CN115850042A - Method for preparing 2-pentanone by hydrogenation of 2-methylfuran through platinum-based catalyst - Google Patents
Method for preparing 2-pentanone by hydrogenation of 2-methylfuran through platinum-based catalyst Download PDFInfo
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- CN115850042A CN115850042A CN202211671403.XA CN202211671403A CN115850042A CN 115850042 A CN115850042 A CN 115850042A CN 202211671403 A CN202211671403 A CN 202211671403A CN 115850042 A CN115850042 A CN 115850042A
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 119
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 title claims abstract description 114
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 title claims abstract description 106
- 239000003054 catalyst Substances 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 49
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 49
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 111
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- 239000000243 solution Substances 0.000 claims description 115
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 87
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- 230000001105 regulatory effect Effects 0.000 claims description 12
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- 239000001257 hydrogen Substances 0.000 claims description 11
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- FJSKXQVRKZTKSI-UHFFFAOYSA-N 2,3-dimethylfuran Chemical compound CC=1C=COC=1C FJSKXQVRKZTKSI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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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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- 230000002194 synthesizing effect Effects 0.000 description 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- LYCAIKOWRPUZTN-NMQOAUCRSA-N 1,2-dideuteriooxyethane Chemical compound [2H]OCCO[2H] LYCAIKOWRPUZTN-NMQOAUCRSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-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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- 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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- 125000000524 functional group Chemical group 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 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 hydrogenation of 2-methylfuran by using the platinum-based catalyst has the characteristics of ordered and controllable multiphase flow, high mixing efficiency, accurate and controllable reaction parameters, good reaction repeatability, high integration automation degree and the like, and effectively solves the problems of long time for preparing the catalyst by using a traditional impregnation method, low selectivity, operator-dependent manipulation, uneven mixing and the like. Secondly, the method screens solvents with different amounts and reaction temperatures, determines the solvent amount and the optimal reaction temperature, prepares the platinum-carbon catalyst, can ensure that the conversion rate of 2-pentanone prepared by hydrogenating 2-methylfuran can reach 88 percent, the selectivity of 2-pentanone is 79 percent, and uses the platinum-based catalyst prepared by the impregnation method, the selectivity of 2-pentanone prepared by hydrogenating 2-methylfuran is 25 percent, and the catalytic efficiency can be improved by nearly 50 percent compared with 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 method preparation, and particularly relates to a preparation method of a platinum-based catalyst for preparing 2-pentanone by hydrogenating biomass derivative 2-methylfuran, wherein the catalyst takes activated carbon as a carrier, platinum as a main active ingredient, the continuous flow preparation method is used for improving the production efficiency of the catalyst and ensuring the efficiency by debugging solvents with different amounts and temperatures, the 2-methylfuran can be effectively catalyzed by the catalyst to prepare the 2-pentanone, and the continuous flow preparation method is efficient and simple, can be used for continuous large-scale production, reduces manual errors and has a great application value.
Background
Continuous Flow Reactors (CFR) are a novel technique, the reaction taking place in channels with internal diameters from a few micrometers to a few millimeters. In chemical engineering, micro-continuous flow devices can provide unique control of key reaction parameters due to the small size of the reactor. The continuous flow reactor has many advantages, high mass and heat transfer efficiency, accurate control of reaction temperature, pressure and time, easy realization of integration and automation, and improved reaction efficiency, thus receiving attention of extensive researchers.
Lignocellulosic biomass is an abundant and renewable carbon resource that is expected to replace traditional non-renewable fossil resources in chemical and fuel production to mitigate severe dependence on fossil resources and associated environmental impacts. Lignin, cellulose and hemicellulose are all derived from lignocellulosic biomass and can be depolymerized into various platform compounds that can be further upgraded into high-value chemicals and fuels.
2-methylfuran is one of the most potential biomass-based platform compounds, is 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, essences and fragrances, nitrogen and sulfur functionalized heterocycles and functional group substituted aliphatic compounds. In addition, 2-methylfuran can be converted into a number of derivatives and downstream products, for example: 2-methylfuran can also be hydrogenated to produce 2-methyltetrahydrofuran by C = C hydrogenation, or to produce 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 intermediates and extractants for organic synthesis. In addition, the 2-pentanone can be used for synthesizing intermediates and solvents for organic and medical medicines, and can be used for synthesizing vasodilator drugs Virga. 2-pentanone can be prepared by dehydrogenation of 2-pentanol or by co-heating butyroacetate with water. However, the process uses a large amount of organic solvents and inorganic substances, which causes three wastes, not only high cost, but also environmental problems. Chinese patent CN106478386A discloses a method for preparing 2-pentanone from ethanol, which has wide raw material source and simple process, but the catalytic effect is not good enough, and the selectivity of 2-pentanone is only 36.8%. In view of the above problems, it is imperative to develop a new method for preparing 2-pentanone to improve the conversion efficiency and the selectivity of the target product.
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-methylfuran, which is simple and efficient and can be used for one-step and continuous production. A high-activity catalyst is simply and efficiently prepared by using a continuous flow method and screening the amount of a solvent and the reaction temperature, the conversion rate of 2-methylfuran can reach 88% and the selectivity of amyl alcohol is 79% under the reaction conditions that the reaction temperature is 200 ℃ and the hydrogen pressure is 1 MPa. Meanwhile, the method can prepare the high-activity catalyst by one step, simplify reaction steps, save reaction time and greatly improve production efficiency by continuous production.
In order to solve the technical problem of the invention, the technical proposal is as follows: a method for preparing 2-pentanone by hydrogenating 2-methylfuran by utilizing a platinum-based catalyst is characterized in that the reaction for preparing 2-pentanone by hydrogenating 2-methylfuran is carried out in an autoclave provided with a thermal conductivity detector, the prepared platinum-based catalyst, 2-methylfuran and isopropanol are added into the autoclave, and 2-pentanone is obtained through reaction;
the preparation method of the platinum-based catalyst comprises the following steps: preparing a platinum-based catalyst using a continuous flow apparatus; the continuous flow device consists of a peristaltic pump, a magnetic stirrer, a Teflon pipeline, a reaction device and a collection device; the inlet end pipeline of the peristaltic pump is introduced into the container, the outlet end pipe of the peristaltic pump is connected with a section of Teflon pipeline with a length, the section of 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, adding appropriate amount of chloroplatinic acid (H) 2 PtCl 6 ·6H 2 O) solid, ultrasonic treatment to prepare H 2 PtCl 6 ·6H 2 O ethylene glycol solution;
(2) Adding activated carbon into a container, adding a proper amount of glycol, a proper amount of sodium hydroxide solution and a proper amount of ultrapure water, and taking a proper amount of H prepared in the step (1) 2 PtCl 6 ·6H 2 Adding O glycol solution into the mixture to perform ultrasonic dispersion;
(3) The temperature of the reaction device is 160 ℃;
(4) And (5) drying the collected catalyst in a vacuum drying box.
Preferably, in the step (1), the Pt mass content in the chloroplatinic acid Pt is more than or equal to 37.5%, and the ultrasonic frequency is 40KHz.
Preferably, the reaction for preparing 2-pentanone by hydrogenating 2-methylfuran is carried out in an autoclave provided with a thermal conductivity detector, a certain amount of 2-methylfuran, a solvent and a platinum-based catalyst are added into the reaction kettle, and the reaction kettle is sealed after being filled with the solvent and the platinum-based catalyst; purging the reaction kettle with 2MPa hydrogen for 3 times to remove air in the reaction kettle, recharging 1MPa hydrogen, reacting at 120-220 deg.C for 3h, cooling, releasing pressure, opening the kettle, filtering, and detecting with gas chromatography.
Preferably, the collecting device is a beaker, the container is a beaker, the outlet section of the peristaltic pump is connected with a Teflon pipeline with a section of length, the Teflon pipeline is wound in a circular shape, and the fixed disk 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 activated carbon is measuredH 2 PtCl 6 ·6H 2 Oglycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the mixture into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump to set a flow rate (50 ml/min), starting the switch of the pump 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 the suction filtration into a culture dish, placing the culture dish into a vacuum drying oven at 80 ℃ for drying for 12 hours, and sealing and storing after the drying is finished.
Preferably, the method comprises the following steps:
(1) Using ethylene glycol, adding appropriate amount of chloroplatinic acid (H) 2 PtCl 6 ·6H 2 O) solid, and ultrasonic treatment is carried out for 30min to prepare H 2 PtCl 6 ·6H 2 Oethylene glycol (20 mg H per 1ml ethylene glycol) 2 PtCl 6 ·6H 2 O; sealing and storing 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 activated carbon, adding into a beaker, adding a proper amount of ethylene glycol, and taking a proper amount of H prepared in the step (1) 2 PtCl 6 ·6H 2 Adding O glycol solution and a proper amount of NaOH aqueous solution prepared in the step (2) into the O glycol solution for ultrasonic dispersion, placing the mixture under a peristaltic pump, guiding a pipeline, opening a reaction device, carrying out sample injection after the temperature reaches the reaction temperature, waiting for a period of time, and collecting the sample by using a beaker;
(4) And (4) carrying out suction filtration on the collected reaction solution, drying the reaction solution in a vacuum drying oven for 12 hours, and sealing and storing the reaction solution after 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 Oglycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the mixture into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating a peristaltic pump, setting a flow rate (20 ml/min), and after the temperature of an oil bath pan reaches 160 DEG CStarting a pump switch, waiting for 15 minutes, enabling the solution to flow out completely, collecting the solution in a beaker, adding acid, stirring, carrying out suction filtration on the washed reaction solution, placing the solid obtained after the suction filtration in a culture dish, placing the culture dish in a vacuum drying oven at 80 ℃ for drying for 12 hours, and sealing and storing the culture dish after the drying.
Preferably, the continuous flow device (1) consists of a peristaltic pump, a magnetic stirrer, a plurality of sections of Teflon pipelines, 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 a 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) Adding appropriate amount of chloroplatinic acid (H) into ethylene glycol 2 PtCl 6 ·6H 2 O) solid, and ultrasonic treatment is carried out for 30min to prepare H 2 PtCl 6 ·6H 2 O glycol solution, sealing and storing 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 activated carbon, adding into a beaker, adding a proper amount of ethylene glycol, and taking a proper amount of H prepared in the step (1) 2 PtCl 6 ·6H 2 Adding O 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 in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump, setting the flow rate (20 ml/min), starting the switch of the pump after the temperature of an oil bath pan reaches 160 ℃, waiting for 15 minutes, allowing the solution to completely flow out, finally collecting the solution in the beaker, adding acid, stirring, carrying out suction filtration to wash the reaction solution, finally placing the solid obtained after the suction filtration in a culture dish, placing the culture dish in a vacuum drying oven at 80 ℃ for drying for 12 hours, and sealing and storing after the reaction is finished.
(5) Adding 3.4mmol of 2-methylfuran, 8ml of isopropanol and 50mg of platinum-based catalyst into a reaction kettle, and packaging and sealing; after replacing the mixture with 2MPa hydrogen for three times, filling the reaction kettle with hydrogen with the pressure of 1MPa; the reaction temperature is 200 ℃; the reaction time is 3h, and after the reaction is finished, the temperature is reduced, the pressure is relieved, the kettle is opened, the reaction is filtered, and the gas chromatography is used for detection;
the invention has the following beneficial effects:
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 problems that an impregnation method is long in use time, and the method depends on the method of operators and is easy to mix unevenly. Firstly, the method adopts a pipe diameter of several millimeters, the specific surface area of the reaction liquid is greatly increased, the mass and heat transfer can be fast, and the reaction liquid can be well and uniformly mixed. Secondly, the method screens different amounts of solvent and reaction temperature, when the amount of the solvent is 100ml, the reaction temperature is 160 ℃, every 990mg of the activated carbon corresponds to 100ml of solution, 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 as follows: 1.4ml of H per 990mg of activated carbon 2 PtCl 6 ·6H 2 The O solution is the best, the conversion rate of preparing 2-pentanone by hydrogenating 2-methylfuran can reach 88%, and the selectivity of preparing 2-pentanone is 79%, while the conversion rate of preparing 2-pentanone by hydrogenating 2-methylfuran is 98% by using the platinum-based catalyst prepared by the immersion method, but the selectivity of preparing 2-pentanone by hydrogenating 2-methylfuran is 25%, and only is a byproduct. (for a specific method of the dipping method, refer to patent CN 113999088B). Catalytic efficiency is improved by nearly 50%. According to TEM and a particle size distribution diagram, the particle size of the platinum-based catalyst prepared by the method is stabilized to be about 3.7 nm. The platinum-based catalyst prepared by the impregnation method has agglomeration phenomenon and different particle sizes. The mechanized operation can avoid human errors, 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 by the invention are renewable biomass derivatives, are rich in raw material sources, cheap and easily available, are expected to replace the traditional non-renewable 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 as follows:
drawings
FIG. 1 is a schematic view of a continuous flow apparatus
FIG. 2 is a reaction scheme for hydrogenolysis of 2-methylfuran to 2-pentanone
FIG. 3 TEM image and particle size distribution of platinum-based catalyst prepared by continuous flow
FIG. 4 TEM image and particle size distribution of platinum-based catalyst prepared by impregnation method
FIG. 5 Effect of different temperatures on 2-methylfuran hydrogenation product distribution
Wherein, in the figure 1: a peristaltic pump-1; a peristaltic pump controller-2; reaction solution-3; teflon tube-4; reaction solution-5; reaction apparatus controller-6
Detailed Description
The present invention will be described in further detail with reference to specific examples, which are provided for illustrative purposes only and are not intended to limit the scope of the present invention.
Example 1
(1) The continuous flow device consists of a peristaltic pump, a magnetic stirrer, a plurality of sections of Teflon pipelines, a reaction device and a beaker. An inlet end pipeline of the peristaltic pump is led into the beaker, an outlet end pipeline of the peristaltic pump is connected with a Teflon pipeline with a proper length, the Teflon pipeline is a circular winding disc and is suspended in the reaction device, and finally, an outlet end of the pipeline is fixed above the beaker; a Teflon pipeline with the diameter of 3 mm is adopted;
(2) Dissolving 1g of chloroplatinic acid in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for later use;
(3) Weighing 990mg of active carbon in a beaker, adding 80ml of glycol and 20ml of NaOH solution, and measuring 1.4ml of prepared H 2 PtCl 6 ·6H 2 Oglycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the mixture into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump, setting the flow rate (20 ml/min), starting the switch of the pump after the temperature of an oil bath pan reaches 160 ℃, waiting for 15 minutes, allowing the solution to completely flow out, collecting the solution in the beaker, adding acid, stirring, carrying out suction filtration on the reaction solution, washing the reaction solution, placing the solid obtained after the suction filtration in a culture dish, and drying the solid in a vacuum drying oven at 80 DEG CDrying for 12h, and sealing for storage.
The catalyst was named as 1% Pt/C (V (EG: naOH solution) = 4). The particle size was 3.7. + -. 0.28nm.
Comparative example 1-1 catalyst preparation
(1) Dissolving 1g of chloroplatinic acid in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for later use;
(2) 990mg of active carbon is weighed into a beaker, 50ml of glycol and 50ml of NaOH solution are added, and 1.4ml of prepared H is weighed 2 PtCl 6 ·6H 2 Oglycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the powder into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump, setting the flow rate (20 ml/min), starting a pump switch after the temperature of an oil bath pan reaches 160 ℃, waiting for 15 minutes, allowing the solution to completely flow out, collecting the solution in the beaker, adding acid, stirring, carrying out suction filtration on the solution to wash the reaction solution, placing the solid obtained after the suction filtration in a culture dish, drying the solid in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing the solid after the reaction solution is finished;
the catalyst was named as 1% Pt/C (V (EG: naOH solution) = 1).
Comparative examples 1-2 catalyst preparation
(1) Dissolving 1g of chloroplatinic acid in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for later use;
(2) 990mg of active carbon is weighed into a beaker, 60ml of ethylene glycol and 40ml of NaOH solution are added, and 1.4ml of prepared H is weighed 2 PtCl 6 ·6H 2 OO ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the mixture into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump, setting the flow rate (20 ml/min), starting a pump switch after the temperature of an oil bath pan reaches 160 ℃, waiting for 15 minutes, allowing the solution to completely flow out, collecting the solution in the beaker, adding acid, stirring, carrying out suction filtration on the solution to wash the reaction solution, placing the solid obtained after the suction filtration in a culture dish, drying the solid in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing the solid after the reaction solution is finished;
the catalyst was named as 1% Pt/C (V (EG: naOH solution) = 1.5).
Comparative examples 1-3 catalyst preparation
(1) Dissolving 1g of chloroplatinic acid in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for later use;
(2) 990mg of active carbon is weighed into a beaker, 70ml of ethylene glycol and 30ml of NaOH solution are added, and 1.4ml of prepared H is weighed 2 PtCl 6 ·6H 2 Oglycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the mixture into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump, setting the flow rate (20 ml/min), starting a pump switch after the temperature of an oil bath pan reaches 160 ℃, waiting for 15 minutes, allowing the solution to completely flow out, collecting the solution in the beaker, adding acid, stirring, carrying out suction filtration on the solution to wash the reaction solution, placing the solid obtained after the suction filtration in a culture dish, drying the solid in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing the solid after the reaction solution is finished;
the catalyst was named as 1% Pt/C (V (EG: naOH solution) = 2.3).
Comparative examples 1-4 catalyst preparation
(1) Dissolving 1g of chloroplatinic acid in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for later use;
(2) 990mg of active carbon is weighed into a beaker, 90ml of ethylene glycol and 10ml of NaOH solution are added, and 1.4ml of prepared H is weighed 2 PtCl 6 ·6H 2 Oglycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the mixture into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump, setting the flow rate (20 ml/min), starting a pump switch after the temperature of an oil bath pan reaches 160 ℃, waiting for 15 minutes, allowing the solution to completely flow out, collecting the solution in the beaker, adding acid, stirring, carrying out suction filtration on the solution to wash the reaction solution, placing the solid obtained after the suction filtration in a culture dish, drying the solid in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing the solid after the reaction solution is finished;
the catalyst was named as 1% Pt/C (V (EG: naOH solution) = 9).
Comparative examples 1-5 catalyst preparation
(1) Dissolving 1g of chloroplatinic acid in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for later use;
(2) 990mg of active carbon is weighed into a beaker, 50ml of glycol and 50ml of NaOH solution are added, and 1.4ml of prepared H is weighed 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the mixture into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump, setting the flow rate (20 ml/min), starting a pump switch after the temperature of an oil bath pan reaches 150 ℃, waiting for 15 minutes, allowing the solution to completely flow out, collecting the solution in the beaker, adding acid, stirring, carrying out suction filtration on the solution to wash the reaction solution, placing the solid obtained after the suction filtration in a culture dish, drying the solid in a vacuum drying oven at 80 ℃ for 12 hours, and sealing and storing the solid after the reaction solution is finished;
the catalyst was named 1% Pt/C (150 ℃ C.).
Comparative examples 1-6 catalyst preparation
(1) Dissolving 1g of chloroplatinic acid in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for later use;
(2) 990mg of active carbon is weighed into a beaker, 50ml of glycol and 50ml of NaOH solution are added, and 1.4ml of prepared H is weighed 2 PtCl 6 ·6H 2 Oglycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the mixture into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump, setting the flow rate (20 ml/min), starting a pump switch after the temperature of an oil bath pan reaches 170 ℃, waiting for 15 minutes, enabling the solution to completely flow out, finally collecting the solution in the beaker, adding acid, stirring, carrying out suction filtration on the solution to wash reaction liquid, finally placing the solid obtained after the suction filtration in a culture dish, placing the culture dish in a vacuum drying box at 80 ℃ for drying for 12 hours, and sealing and storing after the reaction liquid is finished;
the catalyst was named 1% Pt/C (170 ℃).
Example 2
(1) The continuous flow device consists of a peristaltic pump, a magnetic stirrer, a plurality of sections of Teflon pipelines, a reaction device and a beaker. The inlet end pipeline of the peristaltic pump is introduced into the beaker, the outlet end pipeline of the peristaltic pump is connected with a Teflon pipeline with a 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) Dissolving 1g of chloroplatinic acid in 50mL of ethylene glycol to prepare a platinum precursor solution (Pt: 7.5 mg/mL) for later use;
(3) Weighing 1.98g of active carbon in a beaker, adding 160ml of glycol and 40ml of NaOH solution, measuring 2.8ml of prepared H 2 PtCl 6 ·6H 2 Oglycol solution (20 mg H per 1ml solution) 2 PtCl 6 ·6H 2 O) adding the mixture into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump, setting the flow rate (20 ml/min), starting a pump switch after the temperature of an oil bath pan reaches 160 ℃, waiting for 15 minutes, enabling the solution to completely flow out, finally collecting the solution in the beaker, adding acid, stirring, carrying out suction filtration on the solution to wash reaction liquid, finally placing the solid obtained after the suction filtration in a culture dish, placing the culture dish in a vacuum drying oven at 80 ℃ for drying for 12 hours, and sealing and storing after the reaction liquid is finished.
Example 3 catalyst ICP test
The platinum-based catalysts prepared in example 1 and comparative examples 1-1, 1-2, 1-3, 1-4, 1-5, and 1-6 were measured by Inductively Coupled Plasma Emission Spectrometer (ICP-OES) after weighing, aqua regia dissolving, dilution, and volume fixing, and the results are shown in Table 1.
TABLE 1 catalyst ICP test results
According to the above results, the catalysts prepared in examples 1 and 2 have a loading rate of more than 95%, while the catalysts prepared in 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 poor loading effect, and can be used for preparing 2-pentanone by hydrogenating 2-methylfuran by using examples 1 and 2 in order to better follow the impregnation method (refer to patent CN 113999088B).
Example 4 hydrogenation of 2-methylfuran to 2-pentanone reactivity test
The reaction for preparing 2-pentanone by hydrogenating 2-methylfuran is carried out in an autoclave equipped with a thermal conductivity detector. Adding 50mg of the prepared platinum-based catalyst, 3.4mmol of 2-methylfuran and 8ml of isopropanol into a reaction kettle, purging the reaction kettle for 3 times by using 2MPa of hydrogen before reaction to remove air in the reaction kettle, filling 1MPa of hydrogen again, reacting at 200 ℃ for 3 hours, after the reaction is finished, putting the reaction kettle into ice water, rapidly cooling to room temperature, separating the catalyst and reaction liquid, and detecting the composition of the reaction liquid by using gas chromatography to obtain a reaction result.
The test results are shown in Table 2.
TABLE 2 hydrogenation of 2-methylfuran to 2-pentanone reactivity test
In order to better demonstrate the superiority of platinum-based catalysts prepared by the continuous flow method, the above catalysts were tested for the activity of hydrogenation of dimethylfuran to prepare 2-pentanone. According to the experimental results of table 2, 2-methylfuran has achieved 88% conversion on the catalyst of example 1, with 79% 2-pentanone yield, which is nearly 30% higher than 1% pt/C prepared using the impregnation method (50%). In addition, according to other comparison results, although the loading rate is not reached, the activity of the catalyst for preparing 2-pentanone by hydrogenating dimethyl furan is superior to that of the catalyst prepared by the impregnation method.
EXAMPLE 5 hydrogenation of 2-methylfuran to 2-pentanone reactivity test
The influence of temperature on the hydrogenation of 2-methylfuran to prepare 2-pentanone is explored: this example is different from example 4 in that the reaction temperature in the operation step is 120 deg.C, and the other procedures are the same as example 4.
EXAMPLE 6 hydrogenation of 2-methylfuran to 2-pentanone reactivity test
The influence of temperature on the hydrogenation of 2-methylfuran to prepare 2-pentanone is explored: this example is different from example 4 in that the reaction temperature in the operation step is 140 deg.C, and the other procedures are the same as example 4.
Example 7 hydrogenation of 2-methylfuran to 2-pentanone reactivity test
The influence of temperature on the hydrogenation of 2-methylfuran to prepare 2-pentanone is explored: this example is different from example 4 in that the reaction temperature in the operation step is 160 deg.C, and the other procedures are the same as example 4.
EXAMPLE 8 hydrogenation of 2-methylfuran to 2-pentanone reactivity test
The influence of temperature on the hydrogenation of 2-methylfuran to prepare 2-pentanone is explored: this example is different from example 4 in that the reaction temperature in the operation step is 180 ℃, and the other procedures are the same as example 4.
Example 9 hydrogenation of 2-methylfuran to 2-pentanone reactivity test
The influence of temperature on the preparation of 2-pentanone by hydrogenation of 2-methylfuran is explored: this example is different from example 4 in that the reaction temperature in the operation step is 220 ℃, and the other procedures are the same as example 4.
According to FIG. 5, the effect of reaction temperature on the product distribution is shown, the reaction product is mainly 2-pentanone, with increasing temperature, 2-methylfuran conversion increasing and 2-pentanone yield reaching the highest at 200 ℃.
According to the reaction result, the platinum-based catalyst is prepared by using a continuous flow method, the catalyst with the highest loading rate is obtained by optimizing the using amount of the solvent, and the platinum-based catalyst is applied to the reaction of preparing 2-pentanone by hydrogenating 2-methylfuran, so that the yield is obviously improved. The prepared particles are uniformly distributed and have small particle size. Compared with the prior process production route, the process route of the invention has simple preparation process, can effectively avoid human errors by mechanized operation, can obtain the required catalyst in one step, and greatly shortens the production time. The raw materials can be regenerated, the catalyst has high activity and mild reaction conditions, the energy consumption is reduced to a certain extent, and the method is environment-friendly and can effectively relieve the global energy problem. Therefore, the invention has wide application potential in industrial production.
The invention is not limited to the specific technical solutions described in the above embodiments, and all technical solutions formed by equivalent substitutions are within the scope of the invention as claimed.
Claims (6)
1. A method for preparing 2-pentanone by hydrogenation of 2-methylfuran by using a platinum-based catalyst is characterized by comprising the following steps: the reaction for preparing 2-pentanone by hydrogenating 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 for reaction to obtain 2-pentanone; the method comprises the following specific steps: the reaction for preparing 2-pentanone by hydrogenating 2-methylfuran is carried out in an autoclave provided with a thermal conductivity detector, isopropanol is used as a solvent, 1wt.% of Pt/C platinum-based catalyst is in a reaction solution with the mass concentration of 2-methylfuran of 5wt.%, the reaction kettle is purged for 3 times by using 2MPa hydrogen to remove air in the reaction kettle, 1MPa hydrogen is charged, the reaction temperature is 200 ℃, and the reaction time is 3 hours; 2-pentanone is prepared;
the preparation method of the platinum-based catalyst comprises the following steps: preparing a platinum-based catalyst using a continuous flow apparatus; the continuous flow device consists of a peristaltic pump, a magnetic stirrer, a Teflon pipeline, a reaction device and a collection device; the inlet end pipeline of the peristaltic pump is introduced into the container, the outlet end pipe of the peristaltic pump is connected with a section of Teflon pipeline with a length, the section of 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, adding appropriate amount of chloroplatinic acid (H) 2 PtCl 6 ·6H 2 O) a solid, and (C) a solid,
preparation of H by ultrasound 2 PtCl 6 ·6H 2 O ethylene glycol solution; wherein, pt:7.5mg/mL;
(2) Adding activated carbon into a container, adding a proper amount of glycol, a proper amount of sodium hydroxide solution and a proper amount of ultrapure water, and taking a proper amount of H prepared in the step (1) 2 PtCl 6 ·6H 2 Adding O glycol solution into the mixture to perform ultrasonic dispersion; wherein each 990mg of activated carbon corresponds to 100ml of solution, wherein 80ml of ethylene glycol and 20ml of NaOH solution, and each 990mg of activated carbon corresponds to 1.4ml of H 2 PtCl 6 ·6H 2 O ethylene glycol solution;
(3) The temperature of the reaction device is 160 ℃;
the collected catalyst 1% by weight Pt/C (V (EG: naOH solution) = 4) was dried in a vacuum drying oven.
2. The process for the hydrogenation of 2-methylfuran to 2-pentanone using a platinum-based catalyst according to claim 1, characterized in that: step 1 of the preparation method of the platinum-based catalyst is H 2 PtCl 6 ·6H 2 O ethylene glycol solution (20 mg H in 1ml ethylene glycol) 2 PtCl 6 ·6H 2 O); and (5) sealing and storing at low temperature.
3. The process for the hydrogenation of 2-methylfuran to 2-pentanone using a platinum-based catalyst according to claim 1, characterized in that: in the preparation method of the platinum-based catalyst, a sodium hydroxide solution is prepared in the step 2, ultrapure water is used, a proper amount of sodium hydroxide NaOH solid is added into the ultrapure water, and stirring is carried out to prepare a NaOH aqueous solution.
4. The process for the hydrogenation of 2-methylfuran to 2-pentanone using a platinum-based catalyst according to claim 1, characterized in that: in the preparation method of the platinum-based catalyst, the Pt mass content Pt in chloroplatinic acid in the step (1) is more than or equal to 37.5 percent, and the ultrasonic frequency is 40KHz.
5. The process for the hydrogenation of 2-methylfuran to 2-pentanone using a platinum-based catalyst according to claim 1, characterized in that: in the preparation method of the platinum-based catalyst, the collecting device is a beaker, the container is a beaker, a section of Teflon pipeline with the length is connected to the outlet of the peristaltic pump, and a Teflon pipeline with the diameter of 3 mm is adopted; the Teflon pipeline is circularly wound and is suspended in the reactor through a thin iron wire fixing disc.
6. The process for the hydrogenation of 2-methylfuran to 2-pentanone using a platinum-based catalyst according to claim 1, characterized in that:
the reaction for preparing 2-pentanone by hydrogenating 2-methylfuran is carried out in an autoclave provided with a thermal conductivity detector, 50mg of the prepared platinum-based catalyst, 3.4mmol of 2-methylfuran and 8ml of isopropanol are added into the autoclave, the autoclave is purged for 3 times by using 2MPa hydrogen before the reaction, so as to remove the air in the autoclave, and then 1MPa hydrogen is charged into the autoclave, the reaction temperature is 200 ℃, and the reaction time is 3 hours; 2-pentanone is prepared;
the preparation method of the platinum-based catalyst comprises the steps of weighing 990mg of active carbon in a beaker, adding 80ml of ethylene glycol and 20ml of NaOH solution, 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 mixture into the mixture, and performing ultrasonic treatment for 20min; placing the beaker in a continuous flow device, turning on a switch of a reaction device, regulating and controlling a peristaltic pump to set a flow rate of 50ml/min, starting the switch of the pump after the temperature of the reaction device reaches 160 ℃, waiting for 15 minutes, collecting the solution in the beaker, stirring overnight, carrying out suction filtration, finally placing the solid obtained after the suction filtration in a culture dish, placing the culture dish in a vacuum drying oven at 80 ℃ for drying for 12 hours, and sealing and storing after the completion.
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