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol and mesitylene are condensed to generate an antioxidant 330, wherein the chemical name of the antioxidant 330 is 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene.
In the process of reducing 3, 5-di-tert-butyl-4-hydroxybenzene alcohol by using 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material into 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, tetrahydrofuran THF is used as a solvent, and Zn (BH)4)2As a reducing agent, the reduction reaction temperature is 60-66 ℃, and the reaction time is 5-10 hours.
In the process of condensing the 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol and mesitylene to generate the antioxidant 330, dichloromethane is used as a solvent, a mixed complexing agent of a phase transfer catalyst and concentrated sulfuric acid is used, the phase transfer catalyst is a polyethylene glycol solution, the reaction temperature is 3-8 ℃, and the reaction time is 2-4 hours.
In the process of condensing the 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol and mesitylene to generate the antioxidant 330, the phase transfer catalyst is a polyethylene glycol series with the molecular weight of 200-1000.
The acid catalyst is a mixed complexing agent of a phase transfer catalyst and concentrated sulfuric acid, and the mass concentration of the concentrated sulfuric acid is 85%; mass ratio mConcentrated sulfuric acid：mPolyethylene glycol=100：3.0。
The acid catalysis is a mixed complexing agent of a phase transfer catalyst and concentrated sulfuric acid, the using amount of the mixed complexing agent is 2.5 times of that of mesitylene, and m isComplexing agent：mMesitylene=2.5：1.0。
Adding mesitylene and dichloromethane into a glass reactor, carrying out ice-water bath at 3-8 ℃, dropwise adding the solution, continuing to react for 3 hours after dropwise adding for 1 hour, detecting a liquid phase until the raw materials disappear, and stopping the reaction; and (3) transferring the reaction solution to a separating funnel, standing for layering, removing a lower sulfuric acid phase, washing an upper organic phase to be neutral by using a sodium bicarbonate solution, distilling and recovering dichloromethane, and recrystallizing by using toluene to obtain a white crystal as a final product antioxidant 330.
In the process of reducing 3, 5-di-tert-butyl-4-hydroxybenzene alcohol by using 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material into 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, tetrahydrofuran THF is used as a solvent, and Zn (BH)4)2As a reducing agent, the reduction reaction temperature is 60-66 ℃, and the reaction time is 5-10 hours; distilling and recovering tetrahydrofuran THF (tetrahydrofuran) as a solvent, cooling to room temperature after the reaction is finished, and adding methanol into the system; stirring for 30 minutes, filtering salt in the system, concentrating and cooling the filtrate to separate out a product, and filtering to obtain the product 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol.
The invention has the following beneficial effects:
in the first aspect, the invention takes 3, 5-di-tert-butyl-4-hydroxybenzoic acid as the initial raw material. The 3, 5-di-tert-butyl-4-hydroxybenzoic acid has high industrial degree of production, and is an easily obtained raw material with economic price; using tetrahydrofuran THF as solvent and Zn (BH)4)2The method is used for reducing by a reducing agent, the reaction yield is high, the optimal yield can reach 95%, the purity of the obtained reduced product is high, and the post-treatment is simple in the industrial process. Therefore, the synthesis of the antioxidant 330 by using 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material and reducing the initial raw material into alcohol is a process route with great industrial value.
In a second aspect, sulfuric acid is complexed with a phase transfer catalyst as a catalyst for the condensation reaction process. Due to the addition of the phase transfer catalyst, the catalytic effect of the concentrated sulfuric acid is greatly improved, the consumption of the concentrated sulfuric acid is reduced, and the method has great industrial value. The research on the reaction catalyst is numerous, the catalyst can be selected from inorganic acid, organic acid, Lewis acid and the like, wherein the organic acid is miscible with the reaction system, the system cannot be separated by a standing and layering mode, and a large amount of alkali is needed for neutralization, water washing and the like; lewis acid has the defects of high price, large dosage, unsatisfactory yield, hydrolysis and separation by adding water in the post-treatment, and the like.
The sulfuric acid has the characteristics of low price, easy obtainment and relatively convenient post-treatment, and is still the first choice for the current industrialization. However, the concentrated sulfuric acid is not compatible in the reaction system, so the catalytic efficiency is not ideal under the condition of high-speed stirring in the reaction. Polyethylene glycol compounds (PEGs) are regarded as open-chain crown ethers, and are widely applied to solid-liquid, liquid-liquid and other heterogeneous reactions in organic synthesis at present. Therefore, the present invention uses polyethylene glycol as a phase transfer catalyst to improve this deficiency.
Detailed Description
A preparation method of an antioxidant 330 takes 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material, prepares 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol through reduction, and then generates the antioxidant 330 through condensation with mesitylene, wherein the chemical name is 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene. The specific reaction equation is as follows:
in the process of reducing 3, 5-di-tert-butyl-4-hydroxybenzene alcohol by using 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material into 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, tetrahydrofuran THF is used as a solvent, and Zn (BH)4)2As a reducing agent, the reduction reaction temperature is 60-66 ℃, and the reaction time is 5-10 hours.
In the process of condensing the 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol and mesitylene to generate the antioxidant 330, dichloromethane is used as a solvent, and the compound of a phase transfer catalyst and concentrated sulfuric acid is used as a mixed complexing agent, wherein the reaction temperature is 3-8 ℃, and the reaction time is 2-4 hours.
In the process of condensing the 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol and mesitylene to generate the antioxidant 330, the phase transfer catalyst is a polyethylene glycol series with the molecular weight of 200-1000.
The acid catalysis is a mixed complexing agent of a phase transfer catalyst and concentrated sulfuric acid, and the concentrated sulfuric acid is sulfuric acid with the mass concentration of 85%; mass ratio mConcentrated sulfuric acid：mPolyethylene glycol=100：3.0。
The acid catalysis is a mixed complexing agent of a phase transfer catalyst and concentrated sulfuric acid, the using amount of the mixed complexing agent is 2.5 times of that of mesitylene, and m isComplexing agent：mMesitylene=2.5：1.0。
Adding mesitylene and dichloromethane into a glass reactor, carrying out ice-water bath at 3-8 ℃, dropwise adding the solution, continuing to react for 3 hours after dropwise adding for 1 hour, detecting a liquid phase until the raw materials disappear, and stopping the reaction; and (3) transferring the reaction solution to a separating funnel, standing for layering, removing a lower sulfuric acid phase, washing an upper organic phase to be neutral by using a sodium bicarbonate solution, distilling and recovering dichloromethane, and recrystallizing by using toluene to obtain a white crystal as a final product antioxidant 330.
In the process of reducing 3, 5-di-tert-butyl-4-hydroxybenzene alcohol by using 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material into 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, tetrahydrofuran THF is used as a solvent, and Zn (BH)4)2As a reducing agent, the reduction reaction temperature is 60-66 ℃, and the reaction time is 5-10 hours; distilling and recovering tetrahydrofuran THF (tetrahydrofuran) as a solvent, cooling to room temperature after the reaction is finished, and adding methanol into the system; stirring for 30 minutes, filtering salt in the system, concentrating and cooling the filtrate to separate out a product, and filtering to obtain the product 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol.
The whole synthesis process comprises two steps of reactions:
the first step is a reduction reaction: 3, 5-di-tert-butyl-4-hydroxybenzoic acid is used as an initial raw material, tetrahydrofuran THF is used as a solvent, and Zn (BH)4)2Reducing the reducing agent to prepare 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol;
the second step is condensation reaction: the 3, 5-di-tert-butyl-4-hydroxybenzene methanol and mesitylene synthesized by the above reaction are condensed to generate the antioxidant 330 under the composite catalysis of concentrated sulfuric acid and polyethylene glycol (molecular weight 200-1000-).
The specific implementation operation details of the invention are as follows:
(1) the reduction reaction process comprises the following steps:
respectively adding 3, 5-di-tert-butyl-4-hydroxybenzoic acid and TH into a glass reactorF (tetrahydrofuran), Zn (BH)4)2(ii) a Slowly heating to 60-66 deg.C, reacting for 6-8 hr, sampling, and stopping reaction when reaction requirement is met. After the reaction is finished, distilling and recovering tetrahydrofuran THF (tetrahydrofuran) serving as a solvent; and cooling to room temperature, adding 300 g of methanol into the system, stirring for 30 minutes, filtering salt in the system, concentrating and cooling the filtrate to separate out a product, and filtering to obtain the product 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol.
(2) The condensation reaction process comprises the following steps:
adding mesitylene and dichloromethane into a glass reactor, performing ice-water bath at 3-8 ℃, beginning to dropwise add the composite catalyst and dichloromethane solution of 3, 5-di-tert-butyl-4-hydroxybenzyl methyl alcohol, continuing to react for about 3 hours after the dropwise addition is finished for 1 hour, and stopping the reaction after the liquid phase detection is finished until the raw materials disappear. And (3) transferring the reaction solution to a separating funnel, standing for layering, removing a lower sulfuric acid phase, washing an upper organic phase to be neutral by using a sodium bicarbonate solution, distilling and recovering dichloromethane, and recrystallizing by using toluene to obtain a white crystal as a final product antioxidant 330.
Example 1
(1) Reduction: 82.5 g (0.33mo1) of 3, 5-di-tert-butyl-4-hydroxybenzoic acid, 200ml of tetrahydrofuran and a reducing agent Zn (BH) were weighed out4)2Adding 16 g (0.17mo1) of the mixture into a glass reactor, stirring and heating to 63 ℃, reacting for 7 hours, sampling and detecting to be qualified, and distilling and recovering tetrahydrofuran at 80 ℃; 300 g of methanol extraction product is added into the system, and a large amount of crystals are obtained after salt filtration and concentration, wherein the product is 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, and the yield is 95.0%.
(2) Condensation: 27.2g of the product (3, 5-di-tert-butyl-4-hydroxybenzyl alcohol) obtained by the above reaction
(0.1088mo1) dissolved in 100ml of dichloromethane for standby; adding 4.3 g (0.035 mol) of mesitylene and 100ml of dichloromethane into a glass reactor, carrying out ice-water bath at 8 ℃, and beginning to dropwise add 10.75 g of 85% sulfuric acid/polyethylene glycol 400 mixture; and simultaneously dropwise adding a dichloromethane solution of 3, 5-di-tert-butyl-4-hydroxybenzyl methyl ether, continuously reacting for about 3 hours after dropwise adding for 1 hour until the raw materials disappear, and stopping the reaction. The reaction solution was transferred to a separatory funnel, the lower aqueous phase was separated off, and the upper organic phase was washed with water to neutrality. The dichloromethane is recovered by distillation, white crystals obtained by recrystallization with toluene are the final product antioxidant 330, and the yield is 85.5%.
Example 2
(1) Reduction: 82.5 g (0.33mo1) of 3, 5-di-tert-butyl-4-hydroxybenzoic acid, 200ml of tetrahydrofuran and a reducing agent Zn (BH) were weighed out4)2Adding 16 g (0.17mo1) of the mixture into a glass reactor, stirring and heating to 66 ℃, starting refluxing tetrahydrofuran, reacting for 5 hours, sampling and detecting to be qualified, and distilling and recovering the tetrahydrofuran at 80 ℃; 300 g of methanol extraction product is added into the system, and a large amount of crystals are obtained after salt filtration and concentration, wherein the product is 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, and the yield is 92.5%.
(2) Condensation: 27.2g of the product (3, 5-di-tert-butyl-4-hydroxybenzyl alcohol) obtained by the above reaction
(0.1088mo1) dissolved in 100ml of dichloromethane for use; adding 4.3 g (0.035 mol) of mesitylene and 100ml of dichloromethane into a glass reactor, heating in an ice-water bath at 3 ℃, and beginning to dropwise add 10.75 g of 85% sulfuric acid/polyethylene glycol 200 mixture; and simultaneously dropwise adding a dichloromethane solution of 3, 5-di-tert-butyl-4-hydroxybenzyl methyl ether, continuously reacting for about 4 hours after dropwise adding for 1 hour until the raw materials disappear, and stopping the reaction. The reaction solution was transferred to a separatory funnel, the lower aqueous phase was separated off, and the upper organic phase was washed with water to neutrality. The dichloromethane is recovered by distillation, white crystals obtained by recrystallization with toluene are the final product antioxidant 330, and the yield is 81.5%.
Example 3
(1) Reduction: 82.5 g (0.33mo1) of 3, 5-di-tert-butyl-4-hydroxybenzoic acid, 200ml of tetrahydrofuran and a reducing agent Zn (BH) were weighed out4)2Adding 16 g (0.17mo1) of the tetrahydrofuran into a glass reactor, stirring and heating to 60 ℃, reacting for 10 hours, sampling and detecting to be qualified, and distilling and recovering the tetrahydrofuran at 80 ℃; 300 g of methanol extraction product is added into the system, and a large amount of crystals are obtained after salt filtration and concentration, wherein the product is 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, and the yield is 94.2%.
(2) Condensation: 27.2g of the product (3, 5-di-tert-butyl-4-hydroxybenzyl alcohol) obtained by the above reaction
(0.1088mo1) dissolved in 100ml of dichloromethane for use; adding 4.3 g (0.035 mol) of mesitylene and 100ml of dichloromethane into a glass reactor, heating in an ice-water bath at 3 ℃, and beginning to dropwise add 10.75 g of 85% sulfuric acid/polyethylene glycol 600 mixture; and simultaneously dropwise adding a dichloromethane solution of 3, 5-di-tert-butyl-4-hydroxybenzyl methyl ether, continuously reacting for about 4 hours after dropwise adding for 1 hour until the raw materials disappear, and stopping the reaction. The reaction solution was transferred to a separatory funnel, the lower aqueous phase was separated off, and the upper organic phase was washed with water to neutrality. The dichloromethane was recovered by distillation and recrystallized from toluene to obtain white crystals as the final product antioxidant 330 in 84.0% yield.
Example 4
(1) Reduction: 82.5 g (0.33mo1) of 3, 5-di-tert-butyl-4-hydroxybenzoic acid, 200ml of tetrahydrofuran and a reducing agent Zn (BH) were weighed out4)2Adding 16 g (0.17mo1) of the mixture into a glass reactor, stirring and heating to 63 ℃, reacting for 7 hours, sampling and detecting to be qualified, and distilling and recovering tetrahydrofuran at 80 ℃; 300 g of methanol extraction product is added into the system, and a large amount of crystals are obtained after salt filtration and concentration, wherein the product is 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, and the yield is 93.8%.
(2) Condensation: 27.2g of the product (3, 5-di-tert-butyl-4-hydroxybenzyl alcohol) obtained by the above reaction
(0.1088mo1) dissolved in 100ml of dichloromethane for use; adding 4.3 g (0.035 mol) of mesitylene and 100ml of dichloromethane into a glass reactor, carrying out ice-water bath at 8 ℃, and beginning to dropwise add 10.75 g of 85% sulfuric acid/polyethylene glycol 1000 mixture; and simultaneously dropwise adding a dichloromethane solution of 3, 5-di-tert-butyl-4-hydroxybenzyl methyl ether, continuously reacting for about 2 hours after dropwise adding for 1 hour until the raw materials disappear, and stopping the reaction. The reaction solution was transferred to a separatory funnel, the lower aqueous phase was separated off, and the upper organic phase was washed with water to neutrality. The dichloromethane is recovered by distillation, white crystals obtained by recrystallization with toluene are the final product antioxidant 330, and the yield is 82.5%.
The total yield of the antioxidant 330 as the final product in the disclosed embodiments 1 to 4 is more than 80%, and compared with the traditional process, the yield is greatly improved; but also greatly improves the catalytic effect, reduces the dosage of inorganic acid and has great industrial value.
Claims (8)
1. A preparation method of an antioxidant 330 is characterized by comprising the following steps: 3, 5-di-tert-butyl-4-hydroxybenzoic acid is used as an initial raw material, 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol is prepared by reduction, and then the 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol and mesitylene are condensed to generate an antioxidant 330, wherein the chemical name of the antioxidant 330 is 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene.
2. The method of claim 1, wherein the antioxidant 330 is prepared by: in the process of reducing 3, 5-di-tert-butyl-4-hydroxybenzene alcohol by using 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material into 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, tetrahydrofuran THF is used as a solvent, and Zn (BH)4)2As a reducing agent, the reduction reaction temperature is 60-66 ℃, and the reaction time is 5-10 hours.
3. The method of claim 1, wherein the antioxidant 330 is prepared by: in the process of condensing the 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol and mesitylene to generate the antioxidant 330, dichloromethane is used as a solvent, a mixed complexing agent of a phase transfer catalyst and concentrated sulfuric acid is used, the phase transfer catalyst is a polyethylene glycol solution, the reaction temperature is 3-8 ℃, and the reaction time is 2-4 hours.
4. The method of claim 3, wherein the antioxidant 330 is prepared by: in the process of condensing the 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol and mesitylene to generate the antioxidant 330, the phase transfer catalyst is a polyethylene glycol series with the molecular weight of 200-1000.
5. The method of claim 3, wherein the antioxidant 330 is prepared by: the acid catalyst is a mixed complexing agent of a phase transfer catalyst and concentrated sulfuric acid, and the mass concentration of the concentrated sulfuric acid is 85%; mass ratio mConcentrated sulfuric acid：mPolyethylene glycol=100：3.0。
6. The method of claim 3, wherein the antioxidant 330 is prepared by: the acid catalysis is a mixed complexing agent of a phase transfer catalyst and concentrated sulfuric acid, the using amount of the mixed complexing agent is 2.5 times of that of mesitylene, and m isComplexing agent：mMesitylene=2.5：1.0。
7. The method of claim 3, wherein the antioxidant 330 is prepared by: adding mesitylene and dichloromethane into a glass reactor, carrying out ice-water bath at 3-8 ℃, dropwise adding the solution, continuing to react for 3 hours after dropwise adding for 1 hour, detecting a liquid phase until the raw materials disappear, and stopping the reaction; and (3) transferring the reaction solution to a separating funnel, standing for layering, removing a lower sulfuric acid phase, washing an upper organic phase to be neutral by using a sodium bicarbonate solution, distilling and recovering dichloromethane, and recrystallizing by using toluene to obtain a white crystal as a final product antioxidant 330.
8. The method of claim 2, wherein the antioxidant 330 is prepared by: in the process of reducing 3, 5-di-tert-butyl-4-hydroxybenzene alcohol by using 3, 5-di-tert-butyl-4-hydroxybenzoic acid as an initial raw material into 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol, tetrahydrofuran THF is used as a solvent, and Zn (BH)4)2As a reducing agent, the reduction reaction temperature is 60-66 ℃, and the reaction time is 5-10 hours; distilling and recovering tetrahydrofuran THF (tetrahydrofuran) as a solvent, cooling to room temperature after the reaction is finished, and adding methanol into the system; stirring for 30 minutes, filtering salt in the system, concentrating and cooling the filtrate to separate out a product, and filtering to obtain the product 3, 5-di-tert-butyl-4-hydroxybenzyl alcohol.
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