Process for the preparation of long chain alkyl phenols using a beta molecular sieve as catalyst

Abstract

This invention proposes a method for the synthesis and analysis of long-chain alkylphenols catalyzed by Beta molecular sieves. The analytical method primarily involves heating the Beta molecular sieve catalyst and adding it to an alkylation reaction system of high-carbon α-olefins and phenol solution to obtain long-chain alkylphenols. The analytical method includes uniformly mixing the long-chain alkylphenols with dichloromethane and then injecting the mixture into a gas chromatograph for detection and analysis. This invention uses Beta molecular sieves as a catalyst, which, compared with traditional liquid acid catalysts, is not only environmentally friendly and meets the requirements of modern green chemical engineering, but also easily separated after the reaction, facilitating catalyst recycling. Analysis results show that the conversion rates of C12-C18 high-carbon α-olefins are as high as 99.9% (C12), 99.8% (C14), 99.4% (C16), and 99.2% (C18), respectively, and the corresponding selectivity of long-chain alkylphenols is as high as 99.9% (C12), 99.9% (C14), 99.2% (C16), and 97.9% (C18), respectively.

Description

Technical Field

[0001] This invention belongs to the field of long-chain alkylphenol technology, specifically relating to a method for synthesizing and analyzing long-chain alkylphenols catalyzed by Beta molecular sieves. Background Technology

[0002] Long-chain alkylphenols are important chemical products, raw materials, and intermediates, widely used in the synthesis of fine chemicals. They are primarily produced by reacting phenol with higher-carbon n-alkanes, higher-carbon n-alcohols, or higher-carbon α-olefins. Because the alkylation of higher-carbon n-alkanes or alcohols requires the introduction of halogens, increasing the process complexity and resulting in lower economic efficiency, higher-carbon α-olefins are used as the main alkyl source in the alkylphenol production process.

[0003] Currently, long-chain alkylphenols are mostly produced in industrial production using traditional liquid acids such as HF and AlCl3 to catalyze the alkylation of olefins and phenols. However, this method suffers from numerous problems, including high levels of product impurities and side reactions, severe equipment corrosion, complex product post-processing, and significant environmental pollution. With increasing environmental awareness, environmentally friendly chemical reaction processes have attracted widespread attention.

[0004] Therefore, seeking a novel alternative catalyst to green this process route is of great significance for achieving the sustainable development of the chemical industry. Summary of the Invention

[0005] To address the aforementioned problems in the prior art, this invention proposes a method for synthesizing and analyzing long-chain alkylphenols using Beta molecular sieve catalysis.

[0006] In a first aspect, the present invention proposes a method for synthesizing long-chain alkylphenols catalyzed by Beta molecular sieves, comprising the following steps:

[0007] S1: Dry the Beta molecular sieve to obtain the dried Beta molecular sieve;

[0008] S2: Phenol is heated and stirred to melt, resulting in liquid phenol;

[0009] S3: Add the high carbon α-olefin to the phenol liquid obtained in step S2, mix, stir and heat to obtain a mixture;

[0010] S4: Add the dried Beta molecular sieve catalyst from step S1 to the mixture obtained in step S3, stir and heat to carry out the alkylation reaction, and long-chain alkylphenols can be obtained.

[0011] In a specific embodiment of the present invention, in step S1, the Beta molecular sieve is selected from a Beta molecular sieve in which the molar ratio of SiO2 to Al2O3 is 15; and / or, the drying temperature is 100-140℃, and the heating time is 2-13h. The catalyst is dried until its mass remains constant.

[0012] In a specific embodiment of the present invention, the melting conditions in step S2 include: a stirring rate of 50-500 rpm, a heating temperature of 100-170°C, and a heating time of 5-50 min.

[0013] As a specific embodiment of the present invention, in step S3, the high carbon α-olefins are C12-C18 olefins, all of which are sourced from the LAO unit of Sinopec Maoming Petrochemical Company.

[0014] And / or, the molar ratio of the added high-carbon α-olefin to the added phenol is 1:(3-8);

[0015] And / or, the stirring rate is 50-500 rpm, the heating temperature is 100-170℃, and the heating time is 5-50 min.

[0016] In a specific embodiment of the present invention, in step S4, the amount of Beta molecular sieve catalyst used is 1-10 wt% of the total mass; specifically, for the synthesis of dodecylphenol, the amount of Beta molecular sieve catalyst used is 4-6 wt% of the total mass of phenol and C12; for the synthesis of tetradecylphenol, the amount of Beta molecular sieve catalyst used is 6-8 wt% of the total mass of phenol and C14; for the synthesis of hexadecylphenol, the amount of Beta molecular sieve catalyst used is 6-8 wt% of the total mass of phenol and C16; and for the synthesis of octadecylphenol, the amount of Beta molecular sieve catalyst used is 8-10 wt% of the total mass of phenol and C18.

[0017] And / or, the stirring speed is 50-500 rpm, the alkylation reaction temperature is 100-170℃, and the reaction time is 2-8 h.

[0018] Secondly, the present invention provides an analytical method for long-chain alkylphenols catalyzed by Beta molecular sieves, comprising: mixing long-chain alkylphenols with dichloromethane and injecting the mixture into a gas chromatograph for detection and analysis.

[0019] As a specific embodiment of the present invention, dichloromethane can effectively disperse long-chain alkylphenol reaction solutions.

[0020] All of the above-mentioned raw materials used in this invention can be prepared in-house or purchased commercially; this invention does not impose any particular limitations on them.

[0021] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0022] 1. The method for synthesizing long-chain alkylphenols catalyzed by Beta molecular sieves provided in this embodiment of the invention uses Beta molecular sieves as a catalyst. Compared with traditional liquid acid catalysts, it is not only environmentally friendly and meets the requirements of modern green chemical industry, but also easy to separate after the reaction, which is conducive to the recycling of the catalyst.

[0023] 2. The method for synthesizing long-chain alkylphenols catalyzed by Beta molecular sieves provided in this embodiment of the invention, after detection and analysis, shows that the conversion rates of C12-C18 high carbon α-olefins are as high as 99.9% (C12), 99.8% (C14), 99.4% (C16) and 99.2% (C18), respectively, and the corresponding selectivity of long-chain alkylphenols are as high as 99.9% (C12), 99.9% (C14), 99.2% (C16) and 97.9% (C18), respectively. Detailed Implementation

[0024] The present invention will be further described below with reference to specific embodiments, but this does not constitute any limitation on the present invention.

[0025] In the various embodiments of the present invention, the molar ratio of SiO2 to Al2O3 in the Beta molecular sieve catalyst is 15; it was purchased from Dalian Molecular Sieve Factory.

[0026] Example 1

[0027] This embodiment provides a method for synthesizing long-chain alkylphenols using a Beta molecular sieve catalyst, the details of which are as follows:

[0028] S1: Place 500g of Beta molecular sieve catalyst in an oven and heat it to dry at 110℃ for 10h.

[0029] S2: Place phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The amount of phenol used is 28 mol (2635.1 g), the stirring speed is 300 rpm, the heating temperature is 110℃, and the time is 30 min.

[0030] S3: Add high-carbon α-olefin (C12) to the above-mentioned glass reactor, stir and heat. The C12 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 7 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 110℃, and the time is 30 min.

[0031] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 5 wt% (190.7 g) of the total mass of phenol and C12, the stirring speed is 300 rpm, the alkylation reaction temperature is 110℃, and the reaction time is 4 h.

[0032] The long-chain alkylphenol (dodecylphenol) synthesized in Example 1 was analyzed. At reaction times of 2 h, 3 h, and 4 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that the Beta molecular sieve catalyzed the synthesis of dodecylphenol with excellent efficiency. At reaction times of 2 h, 3 h, and 4 h, the conversion rate of C12 olefins was as high as 99.9%, and the corresponding selectivity for the long-chain alkylphenol (dodecylphenol) was also as high as 99.9%.

[0033] Example 2

[0034] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0035] S1: Place 500g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0036] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 30 mol (2823.3 g), the stirring speed is 300 rpm, the heating temperature is 135℃, and the time is 30 min.

[0037] S3: Add high-carbon α-olefin (C14) to the above-mentioned glass reactor, stir and heat. The C14 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 6 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 135℃, and the time is 30 min.

[0038] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 7 wt% (280.1 g) of the total mass of phenol and C14, the stirring speed is 300 rpm, the alkylation reaction temperature is 135℃, and the reaction time is 5 h.

[0039] The long-chain alkylphenol (tetradecylphenol) synthesized in Example 2 was analyzed. At reaction times of 3 h, 4 h, and 5 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that the Beta molecular sieve catalyzed the synthesis of tetradecylphenol with excellent efficiency. At reaction times of 3 h, 4 h, and 5 h, the conversion rates of C14 olefins were 99.7%, 99.8%, and 99.8%, respectively, and the selectivity for the corresponding long-chain alkylphenol (tetradecylphenol) was as high as 99.9%.

[0040] Example 3

[0041] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0042] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0043] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred and heated. The amount of phenol used is 30 mol (2823.3 g), the stirring speed is 250 rpm, the heating temperature is 155℃, and the time is 30 min.

[0044] S3: Add high-carbon α-olefin (C16) to the above-mentioned glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 5 mol (1122.2 g). The stirring speed is 300 rpm, the heating temperature is 155℃, and the time is 30 min.

[0045] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 7 wt% (276.2 g) of the total mass of phenol and C16, the stirring speed is 250 rpm, the alkylation reaction temperature is 155℃, and the reaction time is 6 h.

[0046] The long-chain alkylphenol (hexadecylphenol) synthesized in Example 3 was analyzed. At reaction times of 4 h, 5 h, and 6 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that the Beta molecular sieve catalyzed the synthesis of hexadecylphenol with excellent efficiency. At reaction times of 4 h, 5 h, and 6 h, the conversion rates of C16 olefins were 98.9%, 99.4%, and 99.4%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 98.8%, 99.2%, and 99.2%, respectively.

[0047] Example 4

[0048] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0049] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0050] S2: Place 30 mol (2823.3 g) of phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir at a stirring rate of 300 rpm and heat it to 175°C for 30 min.

[0051] S3: Add high-carbon α-olefin (C18) to the above-mentioned glass reactor, stir and heat. The C18 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 6 mol (1514.9 g). The stirring speed is 300 rpm, the heating temperature is 175℃, and the time is 30 min.

[0052] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 9 wt% (390.4 g) of the total mass of phenol and C18, the stirring speed is 300 rpm, the alkylation reaction temperature is 170℃, and the reaction time is 6 h.

[0053] The long-chain alkylphenol (octadecylphenol) synthesized in Example 4 was analyzed. At reaction times of 4 h, 5 h, and 6 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that the Beta molecular sieve catalyzed the synthesis of octadecylphenol with excellent efficiency. At reaction times of 4 h, 5 h, and 6 h, the conversion rates of C18 olefins were 98.8%, 99.2%, and 99.2%, respectively, and the corresponding selectivities for the long-chain alkylphenol (octadecylphenol) were 97.5%, 97.9%, and 97.9%, respectively.

[0054] Example 5

[0055] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0056] S1: Place 500g of Beta molecular sieve catalyst in an oven and heat it to dry at 110℃ for 10h.

[0057] S2: Place phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The amount of phenol used is 28 mol (2635.1 g), the stirring speed is 300 rpm, the heating temperature is 110℃, and the time is 30 min.

[0058] S3: Add high-carbon α-olefin (C12) to the above-mentioned glass reactor, stir and heat. The C12 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 7 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 110℃, and the time is 30 min.

[0059] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 4 wt% (152.5 g) of the total mass of phenol and C12, the stirring speed is 300 rpm, the alkylation reaction temperature is 110℃, and the reaction time is 4 h.

[0060] The long-chain alkylphenol (dodecylphenol) synthesized in Example 5 was analyzed. At reaction times of 2 h, 3 h, and 4 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 2 h, 3 h, and 4 h, the conversion rates of C12 olefins were 97.6%, 97.9%, and 98.1%, respectively, and the corresponding selectivities for the long-chain alkylphenol (dodecylphenol) were 98.5%, 98.5%, and 98.7%.

[0061] Example 6

[0062] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0063] S1: Place 500g of Beta molecular sieve catalyst in an oven and heat it to dry at 110℃ for 10h.

[0064] S2: Place phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The amount of phenol used is 28 mol (2635.1 g), the stirring speed is 300 rpm, the heating temperature is 110℃, and the time is 30 min.

[0065] S3: Add high-carbon α-olefin (C12) to the above-mentioned glass reactor, stir and heat. The C12 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 7 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 110℃, and the time is 30 min.

[0066] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 6 wt% (228.8 g) of the total mass of phenol and C12, the stirring speed is 300 rpm, the alkylation reaction temperature is 110℃, and the reaction time is 4 h.

[0067] The long-chain alkylphenol (dodecylphenol) synthesized in Example 6 was analyzed. At reaction times of 2 h, 3 h, and 4 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 2 h, 3 h, and 4 h, the conversion rates of C12 olefins were 98.9%, 99.1%, and 99.1%, respectively, and the corresponding selectivities for the long-chain alkylphenol (dodecylphenol) were 97.6%, 98.5%, and 98.5%, respectively.

[0068] Example 7

[0069] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0070] S1: Place 500g of Beta molecular sieve catalyst in an oven and heat it to dry at 110℃ for 10h.

[0071] S2: Place phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The amount of phenol used is 28 mol (2635.1 g), the stirring speed is 300 rpm, the heating temperature is 100℃, and the time is 30 min.

[0072] S3: Add high-carbon α-olefin (C12) to the above-mentioned glass reactor, stir and heat. The C12 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 7 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 100℃, and the time is 30 min.

[0073] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 5 wt% (190.7 g) of the total mass of phenol and C12, the stirring speed is 300 rpm, the alkylation reaction temperature is 100℃, and the reaction time is 4 h.

[0074] The long-chain alkylphenol (dodecylphenol) synthesized in Example 7 was analyzed. At reaction times of 2 h, 3 h, and 4 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 2 h, 3 h, and 4 h, the conversion rates of C12 olefins were 97.3%, 97.9%, and 97.9%, respectively, and the corresponding selectivities for the long-chain alkylphenol (dodecylphenol) were 98.2%, 98.2%, and 98.4%.

[0075] Example 8

[0076] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0077] S1: Place 500g of Beta molecular sieve catalyst in an oven and heat it to dry at 110℃ for 10h.

[0078] S2: Place phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The amount of phenol used is 28 mol (2635.1 g), the stirring speed is 300 rpm, the heating temperature is 120℃, and the time is 30 min.

[0079] S3: Add high-carbon α-olefin (C12) to the above-mentioned glass reactor, stir and heat. The C12 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 7 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 120℃, and the time is 30 min.

[0080] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 5 wt% (190.7 g) of the total mass of phenol and C12, the stirring speed is 300 rpm, the alkylation reaction temperature is 120℃, and the reaction time is 4 h.

[0081] The long-chain alkylphenol (dodecylphenol) synthesized in Example 8 was analyzed. At reaction times of 2 h, 3 h, and 4 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 2 h, 3 h, and 4 h, the conversion rates of C12 olefins were 97.8%, 97.9%, and 97.9%, respectively, and the corresponding selectivities for the long-chain alkylphenol (dodecylphenol) were 98.5%, 98.7%, and 98.7%, respectively.

[0082] Example 9

[0083] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0084] S1: Place 500g of Beta molecular sieve catalyst in an oven and heat it to dry at 110℃ for 10h.

[0085] S2: Place phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The amount of phenol used is 21 mol (1976.3 g), the stirring speed is 300 rpm, the heating temperature is 110℃, and the time is 30 min.

[0086] S3: Add high-carbon α-olefin (C12) to the above-mentioned glass reactor, stir and heat. The C12 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 7 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 110℃, and the time is 30 min.

[0087] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 5 wt% (157.7 g) of the total mass of phenol and C12, the stirring speed is 300 rpm, the alkylation reaction temperature is 110℃, and the reaction time is 4 h.

[0088] The long-chain alkylphenol (dodecylphenol) synthesized in Example 9 was analyzed. At reaction times of 2 h, 3 h, and 4 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 2 h, 3 h, and 4 h, the conversion rates of C12 olefins were 83.1%, 84.5%, and 84.7%, respectively, and the corresponding selectivities for the long-chain alkylphenol (dodecylphenol) were 93.2%, 93.6%, and 93.9%, respectively.

[0089] Example 10

[0090] This embodiment provides a method for synthesizing long-chain alkylphenols using a Beta molecular sieve catalyst, the details of which are as follows:

[0091] S1: Place 500g of Beta molecular sieve catalyst in an oven and heat it to dry at 110℃ for 10h.

[0092] S2: Place phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The amount of phenol used is 35 mol (3293.9 g), the stirring speed is 300 rpm, the heating temperature is 110℃, and the time is 30 min.

[0093] S3: Add high-carbon α-olefin (C12) to the above-mentioned glass reactor, stir and heat. The C12 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 7 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 110℃, and the time is 30 min.

[0094] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 5 wt% (223.6 g) of the total mass of phenol and C12, the stirring speed is 300 rpm, the alkylation reaction temperature is 110℃, and the reaction time is 4 h.

[0095] The long-chain alkylphenol (dodecylphenol) synthesized in Example 10 was analyzed. At reaction times of 2 h, 3 h, and 4 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 2 h, 3 h, and 4 h, the conversion rates of C12 olefins were 99.7%, 99.9%, and 99.9%, respectively, and the selectivity of the long-chain alkylphenol (dodecylphenol) was as high as 99.9% for all of these times.

[0096] Example 11

[0097] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0098] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0099] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 30 mol (2823.3 g), the stirring speed is 300 rpm, the heating temperature is 135℃, and the time is 30 min.

[0100] S3: Add high-carbon α-olefin (C14) to the above-mentioned glass reactor, stir and heat. The C14 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 6 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 135℃, and the time is 30 min.

[0101] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 6 wt% (240.1 g) of the total mass of phenol and C14, the stirring speed is 300 rpm, the alkylation reaction temperature is 135℃, and the reaction time is 5 h.

[0102] The long-chain alkylphenol (tetradecylphenol) synthesized in Example 11 was analyzed. At reaction times of 3 h, 4 h, and 5 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 3 h, 4 h, and 5 h, the conversion rates of C14 olefins were 94.1%, 94.3%, and 94.3%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 97.6%, 97.8%, and 97.8%, respectively.

[0103] Example 12

[0104] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0105] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0106] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 30 mol (2823.3 g), the stirring speed is 300 rpm, the heating temperature is 135℃, and the time is 30 min.

[0107] S3: Add high-carbon α-olefin (C14) to the above-mentioned glass reactor, stir and heat. The C14 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 6 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 135℃, and the time is 30 min.

[0108] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 8 wt% (320.1 g) of the total mass of phenol and C14, the stirring speed is 300 rpm, the alkylation reaction temperature is 135℃, and the reaction time is 5 h.

[0109] The long-chain alkylphenol (tetradecylphenol) synthesized in Example 12 was analyzed. At reaction times of 3 h, 4 h, and 5 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 3 h, 4 h, and 5 h, the conversion rates of C14 olefins were 98.8%, 99.1%, and 99.1%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 98.6%, 98.5%, and 98.5%, respectively.

[0110] Example 13

[0111] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0112] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0113] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 30 mol (2823.3 g), the stirring speed is 300 rpm, the heating temperature is 125℃, and the time is 30 min.

[0114] S3: Add high-carbon α-olefin (C14) to the above-mentioned glass reactor, stir and heat. The C14 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 6 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 125℃, and the time is 30 min.

[0115] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 7 wt% (280.1 g) of the total mass of phenol and C14, the stirring speed is 300 rpm, the alkylation reaction temperature is 125℃, and the reaction time is 5 h.

[0116] The long-chain alkylphenol (tetradecylphenol) synthesized in Example 13 was analyzed. At reaction times of 3 h, 4 h, and 5 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 3 h, 4 h, and 5 h, the conversion rates of C14 olefins were 96.2%, 96.7%, and 96.9%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 98.2%, 98.4%, and 98.4%, respectively.

[0117] Example 14

[0118] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0119] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0120] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 30 mol (2823.3 g), the stirring speed is 300 rpm, the heating temperature is 145℃, and the time is 30 min.

[0121] S3: Add high-carbon α-olefin (C14) to the above-mentioned glass reactor, stir and heat. The C14 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 6 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 145℃, and the time is 30 min.

[0122] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 7 wt% (280.1 g) of the total mass of phenol and C14, the stirring speed is 300 rpm, the alkylation reaction temperature is 145℃, and the reaction time is 5 h.

[0123] The long-chain alkylphenol (tetradecylphenol) synthesized in Example 14 was analyzed. At reaction times of 3 h, 4 h, and 5 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 3 h, 4 h, and 5 h, the conversion rates of C14 olefins were 99.7%, 99.8%, and 99.8%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 98.8%, 98.8%, and 98.2%, respectively.

[0124] Example 15

[0125] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0126] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0127] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 24 mol (2258.6 g), the stirring speed is 300 rpm, the heating temperature is 135℃, and the time is 30 min.

[0128] S3: Add high-carbon α-olefin (C14) to the above-mentioned glass reactor, stir and heat. The C14 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 6 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 135℃, and the time is 30 min.

[0129] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 7 wt% (240.6 g) of the total mass of phenol and C14, the stirring speed is 300 rpm, the alkylation reaction temperature is 135℃, and the reaction time is 5 h.

[0130] The long-chain alkylphenol (tetradecylphenol) synthesized in Example 15 was analyzed. At reaction times of 3 h, 4 h, and 5 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 3 h, 4 h, and 5 h, the conversion rates of C14 olefins were 83.1%, 83.5%, and 83.7%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 89.2%, 89.4%, and 89.4%, respectively.

[0131] Example 16

[0132] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0133] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0134] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 36 mol (3388.0 g), the stirring speed is 300 rpm, the heating temperature is 135℃, and the time is 30 min.

[0135] S3: Add high-carbon α-olefin (C14) to the above-mentioned glass reactor, stir and heat. The C14 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 6 mol (1178.2 g). The stirring speed is 300 rpm, the heating temperature is 135℃, and the time is 30 min.

[0136] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 7 wt% (319.6 g) of the total mass of phenol and C14, the stirring speed is 300 rpm, the alkylation reaction temperature is 135℃, and the reaction time is 5 h.

[0137] The long-chain alkylphenol (tetradecylphenol) synthesized in Example 16 was analyzed. At reaction times of 3 h, 4 h, and 5 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 3 h, 4 h, and 5 h, the conversion rates of C14 olefins were 95.5%, 95.8%, and 95.8%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 98.9%, 99.3%, and 99.1%, respectively.

[0138] Example 17

[0139] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0140] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0141] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred and heated. The amount of phenol used is 30 mol (2823.3 g), the stirring speed is 250 rpm, the heating temperature is 155℃, and the time is 30 min.

[0142] S3: Add high-carbon α-olefin (C16) to the above-mentioned glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 5 mol (1122.2 g). The stirring speed is 300 rpm, the heating temperature is 155℃, and the time is 30 min.

[0143] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 6 wt% (236.7 g) of the total mass of phenol and C16, the stirring speed is 250 rpm, the alkylation reaction temperature is 155℃, and the reaction time is 6 h.

[0144] The long-chain alkylphenol (hexadecylphenol) synthesized in Example 17 was analyzed. At reaction times of 4 h, 5 h, and 6 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 4 h, 5 h, and 6 h, the conversion rates of C16 olefins were 92.3%, 92.4%, and 92.4%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 95.8%, 96.0%, and 96.0%, respectively.

[0145] Example 18

[0146] This embodiment provides a method for synthesizing long-chain alkylphenols using Beta molecular sieve catalysis, the details of which are as follows:

[0147] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0148] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred and heated. The amount of phenol used is 30 mol (2823.3 g), the stirring speed is 250 rpm, the heating temperature is 155℃, and the time is 30 min.

[0149] S3: Add high-carbon α-olefin (C16) to the above-mentioned glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 5 mol (1122.2 g). The stirring speed is 300 rpm, the heating temperature is 155℃, and the time is 30 min.

[0150] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 8 wt% (315.6 g) of the total mass of phenol and C16, the stirring speed is 250 rpm, the alkylation reaction temperature is 155℃, and the reaction time is 6 h.

[0151] The long-chain alkylphenol (hexadecylphenol) synthesized in Example 18 was analyzed. At reaction times of 4 h, 5 h, and 6 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 4 h, 5 h, and 6 h, the conversion rates of C16 olefins were 97.9%, 98.2%, and 98.2%, respectively, and the corresponding selectivities of the long-chain alkylphenol (hexadecylphenol) were 97.8%, 98.0%, and 98.0%, respectively.

[0152] Example 19

[0153] This embodiment provides a method for synthesizing long-chain alkylphenols using a Beta molecular sieve catalyst, the details of which are as follows:

[0154] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0155] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 30 mol (2823.3 g), the stirring speed is 250 rpm, the heating temperature is 145℃, and the time is 30 min.

[0156] S3: Add high-carbon α-olefin (C16) to the above-mentioned glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 5 mol (1122.2 g). The stirring speed is 300 rpm, the heating temperature is 145℃, and the time is 30 min.

[0157] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 7 wt% (276.2 g) of the total mass of phenol and C16, the stirring speed is 250 rpm, the alkylation reaction temperature is 145℃, and the reaction time is 6 h.

[0158] The long-chain alkylphenol (hexadecylphenol) synthesized in Example 19 was analyzed. At reaction times of 4 h, 5 h, and 6 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 4 h, 5 h, and 6 h, the conversion rates of C16 olefins were 95.9%, 96.2%, and 96.2%, respectively, and the corresponding selectivities of the long-chain alkylphenol (hexadecylphenol) were 97.9%, 98.2%, and 98.2%, respectively.

[0159] Example 20

[0160] This embodiment provides a method for synthesizing long-chain alkylphenols using a Beta molecular sieve catalyst, the details of which are as follows:

[0161] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0162] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 30 mol (2823.3 g), the stirring speed is 250 rpm, the heating temperature is 165℃, and the time is 30 min.

[0163] S3: Add high-carbon α-olefin (C16) to the above-mentioned glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 5 mol (1122.2 g), a stirring speed of 300 rpm, a heating temperature of 165℃, and a heating time of 30 min.

[0164] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 7 wt% (276.2 g) of the total mass of phenol and C16, the stirring speed is 250 rpm, the alkylation reaction temperature is 165℃, and the reaction time is 6 h.

[0165] The long-chain alkylphenol (hexadecylphenol) synthesized in Example 20 was analyzed. At reaction times of 4 h, 5 h, and 6 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 4 h, 5 h, and 6 h, the conversion rates of C16 olefins were 97.9%, 98.1%, and 98.1%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 98.4%, 98.3%, and 98.3%, respectively.

[0166] Example 21

[0167] This embodiment provides a method for synthesizing long-chain alkylphenols using a Beta molecular sieve catalyst, the details of which are as follows:

[0168] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0169] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 25 mol (2352.8 g), the stirring speed is 250 rpm, the heating temperature is 155℃, and the time is 30 min.

[0170] S3: Add high-carbon α-olefin (C16) to the above-mentioned glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 5 mol (1122.2 g). The stirring speed is 300 rpm, the heating temperature is 155℃, and the time is 30 min.

[0171] S4: The dried Beta molecular sieve catalyst from step S1 is added to the glass reactor described above, stirred and heated to carry out the alkylation reaction, thereby obtaining long-chain alkylphenols. The amount of Beta molecular sieve catalyst used is 7 wt% (243.3 g) of the total mass of phenol and C16, the stirring speed is 250 rpm, the alkylation reaction temperature is 155℃, and the reaction time is 6 h.

[0172] The long-chain alkylphenol (hexadecylphenol) synthesized in Example 21 was analyzed. At reaction times of 4 h, 5 h, and 6 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 4 h, 5 h, and 6 h, the conversion rates of C16 olefins were 80.1%, 80.4%, and 80.4%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 89.7%, 90.3%, and 90.3%, respectively.

[0173] Example 22

[0174] This embodiment provides a method for synthesizing long-chain alkylphenols using a Beta molecular sieve catalyst, the details of which are as follows:

[0175] S1: Place 600g of Beta molecular sieve catalyst in an oven and heat to dry. The heating temperature is 110℃, and the holding time is 10h.

[0176] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 35 mol (3293.9 g), the stirring speed is 250 rpm, the heating temperature is 155℃, and the time is 30 min.

[0177] S3: Add high-carbon α-olefin (C16) to the above-mentioned glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company, with an addition amount of 5 mol (1122.2 g). The stirring speed is 300 rpm, the heating temperature is 155℃, and the time is 30 min.

[0178] S4: Add the Beta molecular sieve catalyst to the glass reactor described above, stir and heat to carry out the alkylation reaction, and long-chain alkylphenols can be obtained. The amount of Beta molecular sieve catalyst used is 7 wt% (309.1 g) of the total mass of phenol and C16, the stirring speed is 250 rpm, the alkylation reaction temperature is 155℃, and the time is 6 h.

[0179] In Example 22, the synthesized long-chain alkylphenol (hexadecylphenol) was analyzed. At reaction times of 4 h, 5 h, and 6 h, 1 mL of sample was taken, followed by the addition of 2 mL of dichloromethane. After shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The results showed that at reaction times of 4 h, 5 h, and 6 h, the conversion rates of C16 olefins were 97.9%, 98.3%, and 98.3%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 97.5%, 98.0%, and 98.0%, respectively.

[0180] In summary, the method for synthesizing long-chain alkylphenols using Beta molecular sieve catalyst of the present invention, employing Beta molecular sieve as the catalyst, is not only environmentally friendly and meets the requirements of modern green chemical engineering compared to traditional liquid acid catalysts, but also easily separated after the reaction, facilitating catalyst recycling. Analysis results show that the conversion rates of C12-C18 high-carbon α-olefins are as high as 99.9% (C12), 99.8% (C14), 99.4% (C16), and 99.2% (C18), respectively, with corresponding selectivity of long-chain alkylphenols reaching 99.9% (C12), 99.9% (C14), 99.2% (C16), and 97.9% (C18), respectively.

[0181] Any numerical value mentioned in this invention, if there is only a two-unit interval between any minimum and any maximum value, includes all values ​​that increase by one unit each time from the minimum to the maximum value. For example, if the amount of a component, or the value of a process variable such as temperature, pressure, or time, is stated as 50-90, in this specification it means specifically listing values ​​such as 51-89, 52-88… and 69-71 and 70-71, etc. For non-integer values, it may be appropriately considered that a unit is 0.1, 0.01, 0.001, or 0.0001. These are merely some specifically specified examples. In this application, in a similar manner, all possible combinations of numerical values ​​between the listed minimum and maximum values ​​are considered to have been disclosed.

[0182] It should be noted that the embodiments described above are only for explaining the present invention and do not constitute any limitation on the present invention. The present invention has been described with reference to typical embodiments, but it should be understood that the words used therein are descriptive and explanatory terms, not limiting terms. Modifications can be made to the present invention within the scope of the claims, and revisions can be made to the present invention without departing from the scope and spirit of the present invention. Although the present invention described herein relates to specific methods, materials, and embodiments, it does not mean that the present invention is limited to the specific examples disclosed herein; on the contrary, the present invention can be extended to all other methods and applications with the same function.

Claims

1. A process for the preparation of long chain alkyl phenols using Beta molecular sieve as catalyst, characterized by, Includes the following steps: S1: Dry the Beta molecular sieve to obtain the dried Beta molecular sieve; S2: Phenol is heated and stirred to melt, resulting in liquid phenol; S3: Add the α-olefin to the phenol liquid obtained in step S2, heat and stir to obtain a mixture; the α-olefin is a C12-C18 olefin; S4: The dried Beta molecular sieve obtained in step S1 is added to the mixture obtained in step S3 to carry out an alkylation reaction to obtain a long-chain alkylphenol; In step S1, the molar ratio of SiO2 to Al2O3 in the Beta molecular sieve is 15.

2. The method of claim 1, wherein, In step S1, the drying conditions are: temperature 100-140℃, time 2-13 h.

3. The method of claim 1, wherein, In step S2, the stirring rate is 50-500 rpm, the heating temperature is 100-170℃, and the heating time is 5-50 min.

4. The method according to any one of claims 1 to 3, characterized in that, In step S3, the molar ratio of the added α-olefin to phenol is 1:(3-8).

5. The method of claim 4, wherein, The stirring rate in step S3 is 50-500 rpm, and the heating temperature is 100-170℃.

6. The method of claim 4, wherein, In step S4, the amount of Beta molecular sieve used is 1-10 wt% of the total mass of phenol and α-olefin.

7. The method of claim 6, wherein, The conditions for the alkylation reaction in step S4 are: alkylation reaction temperature of 100-170℃ and reaction time of 2-8 h.

8. The method of claim 7, wherein, The alkylation reaction in step S4 is carried out with stirring at 50-500 rpm.

9. The method according to any one of claims 6-8, characterized in that, For the synthesis of dodecylphenol, the amount of Beta molecular sieve catalyst used is 4-6 wt% of the total mass of phenol and C12 olefins; For the synthesis of tetradecylphenol, the amount of Beta molecular sieve catalyst used is 6-8 wt% of the total mass of phenol and C14 olefins; For the synthesis of hexadecylphenol, the amount of Beta molecular sieve catalyst used is 6-8 wt% of the total mass of phenol and C16 olefins; For the synthesis of octadecylphenol, the amount of Beta molecular sieve catalyst used is 8-10 wt% of the total mass of phenol and C18 olefins.

10. The method according to any one of claims 1-3, 5-8, characterized in that, The method further includes: mixing long-chain alkylphenols and dichloromethane evenly and injecting the mixture into a gas chromatograph for detection and analysis.