CN116239549B - Method for using platinum-based catalyst in hydrogenation reaction of 2-methylfuran - Google Patents

Method for using platinum-based catalyst in hydrogenation reaction of 2-methylfuran Download PDF

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CN116239549B
CN116239549B CN202310252465.5A CN202310252465A CN116239549B CN 116239549 B CN116239549 B CN 116239549B CN 202310252465 A CN202310252465 A CN 202310252465A CN 116239549 B CN116239549 B CN 116239549B
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CN116239549A (en
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彭思渊
毛影
杨尧
王川
陈凯琴
李国佳
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Nanjing Tech University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/42—Platinum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • 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

Abstract

The invention discloses a method for using a platinum-based catalyst in 2-methylfuran hydrogenation reaction, belonging to the technical field of catalyst continuous flow method preparation. The carrier of the catalyst is a specific active carbon, the main active component is platinum, and a continuous flow integrated device is used for controllably preparing 1% Pt/C catalysts with different particle sizes. The selectivity of 2-pentanone reaches the highest when the catalyst particle diameter is 3.88 plus or minus 0.31nm, the selectivity of 2-methyltetrahydrofuran reaches the highest when the catalyst particle diameter is 2.99 plus or minus 0.30nm, the selectivity of 2-pentanol reaches the highest when the catalyst particle diameter is 2.50 plus or minus 0.36nm, and the furan selectivity is the highest by 31%. Compared with the traditional dipping method and precipitation deposition method, the continuous flow method can accurately control the conditions of reaction temperature, reaction time, solvent ratio and the like, and can realize the preparation of catalysts with different particle sizes. The method has simple steps, is not affected by human, has high catalyst batch repeatability, and can realize industrialization.

Description

Method for using platinum-based catalyst in hydrogenation reaction of 2-methylfuran
Technical Field
The invention belongs to the technical field of catalyst continuous flow method preparation, and in particular relates to a preparation method of a platinum-based catalyst for 2-methyl furan hydrogenation. The carrier of the catalyst is a specific active carbon, the main active component is platinum, and a continuous flow integrated device is used for controllably preparing 1% Pt/C catalysts with different particle sizes, and the catalyst can be used for hydrogenation reaction of 2-methylfuran. Compared with the traditional dipping method and precipitation deposition method, the continuous flow method can accurately control the conditions of reaction temperature, reaction time, solvent ratio and the like, and can realize the preparation of catalysts with different particle sizes. The method has simple steps, is not affected by human, has high catalyst batch repeatability, and can realize industrialization.
Background
The development of continuous flow microreaction technology in recent years has been a tool for simplifying, accelerating, integrating, amplifying and automating chemical reactions. In a continuous flow device, reactants continuously flow through the micromixer and then enter the microtube reactor, so that continuous preparation of products is realized. It exhibits an inherently safer, more environmentally friendly property than classical batch processes. For the synthesis of a fine catalyst, the continuous flow microreactor can show remarkable efficiency in the screening of reaction parameters such as temperature, residence time, solvent, substrate and the like, and can accurately regulate and control reaction conditions, so that the continuous flow microreactor has wide application prospect.
2-methyltetrahydrofuran (2-THMF) was approved by the United states department of energy as a gasoline additive. Furfural and other furanyl compounds (furfuryl alcohol, 2-methyl furan, tetrahydrofurfuryl alcohol) have a tendency to polymerize and are quite volatile. However, 2-methyltetrahydrofuran is inherently more stable and less volatile and is therefore suitable for use as an engine fuel. 2-methyltetrahydrofuran has been promoted as an ecologically low-hazard alternative to tetrahydrofuran. Although 2-methyltetrahydrofuran is more expensive, it can lead to greater economies in the overall synthesis process.
2-pentanone (2-PN), also known as methylpropyl ketone (MPK), is an important solvent for the most commonly used synthetic resins because of its low density, high solvent and moderate evaporation rate. 2-pentanone can be produced from furfural and its derivatives, 2-methylfuran being often used as a reactant for producing 2-pentanone using a platinum-based catalyst. In many reports, hydrogenation of the c=c and c=o motifs on furan compounds has met with great success. The hydrogenolysis of C-O bonds remains a key challenge.
Furan is mainly used for preparing pyrrole, thiophene, tetrahydrofuran, etc. The furan is etherified and reduced to obtain 2, 5-dimethoxy dihydrofuran, and the 2-hydroxy-1, 4-butanedialdehyde is generated by hydrolysis, so that the furan can be used for the production of anisodamine by a synthesis method. When furan is etherified, reduced and then subjected to catalytic hydrogenation to obtain 2, 5-dimethoxy tetrahydrofuran, succinic aldehyde is generated by hydrolysis, and the succinic aldehyde is a raw material for synthesizing atropine as another alkaloid.
The platinum catalyst loaded by the activated carbon has higher activity in the hydrogenolysis reaction of 2-methylfuran (2-MF), and can catalyze the 2-methylfuran (2-MF) to form pentanone in a liquid phase so as to be put into industrial use, thereby realizing the conversion and utilization of biomass energy. Metal catalysts with customizable size, uniform dispersion are generally considered as a prerequisite for obtaining better hydrogenation activity, selectivity and stability, so the controllable preparation of supported platinum-based catalysts of different particle size has a profound application prospect in terms of conversion utilization of biomass energy.
Pt/C is a key catalyst for many of the most advanced renewable energy technologies, such as Polymer Electrolyte Membrane (PEM) fuel cells (PEMFC) and PEM electrolyzers. The synthesis of Pt/C catalysts is typically accomplished by using Pt precursors (e.g. [ PtCl 6 ] 2+ ) Is realized by various physical, chemical or physicochemical approaches. Both the metal precursors and the synthetic route are important from the standpoint of processing and catalyst performance. The commercial production of the catalyst is preferred to be low cost and involves environmentally friendly processing of the Pt/C synthetic route. Because the loading, size, surface morphology, distribution state and other parameters of the Pt nano particles have great influence on the catalytic performance of the Pt/C catalyst, the synthesis of the Pt nano particles and the required structural parameters is still a topic of great concern. The size of Pt nanoparticles and their aggregation state can be controlled basically by varying the synthesis parameters. For example, variations in any of the parameters of strength and concentration of the reducing agent, concentration of Pt precursor, presence of surfactant, etc. can be used to control the particle size and aggregation state of Pt nanoparticles during synthesis by chemical routes.
Disclosure of Invention
In order to solve the technical problems, the invention provides a platinum-based catalyst for hydrogenation reaction of 2-methyl furan and a preparation method thereof. By utilizing the preparation method, through regulating and controlling the molar ratio of different metal precursors to alkali, different reaction time, reaction temperature and ethylene glycol volume in a continuous flow reactor, the supported platinum-based catalyst with different particle sizes can be obtained, the catalyst loading capacity can reach 1% of theoretical loading value, under the conditions that the hydrogen pressure is 1MPa, the reaction temperature is 120 ℃, the reaction time is 3h, the conversion rate of 2-methylfuran can reach 63%, the larger the particle size of the platinum-based catalyst is, the higher the selectivity of 2-pentanone is, the catalyst particle size reaches 46% at most when 3.88+/-0.31 nm, the selectivity of 2-methyltetrahydrofuran reaches 32% at most when the catalyst particle size is 2.99+/-0.30 nm, the selectivity of 1-pentanol is stable when the catalyst particle size is 2.99+/-0.30 nm, the selectivity of 2-pentanol is increased and then reduced when the catalyst particle size is 2.50+/-0.36 nm, the selectivity of furan reaches 29% when the catalyst particle size is 29% and the selectivity of furan is more greatly reduced when the catalyst particle size is 0,1.28.31% when the catalyst particle size is greatly influenced by the catalyst particle size is more than 25 nm. Meanwhile, the preparation method can realize the production of 6 g of catalyst per hour, the production efficiency is obviously improved, and the platinum-based catalyst (1% Pt/C) with low loading rate is prepared for the catalytic hydrogenolysis reaction of 2-methylfuran so as to realize biomass energy conversion and utilization, and has wide application prospect.
In order to solve the technical problems of the invention, the technical proposal is as follows: a method of using a platinum-based catalyst for 2-methylfuran hydrogenation reactions, comprising the steps of:
preparing a platinum-based catalyst using a continuous flow device; the continuous flow device consists of a peristaltic pump, a magnetic stirrer, a polytetrafluoroethylene soft and hard tube butt joint, a polytetrafluoroethylene pipeline, an oil bath pot and a collecting device;
the inlet end pipeline of the peristaltic pump is inserted into the container, the outlet end pipeline of the peristaltic pump is connected with one end of a polytetrafluoroethylene soft and hard pipe butt joint, the other end of the butt joint is connected with a polytetrafluoroethylene pipeline with the length of 50 meters, the polytetrafluoroethylene pipeline is arranged in an oil bath pot, and finally the outlet end of the polytetrafluoroethylene pipeline is fixed above the collecting device; the pipe diameters of the inlet end pipeline, the outlet end pipeline and the polytetrafluoroethylene pipeline are millimeter-sized;
(1) The ethylene glycol solution is used, and a proper amount of chloroplatinic acid H is added into the ethylene glycol solution 2 PtCl 6 ·xH 2 O solid, oscillating, ultrasonic to prepare H 2 PtCl 6 ·xH 2 An O ethylene glycol solution;
(2) Adding a proper amount of NaOH solid into the glycol solution, heating and stirring to prepare the NaOH glycol solution
(3) Adding a proper amount of ethylene glycol into a container;
(4) Adding a proper amount of NaOH glycol solution prepared in the step (2) into another container, and adding a proper amount of ultrapure water while stirring for dispersion;
(5) Adding the solution prepared in the step (4) into the glycol prepared in the step (3), and adding the H prepared in the step (1) into the mixed solution 2 PtCl 6 ·xH 2 Adding a proper amount of activated carbon into the mixed solution, and ultrasonically treating chloroplatinic acid in the catalyst: the mol ratio of NaOH is 1-1:1000; ethylene glycol plus NaOH: the volume ratio of water is 5:1;
(6) Adding a proper amount of concentrated hydrochloric acid into ultrapure water to prepare 9mol/L hydrochloric acid solution;
(7) Stirring and cooling the collected liquid to room temperature, adding a proper amount of hydrochloric acid solution prepared in the step (6), regulating the pH of the solution to 1-2, and stirring for 12h;
(8) And (3) carrying out suction filtration on the solution obtained in the step (7) by using a positive pressure suction filtration instrument, washing the solution with ultrapure water until the conductivity is zero, and putting the catalyst after suction filtration and washing into a vacuum drying oven for drying.
The hydrogenation reaction route of the 2-methylfuran is as follows:
the size of the catalyst particle is influenced by the mole ratio of Pt to NaOH, and the larger the mole ratio of Pt to NaOH is, the larger the catalyst particle size is, otherwise, the smaller the catalyst particle size is; when the mole ratio of Pt to NaOH is 1:1, the catalyst particle size is 3.88+/-0.31 nm, when the mole ratio of Pt to NaOH is 1:1000, the particle size of the catalyst is 1.28+/-0.26 nm;
catalyst 1% Pt/C, pt to NaOH molar ratio 1:100, at a reaction temperature of 120 ℃,1MPa H 2 Under the condition of three hours of reaction, the conversion rate of the 2-methyl furan hydrogenation reaction can reach 63%, the selectivity of 2-pentanone is influenced by the size of the catalyst particle diameter, the larger the catalyst particle diameter is, the higher the selectivity of 2-pentanone is, the highest 46% is reached when the catalyst particle diameter is 3.88+/-0.31 nm, the selectivity of 2-methyl tetrahydrofuran is firstly increased and then reduced along with the decrease of the catalyst particle diameter from small to large, the highest 32% is reached when the catalyst particle diameter is 2.99+/-0.30 nm, the selectivity of 1-pentanol is relatively stable, the catalyst particle diameter is between 4% and 7%, the catalyst particle diameter is from small to large, the selectivity of 2-pentanol is firstly increased and then decreased, the catalyst particle diameter is 2.50+/-0.36 nm and is the largest, the influence of the particle diameter is relatively obvious, and the selectivity of furan is the highest 31% when the catalyst particle diameter is reduced from small to large, and the selectivity of furan is reduced from 31% to 0,1.28 +/-0.26 nm.
Preferably, the method comprises the following steps:
(1) An appropriate amount of chloroplatinic acid H was added thereto at 25℃using an ethylene glycol solution 2 PtCl 6 ·xH 2 O solid, ultrasonic for 30min to prepare H 2 PtCl 6 ·xH 2 Ethylene glycol solution of O (7.6 mg H 2 PtCl 6 ·xH 2 O/1mL solution), sealing and shading for preservation;
(2) Adding a proper amount of NaOH solid into the ethylene glycol solution at 25 ℃ by using the ethylene glycol solution, heating and stirring to prepare the ethylene glycol solution of NaOH;
(3) Adding a proper amount of ethylene glycol into a beaker;
(4) Adding a proper amount of ethylene glycol solution of NaOH prepared in the step (2) into another beaker, and adding a proper amount of ultrapure water for dispersion;
(5) Taking a proper amount of H prepared in the step (1) 2 PtCl 6 ·xH 2 Adding the glycol solution of O into the mixed solution obtained in the step (4);
(6) Adding the solution obtained in the step (5) into the glycol obtained in the step (3); weighing 2g of carbon carrier and adding the carbon carrier into the mixed solution; ultrasonic treatment for 30min;
(7) Placing the solution prepared in the step (6) under a peristaltic pump, introducing a pipeline when the temperature of the oil bath reaches a set temperature, sampling, waiting for a period of time, and collecting with a beaker;
(8) Stirring and cooling the collected liquid to room temperature, adding a proper amount of hydrochloric acid solution prepared in the step (6), regulating the pH of the solution to 1-2, and stirring for 12h;
(9) And (3) carrying out suction filtration on the solution obtained in the step (8) by using a positive pressure suction filtration instrument, washing with deionized water, drying in a vacuum drying oven for 12 hours, and sealing and preserving after the completion of the drying.
Preferably, the ratio of chloroplatinic acid solution to catalyst is: 658. Mu.l of H per 495mg of activated carbon 2 PtCl 6 ·xH 2 And O ethylene glycol solution.
Preferably, 160mL of ethylene glycol is measured and added into a beaker A, 40mL of prepared 1mol/L-16 mol/NaOH ethylene glycol solution is moved and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, the ultrapure water in the beaker C is moved into the beaker B by using a pipette, the mixture is added into the beaker A after the mixture is fully mixed while being pipetted, and 2.63mL of prepared 7.6mg/mLH is pipetted 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (25 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, waiting for 20 minutes, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12 hours, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, placing the catalyst into a vacuum drying oven at 80 ℃, drying for 12 hours, and packaging and sealing.
The beneficial effects of the invention are as follows:
compared with the traditional preparation method impregnation method, the continuous flow preparation method provided by the invention has the advantages that the continuous flow integrated device is used, the reaction temperature and the reaction time can be accurately controlled, the artificial error is greatly reduced, a plurality of catalysts can be prepared at the same time, and the efficiency is greatly improved. The method uses a continuous flow integrated device to controllably prepare the 1% Pt/C catalyst with different particle sizes by changing the mole ratio of metal precursor to alkali, the reaction temperature, the reaction flow rate, the reaction time and the volume of glycol in the preparation process.
160mL of ethylene glycol, 40mL of LNaOH ethylene glycol solution and 40mL of ultrapure water, H were added to 1.9g of activated carbon 2 PtCl 6 ·xH 2 The mol ratio of O to NaOH is 1:1-1:1000. As can be seen from table 1, the catalyst particle size is affected by the mole ratio of Pt to NaOH, the larger the mole ratio, the larger the catalyst particle size, whereas the smaller the catalyst particle size, when the mole ratio of Pt to NaOH is 1:1, the catalyst particle size is 3.88+/-0.31 nm, when the mole ratio of Pt to NaOH is 1:1000, the catalyst particle size is 1.28+ -0.26.
Catalyst 1% Pt/C (1:100), at reaction temperature 120 ℃,1MPa H 2 Under the condition of three hours of reaction, the conversion rate of the hydrogenation reaction of the 2-methylfuran can reach 63 percent, the selectivity of the 2-pentanone is influenced by the particle size of the catalyst, and the higher the particle size of the catalyst is, the higher the selectivity of the 2-pentanone is, and the highest the selectivity of the 2-pentanone is up to 46 percent. As the particle size of the catalyst is from small to large, the selectivity of the 2-methyltetrahydrofuran is increased and then reduced, and the selectivity reaches the maximum 32% at 2.99+/-0.30 nm. The selectivity of the 1-amyl alcohol is also relatively stable, and is between 4 and 7 percent. The particle size of the catalyst is from small to large, the selectivity of 2-amyl alcohol is increased and then reduced, and the catalyst reaches the maximum at 2.50+/-0.36 nm, and can reach 29 percent. The furan selectivity is also obviously affected by the particle size, and when the particle size of the catalyst is from small to large, the furan selectivity is reduced from 31% to 0.
The method adopts mechanized operation to avoid human errors, so that the result is easier to repeat, the production efficiency is greatly improved, and 2g of catalyst can be produced every 20 minutes. In addition, the invention can easily prepare the platinum-based catalyst (1% Pt/C) with low loading rate, greatly saves cost, has better catalytic performance on 2-methyl furan hydrogenation reaction, and is suitable for industrial production.
Drawings
FIG. 1 is a schematic diagram of a continuous flow integrated device
FIG. 2 is an electron micrograph of the catalyst prepared in example 1
FIG. 3 is an electron micrograph of the catalyst prepared in example 2
FIG. 4 is an electron micrograph of the catalyst prepared in example 3
FIG. 5 is an electron micrograph of the catalyst prepared in example 4
FIG. 6 is an electron micrograph of the catalyst prepared in example 5
FIG. 7 is a plot of selectivity versus particle size for the catalyst activity test product of example 6 FIG. 1: 1-peristaltic pump, 2-magnetic stirrer, 3-polytetrafluoroethylene pipeline, 4-oil bath pot and 5-oil bath pot controller
Detailed Description
Example 1 catalyst preparation
Preparing a platinum-based catalyst using a continuous flow device; the continuous flow device consists of a peristaltic pump, a magnetic stirrer, a polytetrafluoroethylene soft and hard tube butt joint, a polytetrafluoroethylene pipeline, an oil bath pot and a collecting device;
the inlet end pipeline of the peristaltic pump is inserted into the container, the outlet end pipeline of the peristaltic pump is connected with one end of a polytetrafluoroethylene soft and hard pipe butt joint, the other end of the butt joint is connected with a polytetrafluoroethylene pipeline with the length of 50 meters, the polytetrafluoroethylene pipeline is arranged in an oil bath pot, and finally the outlet end of the polytetrafluoroethylene pipeline is fixed above the collecting device; the pipe diameters of the inlet end pipeline, the outlet end pipeline and the polytetrafluoroethylene pipeline are millimeter-sized;
160mL of ethylene glycol is measured and added into a beaker A, 39.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, and 2.63mL of prepared 7.6mg/mLH is transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting the flow rate (25 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, waiting for 20min, completely feeding the solution into a collecting device, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid, and regulating the pH of the solution to 1-2, stirring for 12h, filtering by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, putting into a vacuum drying oven at 80 ℃ for drying for 12h, and packaging and sealing after the completion. The yield of this example was 2g of product per 20 minutes with a loading of 1%. (i.e., platinum 1% by mass of the catalyst)
The catalyst was designated 1% Pt/C (Pt: naOH molar ratio 1:1).
Comparative example 1-1 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 39.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, and 2.63mL of prepared 7.6mg/mLH is transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (5 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, after 110min, completely feeding the solution into a collecting device, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, putting the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing. The yield of this comparative example was 2 grams of product per 110 minutes and the loading was 0.7%.
The catalyst was named 1% Pt/C (1:1) (5 mL/min).
Compared with example 1, the reaction flow rate is changed, the load is not 1%, and the reaction conversion rate is only 40% when the catalyst is applied to the 2-methyl furan reaction, and is lower than that of example 1.
Comparative examples 1-2 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 39.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, and the ultrapure water in the beaker C is moved to the beaker by using a liquid-moving gunB, adding the mixed solution into the beaker A after the mixed solution is fully mixed while pipetting, and pipetting 2.63mL of prepared 7.6mg/mLH 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (10 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, after 80min, completely feeding the solution into a collecting device, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, putting the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing. The yield of this comparative example was 2 grams of product per 80 minutes with a loading of 0.7%.
The catalyst was named 1% Pt/C (1:1) (10 mL/min).
Compared with example 1, the reaction flow rate was changed, the loading did not reach 1%, and the reaction conversion was only 47% when applied to the 2-methylfuran reaction, which is lower than in example 1.
Comparative examples 1-3 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 39.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, and 2.63mL of prepared 7.6mg/mLH is transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting the flow rate (15 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, waiting for 50min, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, placing the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging after the completionAnd (5) sealing. The yield of this example was 2g of product per 50 minutes and the loading was 0.8%.
The catalyst was named 1% Pt/C (1:1) (15 mL/min).
Compared with example 1, the reaction flow rate was changed, the loading did not reach 1%, and the reaction conversion was lower than in example 1 when applied to the 2-methylfuran reaction.
Comparative examples 1-4 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 39.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, and 2.63mL of prepared 7.6mg/mLH is transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (20 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, waiting for 30min, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, placing the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing. The yield of this example was 2g of product per 30 minutes and the loading was 0.8%.
The catalyst was named 1% Pt/C (1:1) (20 mL/min).
Compared with example 1, the reaction flow rate is changed, the load is not 1%, and the reaction conversion rate is only 44% when the catalyst is applied to the 2-methyl furan reaction, and is lower than that of example 1.
Comparative examples 1-5 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 39.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, and a pipette is used for transferring the ultrapure water in the beaker C into the beaker B whileAdding the mixed solution into a beaker A after the solution is fully mixed while stirring, and transferring 2.63mL of prepared 7.6mg/mLH 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (30 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, waiting for 10min, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, placing the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing. The yield of this example was 2g of product per 10 minutes and the loading was 0.9%.
The catalyst was named 1% Pt/C (1:1) (30 mL/min).
Compared with example 1, the reaction flow rate was changed, the loading did not reach 1%, and the reaction conversion was only 51% when applied to the 2-methylfuran reaction, which was lower than in example 1.
Comparative examples 1-6 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 39.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, and 2.63mL of prepared 7.6mg/mLH is transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (35 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, waiting for 8min, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, placing the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing.The yield of this example was 2g of product per 8 minutes and the loading was 0.7%.
The catalyst was named 1% Pt/C (1:1) (35 mL/min).
Compared with example 1, the reaction flow rate is changed, the load is not 1%, and the reaction conversion rate is only 37% when the catalyst is applied to the 2-methyl furan reaction, and is lower than that of example 1.
Comparative examples 1-7 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 39.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, and 2.63mL of prepared 7.6mg/mLH is transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (40 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, waiting for 6min, completely feeding the solution into a collecting device, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, putting the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing. The yield of this example was 2g of product per 6 minutes and the loading was 0.6%.
The catalyst was named 1% Pt/C (1:1) (40 mL/min).
Compared with example 1, the reaction flow rate is changed, the load is not 1%, and the reaction conversion rate is only 48% when the catalyst is applied to the 2-methyl furan reaction, and is lower than that of example 1.
Comparative example 2-1 catalyst preparation
80mL of ethylene glycol is measured and added into a beaker A, 19.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 20mL of ultrapure water is measured and added into a beaker C, and a pipette is used for transferring the ultrapure water in the beaker C into the beaker B while transferringStirring, adding the mixed solution into a beaker A after fully mixing, and transferring 2.63mL of prepared 7.6mg/mLH 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (25 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, after 20min, completely feeding the solution into a collecting device, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, putting the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing. The yield of this comparative example was 2 grams of product per 20 minutes with a loading of 0.8%.
The catalyst was named 1% Pt/C (1:1) (100 mL solvent).
Compared with example 1, the amount of the solvent is changed, the loading is less than 1%, and the reaction conversion rate is only 53% when the solvent is applied to the 2-methyl furan reaction, which is lower than that of example 1.
Comparative example 2-2 catalyst preparation
240mL of ethylene glycol is measured and added into a beaker A, 59.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 60mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, and 2.63mL of prepared 7.6mg/mLH is transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (25 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, after 20min, completely feeding the solution into a collecting device, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, putting the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing.The yield of this comparative example was 2 grams of product per 20 minutes with a loading of 0.8%.
The catalyst was named 1% Pt/C (1:1) (300 mL solvent).
Compared with example 1, the amount of the solvent is changed, the loading is less than 1%, and the reaction conversion rate is only 45% when the solvent is applied to the 2-methyl furan reaction, which is lower than that of example 1.
Comparative example 3-1 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 39.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, and 2.63mL of prepared 7.6mg/mLH is transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pan to be 150 ℃, regulating a peristaltic pump, setting a flow rate (25 ml/min), starting a switch after the temperature of the oil bath pan reaches the set temperature, waiting for 20min, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to be 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, putting the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing. The yield of this example was 2g of product per 20 minutes and the loading was 0.7%.
The catalyst was designated 1% Pt/C (1:1) (150 ℃).
Compared with example 1, the reaction temperature is changed, the load amount is not 1%, and the reaction conversion rate is only 43% when the catalyst is applied to the 2-methyl furan reaction, and is lower than that of example 1.
Comparative example 3-2 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 39.36mL of ethylene glycol is measured and added into a beaker B, 0.64mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, and the ultrapure water in the beaker C is moved into the beaker B by using a pipetteAdding the mixed solution into a beaker A after full mixing while pipetting and stirring, and pipetting 2.63mL of prepared 7.6mg/mLH 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pan to 170 ℃, regulating a peristaltic pump, setting a flow rate (25 ml/min), starting a switch after the temperature of the oil bath pan reaches the set temperature, waiting for 20min, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, placing the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing. The yield of this example was 2g of product per 20 minutes and the loading was 0.8%.
The catalyst was designated 1% Pt/C (1:1) (170 ℃).
Compared with example 1, the reaction temperature is changed, the load amount is not 1%, and the reaction conversion rate is only 47% when the catalyst is applied to the 2-methyl furan reaction, and is lower than that of example 1.
Example 2 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 33.59mL of ethylene glycol is measured and added into a beaker B, 6.41mL of prepared 1mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, and 2.63mL of prepared 7.6mg/mLH is transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow speed (25 mL/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, waiting for 20min, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, placing the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and sealing after the completion of the drying. The yield of this example was 2g of product per 20 minutes with a loading of 1%.
The catalyst was designated 1% Pt/C (Pt: naOH molar ratio 1:10).
Example 3 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 18.63mL of ethylene glycol is measured and added into a beaker platinum, 21.37mL of prepared 3mol/L NaOH ethylene glycol solution is measured and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, and 2.63mL of prepared 7.6mg/mLH is transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (25 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, waiting for 20min, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, placing the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing. The yield of this example was 2g of product per 20 minutes with a loading of 1%.
The catalyst was designated 1% Pt/C (Pt: naOH molar ratio 1:100).
Example 4 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 40mL of prepared 8mol/L NaOH ethylene glycol solution is moved and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, 2.63mL of prepared 7.6mg/mLH are moved and taken 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting the flow rate (25 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, and waiting for 20After the min, the solution is completely put into a collecting device, the solution is cooled to room temperature, a proper amount of prepared 9mol/L hydrochloric acid is added to adjust the pH of the solution to 1-2, the solution is stirred for 12h, then is filtered by a positive pressure suction filtration device, is washed by deionized water, is taken out, is put into a vacuum drying oven at 80 ℃ for drying for 12h, and is packaged and sealed after the completion of the drying. The yield of this example was 2g of product per 20 minutes with a loading of 1%.
The catalyst was designated 1% Pt/C (Pt: naOH molar ratio 1:500).
Example 5 catalyst preparation
160mL of ethylene glycol is measured and added into a beaker A, 40mL of prepared 16mol/L NaOH ethylene glycol solution is moved and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, 2.63mL of prepared 7.6mg/mLH are transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pot to 160 ℃, regulating a peristaltic pump, setting a flow rate (25 ml/min), starting a switch after the temperature of the oil bath pot reaches the set temperature, waiting for 20min, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out the catalyst, placing the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, and packaging and sealing. The yield of this example was 2g of product per 20 minutes with a loading of 1%.
The catalyst was designated 1% Pt/C (Pt: naOH molar ratio 1:1000).
Example 6 2-methyl Furan hydrogenation Activity test
The hydrogenation of 2-methylfuran is carried out in an autoclave equipped with a thermal conductivity detector. Adding 50mg of the prepared platinum-based catalyst and 4mmol of 2-methyl furan into a reaction kettle, purging the reaction kettle with hydrogen of 2MPa for 3 times before reaction to remove air in the reaction kettle, filling hydrogen of 1MPa, reacting at 120 ℃ for 3 hours, putting the reaction kettle into ice water after the reaction is finished, rapidly cooling to room temperature, separating the catalyst from the reaction liquid, and detecting the composition of the reaction liquid by using gas chromatography to obtain a reaction result.
The 2-methylfuran hydrogenation scheme is as follows:
the platinum-based catalysts prepared in examples 1, 2, 3, 4, 5 were used in 1MPaH 2 Activity tests were performed at 120℃for three hours, and the test results are shown in Table 1.
Table 1 2-test of hydrogenation reactivity of methylfuran
As can be seen from table 1, the catalyst particle size is affected by the mole ratio of Pt to NaOH, the larger the mole ratio, the larger the catalyst particle size, whereas the smaller the catalyst particle size, when the mole ratio of Pt to NaOH is 1:1, the catalyst particle size is 3.88+/-0.31 nm, when the mole ratio of Pt to NaOH is 1:1000, the catalyst particle size is 1.28+ -0.26.
Catalyst 1% Pt/C (1:100), at reaction temperature 120 ℃,1MPa H 2 Under the condition of three hours of reaction, the conversion rate of the 2-methylfuran hydrogenation reaction can reach 63%, the selectivity of the 2-pentanone is influenced by the size of the catalyst particle diameter, the larger the catalyst particle diameter is, the higher the selectivity of the 2-pentanone is, and the highest 46% of the catalyst particle diameter is when the catalyst particle diameter is 3.88+/-0.31 nm. With the particle size of the catalyst from small to large, the selectivity of the 2-methyltetrahydrofuran is firstly increased and then reduced, and the selectivity reaches the maximum 32% when the particle size of the catalyst is 2.99+/-0.30 nm. The selectivity of the 1-amyl alcohol is also relatively stable, and is between 4 and 7 percent. The particle size of the catalyst is from small to large, the selectivity of 2-amyl alcohol is increased and then reduced, and the catalyst reaches the maximum at the particle size of 2.50+/-0.36 nm, which can reach 29%. The furan selectivity is obviously influenced by the particle size, when the particle size of the catalyst is from small to large, the furan selectivity is reduced from 31% to 0, and when the particle size of the catalyst is 1.28+/-0.26 nm, the selectivity reaches the maximum 31%.

Claims (1)

1. A platinum-based catalyst for hydrogenation reaction of 2-methyl furan is characterized in that: the method 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 polytetrafluoroethylene soft and hard tube butt joint, a polytetrafluoroethylene pipeline, an oil bath pot and a collecting device;
the inlet end pipeline of the peristaltic pump is inserted into the container, the outlet end pipeline of the peristaltic pump is connected with one end of a polytetrafluoroethylene soft and hard pipe butt joint, the other end of the butt joint is connected with a polytetrafluoroethylene pipeline with the length of 50 meters, the polytetrafluoroethylene pipeline is arranged in an oil bath pot, and finally the outlet end of the polytetrafluoroethylene pipeline is fixed above the collecting device; the pipe diameters of the inlet end pipeline, the outlet end pipeline and the polytetrafluoroethylene pipeline are millimeter-sized;
160mL of ethylene glycol is measured and added into a beaker A, 40mL of prepared 16mol/L NaOH ethylene glycol solution is moved and added into a beaker B, 40mL of ultrapure water is measured and added into a beaker C, a pipette is used for transferring the ultrapure water in the beaker C into the beaker B, stirring is carried out while transferring, after full mixing, the mixed solution is added into the beaker A, 2.63mL of prepared 7.6mg/mLH are transferred 2 PtCl 6 ·xH 2 Adding the O ethylene glycol solution into a beaker A, weighing 1900mg of active carbon, adding into the beaker A, and performing ultrasonic treatment for 30min; placing the beaker into a continuous flow device, setting the temperature of an oil bath pan to 160 ℃, regulating a peristaltic pump, setting the flow rate to 25ml/min, starting a switch after the temperature of the oil bath pan reaches the set temperature, waiting for 20min, allowing the solution to enter a collecting device completely, cooling the solution to room temperature, adding a proper amount of prepared 9mol/L hydrochloric acid to regulate the pH of the solution to 1-2, stirring for 12h, performing suction filtration by using a positive pressure suction filtration device, washing with deionized water, taking out a catalyst, placing the catalyst into a vacuum drying oven at 80 ℃, drying for 12h, packaging, sealing after the completion, obtaining 2g of product every 20min, and ensuring the load rate to be 1%; the catalyst was named 1% Pt/C, pt: naOH has a molar ratio of 1:1000;
the hydrogenation reaction of 2-methylfuran is carried out in an autoclave provided with a thermal conductivity detector, 50mg of the prepared platinum-based catalyst and 4mmol of 2-methylfuran are added into the autoclave, the autoclave is purged for 3 times by using hydrogen of 2MPa before the reaction, so as to remove air in the autoclave, the hydrogen of 1MPa is filled again, the reaction temperature is 120 ℃, the reaction time is 3 hours, after the reaction is finished, the autoclave 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 hydrogenation reaction route of the 2-methylfuran is as follows:
when the mole ratio of Pt to NaOH is 1:1000, the grain diameter of the catalyst is 1.28 plus or minus 0.26nm, and the reaction temperature is 120 ℃ and 1MPa H 2 Under the condition of three hours of reaction, the conversion rate of the hydrogenation reaction of the 2-methylfuran is 41 percent, and the furan selectivity reaches 31 percent.
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CN114031480A (en) * 2021-12-21 2022-02-11 南京工业大学 Method for preparing amyl alcohol by hydrogenation of 2-methylfuran through platinum-based catalyst
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