CN115779949B - N-doped Pd-Co bimetallic magnetic catalyst, preparation method and application thereof in furfuryl alcohol preparation process by furfural hydrogenation - Google Patents

N-doped Pd-Co bimetallic magnetic catalyst, preparation method and application thereof in furfuryl alcohol preparation process by furfural hydrogenation Download PDF

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CN115779949B
CN115779949B CN202211503248.0A CN202211503248A CN115779949B CN 115779949 B CN115779949 B CN 115779949B CN 202211503248 A CN202211503248 A CN 202211503248A CN 115779949 B CN115779949 B CN 115779949B
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刘建国
马隆龙
张琦
陈伦刚
张兴华
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Southeast University
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Abstract

The invention relates to the technical field of high-value chemical industry for preparing high-value chemicals by high-efficiency catalytic conversion of biomass platform compounds, in particular to an N-doped Pd-Co bimetallic magnetic catalyst, a preparation method and application thereof in a furfuryl alcohol preparation process by hydrogenation of furfural, wherein solid powder is obtained by reduction for 1-5 h at 900 ℃, and the Pd-Co bimetallic magnetic catalyst Pd-Co@N/C is obtained by acid washing, freeze drying, grinding and sieving of the solid powder. The catalyst can be used for preparing furfuryl alcohol by hydrogenating biomass platform compound furfural with high efficiency and selectivity under the conditions of 2.0MPa, 120 ℃ and water as solvent. The Pd-Co bimetallic magnetic catalyst adopted by the method has the advantages of simple preparation process, easy recycling of magnetism and the like. The catalyst has the advantages of high conversion efficiency, good furfuryl alcohol product selectivity, mild reaction conditions and the like in the furfuryl alcohol preparation reaction by selective hydrogenation of furfural.

Description

N-doped Pd-Co bimetallic magnetic catalyst, preparation method and application thereof in furfuryl alcohol preparation process by furfural hydrogenation
Technical Field
The invention relates to the technical field of high-value chemical industry for preparing high-value chemicals by high-efficiency catalytic conversion of biomass platform compounds, in particular to an N-doped Pd-Co bimetallic magnetic catalyst, a preparation method and application thereof in a furfuryl alcohol preparation process by furfural hydrogenation.
Background
Furfural is an important biomass platform compound, and high-efficiency catalytic conversion of furfural for preparing high-value chemicals, materials, medicines and the like has important significance for biomass high-value utilization. However, in the selective hydrogenation process of furfural, the molecular structure of the furfural contains various functional groups, such as unsaturated functional groups of c= O, C =c, and the like, so that the selective hydrogenation reaction product of furfural is complex, and the selectivity of a single product is low. Furfuryl alcohol is an important organic raw material as an atomic economical high-value product prepared by directly and selectively hydrogenating furfural, and has very wide application in industries such as synthetic fiber, rubber, pesticide and the like.
Transition metal catalysts, particularly transition noble metal catalysts such as Ru and Rh, have higher catalytic performance in furfuryl alcohol preparing reaction systems by selective hydrogenation of furfural, but the catalyst cost is high, and under severe reaction conditions, active components of the catalyst are easy to run off, so that the catalyst has poor recycling performance, and the wide application of the catalyst in the practical industry is limited. Therefore, the development of the multiphase metal catalyst with high hydrothermal stability and low cost has important significance for selectively preparing furfuryl alcohol from the biomass platform compound furfural. China is the country with the largest yield and trade of furfural, furfuryl alcohol and processed products thereof in the world, but the traditional catalysts for producing furfuryl alcohol generally adopt copper-chromium-based catalysts which contain cancerogenic substances chromium, are difficult to separate and regenerate later, and have serious influence on the environment. Therefore, how to design and develop an efficient and environment-friendly furfuraldehyde selective hydrogenation catalyst for preparing furfuralcohol, selectively reserve C=C double bonds and hydrogenate C=O double bonds, and the improvement of the effective conversion rate of furaldehyde and the selectivity of furfuralcohol products are still an important point in the research direction of high-valued utilization of biomass platform compounds.
Based on the above, the invention provides an N-doped Pd-Co bimetallic magnetic catalyst, a preparation method and application thereof in furfuryl alcohol preparation technology by furfural hydrogenation. Through a simple in-situ synthesis means, the Pd-Co bimetallic magnetic catalyst is reasonably designed and prepared, and meanwhile, a high-efficiency and high-temperature furfurol selective hydrogenation reaction catalytic system is constructed, so that the key problems of preparing furfuryl alcohol by selectively hydrogenating C=O double bonds and retaining C=C double bonds in furfurol by using the catalyst with stability and low cost are effectively solved.
Disclosure of Invention
The invention aims at solving the problems in the background technology and provides an N-doped Pd-Co bimetallic magnetic catalyst, a preparation method and application thereof in furfuryl alcohol preparation technology by furfural hydrogenation.
According to the technical scheme, the N-doped Pd-Co bimetallic magnetic catalyst comprises a Co salt, a carbon source, a Pd salt and an amine source in a molar ratio of 30:30:1:30 to prepare the bimetallic magnetic catalyst Pd-Co@N/C.
The preparation method of the N-doped Pd-Co bimetallic magnetic catalyst comprises the following specific steps:
S1, mixing Co salt, a carbon source, pd salt and an amine source according to a molar ratio of 30:30:1:30 in a solvent, stirring for 2-8 hours at 20-100 ℃ to form a uniform jelly, and drying the formed jelly at 50-120 ℃ to obtain a catalyst precursor Pd-Co-N/C;
S2, heating the catalyst precursor Pd-Co-N/C obtained in the S1 in an inert and hydrogen mixed gas flow to 200-900 ℃ for roasting for 1-5 hours to obtain solid powder, heating and pickling the solid powder in an environment of 50-80 ℃, freeze-drying, grinding and sieving to obtain the Pd-Co bimetallic magnetic catalyst Pd-Co@N/C.
Preferably, in S1, the anion of the metal Co salt is any one of nitrate ion, sulfate ion, phosphate ion, acetate ion, and halogen ion;
the carbon source is any one of glucose, malic acid, tartaric acid, benzoic acid, ascorbic acid, oxalic acid, caffeic acid, salicylic acid and citric acid;
The anions of the metal Pd salt are any one of nitrate ions, chloride ions and sulfate ions;
The amine source is any one of melamine, histidine, ammonium citrate, urea and 1, 2-propylene diamine.
Preferably, in S1, the solvent is one or a mixture of more of dichloromethane, deionized water, methanol, isopropanol, tetrahydrofuran, dioxane, 2-butanol, chloroform and ethanol.
Preferably, in S2, the temperature-rising roasting method of the Pd-Co-N/C catalyst precursor is as follows: raising the temperature to 200-900 ℃ at the room temperature at the speed of 1-5 ℃/min, keeping the highest temperature for 1-5 h, and naturally cooling to the room temperature in N 2 airflow.
An application of the N-doped Pd-Co bimetallic magnetic catalyst in a furfuryl alcohol preparation process by hydrogenation of furfural, wherein the N-doped Pd-Co bimetallic magnetic catalyst as claimed in any one of claims 1-5 is placed in a stainless steel high-pressure reaction kettle, furfural and solvent are added, hydrogen with a certain pressure is introduced, the reaction time, stirring speed and reaction temperature are set, the reaction temperature is cooled to room temperature after the set time is finished, and a corresponding reduction product is obtained by sampling after the pressure relief of the reaction kettle.
Preferably, the catalyst Pd-Co@N/C, the furfural raw material and the solvent are placed in a stainless steel high-pressure reaction kettle for sealing, the hydrogen reaction pressure is set to be 0.5-3.0 MPa, the reaction temperature is 40-120 ℃, the reaction time is 1-5 hours, and the mixed reaction solution is obtained after the reaction is finished.
Preferably, the catalyst Pd-Co@N/C after catalytic reaction is separated, fully washed to be neutral in water, and freeze-dried for recycling.
Preferably, the furfural reaction raw material solution is one or more of cyclohexane, ethyl acetate, 1,4 dioxane, ethanol, N-dimethylformamide and deionized water.
Compared with the prior art, the invention has the following beneficial technical effects:
The Pd-Co bimetallic magnetic catalyst is prepared by an in-situ synthesis means with simple operation and short synthesis process route, active components of the catalyst are regulated and controlled, the process conditions for preparing furfuryl alcohol by selective hydrogenation of furfural are optimized, a reaction catalytic system for preparing furfuryl alcohol by high-selective hydrogenation of furfural is constructed, and the key problem that the catalyst selectively hydrogenates C=O functional groups and retains C=C double bonds to prepare furfuryl alcohol is effectively solved.
Drawings
FIG. 1 is a chemical reaction scheme for preparing furfuryl alcohol by hydrogenating furfural in the present invention.
Detailed Description
Example 1
In order to further refine an N-doped Pd-Co bimetallic magnetic catalyst, a preparation method and application thereof in a furfuryl alcohol preparation process by furfural hydrogenation, a detailed description of example 1 is presented.
The preparation method of the Pd-Co bimetallic magnetic catalyst comprises the following steps:
s1, mixing 0.03mol of citric acid, 0.03mol of cobalt acetate and 0.001mol of palladium acetate and 80mL of ethanol, heating to 80 ℃ and stirring for 4h to colloid;
S2, drying the gelatinous material in the S1 at 100 ℃ for 24 hours, then placing the gelatinous material in a nitrogen and hydrogen atmosphere for reduction at 600 ℃ for 3 hours, cooling, freeze-drying for 24 hours, grinding and sieving to obtain Pd-Co@N/C.
Examples 2 to 5
The Pd-Co@N/C catalyst prepared by using the Pd-Co bimetallic magnetic catalyst Pd-Co@N/C preparation method adopted in the embodiment 1 is applied to furfuryl alcohol preparation reaction by selective hydrogenation of furfural, and comprises the following steps: 5mg of catalyst, 0.5mmol of furfural and 4mL of ethanol solvent are placed in a high-pressure reaction kettle for sealing, 2MPa of H2 is flushed, the reaction temperature is set to 100 ℃ and kept at 100 ℃ for 6 hours, the stirring speed is 300rpm, after the reaction time is set, the reaction kettle is naturally cooled and depressurized, and then the mixture of the reaction liquid and the catalyst is poured out. Fixing the catalyst in the reaction liquid by using magnetic force, pouring out the clarified reaction liquid, and obtaining the catalyst after reaction.
And (3) carrying out qualitative and quantitative analysis on reaction products in the reaction liquid by adopting nuclear magnetism and GC-MS to obtain the conversion rate of furfural and the selectivity of corresponding furfuryl alcohol products.
TABLE 1 conversion of Furfural and selectivity to corresponding furfuryl alcohol products
The purpose of this example 2-5 is to show the effect of commercial catalysts and the Pd-Co@N/C catalyst prepared on the performance of the furfuryl alcohol prepared by selective hydrogenation of furfural. It can be seen from examples 2-5 that different commercial catalysts and the Pd-Co@N/C prepared have a large influence on the reaction performance of furfuryl alcohol prepared by selective hydrogenation of furfural. Commercial Pd/C, ru/C, rh/C and the like have very high reactivity, the conversion rate of furfural is up to more than 89%, but the selectivity of furfuryl alcohol is lower. The Pd-Co@N/C catalyst provided by the invention has low reactivity, but can generate furfuryl alcohol with high selectivity, and the furfuryl alcohol product B has selectivity as high as 85%.
Examples 6 to 13
The Pd-Co@N/C catalyst prepared by using the Pd-Co bimetallic magnetic catalyst Pd-Co@N/C preparation method adopted in the embodiment 1 is applied to furfuryl alcohol preparation reaction by selective hydrogenation of furfural, and comprises the following steps: 5mg Pd-Co@N/C catalyst, 0.5mmol furfural and 4mL solvent are placed in a high-pressure reaction kettle for sealing, 2MPa of H2 is flushed, the reaction temperature is set to 100 ℃ and kept at 100 ℃ for 2 hours, the stirring speed is 300rpm, after the reaction time is set, the reaction kettle is naturally cooled and depressurized, and then the mixture of the reaction solution and the catalyst is poured out. Fixing the catalyst in the reaction liquid by using magnetic force, pouring out the clarified reaction liquid, and obtaining the catalyst Pd-Co@N/C after reaction.
And (3) carrying out qualitative and quantitative analysis on reaction products in the reaction liquid by adopting nuclear magnetism and GC-MS to obtain the conversion rate of furfural and the selectivity of corresponding furfuryl alcohol products.
TABLE 2 conversion of Furfural and selectivity to corresponding furfuryl alcohol products
The purpose of this example 6-13 was to investigate the effect of different solvents on the performance of the selective hydrogenation of furfuryl alcohol by Pd-Co@N/C catalyst furfural. It can be found from examples 6-13 that the solvent has a large influence on the reaction performance of furfuryl alcohol prepared by selectively hydrogenating the Pd-Co@N/C catalyst furfural. In solvents such as cyclohexane, toluene, 1,4 dioxane, DMF, ethanol, etc., the selectivity of the corresponding B product is as high as 99.9%, but the catalyst has low reactivity in these solvents. Through solvent optimization, water is adopted as a solvent, under milder reaction conditions (2 MPaH, 100 ℃ and 2 hours), the conversion rate of furfural reaches 57.3 percent, and the selectivity of the furfuryl alcohol B corresponding to a target product reaches 88.3 percent.
Examples 14 to 27
The Pd-Co@N/C catalyst prepared by using the Pd-Co bimetallic magnetic catalyst Pd-Co@N/C preparation method adopted in the embodiment 1 is applied to furfuryl alcohol preparation reaction by selective hydrogenation of furfural, and comprises the following steps: 5mg Pd-Co@N/C catalyst, 0.5mmol furfural and 4mL water are placed in a high-pressure reaction kettle for sealing, H2 with the pressure of 0.5-3.0 MPa is flushed, the reaction temperature is set to be 40-120 ℃, the reaction time is set to be 1-5 hours, the stirring speed is 300rpm, and after the reaction time is set, the reaction kettle is naturally cooled and depressurized, and then the mixture of the reaction liquid and the catalyst is poured out. Fixing the catalyst in the reaction liquid by using magnetic force, pouring out the clarified reaction liquid, and obtaining the catalyst Pd-Co@N/C after reaction.
And (3) carrying out qualitative and quantitative analysis on reaction products in the reaction liquid by adopting nuclear magnetism and GC-MS to obtain the conversion rate of furfural and the selectivity of corresponding furfuryl alcohol products.
TABLE 3 conversion of Furfural and selectivity to corresponding furfuryl alcohol products
The purpose of this example 14-27 was to investigate the effect of reaction conditions such as temperature, hydrogen pressure, reaction time on the performance of the selective hydrogenation of furfuryl alcohol using Pd-Co@N/C catalyst furfuraldehyde. It can be found from examples 14-27 that the reaction conditions have a great influence on the reaction performance of furfuryl alcohol prepared by selective hydrogenation of Pd-Co@N/C catalyst furfural. Through optimizing working conditions, under milder reaction conditions (2 MPaH 2, 120 ℃ and 4 hours), the conversion rate of the furfural reaches 99.5 percent, and the selectivity of the furfuryl alcohol B product corresponding to the target product reaches 95.9 percent.
The above is only a preferred example of the present invention and is not intended to limit the present invention. Various modifications and alterations of this invention will become apparent to those skilled in the art, and it is intended to cover all such modifications, equivalents, and alternatives falling within the spirit and principles of this invention.

Claims (4)

1. An N-doped Pd-Co bimetallic magnetic catalyst is characterized in that Co salt, a carbon source, pd salt and an amine source are mixed according to a molar ratio of 30:30:1:30, preparing a bimetallic magnetic catalyst Pd-Co@N/C;
The preparation method comprises the following specific steps:
S1, mixing Co salt, a carbon source, pd salt and an amine source according to a molar ratio of 30:30:1:30 in a solvent, stirring for 2-8 hours at 20-100 ℃ to form a uniform jelly, and drying the formed jelly at 50-120 ℃ to obtain a catalyst precursor Pd-Co-N/C;
S2, heating the catalyst precursor Pd-Co-N/C obtained in the S1 in an inert and hydrogen mixed gas flow to 200-900 ℃ for roasting for 1-5 hours to obtain solid powder, heating and pickling the solid powder in an environment of 50-80 ℃, freeze-drying, grinding and sieving to obtain the Pd-Co bimetallic magnetic catalyst Pd-Co@N/C;
In S1, the anions of the metal Co salt are any one of nitrate ions, sulfate ions, phosphate ions, acetate ions and halogen ions;
the carbon source is any one of glucose, malic acid, tartaric acid, benzoic acid, ascorbic acid, oxalic acid, caffeic acid, salicylic acid and citric acid;
The anions of the metal Pd salt are any one of nitrate ions, chloride ions and sulfate ions;
the amine source is any one of melamine, histidine, ammonium citrate, urea and 1, 2-propylene diamine;
In S1, the solvent is one or a mixture of more of dichloromethane, deionized water, methanol, isopropanol, tetrahydrofuran, dioxane, 2-butanol, chloroform and ethanol.
2. The preparation method of the N-doped Pd-Co bimetallic magnetic catalyst according to claim 1, wherein in S2, the heating and roasting method of the Pd-Co-N/C catalyst precursor is as follows: raising the temperature to 200-900 ℃ at the room temperature at the speed of 1-5 ℃/min, keeping the highest temperature for 1-5 h, and naturally cooling to the room temperature in N 2 airflow.
3. The application of the N-doped Pd-Co bimetallic magnetic catalyst in the furfuryl alcohol preparation process by hydrogenation of furfural is characterized in that the N-doped Pd-Co bimetallic magnetic catalyst as claimed in any one of claims 1-2 is placed in a stainless steel high-pressure reaction kettle, furfural and solvent are added, the reaction pressure of hydrogen is set to be 0.5-3.0 MPa, the reaction temperature is set to be 40-120 ℃ and the reaction time is set to be 1-5 hours, after the set time is finished, the reaction kettle is cooled to room temperature, and the corresponding reduction product is obtained by sampling after the pressure relief of the reaction kettle;
The catalyst Pd-Co@N/C after the catalytic reaction is separated, fully washed to be neutral in water, and freeze-dried for recycling.
4. The application of the N-doped Pd-Co bimetallic magnetic catalyst in the process for preparing furfuryl alcohol by hydrogenating furfural as claimed in claim 3, wherein the raw material solution for the furfural reaction is one or more solvents selected from cyclohexane, ethyl acetate, 1,4 dioxane, ethanol, N-dimethylformamide and deionized water.
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