Preparation method of styrylphenol polyoxyethylene ether

Abstract

The invention provides a styrylphenol polyoxyethylene ether preparation method, which comprises: 1, placing an Al-SBA-15 mesoporous molecular sieve, a quaternary ammonium base and styrylphenol in a high-pressure kettle, mixing, carrying out nitrogen protection, heating to a temperature of 80-100 DEG C, and carrying out a reaction initial pressure of 0.1-0.3 MPa, 2, metering and adding ethylene oxide, and carrying out a polymerization reaction to obtain the styrylphenol polyoxyethylene ether, when the reaction is carried out until the pressure is not obviously reduced any more, stopping the reaction, cooling and discharging to obtain styrylphenol polyoxyethylene ether; the preparation method of the Al-SBA-15 mesoporous molecular sieve comprises the following steps: dissolving P123 in deionized water to obtain a transparent solution, adding tetraethoxysilane into the transparent solution, metering and adding NaAlO2 according to a ratio of n (Si): n (Al) of (10-29): 1 to obtain a mixed solution, transferring the mixed solution into a crystallization kettle for crystallization at 90-110 DEG C, washing a crystallized substance with deionized water, and drying to obtain the Al-SBA-15 mesoporous molecular sieve. And then raising the temperature to 530-580 DEG C and keeping the temperature for 4-6 hours. The method provided by the invention is beneficial to reducing the color value of polyether and narrowing the molecular weight distribution coefficient.

Description

Technical Field

[0001] The invention relates to the technical field of polyethers, and in particular to a method for preparing styrylphenol polyoxyethylene ether. Background Art

[0002] Styrylphenol polyoxyethylene ether is usually obtained by ethoxylation of styrylphenol and ethylene oxide under the action of a catalyst. The catalyst used for the ethoxylation reaction is usually BF3, SnCl4, AlCl3, NaOH, KOH, CH3ONa. Among these catalysts, acidic catalysts have the problems of more side reactions, limited activity, strong corrosiveness and poor reaction stability. The above-mentioned strong base catalysts are prone to cause problems such as wide molecular weight distribution and dark product color, thereby affecting the performance of the product. Summary of the invention

[0003] In order to overcome the deficiencies of the prior art, the object of the present invention is to provide a method for preparing styrylphenol polyoxyethylene ether, thereby facilitating reducing the color value of styrylphenol polyoxyethylene ether and narrowing the molecular weight distribution coefficient of styrylphenol polyoxyethylene ether.

[0004] To solve the above problems, the technical solution adopted by the present invention is as follows:

[0005] A method for preparing styrylphenol polyoxyethylene ether comprises the following steps:

[0006] Step 1: Al-SBA-15 mesoporous molecular sieve, quaternary ammonium base, and styrylphenol are placed in an autoclave and mixed, protected by nitrogen, and heated to 80°C-100°C, with an initial reaction pressure of 0.1-0.3 MPa; and

[0007] Step 2: adding ethylene oxide in a metered manner to carry out polymerization reaction, and when the reaction is carried out until the pressure no longer drops significantly, stopping the reaction, cooling and discharging the material to obtain styrylphenol polyoxyethylene ether;

[0008] The preparation of the Al-SBA-15 mesoporous molecular sieve comprises:

[0009] Dissolve P123 in deionized water, adjust the system to acidity, and stir at 35℃-45℃ to obtain a transparent solution;

[0010] Adding tetraethyl orthosilicate to the transparent solution;

[0011] According to the amount of substance, NaAlO2 is added in a ratio of n(Si):n(Al) of 10-29:1, and the mixture is continuously stirred and dispersed at 35°C-45°C to obtain a mixed solution;

[0012] The mixed solution is transferred to a crystallization axe for crystallization to obtain a crystallized product, and the crystallization temperature is 90°C-110°C;

[0013] The crystallized product is washed with deionized water and dried, and then heated to 530° C. to 580° C. and kept warm for 4 to 6 hours to obtain the Al-SBA-15 mesoporous molecular sieve.

[0014] In some possible implementations, based on the amount of substance, the ratio of n(Si):n(Al) is 20-29:1.

[0015] In some possible implementations, the amount of the quaternary ammonium base used is 30%-40% by weight of the Al-SBA-15 mesoporous molecular sieve, and the amount of the quaternary ammonium base used is 0.4%-0.6% by weight of the styrylphenol.

[0016] In some possible implementations, the amount of the quaternary ammonium base used is 32% to 38% by weight of the Al-SBA-15 mesoporous molecular sieve.

[0017] In some possible implementations, the hydrocarbon group of the quaternary ammonium base is an aliphatic hydrocarbon group, and one of the hydrocarbon groups of the quaternary ammonium base is a methyl group.

[0018] In some possible embodiments, the quaternary ammonium base is tetramethylammonium hydroxide.

[0019] In some possible implementations, the ethylene oxide addition time is 1.5-2 hours.

[0020] In some possible implementations, step three is also included:

[0021] The molecular sieve in the product is separated by filtering, the separated molecular sieve is rinsed with deionized water, and dried at 130° C.-150° C., and then calcined at 530° C.-580° C. to recover the Al-SBA-15 mesoporous molecular sieve.

[0022] In some possible embodiments, the preparation of the styrylphenol comprises:

[0023] Phenol and the alkylation catalyst are placed in nitrogen and heated to 95-100° C. Stir and add styrene dropwise for 2-2.5 hours. The material molar ratio of the phenol to the styrene is 1:2-2.5. The amount of the alkylation catalyst is 0.15%-0.2% of the mass of the phenol.

[0024] After the addition is completed, the reaction is kept warm for 1.8-2 hours until the refractive index of the product reaches 1.5985-1.6020. After the reaction is complete, the mixture is degassed and cooled to room temperature to obtain styrylphenol.

[0025] In some possible embodiments, the alkylation catalyst is selected from one of methanesulfonic acid and p-toluenesulfonic acid.

[0026] Compared with the prior art, the present invention has the following beneficial effects:

[0027] In the present application, an Al-SBA-15 mesoporous molecular sieve containing appropriate acidic sites is prepared in a specific manner, and a quaternary ammonium base is adsorbed by the molecular sieve into the polymerization reaction pores. The quaternary ammonium base as an ethoxylation reaction catalyst is coordinated with the pores, specific reaction temperature and reaction pressure, which is beneficial to reducing the color value of styrylphenol polyoxyethylene ether and narrowing the molecular weight distribution coefficient of the polyether.

[0028] The present invention is further described in detail below in conjunction with the accompanying drawings and specific embodiments. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 The present invention is a flow chart of preparing polyoxyethylene styrylphenol ether according to one embodiment of the present invention. DETAILED DESCRIPTION

[0030] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of this application.

[0031] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art of the present invention. The terms used in the specification of the present invention herein are only for the purpose of describing specific embodiments and are not intended to limit the present invention.

[0032] Some embodiments of the present invention are described in detail below in conjunction with the accompanying drawings. In the absence of conflict, the following embodiments and features in the embodiments can be combined with each other.

[0033] An embodiment of the present application provides a method for preparing styrylphenol polyoxyethylene ether, comprising the following steps:

[0034] Step S101: Al-SBA-15 mesoporous molecular sieve, quaternary ammonium base and styrylphenol are placed in an autoclave for mixing, protected by nitrogen, and heated to 80°C-100°C, with an initial reaction pressure of 0.1-0.3 MPa.

[0035] The preparation of the Al-SBA-15 mesoporous molecular sieve comprises:

[0036] Dissolve P123 (another name for polyethylene oxide-polypropylene oxide-polyethylene oxide triblock copolymer) in deionized water, adjust the system to acidity, and stir at 35℃-45℃ to obtain a transparent solution. P123 is used as a template agent. For example, hydrochloric acid can be added to the system to adjust the pH, and the concentration of hydrochloric acid can be 1-3 mol / L －1 .

[0037] To the clear solution was added tetraethyl orthosilicate.

[0038] According to the amount of the substance, NaAlO2 is added in a ratio of n(Si):n(Al) of 10-29:1, and the mixture is continuously stirred and dispersed at 35° C. to 45° C. to obtain a mixed solution. For example, the stirring and dispersing time can be at least 15 hours.

[0039] In some embodiments, the n(Si):n(Al) is 20-29:1, and further limiting the raw material ratio is beneficial to reducing pore collapse, thereby improving the utilization rate of the mesoporous molecular sieve and further ensuring the size of the polymerization reaction site to assist in improving the molecular weight distribution coefficient.

[0040] The mixed solution is transferred to a crystallization axe for crystallization to obtain a crystallized product, and the crystallization temperature is 90° C. to 110° C. Exemplarily, the crystallization time may be 2 days or more, and exemplary, may be 2 days to 4 days.

[0041] The crystallized product is washed with deionized water and dried, and then heated to 530° C. to 580° C. and kept at this temperature for 4 to 6 hours to obtain the Al-SBA-15 mesoporous molecular sieve. For example, vacuum drying can be used.

[0042] In the Al-SBA-15 mesoporous molecular sieve, Al is connected to the silicon-oxygen skeleton, which produces acidic sites on the inner surface of the molecular sieve. The acidic sites can adsorb N in the quaternary ammonium base. + , so that the quaternary ammonium base can be introduced into the pores for catalytic reaction. The ratio of Si and Al can regulate the content of acidic sites. Since the catalyst for ethoxylation can be an acidic catalyst, when the acidic site content is too high, the Al-SBA-15 mesoporous molecular sieve may catalyze ethoxylation, thereby affecting the base-catalyzed process. In the present application, the ratio of Al is controlled to control the acidic site content so as to introduce the base catalyst into the reaction pores, and the base catalyst subsequently catalyzes the ethoxylation reaction.

[0043] In some embodiments, the amount of the quaternary ammonium base is 30%-40% by weight of the Al-SBA-15 mesoporous molecular sieve, so as to ensure the adsorption effect of the Al-SBA-15 mesoporous molecular sieve and reduce the dispersion of the quaternary ammonium base outside the reaction channel, thereby improving the controllability of the reaction.

[0044] In some embodiments, the amount of the quaternary ammonium base is 32%-38% by weight of the Al-SBA-15 mesoporous molecular sieve, so as to further adjust the balance between the acid sites and the ethoxylation catalyst, thereby further facilitating the control of catalyst outflow and acid site residues.

[0045] In some embodiments, the amount of the quaternary ammonium base is 0.4% to 0.6% of the styrylphenol. Controlling the amount of the ethoxylation catalyst is beneficial to controlling the side reactions of the polymerization process, thereby further reducing the color value and further narrowing the molecular weight distribution.

[0046] In some embodiments, the hydrocarbon group of the quaternary ammonium base is an aliphatic hydrocarbon group, and one of the hydrocarbon groups of the quaternary ammonium base is a methyl group, thereby reducing the steric hindrance of the quaternary ammonium base to ensure the adsorption strength of the catalyst. Exemplarily, the quaternary ammonium base may include one of tetramethylammonium hydroxide, trimethylethylammonium hydroxide, trimethylpropylammonium hydroxide or dimethyldiethylammonium hydroxide.

[0047] In some embodiments, the quaternary ammonium base is tetramethylammonium hydroxide, which helps to reduce the adsorption steric hindrance and the catalytic steric hindrance.

[0048] In another embodiment, one of the hydrocarbon groups of the quaternary ammonium base may be an aromatic hydrocarbon group. In another embodiment, the quaternary ammonium base is tetraethylammonium hydroxide.

[0049] In some embodiments, the preparation of the styrylphenol comprises:

[0050] Phenol and alkylation catalyst are heated to 95-100°C in nitrogen, styrene is added dropwise under stirring for 2-2.5 hours, the material molar ratio of phenol to styrene is 1:2-2.5, and the amount of alkylation catalyst is 0.15%-0.2% of the mass of phenol.

[0051] After the addition is completed, the reaction is kept warm for 1.8-2 hours until the refractive index of the product reaches 1.5985-1.6020 (25°C, refer to GB / 6488-2008, determination of refractive index of chemical products, test 3 times under the same conditions, and take the average value as the test result). After the reaction is complete, degas and cool to room temperature to obtain styrylphenol. Degassing can remove unreacted styrene materials.

[0052] The styrylphenol prepared under the above conditions can reduce the self-polymerization of styrene and reduce the oxidation of phenol, thereby facilitating further reduction of the color value (Pt-Co) of styrylphenol polyoxyethylene ether.

[0053] In another embodiment, styrene can also be added dropwise to the mixture of phenol and the alkylation catalyst to prepare styrylphenol, but the reaction temperature of the alkylation can be changed, for example, the reaction can be carried out within 80-95°C, and the time for adding styrene can also be changed, for example, the adding time can be set within 1 to 2 hours. The insulation time can also be changed, for example, the insulation time can be less than 1.8 hours.

[0054] In some embodiments, the alkylation catalyst is selected from methanesulfonic acid or p-toluenesulfonic acid. The organic catalyst is selected to control the reaction activity, thereby avoiding the generation of excessive by-products.

[0055] Step S102: adding ethylene oxide in a metered manner to carry out polymerization reaction. When the reaction is carried out until the pressure no longer drops significantly, the reaction is stopped, the temperature is lowered, and the material is discharged to obtain styrylphenol polyoxyethylene ether.

[0056] In some embodiments, the feeding time of ethylene oxide is 1.5-2 hours. Controlling the feeding time is beneficial to controlling the polymerization exotherm and ensuring the uniformity of the reactants participating in the reaction, thereby reducing by-products to reduce the color value and narrow the molecular weight distribution.

[0057] Step S103: Filter to separate the molecular sieve in the product, rinse the separated molecular sieve with deionized water, and dry at 130°C-150°C. After drying, calcine at 530°C-580°C to recover the Al-SBA-15 mesoporous molecular sieve, thereby achieving effective separation of the catalyst, molecular sieve and product. Exemplarily, the calcination time can be at least 4 hours. The setting of deionized water and drying temperature is conducive to the desorption and decomposition of quaternary ammonium base. Therefore, step 103 is conducive to purifying the polymer product. In addition, it can be seen that the selection of the combination of molecular sieve and quaternary ammonium base as a catalyst is also convenient for subsequent treatment of the product, and the molecular sieve can be reused, which also reduces the production cost to a certain extent.

[0058] In the present application, an Al-SBA-15 mesoporous molecular sieve containing appropriate acidic sites is prepared in a specific manner, and a quaternary ammonium base is adsorbed by the molecular sieve into the polymerization reaction pores. The quaternary ammonium base as an ethoxylation reaction catalyst is coordinated with the pores, specific reaction temperature and reaction pressure, which is beneficial to reducing the color value of styrylphenol polyoxyethylene ether and narrowing the molecular weight distribution coefficient of the polyether.

[0059] Specific:

[0060] Embodiment 1:

[0061] Phenol and an alkylation catalyst are added into a four-necked flask, wherein the alkylation catalyst is methanesulfonic acid, and the temperature is raised to 98°C-100°C under nitrogen. Styrene is added dropwise under stirring for 2 hours. The material molar ratio of the phenol to the styrene is 1:2, and the amount of the alkylation catalyst is 0.15% of the mass of the phenol.

[0062] After the addition is completed, the reaction is kept warm for 1.8 hours until the refractive index of the product reaches 1.5985-1.6020 (25°C, refer to GB / 6488-2008, chemical product refractive index determination method, test 3 times under the same conditions, and take the average value as the test result). After the reaction is complete, degas and cool to room temperature to obtain styrylphenol.

[0063] Al-SBA-15 mesoporous molecular sieve, quaternary ammonium base, and the styrylphenol are placed in an autoclave and mixed, protected by nitrogen, and heated to 80°C-85°C, and the initial reaction pressure is set to 0.1-0.2MPa. Since there is exothermic behavior during the reaction, the pressure and temperature fluctuate during the reaction, so the temperature and pressure are usually controlled within a certain range rather than a fixed value. By weight, the amount of the quaternary ammonium base is 40% of the Al-SBA-15 mesoporous molecular sieve, and the amount of the quaternary ammonium base is 0.4% of the styrylphenol. The quaternary ammonium base is tetramethylammonium hydroxide.

[0064] Specifically, the preparation of the Al-SBA-15 mesoporous molecular sieve includes:

[0065] 4 g of P123 was dissolved in 30 g of deionized water, and 120 g of 2 mol / Ld HCl was added to adjust the system to acidity. The mixture was stirred continuously at 40° C. for 18 hours to obtain a transparent solution.

[0066] To the clear solution was added tetraethyl orthosilicate.

[0067] According to the amount of substance, NaAlO2 was added in a ratio of n(Si):n(Al) of 10:1, and the mixture was stirred continuously at 40°C for 18 hours until the system was uniformly dispersed to obtain a mixed solution.

[0068] The mixed solution is transferred to a crystallization axe for crystallization to obtain a crystallized product. The crystallization temperature is 100° C. and the crystallization time is 3 days.

[0069] The crystallized product is washed with deionized water and dried (vacuum drying at a drying temperature of 80° C.), then heated to 550° C. and kept at this temperature for 4 to 4.5 hours to obtain the Al-SBA-15 mesoporous molecular sieve.

[0070] Ethylene oxide was added in a metered manner for polymerization reaction, and when the pressure no longer dropped significantly, the reaction was stopped, the temperature was lowered, and the material was discharged to obtain styrylphenol polyoxyethylene ether. The ethylene oxide was added for 2 hours.

[0071] The molecular sieve in the product is separated by filtration, and the separated molecular sieve is rinsed with deionized water and dried at 130° C. After drying, it is calcined at 580° C. for 4 to 4.5 hours to separate the polymer product and the molecular sieve.

[0072] Embodiment 2:

[0073] The difference from Example 1 is that after adding phenol and alkylation catalyst into a four-necked flask, the temperature is raised to 95°C-98°C under nitrogen, the alkylation catalyst is p-toluenesulfonic acid, the styrene is added dropwise after 2.5 hours, the material molar ratio of phenol to styrene is 1:2.4, and the amount of alkylation catalyst is 0.17% of the mass of phenol. After the addition of styrene is completed, the reaction is kept warm for 2 hours.

[0074] Al-SBA-15 mesoporous molecular sieve, quaternary ammonium base and the styrylphenol are placed in an autoclave and mixed, and then the temperature is raised to 85°C-90°C. The initial reaction pressure is set to 0.2-0.3MPa. By weight, the amount of the quaternary ammonium base is 35% of the Al-SBA-15 mesoporous molecular sieve, and the amount of the quaternary ammonium base is 0.5% of the styrylphenol. By amount of substance, n(Si):n(Al) is 15:1. The feeding time of the ethylene oxide is 1.5 hours. The separated molecular sieve is rinsed with deionized water and dried at 150°C, and then calcined at 530°C for 4.5 to 5 hours.

[0075] Embodiment 3:

[0076] The difference from Example 1 is that the quaternary ammonium base is trimethyl ethyl ammonium hydroxide, and the Al-SBA-15 mesoporous molecular sieve, the quaternary ammonium base and the styrylphenol are placed in an autoclave and mixed, and then the temperature is raised to 95° C.-100° C.

[0077] Embodiment 4:

[0078] The difference from Example 2 is that the addition of styrene is completed after 2.2 hours, the material molar ratio of phenol to styrene is 1:2.5, the amount of the alkylation catalyst is 0.2% of the mass of the phenol, and n(Si):n(Al) is 20:1 in terms of the amount of substance.

[0079] Embodiment 5:

[0080] The difference from Example 4 is that, by weight, the amount of the quaternary ammonium base used is 38% of the Al-SBA-15 mesoporous molecular sieve.

[0081] Embodiment 6:

[0082] The difference from Example 1 is that, by weight, the amount of the quaternary ammonium base used is 32% of the Al-SBA-15 mesoporous molecular sieve, and by amount of substance, n(Si):n(Al) is 29:1.

[0083] Embodiment 7:

[0084] The difference from Example 1 is that, by weight, the amount of the quaternary ammonium base used is 34% of the Al-SBA-15 mesoporous molecular sieve, and by amount of substance, n(Si):n(Al) is 25:1.

[0085] Embodiment 8:

[0086] The difference from Example 1 is that the addition time of ethylene oxide is 2.5 hours.

[0087] Embodiment 9:

[0088] The difference from Example 1 is that the addition time of ethylene oxide is 1.4 hours.

[0089] Comparative Example 1:

[0090] The difference from Example 1 is that the quaternary ammonium base is omitted, and the prepared Al-SBA-15 mesoporous molecular sieve and styrylphenol are placed in an autoclave for mixed reaction.

[0091] Comparative Example 2:

[0092] The difference from Example 1 is that the Al-SBA-15 mesoporous molecular sieve is omitted, and the quaternary ammonium base and styrylphenol are placed in an autoclave for mixed reaction.

[0093] Since the raw materials used in the above examples and comparative examples are all conventional reagents and can be purchased from the market, the purchase manufacturers and brands of the raw materials are not described in detail.

[0094] The color value of the polyether product is measured by a platinum-cobalt colorimeter: the test is conducted three times under the same conditions, and the average value is taken as the test result. The machine model is SD9012A.

[0095] The molecular weight dispersion coefficient of the polyether product was determined by high performance liquid chromatography (Agilent 1200 liquid chromatograph). The analysis conditions were: chromatographic column XDB-C18-B2, column temperature 40° C., methanol / water as solvent, and flow rate 1.0 mL / min.

[0096] The test results of the above embodiments and comparative examples are shown in the following table.

[0097]

[0098]

[0099] Comparing the above examples with the comparative examples, it can be seen that the synergistic effect of the Al-SBA-15 mesoporous molecular sieve and the quaternary ammonium base, combined with the specific reaction temperature and reaction pressure, is conducive to reducing the color value and distribution coefficient of the polyether product, so that the color value of the styrylphenol polyoxyethylene ether provided in the present application is less than or equal to 20, and the molecular weight distribution coefficient is less than 1.1. Comparing Examples 1-3 and Examples 4-7, it can be seen that the ratio of the quaternary ammonium base to the Al-SBA-15 mesoporous molecular sieve and the ratio of elements in the mesoporous molecular sieve are conducive to further reducing the color value and distribution coefficient of the polyether product. Comparing Example 1 with Examples 7 and 8, it can be seen that further limiting the feeding time of ethylene oxide is also conducive to further reducing the color value of the polyether and narrowing the molecular weight distribution of the polyether.

[0100] The above-mentioned embodiments are only preferred embodiments of the present invention and cannot be used to limit the scope of protection of the present invention. Any non-substantial changes and substitutions made by technicians in this field on the basis of the present invention shall fall within the scope of protection required by the present invention.

Claims

1. A method for preparing styrylphenol polyoxyethylene ether, characterized in that: The steps include: Step 1: Al-SBA-15 mesoporous molecular sieve, quaternary ammonium base, and styrylphenol are placed in an autoclave and mixed, protected by nitrogen, and heated to 80°C-100°C, with an initial reaction pressure of 0.1-0.3 MPa; and Step 2: adding ethylene oxide in a metered manner to carry out polymerization reaction, and when the reaction is carried out until the pressure no longer drops significantly, stopping the reaction, cooling and discharging the material to obtain styrylphenol polyoxyethylene ether; The preparation of the Al-SBA-15 mesoporous molecular sieve comprises: Dissolve P123 in deionized water, adjust the system to acidity, and stir at 35℃-45℃ to obtain a transparent solution; Adding tetraethyl orthosilicate to the transparent solution; According to the amount of substance, NaAlO2 is added in a ratio of n(Si):n(Al) of 10-29:1, and the mixture is continuously stirred and dispersed at 35°C-45°C to obtain a mixed solution; The mixed solution is transferred to a crystallization axe for crystallization to obtain a crystallized product, and the crystallization temperature is 90°C-110°C; The crystallized product is washed with deionized water and dried, and then heated to 530° C. to 580° C. and kept warm for 4 to 6 hours to obtain the Al-SBA-15 mesoporous molecular sieve.

2. The preparation method according to claim 1, characterized in that Calculated by the amount of substance, the ratio of n(Si):n(Al) is 20-29:

1.

3. The preparation method according to claim 2, characterized in that: By weight, the amount of the quaternary ammonium base used is 30%-40% of the Al-SBA-15 mesoporous molecular sieve, and the amount of the quaternary ammonium base used is 0.4%-0.6% of the styrylphenol.

4. The preparation method according to claim 3, characterized in that: The amount of the quaternary ammonium base used is 32% to 38% by weight of the Al-SBA-15 mesoporous molecular sieve.

5. The preparation method according to claim 2, characterized in that: The hydrocarbon group of the quaternary ammonium base is an aliphatic hydrocarbon group, and one of the hydrocarbon groups of the quaternary ammonium base is a methyl group.

6. The preparation method according to claim 5, characterized in that: The quaternary ammonium base is tetramethylammonium hydroxide.

7. The preparation method according to claim 1, characterized in that: The feeding time of the ethylene oxide is 1.5-2 hours.

8. The preparation method according to claim 1, characterized in that: Also includes step three: The molecular sieve in the product is separated by filtering, the separated molecular sieve is rinsed with deionized water, and dried at 130° C.-150° C., and then calcined at 530° C.-580° C. to recover the Al-SBA-15 mesoporous molecular sieve.

9. The preparation method according to claim 1, characterized in that: The preparation of the styrylphenol comprises: Phenol and the alkylation catalyst are placed in nitrogen and heated to 95-100° C. Stir and add styrene dropwise for 2-2.5 hours. The material molar ratio of the phenol to the styrene is 1:2-2.

5. The amount of the alkylation catalyst is 0.15%-0.2% of the mass of the phenol. After the addition is completed, the reaction is kept warm for 1.8-2 hours until the refractive index of the product reaches 1.5985-1.6020. After the reaction is complete, the mixture is degassed and cooled to room temperature to obtain styrylphenol.

10. The preparation method according to claim 9, characterized in that: The alkylation catalyst is selected from one of methanesulfonic acid and p-toluenesulfonic acid.

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