Synthesis method and analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve

Abstract

The application provides a synthesis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve, and the method for synthesizing long-chain alkyl phenol catalyzed by X zeolite molecular sieve provided by the application selects X zeolite molecular sieve as a catalyst, compared with a traditional liquid acid catalyst, is not only environment-friendly, meets the requirements of modern green chemical industry, but also is easy to separate after reaction, and is beneficial to the recycling use of the catalyst. The results show that the conversion rates of C12-C18 high-carbon alpha-olefins are respectively 99.9% (C12), 99.9% (C14), 99.6% (C16) and 99.1% (C18), and the selectivities of the corresponding long-chain alkyl phenols are respectively 99.9% (C12), 99.8% (C14), 99.1% (C16) and 97.3% (C18).

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of long-chain alkyl phenol synthesis, and particularly relates to a synthesis method and an analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve. BACKGROUND

[0002] Long-chain alkyl phenol is an important chemical product, raw material and intermediate, and is widely used in the synthesis of fine chemicals. Long-chain alkyl phenol is mainly prepared by the reaction of phenol and high-carbon normal alkane, high-carbon normal alcohol or high-carbon alpha-olefin. Since halogen needs to be introduced in the alkylation process of high-carbon normal alkane or alcohol, the process difficulty is increased, and the economic benefit is poor, so high-carbon alpha-olefin is used as the main alkyl source in the production process of alkyl phenol.

[0003] At present, long-chain alkyl phenol is mainly prepared by the alkylation reaction of olefin and phenol catalyzed by traditional liquid acid such as HF and AlCl3 in industrial production, but this method has many problems such as many impurities and side reactions, serious equipment corrosion, complex product post-treatment and serious environmental pollution. With the increasing environmental awareness of human beings, environmentally friendly chemical reaction processes have attracted widespread attention.

[0004] Therefore, it is of great significance to seek a new type of catalyst to green this process route for the sustainable development of chemical industry. SUMMARY

[0005] In order to solve the above problems in the prior art, the application provides a synthesis method and an analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve.

[0006] In a first aspect, the application provides a synthesis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve, which comprises the following steps:

[0007] S1: drying the X zeolite molecular sieve catalyst to obtain a dried X zeolite molecular sieve catalyst;

[0008] S2: heating and stirring the phenol to melt to obtain a phenol liquid;

[0009] S3: adding high-carbon alpha-olefin to the phenol liquid obtained in step S2, stirring and heating to obtain a mixture;

[0010] S4: adding the X zeolite molecular sieve catalyst dried in step S1 to the mixture obtained in step S3, stirring and heating to perform alkylation reaction to obtain long-chain alkyl phenol.

[0011] As a specific embodiment of the application, in step S1, the molar ratio of SiO2 to Al2O3 in the X zeolite molecular sieve catalyst is 1.5;

[0012] And / or, the drying temperature is 100-150℃, and the holding time is 2-15h. The drying is performed until the catalyst mass is constant.

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

[0014] As a specific embodiment of the present application, in the step S3, the high-carbon α-olefin is C12-C18, which is obtained from the LAO device of SINOPEC Maoming Petrochemical Company;

[0015] And / or, the molar ratio of the high-carbon α-olefin to phenol is 1:(2-10).

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

[0017] As a specific embodiment of the present application, in the step S4, the amount of the X zeolite molecular sieve catalyst is 1-15wt% based on the total mass of the high-carbon α-olefin and phenol; for the synthesis of dodecylphenol, the amount of the X zeolite molecular sieve catalyst is 4-6wt% based on the total mass of phenol and C12; for the synthesis of tetradecylphenol, the amount of the X zeolite molecular sieve catalyst is 4-6wt% based on the total mass of phenol and C14; for the synthesis of hexadecylphenol, the amount of the X zeolite molecular sieve catalyst is 7-9wt% based on the total mass of phenol and C16; and for the synthesis of octadecylphenol, the amount of the X zeolite molecular sieve catalyst is 7-9wt% based on the total mass of phenol and C18.

[0018] And / or, the stirring rate is 50-500rpm, the alkylation reaction temperature is 90-180℃, and the holding time is 3-8h.

[0019] In a second aspect, the present application provides an analysis method for the long-chain alkylphenol synthesized by the synthesis method of the long-chain alkylphenol catalyzed by the X zeolite molecular sieve, which comprises: uniformly mixing the long-chain alkylphenol synthesized by the synthesis method of the long-chain alkylphenol catalyzed by the X zeolite molecular sieve with dichloromethane, and then sampling into a gas chromatograph for detection and analysis.

[0020] As a specific embodiment of the present application, the dichloromethane can well disperse the long-chain alkylphenol reaction liquid.

[0021] The above raw materials in the present application can be self-made or commercially available, and the present application does not particularly limit this.

[0022] Compared with the prior art, the present application has the following beneficial effects:

[0023] 1. The method for synthesizing long-chain alkyl phenol catalyzed by X zeolite molecular sieve provided by the application is selected from X zeolite molecular sieve as catalyst, compared with traditional liquid acid catalyst, is not only friendly to environment, meets the requirement of modern green chemical industry, and is easy to separate after reaction, and is beneficial to recycling of the catalyst.

[0024] 2. The method for synthesizing long-chain alkyl phenol catalyzed by X zeolite molecular sieve provided by the application, long-chain alkyl phenol obtained by each embodiment is detected and analyzed, and the results show that conversion rates of C12-C18 high-carbon alpha-olefin are as high as 99.9% (C12), 99.9% (C14), 99.6% (C16) and 99.1% (C18) respectively, and selectivities of the corresponding long-chain alkyl phenol are as high as 99.9% (C12), 99.8% (C14), 99.1% (C16) and 97.3% (C18) respectively. DETAILED DESCRIPTION

[0025] The application will be further described in combination with specific embodiments, but does not constitute any limitation to the application.

[0026] The X zeolite molecular sieve catalyst used in each embodiment of the application has a molar ratio of SiO2 and Al2O3 of 1.5, and is purchased from Dalian Zeolite Factory.

[0027] Embodiment 1

[0028] The embodiment provides a method for synthesizing long-chain alkyl phenol catalyzed by X zeolite molecular sieve and an analysis method, and specific details are as follows:

[0029] S1: 500g X zeolite molecular sieve catalyst is placed in an oven and heated, the heating temperature is 100℃, and the holding time is 13h;

[0030] S2: phenol is placed in an oven and heated, and after melting, is added to a glass reaction kettle, stirred and heated. The amount of phenol is 35mol (3293.9g), the stirring speed is 200rpm, the heating temperature is 100℃, and the holding time is 30min;

[0031] S3: high-carbon alpha-olefin (C12) is added to the above glass reaction kettle, stirred and heated. The C12 is obtained from LAO device of Sinopec Maoming Petrochemical Company, the amount of C12 added is 5mol (841.6g), the stirring speed is 200rpm, the heating temperature is 100℃, and the holding time is 30min;

[0032] S4: The X zeolite molecular sieve catalyst after drying in step S1 was added to the above glass reactor, stirred at a stirring rate of 200 rpm and heated to 100°C to perform the alkylation reaction, the reaction time was 4 h, and long chain alkyl phenol was prepared, wherein the addition amount of the X zeolite molecular sieve catalyst was 5 wt% (206.8 g) based on the total mass of the high carbon alpha-olefin and phenol.

[0033] The long chain alkyl phenol (dodecyl phenol) synthesized in Example 1 was analyzed. Specifically, 1 mL of sample was taken out at reaction times of 2 h, 3 h and 4 h, respectively, then 2 mL of dichloromethane was added, shaken and 2 μL of sample was taken for detection in a gas chromatograph. The analysis results showed that the effect of the X zeolite molecular sieve catalyst in the synthesis of dodecyl phenol was excellent, the conversion rate of C12 olefin was as high as 99.9% at reaction times of 2 h, 3 h and 4 h, and the selectivity of the long chain alkyl phenol (dodecyl phenol) was also as high as 99.9%.

[0034] Example 2

[0035] The present embodiment provides a synthesis method and an analysis method of long chain alkyl phenol catalyzed by X zeolite molecular sieve, and the specific details are as follows:

[0036] S1: 500 g of X zeolite molecular sieve catalyst was heated in an oven, the heating temperature was 110°C, and the holding time was 13 h;

[0037] S2: 28 mol (2635.1 g) of phenol was heated in an oven, then added to a glass reactor after melting, stirred and heated, the stirring rate was 200 rpm, the heating temperature was 125°C, and the holding time was 30 min;

[0038] S3: 7 mol (1374.6 g) of high carbon alpha-olefin (C14) was added to the above glass reactor, stirred and heated. The C14 was obtained from the LAO device of Sinopec Maoming Petrochemical Company, the stirring rate was 200 rpm, the heating temperature was 125°C, and the holding time was 30 min;

[0039] S4: The X zeolite molecular sieve catalyst in an amount of 5 wt% (200.5 g) based on the total mass of the high carbon alpha-olefin and phenol was added to the above glass reactor, stirred and heated to perform the alkylation reaction, the stirring rate was 200 rpm, the alkylation reaction temperature was 125°C, and the reaction time was 5 h, and long chain alkyl phenol was prepared.

[0040] The long-chain alkyl phenol (tetradecyl phenol) synthesized in Example 2 was analyzed. 1 mL of sample was taken at 3 h, 4 h and 5 h of reaction time, respectively, followed by addition of 2 mL of dichloromethane, shaking and then taking 2 μL of sample for detection in a gas chromatograph. The analysis results show that the X zeolite molecular sieve has excellent catalytic effect on synthesis of tetradecyl phenol. The conversion rates of C14 olefin are 99.7%, 99.9% and 99.9% at 3 h, 4 h and 5 h of reaction time, respectively, and the selectivity of long-chain alkyl phenol (tetradecyl phenol) is as high as 99.8%.

[0041] Example 3

[0042] The present example provides a method for synthesizing long-chain alkyl phenol catalyzed by X zeolite molecular sieve and a method for analyzing the same, and the specific details are as follows:

[0043] S1: 600 g of X zeolite molecular sieve catalyst was heated in an oven, the heating temperature was 110°C, and the holding time was 13 h;

[0044] S2: 30 mol (2823.3 g) of phenol was heated in an oven, and after melting, it was added to a glass reaction kettle, stirred and heated, the stirring rate was 250 rpm, the heating temperature was 150°C, and the holding time was 30 min;

[0045] S3: 6 mol (1346.6 g) of high-carbon α-olefin (C16) was added to the above glass reaction kettle, stirred and heated. The C16 was obtained from the LAO device of Sinopec Maoming Petrochemical Company, the stirring rate was 200 rpm, the heating temperature was 150°C, and the holding time was 30 min;

[0046] S4: 8 wt% (333.6 g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon α-olefin and phenol was added to the above glass reaction kettle, stirred and heated for alkylation reaction, the stirring rate was 200 rpm, the alkylation reaction temperature was 150°C, and the reaction time was 6 h, to obtain long-chain alkyl phenol.

[0047] The long-chain alkyl phenol (tetradecyl phenol) synthesized in Example 2 was analyzed. 1 mL of sample was taken at 3 h, 4 h and 5 h of reaction time, respectively, followed by addition of 2 mL of dichloromethane, shaking and then taking 2 μL of sample for detection in a gas chromatograph. The analysis results show that the X zeolite molecular sieve has excellent catalytic effect on synthesis of tetradecyl phenol. The conversion rates of C14 olefin are 99.7%, 99.9% and 99.9% at 3 h, 4 h and 5 h of reaction time, respectively, and the selectivity of long-chain alkyl phenol (tetradecyl phenol) is as high as 99.8%.

[0048] Example 3

[0049] The embodiment provides a synthesis method and an analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve, and specific details are as follows.

[0050] S1: 600g of X zeolite molecular sieve catalyst is placed in an oven and heated, the heating temperature is 120 DEG C, and the holding time is 13h;

[0051] S2: the phenol is placed in an oven and heated, and after melting, it is added to a glass reaction kettle, stirred and heated. The phenol is 30mol (2823.3g), the stirring rate is 200rpm, the heating temperature is 170 DEG C, and the holding time is 30min;

[0052] S3: high-carbon alpha-olefin (C18) is added to the above glass reaction kettle, stirred and heated. The C18 is obtained from the LAO device of Sinopec Maoming Petrochemical Company, the C18 addition amount is 5mol (1262.4g), the stirring rate is 200rpm, the heating temperature is 170 DEG C, and the holding time is 30min;

[0053] S4: 8wt% (326.9g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon alpha-olefin and phenol is added to the glass reaction kettle of step S3, stirred and heated to perform alkylation reaction, the stirring rate is 200rpm, the alkylation reaction temperature is 170 DEG C, the reaction time is 6h, and long-chain alkyl phenol is prepared.

[0054] The long-chain alkyl phenol (octadecyl phenol) synthesized in Example 4 is analyzed. Specifically, 1mL of sample is taken out at the reaction time of 4h, 5h and 6h, then 2mL of dichloromethane is added, shaken and 2μL of sample is taken into a gas chromatograph for detection. The analysis result shows that the effect of synthesizing octadecyl phenol catalyzed by X zeolite molecular sieve is excellent, the conversion rate of C18 olefin is 98.7%, 99.1% and 99.1% respectively at the reaction time of 4h, 5h and 6h, and the selectivity of long-chain alkyl phenol (octadecyl phenol) is 96.9%, 97.3% and 97.3% respectively.

[0055] Example 5

[0056] The embodiment provides a synthesis method and an analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve, and specific details are as follows:

[0057] S1: 500g of X zeolite molecular sieve catalyst is placed in an oven and heated, the heating temperature is 100 DEG C, and the holding time is 13h;

[0058] S2: Phenol is heated in an oven, and after melting, it is added to the glass reaction kettle for stirring and heating. The amount of phenol is 35 mol (3293.9 g), the stirring speed is 200 rpm, the heating temperature is 100°C, and the holding time is 30 min;

[0059] S3: High-carbon alpha-olefin (C12) is added to the above glass reaction kettle for stirring and heating. The C12 is obtained from the LAO device of Sinopec Maoming Petrochemical Company, the amount of C12 added is 5 mol (841.6 g), the stirring speed is 200 rpm, the heating temperature is 100°C, and the holding time is 30 min;

[0060] S4: 4 wt% (165.4 g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon alpha-olefin and phenol is added to the above glass reaction kettle for stirring and heating to perform alkylation reaction. The stirring speed is 200 rpm, the alkylation reaction temperature is 100°C, the reaction time is 4 h, and long-chain alkyl phenol is prepared.

[0061] The long-chain alkyl phenol (dodecyl phenol) synthesized in Example 5 is analyzed. Specifically, 1 mL of sample is taken at reaction times of 2 h, 3 h and 4 h, respectively, then 2 mL of dichloromethane is added, shaken uniformly, and 2 μL of sample is taken for detection in a gas chromatograph. The analysis results show that at reaction times of 2 h, 3 h and 4 h, the conversion rates of C12 olefin are 97.8%, 98.4% and 98.5%, respectively, and the selectivities of the corresponding long-chain alkyl phenol (dodecyl phenol) are 98.9%, 99.1% and 99.1%, respectively.

[0062] Example 6

[0063] This example provides a synthesis method and analysis method of X zeolite molecular sieve catalyzed long-chain alkyl phenol, and the specific details are as follows:

[0064] S1: 500 g of X zeolite molecular sieve catalyst is heated in an oven, the heating temperature is 100°C, and the holding time is 13 h;

[0065] S2: Phenol is heated in an oven, and after melting, it is added to the glass reaction kettle for stirring and heating. The amount of phenol is 35 mol (3293.9 g), the stirring speed is 200 rpm, the heating temperature is 100°C, and the holding time is 30 min;

[0066] S3: High-carbon alpha-olefin (C12) is added to the above glass reaction kettle for stirring and heating. The C12 is obtained from the LAO device of Sinopec Maoming Petrochemical Company, the amount of C12 added is 5 mol (841.6 g), the stirring speed is 200 rpm, the heating temperature is 100°C, and the holding time is 30 min;

[0067] S4: 6 wt% (248.1 g) of the X zeolite molecular sieve catalyst based on the total mass of the high-carbon alpha-olefin and phenol was added to the above glass reaction kettle, and stirring and heating were performed to carry out the alkylation reaction, the stirring speed was 200 rpm, the alkylation reaction temperature was 100°C, and the reaction time was 4 h, to obtain long-chain alkylphenol.

[0068] The long-chain alkylphenol (dodecylphenol) synthesized in Example 6 was analyzed. Specifically, 1 mL of sample was taken out at 2 h, 3 h and 4 h of reaction time, 2 mL of dichloromethane was then added, and 2 μL of the sample was taken for detection in a gas chromatograph after shaking. The analysis results showed that the conversion rates of C12 olefin were 99.8%, 99.9% and 99.9% at 2 h, 3 h and 4 h of reaction time, and the selectivities of the long-chain alkylphenol (dodecylphenol) were 99.4%, 99.6% and 99.6%, respectively.

[0069] Example 7

[0070] This example provides a method for synthesizing long-chain alkylphenol and a method for analyzing the long-chain alkylphenol catalyzed by X zeolite molecular sieve, and the specific details are as follows:

[0071] S1: 500 g of X zeolite molecular sieve catalyst was placed in an oven and heated, the heating temperature was 100°C, and the holding time was 13 h;

[0072] S2: The phenol was heated in an oven, melted and then added to the glass reaction kettle, and stirring and heating were performed. The amount of phenol was 35 mol (3293.9 g), the stirring speed was 200 rpm, the heating temperature was 90°C, and the holding time was 30 min;

[0073] S3: The high-carbon alpha-olefin (C12) was added to the above glass reaction kettle, and stirring and heating were performed. The C12 was obtained from the LAO device of Sinopec Maoming Petrochemical Company, the amount of C12 added was 5 mol (841.6 g), the stirring speed was 200 rpm, the heating temperature was 90°C, and the holding time was 30 min;

[0074] S4: 5 wt% (206.8 g) of the X zeolite molecular sieve catalyst based on the total mass of the high-carbon alpha-olefin and phenol was added to the above glass reaction kettle, and stirring and heating were performed to carry out the alkylation reaction, the stirring speed was 200 rpm, the alkylation reaction temperature was 90°C, and the reaction time was 4 h, to obtain long-chain alkylphenol.

[0075] The long-chain alkyl phenol (dodecyl phenol) synthesized in Example 8 was analyzed. Specifically, 1 mL of sample was taken at 2 h, 3 h and 4 h of reaction time, followed by addition of 2 mL of dichloromethane, shaking and then taking 2 μL of sample for detection in a gas chromatograph. The analysis results show that at 2 h, 3 h and 4 h of reaction time, the conversion rates of C12 olefin are 95.4%, 95.8% and 95.8% respectively, and the selectivities of the long-chain alkyl phenol (dodecyl phenol) are 96.7%, 96.9% and 96.9% respectively.

[0076] Example 8

[0077] The present example provides a method for synthesizing long-chain alkyl phenol catalyzed by X zeolite molecular sieve and a method for analyzing the same, and the specific details are as follows:

[0078] S1: 500 g of X zeolite molecular sieve catalyst was heated in an oven, the heating temperature was 100°C, and the holding time was 13 h;

[0079] S2: The phenol was heated in an oven, and after melting, it was added to a glass reaction kettle, stirred and heated. The amount of phenol was 35 mol (3293.9 g), the stirring speed was 200 rpm, the heating temperature was 110°C, and the holding time was 30 min;

[0080] S3: High-carbon α-olefin (C12) was added to the above glass reaction kettle, stirred and heated. The C12 was obtained from the LAO device of Sinopec Maoming Petrochemical Company, the amount of C12 added was 5 mol (841.6 g), the stirring speed was 200 rpm, the heating temperature was 110°C, and the holding time was 30 min;

[0081] S4: 5 wt% (206.8 g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon α-olefin and phenol was added to the above glass reaction kettle, stirred and heated for alkylation reaction, the stirring speed was 200 rpm, the alkylation reaction temperature was 110°C, the reaction time was 4 h, and long-chain alkyl phenol was prepared.

[0082] The long-chain alkyl phenol (dodecyl phenol) synthesized in Example 8 was analyzed. Specifically, 1 mL of sample was taken at 2 h, 3 h and 4 h of reaction time, followed by addition of 2 mL of dichloromethane, shaking and then taking 2 μL of sample for detection in a gas chromatograph. The analysis results show that at 2 h, 3 h and 4 h of reaction time, the conversion rates of C12 olefin are 95.4%, 95.8% and 95.8% respectively, and the selectivities of the long-chain alkyl phenol (dodecyl phenol) are 96.7%, 96.9% and 96.9% respectively.

[0083] Example 8

[0084] The embodiment provides a synthesis method and an analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve, and specific details are as follows.

[0085] S1: 500g of X zeolite molecular sieve catalyst is placed in an oven and heated, the heating temperature is 100 DEG C, and the holding time is 13h;

[0086] S2: the phenol is heated in an oven, and after melting, is added to a glass reaction kettle, and is stirred and heated. The phenol is 30mol (2823.3g) in quantity, the stirring speed is 200rpm, the heating temperature is 100 DEG C, and the holding time is 30min;

[0087] S3: high-carbon alpha-olefin (C12) is added to the above glass reaction kettle, and is stirred and heated. The C12 is obtained from a LAO device of Sinopec Maoming Petrochemical Company, the C12 is 5mol (841.6g) in quantity, the stirring speed is 200rpm, the heating temperature is 100 DEG C, and the holding time is 30min;

[0088] S4: 5wt% (183.2g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon alpha-olefin and phenol is added to the above glass reaction kettle, and is stirred and heated to perform alkylation reaction, the stirring speed is 200rpm, the alkylation reaction temperature is 100 DEG C, the reaction time is 4h, and long-chain alkyl phenol is prepared.

[0089] The long-chain alkyl phenol (dodecyl phenol) synthesized in the embodiment 9 is analyzed. Specifically, 1mL of sample is taken out when the reaction time is 2h, 3h and 4h respectively, then 2mL of dichloromethane is added, and after shaking, 2ul of sample is taken into a gas chromatograph for detection. The analysis result shows that when the reaction time is 2h, 3h and 4h, the conversion rate of C12 olefin is 96.8%, 97.2% and 97.2% respectively, and the selectivity of long-chain alkyl phenol (dodecyl phenol) is 96.3%, 96.6% and 96.6% respectively.

[0090] Embodiment 10

[0091] The embodiment provides a synthesis method and an analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve, and specific details are as follows.

[0092] S1: 500g of X zeolite molecular sieve catalyst is placed in an oven and heated, the heating temperature is 100 DEG C, and the holding time is 13h;

[0093] S2: the phenol is heated in an oven, and after melting, is added to a glass reaction kettle, and is stirred and heated. The phenol is 30mol (2823.3g) in quantity, the stirring speed is 200rpm, the heating temperature is 100 DEG C, and the holding time is 30min;

[0094] S3: 7 mol (1374.6 g) of high carbon alpha-olefins (C14) were added to the above glass reactor, stirred and heated. Among them, C14 was obtained from the LAO device of Sinopec Maoming Petrochemical Company, the stirring speed was 200 rpm, the heating temperature was 125°C, and the holding time was 30 min;

[0095] S4: 4 wt% (160.4 g) of X zeolite molecular sieve catalyst based on the total mass of high carbon alpha-olefins and phenol was added to the above glass reactor, stirred and heated for alkylation reaction, the stirring speed was 200 rpm, the alkylation reaction temperature was 125°C, the reaction time was 5 h, and long chain alkyl phenol was prepared.

[0096] The long chain alkyl phenol (dodecyl phenol) synthesized in Example 10 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 2 h, 3 h and 4 h, then 2 mL of dichloromethane was added, shaken and 2 μL was taken for gas chromatography detection. The analysis results show that at reaction times of 2 h, 3 h and 4 h, the conversion rates of C12 olefins are 99.5%, 99.7% and 99.8%, respectively, and the selectivities of the long chain alkyl phenol (dodecyl phenol) are 99.4%, 99.7% and 99.7%, respectively.

[0097] Example 11

[0098] The present embodiment provides a synthesis method and analysis method of long chain alkyl phenol catalyzed by X zeolite molecular sieve, and the specific details are as follows:

[0099] S1: 500 g of X zeolite molecular sieve catalyst was heated in an oven, the heating temperature was 110°C, and the holding time was 13 h;

[0100] S2: 28 mol (2635.1 g) of phenol was heated in an oven, then added to a glass reactor, stirred and heated, the stirring speed was 200 rpm, the heating temperature was 125°C, and the holding time was 30 min;

[0101] S3: 7 mol (1374.6 g) of high carbon alpha-olefins (C14) were added to the above glass reactor, stirred and heated. Among them, C14 was obtained from the LAO device of Sinopec Maoming Petrochemical Company, the stirring speed was 200 rpm, the heating temperature was 125°C, and the holding time was 30 min;

[0102] S4: 4 wt% (160.4 g) of X zeolite molecular sieve catalyst based on the total mass of high carbon alpha-olefins and phenol was added to the above glass reactor, stirred and heated for alkylation reaction, the stirring speed was 200 rpm, the alkylation reaction temperature was 125°C, the reaction time was 5 h, and long chain alkyl phenol was prepared.

[0103] The long-chain alkyl phenol (tetradecyl phenol) synthesized in Example 11 was analyzed. When the reaction time was 3 h, 4 h and 5 h, respectively, 1 mL of sample was taken out, then 2 mL of dichloromethane was added, and 2 μL of sample was taken for detection in the gas chromatograph after shaking. The analysis results showed that when the reaction time was 3 h, 4 h and 5 h, respectively, the conversion rate of C14 olefin was 98.7%, 99.0% and 99.0%, respectively, and the selectivity of the long-chain alkyl phenol (tetradecyl phenol) was 98.6%, 99.0% and 99.0%, respectively.

[0104] Example 12

[0105] The present embodiment provides a method for synthesizing long-chain alkyl phenol catalyzed by X zeolite molecular sieve and a method for analyzing the same, and the specific details are as follows:

[0106] S1: 500 g of X zeolite molecular sieve catalyst was heated in an oven, the heating temperature was 110°C, and the holding time was 13 h;

[0107] S2: 28 mol (2635.1 g) of phenol was heated in an oven, and after melting, it was added to a glass reaction kettle, stirred and heated, the stirring rate was 200 rpm, the heating temperature was 125°C, and the holding time was 30 min;

[0108] S3: 7 mol (1374.6 g) of high-carbon α-olefin (C14) was added to the above glass reaction kettle, stirred and heated. The C14 was obtained from the LAO device of Sinopec Maoming Petrochemical Company, the stirring rate was 200 rpm, the heating temperature was 125°C, and the holding time was 30 min;

[0109] S4: 6 wt% (240.6 g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon α-olefin and phenol was added to the above glass reaction kettle, stirred and heated for alkylation reaction, the stirring rate was 200 rpm, the alkylation reaction temperature was 125°C, the reaction time was 5 h, and the long-chain alkyl phenol was prepared.

[0110] The long-chain alkyl phenol (tetradecyl phenol) synthesized in Example 11 was analyzed. When the reaction time was 3 h, 4 h and 5 h, respectively, 1 mL of sample was taken out, then 2 mL of dichloromethane was added, and 2 μL of sample was taken for detection in the gas chromatograph after shaking. The analysis results showed that when the reaction time was 3 h, 4 h and 5 h, respectively, the conversion rate of C14 olefin was 98.7%, 99.0% and 99.0%, respectively, and the selectivity of the long-chain alkyl phenol (tetradecyl phenol) was 98.6%, 99.0% and 99.0%, respectively.

[0111] Example 13

[0112] The embodiment provides a synthesis method and an analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve, and specific details are as follows.

[0113] S1: 500g of X zeolite molecular sieve catalyst is placed in an oven and heated, the heating temperature is 110 DEG C, and the holding time is 13h;

[0114] S2: 28mol (2635.1g) of phenol is placed in an oven and heated, and after melting, is added to a glass reaction kettle, stirred and heated, the stirring rate is 200rpm, the heating temperature is 115 DEG C, and the holding time is 30min;

[0115] S3: 7mol (1374.6g) of high-carbon alpha-olefin (C14) is added to the above glass reaction kettle, stirred and heated, wherein the C14 is obtained from a LAO device of Sinopec Maoming Petrochemical Company, the stirring rate is 200rpm, the heating temperature is 115 DEG C, and the holding time is 30min;

[0116] S4: 5wt% (200.5g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon alpha-olefin and phenol is added to the above glass reaction kettle, stirred and heated to perform alkylation reaction, the stirring rate is 200rpm, the alkylation reaction temperature is 115 DEG C, the reaction time is 5h, and long-chain alkyl phenol is prepared.

[0117] The long-chain alkyl phenol (tetradecyl phenol) synthesized in the embodiment 13 is analyzed, 1mL of sample is taken out when the reaction time is 3h, 4h and 5h respectively, then 2mL of dichloromethane is added, shaken uniformly, 2ul of sample is taken into a gas chromatograph for detection. The analysis result shows that when the reaction time is 3h, 4h and 5h, the conversion rate of C14 olefin is 95.8%, 96.2% and 96.2% respectively, and the selectivity of long-chain alkyl phenol (tetradecyl phenol) is 97.8%, 98.1% and 98.1% respectively.

[0118] Embodiment 14

[0119] The embodiment provides a synthesis method and an analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve, and specific details are as follows:

[0120] S1: 500g of X zeolite molecular sieve catalyst is placed in an oven and heated, the heating temperature is 110 DEG C, and the holding time is 13h;

[0121] S2: 28mol (2635.1g) of phenol is placed in an oven and heated, and after melting, is added to a glass reaction kettle, stirred and heated, the stirring rate is 200rpm, the heating temperature is 115 DEG C, and the holding time is 30min;

[0122] S3: 7 mol (1374.6 g) of high carbon alpha-olefin (C14) was added to the above glass reactor, stirred and heated. Among them, C14 was from Sinopec Maoming Petrochemical Company LAO device, the stirring rate was 200 rpm, the heating temperature was 135 °C, and the holding time was 30 min;

[0123] S4: 5 wt% (200.5 g) of X zeolite molecular sieve catalyst based on the total mass of high carbon alpha-olefin and phenol was added to the above glass reactor, stirred and heated for alkylation reaction, the stirring rate was 200 rpm, the alkylation reaction temperature was 135 °C, the reaction time was 5 h, and long chain alkyl phenol was prepared.

[0124] The long chain alkyl phenol (tetradecyl phenol) synthesized in Example 14 was analyzed. When the reaction time was 3 h, 4 h and 5 h, 1 mL of sample was taken out, then 2 mL of dichloromethane was added, shaken and 2 μL was taken for gas chromatography detection. The analysis results showed that when the reaction time was 3 h, 4 h and 5 h, the conversion rate of C14 olefin was 99.6%, 99.8% and 99.8% respectively, and the selectivity of long chain alkyl phenol (tetradecyl phenol) was 99.7%.

[0125] Example 15

[0126] This example provides a synthesis method and analysis method of X zeolite molecular sieve catalyzed long chain alkyl phenol, and the specific details are as follows:

[0127] S1: 500 g of X zeolite molecular sieve catalyst was heated in an oven, the heating temperature was 110 °C, and the holding time was 13 h;

[0128] S2: 21 mol (1976.3 g) of phenol was heated in an oven, melted and added to the glass reactor, stirred and heated, the stirring rate was 200 rpm, the heating temperature was 125 °C, and the holding time was 30 min;

[0129] S3: 7 mol (1374.6 g) of high carbon alpha-olefin (C14) was added to the above glass reactor, stirred and heated. Among them, C14 was from Sinopec Maoming Petrochemical Company LAO device, the stirring rate was 200 rpm, the heating temperature was 125 °C, and the holding time was 30 min;

[0130] S4: 5 wt% (167.5 g) of X zeolite molecular sieve catalyst based on the total mass of high carbon alpha-olefin and phenol was added to the above glass reactor, stirred and heated for alkylation reaction, the stirring rate was 200 rpm, the alkylation reaction temperature was 125 °C, the reaction time was 5 h, and long chain alkyl phenol was prepared.

[0131] The long-chain alkyl phenol (tetradecyl phenol) synthesized in Example 15 was analyzed. When the reaction time was 3 h, 4 h and 5 h, respectively, 1 mL of sample was taken out, then 2 mL of dichloromethane was added, and 2 μL of sample was taken for detection in the gas chromatograph after shaking. The analysis results showed that when the reaction time was 3 h, 4 h and 5 h, respectively, the conversion rate of C14 olefin was 95.4%, 95.8% and 95.8%, respectively, and the selectivity of the corresponding long-chain alkyl phenol (tetradecyl phenol) was 96.8%, 97.0% and 97.0%, respectively.

[0132] Example 16

[0133] This example provides a method for synthesizing long-chain alkyl phenol catalyzed by X zeolite molecular sieve and a method for analyzing the same, and the specific details are as follows:

[0134] S1: 500 g of X zeolite molecular sieve catalyst was heated in an oven, the heating temperature was 110°C, and the holding time was 13 h;

[0135] S2: 35 mol (3293.9 g) of phenol was heated in an oven, and after melting, it was added to a glass reaction kettle, stirred and heated, the stirring rate was 200 rpm, the heating temperature was 125°C, and the holding time was 30 min;

[0136] S3: 7 mol (1374.6 g) of high-carbon α-olefin (C14) was added to the above glass reaction kettle, stirred and heated. The C14 was obtained from the LAO device of Sinopec Maoming Petrochemical Company, the stirring rate was 200 rpm, the heating temperature was 125°C, and the holding time was 30 min;

[0137] S4: 5 wt% (233.4 g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon α-olefin and phenol was added to the above glass reaction kettle, stirred and heated for alkylation reaction, the stirring rate was 200 rpm, the alkylation reaction temperature was 125°C, the reaction time was 5 h, and long-chain alkyl phenol was prepared.

[0138] The long-chain alkyl phenol (tetradecyl phenol) synthesized in Example 16 was analyzed. When the reaction time was 3 h, 4 h and 5 h, respectively, 1 mL of sample was taken out, then 2 mL of dichloromethane was added, and 2 μL of sample was taken for detection in the gas chromatograph after shaking. The analysis results showed that when the reaction time was 3 h, 4 h and 5 h, respectively, the conversion rate of C14 olefin was 99.4%, 99.7% and 99.7%, and the selectivity of the corresponding long-chain alkyl phenol (tetradecyl phenol) was 99.7%.

[0139] Example 17

[0140] This example provides a method for synthesizing long-chain alkyl phenol catalyzed by X zeolite molecular sieve and a method for analyzing the same, and the specific details are as follows:

[0141] S1: 600g X zeolite molecular sieve catalyst was placed in an oven for heating, the heating temperature was 110°C, and the holding time was 13h;

[0142] S2: 30mol (2823.3g) of phenol was placed in an oven for heating, and after melting, it was added to a glass reaction kettle, stirred and heated, the stirring rate was 250rpm, the heating temperature was 150°C, and the holding time was 30min;

[0143] S3: 6mol (1346.6g) of high-carbon α-olefin (C16) was added to the above glass reaction kettle, stirred and heated. Among them, C16 was obtained from the LAO device of Sinopec Maoming Petrochemical Company, the stirring rate was 200rpm, the heating temperature was 150°C, and the holding time was 30min;

[0144] S4: 7wt% (291.9g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon α-olefin and phenol was added to the above glass reaction kettle, stirred and heated for alkylation reaction, the stirring speed was 200rpm, the alkylation reaction temperature was 150°C, the reaction time was 6h, and long-chain alkyl phenol was prepared.

[0145] The long-chain alkyl phenol (hexadecyl phenol) synthesized in Example 17 was analyzed. Specifically, 1mL of sample was taken at reaction times of 4h, 5h and 6h, respectively, then 2mL of dichloromethane was added, shaken and 2μL of sample was taken for detection in a gas chromatograph. The analysis results show that at reaction times of 4h, 5h and 6h, the conversion rates of C16 olefin are 97.7%, 97.9% and 97.9% respectively, and the selectivities of the corresponding long-chain alkyl phenol (hexadecyl phenol) are 97.8%, 98.0% and 98.0% respectively.

[0146] Example 18

[0147] The present embodiment provides a synthesis method and analysis method for long-chain alkyl phenol catalyzed by X zeolite molecular sieve, and the specific details are as follows:

[0148] S1: 600g X zeolite molecular sieve catalyst was placed in an oven for heating, the heating temperature was 110°C, and the holding time was 13h;

[0149] S2: 30mol (2823.3g) of phenol was placed in an oven for heating, and after melting, it was added to a glass reaction kettle, stirred and heated, the stirring rate was 250rpm, the heating temperature was 150°C, and the holding time was 30min;

[0150] S3: 6 mol (1346.6 g) of high carbon alpha-olefin (C16) was added to the above glass reactor, stirred and heated. Among them, C16 is from SINOPEC Maoming Petrochemical Company LAO device, the stirring speed is 200 rpm, the heating temperature is 150°C, and the holding time is 30 min;

[0151] S4: 9 wt% (375.3 g) of X zeolite molecular sieve catalyst based on the total mass of high carbon alpha-olefin and phenol was added to the above glass reactor, stirred and heated for alkylation reaction, the stirring speed was 200 rpm, the alkylation reaction temperature was 150°C, the reaction time was 6 h, and long chain alkyl phenol was prepared.

[0152] The long chain alkyl phenol (hexadecyl phenol) synthesized in Example 18 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 4 h, 5 h and 6 h, then 2 mL of dichloromethane was added, shaken and 2 μL was taken for gas chromatography detection. The analysis results show that at reaction times of 4 h, 5 h and 6 h, the conversion rates of C16 olefin are 99.0%, 99.6% and 99.6%, respectively, and the selectivities of the long chain alkyl phenol (hexadecyl phenol) are 98.6%, 98.3% and 98.3%, respectively.

[0153] Example 19

[0154] The present embodiment provides a synthesis method and analysis method of X zeolite molecular sieve catalyzed long chain alkyl phenol, and the specific details are as follows:

[0155] S1: 600 g of X zeolite molecular sieve catalyst was heated in an oven, the heating temperature was 110°C, and the holding time was 13 h;

[0156] S2: 30 mol (2823.3 g) of phenol was heated in an oven, then added to the glass reactor after melting, stirred and heated, the stirring speed was 250 rpm, the heating temperature was 140°C, and the holding time was 30 min;

[0157] S3: 6 mol (1346.6 g) of high carbon alpha-olefin (C16) was added to the above glass reactor, stirred and heated. Among them, C16 is from SINOPEC Maoming Petrochemical Company LAO device, the stirring speed is 200 rpm, the heating temperature is 140°C, and the holding time is 30 min;

[0158] S4: 8 wt% (333.6 g) of X zeolite molecular sieve catalyst based on the total mass of high carbon alpha-olefin and phenol was added to the above glass reactor, stirred and heated for alkylation reaction, the stirring speed was 200 rpm, the alkylation reaction temperature was 140°C, the reaction time was 6 h, and long chain alkyl phenol was prepared.

[0159] The long-chain alkyl phenol (hexadecyl phenol) synthesized in Example 19 was analyzed. Specifically, 1 mL of sample was taken at 4 h, 5 h and 6 h of reaction time, followed by addition of 2 mL of dichloromethane, shaking and then taking 2 μL of sample for detection in a gas chromatograph. The analysis results show that at 4 h, 5 h and 6 h of reaction time, the conversion rates of C16 olefin are 95.4%, 95.7% and 95.7% respectively, and the selectivities of the long-chain alkyl phenol (hexadecyl phenol) are 96.4%, 96.6% and 96.6% respectively.

[0160] Example 20

[0161] The present example provides a method for synthesizing long-chain alkyl phenol catalyzed by X zeolite molecular sieve and a method for analyzing the same, and the specific details are as follows:

[0162] S1: 600 g of X zeolite molecular sieve catalyst was heated in an oven, the heating temperature was 110°C, and the holding time was 13 h;

[0163] S2: 30 mol (2823.3 g) of phenol was heated in an oven, and after melting, it was added to a glass reaction kettle, stirred and heated, the stirring rate was 250 rpm, the heating temperature was 160°C, and the holding time was 30 min;

[0164] S3: 6 mol (1346.6 g) of high-carbon α-olefin (C16) was added to the above glass reaction kettle, stirred and heated. The C16 was obtained from the LAO device of Sinopec Maoming Petrochemical Company, the stirring rate was 200 rpm, the heating temperature was 160°C, and the holding time was 30 min;

[0165] S4: 8 wt% (333.6 g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon α-olefin and phenol was added to the above glass reaction kettle, stirred and heated for alkylation reaction, the stirring rate was 200 rpm, the alkylation reaction temperature was 160°C, the reaction time was 6 h, and long-chain alkyl phenol was prepared.

[0166] The long-chain alkyl phenol (hexadecyl phenol) synthesized in Example 20 was analyzed. Specifically, 1 mL of sample was taken at 4 h, 5 h and 6 h of reaction time, followed by addition of 2 mL of dichloromethane, shaking and then taking 2 μL of sample for detection in a gas chromatograph. The analysis results show that at 4 h, 5 h and 6 h of reaction time, the conversion rates of C16 olefin are 99.3%, 99.5% and 99.6% respectively, and the selectivities of the long-chain alkyl phenol (hexadecyl phenol) are 98.5%, 98.9% and 98.9% respectively.

[0167] Example 21

[0168] The embodiment provides a synthesis method and an analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve, and specific details are as follows.

[0169] S1: 600g of X zeolite molecular sieve catalyst is placed in an oven and heated, the heating temperature is 110 DEG C, and the holding time is 13h;

[0170] S2: 24mol (2258.6g) of phenol is placed in an oven and heated, and after melting, is added to a glass reaction kettle, stirred and heated, the stirring speed is 250rpm, the heating temperature is 150 DEG C, and the holding time is 30min;

[0171] S3: 6mol (1346.6g) of high-carbon alpha-olefin (C16) is added to the above glass reaction kettle, stirred and heated, wherein the C16 is obtained from a LAO device of SINOPEC Maoming Petrochemical Company, the stirring speed is 200rpm, the heating temperature is 150 DEG C, and the holding time is 30min;

[0172] S4: 8wt% (288.4g) of X zeolite molecular sieve catalyst based on the total mass of high-carbon alpha-olefin and phenol is added to the above glass reaction kettle, stirred and heated to perform alkylation reaction, the stirring speed is 200rpm, the alkylation reaction temperature is 150 DEG C, the reaction time is 6h, and long-chain alkyl phenol is prepared.

[0173] The long-chain alkyl phenol (hexadecyl phenol) synthesized in the embodiment 21 is analyzed, specifically, 1mL of sample is taken out when the reaction time is 4h, 5h and 6h respectively, then 2mL of dichloromethane is added, shaken uniformly, and 2ul of sample is taken into a gas chromatograph for detection. The analysis result shows that when the reaction time is 4h, 5h and 6h, the conversion rate of C16 olefin is 95.2%, 95.5% and 95.5% respectively, and the selectivity of long-chain alkyl phenol (hexadecyl phenol) is 96.1%, 96.4% and 96.4% respectively.

[0174] Embodiment 22

[0175] The embodiment provides a synthesis method and an analysis method of long-chain alkyl phenol catalyzed by X zeolite molecular sieve, and specific details are as follows:

[0176] S1: 600g of X zeolite molecular sieve catalyst is placed in an oven and heated, the heating temperature is 110 DEG C, and the holding time is 13h;

[0177] S2: 36mol (3388.0g) of phenol is placed in an oven and heated, and after melting, is added to a glass reaction kettle, stirred and heated, the stirring speed is 250rpm, the heating temperature is 150 DEG C, and the holding time is 30min;

[0178] S3: 6 mol (1346.6 g) of high carbon α-olefin (C16) was added to the above glass reactor, stirred and heated. Among them, C16 was obtained from Sinopec Maoming Petrochemical Company LAO device, the stirring speed was 200 rpm, the heating temperature was 150°C, and the holding time was 30 min;

[0179] S4: 8 wt% (378.8 g) of X zeolite molecular sieve catalyst based on the total mass of high carbon α-olefin and phenol was added to the above glass reactor, stirred and heated to carry out alkylation reaction, the stirring speed was 200 rpm, the alkylation reaction temperature was 150°C, the reaction time was 6 h, and long chain alkyl phenol was prepared.

[0180] The long chain alkyl phenol (hexadecyl phenol) synthesized in Example 22 was analyzed. Specifically, 1 mL of sample was taken at reaction times of 4 h, 5 h and 6 h, then 2 mL of dichloromethane was added, shaken and 2 μL was taken for gas chromatography detection. The analysis results show that at reaction times of 4 h, 5 h and 6 h, the conversion rates of C16 olefin are 98.9%, 99.4% and 99.5%, respectively, and the selectivities of the corresponding long chain alkyl phenol (hexadecyl phenol) are 98.5%, 98.9% and 98.9%, respectively.

[0181] In summary, the synthesis method of long chain alkyl phenol catalyzed by X zeolite molecular sieve of the present application selects X zeolite molecular sieve as the catalyst, and the prepared long chain alkyl phenol is detected and analyzed. The results show that the conversion rates of C12-C18 high carbon α-olefin are as high as 99.9% (C12), 99.9% (C14), 99.6% (C16) and 99.1% (C18), respectively, and the selectivities of the corresponding long chain alkyl phenol are as high as 99.9% (C12), 99.8% (C14), 99.1% (C16) and 97.3% (C18), respectively.

[0182] Any numerical values recited in the above application, including any numerical values of a possible range specified in any of the claims, are intended to be "approximations," and as the specification commands, are presented only to provide a statistical precision. In this manner, it is understood that the numerical values are merely intended to serve as an approximation. It is also understood, that the use of numerical values in the specification is merely to serve as an approximation, and that the numerical values are not intended to be limiting.

[0183] It should be noted that the foregoing examples have been provided merely for the purposes of illustration and are not intended to limit the application in any way. Descriptions and examples of materials and processes of the application are intended to be illustrative not limiting. Any modifications of the application and other applications of the application will occur to those skilled in the art to which the application pertains and many options for modification of the application will suggest themselves. The application lies in the broadest aspects of the art, and there are many alternatives for carrying out the application. Accordingly, the scope of the application should be determined not with reference to the above description but with reference to the claims that follow.

Claims

1. A process for the synthesis of long chain alkyl phenol catalyzed by X zeolite molecular sieve, characterized in that, The method comprises the following steps: S1: drying the X zeolite molecular sieve catalyst to obtain a dried X zeolite molecular sieve catalyst; S2: heating and stirring the phenol to melt to obtain a phenol liquid; S3: adding high-carbon α-olefin to the phenol liquid obtained in step S2, and stirring and heating to obtain a mixture; the high-carbon α-olefin is C12-C18; S4: adding the X zeolite molecular sieve catalyst dried in step S1 to the mixture obtained in step S3, and stirring and heating to perform alkylation to obtain long-chain alkylphenol; the alkylation temperature is 90-180°C.

2. The method of synthesis of claim 1, wherein, In step S1, the molar ratio of SiO2 to Al2O3 in the X zeolite molecular sieve catalyst is 1.

5. And / or, the drying temperature is 100-150°C, and the holding time is 2-15 h.

3. The method of synthesis of claim 1, wherein, In step S2, the stirring rate is 50-500 rpm, the heating temperature is 90-180°C, and the holding time is 5-50 min.

4. The method of synthesis of claim 1, wherein, In step S3, the high-carbon α-olefin is obtained from the LAO device of Sinopec Maoming Petrochemical Company; And / or, the molar ratio of the high-carbon α-olefin to the phenol is 1:(2-10); And / or, the stirring rate is 50-500 rpm, the heating temperature is 90-180°C, and the holding time is 5-50 min.

5. The method of synthesis according to any one of claims 1-4, wherein, In step S4, the amount of the X zeolite molecular sieve catalyst is 1-15 wt% based on the total mass of the high-carbon α-olefin and the phenol; And / or, the stirring rate is 50-500 rpm, and the reaction time is 3-8 h.