Synthesis method and analysis method of long-chain alkyl phenol catalyzed by MCM-22 molecular sieve

Abstract

This invention proposes a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieve. Using phenol and high-carbon α-olefins (C12-C18) as raw materials, the long-chain alkylphenols are synthesized under specific conditions and at a certain temperature. Gas chromatography is then used to analyze the prepared long-chain alkylphenols. This synthesis method can synthesize long-chain alkylphenols with high selectivity and high conversion rates, and the reaction conditions are mild and controllable.

Description

Technical Field

[0001] This invention belongs to the field of long-chain alkylphenol synthesis technology, specifically relating to a method for synthesizing and analyzing long-chain alkylphenols catalyzed by MCM-22 molecular sieve. 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 catalyzed by MCM-22 molecular sieves.

[0006] In a first aspect, the present invention proposes a method for synthesizing long-chain alkylphenols catalyzed by MCM-22 molecular sieves, comprising the following steps:

[0007] S1: Dry the MCM-22 molecular sieve catalyst to obtain the dried MCM-22 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, stir and heat to obtain a mixture;

[0010] S4: The dried MCM-22 molecular sieve catalyst from step S1 is added to the mixture obtained in step S3, and the mixture is stirred and heated to carry out an alkylation reaction to obtain a long-chain alkylphenol.

[0011] As a specific embodiment of the present invention, in step S1, the MCM-22 molecular sieve catalyst is selected from MCM-22 molecular sieves in which the molar ratio of SiO2 to Al2O3 is 15.

[0012] And / or, the drying temperature is 90-140℃, and the holding time is 3-15h. Drying continues until the catalyst mass remains constant.

[0013] In a specific embodiment of the present invention, in step S2, the stirring rate is 50-500 rpm, the heating temperature is 90-180℃, and the holding time is 5-50 min.

[0014] As a specific embodiment of the present invention, in step S3, the high carbon α-olefin is C12-C18 and is obtained from the LAO unit of Sinopec Maoming Petrochemical Company.

[0015] And / or, the molar ratio of the high carbon α-olefin to phenol is 1:(3-10);

[0016] And / or, the stirring rate is 50-500 rpm, the heating temperature is 90-180℃, and the holding time is 5-50 min.

[0017] In a specific embodiment of the present invention, in step S4, the amount of the molecular sieve catalyst MCM-22 is 3-10 wt% based on the total mass of high carbon α-olefins and phenol; wherein, for the synthesis of dodecylphenol, the amount of MCM-22 molecular sieve catalyst is 5-7 wt% of the total mass of phenol and C12; for the synthesis of tetradecylphenol, the amount of MCM-22 molecular sieve catalyst is 4-6 wt% of the total mass of phenol and C14; for the synthesis of hexadecylphenol, the amount of MCM-22 molecular sieve catalyst is 6-8 wt% of the total mass of phenol and C16; and for the synthesis of octadecylphenol, the amount of MCM-22 molecular sieve catalyst is 8-10 wt% of the total mass of phenol and C18.

[0018] And / or, the stirring rate is 50-500 rpm, the alkylation reaction temperature is 90-180℃, and the reaction time is 1-7 h.

[0019] Secondly, the present invention provides an analytical method for synthesizing long-chain alkylphenols by a method catalyzing the synthesis of long-chain alkylphenols using MCM-22 molecular sieve catalysis, comprising: mixing the long-chain alkylphenols synthesized by the method catalyzing the synthesis of long-chain alkylphenols using MCM-22 molecular sieve catalysis with dichloromethane and injecting the mixture into a gas chromatograph for detection and analysis.

[0020] As a specific embodiment of the present invention, dichloromethane can effectively disperse long-chain alkylphenol reaction solutions.

[0021] 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.

[0022] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0023] 1. The method for synthesizing long-chain alkylphenols catalyzed by MCM-22 molecular sieve provided by the present invention uses MCM-22 molecular sieve 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.

[0024] 2. The method for synthesizing long-chain alkylphenols catalyzed by MCM-22 molecular sieve provided by the present invention, after detection and analysis of the long-chain alkylphenols obtained in each embodiment, shows that the conversion rates of C12-C18 high carbon α-olefins are as high as 99.9% (C12), 99.9% (C14), 99.3% (C16) and 99.0% (C18), respectively, and the corresponding selectivity of long-chain alkylphenols are as high as 99.9% (C12), 99.8% (C14), 98.7% (C16) and 96.5% (C18), respectively. Detailed Implementation

[0025] The present invention will be further described below with reference to specific embodiments, but this does not constitute any limitation on the present invention.

[0026] The molar ratio of SiO2 to Al2O3 in the MCM-22 molecular sieve catalyst used in the various embodiments of the present invention is 15; it was purchased from Dalian Molecular Sieve Factory.

[0027] Example 1

[0028] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0029] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 100℃ for 12 hours;

[0030] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 32 mol (3011.5 g), the stirring speed is 250 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0031] 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 8 mol (1346.6 g). The stirring speed is 200 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0032] S4: 6 wt% (261.5 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor mentioned above. The reactor was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 100℃, and the reaction time was 4 h to obtain long-chain alkylphenols.

[0033] The long-chain alkylphenol (dodecylphenol) synthesized in Example 1 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 2 h, 3 h, and 4 h, respectively. Then, 2 mL of dichloromethane was added, and after shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The analysis results showed that the MCM-22 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 of the long-chain alkylphenol (dodecylphenol) was also as high as 99.9%.

[0034] Example 2

[0035] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0036] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0037] 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 and heat it. The stirring rate is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0038] S3: Add 5 mol (981.9 g) of high-carbon α-olefin (C14) to the above glass reactor, stir and heat. The C14 is obtained from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0039] S4: 5 wt% (190.3 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the reaction was carried out by stirring and heating. The stirring rate was 250 rpm, the alkylation reaction temperature was 110 °C, and the reaction time was 5 h to obtain long-chain alkylphenols.

[0040] 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 MCM-22 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%, 99.9%, and 99.9%, respectively, and the selectivity for the corresponding long-chain alkylphenol (tetradecylphenol) was as high as 99.8%.

[0041] Example 3

[0042] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0043] S1: Place 600g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0044] S2: Place 32 mol (3011.5 g) of phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The stirring rate is 250 rpm, the heating temperature is 140℃, and the holding time is 30 min.

[0045] S3: Add 4 mol (897.7 g) of high-carbon α-olefin (C16) to the above glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 140℃, and the holding time is 30 min.

[0046] S4: 7 wt% (273.6 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor mentioned above. The reactor was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 140℃, and the reaction time was 6 h to obtain long-chain alkylphenols.

[0047] 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 MCM-22 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 98.7%, 99.3%, and 99.3%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 98.4%, 98.7%, and 98.7%, respectively.

[0048] Example 4

[0049] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0050] S1: Place 600g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0051] 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 and heat it. The stirring rate is 250 rpm, the heating temperature is 170℃, and the holding time is 30 min.

[0052] S3: Add 6 mol (1514.9 g) of high carbon α-olefin (C18) to the glass reactor, stir and heat. The C18 is from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 170℃, and the holding time is 30 min.

[0053] S4: 9 wt% (390.4 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor of step S3, and the mixture was stirred and heated to carry out the alkylation reaction. The stirring rate was 250 rpm, the alkylation reaction temperature was 170 °C, and the reaction time was 6 h to obtain long-chain alkylphenols.

[0054] The long-chain alkylphenol (octadecylphenol) synthesized in Example 4 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 4 h, 5 h, and 6 h, respectively. Then, 2 mL of dichloromethane was added, and after shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The analysis results showed that the MCM-22 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 98.5%, 99.0%, and 99.0%, respectively, and the corresponding selectivities of the long-chain alkylphenol (octadecylphenol) were 95.5%, 96.5%, and 96.5%, respectively.

[0055] Example 5

[0056] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0057] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 100℃ for 12 hours;

[0058] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 32 mol (3011.5 g), the stirring speed is 250 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0059] 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 8 mol (1346.6 g). The stirring speed is 200 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0060] S4: 5 wt% (217.9 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the mixture was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 100℃, and the reaction time was 4 h to obtain long-chain alkylphenols.

[0061] The long-chain alkylphenol (dodecylphenol) synthesized in Example 5 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 2 h, 3 h, and 4 h, respectively. Then, 2 mL of dichloromethane was added, and after shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The analysis results showed that the conversion rates of C12 olefins at reaction times of 2 h, 3 h, and 4 h were 97.5%, 97.9%, and 97.9%, respectively, and the corresponding selectivities of the long-chain alkylphenol (dodecylphenol) were 98.9%, 99.4%, and 99.4%, respectively.

[0062] Example 6

[0063] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0064] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 100℃ for 12 hours;

[0065] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 32 mol (3011.5 g), the stirring speed is 250 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0066] 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 8 mol (1346.6 g). The stirring speed is 200 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0067] S4: 5 wt% (305.1 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the mixture was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 100℃, and the reaction time was 4 h to obtain long-chain alkylphenols.

[0068] The long-chain alkylphenol (dodecylphenol) synthesized in Example 6 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 2 h, 3 h, and 4 h, respectively. Then, 2 mL of dichloromethane was added, and after shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The analysis results showed that the conversion rates of C12 olefins at reaction times of 2 h, 3 h, and 4 h were 99.6%, 99.8%, and 99.8%, respectively, and the corresponding selectivities of the long-chain alkylphenol (dodecylphenol) were 99.9%, 99.7%, and 99.7%, respectively.

[0069] Example 7

[0070] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0071] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 100℃ for 12 hours;

[0072] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 32 mol (3011.5 g), the stirring speed is 250 rpm, the heating temperature is 90℃, and the holding time is 30 min.

[0073] 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 8 mol (1346.6 g). The stirring speed is 200 rpm, the heating temperature is 90℃, and the holding time is 30 min.

[0074] S4: 6 wt% (261.5 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the mixture was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 90℃, and the reaction time was 4 h to obtain long-chain alkylphenols.

[0075] The long-chain alkylphenol (dodecylphenol) synthesized in Example 7 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 2 h, 3 h, and 4 h, respectively. Then, 2 mL of dichloromethane was added, and after shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The analysis results showed that the conversion rates of C12 olefins at reaction times of 2 h, 3 h, and 4 h were 95.7%, 96.1%, and 96.3%, respectively, and the corresponding selectivities of the long-chain alkylphenol (dodecylphenol) were 98.8%, 99.1%, and 99.2%, respectively.

[0076] Example 8

[0077] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0078] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 100℃ for 12 hours;

[0079] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 32 mol (3011.5 g), the stirring speed is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0080] 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, and the amount of C12 added is 8 mol (1346.6 g). The stirring speed is 200 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0081] S4: 6 wt% (261.5 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the mixture was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 110℃, and the reaction time was 4 h to obtain long-chain alkylphenols.

[0082] The long-chain alkylphenol (dodecylphenol) synthesized in Example 8 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 2 h, 3 h, and 4 h, respectively. Then, 2 mL of dichloromethane was added, and after shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The analysis results showed that the conversion rates of C12 olefins were 99.7%, 99.9%, and 99.9% at reaction times of 2 h, 3 h, and 4 h, respectively, and the corresponding selectivities of the long-chain alkylphenol (dodecylphenol) were 99.8%, 99.5%, and 99.5%, respectively.

[0083] Example 9

[0084] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0085] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 100℃ for 12 hours;

[0086] 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 250 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0087] 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 8 mol (1346.6 g). The stirring speed is 200 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0088] S4: 6 wt% (216.3 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the mixture was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 100℃, and the reaction time was 4 h to obtain long-chain alkylphenols.

[0089] The long-chain alkylphenol (dodecylphenol) synthesized in Example 9 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 2 h, 3 h, and 4 h, respectively. Then, 2 mL of dichloromethane was added, and after shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The analysis results showed that the conversion rates of C12 olefins at reaction times of 2 h, 3 h, and 4 h were 94.3%, 94.7%, and 94.9%, respectively, and the corresponding selectivities of the long-chain alkylphenol (dodecylphenol) were 97.8%, 98.1%, and 98.1%, respectively.

[0090] Example 10

[0091] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0092] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 100℃ for 12 hours;

[0093] S2: Phenol is heated in an oven until melted, then added to a glass reactor, stirred, and heated. The amount of phenol used is 40 mol (3764.4 g), the stirring speed is 250 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0094] 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 8 mol (1346.6 g). The stirring speed is 200 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0095] S4: 6 wt% (306.7 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor mentioned above. The reactor was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 100℃, and the reaction time was 4 h to obtain long-chain alkylphenols.

[0096] The long-chain alkylphenol (dodecylphenol) synthesized in Example 10 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 2 h, 3 h, and 4 h, respectively. Then, 2 mL of dichloromethane was added, and after shaking, 2 μL of the sample was injected into a gas chromatograph for detection. The analysis results showed that the conversion rates of C12 olefins at reaction times of 2 h, 3 h, and 4 h were 99.7%, 99.8%, and 99.8%, respectively, and the corresponding selectivities of the long-chain alkylphenol (dodecylphenol) were 99.6%, 99.8%, and 99.8%, respectively.

[0097] Example 11

[0098] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0099] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0100] 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 and heat it. The stirring rate is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0101] S3: Add 5 mol (981.9 g) of high-carbon α-olefin (C14) to the above glass reactor, stir and heat. The C14 is obtained from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0102] S4: 4 wt% (152.2 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the reaction was carried out by stirring and heating. The stirring rate was 250 rpm, the alkylation reaction temperature was 110 °C, and the reaction time was 5 h to obtain long-chain alkylphenols.

[0103] 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 96.6%, 97.1%, and 97.3%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 98.2%, 98.5%, and 98.5%, respectively.

[0104] Example 12

[0105] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0106] S1: Place 500g of molecular sieve catalyst MCM-22 in an oven and heat it at 110℃ for 12 hours;

[0107] 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 and heat it. The stirring rate is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0108] S3: Add 5 mol (981.9 g) of high-carbon α-olefin (C14) to the above glass reactor, stir and heat. The C14 is obtained from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0109] S4: 6 wt% (228.3 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the reaction was carried out by stirring and heating. The stirring rate was 250 rpm, the alkylation reaction temperature was 110 °C, and the reaction time was 5 h to obtain long-chain alkylphenols.

[0110] 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 99.6%, 99.7%, and 99.8%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 99.6%, 99.7%, and 99.7%, respectively.

[0111] Example 13

[0112] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0113] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0114] 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 and heat it. The stirring rate is 250 rpm, the heating temperature is 100℃, and the holding time is 30 min.

[0115] S3: Add 5 mol (981.9 g) of high-carbon α-olefin (C14) to the above glass reactor, stir and heat. The C14 was obtained from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate was 250 rpm, the heating temperature was 100℃, and the holding time was 30 min.

[0116] S4: 5 wt% (190.3 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the reaction was carried out by stirring and heating. The stirring rate was 250 rpm, the alkylation reaction temperature was 100℃, and the reaction time was 5 h to obtain long-chain alkylphenols.

[0117] 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 94.8%, 95.4%, and 95.7%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 97.8%, 98.1%, and 98.1%, respectively.

[0118] Example 14

[0119] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0120] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0121] 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 and heat it. The stirring rate is 250 rpm, the heating temperature is 120℃, and the holding time is 30 min.

[0122] S3: Add 5 mol (981.9 g) of high-carbon α-olefin (C14) to the above glass reactor, stir and heat. The C14 was obtained from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate was 250 rpm, the heating temperature was 120℃, and the holding time was 30 min.

[0123] S4: 5 wt% (190.3 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the reaction was carried out by stirring and heating. The stirring rate was 250 rpm, the alkylation reaction temperature was 120 °C, and the reaction time was 5 h to obtain long-chain alkylphenols.

[0124] 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 99.6%, 99.8%, and 99.8%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 99.7%, 99.5%, and 99.5%, respectively.

[0125] Example 15

[0126] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0127] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0128] S2: Place 25 mol (2352.8 g) of phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The stirring rate is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0129] S3: Add 5 mol (981.9 g) of high-carbon α-olefin (C14) to the above glass reactor, stir and heat. The C14 is obtained from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0130] S4: 5 wt% (166.7 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the mixture was stirred and heated to carry out the alkylation reaction. The stirring rate was 250 rpm, the alkylation reaction temperature was 110 °C, and the reaction time was 5 h to obtain long-chain alkylphenols.

[0131] 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 96.3%, 96.6%, and 96.6%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 98.1%, 98.3%, and 98.3%, respectively.

[0132] Example 16

[0133] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0134] S1: Place 500g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0135] S2: Place 35 mol (3293.9 g) of phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The stirring rate is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0136] S3: Add 5 mol (981.9 g) of high-carbon α-olefin (C14) to the above glass reactor, stir and heat. The C14 is obtained from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 110℃, and the holding time is 30 min.

[0137] S4: 5 wt% (213.8 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the reaction was carried out by stirring and heating. The stirring rate was 250 rpm, the alkylation reaction temperature was 110 °C, and the reaction time was 5 h to obtain long-chain alkylphenols.

[0138] 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 98.9%, 99.3%, and 99.5%, respectively, and the corresponding selectivities for the long-chain alkylphenol (tetradecylphenol) were 99.2%, 99.5%, and 99.6%.

[0139] Example 17

[0140] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0141] S1: Place 600g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0142] S2: Place 32 mol (3011.5 g) of phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The stirring rate is 250 rpm, the heating temperature is 140℃, and the holding time is 30 min.

[0143] S3: Add 4 mol (897.7 g) of high-carbon α-olefin (C16) to the above glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 140℃, and the holding time is 30 min.

[0144] S4: 6 wt% (234.5 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the mixture was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 140℃, and the reaction time was 6 h to obtain long-chain alkylphenols.

[0145] 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 96.4%, 96.8%, and 96.8%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 96.2%, 96.5%, and 96.5%, respectively.

[0146] Example 18

[0147] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0148] S1: Place 600g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0149] S2: Place 32 mol (3011.5 g) of phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The stirring rate is 250 rpm, the heating temperature is 140℃, and the holding time is 30 min.

[0150] S3: Add 4 mol (897.7 g) of high-carbon α-olefin (C16) to the above glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 140℃, and the holding time is 30 min.

[0151] S4: 8 wt% (312.7 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor mentioned above. The reactor was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 140℃, and the reaction time was 6 h to obtain long-chain alkylphenols.

[0152] 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 98.5%, 98.9%, and 98.9%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 98.3%, 98.4%, and 98.4%, respectively.

[0153] Example 19

[0154] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0155] S1: Place 600g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0156] S2: Place 32 mol (3011.5 g) of phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The stirring rate is 250 rpm, the heating temperature is 130℃, and the holding time is 30 min.

[0157] S3: Add 4 mol (897.7 g) of high-carbon α-olefin (C16) to the above glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 130℃, and the holding time is 30 min.

[0158] S4: 7 wt% (273.6 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the mixture was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 130℃, and the reaction time was 6 h to obtain long-chain alkylphenols.

[0159] 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 95.6%, 95.9%, and 95.9%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 96.2%, 96.4%, and 96.4%, respectively.

[0160] Example 20

[0161] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0162] S1: Place 600g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0163] S2: Place 32 mol (3011.5 g) of phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The stirring rate is 250 rpm, the heating temperature is 150℃, and the holding time is 30 min.

[0164] S3: Add 4 mol (897.7 g) of high-carbon α-olefin (C16) to the above glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 150℃, and the holding time is 30 min.

[0165] S4: 7 wt% (273.6 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor mentioned above. The reactor was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 150℃, and the reaction time was 6 h to obtain long-chain alkylphenols.

[0166] 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 98.2%, 98.5%, and 98.6%, respectively, and the corresponding selectivities of the long-chain alkylphenol (hexadecylphenol) were 98.3%, 98.4%, and 98.4%, respectively.

[0167] Example 21

[0168] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0169] S1: Place 600g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0170] S2: Place 36 mol (3388.0 g) of phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The stirring speed is 250 rpm, the heating temperature is 140℃, and the holding time is 30 min.

[0171] S3: Add 4 mol (897.7 g) of high-carbon α-olefin (C16) to the above glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 140℃, and the holding time is 30 min.

[0172] S4: 7 wt% (300.0 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor above, and the mixture was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 140℃, and the reaction time was 6 h to obtain long-chain alkylphenols.

[0173] 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 98.6%, 99.1%, and 99.1%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 98.1%, 98.3%, and 98.3%, respectively.

[0174] Example 22

[0175] This embodiment provides a method for the synthesis and analysis of long-chain alkylphenols catalyzed by MCM-22 molecular sieves, the details of which are as follows:

[0176] S1: Place 600g of MCM-22 molecular sieve catalyst in an oven and heat it at 110℃ for 12 hours;

[0177] S2: Place 28 mol (2635.1 g) of phenol in an oven and heat it until it melts. Then add it to a glass reactor, stir and heat it. The stirring rate is 250 rpm, the heating temperature is 140℃, and the holding time is 30 min.

[0178] S3: Add 4 mol (897.7 g) of high-carbon α-olefin (C16) to the above glass reactor, stir and heat. The C16 is sourced from the LAO unit of Sinopec Maoming Petrochemical Company. The stirring rate is 250 rpm, the heating temperature is 140℃, and the holding time is 30 min.

[0179] S4: 7 wt% (247.3 g) of MCM-22 molecular sieve catalyst based on the total mass of high carbon α-olefins and phenol was added to the glass reactor mentioned above. The reactor was stirred and heated to carry out the alkylation reaction. The stirring speed was 250 rpm, the alkylation reaction temperature was 140℃, and the reaction time was 6 h to obtain long-chain alkylphenols.

[0180] 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 96.8%, 97.2%, and 97.2%, respectively, and the corresponding selectivities for the long-chain alkylphenol (hexadecylphenol) were 97.1%, 97.3%, and 97.3%, respectively.

[0181] In summary, the method for synthesizing long-chain alkylphenols using MCM-22 molecular sieve catalysis of the present invention, employing MCM-22 molecular sieve as a catalyst, yields long-chain alkylphenols with conversion rates of up to 99.9% (C12), 99.9% (C14), 99.6% (C16), and 99.1% (C18) for C12-C18 high-carbon α-olefins, respectively. Correspondingly, the selectivity of the long-chain alkylphenols is as high as 99.9% (C12), 99.8% (C14), 99.1% (C16), and 97.3% (C18), respectively.

[0182] 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.

[0183] 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 method for synthesizing long-chain alkylphenols catalyzed by MCM-22 molecular sieve, characterized in that, Includes the following steps: S1: Dry the MCM-22 molecular sieve catalyst to obtain the dried MCM-22 molecular sieve; S2: Phenol is heated and stirred to melt, resulting in liquid phenol; S3: Add a high-carbon α-olefin to the phenol liquid obtained in step S2, stir and heat to obtain a mixture; the high-carbon α-olefin is a C12-C18 olefin; S4: The dried MCM-22 molecular sieve catalyst from step S1 is added to the mixture obtained in step S3, and the mixture is stirred and heated to carry out an alkylation reaction to obtain a long-chain alkylphenol. In step S1, the MCM-22 molecular sieve catalyst is selected from MCM-22 molecular sieves in which the molar ratio of SiO2 to Al2O3 is 15.

2. The synthesis method according to claim 1, characterized in that, In step S1, the drying temperature is 90-140℃.

3. The synthesis method according to claim 1, characterized in that, In step S2, the stirring rate is 50-500 rpm and the heating temperature is 90-180℃.

4. The synthesis method according to any one of claims 1-3, characterized in that, In step S3, the molar ratio of the high carbon α-olefin to phenol is 1:(3-10).

5. The synthesis method according to claim 4, characterized in that, In step S3, the stirring rate is 50-500 rpm and the heating temperature is 90-180℃.

6. The synthesis method according to claim 4, characterized in that, In step S4, the amount of the MCM-22 molecular sieve catalyst used is 3-10 wt% based on the total mass of high carbon α-olefins and phenol.

7. The synthesis method according to claim 6, characterized in that, In step S4, the stirring rate is 50-500 rpm, the alkylation reaction temperature is 90-180℃, and the reaction time is 1-7 h.

8. The synthesis method according to claim 6 or 7, characterized in that, In step S4, for the synthesis of dodecylphenol, the amount of MCM-22 molecular sieve catalyst used is 5-7 wt% of the total mass of phenol and C12 olefins. For the synthesis of tetradecylphenol, the amount of MCM-22 molecular sieve catalyst used is 4-6 wt% of the total mass of phenol and C14 olefins; For the synthesis of hexadecylphenol, the amount of MCM-22 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 MCM-22 molecular sieve catalyst used is 8-10 wt% of the total mass of phenol and C18 olefins.