A hydroformylation catalyst, its preparation method and application

Abstract

The application belongs to the technical field of metal-based catalysts, and discloses a hydroformylation catalyst as well as a preparation method and application thereof. A new type of hydroformylation catalyst is prepared through 5-step chemical reactions by using cheap and readily available polystyrene as a reaction raw material, and the catalyst can be directly filtered after the reaction, so that the cost and difficulty of separation of the catalytic system are greatly reduced. The catalyst prepared by the preparation method solves the problem that the reaction raw material, the product and the catalyst are difficult to separate in the hydroformylation process. Through the method, the product can be obtained in a high yield and high selectivity under relatively mild conditions, the loss of the catalytic system can be reduced, the activity of the catalytic system can be maintained after multiple uses, and the production cost is reduced.

Description

Technical Field

[0001] The present invention relates to the technical field of metal-based catalysts, and in particular to a hydroformylation catalyst and a preparation method and application thereof. Background Art

[0002] Olefin hydroformylation is the reaction of α-olefins and synthesis gas to produce higher-carbon linear aldehydes. The aldehydes produced by this reaction are widely used in fragrances, surfactants, plasticizers, and solvents. Among the many olefin hydroformylation reactions, the reaction of isooctene to isononanal has received extensive research. This is because isononanal is an important organic chemical raw material, widely used in plasticizers, surfactants, fragrances, detergents, and organic synthesis. Moreover, isononanal can be subsequently converted into many high-value-added fine chemical products. Reduction can produce isononanol, and oxidation can produce isononanoic acid. Due to the unique properties of highly branched isononanoic acid, such as excellent wettability, permeability, and emulsification, it also has important applications in lubricants, industrial detergents, and other industries.

[0003] Currently, the reaction of isooctene to isononanal is still at the laboratory stage and has not yet entered industrial application. Although some related hydroformylation processes have been reported, current research focuses on homogeneous catalytic systems, water / oil two-phase catalytic systems, and heterogeneous solid-supported catalytic systems. Furthermore, the current isooctene hydroformylation reaction faces challenges in catalyst and ligand recovery, and the use of phosphine-containing ligands can pollute the natural environment.

[0004] In view of the problems existing in the reaction of preparing isononanal from isooctene, developing an olefin hydroformylation catalyst that can promote the conversion rate of isooctene and has low production cost is the current research focus in this field. Summary of the Invention

[0005] The present invention aims to overcome the shortcomings of the prior art and provide a hydroformylation catalyst, a preparation method and an application thereof. When the catalyst is applied to a hydroformylation reaction, isononanal can be obtained in high yield and high selectivity under relatively mild conditions, while reducing the loss of the catalytic system.

[0006] To achieve the above object, the technical solution adopted by the present invention is as follows:

[0007] In a first aspect, the present invention provides a method for preparing a hydroformylation catalyst, the method comprising the following steps:

[0008] S1. Using polystyrene as a raw material, undergoing FC acylation reaction with aluminum chloride and acetyl chloride to generate the catalyst intermediate A described in formula (1);

[0009] S2, subjecting the intermediate A described in step S1 to a Baeyer-Villiger oxidation reaction in an acid catalyst and an oxidant to generate the catalyst intermediate B described in formula (2);

[0010] S3, subjecting the intermediate B described in step S2 to a reduction reaction with a reducing agent to generate the catalyst intermediate C described in formula (3);

[0011] S4, reacting the intermediate C described in step S3 with a chlorophosphite in the presence of an organic base to produce a catalyst intermediate D described in formula (4);

[0012] S5, immersing the catalyst intermediate D described in step S4 in a rhodium-containing compound solution, filtering and drying, to obtain a hydroformylation catalyst, wherein the chemical formula of the hydroformylation catalyst is Rh-(C 12 H 17 O3P) n ;

[0013]

[0014] The value of n is 100-1000.

[0015] Industrially, hydroformylation catalysts have evolved through four generations. The first generation of hydroformylation catalysts was cobalt-based. Due to the low reactivity of cobalt, the reaction typically required harsh reaction conditions, such as high pressure and temperature. The second generation of hydroformylation catalysts was rhodium-based catalytic systems. Among them, rhodium-based catalysts modified with phosphine ligands were widely used, exhibiting extremely excellent reactivity and selectivity for linear aldehydes. However, while this catalyst had excellent catalytic effects, it was plagued by the difficulty of separating the catalyst from the product, resulting in high costs. The third generation of hydroformylation catalysts primarily employed a two-phase system, using water-soluble or ionic liquid-solidified catalysts to facilitate separation from the organic product. The fourth-generation rhodium / phosphine water-soluble HRh(CO)(TPPTS)3 catalyst, due to the high boiling point of high-carbon aldehydes / alcohols, must be separated from the catalyst by flash distillation at high temperature when prepared from high-carbon olefins. Rhodium catalyst activity is 1,000 times higher than cobalt catalysts, but the price of rhodium is 3,500 times that of cobalt. In hydroformylation reactions, homogeneous rhodium-phosphine catalytic systems can exhibit excellent conversion rates and selectivity, but the catalyst is difficult to separate from the product and reuse. Rhodium is a precious metal, and its loss in industry significantly increases process costs. In the current process flow, the reaction liquid after hydroformylation must undergo flash distillation and rectification to separate the catalytic system from the product and raw materials. Heat exposure to the catalyst system during this process also reduces the life of the catalyst. In summary, reactions involving current hydroformylation catalysts have the problem of difficult catalyst and ligand recovery, and the use of phosphine-containing ligands can pollute the natural environment. The selection of appropriate ligands and catalysts is crucial to the conversion rate of olefins and the production cost of the products.

[0016] To address the problems existing in the above-mentioned hydroformylation catalyst, the present invention uses cheap and readily available polystyrene as a reaction raw material, performs acetylation at the para position of the polystyrene through FC acylation, and generates a catalyst intermediate containing an acetyl group at the para position; then performs Baeyer-Villiger oxidation to obtain a catalyst intermediate containing an ester group at the para position; then performs a reduction reaction, and then reacts with a chlorophosphite to generate a phosphine-containing ligand, and finally reacts with a rhodium-containing compound to obtain a hydroformylation catalyst.

[0017] The catalyst prepared by the method solves the problem of difficulty in separating the reaction raw materials, products and catalyst during the hydroformylation process. The method can obtain the product with high yield and high selectivity under relatively mild conditions, while reducing the loss of the catalyst system. Moreover, the activity of the catalyst system can be maintained after multiple uses, thereby reducing production costs.

[0018] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S1, the temperature when adding aluminum chloride is 0-3°C; the present invention adds aluminum chloride to polystyrene at a low temperature in order to prevent an excessively violent reaction from causing cross-linking of the polystyrene.

[0019] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, the step S1 further includes an organic solvent, carbon disulfide.

[0020] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S1, the reaction temperature of the FC acylation reaction is 20-50° C., and the reaction time is 2-6 hours.

[0021] As a more preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, the reaction temperature of the FC acylation reaction is 25° C. and the reaction time is 3 h.

[0022] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, during the FC acylation reaction, acetyl chloride is added dropwise. The dropping speed of acetyl chloride should not be too fast, otherwise it will cause the temperature to rise too quickly and the reaction to fail.

[0023] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S1, the mass ratio of acetyl chloride to polystyrene is acetyl chloride:polystyrene=(1.1-2):1.

[0024] As a more preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, the mass ratio of acetyl chloride to polystyrene is acetyl chloride:polystyrene=1.75:1.

[0025] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S1, after the FC acylation reaction, the reaction mixture is added to a large amount of crushed ice for quenching, and then concentrated hydrochloric acid is added dropwise for acidification. The concentrated hydrochloric acid should not be added too quickly, otherwise liquid will spray out, causing a safety accident and also affecting the reaction yield. After the acidification is completed, the polymer is separated from the organic layer, diluted with an appropriate amount of dichloroethane, and excess methanol is added to precipitate a white precipitate. The precipitate is redissolved in a small amount of THF, reprecipitated in excess methanol, and dried under vacuum to obtain catalyst intermediate A.

[0026] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S2, the acid catalyst is acetic anhydride and the oxidant is hydrogen peroxide.

[0027] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S2, the Baeyer-Villiger oxidation reaction time is 4 days to 8 days.

[0028] As a more preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, the Baeyer-Villiger oxidation reaction time is 6 days.

[0029] It should be noted that, in the Baeyer-Villiger oxidation reaction of the present invention, acetic anhydride and 30% hydrogen peroxide solution need to be added every 12 hours.

[0030] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S2, after the Baeyer-Villiger oxidation reaction is completed, the organic layer is separated using a separatory funnel, and a precipitate is precipitated in a large amount of methanol. The precipitated polymer is filtered and dried under vacuum to obtain the catalyst intermediate B.

[0031] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S3, the reducing agent is hydrazine hydrate.

[0032] As a preferred embodiment of the preparation method of the hydroformylation catalyst of the present invention, in step S3, the temperature of the reduction reaction is 25°C-60°C, preferably 25°C ； The reaction time is 1d-3d, preferably 2 d .

[0033] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S4, the reaction temperature is 25° C.-50° C., preferably 25° C.; and the reaction time is 2 h-10 h, preferably 8 h.

[0034] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S4, the reaction is carried out in an organic solvent selected from cyclohexane, benzene, toluene, diethyl ether, tetrahydrofuran or chloroform.

[0035] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S5, the rhodium-containing compound includes at least one of rhodium acetate, rhodium trifluoroacetate, tetrakis(triphenylphosphine)chlororhodium, and dicarbonyl acetylacetonate rhodium.

[0036] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S5, the concentration of the rhodium-containing compound solution is 0.5 mol / L-2 mol / L, preferably 1 mol / L.

[0037] As a preferred embodiment of the method for preparing the hydroformylation catalyst of the present invention, in step S5, the immersion temperature is 20°C-80°C, preferably 50°C; the immersion time is 1h-6h, preferably 2h, and after the reaction is completed, the mixture is filtered and dried at 90°C for 24 hours to obtain the catalyst.

[0038] The present invention also provides application of the hydroformylation catalyst in olefin hydroformylation reaction.

[0039] As a preferred embodiment of the use of the hydroformylation catalyst of the present invention in an olefin hydroformylation reaction, the olefin hydroformylation reaction method comprises: adding olefin, CO, H2, and the hydroformylation catalyst into a high-pressure reactor and stirring to carry out a contact reaction; after the reaction, extracting a liquid product, treating it, and then conducting gas chromatography detection.

[0040] As a preferred embodiment of the application of the hydroformylation catalyst of the present invention in the hydroformylation reaction of olefins, the mass percentage of the hydroformylation catalyst in the olefin is 0.1%-10%.

[0041] As a more preferred embodiment of the use of the hydroformylation catalyst of the present invention in the hydroformylation reaction of olefins, the mass percentage of the hydroformylation catalyst in the olefin is 1%.

[0042] As a preferred embodiment of the application of the hydroformylation catalyst of the present invention in the olefin hydroformylation reaction, the reaction parameters of the olefin hydroformylation reaction are: reaction temperature is 50 ℃ -150℃, reaction time is 1h-24h, reaction pressure is 1MPa-10MPa.

[0043] As a more preferred embodiment of the use of the hydroformylation catalyst of the present invention in the olefin hydroformylation reaction, the reaction parameters of the olefin hydroformylation reaction are: reaction temperature of 100° C., reaction time of 12 h, and reaction pressure of 3 MPa.

[0044] As a preferred embodiment of the use of the hydroformylation catalyst of the present invention in the hydroformylation reaction of olefins, the olefin includes at least one of ethylene, propylene, butene, butadiene, pentene, cyclopentene, cyclopentadiene, hexene, cyclohexene, heptene, octene, cyclooctene, isooctene, nonene, and decene.

[0045] After the olefin hydroformylation reaction of the present invention is completed, the organic matter and the catalyst system can be separated by filtration, and the separated catalyst system can be continuously recycled.

[0046] Compared with the prior art, the present invention has the following beneficial effects:

[0047] The present invention uses cheap and readily available polystyrene as a reaction raw material and prepares a novel hydroformylation catalyst through five chemical reactions. The catalyst can be directly filtered after the reaction is completed, greatly reducing the cost and difficulty of separating the catalytic system. The catalyst prepared by the preparation method of the present invention solves the problem of difficulty in separating the reaction raw materials, products and catalysts during the hydroformylation process. Through the above method, the product can be obtained with high yield and high selectivity under relatively mild conditions, while reducing the loss of the catalytic system. In addition, the activity of the catalytic system can be maintained after multiple uses, thereby reducing production costs. DETAILED DESCRIPTION

[0048] To better illustrate the purpose, technical solutions and advantages of the present invention, the present invention will be further described below in conjunction with specific embodiments. Those skilled in the art should understand that the specific embodiments described herein are only used to explain the present invention and are not intended to limit the present invention.

[0049] Unless otherwise specified, the reaction methods used in the examples are conventional methods; the materials, reagents, etc. used are all commercially available unless otherwise specified.

[0050] Example 1

[0051] The preparation method of the hydroformylation catalyst described in this embodiment comprises the following steps:

[0052] S1. Take a 250mL double-necked round-bottom flask, add 5g polystyrene and 150mL carbon disulfide, introduce nitrogen to replace the gas of the reaction system, install a condenser tube on the round-bottom flask, and make the whole system ice bath and stir vigorously; Then add 14g aluminum chloride to the reaction solution, wait until the color of the solution in the flask turns orange-red, add 50mL carbon disulfide solution containing 6mL acetyl chloride dropwise, after the addition is complete, continue to react under ice bath for 10-30min, then warm to room temperature and continue to react for 2-5h, thereafter, add the reaction mixture to a large amount of crushed ice to quench, then add concentrated hydrochloric acid dropwise to acidify; Then separate the polymer from the organic layer, dilute with an appropriate amount of dichloroethane, add excess methanol to precipitate a white precipitate, which is a polymer. It is redissolved in a small amount of THF, precipitated again in excess methanol, and dried under vacuum to obtain 6.2-6.6g catalyst intermediate A;

[0053] S2. Take a 250 mL round-bottom flask, add 10 mL of acetic anhydride, 10 mL of 30% H2O2 solution, and 1-2 drops of concentrated H2SO4, then add 50 mL of chloroform solution containing 2 g of intermediate A described in step S1, reflux and stir for 4-8 days, and add 5-10 mL of Ac2O and 10 mL of H2O2 to the system every 12 hours. The total volume of Ac2O and H2O2 is 120 mL; then separate the organic layer with a separatory funnel, precipitate in a large amount of methanol, filter the precipitated polymer, and dry under vacuum to obtain 1.2-1.8 g of catalyst intermediate B;

[0054] S3, dissolving 250 mg of the intermediate B described in step S2 in 15 ml of 1,4-dioxane and 2 mL of pure water, adding 0.1-0.3 mL of hydrazine hydrate to the solution under ice bath, then raising the temperature to 25-60° C., the entire polymer material immediately aggregates and changes from colorless to dark blue, stirring continuously for 2-5 days, separating the product and drying it in an oven for 0.5-2 days to obtain 128-165 mg of catalyst intermediate C;

[0055] S4. Dissolve 100 mg of the intermediate C described in step S3 in 10 mL of acetonitrile and 10 mL of chloroform, replace the atmosphere with nitrogen three times, add 100 μL of diisopropylethylamine and 100 μL of diethyl chlorophosphite under a nitrogen atmosphere, and stir at 25-50°C for 2-10 hours. After the reaction is completed, add a large amount of methanol to precipitate, filter, and dry the polymer under vacuum to obtain 105-120 mg of catalyst intermediate D; characterized by P spectrum, 31 P NMR: 128 ppm;

[0056] S5. Take 100 mg of intermediate D and immerse it in 10 ml of toluene solution containing rhodium compound with a concentration of 0.5-2 mol / L. The immersion temperature is 25-50° C. and the immersion time is 2-5 hours. After the immersion is completed, wash with an appropriate amount (20-50 mL) of methanol and dry at 90° C. for 24 hours to obtain 112 mg of hydroformylation catalyst.

[0057] The elemental analysis of the hydroformylation catalyst described in this example is: C, 63.58; H, 5.86; O, 19.57; P, 8.82, Rh, 2.17. 31 P NMR: 135 ppm.

[0058] The preparation process of the hydroformylation catalyst described in this embodiment is shown below:

[0059]

[0060] Example 2

[0061] In this example, the hydroformylation catalyst prepared in Example 1 was used to carry out an olefin hydroformylation reaction. The specific steps were as follows: 20 g of isooctene was added to a 100 ml reactor, 200 mg of the hydroformylation catalyst described in Example 1 was added, the reactor was replaced three times with synthesis gas (H2:CO=1:1), the synthesis gas was introduced and the pressure was increased to 3 MPa, the temperature was increased to 100°C, and stirring was performed to initiate the reaction; during the reaction, synthesis gas was continuously introduced to maintain a stable pressure, the reaction was continued for 12 hours, and then analyzed by gas chromatography.

[0062] In this example, the conversion rate of isooctene was 94%, and the selectivity of isononanal was 95%.

[0063] Example 3

[0064] In this example, the product after the reaction in Example 2 was separated by filtration, and the obtained product was subjected to steps S2-S5 of Example 1, and the olefin hydroformylation reaction of Example 2 was repeated 5 times. The isooctene conversion rate and isononanal selectivity are shown in Table 1 below:

[0065] Table 1

[0066] Number of applications Conversion rate (%) Selectivity (%) first 93.6 95.2 Second time 94.0 94.6 The third time 93.8 94.3 Fourth time 91.2 95.2 Fifth 91.4 94.8

[0067] Example 4

[0068] The only difference between this example and example 2 is that in this example, the hydroformylation catalyst prepared in example 1 was used to perform an olefin hydroformylation reaction. The specific steps were as follows: 12.5 g of 1-pentene and 200 mg of the hydroformylation catalyst described in example 1 were added to a 100 ml reactor, the reactor was replaced three times with synthesis gas (H2:CO=1:1), the synthesis gas was introduced and the pressure was increased to 3 MPa, the temperature was increased to 100°C, and stirring was performed to initiate the reaction; during the reaction, synthesis gas was continuously introduced to maintain a stable pressure, the reaction was continued for 12 hours, and then analyzed by gas chromatography.

[0069] In this example, the conversion rate of 1-pentene was 97%, and the selectivity of hexanal was 96%.

[0070] Example 5

[0071] In this example, the product after the reaction of Example 4 was separated by filtration, and the obtained catalyst was used to repeat the olefin hydroformylation reaction of Example 4 for 5 times. The conversion rate of 1-pentene and the selectivity of hexanal are shown in Table 2 below:

[0072] Table 2

[0073] Number of applications Conversion rate (%) Selectivity (%) first 96.9 96.2 Second time 98.5 94.8 The third time 96.3 96.2 Fourth time 94.5 95.4 Fifth 95.7 94.8

[0074] Example 6

[0075] The only difference between this example and example 2 is that in this example, the hydroformylation catalyst prepared in example 1 was used to perform an olefin hydroformylation reaction. The specific steps were as follows: 15 g of 1-hexene and 200 mg of the hydroformylation catalyst described in example 1 were added to a 100 ml reactor. Synthesis gas (H2:CO = 1:1) was used to replace the reactor three times. Synthesis gas was introduced and the pressure was increased to 3 MPa. The temperature was raised to 100°C and stirred to initiate the reaction. Synthesis gas was continuously introduced during the reaction to maintain a stable pressure. The reaction was continued for 12 hours, and then analyzed by gas chromatography.

[0076] In this example, the conversion rate of 1-hexene was 97%, and the selectivity of heptanal was 98%.

[0077] Example 7

[0078] In this example, the product after the reaction in Example 6 was separated by filtration, and the obtained catalyst was used to repeat the olefin hydroformylation reaction of Example 6 five times. The conversion rate of 1-hexene and the selectivity of heptanal are shown in Table 3 below:

[0079] Table 3

[0080] Number of applications Conversion rate (%) Selectivity (%) first 97.2 97.9 Second time 95.8 96.4 The third time 93.5 95.8 Fourth time 94.2 96.1 Fifth 94.1 95.8

[0081] According to the results in Tables 1-3, the hydroformylation catalyst prepared by the present invention has high conversion rate and selectivity in the reaction of hydroformylating olefins to produce aldehydes; the product and the catalyst system can be directly separated by filtration, which reduces the loss of the catalyst system and significantly improves the economic efficiency of the hydroformylation reaction; and isononanal can be prepared with high selectivity and high yield, reducing production costs.

[0082] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit the scope of protection of the present invention. Although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art should understand that the technical solutions of the present invention may be modified or replaced by equivalents without departing from the essence and scope of the technical solutions of the present invention.

Claims

1. A method for preparing a hydroformylation catalyst, characterized in that: The method comprises the following steps: S1. Using polystyrene as a raw material, undergoing FC acylation reaction with aluminum chloride and acetyl chloride to generate the catalyst intermediate A described in formula (1); S2, subjecting the intermediate A described in step S1 to a Baeyer-Villiger oxidation reaction in an acid catalyst and an oxidant to generate the catalyst intermediate B described in formula (2); S3, subjecting the intermediate B described in step S2 to a reduction reaction with a reducing agent to generate the catalyst intermediate C described in formula (3); S4, reacting the intermediate C described in step S3 with a chlorophosphite in the presence of an organic base to produce a catalyst intermediate D described in formula (4); S5, immersing the catalyst intermediate D described in step S4 in a rhodium-containing compound solution, filtering and drying, to obtain a hydroformylation catalyst, wherein the chemical formula of the hydroformylation catalyst is Rh-(C 12 H 17 O3P) n ; The value of n is 100-1000.

2. The method for preparing a hydroformylation catalyst according to claim 1, wherein: In the step S1, the temperature when adding aluminum chloride is 0°C-3°C, the reaction temperature of the FC acylation reaction is 20°C-50°C, and the reaction time is 2h-6h.

3. The method for preparing a hydroformylation catalyst according to claim 1, wherein: In the step S1, the mass ratio of acetyl chloride to polystyrene is acetyl chloride:polystyrene=(1.1-2):

1.

4. The method for preparing a hydroformylation catalyst according to claim 1, wherein: In step S2, the acid catalyst is acetic anhydride, and the oxidant is hydrogen peroxide; and the Baeyer-Villiger oxidation reaction time is 4-8 days.

5. The method for preparing a hydroformylation catalyst according to claim 1, wherein: In step S3, the reducing agent is hydrazine hydrate; the temperature of the reduction reaction is 25° C.-60° C., and the time is 1 day-3 days.

6. The method for preparing a hydroformylation catalyst according to claim 1, wherein: In step S4, the reaction temperature is 25° C.-50° C., and the reaction time is 2 h-10 h.

7. The method for preparing a hydroformylation catalyst according to claim 1, wherein: In step S5, the rhodium-containing compound includes at least one of rhodium acetate, rhodium trifluoroacetate, tetrakis(triphenylphosphine)chlororhodium, and dicarbonyl acetylacetonate rhodium; the concentration of the rhodium-containing compound solution is 0.5 mol / L-2 mol / L; the immersion temperature is 20°C-80°C; and the immersion time is 1 hour-6 hours.

8. A hydroformylation catalyst, characterized in that The hydroformylation catalyst is prepared by the preparation method according to any one of claims 1 to 7.

9. Use of the hydroformylation catalyst according to claim 8 in olefin hydroformylation reaction.

10. Use of the hydroformylation catalyst according to claim 9 in olefin hydroformylation reaction, characterized in that: The olefin hydroformylation reaction method comprises: adding olefin, CO and H2, and the hydroformylation catalyst into a high-pressure reactor and stirring to carry out contact reaction; after the reaction is completed, extracting the liquid phase product, treating it, and then conducting gas chromatography detection; The olefins include at least one of ethylene, propylene, butene, butadiene, pentene, cyclopentene, cyclopentadiene, hexene, cyclohexene, heptene, octene, cyclooctene, isooctene, nonene, and decene; The mass percentage of the hydroformylation catalyst in the olefin is 0.1%-10%; The reaction parameters of the olefin hydroformylation reaction are: reaction temperature of 50° C.-150° C., reaction time of 1 h-24 h, and reaction pressure of 1 MPa-10 MPa.

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