Catalytic method for joint production of alkylene oxide and diol

Abstract

The invention belongs to the technical field of heterogeneous catalysis, and particularly relates to a catalytic method for joint production of alkylene oxide and diol, which comprises the following steps: S1, sequentially adding an organic solvent, hydrogen peroxide, alpha-olefin and a regulator into a tank reactor according to a certain proportion, and uniformly stirring; adding the Ti-M-MFI catalyst into the reactor, and sealing the reactor; and S2, introducing N2 into the reactor until the pressure is 0.1-1 MPa, heating to 40-60 DEG C while stirring, and reacting for 0.5-1 hour. And S3, rapidly reducing the reaction temperature to 20 DEG C or below, stopping stirring, discharging N2, and reducing the pressure in the reactor to normal pressure. And S4, rapidly raising the temperature to 60-80 DEG C, starting stirring, and reacting for 0.5-1 hour. According to the method, N2 is used for increasing the system pressure, the solubility of long-chain olefin in the reaction solution is maintained, the epoxidation step is promoted to be efficiently carried out, the temperature-variable reaction process is suitable for the epoxidation step and the hydration step respectively, and the reaction efficiency is improved.

Description

Technical Field

[0001] The present invention belongs to the technical field of heterogeneous catalysis and relates to a method for jointly producing 1,2-epoxyalkanes and 1,2-diols. Background Art

[0002] 1,2-Epoxyalkanes, especially long-chain epoxyalkanes, are important fine chemical products, mainly used for producing 1,2-diols. The latter can be used for producing fungicides and is also an important component of moisturizers and emollients in cosmetics, having excellent moisturizing and lubricating properties. It can also be used as a solvent in the pharmaceutical and chemical fields and as a food additive in the food field, with high economic value. Currently, there are large gaps in the global market for 1,2-pentanediol and 1,2-diols with longer chains, and China's consumption basically relies on imports.

[0003] Chinese Patent CN1552684A discloses a method for synthesizing 1,2-pentanediol from n-pentene, formic acid, and hydrogen peroxide through epoxidation reaction and hydrolysis reaction, and the epoxidation reaction temperature is 20 - 10°C. This patent uses low-temperature reaction and replaces peracetic acid with performic acid, improving the process safety. However, there are also problems such as excessive formic acid, easy formation of by-products during the reaction process, and separation and recovery of sodium formate. Patent DE3442937 reports that 1-pentene and peroxypropionic acid are continuously reacted in solvent benzene to obtain 1,2-epoxypentane. The recovery of by-product propionic acid in this process is difficult, and the solvent benzene is highly toxic. US Patents US4605795 and US4479021 respectively disclose processes for epoxidizing 1-pentene with peroxypropionic acid and peracetic acid to produce 1,2-epoxypentane and then generating 1,2-pentanediol through saponification reaction. These processes have problems such as difficult recovery of by-products and difficult control of the safety of peracetic acid. Patent WO2017157832A1 uses a TS-1 / Hβ molecular sieve mixed catalyst for a one-pot reaction, but there is a problem that the acidity of the Hβ molecular sieve is too strong, resulting in rapid and ineffective decomposition of hydrogen peroxide; moreover, it is difficult to separate and recover the two catalysts. Chinese Patent CN102010293A discloses a method for using a titanium silicalite molecular sieve to catalyze 1-pentene to form 1,2-epoxypentane and then hydrolyzing it to obtain 1,2-pentanediol. In this method, when generating 1,2-epoxypentane, in order to convert as much hydrogen peroxide as possible, a reaction time of 3 h is required, and its reaction time is relatively long, increasing the industrialization cost.

[0004] From the above solutions, most of the existing methods for producing 1,2-epoxyalkanes and 1,2-diols are obtained step by step, that is, first obtaining epoxyalkanes and then using the epoxyalkanes to obtain the target product diol. There is no method that can obtain the two target products simultaneously, and there are problems such as poor economy or environmental pollution. It is necessary to develop a green and environmentally friendly and highly economical method. Summary of the Invention

[0005] To solve the problems existing in the prior art, the present invention provides a catalytic method for epoxidation-hydration of α-olefin and hydrogen peroxide to produce 1,2-epoxyalkane and the corresponding hydrolysis product 1,2-diol. This method uses a molecular sieve catalyst containing oxidation sites and acid sites, and by regulating the relative contents of the two sites, the ratio of 1,2-epoxyalkane and 1,2-diol can be adjusted to meet the industry's demand for product output.

[0006] Specifically, a catalytic method for co-producing epoxyalkane and diol provided by the present invention includes the following steps: S1. Add an organic solvent, hydrogen peroxide, α-olefin, and a regulator into a batch reactor in sequence, and stir evenly; add the Ti-M-MFI catalyst into the reactor and seal the reactor. S2. Introduce N2 into the reactor to 0.1~1 MPa, stir and heat up to 40~60 °C, and react for 0.5~1 h. S3. Lower the reaction temperature below 20 °C, stop stirring, discharge N2, and reduce the pressure in the reactor to atmospheric pressure. S4. Heat up to 60~80 °C again, start stirring, and react for 0.5~1 h.

[0007] Furthermore, the Ti-M-MFI catalyst is an oxidation-acid bifunctional catalyst.

[0008] Preferably, the Ti-M-MFI catalyst is an oxidation-acid bifunctional catalyst prepared by a sequential introduction method, and its framework contains titanium and trivalent ion M 3+ , and the sequential introduction method is to first introduce titanium into the molecular sieve framework to form oxidation sites, and then introduce trivalent ion M 3+ , to form acid sites; preferably, the trivalent ion M 3+ is selected from at least one of 3+ B 3+ Al 3+ Ga.

[0009] Furthermore, in step S1, the organic solvent is one or a combination of acetonitrile and acetone; preferably, the organic solvent is a mixed solvent of acetonitrile and acetone, and the volume ratio of acetonitrile to acetone in the mixed solvent is 1 : (0.1~10).

[0010] Furthermore, in step S1, the mass ratio of the Ti-M-MFI catalyst to hydrogen peroxide is 1:(1~10); preferably, the mass ratio is 1:(2~5).

[0011] Further, in step S1, the α-olefin is an α-olefin with 5 or more carbon atoms; the molar ratio of hydrogen peroxide to α-olefin is 1:(0.8 - 10); preferably, the molar ratio is 1:(1 - 5).

[0012] Further, in step S1, the molar ratio of hydrogen peroxide to organic solvent is 1:(5 - 50); preferably, the molar ratio is 1:(20 - 30).

[0013] Further, in step S1, the regulator is ammonium acetate, and the molar ratio of ammonium acetate to hydrogen peroxide is 1:(100 - 2000); preferably, the molar ratio is 1:(500 - 1000).

[0014] Further, in step S1, the concentration of the hydrogen peroxide raw material is 30wt% - 70wt%; preferably, the concentration is 47.5wt% - 55wt%.

[0015] Further, in step S3, the reaction temperature is rapidly decreased to below 20°C within 10 s; in step S4, the reaction temperature is rapidly increased to 60 - 80°C again within 10 s. This is to reduce the ineffective decomposition of hydrogen peroxide.

[0016] Compared with the prior art, the beneficial effects of the present invention are as follows: (1) The combined production method of 1,2-epoxyalkane / 1,2-diol provided by the present invention innovatively uses an oxidation-acid bifunctional catalyst, especially an oxidation-acid bifunctional catalyst prepared by a sequential introduction method. The excellent catalytic oxidation and acid catalytic activities of this catalyst enable the epoxidation-hydration process to proceed efficiently. By regulating the relative contents of the two sites, the ratio of 1,2-epoxyalkane and 1,2-diol can be adjusted to meet the industry's demand for product output.

[0017] (2) During the reaction process, N2 is used to increase the system pressure, maintain the solubility of long-chain olefins in the reaction solution, and promote the efficient progress of the epoxidation step. Moreover, as an inert gas with a relatively high heat capacity, N2 can absorb and disperse the heat released by the reaction, preventing local overheating from causing an increase in side reactions and rapid deactivation of the catalyst.

[0018] (3) In the initial stage of the variable-temperature reaction process, the epoxidation step of α-olefin and hydrogen peroxide mainly occurs. A lower temperature is beneficial to the effective conversion of hydrogen peroxide. In the later stage, the hydration step of epoxyalkane mainly occurs. A higher temperature can promote the hydration step and the diffusion of diol products. And the α-olefin is mainly a long-chain olefin with 5 or more carbon atoms, achieving the one-step production of two target products, epoxyalkane and diol, from long-chain olefins. Specific Embodiments

[0019] The present invention will be further described below in conjunction with specific embodiments, but it is not limited to the present invention in any way.

[0020] The Ti-M-MFI catalyst can be prepared by a hydrothermal synthesis method or by a sequential introduction method.

[0021] If prepared by the sequential introduction method, its framework contains titanium and trivalent ion M 3+ , and the sequential introduction method is to first introduce titanium into the zeolite framework to form oxidation sites, and then introduce trivalent ion M 3+ , to form acid sites; preferably, the trivalent ion M 3+ is selected from at least one of B 3+ , Al 3+ , Ga 3+ : S1. Introduction of oxidation sites: Mix a silicon source, a template agent, and water to form a suspension, hydrolyze to obtain a hydrolyzed solution of silicon; mix a titanium source, a template agent, isopropanol, and water to form a suspension, hydrolyze to obtain a hydrolyzed solution of titanium; mix the hydrolyzed solution of silicon with the hydrolyzed solution of titanium, remove alcohol; finally, put the clarified solution into a crystallization kettle and crystallize at 150-220 °C for 12-72 h; the obtained suspension is subjected to solid-liquid separation, drying, and calcination at 500-900 °C for 2-8 h to obtain a zeolite catalyst containing oxidation sites, denoted as Ti-MFI.

[0022] S2. Introduction of acid sites: Mix heteroatom M 3+ , a template agent, an ammonium source, and water to prepare a treatment solution, add Ti-MFI to the treatment solution, and stir evenly; put the solid-liquid mixture into a crystallization kettle and treat it at 130-230 °C for 12-72 h; the obtained product is subjected to solid-liquid separation, drying, and calcination at 500-900 °C for 2-8 h to obtain a zeolite catalyst containing both oxidation sites and acid sites, denoted as Ti-M-MFI.

[0023] Example 1 Preparation of Ti-M-MFI catalyst: S1: Add 35.5 g of tetraethyl orthosilicate to a three-necked flask, add 32.0 g of aqueous tetrapropylammonium hydroxide solution and 28.4 g of water at 40 °C with stirring to hydrolyze tetraethyl orthosilicate for 4 h; add 1.4 g of tetrabutyl titanate to 10.6 g of isopropanol, and sequentially add 12.1 g of tetrapropylammonium hydroxide solution and 14.2 g of water with stirring to hydrolyze at room temperature for 0.5 h to obtain a hydrolyzate of tetrabutyl titanate. Mix the hydrolyzates of silicon ester and titanium ester, and remove alcohol at 85 °C for 6 h. Put the obtained clarified solution into a crystallization kettle and crystallize at 170 °C for 48 h. After washing and drying the crystallization product, calcine it at 540 °C for 5 h, denoted as Ti-MFI.

[0024] S2: Add 3.3 mL of tetrapropylammonium hydroxide solution, 2.24 g of ammonium carbonate, and 0.12 g of aluminum isopropoxide to 66 mL of water in sequence, stir at 40 °C for 0.5 h to obtain a treatment solution. Weigh 7.0 g of the Ti-MFI synthesized by S1 and add it to the treatment solution, stir at 40 °C for 4 h. Transfer the obtained suspension to a stainless-steel crystallization kettle with a polytetrafluoroethylene liner, treat at 170 °C for 24 h, centrifuge to separate the solid, dry at 80 °C for 12 h, and calcine at 540 °C for 6 h to obtain the Ti-Al-MFI catalyst.

[0025] Add 20 mL of acetonitrile / acetone mixed solvent (volume ratio 1:1), 1.5 mL of 30 wt% hydrogen peroxide solution, 2.3 mg of ammonium acetate, and 5 mL of 1-pentene to a batch reactor in sequence, stir evenly; add 0.2 g of the Ti-Al-MFI catalyst to the solution, seal the reactor; introduce N2 into the reactor until the gauge pressure reaches 0.5 MPa, heat up to 50 °C, and react with stirring for 1 h; quickly lower the reaction temperature below 20 °C within 10 s, discharge N2 to atmospheric pressure, quickly heat up the reaction temperature to 70 °C again within 10 s, and react with stirring for another 1 h. Centrifuge the product after the reaction to separate the supernatant for analysis, and obtain a hydrogen peroxide conversion rate of 96.8%, an effective utilization rate of hydrogen peroxide of 97.4%, a selectivity of 1,2-epoxypentane of 45.9%, and a selectivity of 1,2-pentanediol of 54.1%.

[0026] Example 2 The preparation of the Ti-M-MFI catalyst is the same as that in Example 1.

[0027] Add 20 mL of acetonitrile / acetone mixed solvent (volume ratio 1:0.5), 1.5 mL of 30 wt% hydrogen peroxide solution, 2.3 mg of ammonium acetate, and 8.5 mL of 1-pentene to a batch reactor in sequence, stir evenly; add 0.2 g of the catalyst to the solution, seal the reactor; introduce N2 into the reactor until the gauge pressure reaches 0.1 MPa, heat up to 40 °C, and react with stirring for 0.5 h; quickly lower the reaction temperature below 20 °C within 10 s, discharge N2 to atmospheric pressure, quickly heat up the reaction temperature to 70 °C again within 10 s, and react with stirring for another 1 h. Centrifuge the product after the reaction to separate the supernatant for analysis, and obtain a hydrogen peroxide conversion rate of 98.7%, an effective utilization rate of hydrogen peroxide of 98.2%, a selectivity of 1,2-epoxypentane of 67.4%, and a selectivity of 1,2-pentanediol of 32.6%.

[0028] Example 3 The preparation of the Ti-M-MFI catalyst is the same as that in Example 1.

[0029] 20 mL of acetonitrile / acetone mixed solvent (volume ratio 1:10), 1.5 mL of 30 wt% hydrogen peroxide, 2.3 mg of ammonium acetate, and 5 mL of 1-pentene were successively added to a autoclave reactor and stirred evenly; 0.2 g of catalyst was added to the solution and the reactor was sealed; N2 was introduced into the reactor until the gauge pressure reached 0.2 MPa, the temperature was raised to 40 °C, and the reaction was carried out with stirring for 1 h; the reaction temperature was rapidly lowered below 20 °C within 10 s, N2 was discharged to atmospheric pressure, the reaction temperature was rapidly raised to 80 °C again within 10 s, and the reaction was carried out with stirring for another 1 h. The supernatant of the reaction product was centrifuged and analyzed, and the conversion rate of hydrogen peroxide was 94.5%, the effective utilization rate of hydrogen peroxide was 89.4%, the selectivity of 1,2-epoxypentane was 21.6%, and the selectivity of 1,2-pentanediol was 78.4%.

[0030] Example 4 The Ti-M-MFI catalyst was prepared in the same manner as in Example 1.

[0031] 20 mL of acetonitrile / acetone mixed solvent (volume ratio 1:1), 1.5 mL of 30 wt% hydrogen peroxide, 2.3 mg of ammonium acetate, and 1.7 mL of 1-pentene were successively added to a autoclave reactor and stirred evenly; 0.2 g of catalyst was added to the solution and the reactor was sealed; N2 was introduced into the reactor until the gauge pressure reached 0.1 MPa, the temperature was raised to 45 °C, and the reaction was carried out with stirring for 1 h; the reaction temperature was rapidly lowered below 20 °C within 10 s, N2 was discharged to atmospheric pressure, the reaction temperature was rapidly raised to 65 °C again within 10 s, and the reaction was carried out with stirring for another 0.5 h. The supernatant of the reaction product was centrifuged and analyzed, and the conversion rate of hydrogen peroxide was 87.6%, the effective utilization rate of hydrogen peroxide was 86.7%, the selectivity of 1,2-epoxypentane was 61.4%, and the selectivity of 1,2-pentanediol was 38.6%.

[0032] Example 5 The Ti-M-MFI catalyst was prepared in the same manner as in Example 1.

[0033] 13.3 mL of acetonitrile / acetone mixed solvent (volume ratio 1:0.1), 1.5 mL of 30 wt% hydrogen peroxide, 1.2 mg of ammonium acetate, and 5 mL of 1-pentene were successively added to a autoclave reactor and stirred evenly; 0.3 g of catalyst was added to the solution and the reactor was sealed; N2 was introduced into the reactor until the gauge pressure reached 0.5 MPa, the temperature was raised to 60 °C, and the reaction was carried out with stirring for 1 h; the reaction temperature was rapidly lowered below 20 °C within 10 s, N2 was discharged to atmospheric pressure, the reaction temperature was rapidly raised to 80 °C again within 10 s, and the reaction was carried out with stirring for another 1 h. The supernatant of the reaction product was centrifuged and analyzed, and the conversion rate of hydrogen peroxide was 98.9%, the effective utilization rate of hydrogen peroxide was 95.3%, the selectivity of 1,2-epoxypentane was 43.1%, and the selectivity of 1,2-pentanediol was 56.9%.

[0034] Example 6 The Ti-M-MFI catalyst was prepared in the same manner as in Example 1.

[0035] 13.3 mL of an acetonitrile / acetone mixed solvent (volume ratio 1:3), 1.5 mL of 30 wt% hydrogen peroxide, 1.2 mg of ammonium acetate, and 2.5 mL of 1-pentene were successively added to a autoclave reactor and stirred evenly; 0.1 g of the catalyst was added to the solution and the autoclave was sealed; N2 was introduced into the autoclave until the gauge pressure reached 0.2 MPa, the temperature was raised to 60 °C, and the reaction was carried out with stirring for 0.5 h; the reaction temperature was rapidly lowered to below 20 °C within 10 s, N2 was discharged to atmospheric pressure, the reaction temperature was rapidly raised to 60 °C again within 10 s, and the reaction was carried out with stirring for another 1 h. The supernatant of the reaction product was centrifuged and analyzed, and the conversion rate of hydrogen peroxide was 89.1%, the effective utilization rate of hydrogen peroxide was 89.6%, the selectivity of 1,2-epoxypentane was 51.4%, and the selectivity of 1,2-pentanediol was 48.6%.

[0036] Example 7 The Ti-M-MFI catalyst was prepared in the same manner as in Example 1.

[0037] 20 mL of an acetonitrile / acetone mixed solvent (volume ratio 1:0.25), 1.5 mL of 30 wt% hydrogen peroxide, 2.3 mg of ammonium acetate, and 3 mL of 1-hexene were successively added to a autoclave reactor and stirred evenly; 0.2 g of the catalyst was added to the solution and the autoclave was sealed; N2 was introduced into the autoclave until the gauge pressure reached 0.6 MPa, the temperature was raised to 50 °C, and the reaction was carried out with stirring for 1 h; the reaction temperature was rapidly lowered to below 20 °C within 10 s, N2 was discharged to atmospheric pressure, the reaction temperature was rapidly raised to 70 °C again within 10 s, and the reaction was carried out with stirring for another 1 h. The supernatant of the reaction product was centrifuged and analyzed, and the conversion rate of hydrogen peroxide was 96.8%, the effective utilization rate of hydrogen peroxide was 94.0%, the selectivity of 1,2-epoxyhexane was 42.9%, and the selectivity of 1,2-hexanediol was 57.1%.

[0038] Example 8 The Ti-M-MFI catalyst was prepared in the same manner as in Example 1.

[0039] 20 mL of acetonitrile / acetone mixed solvent (volume ratio 1:4), 1.5 mL of 30 wt% hydrogen peroxide, 2.3 mg of ammonium acetate, and 3.5 mL of 1-hexene were successively added to a batch reactor and stirred evenly; 0.1 g of catalyst was added to the solution and the reactor was sealed; N2 was introduced into the reactor until the gauge pressure reached 0.8 MPa, the temperature was raised to 60 °C, and the reaction was carried out for 1 h with stirring; the reaction temperature was rapidly lowered below 20 °C within 10 s, N2 was discharged to atmospheric pressure, the reaction temperature was rapidly raised to 80 °C again within 10 s, and the reaction was carried out for another 1 h with stirring. The supernatant of the reaction product was centrifuged and analyzed, and the hydrogen peroxide conversion rate was 87.6%, the effective utilization rate of hydrogen peroxide was 91.7%, the selectivity of 1,2-epoxyhexane was 27.4%, and the selectivity of 1,2-hexanediol was 72.6%.

[0040] Example 9 The Ti-M-MFI catalyst was prepared in the same manner as in Example 1.

[0041] 18 mL of acetonitrile / acetone mixed solvent (volume ratio 1:4), 1.5 mL of 30 wt% hydrogen peroxide, 1.2 mg of ammonium acetate, and 4.5 mL of 1-heptene were successively added to a batch reactor and stirred evenly; 0.2 g of catalyst was added to the solution and the reactor was sealed; N2 was introduced into the reactor until the gauge pressure reached 0.6 MPa, the temperature was raised to 60 °C, and the reaction was carried out for 1 h with stirring; the reaction temperature was rapidly lowered below 20 °C within 10 s, N2 was discharged to atmospheric pressure, the reaction temperature was rapidly raised to 60 °C again within 10 s, and the reaction was carried out for another 1 h with stirring. The supernatant of the reaction product was centrifuged and analyzed, and the hydrogen peroxide conversion rate was 96.1%, the effective utilization rate of hydrogen peroxide was 97.6%, the selectivity of 1,2-epoxyheptane was 64.1%, and the selectivity of 1,2-heptanediol was 35.9%.

[0042] Example 10 The Ti-M-MFI catalyst was prepared in the same manner as in Example 1.

[0043] 18 mL of acetonitrile / acetone mixed solvent (volume ratio 1:0.25), 1.5 mL of 30 wt% hydrogen peroxide, 2.3 mg of ammonium acetate, and 4.5 mL of 1-octene were successively added to a batch reactor and stirred evenly; 0.2 g of catalyst was added to the solution and the reactor was sealed; N2 was introduced into the reactor until the gauge pressure reached 0.5 MPa, the temperature was raised to 60 °C, and the reaction was carried out for 1 h with stirring; the reaction temperature was rapidly lowered below 20 °C within 10 s, N2 was discharged to atmospheric pressure, the reaction temperature was rapidly raised to 80 °C again within 10 s, and the reaction was carried out for another 1 h with stirring. The supernatant of the reaction product was centrifuged and analyzed, and the hydrogen peroxide conversion rate was 98.7%, the effective utilization rate of hydrogen peroxide was 98.3%, the selectivity of 1,2-epoxyoctane was 39.5%, and the selectivity of 1,2-octanediol was 60.5%.

[0044] In summary, the method provided by the present invention can more efficiently convert α-olefins into 1,2-epoxyalkanes and 1,2-diols by pressurizing with N2.

[0045] The above is only a preferred specific embodiment of the present invention, but the protection scope of the present invention is not limited thereto. Any person skilled in the art within the technical scope disclosed by the present invention should cover within the protection scope of the present invention by making equivalent substitutions or changes according to the technical solution and inventive concept of the present invention.

Claims

1. A catalytic method for co-producing alkylene oxides and diols, characterized in that, It includes the following steps: S1. Add an organic solvent, hydrogen peroxide, an α-olefin, and a regulator into a batch reactor in sequence, and stir evenly; add a Ti-M-MFI catalyst into the reactor and seal the reactor. S2. Introduce N2 into the reactor to 0.1~1 MPa, stir and heat up to 40~60 °C, and react for 0.5~1 h. S3. Lower the reaction temperature below 20 °C, stop stirring, discharge N2, and reduce the pressure in the reactor to atmospheric pressure. S4. Heat up to 60~80 °C again, start stirring, and react for 0.5~1 h.

2. The method according to claim 1, wherein In step S1, the Ti-M-MFI catalyst is an oxidation-acid bifunctional catalyst.

3. The method according to claim 1, wherein The Ti-M-MFI catalyst is an oxidation-acid bifunctional catalyst prepared by a sequential introduction method, and its framework contains titanium and trivalent ion M 3+ , and the sequential introduction method is to first introduce titanium into the molecular sieve framework to form oxidation sites, and then introduce trivalent ion M 3+ to form acid sites; preferably, the trivalent ion M 3+ is selected from at least one of B 3+ , Al 3+ , Ga 3+ .

4. The method according to claim 1, wherein In step S1, the organic solvent is one or a combination of two of acetonitrile and acetone; preferably, the organic solvent is a mixed solvent of acetonitrile and acetone, and the volume ratio of acetonitrile to acetone in the mixed solvent is 1:(0.1~10).

5. The method according to claim 1, wherein In step S1, the mass ratio of the Ti-M-MFI catalyst to hydrogen peroxide is 1:(1~10); preferably, the mass ratio is 1:(2~5).

6. The method according to claim 1, characterized in that, In step S1, the α-olefin is an α-olefin with 5 or more carbon atoms; the molar ratio of hydrogen peroxide to the α-olefin is 1:(0.8~10); preferably, the molar ratio is 1:(1~5).

7. The method according to claim 1, characterized in that, In step S1, the molar ratio of hydrogen peroxide to the organic solvent is 1:(5~50); preferably, the molar ratio is 1:(20~30).

8. The method according to claim 1, wherein In step S1, the regulator is ammonium acetate, and the molar ratio of ammonium acetate to hydrogen peroxide is 1:(100~2000); preferably, the molar ratio is 1:(500~1000).

9. The method according to claim 1, wherein In step S1, the concentration of the hydrogen peroxide raw material is 30 wt%~70 wt%; preferably, the concentration is 47.5 wt%~55 wt%.

10. According to claim 1, in step S3, lower the reaction temperature below 20 °C within 10 s; in step S4, heat up the reaction temperature to 60~80 °C again within 10 s.