CN111072601B - Method for preparing 2, 5-furan dicarbaldehyde from 5-hydroxymethylfurfural - Google Patents
Method for preparing 2, 5-furan dicarbaldehyde from 5-hydroxymethylfurfural Download PDFInfo
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- 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
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- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
- B01J23/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
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Abstract
The invention relates to a method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethylfurfural, in particular to Anderson type CeCu (OH) 6 Mo 6 O 18 A method for preparing 2, 5-furan Dicarbaldehyde (DFF) by catalyzing 5-hydroxymethyl furfural (HMF) to be oxidized by using heteropolyacid salt as a catalyst, and comprises the following steps: 1) Adding HMF 0.0504 g into 7 mL aromatic hydrocarbon solvent solution, stirring, adding (40-120 mg) Anderson type heteropoly acid salt CeCu (OH) 6 Mo 6 O 18 Catalyst, 2) introducing oxygen at 110-150 deg.C o Performing HMF oxidation reaction at the temperature of C to obtain mixed liquid containing DFF, 3) diluting the mixed liquid and analyzing the product by using a high performance liquid chromatograph, 4) the process can not only efficiently synthesize DFF (the yield is up to 99 percent), but also has mild reaction conditions and recycled catalyst, thus being a cheap and efficient DFF preparation method. Moreover, the catalyst used in the present invention has a higher selectivity for DFF and is more economical than the catalysts of the prior art.
Description
Technical Field
The invention relates to the technical field of catalysts, and in particular relates to a method for preparing 2, 5-furan diformaldehyde by catalyzing 5-hydroxymethylfurfural to be oxidized.
Background
Biomass is an accessible and renewable non-fossil carbon source that is self-contained as one of the most likely new energy sources to replace fossil fuels and organic molecules. 5-Hydroxymethylfurfural (HMF) is an important intermediate for linking biomass resources with fossil carbon sources, and the research thereof has attracted great attention. HMF can synthesize many high value-added chemical materials, such as 2, 5-furandicarboxylic acid (FDCA) and 2, 5-formylfuran (DFF), among others.
Due to their unique dialdehyde characteristics, DFF has been widely used to synthesize a variety of useful compounds, including drug intermediates, antifungals, organic conductors, macrocyclic ligands, furan resins, and the like. Thus, the selective oxidation of HMF to DFF is a valuable route, requiring the oxidation of its only primary hydroxyl group. Despite the many exciting catalytic processes, such as dehydration, hydrogenation, dehydrogenation, decarbonylation, and decarboxylation, the catalytic oxidative conversion of HMF to DFF remains a formidable challenge because it produces a variety of byproducts, such as 5-hydroxymethyl-2-furancarboxylic acid (HMFCA), 5-formyl-2-furancarboxylic acid (FFCA), and 2, 5-furandicarboxylic acid (FDCA), among others.
To this end, researchers have developed a variety of different catalysts for the reaction of HMF oxidation to produce DFF. For example, walt et al reported a homogeneous catalyst Co (II)/Mn (II)/Zr (II) -Br 2 99.7% conversion of HMF and 61% selectivity of DFF in acetic acid solvent at 70 bar oxygen pressure were obtained. However, the use of acidic media can corrode the reaction kettle to some extent. In addition, homogeneous catalyst systems inevitably suffer from catalyst/product separation. In contrast, the use of heterogeneous catalysts has a number of advantages, including a wide range of operating conditions (temperature, pressure), a high degree of industrial applicability, ease of separation and recovery, etc. Moreau et al report a mixed oxide (V) 2 O 5 / TiO 2 ) The heterogeneous catalyst of (3) can obtain 85% yield of DFF in toluene solution at 363K and 1.6 MPa of air pressure. Recently, nie et al have developed a heterogeneous catalyst, activated carbon-supported ruthenium (Ru/C) catalyst, which is an effective and stable catalyst in the oxidation of HMF at 383K and 2.0 MPa O 2 Higher yields of DFF (96%) were obtained in toluene. Although this system achieves higher DFF yields under milder conditions, the use of the noble metal ruthenium limits its further applications.
Although 2, 5-furan dicarbaldehyde can be obtained by catalytic oxidation of 5-hydroxymethylfurfural, no economical, reasonable and efficient catalytic oxidation preparation method exists at present.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a method for catalytic oxidation of 5-hydroxymethylfurfural to 2, 5-diformylfuran by a heterogeneous and efficient catalyst.
A method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethyl furfural comprises the following steps:
1) Adding Ce (NH) 4 ) 2 (NO 3 ) 6 Is added dropwise to (NH) 4 ) 4 Cu(OH) 6 Mo 6 O 18 Aqueous solution of Ce (NH) 4 ) 2 (NO 3 ) 6 And (NH) 4 ) 4 Cu(OH) 6 Mo 6 O 18 The molar ratio of (1) to (3) is more than 1, preferably 1.5 to 20, then the mixture is stirred at room temperature for reaction for 0.5 to 3 hours to obtain yellow precipitate, and the prepared yellow precipitate is filtered and dried to obtain Anderson type heteropoly acid salt CeCu (OH) 6 Mo 6 O 18 A catalyst;
2) Adding 5-Hydroxymethylfurfural (HMF) into an excessive aromatic hydrocarbon solvent, stirring and mixing uniformly, and then adding the Anderson type heteropolyacid salt CeCu (OH) prepared in the step 1) 6 Mo 6 O 18 The catalyst is the reaction solution, wherein, HMF and CeCu (OH) 6 Mo 6 O 18 The mass ratio of (1): (0.8 to 2.4);
3) Then continuously introducing oxygen into the reaction solution in the step 2) for 6 to 10 hours at the flow rate of 15 to 25 mL/min, and controlling the reaction temperature to be 110 to 150 o Performing HMF oxidation reaction at the temperature of C to obtain a mixed liquid containing 2, 5-furan Dicarbaldehyde (DFF).
Preferably, the aromatic hydrocarbon solvent is p-chlorotoluene or toluene.
Preferably, the mixed liquid containing DFF in the step 3) is kept stand until layering, the upper layer solution is decanted to obtain a solvent solution containing DFF, and the lower layer solution is CeCu (OH) 6 Mo 6 O 18 Washing the lower layer solution with diethyl ether for 3 to 5 times, and drying at 60 to 80 ℃ for 5 to 10 hours to obtain the recovered CeCu (OH) 6 Mo 6 O 18 A catalyst.
The Anderson type heteropoly acid salt CeCu (OH) prepared by the method 6 Mo 6 O 18 。
The Anderson type heteropolyacid salt CeCu (OH) 6 Mo 6 O 18 The use of, i.e., anderson type heteropolyacid salts CeCu (OH) 6 Mo 6 O 18 Application toA catalyst for preparing 2, 5-diformylfuran by oxidizing 5-hydroxymethylfurfural.
The key point of the invention lies in utilizing the novel Anderson type heteropoly acid salt CeCu (OH) 6 Mo 6 O 18 Biological oxidation of 5-hydroxymethylfurfural to 2, 5-diformylfuran, i.e., selective oxidation and O of 5-hydroxymethylfurfural 2 An Electron Transfer Medium (ETM) is added between the catalyst and the oxidant, the Electron Transfer Medium (ETM) can carry electrons to transfer from the catalyst to the oxidant along a low-energy path by reducing the activation energy of the reaction, and furthermore, the electron transfer medium is counter ion Ce of heteropoly acid 4+ By Mo of heteropolyacid catalysts 5+ Species are transported along low energy pathways to oxidants to promote the reaction process and result in HMF being readily oxidized to DFF, in particular, by Mo 5+ One electron of the species is transferred to Ce 4+ Speciation of activated Mo 6+ Species, then activated Mo 6+ Oxidation of HMF to DFF, and finally Ce 3+ Oxidation of species by oxygen to Ce 4+ One cycle is completed. Furthermore, the test showed that CeCu (OH) 6 Mo 6 O 18 Preparation of 2, 5-diformylfuran by catalytic oxidation of 5-hydroxymethylfurfural at a specific temperature of 110-150 DEG C o C. Specific solvents chlorotoluene or toluene, 5-hydroxymethylfurfural and CeCu (OH) 6 Mo 6 O 18 Under the condition of a specific mass ratio (1: 0.8-2.4), the conversion rate of HMF can reach 99%, and the yield of DFF reaches 99%.
The beneficial effects of the invention are:
the present invention provides a new catalyst, namely Anderson type heteropoly acid salt CeCu (OH) 6 Mo 6 O 18 The catalyst can be effectively applied to the preparation of 2, 5-diformylfuran from 5-hydroxymethylfurfural.
The invention provides a technical route for preparing 2, 5-diformylfuran by catalyzing and oxidizing 5-hydroxymethylfurfural with a new catalyst, namely CeCu (OH) 6 Mo 6 O 18 A process for the catalytic oxidation of 5-hydroxymethylfurfural to 2, 5-diformylfuran with a catalyst.
In addition, the technological process of the invention not only can efficiently synthesize DFF (the yield is as high as 99%), but also has mild reaction conditions, and the catalyst can be recycled, thus the method is a cheap and efficient method for preparing DFF.
Meanwhile, the method has the advantages of simple operation of the process, high selectivity and low cost, provides reference for the conversion of renewable biomass resources, and has important significance for the development of novel renewable energy sources.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention. There is shown in the drawings, and herein will be described in detail, preferred embodiments of the invention with the understanding that those skilled in the art can modify the invention described herein without departing from the spirit and the scope of the invention. Accordingly, the following description should be construed as broadly as possible to those skilled in the art and not as limiting the invention.
Further, in the interest of clarity, not all features of an actual implementation are described. In the following description, well-known functions or constructions are not described in detail since they would obscure the invention in unnecessary detail. It will of course be appreciated that in the development of any such actual embodiment, numerous implementation-specific details are set forth in order to achieve the developer's specific goals.
CeCu(OH) 6 Mo 6 O 18 Preparation examples of (1)
(1) Preparation of Cu (II) polyanions (NH) 4 ) 4 Cu(OH) 6 Mo 6 O 18 ：
Dropwise adding CuSO 4 •5H 2 O（3×10 -3 mol) of a mixed aqueous solution (20 cm) 3 ) Boiling aqueous heptamolybdic acid solution (wherein the heptamolybdic acid is 80 cm) 3 The amount of water in (A) is 4.2X 10 -3 mol), the resulting solution is refluxed for 10min, and the resulting yellow insoluble precipitate is filtered off while hot.
Transferring the filtrate to a culture dish, standing for 12h to form light blue crystals, and collecting the crystalsFiltering and vacuum drying at 60 deg.C for 8 hr to obtain (NH) 4 ) 4 Cu(OH) 6 Mo 6 O 18 。
（2）CeCu(OH) 6 Mo 6 O 18 Was prepared as follows:
excess of Ce (NH) 4 ) 2 (NO 3 ) 6 Is added dropwise to (NH) 4 ) 4 Cu(OH) 6 Mo 6 O 18 In an aqueous solution and stirred at room temperature, wherein, ce (NH) 4 ) 2 (NO 3 ) 6 And (NH) 4 ) 4 Cu(OH) 6 Mo 6 O 18 The molar ratio of (a) to (b) is more than 1, preferably 1.5 to 10. After 1 hour, the resulting yellow precipitate was filtered and collected. The precipitated product was dried in vacuo at 60 ℃ for 8 hours to obtain CeCu (OH) 6 Mo 6 O 18 。
Examples 1-9 described below all used the CeCu (OH) prepared by the above example 6 Mo 6 O 18 Is a catalyst.
Example 1
The method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethylfurfural comprises the following steps:
(1) Add 0.0504 g HMF to 7 mL p-chlorotoluene solution, stir and add 40 mg CeCu (OH) 6 Mo 6 O 18 Catalyst at 110 o Continuously introducing oxygen (20 mL/min,8 h) under C, and carrying out HMF oxidation reaction to obtain a mixed liquid;
(2) The mixture was diluted with the same solvent and analyzed by high performance liquid chromatography, and the product type was identified using the standard solution, which indicated that the conversion of HMF was 33% and the yield of DFF reached 33%.
Indicating that HMF reacts with oxygen due to CeCu (OH) 6 Mo 6 O 18 Acts as a catalyst, but at 110 o At C, the optimum catalytic temperature was not reached and the DFF yield was not high, only 33%.
Example 2
The method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethylfurfural comprises the following steps:
(1) 0.0504 g HMF was added to 7 mL p-chlorotoluene solution, after stirring, 40 mg CeCu (OH) was added 6 Mo 6 O 18 Catalyst at 120 o Continuously introducing oxygen (20 mL/min,8 h) under C to perform HMF oxidation reaction to obtain a mixed liquid;
(2) The mixture was diluted with the same solvent and analyzed by high performance liquid chromatography, and the product type was identified using the standard solution, which indicated that the conversion of HMF was 39% and the yield of DFF reached 39%.
To illustrate that HMF reacts with oxygen due to CeCu (OH) 6 Mo 6 O 18 Functions as a catalyst, but at 120 o At C, the optimum catalytic temperature was not reached and the DFF yield was not high, only 39%.
Example 3
The method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethylfurfural comprises the following steps:
(1) 0.0504 g HMF was added to 7 mL p-chlorotoluene solution, after stirring, 40 mg CeCu (OH) was added 6 Mo 6 O 18 Catalyst at 130 o Continuously introducing oxygen (20 mL/min,8 h) under C, and carrying out HMF oxidation reaction to obtain a mixed liquid;
(2) The mixture was diluted with the same solvent and analyzed by high performance liquid chromatography, and the kind of the product was identified by using a standard solution, showing that the conversion of HMF was 53% and the yield of DFF reached 53%.
To illustrate that HMF reacts with oxygen due to CeCu (OH) 6 Mo 6 O 18 Acts as a catalyst, at 130 o The DFF yield was 53% at C.
Example 4
The method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethylfurfural comprises the following steps:
(1) Add 0.0504 g HMF to 7 mL p-chlorotoluene solution, stir and add 40 mg CeCu (OH) 6 Mo 6 O 18 Catalyst at 140 o C, continuously introducing oxygen (20 mL/min,8 h)Carrying out HMF oxidation reaction to obtain mixed liquid;
(2) The mixture was diluted with the same solvent and analyzed by high performance liquid chromatography, and the product type was identified using the standard solution, which indicated that the conversion of HMF was 56% and the yield of DFF reached 52%.
To illustrate that HMF reacts with oxygen due to CeCu (OH) 6 Mo 6 O 18 Functions as a catalyst, however, at 140 o C, too high a reaction temperature decomposes HMF, so that a lower DFF yield is obtained.
Example 5
The method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethyl furfural comprises the following steps:
(1) 0.0504 g HMF was added to 7 mL p-chlorotoluene solution, after stirring, 40 mg CeCu (OH) was added 6 Mo 6 O 18 Catalyst at 150 o Continuously introducing oxygen (20 mL/min,8 h) under C to perform HMF oxidation reaction to obtain a mixed liquid;
(2) The mixture was diluted with the same solvent and analyzed by high performance liquid chromatography, and the kind of the product was identified by using a standard solution, showing that the conversion of HMF was 76% and the yield of DFF reached 46%.
To illustrate that HMF reacts with oxygen due to CeCu (OH) 6 Mo 6 O 18 Functions as a catalyst, however, at 150 o C, too high a reaction temperature decomposes HMF, and therefore a low DFF yield is obtained.
Example 6
The method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethylfurfural comprises the following steps:
(1) Adding HMF 0.0504 g into 7 mL p-chlorotoluene solution, stirring, and adding CeCu (OH) 20 mg 6 Mo 6 O 18 Catalyst at 130 o Continuously introducing oxygen (20 mL/min,8 h) under C to perform HMF oxidation reaction to obtain a mixed liquid;
(2) The mixture was diluted with the same solvent and analyzed by HPLC, and the product type was identified as a standard solution, indicating that the conversion of HMF was 25% and the yield of DFF reached 25%.
To illustrate that HMF reacts with oxygen due to CeCu (OH) 6 Mo 6 O 18 Functioning as a catalyst, the amount of catalyst used was 20 mg, and 25% DFF yield was obtained because of the decrease in the amount of the catalyst active species.
Example 7
The method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethyl furfural comprises the following steps:
(1) Adding HMF 0.0504 g into p-chlorotoluene 7 mL, stirring, and adding CeCu 80 mg (OH) 6 Mo 6 O 18 Catalyst at 130 o Continuously introducing oxygen (20 mL/min,8 h) under C, and carrying out HMF oxidation reaction to obtain a mixed liquid;
(2) The mixture was diluted with the same solvent and analyzed by high performance liquid chromatography, and the product species were identified using the standard solution, showing that the conversion of HMF was 80% and the yield of DFF reached 80%.
Indicating that HMF reacts with oxygen due to CeCu (OH) 6 Mo 6 O 18 When the amount of the catalyst used was 80 mg, the yield of DFF was 80% because the amount of the active material was increased.
Example 8
The method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethyl furfural comprises the following steps:
(1) Adding HMF 0.0504 g into p-chlorotoluene 7 mL, stirring, and adding CeCu 120 mg (OH) 6 Mo 6 O 18 Catalyst at 130 o Continuously introducing oxygen (20 mL/min,8 h) under C, and carrying out HMF oxidation reaction to obtain a mixed liquid;
(2) The mixture was diluted with the same solvent and analyzed by high performance liquid chromatography, and the product species were identified using the standard solution, showing that the conversion of HMF was 99% and the yield of DFF reached 99%.
Indicating that HMF reacts with oxygen due toCeCu(OH) 6 Mo 6 O 18 Functioning as a catalyst, the catalyst amount was 120 mg, and 99% DFF yield was obtained because the amount of the catalyst active material was further increased.
Example 9
(1) 0.0504 g HMF was added to 7 mL toluene solution, stirred and 40 mg CeCu (OH) was added 6 Mo 6 O 18 Catalyst at 110 o Continuously introducing oxygen (20 mL/min,8 h) under C, and carrying out HMF oxidation reaction to obtain a mixed liquid;
(2) The mixture was diluted with the same solvent and analyzed by high performance liquid chromatography, and the product species were identified by using the standard solution, which indicated that the conversion of HMF was 15% and the yield of DFF reached 14%.
To illustrate that HMF reacts with oxygen due to CeCu (OH) 6 Mo 6 O 18 In toluene solution, it acts as a catalyst. Thus, a yield of 14% DFF in toluene solution was obtained.
Examples 1-9 the results of the tests demonstrate CeCu (OH) 6 Mo 6 O 18 The catalytic oxidation of 5-hydroxymethyl furfural to prepare 2, 5-diformylfuran is effective. CeCu (OH) 6 Mo 6 O 18 By coupling redox systems and Electron Transfer Mediators (ETMs) through the transfer of electrons from Mo 5+ The species are transported along low energy pathways to the oxidizing agent to facilitate the reaction process and result in the facile oxidation of HMF to DFF. CeCu (OH) 6 Mo 6 O 18 The catalyst plays a role in the reaction process of preparing 2, 5-diformylfuran by oxidizing 5-hydroxymethylfurfural 5+ One electron of the species is transferred to Ce 4+ Speciation of activated Mo 6+ Species, then activated Mo 6+ Oxidation of HMF to DFF, and finally Ce 3+ Oxidation of species by oxygen to form Ce 4+ One cycle is completed.
Furthermore, at a specific temperature of 110-150 deg.C o C. The solvent is chlorotoluene, 5-hydroxymethyl furfural and CeCu (OH) 6 Mo 6 O 18 Hmf conversion as in examples 7 and 8, with specific mass ratios (1The rate can reach 99%, and the yield of DFF reaches 99%.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and should not be taken as limiting the scope of the present invention, which is intended to cover any modifications, equivalents, improvements, etc. within the spirit and scope of the present invention.
Claims (4)
1. A method for preparing 2, 5-furan dicarboxaldehyde by oxidizing 5-hydroxymethylfurfural is characterized by comprising the following steps:
1) Adding Ce (NH) 4 ) 2 (NO 3 ) 6 Is added dropwise to (NH) 4 ) 4 Cu(OH) 6 Mo 6 O 18 Aqueous solution of Ce (NH) 4 ) 2 (NO 3 ) 6 And (NH) 4 ) 4 Cu(OH) 6 Mo 6 O 18 The molar ratio of the component (a) to the component (b) is more than 1, then the mixture is stirred and reacts for 0.5 to 3h at room temperature to obtain yellow precipitate, and the prepared yellow precipitate is filtered and dried to obtain Anderson type heteropoly acid salt CeCu (OH) 6 Mo 6 O 18 A catalyst;
2) Adding 5-hydroxymethylfurfural into excessive aromatic hydrocarbon solvent, stirring and mixing uniformly, and then adding the Anderson type heteropoly acid salt CeCu (OH) prepared in the step 1) 6 Mo 6 O 18 The catalyst is the reaction solution, wherein, the 5-hydroxymethyl furfural and the CeCu (OH) 6 Mo 6 O 18 The mass ratio of (1): 0.8 to 2.4, wherein the aromatic hydrocarbon solvent is p-chlorotoluene or toluene;
3) Then continuously introducing oxygen into the reaction solution in the step 2) for 6 to 10 hours at the flow rate of 15 to 25 mL/min, and controlling the reaction temperature to be 110 to 150 o And (3) carrying out oxidation reaction of 5-hydroxymethylfurfural at the temperature of C to obtain a mixed liquid containing 2, 5-furandicarboxaldehyde.
2. The method according to claim 1, wherein the mixed liquid containing 2, 5-furandicarboxaldehyde in the step 3) is allowed to stand for layering, and the upper layer solution is decanted to obtain a solvent solution containing 2, 5-furandicarboxaldehyde, and the lower layer solution is CeCu (OH) 6 Mo 6 O 18 CatalysisWashing the lower layer solution with ether for 3 to 5 times, and drying at 60 to 80 ℃ for 5 to 10 hours to obtain the recovered CeCu (OH) 6 Mo 6 O 18 A catalyst.
3. The Anderson-type heteropolyacid salt CeCu (OH) produced by the process as claimed in claim 1 6 Mo 6 O 18 。
4. The Anderson-type heteropolyacid salt CeCu (OH) as claimed in claim 3 6 Mo 6 O 18 Characterized in that the Anderson type heteropolyacid salt CeCu (OH) 6 Mo 6 O 18 The catalyst is applied to the preparation of 2, 5-diformylfuran by oxidizing 5-hydroxymethylfurfural.
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| 3D Flower-like Micro/Nano Ce–Mo Composite Oxides as Effective Bifunctional Catalysts for One-Pot Conversion of Fructose to 2,5-Diformylfuran;Zhenzhen Yang;《ACS Sustainable Chemistry & Engineering》;20170329;第5卷(第5期);第4179-4187页 * |
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