CN113101924A - Monoatomic and particle synergistic supported metal catalyst and preparation method and application thereof - Google Patents
Monoatomic and particle synergistic supported metal catalyst and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a single atom and particle synergistic supported metal catalyst, and a preparation method and application thereof. In the metal catalyst of the present invention, the metal is uniformly supported on the carrier in the form of the coexistence of the monoatomic metal and the nanoparticle. The metal is at least one of Ir, Ru, Rh, Pd, Co and Pt. The pore diameter of the carrier is 0.5-10 nm, and the specific surface area is 200-1500 m2(ii) in terms of/g. The carrier is any one of mesoporous carbon, mesoporous molecular sieve and active carbon. The single-atom and particle synergistic supported metal catalyst shows excellent activity and selectivity in the hydrogenation reaction of quinoline compounds, aromatic nitro compounds, aromatic aldehyde or carbonyl compounds, has higher catalytic activity than the currently reported catalyst under the same or similar reaction conditions, and shows excellent industrial application prospect; the single-atom and particle synergistic supported metal catalyst is prepared by a simple impregnation and high-temperature pyrolysis method, and the method is simple, has adjustable metal loading capacity and good reproducibility and is suitable for various metals.
Description
Technical Field
The invention belongs to the field of catalysts, and particularly relates to a single-atom and particle synergistic supported metal catalyst, and a preparation method and application thereof.
Background
Aromatic amine, aromatic alcohol, tetrahydroquinoline and derivatives thereof are very important intermediates for preparing medicines and organically synthesizing, and are mainly prepared by hydrogenation reaction of nitrobenzene, aromatic aldehyde or carbonyl compounds, quinoline and derivatives thereof. In recent years, researchers have reported a series of catalysts for liquid phase hydrogenation, including non-noble metals as well as noble metal homogeneous/heterogeneous catalysts, however, the catalysts reported to date have low catalytic activity, poor product selectivity, and demanding reaction conditions. Most heterogeneous catalysts are single site-supported catalysts, namely granular catalysts and monatomic catalysts, the TOF is low, and a suitable and simple means needs to be found for preparing high-activity catalysts for liquid-phase hydrogenation reaction. The monatomic catalyst has attracted attention because of its monodispersed active sites, high activity utilization rate, and electronic structure that the granular catalyst does not have. However, it has been reported in the literature that monatomic catalysts are not all catalytic reactions suitable for use. Therefore, it is a problem to be solved by the present invention to find a catalyst which has high activity and is suitable for hydrogenation reaction of various compounds.
Disclosure of Invention
The invention aims to provide a single-atom and particle synergistic supported metal catalyst, and a preparation method and application thereof.
The metal catalyst provided by the invention is uniformly loaded on a carrier in a mode of coexistence of single atoms and nano particles.
In the above metal catalyst, the metal may be at least one of Ir, Ru, Rh, Pd, Co and Pt.
In the metal catalyst, the pore diameter of the carrier can be 0.5-10 nm, specifically 4-10 nm, 4nm or 8 nm; the specific surface area can be 200-1500 m2A specific value of 200 to 1000 m/g2/g、200m2/g、600m2In g or 1000m2(ii) in terms of/g. Specifically, the support may be any one of mesoporous carbon (e.g., ordered mesoporous carbon CMK-3), mesoporous molecular sieve (e.g., commercial SBA-15 molecular sieve), and activated carbon (e.g., commercial activated carbon).
In the above metal catalyst, the loading amount of the metal catalyst may be 0.1% to 10%, specifically 0.2% to 4%, more specifically 0.3% to 3%, such as 2% to 3%, 2%, 2.5% or 3% by mass.
In the metal catalyst, the particle size of the nanoparticles can be 0.5-5 nm.
The invention further provides a preparation method of the metal catalyst, which comprises the following steps:
(1) dipping the carrier in a solution consisting of metal salt of the metal and a solvent, and removing the solvent after dipping to obtain a metal catalyst precursor;
(2) and pyrolyzing the metal catalyst precursor to obtain the single-atom and particle synergistic supported metal catalyst.
In the above production method, in the step (1), the metal salt may be present in the form of at least one salt selected from the group consisting of a nitrate, a sulfate, a hydrochloride, an acetylacetonate, and an acetate.
The solvent may be at least one of ethanol, methanol, acetone, carbon tetrachloride and water.
In the solution composed of the metal salt and the solvent, the concentration of the metal salt can be 0.1-10 mmol/L, specifically 0.5-5 mmol/L, more specifically 1-5 mmol/L, 1-4 mmol/L, 4-5 mmol/L, 2mmol/L, 1mmol/L, 4mmol/L or 5 mmol/L.
In the preparation method, in the step (1), in an impregnation system composed of the metal salt, the solvent and the carrier, the concentration of the carrier may be 10 to 500mg/mL, specifically 50 to 200mg/mL, and more specifically 20 mg/mL.
In the above production method, in the step (1), the impregnation is performed under stirring conditions; the stirring speed can be 100-1000 rpm, specifically 200-600 rpm, such as 400 r/min; the time can be 0.5 to 24 hours, specifically 2 to 12 hours, and more specifically 6 hours.
In the above preparation method, in the step (1), the solvent removal is performed by rotary evaporation; the rotary evaporation temperature can be 20-80 ℃, and specifically:
the solvent is ethanol; the temperature of the rotary evaporation can be 20-60 ℃, specifically 20-50 ℃, and more specifically 40-50 ℃;
the solvent is water; the temperature of the rotary evaporation can be 20-80 ℃, specifically 30-60 ℃, more specifically 50-60 ℃, such as 60 ℃;
the solvent is methanol; the temperature of the rotary evaporation can be 20-60 ℃, specifically 20-50 ℃, and more specifically 40-50 ℃;
the solvent is acetone, and the rotary evaporation temperature is 20-60 ℃, specifically 20-50 ℃, more specifically 20-40 ℃, such as 30 ℃.
The rotary evaporation time can be 5-30 min, specifically 10-20 min, such as 15-20 min, 15min or 20 min.
In the above-described production method, in the step (2), the pyrolysis may be performed under any one or more atmospheres of nitrogen, argon, and hydrogen.
In the preparation method, in the step (2), the temperature rise rate of the pyrolysis can be 1-5 ℃/min, such as 5 ℃/min; the pyrolysis temperature can be 200-1000 ℃, specifically 300-1000 ℃, more specifically 300-900 ℃, such as 500-800 ℃, 500-700 ℃, 500 ℃, 550 ℃, 600 ℃ or 700 ℃; the time may be 1 to 4 hours, such as 2 hours.
The invention also provides application of the single-atom and particle synergistic supported metal catalyst in catalysis of hydrogenation reaction of quinoline compounds, aromatic nitro compounds, aromatic aldehyde or carbonyl compounds.
The quinoline compound can be quinoline;
the aromatic nitro compound can be nitrobenzene;
the aromatic aldehyde may be benzaldehyde or phenylacetaldehyde.
In the application, the hydrogenation reaction is carried out in a solvent; the solvent may be at least one of tetrahydrofuran, methanol, ethanol, toluene, acetonitrile, and water.
In the above application, in the hydrogenation reaction, the ratio of the compound, the solvent, hydrogen and the catalyst may be 0.5 to 3 mmol: 3-10 mL: 0.1-4 MPa: 5-20 mg, such as 0.5-3 mmol: 3-10 mL: 0.1-4 MPa: 5mg, 0.5-2 mmol: 3-10 mL: 0.1-4 MPa: 5-20 mg, 0.5-2 mmol: 2-6 mL: 0.1-2 MPa: 5mg, 0.5 mmol: 6mL of: 2 MPa: 5mg, 0.5 mmol: 5mL of: 0.1 MPa: 5mg, 2 mmol: 5mL of: 2 MPa: 5mg or 0.5 mmol: 6mL of: 2 MPa: 5 mg.
In the above application, in the hydrogenation reaction, the hydrogenation temperature may be 20 to 140 ℃, for example, 25 to 100 ℃, 25 ℃ or 100 ℃; the time period may be 5 to 240 minutes, such as 40 to 60 minutes, 40 minutes or 60 minutes.
The invention has the following beneficial effects:
the single-atom and particle synergistic supported metal catalyst is prepared by a simple impregnation and high-temperature pyrolysis method, and the preparation method is simple, has adjustable metal loading capacity and good reproducibility and is suitable for various metals (such as Ir, Ru, Rh, Pd, Co, Pt and the like). The catalyst shows excellent activity and selectivity in the hydrogenation reaction of quinoline compounds, aromatic nitro compounds, aromatic aldehyde compounds or carbonyl compounds, has higher catalytic activity than the currently reported catalyst under the same or similar reaction conditions, and shows excellent industrial application prospect.
Drawings
FIG. 1 is a spherical aberration corrected high-angle annular dark field image of an iridium metal catalyst Ir-CMK-3 with synergy of mesoporous carbon-supported monatomic and particles prepared in example 1, wherein small bright spots in a small circle are iridium atoms, and large bright spots in a large circle are iridium particles.
FIG. 2 is a TEM image of Ir-CMK-3 catalyst prepared in example 1.
FIG. 3 is a plot of the area scan distribution of the Ir-CMK-3 catalyst prepared in example 1, wherein FIG. 3(a) is the corresponding STEM image, FIG. 3(b) is the corresponding EDS layered image, FIG. 3(C) is the corresponding C element distribution image, and FIG. 3(d) is the Ir element distribution image.
FIG. 4 is an EXAFS spectrum of the R space of the Ir-CMK-3 catalyst prepared in example 1, from which the Ir-C bond and the Ir-Ir bond can be seen.
FIG. 5 is a spherical aberration corrected high angle annular dark field image of the mesoporous carbon supported monatomic iridium metal catalyst Ir-CMK-3 prepared in the comparative example, where the small bright spots within the small circle are iridium atoms.
Detailed Description
According to the metal catalyst provided by the invention, metal is uniformly loaded on a carrier in a mode of coexistence of single atoms and nano particles. The metal may be at least one of Ir, Ru, Rh, Pd, Co and Pt. The pore diameter of the carrier can be 0.5-10 nm, and the specific surface area can be 200-1500 m2(ii)/g; the carrier can be any one of mesoporous carbon, mesoporous molecular sieve and activated carbon, such as any one of ordered mesoporous carbon CMK-3, commercial SBA-15 molecular sieve and commercial activated carbon. The loading amount of the metal catalyst can be 0.1-10% by mass percentage. The metal catalyst is a catalyst with the synergy of particles of various metals such as Ir, Ru, Rh, Pd, Co, Pt and the like and single atoms, the catalyst shows excellent activity and selectivity in the hydrogenation reaction of nitrobenzene, aromatic aldehyde or carbonyl compounds, quinoline and derivatives thereof, and the catalytic activity of the catalyst is far higher than that of the catalyst reported at present under the same or similar reaction conditions, thus showing excellent industrial application prospect.
The preparation method of the metal catalyst provided by the invention comprises the following steps: (1) soaking the carrier in a solution consisting of metal salt and a solvent, and removing the solvent after soaking to obtain a metal catalyst precursor; (2) and pyrolyzing the precursor of the metal catalyst to obtain the single-atom and particle synergistic supported metal catalyst. The invention utilizes a simple impregnation method and a high-temperature pyrolysis method to prepare the monatomic and particle synergistic supported metal catalyst, the metal precursor is supported on the surface of the carrier through the impregnation method, and due to the high specific surface area of the carrier, the metal salt precursor is decomposed in the high-temperature pyrolysis process and anchored in the carrier pore canal in the form of the coexistence of monatomic and particle, thereby obtaining the monatomic and particle synergistic supported metal catalyst.
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The support CMK-3 used in the examples described below had a pore size of 4nm and a specific surface area of 1000m2/g。
The carrier Active carbon Vulcan XC-72R Active carbon has the pore diameter of 10nm and the specific surface area of 200m2/g。
The carrier SBA-15 has a pore diameter of 8nm and a specific surface area of 600m2/g。
Example 1 preparation and application of Mono-atom and particle synergistic Iridium Metal catalyst Supported by mesoporous carbon
Preparing the iridium metal catalyst with the synergy of the mesoporous carbon supported monoatomic particles and the particles according to the following steps:
(1) 5mg of iridium acetylacetonate in a 25mL single-neck flask was weighed, 5mL of acetone was added, and the mixture was stirred for 15 minutes. 100mg of CMK-3 was weighed out and added to the solution, stirred at 400r/min for 6 hours, and then rotary evaporated at 30 ℃ and 100rpm for 15 minutes.
(2) Putting the solid powder obtained by rotary evaporation in the step (1) into a porcelain boat, and carrying out pyrolysis in a tube furnace. In an argon atmosphere, heating to 600 ℃ at a heating rate of 5 ℃/min, keeping for 2h, and then naturally cooling to room temperature to obtain the iridium metal catalyst Ir-CMK-3 with the loading of 2 wt% of mesoporous carbon loaded monoatomic and particle synergy.
The spherical aberration correction high-angle annular dark field image of the catalyst prepared in the embodiment is shown in fig. 1, and it can be seen that small bright spots in the image represent iridium atoms, and large bright spots are iridium particles. The TEM image is shown in FIG. 2. It can also be seen from the surface-scan profile (FIG. 3) that the iridium is uniformly distributed over the catalyst. The EXAFS spectrum of the R space (fig. 4) can reveal Ir-C bonds and Ir-Ir bonds in the catalyst, further demonstrating the coexistence of single atoms with the particles.
The iridium metal catalyst with the synergy of the mesoporous carbon-supported single atom and the particles is applied to the hydrogenation reaction of quinoline, and the specific implementation steps are as follows: weighing 5.0mg of Ir-CMK-3 catalyst, placing the Ir-CMK-3 catalyst in a 25mL polytetrafluoroethylene lining, adding 6mL of ethanol, adding 0.5mmol of quinoline substrate after ultrasonic dispersion for 5min, adding 50 μ L of internal standard anisole, adding magnetons, placing the lining in a high-pressure reaction kettle, sealing the reaction kettle, replacing internal gas with 2MPa hydrogen for three times, filling 2MPa hydrogen, heating the internal gas to 100 ℃, reacting for 40 min, placing the reaction kettle in a water bath for cooling after the reaction is finished, taking out reaction liquid for gas chromatography analysis after the reaction kettle is cooled to room temperature, and completely converting quinoline into tetrahydroquinoline after 40 min. Its TOF value at 10 min is about 7000h-1And the activity and the selectivity are superior to those reported in the prior literature.
Comparative example: preparation of mesoporous carbon supported monatomic iridium metal catalyst
(1) 0.2mg of iridium acetylacetonate in a 25mL single-neck flask was weighed, 5mL of acetone was added, and the mixture was stirred for 15 minutes. 100mg of CMK-3 was weighed out and added to the solution, stirred at 400r/min for 6 hours, and then rotary evaporated at 30 ℃ and 100rpm for 15 minutes.
(2) Putting the solid powder obtained by rotary evaporation in the step (1) into a porcelain boat, and carrying out pyrolysis in a tube furnace. In an argon atmosphere, heating to 600 ℃ at a heating rate of 5 ℃/min, keeping for 2h, and then naturally cooling to room temperature to obtain the mesoporous carbon supported monatomic iridium metal catalyst Ir-CMK-3.
The spherical aberration corrected high-angle annular dark field image of the catalyst prepared in this example is shown in fig. 5, and it can be seen that small bright spots in the image represent iridium atoms.
The mesoporous carbon supported monatomic iridium metal catalyst is applied to the hydrogenation reaction of quinoline, and the specific implementation steps are as follows: weighing 50mg of Ir-CMK-3 catalyst, placing the Ir-CMK-3 catalyst in a 25mL polytetrafluoroethylene lining, adding 6mL of ethanol, adding 0.5mmol of quinoline substrate after ultrasonic dispersion for 5min, adding 50 μ L of internal standard anisole, adding magnetons, placing the lining in a high-pressure reaction kettle, sealing the reaction kettle, replacing internal gas with 2MPa hydrogen for three times, filling 2MPa hydrogen, heating the internal gas to 100 ℃, reacting for 40 min, after the reaction is finished, placing in a water bath for cooling, and taking out reaction liquid for gas chromatography analysis after the reaction kettle is cooled to room temperature. The TOF value at 10 minutes is 3000h-1Lower than the catalyst of example 1 in which the monoatomic compound coexists with particles.
Example 2 preparation and application of activated carbon-supported monatomic and particulate synergistic ruthenium Metal catalysts
The preparation of the activated carbon supported monatomic and particulate synergistic ruthenium metal catalyst was performed as follows
(1) 10mg of ruthenium acetylacetonate in a 25mL single-neck flask was weighed, 5mL of acetone was added, and the mixture was stirred for 15 minutes. 100mg of activated carbon (Vulcan XC-72R Active carbon, commercially available from Cabot) was weighed out and added to the solution, stirred at 400R/min for 6 hours, and then rotary evaporated at 30 ℃ and 100rpm for 15 minutes.
(2) Putting the solid powder obtained by rotary evaporation in the step (1) into a porcelain boat, and carrying out pyrolysis in a tube furnace. In an argon atmosphere, heating to 500 ℃ at a heating rate of 5 ℃/min, keeping for 2h, and then naturally cooling to room temperature to obtain the ruthenium metal catalyst Ru-C with the load of 3 wt% and the coordination of the active carbon-loaded single atom and the particles.
The ruthenium metal catalyst with the synergy of the single atom and the particles loaded by the active carbon is applied to the hydrogenation reaction of phenylacetaldehyde, and the specific implementation steps are as follows: weighing 5.0mg of Ru-C catalyst, placing the catalyst in a 25mL reaction bottle, adding 5mL of ethanol, adding 0.5mmol of phenylacetaldehyde substrate after ultrasonic dispersion for 5min, adding 50 μ L of internal standard anisole, adding magnetons, sealing the reaction bottle, replacing internal gas with a hydrogen balloon for 20min, reacting at 25 ℃ under normal pressure of hydrogen for 1h, taking out reaction liquid after the reaction is finished, and performing gas chromatography analysis, wherein the result shows that the reaction is completely converted.
Example 3 preparation and use of a mesoporous silicon-supported monatomic and particulate synergistic Palladium Metal catalyst with SBA-15 preparation of an activated carbon-supported monatomic and particulate synergistic ruthenium Metal catalyst according to the following procedure
(1) 8mg of palladium acetylacetonate was weighed into a 25mL single-necked flask, and 5mL of acetone was added and stirred for 15 minutes. 100mg of SBA-15 was weighed out and added to the above solution, stirred at 400r/min for 6 hours, and then rotary evaporated at 30 ℃ and 100rpm for 15 minutes.
(2) Putting the solid powder obtained by rotary evaporation in the step (1) into a porcelain boat, and carrying out pyrolysis in a tube furnace. In argon atmosphere, raising the temperature to 700 ℃ at the heating rate of 5 ℃/min and keeping the temperature for 2h, and then naturally cooling the temperature to room temperature to obtain the palladium metal catalyst Pd-SBA-15 with the loading of 2.5 wt% of SBA-15 loaded monoatomic and particle synergetic.
The palladium metal catalyst with the synergy of the SBA-15 loaded monoatomic and particle is applied to the hydrogenation reaction of nitrobenzene, and the specific implementation steps are as follows: weighing 5.0mg of Pd-SBA-15 catalyst, placing the catalyst in a lining of 25mL, adding 5mL of ethanol, adding 2mmol of nitrobenzene after ultrasonic dispersion for 5min, adding 50 μ L of internal standard anisole, adding magnetons, placing the lining in a high-pressure reaction kettle, sealing the reaction kettle, replacing the internal gas with 2MPa hydrogen for three times, filling 2MPa hydrogen, heating the reaction kettle to 100 ℃, reacting for 20 minutes, placing the reaction kettle in a water bath for cooling after the reaction is finished, taking out the reaction liquid after the reaction kettle is cooled to room temperature, and performing gas chromatography analysis, wherein the result shows that the reaction is completely converted.
Example 4 preparation and application of mesoporous carbon supported monatomic and particulate synergistic platinum Metal catalysts
Preparing a mesoporous carbon supported monatomic and particle coordinated platinum metal catalyst according to the following steps:
(1) a25 mL single-necked flask containing 4mg of platinum acetylacetonate was weighed, and 5mL of water was added thereto and stirred for 15 minutes. 100mg of CMK-3 was weighed out and added to the solution, stirred at 400r/min for 6 hours, and then rotary evaporated at 60 ℃ and 200rpm for 20 minutes.
(2) Putting the solid powder obtained by rotary evaporation in the step (1) into a porcelain boat, and carrying out pyrolysis in a tube furnace. In an argon atmosphere, raising the temperature to 550 ℃ at a heating rate of 5 ℃/min and keeping the temperature for 2h, and then naturally cooling to room temperature to obtain the iridium metal catalyst Pt-CMK-3 with the loading of 2 wt% and the synergy of the mesoporous carbon loaded monoatomic particles and particles.
The mesoporous carbon supported monatomic and particle synergistic platinum metal catalyst is applied to the hydrogenation reaction of benzaldehyde, and the specific implementation steps are as follows: weighing 5.0mg of Pt-CMK-3 catalyst, placing the Pt-CMK-3 catalyst in a 25mL polytetrafluoroethylene lining, adding 6mL of ethanol, adding 0.5mmol of benzaldehyde substrate after ultrasonic dispersion for 5min, adding 50 μ L of internal standard anisole, adding magnetons, placing the lining in a high-pressure reaction kettle, sealing the reaction kettle, replacing internal gas with 2MPa hydrogen for three times, filling 0.5MPa hydrogen, heating the mixture to 80 ℃, reacting for 40 min, placing the mixture in a water bath for cooling after the reaction is finished, taking out reaction liquid after the reaction kettle is cooled to room temperature, performing gas chromatography analysis, and measuring the TOF value of the reaction liquid. The result was that the conversion of quinoline to tetrahydroquinoline was complete after 40 minutes. Its TOF value at 10 min is about 7000h-1And the activity and the selectivity are superior to those reported in the prior literature.
The above description of the embodiments is merely provided to aid in understanding the methods and core techniques of the present invention, and is not intended to limit the scope of the invention. Any modification, replacement, improvement or the like within the principles of the present application will be apparent to those skilled in the art and are within the scope of the present application.
Claims (10)
1. A metal catalyst, characterized by: the metal is uniformly loaded on the carrier in the form of coexistence of the monoatomic metal and the nanoparticle.
2. The metal catalyst according to claim 1, characterized in that: the metal is at least one of Ir, Ru, Rh, Pd, Co and Pt; and/or the presence of a gas in the gas,
the pore diameter of the carrier is 0.5-10 nm, and the specific surface area is 200-1500 m2(ii)/g; and/or the presence of a gas in the gas,
the carrier is any one of mesoporous carbon, mesoporous molecular sieve and active carbon; and/or the presence of a gas in the gas,
the loading amount of the metal catalyst is 0.1-10% by mass percentage.
3. The metal catalyst according to claim 1 or 2, characterized in that: the particle size of the nano-particles is 0.5-5 nm.
4. A method for preparing the metal catalyst of any one of claims 1 to 3, comprising the steps of:
(1) dipping the carrier in a solution consisting of metal salt of the metal and a solvent, and removing the solvent after dipping to obtain a metal catalyst precursor;
(2) and pyrolyzing the metal catalyst precursor to obtain the single-atom and particle synergistic supported metal catalyst.
5. The method of claim 4, wherein: in the step (1), the metal salt exists in the form of at least one of nitrate, sulfate, hydrochloride, acetylacetonate and acetate;
the solvent is at least one of ethanol, methanol, acetone, carbon tetrachloride and water;
in the solution composed of the metal salt and the solvent, the concentration of the metal salt is 0.1-10 mmol/L.
6. The production method according to claim 4 or 5, characterized in that: in the step (1), in an impregnation system consisting of the metal salt, the solvent and the carrier, the concentration of the carrier is 10-500 mg/mL.
7. The production method according to any one of claims 4 to 6, characterized in that: in the step (1), the impregnation is carried out under stirring conditions; the stirring speed is 100-1000 rpm, and the time is 0.5-24 h; and/or the presence of a gas in the gas,
in the step (1), the solvent removal is carried out in a rotary evaporation mode; the rotary evaporation temperature is 20-80 ℃, and the time is 5-30 min.
8. The production method according to any one of claims 4 to 7, characterized in that: in the step (2), the pyrolysis is performed under any one or more of nitrogen, argon and hydrogen; and/or the presence of a gas in the gas,
in the step (2), the heating rate of the pyrolysis is 1-5 ℃/min, the temperature is 200-1000 ℃, and the time is 1-4 hours.
9. Use of the metal catalyst of any one of claims 1 to 3 as a catalyst for catalyzing the hydrogenation of a quinoline-based compound, an aromatic nitro-based compound, an aromatic aldehyde or a carbonyl-based compound.
10. Use according to claim 9, characterized in that: the hydrogenation reaction is carried out in a solvent; the solvent is at least one of tetrahydrofuran, methanol, ethanol, toluene, acetonitrile and water; and/or the presence of a gas in the gas,
in the hydrogenation reaction, the dosage ratio of the compound, the solvent, hydrogen and the metal catalyst is 0.5-3 mmol: 3-10 mL: 0.1-4 MPa: 5-20 mg; and/or the presence of a gas in the gas,
in the hydrogenation reaction, the hydrogenation temperature is 20-140 ℃ and the time is 5-240 minutes.
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