A catalytic composition and its use in the synthesis of isononylaldehyde by hydroformylation

Abstract

This invention discloses a catalytic composition and its application in the hydroformylation reaction to synthesize isononanal, relating to the technical field of chemical engineering. The catalytic composition of this invention comprises an organic solvent, water, a water-soluble phosphine ligand, and a rhodium compound. The general formula of the water-soluble phosphine ligand is shown below: where Ar is an aryl group, R... 1 The catalyst is any one of hydrogen atom, straight-chain / branched alkyl, heteroalkyl, cycloalkyl, heterocyclic, heterocyclic alkyl, aryl, substituted aryl, or substituted aryl derivative groups; the volume ratio of organic solvent to water is 1:1-10; the molar concentration of rhodium in the catalytic composition is 0.002-0.1 mol / L; the molar ratio of rhodium to water-soluble phosphine ligand in the catalytic composition is 1:3-50. This invention uses this catalyst in a two-phase catalytic hydroformylation reaction of olefins to prepare isonononal, which can improve the conversion rate of olefins and the selectivity of isonononal.

Description

Technical Field

[0001] This invention relates to the field of chemical engineering, and more particularly to a catalytic composition and its application in the hydroformylation reaction to synthesize isononal. Background Technology

[0002] Isonononal, as an important organic chemical raw material, has a wide range of applications in plasticizers, surfactants, fragrances, detergents, and organic synthesis. Using isonononal as a raw material, it can be further processed into fine chemical products with higher application value. For example, isonononal can be converted into isononyl ester through hydrogenation and esterification, which is used as a plasticizer. In addition, isonononal can be oxidized to obtain isonononic acid, which is a very important application of isonononal. Highly branched isonononic acid, due to its unique structure, possesses excellent wettability, penetrability, and emulsifying properties, and has important applications in lubricants, industrial detergents, and other industries.

[0003] Currently, the development of isononanal production technology in China is still largely in the laboratory stage, and related hydroformylation process research mainly focuses on homogeneous catalytic compositions. For example, Zhang Runtong et al. used a rhodium compound as a catalyst metal precursor and an organophosphorus ligand as a catalyst ligand, and stirred it in a solvent to form a rhodium / organophosphorus ligand catalytic composition. Under the conditions of a syngas ratio of CO:H2 = 1:1, a reaction temperature between 80 and 140°C, a pressure between 1 and 8 MPa, and a reaction time between 4 and 20 hours, they prepared isononanal from diisobutylene, achieving a conversion rate of 77.8% and a yield of 93.8% (CN111909014A). Wang Pengfei et al. used two organophosphorus ligands as combined phosphorus ligands and a rhodium compound as a catalyst metal precursor to carry out the hydroformylation reaction of diisobutylene. The syngas ratio was CO:H2 = 1:1, the reaction time was 4.0 h, the temperature was 100 °C, and the reaction pressure was 1.0 MPa. The single-pass olefin conversion rate could reach more than 99%, and the aldehyde yield could reach more than 97% (CN112794796A).

[0004] As the examples above show, homogeneous catalytic hydroformylation of olefins mostly uses complexes of rhodium and triphenylphosphine and their derivatives as catalysts, which has advantages such as fast reaction rates. However, the separation of catalyst and product after the reaction is relatively difficult, requiring flash evaporation for separation. This method is suitable for reactions of olefins with fewer than 4 carbon atoms. For olefins with more carbon atoms, the aldehyde, the hydroformylation product, has a higher boiling point. Separating the catalyst and product using flash evaporation often requires higher temperatures, which can lead to the polymerization and deactivation of the rhodium-phosphine complex, as well as the polymerization and oxidation of the aldehyde.

[0005] To avoid the aforementioned problems, FR12478078 developed a two-phase catalytic hydroformylation method for aldehyde synthesis. Water is used as the solvent, and rhodium and a water-soluble phosphine ligand (e.g., tris(m-phenyl)sulfonate sodium) are used as catalysts. The starting olefin and the generated aldehyde are in the organic phase, while the rhodium-phosphine catalyst is in the water, and the two phases automatically separate. The advantage of this process is the easy separation of the product and the catalyst, but the hydroformylation rate is slow for olefins with more than C5 atoms. Therefore, developing suitable water-soluble phosphine ligands to promote the two-phase hydroformylation process of high-carbon olefins to prepare aldehydes is an objective requirement for this type of reaction and will undoubtedly have excellent application prospects in industrialization. Summary of the Invention

[0006] The purpose of this invention is to overcome the shortcomings of the prior art and provide a catalytic composition and its application in the hydroformylation reaction to synthesize isononanal. Using the catalytic composition of this invention in a two-phase catalytic olefin hydroformylation reaction to prepare isononanal can improve the olefin conversion rate and the selectivity of isononanal.

[0007] To achieve the above objectives, the technical solution adopted by the present invention is as follows:

[0008] In a first aspect, the present invention provides a catalytic composition comprising the following components: an organic solvent, water, a water-soluble phosphine ligand, and a rhodium compound, wherein the general formula of the water-soluble phosphine ligand is shown below:

[0009]

[0010] In the formula, Ar is an aryl group, and R... 1 It can be any one of hydrogen atom, straight-chain / branched alkyl, heteroalkyl, cycloalkyl, heterocyclic group, heterocyclic alkyl, aryl, substituted aryl, or substituted aryl derivative group;

[0011] The volume ratio of the organic solvent to water is 1:1-10;

[0012] The molar concentration of rhodium in the catalytic composition is 0.002-0.1 mol / L; the molar ratio of total rhodium to water-soluble phosphine ligand in the catalytic composition is 1:3-50.

[0013] The catalytic composition of this invention introduces hydrazine substituents on the arylbenzene ring of the water-soluble organophosphorus ligand, which effectively improves the water solubility of the phosphorus ligand. By changing the substituents on the nitrogen atom of the hydrazine, its water solubility can be adjusted, thereby increasing the rate of olefin conversion to isonononal to a certain extent. The catalytic efficiency is even higher when combined with rhodium compounds. At the same time, the addition of a mixed solvent of organic solvent and water in a specific ratio can improve the solubility of phosphorus ligand and rhodium compounds in water, so that phosphorus ligand and rhodium compounds can better form complexes, thereby improving the catalytic effect of the catalytic composition.

[0014] Preferably, the molar concentration of rhodium in the catalytic composition is 0.005-0.05 mol / L.

[0015] Preferably, the molar ratio of rhodium to water-soluble phosphine ligand in the catalytic composition is 1:5-20.

[0016] Preferably, the method for preparing the water-soluble phosphine ligand includes the following steps: reacting 4-diphenylphosphine benzoic acid with an alcohol to generate an ester compound, then exchanging the ester compound with hydrazine to obtain an acylhydrazine compound, and finally dehydrating and condensing the acylhydrazine compound with an aldehyde, followed by a reduction reaction to obtain the water-soluble phosphine ligand.

[0017] Preferably, the volume ratio of the organic solvent to water is 1:5.

[0018] Preferably, the organic solvent is one of alcohol, acetone, dimethyl sulfoxide, and dimethylformamide.

[0019] More preferably, the alcohol is one of methanol, ethanol, propanol, isopropanol, and butanol.

[0020] Preferably, in the general formula of the water-soluble phosphine ligand, Ar is one of a phenyl group, an alkyl group, or an alkoxy-substituted phenyl group.

[0021] Preferably, the rhodium compound is rhodium trichloride (RhCl3), rhodium acetate (III) (Rh(OAc)3), rhodium sulfate (Rh2(SO4)3), (1,5-cyclooctadiene)rhodium chloride dimer (Rh2(COD)2Cl2), rhodium acetate dimer (Rh2(OAc)4), rhodium nitrate (III) (Rh(NO3)3), or rhodium carbonyl (Rh6(CO)3). 16 Rh4(CO) 12 The following are some of the following: rhodium dicarbonyl acetylacetonate (Rh(acac)(CO)2), rhodium acetylacetonate (1,5-cyclooctadiene) (Rh(acac)(COD)), rhodium dicarbonyl chloride dimer (Rh2(CO)4Cl2), tris(m-triphenylphosphine trisulfonate sodium salt) chlorocarbonyl rhodium (RhCl(CO)(TPPTS)3), and tris(m-triphenylphosphine trisulfonate sodium salt) hydroxycarbonyl rhodium (HRh(CO)(TPPTS)3). In the above formulas, acac represents acetylacetonate, and TPPTS represents tris(m-phenyl)sulfonate sodium salt.

[0022] Secondly, the present invention also provides an application of the above-mentioned catalytic composition in the hydroformylation reaction to synthesize isononanal, comprising the following steps:

[0023] An olefin, an auxiliary agent, and a phase transfer catalyst are added to the catalytic composition, and synthesis gas is introduced. The mixture is heated to carry out a hydroformylation reaction. After the reaction is completed, the water and oil phases are separated to obtain isononal product.

[0024] Preferably, the reaction temperature is 25-250℃, the reaction time is 2-24h, and the reaction pressure is 0.1-20MPa.

[0025] More preferably, the reaction temperature is 50-150℃, the reaction pressure is 5-8MPa, and the reaction time is 5-12h.

[0026] Preferably, the additive is an alkaline substance.

[0027] More preferably, the auxiliary agent is at least one of inorganic carbonates, phosphates, main group metal salts of organic alcohols / phenols / carboxylic acids, main group metal amine compounds, and main group metal hydroxides.

[0028] More preferably, the additive is potassium carbonate.

[0029] Preferably, the phase transfer catalyst is a quaternary ammonium salt.

[0030] More preferably, the quaternary ammonium salt is at least one of benzyltriethylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium hydrogen sulfate, trioctylmethylammonium chloride, dodecyltrimethylammonium chloride, and tetradecyltrimethylammonium chloride.

[0031] Preferably, the molar concentration of the adjuvant is 0.001-0.1 mol / L, and the molar concentration of the quaternary ammonium salt is 0.01-0.1 mol / L.

[0032] More preferably, the molar concentration of the adjuvant is 0.002-0.05 mol / L, and the molar concentration of the quaternary ammonium salt is 0.05-0.1 mol / L.

[0033] Preferably, the molar ratio of the auxiliary agent to the quaternary ammonium salt is 1:2-25.

[0034] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0035] (1) The catalytic composition of the present invention is used in the two-phase catalytic hydroformylation reaction of olefins to prepare isononal, which can improve the conversion rate of olefins and the selectivity of isononal.

[0036] (2) In the catalytic composition of the present invention, the water-soluble organophosphine ligand is introduced with an acyl hydrazine substituent on the aryl benzene ring, which effectively improves the water solubility of the phosphine ligand. By changing the substituent on the nitrogen atom of the acyl hydrazine, its water solubility can be adjusted, thereby increasing the rate of olefin conversion to isononanal to a certain extent. The catalytic efficiency is higher when combined with rhodium compounds. At the same time, the addition of a specific ratio of organic solvent and water mixed solvent can improve the solubility of phosphine ligand and rhodium compounds in water, so that phosphine ligand and rhodium compounds can better form complexes, thereby improving the catalytic effect of the catalytic composition. Detailed Implementation

[0037] To better illustrate the purpose, technical solution, and advantages of the present invention, the present invention will be further described below in conjunction with specific embodiments, but the scope of protection and implementation of the present invention are not limited thereto.

[0038] Unless otherwise specified, the materials and reagents used in the following examples are commercially available.

[0039] Preparation Example

[0040] A method for preparing a water-soluble phosphine ligand includes the following steps:

[0041] (1) Add anhydrous ethanol and 4-diphenylphosphine benzoic acid (molar ratio of anhydrous ethanol and 4-diphenylphosphine benzoic acid is 2:1) to a 100 mL round bottom flask. Add thionyl chloride slowly dropwise using a constant pressure dropping funnel under ice-water bath conditions. After the reaction is completed, extract the organic phase and separate the ester intermediate. Dissolve the ester in ethanol and then slowly add hydrazine hydrate. React at room temperature for 1 h. After the reaction is completed, filter the crude product and wash it with diethyl ether to obtain a white solid product.

[0042] (2) The white solid was then dissolved in toluene, butyraldehyde was added and stirred at 50°C for 40 min. The reaction mixture was then cooled to room temperature to precipitate crystals. The mixture was filtered and washed with pre-cooled toluene and dried to obtain the corresponding acylhydrazone. Methanol was then added and stirred to dissolve the acylhydrazone. Glacial acetic acid was added dropwise, and sodium cyanoborohydride was added under ice-water bath conditions to reduce the target product, namely the water-soluble phosphine ligand.

[0043] The reaction process is shown in the following reaction equation:

[0044]

[0045] Example 1

[0046] A catalytic composition comprising 1 mmol of rhodium dicarbonylacetylacetone, 3 mmol of a water-soluble phosphine ligand, and 50 ml of a mixed solution of water and ethanol.

[0047] The catalytic composition is prepared by first preparing 50 mL of a mixed solution of ethanol and water with a volume ratio of 1:1, then adding 1 mmol of rhodium dicarbonyl acetylacetone and 3 mmol of water-soluble phosphine ligand, and mixing thoroughly to obtain the catalytic composition.

[0048] The application of a catalytic composition in the hydroformylation reaction to synthesize isononanal includes the following steps:

[0049] A 300 mL high-pressure reactor was used. After rinsing with N2, the prepared catalyst composition was added, and the mixture was stirred at room temperature for 1 h. Subsequently, 1 mmol of potassium carbonate, 0.5 mmol of tetrabutylammonium bromide, and 500 mmol of diisobutylene were added to replace the N2 and a vacuum was drawn. Carbon monoxide and hydrogen cylinders were connected, and the mixture was rapidly heated to 150 °C while adjusting the system pressure to 5.0 MPa. The stirring speed was maintained at 800 rpm for 12 h. After the reaction was completed, the reactor was rapidly cooled to room temperature, and the pressure was slowly released to atmospheric pressure. The reaction solution was then extracted, processed, and analyzed by gas chromatography.

[0050] In this embodiment, the molar concentration of rhodium in the catalytic composition is 0.02 mol / L; the molar ratio of total rhodium to water-soluble phosphine ligand in the catalytic composition is 1:3; and the volume ratio of ethanol to water is 1:1.

[0051] Example 2

[0052] A catalytic composition comprising 5 mmol of rhodium dicarbonylacetylacetone, 15 mmol of a water-soluble phosphine ligand, and 50 ml of a mixed solution of water and ethanol.

[0053] The catalytic composition is prepared by first preparing 50 mL of a mixed solution of ethanol and water with a volume ratio of ethanol to water of 1:20, then adding 5 mmol of rhodium dicarbonyl acetylacetone and 15 mmol of water-soluble phosphine ligand, and mixing thoroughly to obtain the catalytic composition.

[0054] The application of a catalytic composition in the hydroformylation reaction to synthesize isononanal includes the following steps:

[0055] A 300 mL high-pressure reactor was used. After rinsing with N2, the prepared catalyst composition was added, and the mixture was stirred at room temperature for 1 h. Subsequently, 1 mmol of potassium carbonate, 0.5 mmol of tetrabutylammonium bromide, and 500 mmol of diisobutylene were added to replace the N2 and a vacuum was drawn. Carbon monoxide and hydrogen cylinders were connected, and the mixture was rapidly heated to 150 °C while adjusting the system pressure to 5.0 MPa. The stirring speed was maintained at 800 rpm for 12 h. After the reaction was completed, the reactor was rapidly cooled to room temperature, and the pressure was slowly released to atmospheric pressure. The reaction solution was then extracted, processed, and analyzed by gas chromatography.

[0056] In this embodiment, the molar concentration of rhodium in the catalytic composition is 0.1 mol / L; the molar ratio of total rhodium to water-soluble phosphine ligand in the catalytic composition is 1:3; and the volume ratio of ethanol to water is 1:10.

[0057] Example 3

[0058] A catalytic composition comprising 2.5 mmol of rhodium dicarbonylacetylacetone, 12.5 mmol of a water-soluble phosphine ligand, and 50 ml of a mixed solution of water and ethanol.

[0059] The catalytic composition is prepared by first preparing 50 mL of a mixed solution of ethanol and water with a volume ratio of ethanol to water of 1:10, then adding 2.5 mmol of rhodium dicarbonyl acetylacetone and 12.5 mmol of water-soluble phosphine ligand, and mixing thoroughly to obtain the catalytic composition.

[0060] The application of a catalytic composition in the hydroformylation reaction to synthesize isononanal includes the following steps:

[0061] A 300 mL high-pressure reactor was used. After rinsing with N2, the prepared catalyst composition was added, and the mixture was stirred at room temperature for 1 h. Subsequently, 1 mmol of potassium carbonate, 0.5 mmol of tetrabutylammonium bromide, and 500 mmol of diisobutylene were added to replace the N2 and a vacuum was drawn. Carbon monoxide and hydrogen cylinders were connected, and the mixture was rapidly heated to 150 °C while adjusting the system pressure to 5.0 MPa. The stirring speed was maintained at 800 rpm for 12 h. After the reaction was completed, the reactor was rapidly cooled to room temperature, and the pressure was slowly released to atmospheric pressure. The reaction solution was then extracted, processed, and analyzed by gas chromatography.

[0062] In this embodiment, the molar concentration of rhodium in the catalytic composition is 0.05 mol / L; the molar ratio of total rhodium to water-soluble phosphine ligand in the catalytic composition is 1:5; and the volume ratio of ethanol to water is 1:10.

[0063] Example 4

[0064] A catalytic composition comprising 1 mmol of rhodium dicarbonylacetylacetone, 20 mmol of a water-soluble phosphine ligand, and 50 ml of a mixed solution of water and ethanol.

[0065] The catalytic composition is prepared by first preparing 50 mL of a mixed solution of ethanol and water with a volume ratio of ethanol to water of 1:10, then adding 1 mmol of rhodium dicarbonyl acetylacetone and 20 mmol of water-soluble phosphine ligand, and mixing thoroughly to obtain the catalytic composition.

[0066] The application of a catalytic composition in the hydroformylation reaction to synthesize isononanal includes the following steps:

[0067] A 300 mL high-pressure reactor was used. After rinsing with N2, the prepared catalyst composition was added, and the mixture was stirred at room temperature for 1 h. Subsequently, 1 mmol of potassium carbonate, 0.5 mmol of tetrabutylammonium bromide, and 500 mmol of diisobutylene were added to replace the N2 and a vacuum was drawn. Carbon monoxide and hydrogen cylinders were connected, and the mixture was rapidly heated to 150 °C while adjusting the system pressure to 5.0 MPa. The stirring speed was maintained at 800 rpm for 12 h. After the reaction was completed, the reactor was rapidly cooled to room temperature, and the pressure was slowly released to atmospheric pressure. The reaction solution was then extracted, processed, and analyzed by gas chromatography.

[0068] In this embodiment, the molar concentration of rhodium in the catalytic composition is 0.02 mol / L; the molar ratio of total rhodium to water-soluble phosphine ligand in the catalytic composition is 1:20; and the volume ratio of ethanol to water is 1:10.

[0069] Example 5

[0070] The difference from Example 4 is that the molar concentration of potassium carbonate is 0.002 mol / L and the molar concentration of tetrabutylammonium bromide is 0.05 mol / L, while the other steps are the same as in Example 4.

[0071] Example 6

[0072] The difference from Example 4 is that the molar concentration of potassium carbonate is 0.05 mol / L and the molar concentration of tetrabutylammonium bromide is 0.1 mol / L, while the other steps are the same as in Example 4.

[0073] Example 7

[0074] The difference from Example 4 is that the molar concentration of potassium carbonate is 0.3 mol / L and the molar concentration of tetrabutylammonium bromide is 0.2 mol / L, while the other steps are the same as in Example 4.

[0075] Example 8

[0076] The difference from Example 4 is that the molar concentration of potassium carbonate is 0.02 mol / L and the molar concentration of tetrabutylammonium bromide is 0.005 mol / L, while the other steps are the same as in Example 4.

[0077] Comparative Example 1

[0078] The difference from Example 1 is that the molar concentration of rhodium in the catalytic composition is 0.001 mol / L, while the other steps are the same as in Example 1.

[0079] Comparative Example 2

[0080] The difference from Example 1 is that the molar ratio of rhodium to water-soluble phosphine ligand in the catalytic composition is 1:2, while the other steps are the same as in Example 1.

[0081] Comparative Example 3

[0082] The difference from Example 1 is that the molar ratio of rhodium to water-soluble phosphine ligand in the catalytic composition is 1:1, while the other steps are the same as in Example 1.

[0083] Comparative Example 4

[0084] The difference from Example 1 is that the water-soluble phosphine ligand is tris(sodium phenyl sulfonate), while the other steps are the same as in Example 1.

[0085] Comparative Example 5

[0086] The difference from Example 1 is that the volume ratio of ethanol to water is 3:2, while the other steps are the same as in Example 1.

[0087] Comparative Example 6

[0088] The difference from Example 1 is that the volume ratio of ethanol to water is 1:20, while the other steps are the same as in Example 1.

[0089] The experimental results of the above embodiments and comparative examples are shown in Table 1.

[0090] Table 1

[0091]

[0092] As shown in Table 1, the present invention introduces hydrazide substituents on the arylbenzene ring of the phosphine ligand, which effectively improves the catalytic effect of the catalyst, thereby increasing the rate of diisooctene to isononanal to a certain extent. Furthermore, the two-phase catalysis facilitates the separation of the catalyst and the product, the catalyst can be recycled, the operation process is simplified, and it has broad application prospects.

[0093] The catalytic composition prepared in this invention can be used in the hydroformylation reaction of diisobutylene to prepare isononal, which can promote the conversion of diisobutylene to isononal and improve the selectivity of isononal.

[0094] 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 modifications or equivalent substitutions can be made to the technical solutions of the present invention without departing from the essence and scope of the technical solutions of the present invention.

Claims

1. A catalytic composition, characterized in that, The catalytic composition comprises the following components: an organic solvent, water, a water-soluble phosphine ligand, and a rhodium compound, wherein the general formula of the water-soluble phosphine ligand is shown below: ； In the formula, Ar is an aryl group, and R... 1 It can be any one of hydrogen atom, straight-chain / branched alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, and aryl; The volume ratio of the organic solvent to water is 1:1-10; The molar concentration of rhodium in the catalytic composition is 0.002-0.1 mol / L; the molar ratio of rhodium to water-soluble phosphine ligand in the catalytic composition is 1:3-50.

2. The catalytic composition according to claim 1, characterized in that, The molar concentration of rhodium in the catalytic composition is 0.005-0.05 mol / L.

3. The catalytic composition according to claim 2, characterized in that, The molar ratio of rhodium to water-soluble phosphine ligand in the catalytic composition is 1:5-20.

4. The catalytic composition according to claim 1, characterized in that, The method for preparing the water-soluble phosphine ligand includes the following steps: reacting 4-diphenylphosphine benzoic acid with an alcohol to generate an ester compound, then exchanging the ester compound with hydrazine to obtain an acylhydrazine compound, and finally dehydrating and condensing the acylhydrazine compound with an aldehyde, followed by a reduction reaction to obtain the water-soluble phosphine ligand.

5. The catalytic composition according to claim 1, characterized in that, The organic solvent is one of alcohol, acetone, dimethyl sulfoxide, and dimethylformamide.

6. The catalytic composition according to claim 1, characterized in that, The rhodium compound is one of rhodium trichloride, rhodium sulfate, (1,5-cyclooctadiene) rhodium chloride dimer, rhodium acetate dimer, rhodium nitrate, dicarbonyl acetylacetone rhodium, acetylacetone (1,5-cyclooctadiene) rhodium, dicarbonyl chloride rhodium dimer, tris(m-triphenylphosphine trisulfonate sodium salt) chlorocarbonyl rhodium, and tris(m-triphenylphosphine trisulfonate sodium salt) hydroxycarbonyl rhodium.

7. The application of the catalytic composition according to any one of claims 1-6 in the hydroformylation reaction to synthesize isononanal, characterized in that, Includes the following steps: An olefin, an auxiliary agent, and a phase transfer catalyst are added to the catalytic composition, and synthesis gas is introduced. The mixture is heated to carry out a hydroformylation reaction. After the reaction is completed, the water and oil phases are separated to obtain isononal product.

8. The application of the catalytic composition as described in claim 7 in the hydroformylation reaction to synthesize isononanal, characterized in that, The auxiliary agent is at least one of inorganic carbonates, phosphates, main group metal salts of organic alcohols / phenols / carboxylic acids, main group metal amine compounds, and main group metal hydroxides.

9. The application of the catalytic composition as described in claim 7 in the hydroformylation reaction to synthesize isononal, characterized in that, The phase transfer catalyst is a quaternary ammonium salt.

10. The application of the catalytic composition as described in claim 9 in the hydroformylation reaction to synthesize isononal, characterized in that, The molar concentration of the adjuvant is 0.002-0.05 mol / L, and the molar concentration of the quaternary ammonium salt is 0.05-0.1 mol / L.

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