CN115850042B - Method for preparing 2-pentanone by using platinum-based catalyst for 2-methyl furan hydrogenation - Google Patents
Method for preparing 2-pentanone by using platinum-based catalyst for 2-methyl furan hydrogenation Download PDFInfo
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- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 title claims abstract description 104
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 97
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 title claims abstract description 90
- 239000003054 catalyst Substances 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 42
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 41
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 94
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- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
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- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
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- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000405119 Virga Species 0.000 description 1
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- 239000003430 antimalarial agent Substances 0.000 description 1
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- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
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- KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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Abstract
The method for preparing 2-pentanone by using the platinum-based catalyst for 2-methyl furan hydrogenation has the characteristics of orderly and controllable multiphase flow, high mixing efficiency, accurate and controllable reaction parameters, good reaction repeatability, high degree of integrated automation and the like, and effectively solves the problems of long catalyst use time, low selectivity, operators dependent methods, uneven mixing and the like in the traditional impregnation method. And secondly, the method screens different amounts of solvents and reaction temperatures, determines the solvent dosage and the optimal reaction temperature, prepares the platinum-carbon catalyst, can ensure that the conversion rate of 2-pentanone prepared by 2-methyl furan hydrogenation can reach 88 percent, the selectivity of 2-pentanone is 79 percent, and the selectivity of 2-pentanone prepared by using the platinum-based catalyst prepared by using an impregnation method to 2-methyl furan hydrogenation is 25 percent, and the catalytic efficiency can be improved by nearly 50 percent compared with that of the impregnation method. The mechanized operation can avoid human errors, so that the result is easier to repeat, and the production efficiency is improved.
Description
Technical Field
The invention belongs to the technical field of biomass energy catalysis and continuous flow preparation, and particularly relates to a preparation method of a platinum-based catalyst for preparing 2-pentanone by hydrogenating biomass derivative 2-methyl furan, wherein the catalyst takes active carbon as a carrier, platinum is taken as a main active ingredient, the production efficiency of the catalyst is improved and the efficiency is ensured by using a continuous flow preparation method through debugging of different amounts of solvents and temperatures, the 2-pentanone can be effectively catalyzed by the catalyst, the continuous flow preparation method is efficient and simple, continuous mass production can be realized, the artificial error is reduced, and the catalyst has a large application value.
Background
Continuous flow reactors (Continuous flow reactor, CFR) are a novel technique in which reactions occur in channels with internal diameters ranging from a few microns to a few millimeters. In chemical engineering, micro-continuous flow devices can play a unique role in controlling critical reaction parameters due to the small size of the reactor. The continuous flow reactor has a plurality of advantages, high mass and heat transfer efficiency, accurate control of reaction temperature, pressure and time, easier realization of integration and automation, and improved reaction efficiency, thus receiving attention of vast researchers.
Lignocellulosic biomass is a rich and renewable carbon resource that is expected to replace traditional non-renewable fossil resources in chemical and fuel production to reduce serious dependence on fossil resources and reduce the associated environmental impact. Lignin, cellulose and hemicellulose are all derived from lignocellulosic biomass, which can be depolymerized into various platform compounds that can be further upgraded into high value chemicals and fuels.
2-methyl furan is one of the most potential biomass-based platform compounds, an important chemical intermediate, can be used as a solvent and a raw material, and is widely applied to the production of antimalarial drugs (chloroquine), pyrethroid pesticides, essence and spice, nitrogen and sulfur functionalized heterocycle and functional group substituted aliphatic compounds. In addition, 2-methylfuran can be converted into a number of derivatives and downstream products, such as: 2-methylfuran can also be hydrogenated to 2-methyltetrahydrofuran by c=c, or to C5 alcohols by hydrogenolysis of c—o bonds.
2-pentanone is an excellent dewaxing agent for lubricating oils, and is also used as a solvent for nitrolacquers, synthetic resin coatings, and as an intermediate and extractant for organic synthesis. In addition, 2-pentanone can be used for organic and medical synthesis intermediates and solvents, and can be used for synthesizing vasodilator Virga. The 2-pentanone can be prepared by dehydrogenation of 2-pentanol or co-heating of butyrylacetic acid ethyl ester with water. However, the process uses a large amount of organic solvents and inorganic matters to generate three wastes, which not only causes high cost, but also causes environmental problems. Chinese patent CN106478386A discloses a method for preparing 2-pentanone from ethanol, which has the advantages of wide raw material sources, simple process, but poor catalytic effect, and the selectivity of 2-pentanone is only 36.8%. Aiming at the problems, a new method for preparing 2-pentanone is developed, and the improvement of the conversion efficiency and the selectivity of the target product is imperative.
Disclosure of Invention
In order to solve the technical problems, the invention provides a preparation method of a platinum-based catalyst for preparing 2-pentanone by hydrogenating 2-methyl furan, which is simple and efficient and can be used for one-step continuous production. By using a continuous flow method, a high-activity catalyst is simply and efficiently prepared by screening the amount of the solvent and the reaction temperature, the conversion rate of 2-methyl furan can reach 88 percent and the selectivity of amyl alcohol is 79 percent under the reaction condition that the reaction temperature is 200 ℃ and the hydrogen pressure is 1 MPa. Meanwhile, the method can prepare the high-activity catalyst in one step, simplify the reaction steps, save the reaction time, and greatly improve the production efficiency in continuous production.
In order to solve the technical problems of the invention, the technical proposal is as follows: a method for preparing 2-pentanone by hydrogenation of 2-methylfuran by using a platinum-based catalyst, wherein the reaction for preparing 2-pentanone by hydrogenation of 2-methylfuran is carried out in an autoclave provided with a thermal conductivity detector, and the prepared platinum-based catalyst, 2-methylfuran and isopropanol are added into the autoclave to react to obtain 2-pentanone;
the preparation method of the platinum-based catalyst comprises the following steps: preparing a platinum-based catalyst using a continuous flow device; the continuous flow device consists of a peristaltic pump, a magnetic stirrer, a Teflon pipeline, a reaction device and a collecting device; the inlet end pipeline of the peristaltic pump is led into the container, the outlet end pipeline of the peristaltic pump is connected with a section of Teflon pipeline, the Teflon pipeline is fixed in the reaction device, and finally the outlet end of the Teflon pipeline is fixed above the collecting device; the method comprises the following specific steps:
(1) Using ethylene glycol, to which an appropriate amount of chloroplatinic acid (H 2 PtCl 6 ·6H 2 O) solid, ultrasonic, and is prepared into H 2 PtCl 6 ·6H 2 An O ethylene glycol solution;
(2) Adding activated carbon into a container, adding appropriate amount of ethylene glycol, appropriate amount of sodium hydroxide solution and appropriate amount of ultrapure water, and collecting appropriate amount of H prepared in step (1) 2 PtCl 6 ·6H 2 Adding the O ethylene glycol solution into the mixture to perform ultrasonic dispersion;
(3) The temperature of the reaction device is 160 ℃;
(4) And (5) placing the collected catalyst in a vacuum drying oven for drying.
Preferably, the mass content Pt of Pt in the chloroplatinic acid in the step (1) is more than or equal to 37.5 percent, and the ultrasonic frequency is 40KHz.
Preferably, the reaction for preparing 2-pentanone by hydrogenating 2-methyl furan is carried out in an autoclave provided with a thermal conductivity detector, a certain amount of 2-methyl furan, a solvent and a platinum-based catalyst are added into the autoclave, and the autoclave is sealed; purging the reaction kettle with 2MPa hydrogen for 3 times to remove air in the reaction kettle, filling 1MPa hydrogen again, reacting at 120-220 ℃ for 3h, cooling, releasing pressure, opening the kettle, filtering, and detecting by gas chromatography.
Preferably, the collecting device is a beaker, the container is a beaker, the Teflon pipeline with one length is connected to the outlet section of the peristaltic pump, the Teflon pipeline is circularly wound, and the fixing disc is suspended in the reaction device.
Preferably, 990mg of activated carbon is weighed into a beaker, 80ml of ethylene glycol, and 20ml of NaOH solution are added, and 1.4ml of prepared H is measured 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the above-mentioned materials into the above-mentioned material, and making ultrasonic treatment for 20min; placing the beaker into a continuous flow device, opening a reaction device switch, regulating a peristaltic pump to set the flow rate (50 ml/min), starting the pump switch after the temperature of the reaction device reaches 160 ℃, waiting for 15 minutes, collecting the solution in the beaker, stirring overnight, and carrying out suction filtration. And finally, placing the solid obtained after suction filtration in a culture dish, drying in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and preserving after the completion of the drying.
Preferably, the method comprises the following steps:
(1) Using ethylene glycol, to which an appropriate amount of chloroplatinic acid (H 2 PtCl 6 ·6H 2 O) solid, ultrasonic for 30min to prepare H 2 PtCl 6 ·6H 2 O-glycol (20 mg H per 1ml glycol) 2 PtCl 6 ·6H 2 O; sealing and preserving at low temperature;
(2) Adding a proper amount of sodium hydroxide (NaOH) solid into ultrapure water, and stirring to prepare an NaOH aqueous solution;
(3) Weighing 100mg of carbon carrier active carbon, adding into a beaker, adding a proper amount of glycol, and taking a proper amount of H prepared in the step (1) 2 PtCl 6 ·6H 2 Adding the O ethylene glycol solution and a proper amount of NaOH aqueous solution prepared in the step (2) into the mixture, performing ultrasonic dispersion, placing the mixture under a peristaltic pump, introducing a pipeline, opening a reaction device, introducing a sample after the temperature reaches the reaction temperature, waiting for a period of time, and collecting the sample by using a beaker;
(4) And (5) carrying out suction filtration on the collected reaction liquid, then placing the reaction liquid in a vacuum drying oven for drying for 12 hours, and sealing and preserving the reaction liquid after the completion of the drying.
Preferably, 990mg of activated carbon is weighed into a beaker, 80ml of ethylene glycol, and 20ml of NaOH solution are added, and 1.4ml of prepared H is measured 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the above-mentioned materials into the above-mentioned material, and making ultrasonic treatment for 20min; placing the beaker into a continuous flow device, opening a switch of the reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting the pump switch after the temperature of an oil bath reaches 160 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, suction filtering, washing the reaction solution, finally placing the solid obtained after suction filtering into a culture dish, drying in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing after the completion of the drying.
Preferably, (1) the continuous flow device consists of peristaltic pump, magnetic stirrer, multi-section Teflon tubing, reaction device, beaker. The inlet end pipeline of the peristaltic pump is led into the beaker, the outlet end pipeline of the peristaltic pump is connected with a Teflon pipeline with proper length, the Teflon pipeline is a circular winding disc and is suspended in the device, and finally, the outlet end of the pipeline is fixed above the beaker.
(2) The ethylene glycol is used, and a proper amount of chloroplatinic acid (H) is added 2 PtCl 6 ·6H 2 O) solid, ultrasonic for 30min to prepare H 2 PtCl 6 ·6H 2 O ethylene glycol solution, sealing and preserving at low temperature;
(3) Adding a proper amount of sodium hydroxide (NaOH) solid into ultrapure water, and stirring to prepare an NaOH aqueous solution;
(3) Weighing 100mg of carbon carrier active carbon, adding into a beaker, adding a proper amount of glycol, and taking a proper amount of H prepared in the step (1) 2 PtCl 6 ·6H 2 Adding the O ethylene glycol solution and a proper amount of NaOH aqueous solution prepared in the step (2) into the mixture for ultrasonic dispersion
(4) Placing the beaker into a continuous flow device, opening a switch of the reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting the pump switch after the temperature of an oil bath reaches 160 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, suction filtering, washing the reaction solution, finally placing the solid obtained after suction filtering into a culture dish, drying in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing after the completion of the drying.
(5) 3.4mmol of 2-methyl furan, 8ml of isopropanol and 50mg of platinum-based catalyst are added into a reaction kettle, and the reaction kettle is well sealed; after the hydrogen with the pressure of 2MPa is replaced for three times, the reaction kettle is filled with hydrogen with the pressure of 1MPa; the reaction temperature is 200 ℃; the reaction time is 3 hours, after the reaction is finished, the temperature is reduced, the pressure is relieved, the kettle is opened, the filtration is carried out, and the gas chromatography is used for detection;
the beneficial effects of the invention are as follows:
the invention provides a continuous flow preparation method of a platinum-based catalyst, which is simpler and more efficient and can be produced continuously in one step compared with the time length of an impregnation method, and the problems of uneven mixing and the like which depend on the operation method of operators. Firstly, the method adopts a pipe diameter of a few millimeters, the specific surface area of the reaction liquid is greatly increased, mass and heat transfer can be fast carried out, and the reaction liquid can be well mixed uniformly. Next, the method screens different amounts of solvent and reaction temperature, when the solvent dosage is 100ml, the reaction temperature is 160 ℃, 100ml of solution is corresponding to each 990mg of active carbon, wherein 80ml of glycol and 20ml of NaOH solution, H 2 PtCl 6 ·6H 2 The ratio of the O solution to the catalyst is: every 990mg of active carbon corresponds to 1.4ml of H 2 PtCl 6 ·6H 2 The O solution is optimal, the conversion rate of 2-pentanone prepared by hydrogenating 2-methyl furan can reach 88 percent, the selectivity of 2-pentanone is 79 percent, and the conversion rate of 2-pentanone prepared by hydrogenating 2-methyl furan is 98 percent by using a platinum-based catalyst prepared by an impregnation methodThe selectivity to 2-pentanone was 25% and only by-product. (for a specific method of impregnation, refer to patent CN 113999088B). The catalytic efficiency is improved by nearly 50%. The particle size of the platinum-based catalyst prepared by the method was stabilized at about 3.7nm in terms of TEM and particle size distribution. The platinum-based catalyst prepared by the impregnation method has agglomeration phenomenon and different particle sizes. The mechanized operation can avoid human error, so that the result is easier to repeat, the production efficiency is greatly improved, and a new way is provided for preparing 2-pentanone by catalytic hydrogenation of furan derivatives. In addition, the raw materials used in the invention are renewable biomass derivatives, the raw materials are abundant in sources and low in cost and easy to obtain, the renewable biomass derivatives are expected to replace traditional nonrenewable fossil resources in the production of chemicals and fuels, are environment-friendly, and have wider application potential in industrial production. The general reaction formula of the invention is:
drawings
FIG. 1 is a schematic diagram of a continuous flow apparatus
FIG. 2 is a diagram showing the reaction mechanism of hydrogenolysis of 2-methylfuran to 2-pentanone
FIG. 3 TEM image and particle size distribution of a continuous flow prepared platinum-based catalyst
FIG. 4 TEM image and particle size distribution of a platinum-based catalyst prepared by the impregnation method
FIG. 5 effect of different temperatures on distribution of 2-methylfuran hydrogenation product
Wherein fig. 1: peristaltic pump-1; peristaltic pump controller-2; reaction liquid-3; teflon tube-4; reaction liquid-5; reactor controller-6
Detailed Description
The present invention will be described in further detail with reference to specific examples, which are only for illustrating the present invention, but the present invention is not limited to the following examples.
Example 1
(1) The continuous flow device consists of a peristaltic pump, a magnetic stirrer, a multi-section Teflon pipeline, a reaction device and a beaker. The inlet end pipeline of the peristaltic pump is led into the beaker, the outlet end pipeline of the peristaltic pump is connected with a Teflon pipeline with proper length, the Teflon pipeline is a circular winding disc and is suspended in the reaction device, and finally, the outlet end of the pipeline is fixed above the beaker; a Teflon pipeline with the pipe diameter of 3 mm is adopted;
(2) 1g of chloroplatinic acid is taken and dissolved in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for standby;
(3) Weighing 990mg of active carbon, adding 80ml of ethylene glycol and 20ml of NaOH solution into a beaker, and weighing 1.4ml of prepared H 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the above-mentioned materials into the above-mentioned material, and making ultrasonic treatment for 20min; placing the beaker into a continuous flow device, opening a switch of the reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting the pump switch after the temperature of an oil bath reaches 160 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, suction filtering, washing the reaction solution, finally placing the solid obtained after suction filtering into a culture dish, drying in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing after the completion of the drying.
The catalyst was named 1% pt/C (V (EG: naOH solution) =4). The particle size was 3.7.+ -. 0.28nm.
Comparative example 1-1 catalyst preparation
(1) 1g of chloroplatinic acid is taken and dissolved in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for standby;
(2) Weighing 990mg of active carbon, adding 50ml of glycol and 50ml of NaOH solution into a beaker, and weighing 1.4ml of prepared H 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the above-mentioned materials into the above-mentioned material, and making ultrasonic treatment for 20min; placing the beaker into a continuous flow device, opening a switch of the reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting the pump switch after the temperature of an oil bath reaches 160 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, suction-filtering, washing the reaction solution, finally placing the solid obtained after suction-filtering into a culture dish, drying in a vacuum drying oven at 80 ℃ for 12 hours, and formingSealing and preserving after bundling;
the catalyst was named 1% pt/C (V (EG: naOH solution) =1).
Comparative examples 1-2 catalyst preparation
(1) 1g of chloroplatinic acid is taken and dissolved in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for standby;
(2) Weighing 990mg of active carbon, adding 60ml of glycol and 40ml of NaOH solution into a beaker, and weighing 1.4ml of prepared H 2 PtCl 6 ·6H 2 OO glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the above-mentioned materials into the above-mentioned material, and making ultrasonic treatment for 20min; placing the beaker into a continuous flow device, opening a switch of the reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting the pump switch after the temperature of an oil bath reaches 160 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, suction-filtering, washing the reaction solution, finally placing the solid obtained after suction-filtering into a culture dish, drying in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing after the completion of the drying;
the catalyst was named 1% pt/C (V (EG: naOH solution) =1.5).
Comparative examples 1-3 catalyst preparation
(1) 1g of chloroplatinic acid is taken and dissolved in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for standby;
(2) 990mg of activated carbon was weighed into a beaker, 70ml of ethylene glycol, and 30ml of NaOH solution were added, and 1.4ml of prepared H was measured 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the above-mentioned materials into the above-mentioned material, and making ultrasonic treatment for 20min; placing the beaker into a continuous flow device, opening a switch of the reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting the pump switch after the temperature of an oil bath reaches 160 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, suction-filtering, washing the reaction solution, finally placing the solid obtained after suction-filtering into a culture dish, drying in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing after the completion of the drying;
the catalyst was named 1% pt/C (V (EG: naOH solution) =2.3).
Comparative examples 1-4 catalyst preparation
(1) 1g of chloroplatinic acid is taken and dissolved in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for standby;
(2) 990mg of activated carbon are weighed into a beaker, 90ml of ethylene glycol and 10ml of NaOH solution are added, and 1.4ml of prepared H is measured 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the above-mentioned materials into the above-mentioned material, and making ultrasonic treatment for 20min; placing the beaker into a continuous flow device, opening a switch of the reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting the pump switch after the temperature of an oil bath reaches 160 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, suction-filtering, washing the reaction solution, finally placing the solid obtained after suction-filtering into a culture dish, drying in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing after the completion of the drying;
the catalyst was named 1% pt/C (V (EG: naOH solution) =9).
Comparative examples 1-5 catalyst preparation
(1) 1g of chloroplatinic acid is taken and dissolved in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for standby;
(2) Weighing 990mg of active carbon, adding 50ml of glycol and 50ml of NaOH solution into a beaker, and weighing 1.4ml of prepared H 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the above-mentioned materials into the above-mentioned material, and making ultrasonic treatment for 20min; placing the beaker into a continuous flow device, opening a switch of the reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting the pump switch after the temperature of an oil bath reaches 150 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, suction-filtering, washing the reaction solution, finally placing the solid obtained after suction-filtering into a culture dish, drying in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing after the completion of the drying;
the catalyst was designated 1% Pt/C (150 ℃).
Comparative examples 1-6 catalyst preparation
(1) 1g of chloroplatinic acid is taken and dissolved in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for standby;
(2) Weighing 990mg of active carbon, adding 50ml of glycol and 50ml of NaOH solution into a beaker, and weighing 1.4ml of prepared H 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the above-mentioned materials into the above-mentioned material, and making ultrasonic treatment for 20min; placing the beaker into a continuous flow device, opening a switch of the reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting the pump switch after the temperature of an oil bath reaches 170 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, suction-filtering, washing the reaction solution, finally placing the solid obtained after suction-filtering into a culture dish, drying in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing after the completion of the drying;
the catalyst was designated 1% Pt/C (170 ℃).
Example 2
(1) The continuous flow device consists of a peristaltic pump, a magnetic stirrer, a multi-section Teflon pipeline, a reaction device and a beaker. The inlet end pipeline of the peristaltic pump is led into the beaker, the outlet end pipeline of the peristaltic pump is connected with a Teflon pipeline with proper length, the Teflon pipeline is a circular winding disc and is suspended in the reaction device, and finally, the outlet end of the pipeline is fixed above the beaker;
(2) 1g of chloroplatinic acid is taken and dissolved in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for standby;
(3) 1.98g of activated carbon is weighed into a beaker, 160ml of glycol and 40ml of NaOH solution are added, and 2.8ml of prepared H is measured 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the above-mentioned materials into the above-mentioned material, and making ultrasonic treatment for 20min; placing the beaker into a continuous flow device, opening a switch of the reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting the pump switch after the temperature of an oil bath reaches 160 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, filtering, washing the reaction solution, finally placing the solid obtained by the filtering into a culture dish, and placing the culture dish into a vacuum drying oven at 80 DEG CDrying for 12h, and sealing and storing after finishing.
Example 3 catalyst ICP test
Example 1 the platinum-based catalysts prepared in comparative examples 1-1, 1-2, 1-3, 1-4, 1-5, and 1-6 were weighed, dissolved in aqua regia, diluted to a constant volume, and tested by inductively coupled plasma emission spectrometer Inductively Coupled Plasma Optical Emission Spectrometer (ICP-OES), and the results are shown in table 1.
TABLE 1 catalyst ICP test results
According to the above results, the catalysts prepared in example 1 and example 2 have a loading rate of more than 95%, while the comparative examples 1-1, 1-2, 1-3, 1-4, 1-5, and 1-6 have a loading rate of 50% to 90%, and have a poor loading effect, and for better follow-up impregnation (see patent CN113999088B for a specific method of impregnation), example 1 and example 2 can be used for hydrogenation of 2-methylfuran to prepare 2-pentanone.
Example 4 2 test of reactivity of hydrogenation of methyl Furan to 2-pentanone
The hydrogenation reaction of 2-methylfuran to 2-pentanone was carried out in an autoclave equipped with a thermal conductivity detector. 50mg of the prepared platinum-based catalyst, 3.4mmol of 2-methylfuran and 8ml of isopropanol are added into a reaction kettle, the reaction kettle is purged for 3 times by using hydrogen of 2MPa before the reaction to remove air in the reaction kettle, then 1MPa of hydrogen is filled, the reaction temperature is 200 ℃, the reaction time is 3 hours, after the reaction is finished, the reaction kettle is put into ice water and cooled to room temperature rapidly, the catalyst and the reaction liquid are separated, and the composition of the reaction liquid is detected by using gas chromatography, so that a reaction result is obtained.
The test results are shown in Table 2.
Table 2 2-reactivity test for hydrogenation of methyl Furan to 2-pentanone
In order to better embody the superiority of the platinum-based catalyst prepared by a continuous flow method, the catalyst is used for testing the activity of preparing 2-pentanone by hydrogenating dimethyl furan. According to the experimental results of Table 2, the conversion of 2-methylfuran on the catalyst of example 1 had been 88%, with a 2-pentanone yield of 79%, which was increased by nearly 30% compared to the 2-pentanone yield (50%) obtained with 1% Pt/C prepared by impregnation. In addition, other comparison results show that the activity of preparing 2-pentanone by hydrogenating dimethyl furan is superior to that of the catalyst prepared by an impregnation method, although the loading rate is not reached.
Example 5 2 test of reactivity of hydrogenation of methyl Furan to 2-pentanone
The effect of temperature on 2-methylfuran hydrogenation to 2-pentanone was investigated: this example differs from example 4 in that the reaction temperature in the operating step is 120℃and the other processes are the same as in example 4.
Example 6 2 test of reactivity of hydrogenation of methyl Furan to 2-pentanone
The effect of temperature on 2-methylfuran hydrogenation to 2-pentanone was investigated: this example differs from example 4 in that the reaction temperature in the operating step was 140℃and the other processes were the same as in example 4.
Example 7 2 test of reactivity of hydrogenation of methyl Furan to 2-pentanone
The effect of temperature on 2-methylfuran hydrogenation to 2-pentanone was investigated: this example differs from example 4 in that the reaction temperature in the operating step is 160℃and the other processes are the same as in example 4.
Example 8 2 test of reactivity of hydrogenation of methyl Furan to 2-pentanone
The effect of temperature on 2-methylfuran hydrogenation to 2-pentanone was investigated: this example differs from example 4 in that the reaction temperature in the operating step is 180℃and the other processes are the same as in example 4.
Example 9 2 test of reactivity of hydrogenation of methyl Furan to 2-pentanone
The effect of temperature on 2-methylfuran hydrogenation to 2-pentanone was investigated: this example differs from example 4 in that the reaction temperature in the operating step is 220℃and the other processes are the same as in example 4.
According to FIG. 5, the effect of reaction temperature on product distribution is shown, the reaction product is mainly 2-pentanone, 2-methylfuran conversion increases with increasing temperature, and 2-pentanone yield reaches a maximum at 200 ℃.
According to the reaction result, the invention prepares a platinum-based catalyst by using a continuous flow method, and the catalyst with the highest loading rate is obtained by optimizing the use amount of the solvent, so that the catalyst is applied to the reaction of preparing 2-pentanone by 2-methyl furan hydrogenation, and the yield is obviously improved. The prepared particles are uniformly distributed and have smaller particle size. Compared with the prior process production line, the preparation process of the process line is simple, the mechanized operation can effectively avoid human errors, the required catalyst can be obtained in one step, and the production time is greatly shortened. The raw materials are renewable, the catalyst has high activity and mild reaction conditions, the energy consumption is reduced to a certain extent, the catalyst is environment-friendly, and the energy problem facing the world today can be effectively relieved. Therefore, the invention has wide application potential in industrial production.
The invention is not limited to the specific technical scheme described in the above embodiments, and all technical schemes formed by adopting equivalent substitution are the protection scope of the invention.
Claims (4)
1. A method for preparing 2-pentanone by using platinum-based catalyst for 2-methyl furan hydrogenation is characterized in that: the reaction for preparing 2-pentanone by hydrogenating 2-methylfuran is carried out in an autoclave equipped with a thermal conductivity detector, 50mg of 1wt.% Pt/C platinum-based catalyst, 3.4mmol of 2-methylfuran, 8ml of isopropanol are added to the autoclave; before the reaction, purging the reaction kettle with hydrogen of 2MPa for 3 times to remove air in the reaction kettle, and then filling hydrogen of 1MPa, wherein the reaction temperature is 200 ℃, and the reaction time is 3 hours to prepare 2-pentanone;
the 1wt.% Pt/C platinum-based catalyst preparation method: preparing a platinum-based catalyst using a continuous flow device; the continuous flow device consists of a peristaltic pump, a magnetic stirrer, a Teflon pipeline, a reaction device and a beaker; the inlet end pipeline of the peristaltic pump is led into the beaker, the outlet end pipeline of the peristaltic pump is connected with a Teflon pipeline with proper length, the Teflon pipeline is a circular winding disc and is suspended in the reaction device, and finally, the outlet end of the pipeline is fixed above the beaker; a Teflon pipeline with the pipe diameter of 3 mm is adopted;
the method comprises the following specific steps: weighing 990mg of active carbon, adding 80ml of ethylene glycol and 20ml of NaOH aqueous solution into a beaker, and weighing 1.4ml of prepared H 2 PtCl 6 ·6H 2 Adding O ethylene glycol solution into the solution, and performing ultrasonic treatment for 20min to obtain H 2 PtCl 6 ·6H 2 The O glycol solution contains 20mg H per 1ml solution 2 PtCl 6 ·6H 2 O; placing the beaker into a continuous flow device, opening a reaction device switch, regulating a peristaltic pump to set the flow speed to 20ml/min, starting the pump switch after the temperature of the reaction device reaches 160 ℃, waiting for 15 minutes, completely flowing out the solution, finally collecting the solution in the beaker, adding acid, stirring, pumping and filtering to wash the reaction solution, finally placing the solid obtained by pumping and filtering into a culture dish, drying in a vacuum drying box at 80 ℃ for 12 hours, and sealing and preserving after the completion of the drying; the catalyst particle size was 3.7.+ -. 0.28nm.
2. The method for preparing 2-pentanone by hydrogenation of 2-methyl furan using a platinum-based catalyst according to claim 1, characterized in that: h in specific steps of the preparation method of the platinum-based catalyst 2 PtCl 6 ·6H 2 And (5) preserving the O-glycol solution in a low-temperature sealing way.
3. The method for preparing 2-pentanone by hydrogenation of 2-methyl furan using a platinum-based catalyst according to claim 1, characterized in that: the preparation method of the platinum-based catalyst comprises the specific steps of adding a proper amount of sodium hydroxide NaOH solid into ultrapure water, and stirring to prepare a NaOH aqueous solution.
4. The method for preparing 2-pentanone by hydrogenation of 2-methyl furan using a platinum-based catalyst according to claim 1, characterized in that: in the preparation method of the platinum-based catalyst, a Teflon pipeline is suspended in a reactor through a thin iron wire fixing disc.
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