CN115715979A - Oxidation catalyst, preparation method thereof and application thereof in preparation of 2, 5-furandicarboxylic acid - Google Patents
Oxidation catalyst, preparation method thereof and application thereof in preparation of 2, 5-furandicarboxylic acid Download PDFInfo
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- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 44
- 230000003647 oxidation Effects 0.000 title claims abstract description 38
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- 238000002360 preparation method Methods 0.000 title description 18
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- 238000000034 method Methods 0.000 claims abstract description 44
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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 present disclosure provides a method of preparing an oxidation catalyst, the method of preparing comprising: s1, dipping a carbon-containing material by using a water solution containing a boron element, and performing first roasting in an inert gas to obtain a boron-doped carbon carrier; s2, mixing the boron-doped carbon carrier with an active metal component compound solution to obtain a first mixture; s3, carrying out primary drying and primary reduction on the first mixture. When the oxidation catalyst disclosed by the invention is used for catalytic oxidation of 5-hydroxymethylfurfural, a target product can be obtained in a high-selectivity manner under the condition of no additional alkali auxiliary agent.
Description
Technical Field
The application relates to the field of chemistry and chemical engineering, in particular to an oxidation catalyst, a preparation method thereof and application thereof in preparation of 2, 5-furandicarboxylic acid.
Background
With the consumption of fossil fuels and the impact on the environment, there is a worldwide interest in finding sustainable alternative energy sources and chemicals. Biomass resources are one of the most abundant renewable resources on earth, among which lignocellulose resources, as the most common type of biomass resources, can produce high value-added chemicals through conversion. 5-Hydroxymethylfurfural (HMF) is one of important biomass-based platform compounds, can be prepared by dehydrating fructose, glucose and the like under the catalysis of acid, can obtain 2, 5-furandicarboxylic acid (FDCA) through the catalytic oxidation of 5-hydroxymethylfurfural, has similar chemical structure and physical properties with terephthalic acid, is considered as an ideal substitute of petroleum-based monomer terephthalic acid (PTA), can be subjected to polyester reaction with ethylene glycol to prepare a renewable PEF material, can be applied to the fields of films, packaging soft materials, plastic bottles and the like, and has important practical value.
Preparation of FDCA by selective oxidation of HMFIn the process, it has been reported that the use of a strongly oxidizing agent such as chromate, permanganate or the like, produces FDCA in an equivalent amount by a metered oxidation method, but the oxidizing agent used has drawbacks such as environmental pollution and toxicity. In recent years, some researchers have employed heterogeneous catalysts of noble or non-noble metals, usually in NaOH or Na 2 CO 3 For example, chinese patent document CN 101891719A discloses a method for synthesizing 2, 5-furandicarboxylic acid, in which furan-like substances and alkaline solution are mixed in a mass ratio of 1. Chinese patent document CN 104162422A discloses a method for preparing a basic carbonaceous solid catalyst carrier, which adopts phenolic compounds or saccharides as carbon sources, introduces a certain amount of MgO precursor, and carries noble metal Pt after high-temperature carbonization and acid washing, wherein the yield of FDCA can reach 95% at most, but after the catalyst is used for many times, part of MgO is lost, and the activity of the catalyst is reduced.
Therefore, there is a need in the art for further catalyst activity and cycle stability, increasing 5-hydroxymethylfurfural conversion and selectivity to 2, 5-furandicarboxylic acid.
Disclosure of Invention
The purpose of the disclosure is to provide an efficient and stable supported metal nano-catalyst, and improve the single-pass treatment capacity of 5-hydroxymethylfurfural.
In order to achieve the above object, a first aspect of the present disclosure provides a method of preparing an oxidation catalyst, the method comprising:
s1, dipping a carbon-containing material by using a water solution containing a boron element, and performing first roasting in an inert gas to obtain a boron-doped carbon carrier;
s2, mixing the boron-doped carbon carrier with an active metal component compound solution to obtain a first mixture;
s3, carrying out first drying and first reduction on the first mixture.
Optionally, the carbonaceous material has a specific surface area of 200 to 2000m 2 A/g, preferably from 800 to 1600m 2 (ii)/g; optionally, the carbonaceous material is selected from at least one of activated carbon, carbon black, carbon nanotubes, graphene and graphene oxide, preferably activated carbon and/or carbon black; the mass ratio of the carbon-containing material to the boron element is 120-5:1, preferably 100:1-10:1;
optionally, the aqueous solution containing boron element is selected from boric acid solution and/or borate solution.
Alternatively, the active metal component compound is selected from soluble metal compounds of group VIII metals; optionally, the soluble metal compound of the group VIII metal is at least one of a nitrate, an acetate, a soluble carbonate, a chloride, and a soluble complex of the group VIII metal; the group VIII metal is at least one selected from rhodium element, palladium element, platinum element and ruthenium element; preferably, the active metal component compound is a chloride of a group VIII metal; further preferably, the active metal component compound is ruthenium chloride.
Optionally, the mass fraction of the active metal component element is 1% to 30%, preferably 3% to 20%, based on the mass of the catalyst.
Optionally, in step S1, the impregnation conditions include: the dipping temperature is 15-40 ℃, and the preferred temperature is 20-30 ℃; the dipping time is 12 to 40 hours, preferably 15 to 30 hours; the conditions of the first firing include: the roasting temperature is 300-800 ℃, preferably 450-650 ℃; the roasting time is 0.5 to 10 hours, preferably 2.5 to 7 hours;
in step S2, the mixing is equal-volume dipping mixing; the mixing conditions include: the mixing temperature is 15-40 ℃, preferably 20-30 ℃; the mixing time is 6 to 20 hours, preferably 8 to 16 hours;
in step S3, the conditions of the first drying include: the drying temperature is 60-140 ℃, preferably 100-130 ℃; the drying time is 6-24 hours, preferably 10-18 hours; the conditions of the first reduction include: under a reducing atmosphere containing hydrogen; preferably, the reducing atmosphere contains 10-100% by volume of hydrogen and 0-90% by volume of an inert gas; the reduction temperature is 150-600 ℃, preferably 300-550 ℃; the reduction time is 2 to 6 hours, preferably 3 to 5 hours.
A second aspect of the present disclosure provides an oxidation catalyst comprising a boron-doped carbon support and an active metal component; the boron-doped carbon support has a specific surface area of 200-2500m 2 (ii)/g; in the boron-doped carbon carrier, the mass fraction of boron is 0.01-5 wt%, and the mass fraction of oxygen is 3-15 wt%; the active metal component is present in an amount of 1 to 30 wt% based on the weight of the oxidation catalyst.
Optionally, XPS analyzed B of the boron doped carbon support 1s In the spectrum peak, the spectrum peak has a characteristic peak between 190 and 195 eV.
Alternatively, the active metal component compound is selected from oxides of group VIII metals; preferably, the oxide of the group VIII metal is an oxide of at least one of rhodium, palladium, platinum and ruthenium; further preferably, the oxide of the group VIII metal is an oxide of ruthenium.
A third aspect of the present disclosure provides a method for producing 2, 5-furandicarboxylic acid, comprising:
SS1, mixing the 5-hydroxymethylfurfural aqueous solution with an organic solvent to obtain a mixed solution;
SS2, adding an oxidation catalyst into the mixed solution, and carrying out oxidation reaction in the presence of oxygen;
wherein, the oxidation catalyst is the oxidation catalyst prepared by the preparation method or the oxidation catalyst.
Optionally, the mass ratio of 5-hydroxymethylfurfural to the mixed solution is 1:2-50, preferably 1:5-20 parts of; the volume ratio of the 5-hydroxymethylfurfural aqueous solution to the organic solvent is 1:0.1 to 8, preferably 1:0.5-6, more preferably 1:1-4; the organic solvent is at least one selected from dioxane, N-dimethylformamide, N-dimethylacetamide, tetrahydrofuran, N-dimethyl sulfoxide, pyridine and acetonitrile; the molar ratio of the 5-hydroxymethylfurfural to the active metal components in the oxidation catalyst is 60-350:1, preferably from 100 to 210:1.
alternatively, in step SS2, the oxidation reaction conditions include: the oxygen partial pressure is 0.05MPa-2MPa, preferably 0.5MPa-1MPa; the reaction temperature is 50-170 ℃, and preferably 90-120 ℃; the reaction time is 0.5h-16h, preferably 1h-5h.
Through the technical scheme, the method has the following beneficial effects.
(1) According to the method, the carbon-containing material is subjected to boron doping treatment, the carbon material is used as a carrier to load an active metal component, the activity and the stability of the catalyst can be obviously improved, the high-selectivity 2, 5-furandicarboxylic acid can be obtained through catalytic oxidation under the condition that no alkaline auxiliary agent is added, and the loss of the metal component is not found in the catalyst circulation process.
(2) By carrying out boron doping treatment on the carbon-containing material, the hydrophilicity of the carrier can be improved, on one hand, the active metal component catalyst with higher loading capacity can be obtained, the utilization rate of the active metal can be kept, and the activity of the catalyst can be improved; on the other hand, the method is beneficial to the adsorption of reactants on the surface of the active metal, promotes the heterogeneous catalytic reaction and reduces the occurrence of side reactions. Therefore, the catalyst can promote the catalytic conversion of high-concentration reactants to obtain high-selectivity target products.
(3) According to the method, the catalyst is improved, a mixed system of water and an organic solvent is adopted, an alkaline auxiliary agent is not needed, the post-treatment step of the product is simplified, the condition that a large amount of wastewater is generated in the subsequent acidification process is avoided, and the method is green and environment-friendly and has wide application prospect.
Additional features and advantages of the present disclosure will be set forth in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this specification, illustrate embodiments of the disclosure and together with the description serve to explain the disclosure without limiting the disclosure. In the drawings:
FIG. 1 is an XPS spectrum of a boron doped carbon support of example 1;
FIG. 2 is an XPS spectrum of the boron doped carbon support of example 2;
figure 3 is an XPS spectrum of the boron doped carbon support of example 3.
Detailed Description
Specific embodiments of the present disclosure are described in detail below. It should be understood that the detailed description and specific examples, while indicating the present disclosure, are given by way of illustration and explanation only, not limitation.
A first aspect of the present disclosure provides a method of preparing an oxidation catalyst, the method of preparing comprising:
s1, dipping a carbon-containing material by using a water solution containing a boron element, and performing first roasting in an inert gas to obtain a boron-doped carbon carrier;
s2, mixing the boron-doped carbon carrier with an active metal component compound solution to obtain a first mixture;
s3, carrying out first drying and first reduction on the first mixture.
According to the first aspect of the present disclosure, the carbonaceous material may have a specific surface area of 200 to 2000m 2 A/g, preferably of 800 to 1600m 2 (iv) g; optionally, the carbonaceous material may be selected from at least one of activated carbon, carbon black, carbon nanotubes, graphene and graphene oxide, preferably activated carbon and/or carbon black; the mass ratio of the carbonaceous material to the boron element may be 120-5:1, preferably 100:1-10:1;
according to the first aspect of the present disclosure, the aqueous solution containing the boron element may be selected from a boric acid solution and/or a borate solution.
According to a first aspect of the present disclosure, the active metal component compound may be selected from soluble metal compounds of group VIII metals; optionally, the soluble metal compound of the group VIII metal is at least one of a nitrate, an acetate, a soluble carbonate, a chloride, and a soluble complex of the group VIII metal; the VIII group metal is at least one selected from rhodium element, palladium element, platinum element and ruthenium element; preferably, the active metal component compound is a chloride of a group VIII metal; further preferably, the active metal component compound is ruthenium chloride.
According to the first aspect of the present disclosure, the mass fraction of the active metal component element may be 1% to 30%, preferably 3% to 20%, based on the mass of the catalyst.
According to the first aspect of the present disclosure, in step S1, the conditions of the impregnation may include: the dipping temperature is 15-40 ℃, and the preferable temperature is 20-30 ℃; the dipping time is 12 to 40 hours, preferably 15 to 30 hours; the conditions of the first firing may include: the roasting temperature is 300-800 ℃, preferably 450-650 ℃; the roasting time is 0.5 to 10 hours, preferably 2.5 to 7 hours;
in step S2, the mixing may be isochoric dip mixing; the conditions for the mixing may include: the mixing temperature is 15-40 ℃, preferably 20-30 ℃; the mixing time is 6 to 20 hours, preferably 8 to 16 hours;
in step S3, the conditions of the first drying may include: the drying temperature is 60-140 ℃, preferably 100-130 ℃; the drying time is 6-24 hours, preferably 10-18 hours; the conditions of the first reduction may include: under a reducing atmosphere containing hydrogen; preferably, the reducing atmosphere contains 10 to 100 volume% of hydrogen and 0 to 90 volume% of inert gas; the reduction temperature is 150-600 ℃, preferably 300-550 ℃; the reduction time is 2 to 6 hours, preferably 3 to 5 hours.
According to a specific embodiment of the disclosure, a carbon-containing material is mixed with a boron source aqueous solution, the mixture is dried after being dipped, the dipping time is 12-72 hours, the drying temperature is 70-120 ℃, then the mixture is placed in a tube furnace, the temperature of the tube furnace is raised under the protection of inert gas, the temperature raising rate is 8 ℃/min-15 ℃/min, and then the mixture is processed at a high temperature for a period of time, wherein the processing temperature is 300-800 ℃, preferably 400-600 ℃, and the processing time is 0.5-10 hours, preferably 1-5 hours, so as to obtain the boron-doped carbon carrier disclosed by the disclosure.
Second of the present disclosureAspects provide an oxidation catalyst comprising a boron-doped carbon support and an active metal component; the specific surface area of the boron-doped carbon carrier is 200-2500m 2 (ii)/g; in the boron-doped carbon carrier, the mass fraction of boron is 0.01-5 wt%, and the mass fraction of oxygen is 3-15 wt%; the active metal component is present in an amount of 1 to 30 wt% based on the weight of the oxidation catalyst.
B of XPS analysis of the boron doped carbon support according to a second aspect of the present disclosure 1s Among the spectral peaks, there is a characteristic peak between 190 and 195 eV.
According to a second aspect of the present disclosure, the active metal component compound may be selected from oxides of group VIII metals; preferably, the oxide of the group VIII metal is an oxide of at least one of rhodium, palladium, platinum and ruthenium; further preferably, the oxide of the group VIII metal is an oxide of ruthenium.
A third aspect of the present disclosure provides a method for producing 2, 5-furandicarboxylic acid, comprising:
SS1, mixing the 5-hydroxymethylfurfural aqueous solution with an organic solvent to obtain a mixed solution;
SS2, adding an oxidation catalyst into the mixed solution, and carrying out oxidation reaction in the presence of oxygen;
wherein, the oxidation catalyst is the oxidation catalyst prepared by the preparation method or the oxidation catalyst.
According to the third aspect of the present disclosure, the mass ratio of 5-hydroxymethylfurfural to the mixed solution may be 1:2-50, preferably 1:5-20 parts of; the volume ratio of the 5-hydroxymethylfurfural aqueous solution to the organic solvent may be 1:0.1 to 8, preferably 1:0.5-6, more preferably 1:1-4; the organic solvent can be at least one selected from dioxane, N-dimethylformamide, N-dimethylacetamide, tetrahydrofuran, N-dimethyl sulfoxide, pyridine and acetonitrile; the molar ratio of 5-hydroxymethylfurfural to active metal components in the oxidation catalyst may be from 60 to 350:1, preferably from 100 to 210:1.
according to a third aspect of the present disclosure, in step SS2, the conditions of the oxidation reaction may include: the oxygen partial pressure is 0.05MPa-2MPa, preferably 0.5MPa-1MPa; the reaction temperature is 50-170 ℃, preferably 90-120 ℃; the reaction time is 0.5h-16h, preferably 1h-5h.
The present disclosure is further illustrated by the following examples. The raw materials used in the examples are all available from commercial sources. Wherein the activated carbon is coconut shell carbon, and the source of the manufacturer comprises Beijing university Macro science and technology company, inc. and Kaldo carbon (Suzhou) company, inc. (No. 107C); the carbon Black comprises EC-300J, EC-600JD, ECP-600JD, VXC72 and Black pearls 2000.
Example 1
This example serves to illustrate the preparation of boron doped carbon supports of the present disclosure.
1g of Black pearls 2000 was immersed in 1.7wt% aqueous sodium borate solution (15mL) for 24h; drying in an oven at 100 ℃; then placing the tube furnace into a tube furnace, heating the tube furnace to 500 ℃ at the speed of 8 ℃/min, and carrying out constant temperature treatment for 2h; and naturally cooling to obtain the boron-doped carbon carrier, wherein the number of the boron-doped carbon carrier is carbon carrier A.
The boron mass fraction by XPS analysis is 0.72%; the oxygen mass fraction by XPS analysis was 10.2%; specific surface area 1480m 2 (ii) in terms of/g. Fig. 1 is an XPS spectrum of a boron doped carbon support of example 1.
Example 2
This example serves to illustrate the preparation of boron doped carbon supports of the present disclosure.
Adding 10mL of absolute ethanol into 1g of Ketjenblack ECP600JD, and then adding 25mL of 4wt% sodium borate aqueous solution for soaking for 16h; drying in an oven at 100 ℃; then placing the tube furnace into the tube furnace, heating the tube furnace to 600 ℃ at the speed of 8 ℃/min, and carrying out constant temperature treatment for 3h; and naturally cooling to obtain the boron-doped carbon carrier, which is numbered as carbon carrier B.
The boron mass fraction by XPS analysis is 1.9%; the oxygen mass fraction by XPS analysis was 8.7%; the specific surface area is 1290m 2 (ii) in terms of/g. Figure 2 is an XPS spectrum of the boron doped carbon support of example 2.
Example 3
This example serves to illustrate the preparation of boron doped carbon supports of the present disclosure.
Adding 10mL of absolute ethyl alcohol into 1g of Carlang carbon activated carbon 107C, and then adding 25mL of 5wt% sodium borate aqueous solution for soaking for 24 hours; drying in an oven at 100 ℃; then placing the tube furnace into a tube furnace, heating the tube furnace to 600 ℃ at the speed of 6 ℃/min, and carrying out constant temperature treatment for 4h; and naturally cooling to obtain the boron-doped carbon carrier, wherein the number of the boron-doped carbon carrier is carbon carrier C.
The boron mass fraction of XPS analysis is 2.5%; the oxygen mass fraction by XPS analysis was 9.6%; the specific surface area is 1068m 2 (iv) g. Figure 3 is an XPS spectrum of the boron doped carbon support of example 3.
Example 4
This example serves to illustrate the preparation of the ruthenium on carbon catalyst of the present disclosure.
RuCl is treated by adopting an isovolumetric impregnation method 3 And stirring and soaking the aqueous solution and the carbon carrier A for 12h at room temperature, wherein the mass ratio of the metal Ru to the carbon carrier A in the RuCl3 aqueous solution is 0.1. The mixture was then dried at 120 ℃ for 12h to give a catalyst precursor. The catalyst precursor was placed in a tube furnace at 20 vol% H 2 Per 80% by volume N 2 Reducing for 4 hours at 500 ℃ in the atmosphere to obtain the ruthenium-carbon catalyst with the active component content of 9.6 wt%.
Example 5
This example serves to illustrate the preparation of the ruthenium on carbon catalyst of the present disclosure.
A ruthenium on carbon catalyst was prepared according to the method of example 4, except that: carbon support B prepared in example 2 was used, and RuCl 3 The mass ratio of the metal Ru to the carbon support B in the aqueous solution was 0.25.
Example 6
This example serves to illustrate the preparation of the ruthenium on carbon catalyst of the present disclosure.
A ruthenium on carbon catalyst was prepared according to the method of example 4, except that: carbon support C prepared in example 3 was used, and RuCl 3 The mass ratio of the metal Ru to the carbon support C in the aqueous solution was 0.04 to obtain a ruthenium-carbon catalyst having an active component content of 3.8 wt%.
Example 7
This example serves to illustrate the preparation of a platinum carbon catalyst of the present disclosure.
A platinum carbon catalyst was prepared as in example 4, except that: the carbon support B prepared in example 2 was used, and the metal precursor H was used 2 PtCl 6 And (4) obtaining a platinum-carbon catalyst with the active component content of 9.7wt% by using an aqueous solution.
Example 8
This example serves to illustrate the preparation of the palladium on carbon catalyst of the present disclosure.
A palladium on carbon catalyst was prepared as in example 4, with the only difference that: using the carbon support C prepared in example 3, the metal precursor used PdCl 2 Water solution to obtain the palladium carbon catalyst with the active component content of 9.6 wt%.
Example 9
This example illustrates the process of the present disclosure for the preparation of 2, 5-furandicarboxylic acid.
Adding 1g of 5-hydroxymethylfurfural into a 50mL stainless steel high-pressure reaction kettle, adding 10g of a mixed solvent consisting of water and 1, 4-dioxane (the mass ratio of the water to the 1, 4-dioxane is 1). After the reaction was completed, it was cooled to room temperature. And filtering and washing the reaction solution to collect the reaction solution. And (3) diluting the reaction solution with deionized water, fixing the volume to 100mL, and sampling for high performance liquid chromatography analysis. The results of the catalytic reaction are shown in Table 1.
Example 10
2, 5-Furanedicarboxylic acid was prepared according to the method of example 9, except that the ruthenium-on-carbon catalyst of example 5 was selected as the catalyst and the amount of the catalyst added was 0.022g. The results of the catalytic reaction are shown in Table 1.
Example 11
2, 5-Furanedicarboxylic acid was prepared according to the method of example 9, except that the ruthenium-carbon catalyst of example 6 was selected as the catalyst and the amount of the catalyst added was 0.141g. The catalytic reaction results are shown in table 1.
Example 12
2, 5-Furanedicarboxylic acid was prepared according to the method of example 9, except that the platinum-carbon catalyst of example 7 was selected as the catalyst and the catalyst was added in an amount of 0.108g. The results of the catalytic reaction are shown in Table 1.
Example 13
2, 5-Furancarboxylic acid was prepared according to the method of example 9, except that the palladium on carbon catalyst of example 8 was selected as the catalyst, and the amount of the catalyst added was 0.058g. The results of the catalytic reaction are shown in Table 1.
Example 14
2, 5-Furanedicarboxylic acid was produced according to the method of example 9, except that the reaction solvent was a mixed solvent composed of water and tetrahydrofuran (the mass ratio of water to tetrahydrofuran was 1. The catalytic reaction results are shown in table 1.
Example 15
2, 5-Furancarboxylic acid was prepared according to the method of example 9, except that the mass of the reactant 5-hydroxymethylfurfural was 0.5g, and the reaction time was 3 hours. The catalytic reaction results are shown in table 1.
Comparative example 1
A ruthenium-carbon catalyst was prepared according to the method of example 4, except that Black pearls 2000 was used as the support without doping treatment. Using the catalyst, 2, 5-furandicarboxylic acid was prepared according to the method of example 9, and the results of the catalytic reaction are shown in Table 1.
Comparative example 2
A ruthenium-carbon catalyst was prepared according to the method of example 4, except that the carrier used the carlang carbon activated carbon 107C which was not subjected to the doping treatment. Using the catalyst, 2, 5-furandicarboxylic acid was prepared according to the method of example 9, and the results of the catalytic reaction are shown in Table 1.
Comparative example 3
2, 5-Furancarboxylic acid was prepared according to the method of example 9, except that the reaction solvent was only water. The results of the catalytic reaction are shown in Table 1.
Comparative example 4
A ruthenium carbon catalyst was prepared according to the method of example 4, except that the support was used with karokang carbon activated carbon 107C which was not subjected to doping treatment. Using the catalyst, 2, 5-furandicarboxylic acid was prepared according to the method of comparative example 3, and the results of the catalytic reaction are shown in Table 1.
TABLE 1
In the reaction result, the target product is 2, 5-furandicarboxylic acid, and the intermediate product is partially oxidized 5-formyl-2-furancarboxylic acid. Comparing the results of example 9 with those of comparative examples 1 to 2, it is understood that, in the synthesis of 2, 5-furandicarboxylic acid using 5-hydroxymethylfurfural, the selectivity of 2, 5-furandicarboxylic acid can be significantly improved even in the presence of a high concentration of 5-hydroxymethylfurfural by subjecting a carbon-containing support to boron doping treatment and then using the noble metal catalyst thus obtained. Comparing the results of example 9 with those of comparative examples 3 to 4, it can be seen that the activity of the catalyst can be further improved by using an appropriate organic solvent system.
In addition, the cyclic reaction was carried out according to the method of example 9, the catalyst was recycled for 8 times, the percent conversion of 5-hydroxymethylfurfural was 100%, and the selectivity of 2, 5-furandicarboxylic acid was still substantially maintained at 96%, which indicates that the corresponding catalyst had improved stability and cyclability in the method of the present invention.
The preferred embodiments of the present disclosure have been described above in detail, however, the present disclosure is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present disclosure within the technical idea of the present disclosure, and these simple modifications all belong to the protection scope of the present disclosure.
It should be noted that the various features described in the foregoing embodiments may be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, various possible combinations will not be separately described in this disclosure.
In addition, any combination of various embodiments of the present disclosure may be made, and the same should be considered as the disclosure of the present disclosure as long as it does not depart from the gist of the present disclosure.
Claims (11)
1. A method of preparing an oxidation catalyst, the method comprising:
s1, dipping a carbon-containing material by using a water solution containing a boron element, and performing first roasting in an inert gas to obtain a boron-doped carbon carrier;
s2, mixing the boron-doped carbon carrier with an active metal component compound solution to obtain a first mixture;
s3, carrying out first drying and first reduction on the first mixture.
2. The method of claim 1, wherein the carbonaceous material has a specific surface area of 200-2000m 2 A/g, preferably of 800 to 1600m 2 (ii)/g; optionally, the carbonaceous material is selected from at least one of activated carbon, carbon black, carbon nanotubes, graphene and graphene oxide, preferably activated carbon and/or carbon black;
the mass ratio of the carbon-containing material to the boron element is 120-5:1, preferably 100:1-10:1;
optionally, the aqueous solution containing boron element is selected from a boric acid solution and/or a borate solution.
3. The method of claim 1, wherein the active metal component compound is selected from soluble metal compounds of group VIII metals;
optionally, the soluble metal compound of the group VIII metal is at least one of a nitrate, an acetate, a soluble carbonate, a chloride, and a soluble complex of the group VIII metal; the VIII group metal is at least one selected from rhodium element, palladium element, platinum element and ruthenium element;
preferably, the active metal component compound is a chloride of a group VIII metal;
further preferably, the active metal component compound is ruthenium chloride.
4. A process according to claim 1 or 3, wherein the mass fraction of active metal component elements is from 1% to 30%, preferably from 3% to 20%, based on the mass of the catalyst.
5. The method of claim 1, wherein,
in step S1, the impregnation conditions include: the dipping temperature is 15-40 ℃, and the preferable temperature is 20-30 ℃; the dipping time is 12 to 40 hours, preferably 15 to 30 hours;
the conditions of the first firing include: the roasting temperature is 300-800 ℃, preferably 450-650 ℃; the roasting time is 0.5 to 10 hours, preferably 2.5 to 7 hours;
in step S2, the mixing is equal-volume impregnation mixing; the mixing conditions include: the mixing temperature is 15-40 ℃, preferably 20-30 ℃; the mixing time is 6 to 20 hours, preferably 8 to 16 hours;
in step S3, the conditions of the first drying include: the drying temperature is 60-140 ℃, preferably 100-130 ℃; the drying time is 6-24 hours, preferably 10-18 hours;
the conditions of the first reduction include: under a reducing atmosphere containing hydrogen; preferably, the reducing atmosphere contains 10 to 100 volume% of hydrogen and 0 to 90 volume% of inert gas; the reduction temperature is 150-600 ℃, preferably 300-550 ℃; the reduction time is 2 to 6 hours, preferably 3 to 5 hours.
6. An oxidation catalyst characterized in that,
the oxidation catalyst comprises a boron-doped carbon support and an active metal component;
the specific surface area of the boron-doped carbon carrier is 200-2500m 2 (ii)/g; in the boron-doped carbon carrier, the mass fraction of boron is 0.01-5 wt%, and the mass fraction of oxygen is 3-15 wt%;
the active metal component is present in an amount of 1 to 30 wt% based on the weight of the oxidation catalyst.
7. An oxidation catalyst according to claim 6, wherein the boron doped carbon support has B as analyzed by XPS 1s In the spectrum peak, the spectrum peak has a characteristic peak between 190 and 195 eV.
8. An oxidation catalyst according to claim 6,
the active metal component compound is selected from oxides of group VIII metals;
preferably, the oxide of the group VIII metal is an oxide of at least one of rhodium, palladium, platinum and ruthenium;
further preferably, the oxide of the group VIII metal is an oxide of ruthenium.
9. A method for producing 2, 5-furandicarboxylic acid, comprising:
SS1, mixing the 5-hydroxymethylfurfural aqueous solution with an organic solvent to obtain a mixed solution;
SS2, adding an oxidation catalyst into the mixed solution, and carrying out oxidation reaction in the presence of oxygen;
wherein the oxidation catalyst is an oxidation catalyst prepared by the method for preparing an oxidation catalyst according to any one of claims 1 to 5 or an oxidation catalyst according to any one of claims 6 to 8.
10. The production method according to claim 9,
the mass ratio of the 5-hydroxymethylfurfural to the mixed solution is 1:2-50, preferably 1:5-20 parts of;
the volume ratio of the 5-hydroxymethylfurfural aqueous solution to the organic solvent is 1:0.1 to 8, preferably 1:0.5 to 6, more preferably 1:1-4; the organic solvent is at least one selected from dioxane, N-dimethylformamide, N-dimethylacetamide, tetrahydrofuran, N-dimethyl sulfoxide, pyridine and acetonitrile;
the molar ratio of the 5-hydroxymethylfurfural to the active metal components in the oxidation catalyst is 60-350:1, preferably 100 to 210:1.
11. the process of claim 9, wherein in step SS2, the oxidation reaction conditions include: the oxygen partial pressure is 0.05MPa-2MPa, preferably 0.5MPa-1MPa; the reaction temperature is 50-170 ℃, and preferably 90-120 ℃; the reaction time is 0.5h-16h, preferably 1h-5h.
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