Bimetal catalyst coordinated by asymmetric bidentate phosphine ligand as well as preparation method and application of bimetallic catalyst

Abstract

The invention provides an asymmetric bidentate phosphine ligand coordinated bimetallic catalyst as well as a preparation method and application thereof, and the structure of the bimetallic catalyst is as shown in a formula (1): # imgabs0 # in the formula (1), r1, R2, R3 and R4 are independently any one of alkyl, hetero-alkyl, cycloalkyl, hetero-cycloalkyl, aryl, substituted aryl, hetero-aryl, substituted hetero-aryl, aryloxy, hetero-aryloxy, arylalkyl and hetero-arylalkyl; and R5 is any one of hydrogen, alkyl, hetero-alkyl, cycloalkyl, hetero-cycloalkyl, aryl, substituted aryl, hetero-aryl, substituted hetero-aryl, aryloxy, hetero-aryloxy, arylalkyl and hetero-arylalkyl. The bimetallic catalyst disclosed by the invention can catalyze isooctene, carbon monoxide and hydrogen to react to generate isononanal, the conversion rate of isooctene is as high as 98.5%, and the generation selectivity of isononanal is as high as 99%.

Description

Technical Field

[0001] The invention relates to the technical field of catalysts, and in particular to a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and a preparation method and application thereof. Background Art

[0002] Isononanal is an important organic chemical raw material, widely used in plasticizers, surfactants, fragrances, detergents and organic synthesis industries. From isononanal, many fine chemical products with high added value can be synthesized, especially isononanoic acid can be obtained by oxidation. Due to the unique properties of high-branched isononanoic acid such as excellent wettability, permeability and emulsification, it has important uses in lubricants, industrial detergents and other industries.

[0003] At present, the industrial production technology of isononanal at home and abroad is still imperfect and the reaction conditions are harsh. Tsinghua University, China University of Petroleum and Wanhua Chemical have reported related hydroformylation processes. Current research mainly focuses on homogeneous catalytic systems, water / oil two-phase catalytic systems, and multiphase solid-supported catalytic systems.

[0004] Ma Zhanhua et al. prepared a supported rhodium-based catalyst using activated carbon-supported metal Rh, and studied the hydroformylation reaction of mixed octenes (70% 2,4,4-trimethyl-1-pentene and 20% 2,4,4-trimethyl-2-pentene and other octenes isomers). Under the conditions of rhodium loading of 0.90wt%, reaction time of 5.0h, temperature of 107°C, and initial pressure of 5.0MPa, the conversion rate of mixed octenes can reach 63.6%, and the aldehyde yield is 48.5% (Fuel Processing Technology, 2009, 90, 1241-1246). Liu Zhenfeng et al. used nitrogen-containing heterocyclic phosphine ligands and metal cobalt and rhodium as catalysts to prepare methyl isononanoate by hydromethylation of isooctene, methanol and CO, and further hydrolyzed to obtain isononanoic acid. Under the conditions of rhodium content of 0.01wt% (relative to isooctene), reaction time of 6.0h, temperature of 100°C and reaction pressure of 12.0MPa, the isooctene conversion rate can reach 95.6% and the ester yield is 90.9% (CN 110605145).

[0005] Abroad, Mitsubishi Chemical of Japan has developed a hydroformylation reaction of isooctene using rhodium as a catalyst, using triphenylphosphine oxide and a rhodium complex with initial activity (Rh-TPPO) as catalysts to react at 20MPa and 130°C, with an isononanal yield of 95% (Ungvary F. Coord. Chem. Rev., 1997, 167: 233-260.). M. Glass et al. used an unmodified rhodium nonanoate catalyst, 2,4,4-trimethyl-1-pentene as a substrate, and reacted at a synthesis gas pressure of 27MPa, a temperature of 135°C, and a Rh concentration of 20ppm (based on isooctene). The isooctene conversion rate was 99.9%, and the reaction product contained 93.5wt% 3,5,5-trimethylhexanal, 2.5wt% 3,5,5-trimethylhexanol, 3.4wt% residual C8 hydrocarbons, and 0.6wt% heavy components (WO2006 / 136471). A. et al. used rhodium nonanoate as a catalyst precursor and a phosphite mixture as a ligand in a reaction system. Under the conditions of a pressure of 2 MPa, a reaction temperature of 140°C, a reaction time of 8 h, and a Rh concentration of 200 ppm, the isooctene conversion rate was 93%, the isononanal yield was 66.1%, and the normal-to-iso ratio was 0.71 (EP1099678).

[0006] At present, the common ligands in the olefin hydroformylation catalytic system are mainly phosphanes (phosphines), hypophosphites and phosphites, but the traditional phosphine compounds have poor hydroformylation reaction activity and selectivity when used as ligands due to the influence of electronic and steric effects. US20120253080 also found that when a mixture of monophosphite and diphosphite ligands is used as a ligand, the catalytic activity in the hydroformylation of long-chain olefins is very poor. In addition, the preparation process is usually complicated and costly (Journal of Catalysis, 2013, 298, 198-205).

[0007] In summary, the prior art has the problems of low conversion rate and product selectivity of isooctene hydroformylation and high catalyst production cost. Selecting suitable ligands and catalysts and controlling corresponding reaction conditions are crucial to the conversion rate of isooctene and the selectivity of isononanal. Summary of the invention

[0008] The purpose of the present invention is to overcome the shortcomings of the prior art and provide a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand and a preparation method and application thereof. The bimetallic catalyst can catalyze the reaction of isooctene, carbon monoxide and hydrogen to produce isononanal, with the conversion rate of isooctene reaching 98.5% and the selectivity of isononanal reaching 99%.

[0009] To achieve the above object, the technical solution adopted by the present disclosure is: a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, the structure of the bimetallic catalyst is shown in formula (1):

[0010]

[0011] In formula (1), R1, R2, R3, and R4 are each independently any one of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl;

[0012] R5 is any one of hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl.

[0013] Optionally, R1, R2, R3, and R4 are each independently any one of C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 substituted aryl, C6-C30 heteroaryl, C6-C30 substituted heteroaryl, C6-C30 aryloxy, C6-C30 heteroaryloxy, C6-C30 arylalkyl, and C6-C30 heteroarylalkyl.

[0014] Optionally, R5 is any one of H, C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 substituted aryl, C6-C30 heteroaryl, C6-C30 substituted heteroaryl, C6-C30 aryloxy, C6-C30 heteroaryloxy, C6-C30 arylalkyl, and C6-C30 heteroarylalkyl.

[0015] Optionally, R1, R2, R3, and R4 are each independently methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopentyl, cyclohexyl, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 2,6-diisopropylphenyl, 2,6-di-tert-butylphenyl, 2,4,6-trimethylphenyl, 2,4,6-triisopropylphenyl, 2,4,6-tri-tert-butylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, and thienyl.

[0016] Optionally, R5 is any one of H, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopentyl, cyclohexyl, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 2,6-diisopropylphenyl, 2,6-di-tert-butylphenyl, 2,4,6-trimethylphenyl, 2,4,6-triisopropylphenyl, and 2,4,6-tri-tert-butylphenyl.

[0017] On the other hand, a method for preparing the bimetallic catalyst is provided, comprising the following steps: reacting an asymmetric bidentate phosphine ligand, a carbonyl rhodium compound and a carbonyl ruthenium compound in an organic solvent to obtain a bimetallic catalyst, wherein the structural formula of the asymmetric bidentate phosphine ligand is R1R2PC6H4NR5PR3R4, and R1, R2, R3, and R4 are each independently any one of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl; and R5 is any one of hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl.

[0018] In another aspect, provided is the use of the bimetallic catalyst in the preparation of isononanal.

[0019] Optionally, the method comprises the following steps: reacting isooctene, carbon monoxide, hydrogen, a solvent and the bimetallic catalyst at 0-250° C. and 0.1-20 MPa for 0.01-100 h to obtain isononanal, wherein the concentration of the bimetallic catalyst is 0.001-100 mmol / L.

[0020] Optionally, the reaction temperature is 50-150° C., the pressure is 0.1-5 MPa, and the time is 1-10 h; and / or the concentration of the bimetallic catalyst is 0.5-20 mmol / L.

[0021] Optionally, the organic solvent is at least one of an organic alcohol, a phenol, an ether, and an aromatic solvent. Preferably, the organic solvent is at least one of methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, cyclopentanol, cyclohexanol, benzyl alcohol, phenol, benzene, toluene, ether, and tetrahydrofuran.

[0022] Compared with the prior art, the beneficial effects of the present invention are as follows: the bimetallic catalyst coordinated by the asymmetric bidentate phosphine ligand of the present invention can catalyze the reaction of isooctene, carbon monoxide and hydrogen to produce isononanal, the conversion rate of isooctene is as high as 98.5%, and the selectivity of isononanal production is as high as 99%. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 This is the H NMR spectrum of the bimetallic catalyst obtained in Example 1;

[0024] Figure 2 This is a graph showing the chromatographic analysis results of the reaction product obtained in Example 1. DETAILED DESCRIPTION

[0025] In order to make the technical problems, technical solutions and beneficial effects to be solved by the present application more clearly understood, the present application is further described in detail in the following embodiments. It should be understood that the specific embodiments described herein are only used to explain the present application and are not used to limit the present application.

[0026] The compounds and their derivatives involved in the examples of the present application are named according to the IUPAC (International Union of Pure and Applied Chemistry) or CAS (Chemical Abstracts Service, located in Columbus, Ohio) naming system. Therefore, the compound groups specifically involved in the examples of the present application are described and explained as follows:

[0027] With respect to "hydrocarbon groups", the minimum and maximum carbon atom content of the hydrocarbon group is indicated by a prefix, for example, the prefix (C-C) alkyl represents any alkyl group containing from "a" to "b" carbon atoms. Thus, for example, (C1-C6) alkyl refers to an alkyl group containing from one to six carbon atoms.

[0028] "Alkoxy" refers to a straight or branched, monovalent, saturated aliphatic chain bonded to an oxygen atom, including but not limited to methoxy, ethoxy, propoxy, butoxy, isobutoxy, tert-butoxy and other similar groups. (Ca-Cb) alkoxy refers to any straight or branched, monovalent, saturated aliphatic chain bonded to an oxygen atom in an alkyl group containing "a" to "b" carbon atoms.

[0029] "Alkyl" refers to a straight or branched, monovalent, saturated aliphatic chain, including but not limited to methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl and other similar groups.

[0030] "Heteroalkyl" refers to a linear or branched, monovalent, saturated aliphatic chain attached to at least one heteroatom, such as, but not limited to, methylaminoethyl or other similar groups.

[0031] "Aryl" refers to a cyclic aromatic hydrocarbon, including but not limited to phenyl, naphthyl, anthracenyl, phenanthrenyl and other similar groups.

[0032] "Heteroaryl" refers to a monocyclic or polycyclic or condensed aromatic hydrocarbon in which one or more carbon atoms have been replaced by heteroatoms such as nitrogen, oxygen or sulfur. If the heteroaryl contains more than one heteroatom, these heteroatoms may be the same or different. Heteroaryl groups include, but are not limited to, benzofuranyl, benzothiophenyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzopyranyl, furanyl, imidazolyl, indazolyl, indolizinyl, indolyl, isobenzofuranyl, isoindolyl, isoquinolyl, isothiazolyl, isoxazolyl, naphthyridinyl, oxadiazolyl, oxazinyl, oxazolyl, phthalazinyl, pteridinyl, purinyl, pyranyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridin[3,4-b]indolyl, pyridyl, pyrimidinyl, pyrrolyl, quinolizinyl, quinolyl, quinoxalinyl, thiadiazolyl, thiatriazolyl, thiazolyl, thienyl, triazinyl, triazolyl, xanthenyl and other similar groups.

[0033] "Cycloalkyl" refers to a saturated monocyclic or polycyclic alkyl group, which may be fused with an aromatic hydrocarbon group. Cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, indanyl, tetrahydronaphthyl and other similar groups.

[0034] "Heterocycloalkyl" refers to a saturated monocyclic or polycyclic alkyl group, which may be fused to an aromatic hydrocarbon group, in which at least one carbon atom has been replaced by a heteroatom such as nitrogen, oxygen or sulfur. If the heterocycloalkyl group contains more than one heteroatom, these heteroatoms may be the same or different. Heterocycloalkyl includes, but is not limited to, azepanyl, azetidinyl, dihydroindole, morpholinyl, piperazinyl, piperidinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydroquinolinyl, tetrahydroindazolyl, tetrahydroindolyl, tetrahydroisoquinolinyl, tetrahydropyranyl, tetrahydroquinoxalinyl, tetrahydrothiopyranyl, thiazolidinyl, thiomorpholinyl, thioxanthenyl, thioxanthyl and other similar groups.

[0035] The present disclosure provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, the structure of the bimetallic catalyst is shown in formula (1):

[0036]

[0037] In formula (1), R1, R2, R3, and R4 are each independently any one of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl;

[0038] R5 is any one of hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl.

[0039] The bimetallic catalyst provided by the present disclosure can be used as a catalyst for preparing isononanal by hydroformylation of isooctene, thereby improving the conversion rate of isooctene and the selectivity of isononanal.

[0040] Optionally, R1, R2, R3, and R4 are each independently any one of C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 substituted aryl, C6-C30 heteroaryl, C6-C30 substituted heteroaryl, C6-C30 aryloxy, C6-C30 heteroaryloxy, C6-C30 arylalkyl, and C6-C30 heteroarylalkyl.

[0041] When R1, R2, R3, and R4 are each independently a C1-C20 alkyl group, the C1-C20 alkyl group may be a (C1-C10)alkyl group, a (C1-C5)alkyl group, a (C1-C4)alkyl group, a (C1-C3)alkyl group, or a (C1-C2)alkyl group, etc.

[0042] When R1, R2, R3, and R4 are each independently a C1-C20 heteroalkyl group, the (C1-C20) heteroalkyl group may be a (C1-C10) heteroalkyl group, a (C1-C5) heteroalkyl group, a (C1-C4) heteroalkyl group, a (C1-C3) heteroalkyl group, or a (C1-C2) heteroalkyl group, etc.

[0043] When R1, R2, R3, and R4 are each independently a C3-C20 cycloalkyl group, the (C3-C20)cycloalkyl group may be a (C3-C10)cycloalkyl group, a (C3-C5)cycloalkyl group, or a (C3-C4)cycloalkyl group, etc.

[0044] When R1, R2, R3, and R4 are each independently (C3-C20)heterocycloalkyl, the (C3-C20)heterocycloalkyl may be (C3-C10)heterocycloalkyl, (C3-C10)heterocycloalkyl, (C3-C5)heterocycloalkyl, or (C3-C4)heterocycloalkyl, etc. In one embodiment, the heteroatom in the heterocycloalkyl may be a halogen, a nitrogen atom, etc.

[0045] Optionally, R5 is any one of H, C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 substituted aryl, C6-C30 heteroaryl, C6-C30 substituted heteroaryl, C6-C30 aryloxy, C6-C30 heteroaryloxy, C6-C30 arylalkyl, and C6-C30 heteroarylalkyl.

[0046] When R5 is a C1-C20 alkyl group, the C1-C20 alkyl group may be a (C1-C10) alkyl group, a (C1-C5) alkyl group, a (C1-C4) alkyl group, a (C1-C3) alkyl group or a (C1-C2) alkyl group, or the like.

[0047] When R5 is a C1-C20 heteroalkyl group, the (C1-C20) heteroalkyl group may be a (C1-C10) heteroalkyl group, a (C1-C5) heteroalkyl group, a (C1-C4) heteroalkyl group, a (C1-C3) heteroalkyl group or a (C1-C2) heteroalkyl group, etc.

[0048] When R5 is a C3-C20 cycloalkyl group, the (C3-C20)cycloalkyl group may be a (C3-C10)cycloalkyl group, a (C3-C5)cycloalkyl group or a (C3-C4)cycloalkyl group, or the like.

[0049] When R5 is (C3-C20)heterocycloalkyl, the (C3-C20)heterocycloalkyl may be (C3-C10)heterocycloalkyl, (C3-C10)heterocycloalkyl, (C3-C5)heterocycloalkyl or (C3-C4)heterocycloalkyl, etc. In one embodiment, the heteroatom in the heterocycloalkyl may be a halogen, a nitrogen atom, etc.

[0050] Optionally, R1, R2, R3, and R4 are each independently methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopentyl, cyclohexyl, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 2,6-diisopropylphenyl, 2,6-di-tert-butylphenyl, 2,4,6-trimethylphenyl, 2,4,6-triisopropylphenyl, 2,4,6-tri-tert-butylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, and thienyl.

[0051] Optionally, R5 is any one of H, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopentyl, cyclohexyl, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 2,6-diisopropylphenyl, 2,6-di-tert-butylphenyl, 2,4,6-trimethylphenyl, 2,4,6-triisopropylphenyl, and 2,4,6-tri-tert-butylphenyl.

[0052] On the other hand, a method for preparing the bimetallic catalyst is provided, comprising the following steps: reacting an asymmetric bidentate phosphine ligand, a carbonyl rhodium compound and a carbonyl ruthenium compound in an organic solvent to obtain a bimetallic catalyst, wherein the structural formula of the asymmetric bidentate phosphine ligand is R1R2PC6H4NR5PR3R4, and R1, R2, R3, and R4 are each independently any one of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl; and R5 is any one of hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl.

[0053] Optionally, R1, R2, R3, and R4 are each independently any one of C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 substituted aryl, C6-C30 heteroaryl, C6-C30 substituted heteroaryl, C6-C30 aryloxy, C6-C30 heteroaryloxy, C6-C30 arylalkyl, and C6-C30 heteroarylalkyl.

[0054] Optionally, R5 is any one of H, C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 substituted aryl, C6-C30 heteroaryl, C6-C30 substituted heteroaryl, C6-C30 aryloxy, C6-C30 heteroaryloxy, C6-C30 arylalkyl, and C6-C30 heteroarylalkyl.

[0055] In another aspect, provided is the use of the bimetallic catalyst in the preparation of isononanal.

[0056] Optionally, the method comprises the following steps: reacting isooctene, carbon monoxide, hydrogen, a solvent and the bimetallic catalyst at 0-250° C. and 0.1-20 MPa for 0.01-100 h to obtain isononanal, wherein the concentration of the bimetallic catalyst is 0.001-100 mmol / L.

[0057] The bimetallic catalyst of the present invention is used to contact and react with isooctene, carbon monoxide and hydrogen in an organic solvent under the above reaction conditions to improve the conversion rate of isooctene and the selectivity of isononanal.

[0058] Optionally, the reaction temperature is 50-150°C, the pressure is 0.1-5 MPa, and the time is 1-10 h; and / or the concentration of the bimetallic catalyst is 0.5-20 mmol / L. The inventors found that within the above preferred range, the conversion rate of isooctene and the selectivity of isononanal are higher.

[0059] Optionally, the reaction temperature can be 0°C, 30°C, 50°C, 70°C, 100°C, 120°C, 150°C, 180°C, 200°C, 220°C, 250°C, but the present application is not limited thereto; preferably, it is 50-150°C.

[0060] Optionally, the reaction pressure may be 0.1 MPa, 1 MPa, 2 MPa, 4 MPa, 7 MPa, 10 MPa, 12 MPa, 15 MPa, 17 MPa, or 20 MPa, but the present application is not limited thereto; preferably, it is 0.1-5 MPa.

[0061] Optionally, the reaction time can be 0.01h, 0.5h, 1h, 5h, 7h, 10h, 15h, 20h, 25h, 30h, 35h, 40h, 50h, 60h, 70h, 80h, 90h, 100h, and the present application is not limited thereto; preferably, it is 5-10h.

[0062] Optionally, the flow rate of the carbon monoxide and hydrogen is 300 mL / min to 800 mL / min; for example, it can be 300 mL / min, 400 mL / min, 500 mL / min, 600 mL / min, 700 mL / min, 800 mL / min, but the present application is not limited thereto.

[0063] Optionally, the volume ratio of carbon monoxide to hydrogen is (1-1.2):1; for example, it can be: 1:1, 1:1.1, 1.2:1, and the present application is not limited thereto.

[0064] Optionally, the addition ratio of the isooctene and the organic solvent is (50-200) mmol: (40-100) mL; for example, it can be 50mmol:40mL, 100mmol:40mL, 150mmol:40mL, 200mmol:40mL, 50mmol:60mL, 50mmol:80mL, 50mmol:100mL, and the present application is not limited thereto.

[0065] Optionally, the organic solvent is at least one of an organic alcohol, a phenol, an ether, and an aromatic solvent. Preferably, the organic solvent is at least one of methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, cyclopentanol, cyclohexanol, benzyl alcohol, phenol, benzene, toluene, ether, and tetrahydrofuran.

[0066] The bimetallic catalyst coordinated by the asymmetric bidentate phosphine ligand can catalyze the reaction of isooctene, carbon monoxide and hydrogen to generate isononanal, the conversion rate of isooctene is as high as 98.5%, and the selectivity of isononanal generation is as high as 99%.

[0067] The following is illustrated by multiple embodiments.

[0068] The following abbreviations are used in the examples of the present disclosure: Bu represents butyl, tBu represents tert-butyl, Pr represents propyl, iPr represents isopropyl, and Ph represents phenyl.

[0069] The gas chromatograph used in the present disclosure is Clarus 680 produced by PerkinElmer.

[0070] The asymmetric bisphosphine ligand, carbonyl ruthenium compound and carbonyl rhodium compound disclosed in the present invention are all purchased from Beijing Bailingwei Technology Co., Ltd.

[0071] Example 1

[0072] This embodiment provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and the preparation method thereof is as follows:

[0073] Equimolar amounts of asymmetric bisphosphine ligand PPh2C6H4N(H)PPh2, carbonyl rhodium compound Rh2Cl2(CO)4 and carbonyl ruthenium compound Ru3(CO)4 were added. 12 , placed in a Schlenk bottle, added toluene, stirred at room temperature for 12 hours, after the reaction, the solvent was removed under reduced pressure to obtain an asymmetric bidentate phosphine ligand coordinated bimetallic catalyst [PPh2C6H4N(H)PPh2]Rh(CO)2[PPh2C6H4N(H)PPh2]Ru(CO)2, whose structure is shown in formula (2) and its H NMR spectrum is shown in Figure 1 As shown;

[0074]

[0075] This embodiment also provides a method for preparing isononanal, comprising the following steps:

[0076] A 300mL high-pressure reactor was selected, and after N2 flushing, 1mmol of the bimetallic catalyst of the present embodiment, 100mmol of isooctene, and 40mL of toluene were added in sequence, the injection valve was closed, the synthesis gas cylinder was connected, and the reaction was heated to 80°C. Under the conditions of a pressure of 1.0MPa and a stirring rate of 800rpm, the reaction was carried out for 4 hours; wherein the synthesis gas was carbon monoxide and H2, and the volume ratio of carbon monoxide to H2 was 1:1; the flow rate of the synthesis gas was 500mL / min; after the reaction was completed, the reactor was cooled to 0°C, the pressure was released to normal pressure, and the reaction product was extracted for gas chromatography analysis. The analysis results are shown in Tables 1 and Figure 2 shown.

[0077] Example 2

[0078] This embodiment provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and the preparation method thereof is as follows:

[0079] Equimolar amounts of asymmetric bisphosphine ligand PPh2C6H4N(iPr)PPh2, carbonyl rhodium compound Rh2Cl2(CO)4 and carbonyl ruthenium compound Ru3(CO)4 were added. 12 , placed in a Schlenk bottle, added toluene, stirred at room temperature for 12 hours, after the reaction, the solvent was removed under reduced pressure to obtain an asymmetric bidentate phosphine ligand coordinated bimetallic catalyst [PPh2C6H4N(iPr)PPh2]Rh(CO)2[PPh2C6H4N(iPr)PPh2]Ru(CO)2.

[0080] This embodiment also provides a method for preparing isononanal, comprising the following steps:

[0081] A 300mL high-pressure reactor was selected, and after flushing with N2, 1mmol of the bimetallic catalyst of this embodiment, 100mmol of isooctene, and 40mL of toluene were added in sequence, the injection valve was closed, the synthesis gas cylinder was connected, and the reaction was heated to 80°C. Under the conditions of a pressure of 1.0MPa and a stirring rate of 800rpm, the reaction was carried out for 4 hours; wherein the synthesis gas was carbon monoxide and H2, and the volume ratio of carbon monoxide to H2 was 1:1; the flow rate of the synthesis gas was 500mL / min; after the reaction was completed, the reactor was cooled to 0°C, the pressure was released to normal pressure, and the reaction product was extracted for gas chromatography analysis. The analysis results are shown in Table 1.

[0082] Example 3

[0083] This embodiment provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and the preparation method thereof is as follows:

[0084] Equimolar amounts of asymmetric bisphosphine ligand PPh2C6H4N(tBu)PPh2, carbonyl rhodium compound Rh2Cl2(CO)4 and carbonyl ruthenium compound Ru3(CO)4 were added. 12 , placed in a Schlenk bottle, added toluene, stirred at room temperature for 12 hours, after the reaction, the solvent was removed under reduced pressure to obtain an asymmetric bidentate phosphine ligand coordinated bimetallic catalyst [PPh2C6H4N(tBu)PPh2]Rh(CO)2[PPh2C6H4N(tBu)PPh2]Ru(CO)2.

[0085] This embodiment also provides a method for preparing isononanal, comprising the following steps:

[0086] A 300mL high-pressure reactor was selected, and after flushing with N2, 1mmol of the bimetallic catalyst of this embodiment, 100mmol of isooctene, and 40mL of toluene were added in sequence, the injection valve was closed, the synthesis gas cylinder was connected, and the reaction was heated to 80°C. Under the conditions of a pressure of 1.0MPa and a stirring rate of 800rpm, the reaction was carried out for 4 hours; wherein the synthesis gas was carbon monoxide and H2, and the volume ratio of carbon monoxide to H2 was 1:1; the flow rate of the synthesis gas was 500mL / min; after the reaction was completed, the reactor was cooled to 0°C, the pressure was released to normal pressure, and the reaction product was extracted for gas chromatography analysis. The analysis results are shown in Table 1.

[0087] Example 4

[0088] This embodiment provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and the preparation method thereof is as follows:

[0089] Equimolar amounts of asymmetric bisphosphine ligand PPh2C6H4N(Ph)PPh2, carbonyl rhodium compound Rh2Cl2(CO)4 and carbonyl ruthenium compound Ru3(CO)4 were added. 12 , placed in a Schlenk bottle, added toluene, stirred at room temperature for 12 hours, after the reaction, the solvent was removed under reduced pressure to obtain asymmetric bidentate phosphine ligand coordinated bis[PPh2C6H4N(Ph)PPh2]Rh(CO)2[PPh2C6H4N(Ph)PPh2]Ru(CO)2.

[0090] This embodiment also provides a method for preparing isononanal, comprising the following steps:

[0091] A 300mL high-pressure reactor was selected, and after flushing with N2, 1mmol of the bimetallic catalyst of this embodiment, 100mmol of isooctene, and 40mL of toluene were added in sequence, the injection valve was closed, the synthesis gas cylinder was connected, and the reaction was heated to 80°C. Under the conditions of a pressure of 1.0MPa and a stirring rate of 800rpm, the reaction was carried out for 4 hours; wherein the synthesis gas was carbon monoxide and H2, and the volume ratio of carbon monoxide to H2 was 1:1; the flow rate of the synthesis gas was 500mL / min; after the reaction was completed, the reactor was cooled to 0°C, the pressure was released to normal pressure, and the reaction product was extracted for gas chromatography analysis. The analysis results are shown in Table 1.

[0092] Example 5

[0093] This embodiment provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and the preparation method thereof is as follows:

[0094] Equimolar amounts of asymmetric bisphosphine ligand PPh2C6H4N(2,4,6-Me3C6H2)PPh2, carbonyl rhodium compound Rh2Cl2(CO)4 and carbonyl ruthenium compound Ru3(CO)4 were added. 12, placed in a Schlenk bottle, added toluene, stirred at room temperature for 12 hours, after the reaction was completed, the solvent was removed under reduced pressure to obtain a bimetallic catalyst [PPh2C6H4N(H)PPh2]Rh(CO)2[PPh2C6H4N(H)PPh2]Ru(CO)2 coordinated by an asymmetric bidentate phosphine ligand.

[0095] This embodiment also provides a method for preparing isononanal, comprising the following steps:

[0096] A 300mL high-pressure reactor was selected, and after flushing with N2, 1mmol of the bimetallic catalyst of this embodiment, 100mmol of isooctene, and 40mL of toluene were added in sequence, the injection valve was closed, the synthesis gas cylinder was connected, and the reaction was heated to 80°C. Under the conditions of a pressure of 1.0MPa and a stirring rate of 800rpm, the reaction was carried out for 4 hours; wherein the synthesis gas was carbon monoxide and H2, and the volume ratio of carbon monoxide to H2 was 1:1; the flow rate of the synthesis gas was 500mL / min; after the reaction was completed, the reactor was cooled to 0°C, the pressure was released to normal pressure, and the reaction product was extracted for gas chromatography analysis. The analysis results are shown in Table 1.

[0097] Example 6

[0098] This embodiment provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and the preparation method thereof is as follows:

[0099] Equimolar amounts of asymmetric bisphosphine ligand PPh2C6H4N(Bu)PPh2, carbonyl rhodium compound Rh2Cl2(CO)4 and carbonyl ruthenium compound Ru3(CO)4 were added. 12 , placed in a Schlenk bottle, added toluene, stirred at room temperature for 12 hours, after the reaction was completed, the solvent was removed under reduced pressure to obtain a bimetallic catalyst [PPh2C6H4N(Bu)PPh2]Rh(CO)2[PPh2C6H4N(Bu)PPh2]Ru(CO)2 coordinated by an asymmetric bidentate phosphine ligand.

[0100] This embodiment also provides a method for preparing isononanal, comprising the following steps:

[0101] A 300mL high-pressure reactor was selected, and after flushing with N2, 1mmol of the bimetallic catalyst of this embodiment, 100mmol of isooctene, and 40mL of toluene were added in sequence, the injection valve was closed, the synthesis gas cylinder was connected, and the reaction was heated to 80°C. Under the conditions of a pressure of 1.0MPa and a stirring rate of 800rpm, the reaction was carried out for 4 hours; wherein the synthesis gas was carbon monoxide and H2, and the volume ratio of carbon monoxide to H2 was 1:1; the flow rate of the synthesis gas was 500mL / min; after the reaction was completed, the reactor was cooled to 0°C, the pressure was released to normal pressure, and the reaction product was extracted for gas chromatography analysis. The analysis results are shown in Table 1.

[0102] Example 7

[0103] This embodiment provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and the preparation method thereof is as follows:

[0104] Equimolar amounts of an asymmetric bisphosphine ligand P(2,6-iPr2C6H3)2C6H4N(Bu)P(2,6-iPr2C6H3)2, a carbonyl rhodium compound Rh2Cl2(CO)4, and a carbonyl ruthenium compound Ru3(CO)4 were added. 12 , placed in a Schlenk bottle, added toluene, stirred at room temperature for 12 hours, and after the reaction, the solvent was removed under reduced pressure to obtain a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand [P(2,6-iPr2C6H3)2C6H4N(Bu)P(2,6-iPr2C6H3)2]Rh(CO)2[P(2,6-iPr2C6H3)2C6H4N(Bu)P(2,6-iPr2C6H3)2]Ru(CO)2.

[0105] This embodiment also provides a method for preparing isononanal, comprising the following steps:

[0106] A 300mL high-pressure reactor was selected, and after flushing with N2, 1mmol of the bimetallic catalyst of this embodiment, 100mmol of isooctene, and 40mL of toluene were added in sequence, the injection valve was closed, the synthesis gas cylinder was connected, and the reaction was heated to 80°C. Under the conditions of a pressure of 1.0MPa and a stirring rate of 800rpm, the reaction was carried out for 4 hours; wherein the synthesis gas was carbon monoxide and H2, and the volume ratio of carbon monoxide to H2 was 1:1; the flow rate of the synthesis gas was 500mL / min; after the reaction was completed, the reactor was cooled to 0°C, the pressure was released to normal pressure, and the reaction product was extracted for gas chromatography analysis. The analysis results are shown in Table 1.

[0107] Example 8

[0108] This embodiment provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and the preparation method thereof is as follows:

[0109] Equimolar amounts of an asymmetric bisphosphine ligand P(2,6-iPr2C6H3)2C6H4N(Ph)P(2,6-iPr2C6H3)2, a carbonyl rhodium compound Rh2Cl2(CO)4, and a carbonyl ruthenium compound Ru3(CO)4 were added. 12, placed in a Schlenk bottle, added toluene, stirred at room temperature for 12 hours, and after the reaction was completed, the solvent was removed under reduced pressure to obtain an asymmetric bidentate phosphine ligand coordinated bimetallic catalyst [P(2,6-iPr2C6H3)2C6H4N(Ph)P(2,6-iPr2C6H3)2]Rh(CO)2[P(2,6-iPr2C6H3)2C6H4N(Ph)P(2,6-iPr2C6H3)2]Ru(CO)2.

[0110] This embodiment also provides a method for preparing isononanal, comprising the following steps:

[0111] A 300mL high-pressure reactor was selected, and after flushing with N2, 1mmol of the bimetallic catalyst of this embodiment, 100mmol of isooctene, and 40mL of toluene were added in sequence, the injection valve was closed, the synthesis gas cylinder was connected, and the reaction was heated to 80°C. Under the conditions of a pressure of 1.0MPa and a stirring rate of 800rpm, the reaction was carried out for 4 hours; wherein the synthesis gas was carbon monoxide and H2, and the volume ratio of carbon monoxide to H2 was 1:1; the flow rate of the synthesis gas was 500mL / min; after the reaction was completed, the reactor was cooled to 0°C, the pressure was released to normal pressure, and the reaction product was extracted for gas chromatography analysis. The analysis results are shown in Table 1.

[0112] Example 9

[0113] This embodiment provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and the preparation method thereof is as follows:

[0114] Equimolar amounts of an asymmetric bisphosphine ligand P(2,6-iPr2C6H3)2C6H4N(2,6-iPr2C6H3)P(2,6-iPr2C6H3)2, a carbonyl rhodium compound Rh2Cl2(CO)4, and a carbonyl ruthenium compound Ru3(CO)4 were added. 12 , placed in a Schlenk bottle, added toluene, stirred at room temperature for 12 hours, after the reaction, the solvent was removed under reduced pressure to obtain a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand [P(2,6-iPr2C6H3)2C6H4N(2,6-iPr2C6H3)P(2,6-iPr2C6H3)2]Rh(CO)2

[0115] [P(2,6-iPr2C6H3)2C6H4N(2,6-iPr2C6H3)P(2,6-iPr2C6H3)2]Ru(CO)2.

[0116] This embodiment also provides a method for preparing isononanal, comprising the following steps:

[0117] A 300mL high-pressure reactor was selected, and after flushing with N2, 1mmol of the bimetallic catalyst of this embodiment, 100mmol of isooctene, and 40mL of toluene were added in sequence, the injection valve was closed, the synthesis gas cylinder was connected, and the reaction was heated to 80°C. Under the conditions of a pressure of 1.0MPa and a stirring rate of 800rpm, the reaction was carried out for 4 hours; wherein the synthesis gas was carbon monoxide and H2, and the volume ratio of carbon monoxide to H2 was 1:1; the flow rate of the synthesis gas was 500mL / min; after the reaction was completed, the reactor was cooled to 0°C, the pressure was released to normal pressure, and the reaction product was extracted for gas chromatography analysis. The analysis results are shown in Table 1.

[0118] Example 10

[0119] This embodiment provides a bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, and the preparation method thereof is as follows:

[0120] Equimolar amounts of an asymmetric bisphosphine ligand P(2,4,6-Me3C6H2)2C6H4N(2,4,6-Me3C6H2)P(2,4,6-Me3C6H2)2, a carbonyl rhodium compound Rh2Cl2(CO)4 and a carbonyl ruthenium compound Ru3(CO)4 were added. 12 , placed in a Schlenk bottle, added toluene, stirred at room temperature for 12 hours, after the reaction, the solvent was removed under reduced pressure to obtain an asymmetric bidentate phosphine ligand coordinated bimetallic catalyst [P(2,4,6-Me3C6H2)2C6H4N(2,4,6-Me3C6H2)P(2,4,6-Me3C6H2)2]Rh(CO)2[P(2,4,6-Me3C6H2)2C6H4N(2,4,6-Me3C6H2)P(2,4,6-Me3C6H2)2]Ru(CO)2.

[0121] This embodiment also provides a method for preparing isononanal, comprising the following steps:

[0122] A 300mL high-pressure reactor was selected, and after flushing with N2, 1mmol of the bimetallic catalyst of this embodiment, 100mmol of isooctene, and 40mL of toluene were added in sequence, the injection valve was closed, the synthesis gas cylinder was connected, and the reaction was heated to 80°C. Under the conditions of a pressure of 1.0MPa and a stirring rate of 800rpm, the reaction was carried out for 4 hours; wherein the synthesis gas was carbon monoxide and H2, and the volume ratio of carbon monoxide to H2 was 1:1; the flow rate of the synthesis gas was 500mL / min; after the reaction was completed, the reactor was cooled to 0°C, the pressure was released to normal pressure, and the reaction product was extracted for gas chromatography analysis. The analysis results are shown in Table 1.

[0123] In the above embodiment, the content of each component in the reaction product was determined according to gas chromatography analysis, and the isooctene conversion rate and isononanal selectivity were calculated. The calculation formula is as follows:

[0124] Conversion rate of isooctene = (amount of isooctene added - amount of isooctene unreacted) / amount of isooctene added × 100%;

[0125] Yield of isononanal = mass of isononanal actually prepared / mass of isononanal theoretically obtained × 100%;

[0126] Selectivity of isononanal=yield of isononanal / conversion rate of isooctene×100%.

[0127] Table 1

[0128] Isooctene conversion rate (%) Isononanal selectivity (%) Example 1 97.1 98.2 Example 2 93.3 94.4 Example 3 95.6 91.3 Example 4 92.5 93.5 Example 5 96.2 97.2 Example 6 92.2 93.4 Example 7 96.7 94.8 Example 8 98.0 99.0 Example 9 98.3 96.8 Example 10 97.9 97.3

[0129] As can be seen from Table 1, when the bimetallic catalyst coordinated by the asymmetric bidentate phosphine ligand disclosed in the present invention is used for preparing isononanal by hydroformylation of isooctene, the conversion rate of isooctene is as high as 98.5%, and the selectivity of isononanal is as high as 99%.

[0130] Finally, it should be noted that the above embodiments are used to illustrate the technical solution of the present disclosure rather than to limit the protection scope of the present disclosure. Although the present disclosure has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that the technical solution of the present disclosure can be modified or replaced by equivalents without departing from the essence and scope of the technical solution of the present disclosure.

Claims

1. A bimetallic catalyst coordinated by an asymmetric bidentate phosphine ligand, characterized in that: The structure of the bimetallic catalyst is shown in formula (1): In formula (1), R1, R2, R3, and R4 are each independently any one of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl; R5 is any one of hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl.

2. The bimetallic catalyst according to claim 1, characterized in that The R1, R2, R3, and R4 are each independently any one of C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 substituted aryl, C6-C30 heteroaryl, C6-C30 substituted heteroaryl, C6-C30 aryloxy, C6-C30 heteroaryloxy, C6-C30 arylalkyl, and C6-C30 heteroarylalkyl.

3. The bimetallic catalyst according to claim 1, characterized in that The R5 is any one of H, C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C6-C30 substituted aryl, C6-C30 heteroaryl, C6-C30 substituted heteroaryl, C6-C30 aryloxy, C6-C30 heteroaryloxy, C6-C30 arylalkyl, and C6-C30 heteroarylalkyl.

4. The bimetallic catalyst according to claim 1, characterized in that The R1, R2, R3, and R4 are each independently any one of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopentyl, cyclohexyl, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 2,6-diisopropylphenyl, 2,6-di-tert-butylphenyl, 2,4,6-trimethylphenyl, 2,4,6-triisopropylphenyl, 2,4,6-tri-tert-butylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, and thienyl.

5. The bimetallic catalyst according to claim 1, characterized in that The R5 is any one of H, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopentyl, cyclohexyl, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 2,6-diisopropylphenyl, 2,6-di-tert-butylphenyl, 2,4,6-trimethylphenyl, 2,4,6-triisopropylphenyl, and 2,4,6-tri-tert-butylphenyl.

6. The method for preparing the bimetallic catalyst according to any one of claims 1 to 5, characterized in that: The following steps are involved: An asymmetric bidentate phosphine ligand, a carbonyl rhodium compound and a carbonyl ruthenium compound are reacted in an organic solvent to obtain a bimetallic catalyst, wherein the structural formula of the asymmetric bidentate phosphine ligand is R1R2PC6H4NR5PR3R4, R1, R2, R3, and R4 are independently any one of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl; and R5 is any one of hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, and heteroarylalkyl.

7. Use of the bimetallic catalyst according to any one of claims 1 to 5 in the preparation of isononanal.

8. The use according to claim 7, characterized in that The following steps are involved: Isooctene, carbon monoxide, hydrogen, an organic solvent and the bimetallic catalyst according to any one of claims 1 to 5 are reacted at 0-250° C. and 0.1-20 MPa for 0.01-100 h to obtain isononanal, wherein the concentration of the bimetallic catalyst is 0.001-100 mmol / L.

9. The use according to claim 8, characterized in that The reaction temperature is 50-150° C., the pressure is 0.1-5 MPa, and the time is 1-10 h; and / or the concentration of the bimetallic catalyst is 0.5-20 mmol / L.

10. The use according to claim 8, characterized in that The organic solvent is at least one of organic alcohol, phenol, ether, and aromatic solvents. Preferably, the organic solvent is at least one of methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, cyclopentanol, cyclohexanol, benzyl alcohol, phenol, benzene, toluene, ether, and tetrahydrofuran.

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