A process for the catalytic hydration of alpha-olefins to produce secondary alcohols

Abstract

The application relates to the technical field of fine chemicals, and discloses a method for preparing secondary alcohol by catalyzing alpha-olefin hydration. The method comprises the following steps: under the catalysis of a catalyst, performing an aldehyde amine condensation reaction on 1,3,5-tri-(p-formylphenyl) benzene and o-sulfonic acid p-phenylenediamine in a first organic solvent in an air-isolated condition, then sequentially performing washing and drying on the obtained reaction product to obtain a COF-HSO3 catalyst, and then under the catalysis of the COF-HSO3 catalyst, performing a hydration reaction on alpha-olefin in a second organic solvent and water. The method for preparing secondary alcohol by catalyzing alpha-olefin hydration has high alpha-olefin conversion rate and secondary alcohol yield.

Description

Technical Field

[0001] This invention relates to the field of fine chemical technology, and specifically to a method for preparing secondary alcohols by catalytic hydration of α-olefins. Background Technology

[0002] Secondary alcohols are an important class of organic alcohols characterized by hydroxyl groups (-OH) attached to secondary carbon atoms. This structural feature gives them a significant role in pharmaceutical molecules, natural polymers, and synthetic chemistry. Secondary alcohol polyoxyethylene ethers, synthesized from high-carbon-chain secondary alcohols, are environmentally friendly and excellent surfactants. They possess not only excellent penetration, emulsification, wetting, and detergency properties but also good biodegradability. In practical applications, they can be compounded with all types of surfactants (including anionic, cationic, and nonionic) to produce a powerful synergistic effect. This effect can significantly reduce the amount of other additives used, resulting in better economic benefits. Simultaneously, they can enhance the effectiveness of paint thickeners and improve the rinsing performance of solvent-based systems.

[0003] The direct catalytic hydration of α-olefins is a major method for preparing secondary alcohols. Firstly, one of the key factors in the preparation of secondary alcohols is the precise control of the temperature of the catalytic hydration reaction of α-olefins. Studies have shown that maintaining the temperature within the optimized range of 150 to 200 °C can effectively balance the reaction rate and product selectivity. Secondly, the choice of hydration catalyst is crucial in the catalytic hydration of secondary alcohols. Using homogeneous catalysts with specific active components, whose active centers can effectively adsorb α-olefins and direct the reaction towards the target product, can increase the conversion rate to approximately 70%. For example, sulfuric acid catalysis is widely used in catalytic olefin hydration processes. Its acidity can efficiently protonate olefin double bonds, but its strong corrosiveness necessitates the use of Hastelloy reactor materials (increasing costs by 40%), and the waste acid treatment requires multi-stage neutralization (resin accounting for 15-20%). Furthermore, reaction pressure and time are also key process parameters for the catalytic hydration of α-olefins to produce secondary alcohols. Studies have shown that reacting under pressure conditions of 2-5 MPa can significantly improve efficiency and yield; while controlling the reaction time to 3-5 h can ensure sufficient reaction and achieve high product purity, and this parameter range has been widely accepted. The choice of solvent is crucial to the effectiveness of the catalytic hydration of α-olefins to secondary alcohols. Polar solvents (such as certain ethers) can better dissolve the components of the reaction system, enhance molecular interactions, and thus effectively improve the reaction activity.

[0004] The indirect hydration pathway for olefins is an industrial catalytic method for converting olefins into alcohols through intermediate reaction steps. Compared to direct hydration (direct addition of water to olefins), it achieves higher selectivity and conversion rates through multiple reaction steps. For example, olefins react with concentrated sulfuric acid to form a sulfate ester intermediate (such as cyclohexene sulfate), which is then hydrolyzed to produce cyclohexanol. The advantages of this process are that the catalytic hydration reaction conditions are mild, the selectivity is high, and it is suitable for the hydration of high-carbon olefins; however, the hydration reaction generates a large amount of acidic waste liquid, posing a significant environmental burden, and the hydration process can easily cause equipment corrosion. Summary of the Invention

[0005] The purpose of this invention is to overcome the problems of high process cost, serious environmental pollution, and low selectivity of target products in existing methods for preparing secondary alcohols from α-olefins, and to provide a method for preparing secondary alcohols by catalytic hydration of α-olefins. The method for preparing secondary alcohols by catalytic hydration of α-olefins described in this invention has high α-olefin conversion and secondary alcohol yield.

[0006] To achieve the above objectives, the present invention provides a method for the catalytic hydration of α-olefins to prepare secondary alcohols. The method comprises: 1,3,5-tris(p-formylphenyl)benzene and p-phenylenediamine o-sulfonate undergoing an aldehyde-amine condensation reaction in a first organic solvent under air-free conditions, catalyzed by a catalyst; then washing and drying the resulting reactants sequentially to obtain a COF-HSO3 catalyst; and subsequently, hydrating the α-olefins in a second organic solvent and water under the catalysis of the COF-HSO3 catalyst.

[0007] Preferably, the molar ratio of 1,3,5-tris(p-formylphenyl)benzene to p-phenylenediamine o-sulfonate is 1:1-2.

[0008] Preferably, the catalyst is at least one selected from acetic acid, formic acid, and trifluoroacetic acid.

[0009] Preferably, the first organic solvent is a mixed solution of 1,4-dioxane and mesitylene.

[0010] Preferably, the volume ratio of 1,4-dioxane to mesitylene is 1:0.5-2.

[0011] Preferably, the conditions for the aldehyde-amine condensation reaction include: a temperature of 100-150°C and a time of 2-4 days.

[0012] Preferably, the reagents used in the washing process are tetrahydrofuran and / or acetone.

[0013] Preferably, the drying conditions include: a temperature of 70-90°C, a time of 6-12 hours, and a vacuum degree of 0.06-0.08 MPa.

[0014] Preferably, the second organic solvent is at least one selected from isopropanol, ethylene glycol dimethyl ether, acetonitrile, and ethanol.

[0015] Preferably, the volume ratio of the second organic solvent to the water is 1:0.5-2.

[0016] Preferably, the α-olefin is at least one selected from α-nonene, α-heptene, α-dodecene, α-tetrideene, and α-tetradecene.

[0017] Preferably, the mass-to-volume ratio of the COF-HSO3 catalyst to the α-olefin is 1 g: (5-15) mL.

[0018] Preferably, the conditions for the hydration reaction include: a temperature of 100-140℃, a pressure of 1-4MPa, and a time of 4-8h.

[0019] The method for preparing secondary alcohols by catalytic hydration of α-olefins according to the present invention uses a sulfonic acid-modified covalent organic framework material synthesized from 1,3,5-tris(p-formylphenyl)benzene and p-phenylenediamine o-sulfonate as reactants as a catalyst for the catalytic hydration of α-olefins to prepare secondary alcohols. This catalyst possesses abundant sulfonic acid groups, a large pore size, and a high specific surface area. In the reaction process of catalytic hydration of α-olefins to prepare secondary alcohols, the reaction process is simple and easy to control, and the catalyst can be filtered, recovered, and reused. The method for preparing secondary alcohols by catalytic hydration of α-olefins according to the present invention achieves high α-olefin conversion and secondary alcohol yield. Attached Figure Description

[0020] Figure 1 This is a schematic diagram of the reaction formula for the preparation of the COF-HSO3 catalyst in this invention; Figure 2 This is a transmission electron microscope image of the COF-HSO3 catalyst prepared in Example 1 of this invention; Figure 3 The XRD pattern of the COF-HSO3 catalyst prepared in Example 1 of this invention; Figure 4 This is an adsorption-desorption curve of the COF-HSO3 catalyst prepared in Example 1 of this invention. Detailed Implementation

[0021] The following provides a detailed description of specific embodiments of the present invention. It should be understood that the specific embodiments described herein are for illustrative and explanatory purposes only and are not intended to limit the scope of the invention.

[0022] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0023] The method for preparing secondary alcohols by catalytic hydration of α-olefins according to the present invention includes: 1,3,5-tris(p-formylphenyl)benzene and p-phenylenediamine o-sulfonate undergoing an aldehyde-amine condensation reaction in a first organic solvent under air-free conditions, catalyzed by a catalyst; the resulting reactants are then washed and dried sequentially to obtain a COF-HSO3 catalyst; and the α-olefins are then hydrated in a second organic solvent and water under the catalysis of the COF-HSO3 catalyst.

[0024] In the method described in this invention, the molar ratio of 1,3,5-tris(p-formylphenyl)benzene and p-phenylenediamine o-sulfonic acid can be 1:1-2, preferably 1:1.2-1.8.

[0025] like Figure 1 As shown in the figure, the reaction formula for the preparation of COF-HSO3 catalyst from 1,3,5-tris(p-formylphenyl)benzene and p-phenylenediamine o-sulfonate is illustrated.

[0026] In the method described in this invention, the catalyst can be at least one selected from acetic acid, formic acid, and trifluoroacetic acid. In the most preferred embodiment, the catalyst is acetic acid.

[0027] In the method described in this invention, the first organic solvent can be a mixed solution of 1,4-dioxane and mesitylene. Preferably, the volume ratio of 1,4-dioxane to mesitylene is 1:0.5-2, specifically, for example, 1:0.5, 1:0.7, 1:1, 1:1.2, 1:1.6, 1:1.8, and 1:2.

[0028] In the method described in this invention, the conditions for the aldehyde-amine condensation reaction may include: a temperature of 100-150°C and a time of 2-4 days. Preferably, the conditions for the aldehyde-amine condensation reaction include: a temperature of 120-140°C and a time of 2.5-3.5 days. The specific operation process of the aldehyde-amine condensation reaction may include: adding the 1,3,5-tris(p-formylphenyl)benzene and the p-phenylenediamine o-sulfonate to a glass reaction tube; then injecting a mixed solution of 1,4-dioxane and mesitylene into the glass reaction tube; then adding the catalyst; and sonicating the resulting mixture at 20-40 kHz for 20-40 min. The glass reaction tube is then cooled with liquid nitrogen and evacuated (vacuum degree 0.07-0.09 MPa), and then transferred to an oven and heated to the target temperature for the reaction.

[0029] In the method described in this invention, the reagent used in the washing process can be tetrahydrofuran and / or acetone, preferably acetone. The washing process can be performed once or multiple times, preferably multiple times. The washing process is used to remove unreacted starting materials, byproducts, and residual solvents.

[0030] In the method described in this invention, the drying conditions may include: a temperature of 70-90°C, a time of 6-12 hours, and a vacuum degree of 0.06-0.08 MPa. Preferably, the drying conditions include: a temperature of 75-85°C, a time of 7-9 hours, and a vacuum degree of 0.07-0.08 MPa. The drying process can be carried out in various conventional drying ovens available in the art.

[0031] In the method described in this invention, the second organic solvent can be at least one selected from isopropanol, ethylene glycol dimethyl ether, acetonitrile, and ethanol. In the most preferred embodiment, the second organic solvent is isopropanol. The volume ratio of the second organic solvent to the water can be 1:0.5-2, preferably 1:0.8-1.5.

[0032] The specific surface area of ​​the COF-HSO3 catalyst prepared by the method of this invention can be 400-800 m². 2 / g, preferably 500-650m 2 / g; the average pore size can be 1-2 nm, preferably 1.3-1.8 nm. The specific surface area and pore size of the COF-HSO3 catalyst can be detected by nitrogen adsorption-desorption test.

[0033] In the method described in this invention, the α-olefin can be at least one selected from α-nonene, α-heptene, α-dodecene, α-trigecene, and α-tetradecene. The mass-to-volume ratio of the COF-HSO3 catalyst to the α-olefin can be 1 g:(5-15) mL, preferably 1 g:(8-12) mL. In the most preferred embodiment, the α-olefin is α-nonene. In a specific embodiment, the chemical reaction formula for the catalytic hydration of the α-olefin to prepare a secondary alcohol is shown below: .

[0034] In the method described in this invention, the conditions for the hydration reaction may include: a temperature of 100-140°C, a pressure of 1-4 MPa, and a time of 4-8 h. Preferably, the conditions for the hydration reaction include: a temperature of 110-130°C, a pressure of 1.5-3.5 MPa, and a time of 5-7 h. The hydration reaction can be carried out in a high-pressure autoclave reactor. The specific operation of the hydration reaction may include: introducing the α-olefin, the second organic solvent, and water into the high-pressure autoclave reactor, and introducing nitrogen gas to raise the reaction system to the target pressure, followed by heating to the target temperature for the reaction. In this invention, pressure refers to absolute pressure.

[0035] The following examples further illustrate the method for preparing secondary alcohols by catalytic hydration of α-olefins according to the present invention. These examples are implemented based on the technical solution of the present invention, providing detailed implementation methods and specific operating procedures; however, the scope of protection of the present invention is not limited to the following examples.

[0036] Unless otherwise specified, the experimental methods used in the following embodiments are conventional methods in the art. Unless otherwise specified, the experimental materials used in the following embodiments are commercially available.

[0037] In the following examples and comparative examples, the relevant parameters for the preparation of the COF-HSO3 catalyst and the catalytic hydration of α-olefins to prepare secondary alcohols were tested according to the following methods: Morphological and structural characterization: The morphology and structure of the COF-HSO3 catalyst were characterized and analyzed by transmission electron microscopy.

[0038] X-ray diffraction analysis: The structure of the COF-HSO3 catalyst was characterized and analyzed using an X-ray diffractometer.

[0039] Specific surface area and pore size analysis: The adsorption method was used under low-temperature nitrogen (77K). After vacuum degassing and impurity removal, the nitrogen adsorption-desorption isotherm was measured at liquid nitrogen temperature. The specific surface area was calculated using the BET equation and analyzed by t-plot / α. s-plot distinguishes between micropore volume and external surface area. The pore size distribution of micropores smaller than 2nm is fitted using HK, SF or DFT models. The resulting adsorption-desorption isotherms are mostly IUPAC type I isotherms. They are rapidly adsorbed and quickly reach saturation in the low specific pressure region, and generally have no obvious hysteresis loop, which can intuitively reflect the adsorption characteristics of micropores.

[0040] α-Olefin Conversion and Secondary Alcohol Selectivity: Conversion is calculated by the change in the amount of substrate before and after the reaction, i.e., Conversion = (Amount of substrate before reaction) / (Amount of substrate before reaction) The conversion rate is calculated as (amount of substrate after reaction) / (amount of substrate before reaction) × 100%. Selectivity is the proportion of the converted substrate to the target product, i.e., selectivity = amount of target product / amount of reacted substrate × 100%. Both can be obtained quantitatively by gas chromatography. The yield is the product of conversion and selectivity.

[0041] Example 1 Preparation of COF-HSO3 catalyst: 2 mmol of 1,3,5-tris(p-formylphenyl)benzene and 3 mmol of p-phenylenediamine o-sulfonic acid were added to a glass reaction tube. Then, 2 mL of a mixed solution of 1,4-dioxane and mesitylene (volume ratio 1:1) was injected into the glass reaction tube. 0.1 mL of acetic acid was added as a catalyst. The mixture was sonicated at 40 kHz for 30 min, and then the reaction tube was rapidly cooled with liquid nitrogen. The tube was then evacuated to a vacuum degree of 0.09 MPa, sealed, and placed in an oven at 120 °C for 3 days. The resulting powder precipitate was collected by filtration and washed three times alternately with tetrahydrofuran and acetone. The washed powder was transferred to a vacuum drying oven and dried at 80 °C and a vacuum degree of 0.08 MPa for 8 h to obtain COF-HSO3 catalyst A1. Figure 2 A transmission electron microscope (TEM) image of COF-HSO3 catalyst A1 is shown. Figure 3 The XRD pattern of COF-HSO3 catalyst A1 is shown. Figure 4 The adsorption-desorption curves of COF-HSO3 catalyst A1 are shown.

[0042] Catalytic hydration of α-olefins to prepare secondary alcohols: 1 g of COF-HSO3 catalyst A1, 10 mL of α-nonene, 20 mL of water and 20 mL of isopropanol were loaded into a 100 mL autoclave, and nitrogen gas was introduced at 3 MPa. The mixture was heated to 105 °C and stirred for 6 h to obtain secondary nonanol B1.

[0043] Example 2 Preparation of COF-HSO3 catalyst: 2 mmol of 1,3,5-tris(p-formylphenyl)benzene and 2 mmol of p-phenylenediamine o-sulfonic acid were added to a glass reaction tube. Then, 2 mL of a mixed solution of 1,4-dioxane and mesitylene (volume ratio 1:0.5) was injected into the glass reaction tube. 0.1 mL of acetic acid was then added as a catalyst. The mixture was sonicated at 40 kHz for 30 min, and then the reaction tube was rapidly cooled with liquid nitrogen. The tube was then evacuated to a vacuum degree of 0.09 MPa, sealed, and placed in an oven at 110 °C for 4 days. The resulting powder precipitate was collected by filtration and washed three times alternately with tetrahydrofuran and acetone. The washed powder was transferred to a vacuum drying oven and dried at 85 °C and a vacuum degree of 0.08 MPa for 6 h to obtain COF-HSO3 catalyst A2.

[0044] Catalytic hydration of α-olefins to prepare secondary alcohols: 1 g of COF-HSO3 catalyst A1, 10 mL of α-nonene, 25 mL of water and 15 mL of isopropanol were loaded into a 100 mL autoclave, and nitrogen gas at 3.5 MPa was introduced. The mixture was heated to 135 °C and stirred for 5 h to obtain secondary nonanol B2.

[0045] Example 3 Preparation of COF-HSO3 catalyst: 2 mmol of 1,3,5-tris(p-formylphenyl)benzene and 4 mmol of p-phenylenediamine o-sulfonic acid were added to a glass reaction tube. Then, 2 mL of a mixed solution of 1,4-dioxane and mesitylene (volume ratio 1:1.5) was injected into the glass reaction tube. 0.1 mL of acetic acid was then added as a catalyst. The mixture was sonicated at 40 kHz for 30 min, and then the reaction tube was rapidly cooled with liquid nitrogen. The tube was then evacuated to a vacuum degree of 0.08 MPa, sealed, and placed in an oven at 130 °C for 2 days. The resulting powder precipitate was collected by filtration and washed three times alternately with tetrahydrofuran and acetone. The washed powder was transferred to a vacuum drying oven and dried at 80 °C and a vacuum degree of 0.08 MPa for 6 h to obtain COF-HSO3 catalyst A3.

[0046] Catalytic hydration of α-olefins to prepare secondary alcohols: 1 g of COF-HSO3 catalyst A1, 10 mL of α-nonene, 15 mL of water and 25 mL of isopropanol were loaded into a 100 mL autoclave, and nitrogen gas at 2.5 MPa was introduced. The mixture was heated to 105 °C and stirred for 6 h to obtain secondary nonanol B3.

[0047] Example 4 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that the reaction temperature was adjusted to 110°C during the catalytic hydration of α-olefins to prepare the secondary alcohol, resulting in secondary nonanol B4.

[0048] Example 5 The secondary alcohol was prepared by catalytic hydration of α-olefins in accordance with the method of Example 1, except that the reaction temperature was adjusted to 120°C during the catalytic hydration of α-olefins to prepare the secondary alcohol, resulting in secondary nonanol B5.

[0049] Example 6 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that the reaction temperature was adjusted to 130°C during the catalytic hydration of α-olefins to prepare the secondary alcohol, resulting in secondary nonanol B6.

[0050] Example 7 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that the reaction temperature was adjusted to 140°C during the catalytic hydration of α-olefins to prepare the secondary alcohol, resulting in secondary nonanol B7.

[0051] Example 8 The secondary alcohol was prepared by catalytic hydration of α-olefins according to Example 1, except that the amount of α-nonene was adjusted to 6 mL and the reaction temperature was adjusted to 120 °C, resulting in secondary nonanol B8.

[0052] Example 9 The secondary alcohol was prepared by catalytic hydration of α-olefins in accordance with Example 1, except that isopropanol was replaced with acetonitrile and the reaction temperature was adjusted to 120°C to obtain secondary nonanol B9.

[0053] Example 10 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that isopropanol was replaced with ethylene glycol dimethyl ether and the reaction temperature was adjusted to 120°C to obtain secondary nonanol B10.

[0054] Example 11 The secondary alcohol was prepared by catalytic hydration of α-olefins in accordance with Example 1, except that isopropanol was replaced with ethanol and the reaction temperature was adjusted to 120°C to obtain secondary nonanol B11.

[0055] Example 12 The secondary alcohol was prepared by catalytic hydration of α-olefins according to Example 1, except that the nitrogen pressure was adjusted to 1 MPa and the reaction temperature was adjusted to 120 °C during the catalytic hydration of α-olefins to prepare the secondary alcohol, resulting in secondary nonanol B12.

[0056] Example 13 The secondary alcohol was prepared by catalytic hydration of α-olefins according to Example 1, except that the nitrogen pressure was adjusted to 2 MPa and the reaction temperature was adjusted to 120 °C during the catalytic hydration of α-olefins to prepare the secondary alcohol, resulting in secondary nonanol B13.

[0057] Example 14 The secondary alcohol was prepared by catalytic hydration of α-olefins according to Example 1, except that the nitrogen pressure was adjusted to 4 MPa and the reaction temperature was adjusted to 120 °C during the catalytic hydration of α-olefins to prepare the secondary alcohol, resulting in secondary nonanol B14.

[0058] Example 15 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that α-nonene was replaced with α-heptene and the reaction temperature was adjusted to 120°C to obtain secondary heptanol B15.

[0059] Example 16 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that α-nonene was replaced with α-dodecene and the reaction temperature was adjusted to 120°C to obtain secondary dodecyl alcohol B16.

[0060] Example 17 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that α-nonene was replaced with α-tridecene and the reaction temperature was adjusted to 120°C to obtain secondary tridecyl alcohol B17.

[0061] Example 18 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that α-nonene was replaced with α-tetradecene and the reaction temperature was adjusted to 120°C to obtain secondary tetradecyl alcohol B18.

[0062] Example 19 The secondary alcohol was prepared by catalytic hydration of α-olefins in accordance with the method of Example 1, except that the COF-HSO3 catalyst A1 was reused 10 times in the process of catalytic hydration of α-olefins to prepare secondary alcohols, and the product prepared in the last time was secondary nonanol B19.

[0063] Comparative Example 1 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that 1,3,5-tris(p-formylphenyl)benzene was replaced with mesitylene, resulting in COF-HSO3 catalyst D1 and secondary nonanol E1.

[0064] Comparative Example 2 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that p-phenylenediamine o-sulfonic acid was replaced with benzidine disulfonic acid, resulting in COF-HSO3 catalyst D2 and secondary nonanol E2.

[0065] Comparative Example 3 The secondary alcohol was prepared by catalytic hydration of α-olefins in the manner described in Example 1, except that no water was added during the catalytic hydration of α-olefins to prepare the secondary alcohol, resulting in secondary nonanol E3.

[0066] The performance parameters of the COF-HSO3 catalysts prepared in the above embodiments and comparative examples are shown in Table 1 below.

[0067] Table 1

[0068] As can be seen from the results in Table 1, the method for preparing secondary alcohols by catalytic hydration of α-olefins described in this invention has a high α-olefin conversion rate and secondary alcohol yield.

[0069] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A method for preparing secondary alcohols by catalytic hydration of α-olefins, characterized in that, The method includes: 1,3,5-tris(p-formylphenyl)benzene and p-phenylenediamine o-sulfonate undergoing an aldehyde-amine condensation reaction in a first organic solvent under the catalysis of a catalyst, followed by washing and drying the resulting reactants to obtain a COF-HSO3 catalyst, and then hydrating α-olefins in a second organic solvent and water under the catalysis of the COF-HSO3 catalyst.

2. The method according to claim 1, characterized in that, The molar ratio of 1,3,5-tris(p-formylphenyl)benzene to p-phenylenediamine o-sulfonate is 1:1-2.

3. The method according to claim 1 or 2, characterized in that, The catalyst is at least one of acetic acid, formic acid, and trifluoroacetic acid.

4. The method according to any one of claims 1-3, characterized in that, The first organic solvent is a mixed solution of 1,4-dioxane and mesitylene; Preferably, the volume ratio of 1,4-dioxane to mesitylene is 1:0.5-2.

5. The method according to any one of claims 1-4, characterized in that, The conditions for the aldehyde-amine condensation reaction include: a temperature of 100-150℃ and a time of 2-4 days.

6. The method according to any one of claims 1-5, characterized in that, The reagents used in the washing process are tetrahydrofuran and / or acetone.

7. The method according to any one of claims 1-6, characterized in that, The drying conditions include: a temperature of 70-90℃, a time of 6-12 hours, and a vacuum degree of 0.06-0.08 MPa.

8. The method according to any one of claims 1-7, characterized in that, The second organic solvent is at least one of isopropanol, ethylene glycol dimethyl ether, acetonitrile, and ethanol; Preferably, the volume ratio of the second organic solvent to the water is 1:0.5-2.

9. The method according to any one of claims 1-8, characterized in that, The α-olefin is at least one selected from α-nonene, α-heptene, α-dodecene, α-tetrideene, and α-tetradecene; Preferably, the mass-to-volume ratio of the COF-HSO3 catalyst to the α-olefin is 1 g: (5-15) mL.

10. The method according to any one of claims 1-9, characterized in that, The conditions for the hydration reaction include: a temperature of 100-140℃, a pressure of 1-4MPa, and a time of 4-8h.

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