CN110963936B - Method for preparing amide compound - Google Patents

Method for preparing amide compound Download PDF

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CN110963936B
CN110963936B CN201811139502.7A CN201811139502A CN110963936B CN 110963936 B CN110963936 B CN 110963936B CN 201811139502 A CN201811139502 A CN 201811139502A CN 110963936 B CN110963936 B CN 110963936B
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olefin
butene
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ruthenium
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王峰
安静华
王业红
张志鑫
张健
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Dalian Institute of Chemical Physics of CAS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • B01J23/462—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/63—Platinum group metals with rare earths or actinides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/648—Vanadium, niobium or tantalum or polonium
    • B01J23/6484—Niobium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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Abstract

The invention relates to a method for preparing amide compounds. The method adopts amine, olefin and carbon monoxide as reaction substrates, adopts an organic solvent as a solvent, and prepares the amide compound under the catalytic action of ruthenium-loaded metal oxide. The reaction process is as follows: adding a solvent, amine, olefin and a catalyst into a pressure container, charging carbon monoxide, sealing, stirring, reacting at a temperature of not less than 130 ℃, reacting for not less than 2 hours, easily separating the catalyst from a reaction system after reaction, recycling for many times, and obtaining the highest yield of the amide compound of 90%.

Description

Method for preparing amide compound
Technical Field
The invention relates to a method for preparing amide compounds, in particular to a method for preparing amide compounds by the hydroamidation reaction of olefin, carbon monoxide and amine.
Background
Amide compounds and derivatives of amide compounds are used in pharmaceutical, chemical, and fuel applications, such as synthetic perfumes, flavoring agents, detergents, and surfactants.
Methods for preparing amide compounds have been reported. In 2013, Matthias Beller topic group reported that amides were prepared using homogeneous Pd as catalyst, p-toluenesulfonic acid as acid additive, and a phosphorus ligand added, where the CO pressure required in the reaction was 3MPa (Fang, X.; Jacksell, R.; Beller, M.Angew.Chem.int.Ed,2013,52, 14089.). In 2015, Huang Han professor of national focus laboratory of Lanzhou chemical research institute of Chinese academy of sciences, oxidatively synthesized and selectively oxidized, reported that a more linear amide product was obtained using a homogeneous Pd complex as a catalyst and an aminal as an amine source (Zhang, G.; Gao, B.; Huang, H.Angew.chem.int. Ed,2015,54,7657.), but an acid additive was added during the reaction to promote the reaction. In addition, in 2016, professor Matthias Beller reported a homogeneous PdCl2Amide compounds (Li, h.; Dong, k.; Neumann, h.; Beller, m.angelw.chem.int.ed, 2015,54,10239.) were prepared as catalysts, but complicated ligands were added during the reaction, increasing the complexity of the reaction process. In addition, in 2016, the Matthias Beller topic group reported a homogeneous PdCl2In the presence of a catalyst, a special pyrrole ligand with a phosphorus substituent at the 2-position can also give better amide yield when an aliphatic amine is used as a substrate, and the product is mainly branched amide. In 2015, Liu national task group of institute of organic chemistry of Chinese academy of sciences reported that a homogeneous Pd complex was used as a catalyst to catalyze intramolecular amine carbonylation (Cheng, J.; Qi, X.; Li, M.; Chen, P.; Liu, G.J Am Chem Soc 2015,137,2480.), and an oxidant was added during the reaction, thereby realizing the preparation of amide compounds from simple olefins. Furthermore, patent 104926578A reports a process for the preparation of fatty amides characterized by substitutionThe terminal olefin, carbon monoxide and amine acetal or amine are used as raw materials, and the aliphatic amide compound is prepared under the catalysis of a transition metal catalyst or the catalysis of the transition metal catalyst and aldehyde together with a ligand and an additive.
Although the current methods for preparing amide compounds have been developed to a certain extent, problems still exist, such as long preparation route, complex catalyst preparation, complex ligand preparation, auxiliary catalyst, difficult separation, easy catalyst deactivation and the like. Therefore, a technical route for preparing the amide compound with high efficiency and low cost is developed, and the method has an important application prospect.
Disclosure of Invention
The invention has the significance of overcoming the defects in the prior process for preparing the amide compounds, preparing the compounds with high efficiency and low cost under mild conditions, and easily separating the catalyst and recycling the catalyst for many times. The invention uses solid catalyst, which has better selectivity to the continuous amide compared with the homogeneous catalyst under the same condition.
The technical scheme adopted by the invention is as follows:
a method for preparing an amide compound:
the preferred scheme is as follows:
adding a solvent, an amine compound, olefin and a ruthenium-loaded metal oxide catalyst into a pressure container, charging carbon monoxide, sealing, stirring, and reacting at a temperature of more than or equal to 130 ℃ for more than or equal to 2 hours;
the ruthenium-supported metal oxide catalyst is Ru/TiO2、Ru/Nb2O5、Ru/CeO2、Ru/Al2O3One or more of the above;
the mass fraction of ruthenium in the ruthenium-supported metal oxide catalyst is 0.15wt% -10 wt%.
The pressure of charging carbon monoxide is 0.1MPa to 10 MPa.
The solvent is as follows: one or more of tetrahydrofuran, p-xylene, toluene, acetonitrile, 1, 4-dioxane, cyclohexane and n-hexane.
The amine compound is: n-propylamine, one or more of n-butylamine, dimethylamine, aniline, benzylamine, p-anisidine, p-chloroaniline and p-nitrobenzylamine;
the olefin is: one or more of ethylene, trimethylethylene, propylene, 1-butene, 2-butene, isobutene, 1-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, styrene, alpha-methylstyrene, propenylbenzene and cyclohexene. The equation is:
Figure BDA0001815458300000031
wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product;
wherein R is1Is phenyl or phenyl containing substituent, wherein the substituent is-F, -Cl, -Br, I, -OCH3C1-C3 alkyl or hydrogen; r2Is methyl or hydrogen; r3Is methyl or hydrogen; r4Is methyl or hydrogen; r5Is methyl, phenyl or phenyl containing substituent, wherein the substituent is-F, -Cl, -Br, I, -OCH3C1-C3 alkyl, or C1-C3 alkyl with hydroxyl.
The addition of the olefin was: when the olefin is the gaseous olefin of ethylene, trimethylethylene, propylene, 1-butene, 2-butene and isobutene, the charging pressure is 0.1-10 MPa; when the olefin is liquid olefin of 1-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, styrene, alpha-methylstyrene, propenylbenzene and cyclohexene, the amount of the olefin added per mL of the solvent is 0.04 to 5 mmol/mL.
The adding amount of the amine compound is as follows: the amount of the olefin added per milliliter of the solvent is 0.04 to 5 mmol/mL.
The reaction temperature is 150-200 ℃, and the reaction time is 2-24 h.
The best scheme is as follows:
the solvent is as follows: one or more of tetrahydrofuran, p-xylene, toluene and acetonitrile.
The amine compound is: one or more of n-propylamine, n-butylamine, aniline, benzylamine, p-anisidine and p-chloroaniline;
the olefin is one or more of ethylene, propylene, isobutene, styrene and cyclohexene;
the addition of the olefin was: when the olefin is gas olefin of ethylene, propylene and isobutene, the pressure is 0.5-5 MPa; when the olefin is liquid olefin of styrene and cyclohexene, the amount of the olefin added in each milliliter of solvent is 0.1-2 mol/L;
the adding amount of the amine compound is as follows: the amount of the olefin added per milliliter of the solvent is 0.1 to 2 mmol/mL.
The ruthenium-loaded metal oxide catalyst is Ru/CeO2；
The mass fraction of ruthenium in the ruthenium-supported metal oxide catalyst is 1.0-5 wt%;
the pressure of charging carbon monoxide is 0.5 MPa-5 MPa.
The reaction temperature is 160-180 ℃, and the reaction time is 5-20 h.
The catalyst was used in an amount of 0.005g (mmol olefin)-1About 0.50g (mmol olefin)-1；
The catalyst is preferably used in an amount of 0.01g (mmol of olefin)-1About 0.3g (mmol olefin)-1；
More preferably, the catalyst is used in an amount of 0.02g (mmol of olefin)-1About 0.2g (mmol olefin)-1。
Compared with the traditional method for preparing amides, the method has the following advantages:
1. the catalyst has high activity, and the yield of the amide compound can reach 90 percent;
2. the catalyst is simple to prepare, can be separated from a reaction system through the existing chemical unit operation, and can be recycled for multiple times;
3. the product has good applicability, and is suitable for various olefins and amines.
4. The catalyst used in the invention is a solid catalyst, and has better selectivity to linear amide.
Drawings
FIG. 1 is a gas-mass spectrum of the product of example 2, wherein FIG. 1(a) is a chromatogram, FIG. 1(b) is a mass spectrum of the amide product with a retention time of 9.038min and its standard library mass spectrum is shown in FIG. 1 (c).
Detailed Description
In order to further illustrate the present invention in detail, several specific examples are given below, but the present invention is not limited to these examples. Examples 1-12 are liquid olefins and examples 13-15 are gaseous olefins.
Example 1
In a 15mL polytetrafluoroethylene-lined reaction vessel, 2mL tetrahydrofuran, 0.3mmol styrene, 0.5mmol benzylamine, and 0.1g of 0.15wt% Ru/CeO were added2Adding catalyst, adding magneton, charging 0.5MPa CO, sealing, stirring at 180 deg.C for 12 hr, and after reaction, determining the product by mass spectrum and gas chromatography. The conversion and selectivity of styrene are shown in Table 1. The product is shown below:
Figure BDA0001815458300000051
wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product.
Example 2
In a 15mL polytetrafluoroethylene-lined reactor, 2mL tetrahydrofuran, 0.5mmol aniline, and 0.1g of 2 wt% Ru/CeO were added2Adding catalyst, adding magneton, charging 0.5MPa ethylene and 0.5MPa CO, sealing, stirring at 180 deg.C for 4 hr, and after the reaction is finished, the product is qualitative by mass spectrogram and quantitative by gas chromatography. The conversion and selectivity of aniline are shown in table 1. The product is shown below:
Figure BDA0001815458300000061
example 3
2mL of tetrahydrofuran and 0.5mmol of aniline were added to a 15mL polytetrafluoroethylene-lined reaction vessel,and 0.1g of 5wt% Ru/CeO2Adding catalyst, adding magneton, charging 0.5MPa ethylene and 0.5MPa CO, sealing, stirring at 180 deg.C for 4 hr, and after the reaction is finished, the product is qualitative by mass spectrogram and quantitative by gas chromatography. The aniline conversion and product selectivity are shown in table 1. The product was the same as in example 1.
Figure BDA0001815458300000062
Example 4
In a 15mL Teflon lined reactor, 2mL tetrahydrofuran, 0.3mmol styrene, 0.5mmol aniline, and 0.1g 2 wt% Ru/TiO were added2Adding catalyst, adding magneton, charging 0.5MPa CO, sealing, stirring at 180 deg.C for 12 hr, and after reaction, determining the product by mass spectrum and gas chromatography. The conversion and selectivity of styrene are shown in Table 1. The product is shown below:
Figure BDA0001815458300000063
wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product.
Example 5
In a 15mL polytetrafluoroethylene-lined reaction vessel, 2mL tetrahydrofuran, 0.3mmol 1-pentene, 0.5mmol benzylamine, and 0.1g 2 wt% Ru/CeO were added2Adding catalyst, adding magneton, charging 0.7MPa CO, sealing, stirring at 180 deg.C for 6h, and after the reaction is finished, the product is qualitative by mass spectrogram and quantitative by gas chromatography. The conversion and selectivity of 1-pentene is shown in Table 1.
Figure BDA0001815458300000064
Wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product.
Example 6
In a 15mL polytetrafluoroethylene-lined reactor, the components were added2mL of tetrahydrofuran, 0.3mmol of cyclohexene, 0.5mmol of aniline and 0.1g of 2 wt.% Ru/CeO2Adding catalyst, adding magneton, charging 0.7MPa CO, sealing, stirring at 180 deg.C for 12 hr, and after reaction, determining the product by mass spectrum and gas chromatography. The cyclohexene conversion and selectivity are shown in Table 1. The product is shown below:
Figure BDA0001815458300000071
example 7
In a 15mL polytetrafluoroethylene-lined reaction vessel, 4mL tetrahydrofuran, 0.3mmol cyclohexene, 0.5mmol benzylamine and 0.1g 2 wt% Ru/CeO were added2Adding catalyst, adding magnetons, charging 3MPa CO, sealing, stirring at 180 deg.C, reacting for 12h, and determining the product by mass spectrum and gas chromatography. The conversion and selectivity of styrene are shown in Table 1. The product was the same as in example 1.
Figure BDA0001815458300000072
Example 8
In a 15mL Teflon lined reactor, 2mL tetrahydrofuran, 0.6mmol isobutylene, 0.5mmol aniline, and 0.1g 2 wt% Ru/TiO, respectively2Adding catalyst, adding magneton, charging 0.5MPa CO, sealing, stirring at 200 deg.C for 8 hr, and qualitative and quantitative determination by mass spectrum and gas chromatography. The conversion and selectivity of aniline are shown in table 1. The product is shown in the following figure.
Figure BDA0001815458300000073
Wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product.
Example 9
In a 15mL polytetrafluoroethylene-lined reaction vessel, 2mL of tetrahydrofuran and 0.3mmol of styrene were added0.5mmol of n-butylamine and 0.1g of 5wt% Ru/TiO2Adding catalyst, adding magneton, charging 0.5MPa CO, sealing, stirring at 170 deg.C for 8 hr, and quantifying by mass spectrum and gas chromatography. The conversion and selectivity of styrene are shown in Table 1. The product was the same as in example 1.
Figure BDA0001815458300000081
Wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product.
Example 10
In a 15mL Teflon lined reactor, 2mL of p-xylene, 0.3mmol of cyclohexene, 0.5mmol of aniline and 0.1g of 2 wt% Ru/CeO were added2Adding catalyst, adding magneton, charging 0.7MPa CO, sealing, stirring at 180 deg.C for 12 hr, and after reaction, determining the product by mass spectrum and gas chromatography. The cyclohexene conversion and selectivity are shown in Table 1. The product is shown below:
Figure BDA0001815458300000082
example 11
In a 15mL polytetrafluoroethylene-lined reactor, 2mL tetrahydrofuran, 0.3mmol cyclohexene, 0.5mmol aniline, and 0.1g 2 wt% Ru/SiO were added2Adding catalyst, adding magneton, charging 0.7MPa CO, sealing, stirring at 180 deg.C for 12 hr, and after reaction, determining the product by mass spectrum and gas chromatography. The cyclohexene conversion and selectivity are shown in Table 1. The product is shown in example 10:
example 12
In a 15mL Teflon lined reactor, 2mL tetrahydrofuran, 0.3mmol 3-methyl-1-butene, 0.5mmol ethylamine and 0.1g 2 wt% Ru/CeO were added2Adding catalyst, adding magneton, charging 0.7MPa CO, sealing, stirring at 180 deg.C for 12 hr, and determining the product by mass spectrum and gas chromatographyAnd (4) quantifying. The conversion and selectivity of 3-methyl-1-butene are shown in Table 1.
Figure BDA0001815458300000091
Wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product.
Example 13
In a 15mL polytetrafluoroethylene-lined reactor, 2mL tetrahydrofuran, 0.3mmol isobutylene, 0.5mmol n-propylamine and 0.1g of 0.1 wt% Ru/Al were charged, respectively2O3Adding magnetons and 0.5MPa CO into the catalyst, sealing, stirring and reacting for 8 hours at 180 ℃, and after the reaction is finished, determining the product by adopting a mass spectrogram and quantifying by adopting a gas chromatography. The conversion and selectivity of isobutene are shown in Table 1.
Figure BDA0001815458300000092
Wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product.
Example 14
In a 15mL Teflon lined reactor, 2mL of tetrahydrofuran, and 0.15g of 2 wt% Ru/CeO were added2Adding catalyst, adding magneton, charging 0.5MPa CO and 0.5MPa propylene, sealing, stirring at 200 deg.C for 36h, and after the reaction is finished, the product is qualitative by mass spectrogram and quantitative by gas chromatography. The conversion and selectivity of ethylene are shown in table 1. The product is shown in the following figure:
Figure BDA0001815458300000093
wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product.
Example 15
In a 15mL polytetrafluoroethylene-lined reactor, 2mL tetrahydrofuran, 0.5mmol cyclohexylamine, and 0.15g of 2 wt% Ru/CeO were added2Catalyst, adding magneton, charging 0.5MPa CO and 0.5MPa propylene,and (3) sealing, stirring at 180 ℃ for reacting for 36h, and after the reaction is finished, determining the product by using a mass spectrum and quantifying by using a gas chromatography. The conversion and selectivity of ethylene are shown in table 1. The product is shown in the following figure:
Figure BDA0001815458300000101
wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product.
TABLE 1 evaluation results of direct preparation of amide-based compounds
Figure BDA0001815458300000102
Figure BDA0001815458300000111
The catalyst and the reaction system after the reaction are easy to separate and can be recycled for many times, and the yield of the amide compound reaches up to 90 percent.

Claims (10)

1. A method for producing an amide compound, characterized in that:
adding a solvent, an amine compound, olefin and a ruthenium-loaded metal oxide catalyst into a pressure container, charging carbon monoxide, sealing, stirring, wherein the reaction temperature is more than or equal to 130 ℃, and the reaction time is more than or equal to 2 hours;
the ruthenium-supported metal oxide catalyst is Ru/TiO2、Ru/CeO2、Ru/Al2O3One or more of the above;
the mass fraction of ruthenium in the ruthenium-supported metal oxide catalyst is 0.15-10 wt%;
the amine compound is: n-propylamine, one or more of n-butylamine, dimethylamine, cyclohexylamine, aniline, benzylamine, p-anisidine, p-chloroaniline and p-nitrobenzylamine;
the olefin is: one or more of ethylene, trimethylethylene, propylene, 1-butene, 2-butene, isobutene, 1-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, styrene, alpha-methylstyrene, propenylbenzene and cyclohexene;
the synthesis route for preparing the amide compound is as follows:
Figure 856487DEST_PATH_IMAGE001
；
wherein the product 1 is a straight-chain product and the product 2 is a branched-chain product;
wherein R is1，R2，R3，R4Are the corresponding radicals of the abovementioned olefins, with the exception of the vinyl radical; r5Are corresponding groups except the amine group in the amine compound.
2. The method of claim 1, wherein:
the pressure of charging carbon monoxide is 0.1MPa to 10 MPa;
the solvent is one or more of tetrahydrofuran, p-xylene, toluene, acetonitrile, 1, 4-dioxane, cyclohexane and n-hexane.
3. The method of claim 1, wherein:
the addition of the olefin was: when the olefin is one or more of gas olefins of ethylene, trimethylethylene, propylene, 1-butene, 2-butene and isobutene, the charging pressure is 0.1-10 MPa; when the olefin is one or more of liquid olefins such as 1-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, styrene, alpha-methylstyrene, propenylbenzene and cyclohexene, the addition amount of the olefin added in each milliliter of the solvent is 0.04-5 mmol/mL;
the adding amount of the amine compound is as follows: the amount of the amine compound added to each milliliter of solvent is 0.04-5 mmol/mL.
4. The method of claim 1, wherein:
the reaction temperature is 150-200 ℃, and the reaction time is 2-24 h.
5. The method of claim 1, wherein:
the solvent is one or more of tetrahydrofuran, p-xylene, toluene and acetonitrile;
the amine compound is: one or more of n-propylamine, n-butylamine, aniline, cyclohexylamine, benzylamine, p-methoxyaniline and p-chloroaniline;
the olefin is: one or more of ethylene, propylene, 2-butylene, isobutene, 2-pentene, 2-methyl-2-butene, styrene, propenyl benzene and cyclohexene;
the addition of the olefin was: when the olefin is one or more of gas olefins of ethylene, propylene, 2-butylene and isobutene, the pressure is 0.2-8 MPa; when the olefin is one or more of liquid olefins such as 2-pentene, 2-methyl-1-butene, styrene, propenyl benzene and cyclohexene, the addition amount of the olefin added in each milliliter of solvent is 0.05-1 mmol/mL;
the adding amount of the amine compound is as follows: the amount of the amine compound added in each milliliter of solvent is 0.05-1 mmol/mL;
the ruthenium-supported metal oxide catalyst is Ru/TiO2、Ru/CeO2One or more of the above;
the mass fraction of ruthenium in the ruthenium-supported metal oxide catalyst is 0.5-8 wt%;
the pressure of charging carbon monoxide is 0.2 MPa to 8 MPa.
6. The method of claim 1, wherein:
the solvent is one or more of tetrahydrofuran, p-xylene and toluene;
the amine compound is: one or more of n-propylamine, n-butylamine, aniline and benzylamine;
the olefin is one or more of ethylene, propylene, isobutene, styrene and cyclohexene;
the addition of the olefin was: when the olefin is one or more of gas olefins of ethylene, propylene and isobutene, the pressure is 0.5-5 MPa; when the olefin is one or two of liquid olefins of styrene and cyclohexene, the amount of the olefin added in each milliliter of solvent is 0.1-2 mol/L;
the adding amount of the amine compound is as follows: the amount of the amine compound added in each milliliter of solvent is 0.1-2 mmol/mL;
the ruthenium-loaded metal oxide catalyst is Ru/CeO2；
The mass fraction of ruthenium in the ruthenium-supported metal oxide catalyst is 1.0-5 wt%;
the pressure of charging carbon monoxide is 0.5 MPa-5 MPa.
7. The method of claim 1, wherein:
the reaction temperature is 160-180 ℃, and the reaction time is 5-20 h.
8. The method of claim 1, wherein:
the catalyst was used in an amount of 0.005g (mmol olefin)-1About 0.50g (mmol olefin)-1。
9. The method of claim 8, wherein:
the catalyst was used in an amount of 0.01g (mmol olefin)-1About 0.3g (mmol olefin)-1。
10. The method of claim 8, wherein:
the catalyst was used in an amount of 0.02g (mmol olefin)-1About 0.2g (mmol olefin)-1。
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Citations (1)

* Cited by examiner, † Cited by third party
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CN104926578A (en) * 2015-04-03 2015-09-23 中国科学院兰州化学物理研究所 Preparation method for fatty acyl amide

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