CN112661729A - Application of nitrate-assisted carbon catalytic system in preparation of 2, 5-furandicarboxaldehyde by catalytic conversion of 5-hydroxymethylfurfural - Google Patents
Application of nitrate-assisted carbon catalytic system in preparation of 2, 5-furandicarboxaldehyde by catalytic conversion of 5-hydroxymethylfurfural Download PDFInfo
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Abstract
The invention belongs to the field of carbon catalytic synthesis, and particularly discloses application of a nitrate-assisted carbon catalytic system in preparation of 2, 5-furandicarboxaldehyde by catalytic conversion of 5-hydroxymethylfurfural. The catalytic system is composed of nitrate and nitrogen-doped carbon nano-materials. The nitrogen-doped carbon nano material is prepared by the following method: step 1, dispersing 100-mesh granular corncob powder into heated deionized water, adding magnesium chloride and dicyanodiamine after uniformly mixing, continuously heating, stirring and uniformly mixing, and drying to obtain a precursor; step 2: and (3) calcining the precursor obtained in the step (1) at high temperature under the protection of nitrogen, and performing acid treatment after calcination to obtain the nitrogen-doped carbon material derived from the corncob meal. The nitrate is selected from ferric nitrate, aluminum nitrate and cupric nitrate with the decomposition temperature lower than 250 ℃. The nitrate-assisted nitrogen-doped carbon material catalytic system has the characteristics of low cost, mild reaction, high efficiency and the like, and has good industrial prospect.
Description
Technical Field
The invention relates to the technical field of preparing 2, 5-dimethylfuran by oxidizing 5-hydroxymethylfurfural through carbon catalysis, and in particular relates to a nitrate-assisted nitrogen-doped catalytic system and application thereof in preparing 2, 5-diformylfuran through catalytic oxidation of 5-hydroxymethylfurfural.
Background
With the decreasing of fossil energy, the development of renewable biomass resources with abundant reserves becomes the focus of attention at home and abroad in this year, and particularly, the production of fine chemicals through biomass resources becomes a new research focus. Among the many bio-based chemicals, 2, 5-diformylfuran is an important biomass platform compound. 2, 5-dimethyl acyl furan is one of important products of selective oxidation of 5-hydroxymethyl furfural, has typical chemical properties of aldehyde, 2, 5-furan dicarbaldehyde is not only used as fine chemicals such as medicines, macrocyclic ligands, antifungal agents and the like, but also is an important furan-based polymer monomer, can be used as a cross-linking agent in a polyvinyl alcohol production process, can also be used for manufacturing electronic optical devices, organic fluorescent powder and the like, and is also a raw material for preparing 2, 5-bis (aminomethyl) -furan and Schiff base.
In view of the important role of 2, 5-Diformylfuran (DFF) and its position in the preparation of fine chemicals, the preparation of 2, 5-diformylfuran has been a focus of research. Among them, the preparation of 2, 5-diformylfuran by oxidation of 5-hydroxymethylfurfural (5-HMF) as a raw material is the most active research subject at present. The traditional preparation method of DFF is to directly oxidize 5-HMF such as potassium permanganate, sodium hypochlorite, lead tetraacetate and the like by using an oxidant, but the traditional oxidants have low efficiency, poor selectivity and serious pollution.
Subsequent homogeneous systems replacing the conventional oxidizing agents were followed, Xu et al with Cu (NO)3)2/VOSO4As a catalyst for the Catalysis of 5-HMF, a yield of 99% was obtained (Applied Catalysis A: General,2014,482, 231-. Chernyshev et al use TEMPO catalyst systems to convert 5-HMF to DFF (Tetrahedron Letters 58(2017)3517-3521) in the presence of excess iodine, among other homogeneous catalysts, mainly copper and manganese salts. Although the homogeneous catalyst has high efficiency in catalyzing 5-HMF, the homogeneous catalyst cannot be recovered, is difficult to separate from the product, and has serious pollution. In order to develop a more green catalytic system, researchers are more inclined to develop a high-efficiency heterogeneous catalyst. The homogeneous catalyst mainly comprises a noble metal catalyst and a non-noble metal catalyst. The noble metal catalyst represented by Au, Pt and Ru has good catalytic activity. For example, Cho et Al supported gold on gamma-Al2O3In the above, Au/gamma-Al is prepared2O399% of 5-HMF can be converted to DFF under optimal reaction conditions (Journal of Industrial and Engineering Chemistry, 2013,19: 1056-. Although the catalytic efficiency of the noble metal is high, the noble metal is stable in price and poor in stability, and is not favorable for actual industrial production. Therefore, non-noble metal catalysts, such as manganese-based and iron-based catalysts, which are superior in terms of price, have been developed very rapidly in recent years. Lenzi et al, using metal organic framework Materials (MOFs) as template agent, directly calcining to prepare hollow Fe-Co/C composite catalyst, and reacting with Na2CO3The promotion of DFF was achieved at 99% under an atmosphere of 1MPa of oxygen (Green Chemistry,2016,18: 3152-3157). Zhang et al use activated MnO2Further, a DFF yield of 68.5% was obtained under the conditions of 6.0MPa and 120 ℃ (BioResources,2014,9: 4656-4666). It is pointed out that the non-noble metals such as manganese, iron base and the like are often required to be at high temperature and high pressure (P is more than 1MPa, T is more than 120)C) and the product selectivity is adjusted by using strong alkali and the like.
Therefore, the development of a novel catalytic system which is mild and efficient for the conversion of 5-HMF into DFF is imminent.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a DFF preparation method with mild reaction conditions, high catalytic efficiency and low cost. The nitrate-assisted carbon catalytic system has higher innovation and good industrial application prospect.
In order to achieve the purpose, the invention provides application of a nitrate-assisted carbon catalytic system in preparing 2, 5-furan dicarboxaldehyde by catalytically converting 5-hydroxymethylfurfural.
The technical scheme of the invention is as follows.
An application of a nitrate-assisted carbon catalytic system in catalytic conversion of 5-hydroxymethylfurfural to prepare 2, 5-furandicarboxaldehyde is disclosed, which comprises the following steps:
mixing 5-hydroxymethylfurfural, a solvent and a nitrogen-doped carbon nano material according to the proportion of 1 mmol: 10mL of: (0.05-0.1) g of the mixture is added into a three-neck flask, the mixture is reacted in a gas atmosphere, the temperature is raised to 80-100 ℃, when the temperature reaches a target temperature, (0.5-1) mmol of nitrate is added, and the mixture is reacted for 6-10 hours at a stirring speed of (700-900) rpm, so that 2, 5-furandicarboxaldehyde is prepared;
the nitrate is nitrate with the decomposition temperature lower than 300 ℃;
the carbon material of the nitrate-assisted carbon catalytic system is a nitrogen-doped carbon nanomaterial with a nitrogen doping amount of more than 5%, wherein the content of pyridine nitrogen and pyrrole nitrogen is not less than 3%.
Further, the nitrate comprises one of ferric nitrate, cupric nitrate and aluminum nitrate.
Further, the gas atmosphere is an oxygen or air reaction atmosphere.
Further, the solvent is more than one of 1, 4-dioxane, N, N-dimethylformamide, dimethyl sulfoxide, acetonitrile and toluene.
Further, the preparation method of the nitrogen-doped carbon nanomaterial comprises the following steps:
1) adding corncob powder into warm water at the temperature of 40-60 ℃, stirring and mixing for 20-30 min, adding calcium chloride and dicyanodiamide after the corncob powder is dispersed, continuously stirring to obtain uniform paste, and drying the paste in an oven at the temperature of 110-115 ℃ to obtain a precursor;
2) calcining the precursor for 2-4 h at 700-900 ℃ under the protection of inert gas atmosphere, taking out the product when the temperature of the product is reduced to room temperature, and grinding the product into powder;
3) pickling the powder obtained in the step 2) in 8-12M concentrated hydrochloric acid for 12-16 h, washing with water, filtering, and drying to obtain the nitrogen-doped carbon nanomaterial.
Further, the mass ratio of the corncob meal, the calcium chloride and the dicyanodiamide is 1: (1-4): (1-4).
Furthermore, the mass ratio of the corncob meal to the calcium chloride to the dicyanodiamide is 1:2: 4.
Further, in step 2), the specific conditions of the calcination are as follows: heating the mixture from room temperature to 700-900 ℃ at a heating rate of 4 ℃/min under a nitrogen or argon flow rate of (80-200) mL/min, and then preserving heat for (2-4) h.
Further, in the step 2), the inert gas atmosphere is nitrogen or argon.
The invention has the following advantages:
(1) the reaction condition is mild, and the reaction can be carried out under normal pressure.
(2) The method is green and efficient, the nitrogen-carbon material prepared from the waste biomass (corncob meal) is low in cost and high in catalytic efficiency, and the yield of DFF is up to 90%, so that the method accords with the concept of sustainable development.
(3) The catalytic system provided by the invention has good repeatability.
(4) The nitrate-assisted nitrogen-doped carbon nano-catalysis system has the characteristics of high catalytic activity, simple preparation, stable catalytic performance, low cost and the like, and can selectively oxidize the p-5-hydroxymethylfurfural into the 2, 5-diformylfuran under mild experimental conditions.
Drawings
FIG. 1 is an XRD spectrum analysis chart of nitrogen-doped carbon nano-materials at different calcination temperatures;
fig. 2 is an XPS spectrum of the nitrogen-doped carbon nanomaterial at different calcination temperatures.
Detailed Description
The invention is further illustrated by the following specific examples. It should be understood that the embodiments of the present invention are not limited thereto, and the following examples are only for illustrating the present invention and do not limit the scope of the present invention. Those skilled in the art can change the technical content into equivalent embodiments with equivalent changes, and any equivalent modifications and substitutions of the following embodiments according to the technical essence of the present invention are within the scope of the present invention.
The preparation method of the catalyst in each example:
the nitrogen-doped porous carbon can be prepared by the following method: weighing 2.00g of corncob powder, dispersing the corncob powder in 40mL of deionized water, stirring for one hour under the water bath heating condition of 80 ℃, then adding 4.00g of anhydrous calcium chloride and 4g of urea, continuously stirring for half an hour, and drying for 64 hours in a 120 ℃ drying oven to obtain a precursor; placing the precursor in a high-temperature tube furnace, introducing nitrogen at the rate of 100mL/min, heating to 800 ℃ at the heating rate of 8 ℃/min, calcining for 2h, naturally cooling to room temperature, and grinding to obtain black powder; and (3) putting the black powder into 40mL of concentrated hydrochloric acid with the substance concentration of 12mol/L, stirring for 12 hours, washing, carrying out suction filtration, and drying to obtain the nitrogen-doped carbon nano material. Because the raw material proportions and the firing temperatures of different nitrogen-doped porous carbons are different, hereinafter, different nitrogen-doped carbon nanomaterials NC122-800 are expressed in a unified format, that is: firing at 800 ℃ by using 800, wherein 122 raw materials are oat in mass ratio: anhydrous calcium chloride: urea 1:2:2, and 2, the nitrogen-doped carbon nano material.
As can be seen from the results in fig. 1(a), corncob meal: calcium chloride: when dicyandiamide is 1:2:2, the calcium chloride on the surface is contained in a large amount when calcination is carried out at 800 ℃ for 2 hours under a nitrogen atmosphere and the calcium chloride is not pickled, but after pickling treatment, the calcium chloride on the surface is completely washed away, and NC122-800 has no diffraction peak of the calcium chloride. FIG. 1(b) is an XRD spectrum of the same mixture ratio at different calcination temperatures. Fig. 2 is an XPS plot of the surface nitrogen content of each of the nitrogen-doped materials, and the specific nitrogen content is summarized in table 1.
TABLE-Nitrogen content of Nitrogen-doped carbon nanomaterials at different calcination temperatures
Comparative example 1
0.1260g of 5-hydroxymethyl furfural (1mmol) was dissolved in 10mL of dioxane, 0.2018g of ferric nitrate nonahydrate (0.5mmol) was added, and the mixture was reacted at 80 ℃ and a stirring rate of 900rpm in an air atmosphere for 6 hours to obtain 2, 5-diformylfuran. Analysis of the results by high performance liquid chromatography: the conversion of 5-hydroxymethylfurfural was 15.71%, and the selectivity of 2, 5-diformylfuran was 30.01%. The testing method of the Shimadzu LC-20A high performance liquid chromatograph comprises the following steps: the chromatographic column is Aminex HPX-87H (150 multiplied by 7.8mm), the UV/Vis detector detects 284nm of wavelength, the mobile phase is 0.005M sulfuric acid, the flow rate is 0.8mL/min, the column temperature is 60 ℃, and the content of 5-hydroxymethylfurfural and 2, 5-diformylfuran in the sample is calculated by an external standard method.
Comparative example 2
Dissolving 0.1260g of 5-hydroxymethyl furfural (1mmol) in 10mL of dioxane, adding 0.1000gNC122-800, performing ultrasonic treatment for 20min, and reacting for 6h at 80 ℃ and a stirring speed of 900rpm in an air atmosphere to obtain 2, 5-diformylfuran. The results of the experiment were analyzed by high performance liquid chromatography: the conversion of 5-hydroxymethylfurfural was 5.71%, and the selectivity of 2, 5-diformylfuran was 29.01%.
Comparative example 3
Dissolving 0.1260g of 5-hydroxymethyl furfural (1mmol) in 10mL of dioxane, adding 0.1000: NC120-800, performing ultrasonic treatment for 20min, adding 0.2018g of ferric nitrate nonahydrate (0.5mmol), and reacting at 80 ℃ and 900rpm in air atmosphere for 6h to obtain 2, 5-diformylfuran. Analysis of the results by high performance liquid chromatography: the conversion of 5-hydroxymethylfurfural was 61.71%, and the selectivity to 2, 5-diformylfuran was 59.01%.
Example 1
0.1263g of 5-hydroxymethylfurfural (1mmol) is dissolved in 10mL of dioxane, 0.1001 NC122-700 is added, ultrasonic treatment is carried out for 20min, 0.2020g of ferric nitrate nonahydrate (0.5mmol) is added, and the reaction is carried out for 6 hours at the temperature of 80 ℃ and the stirring speed of 900rpm under the air atmosphere, so as to obtain the 2, 5-diformylfuran. The results of the experiment were analyzed by high performance liquid chromatography: the conversion of 5-hydroxymethylfurfural was 89.84%, and the selectivity to 2, 5-diformylfuran was 90.45%. Compared with the catalytic performance of the carbon material NC120-800 which is not doped with nitrogen in the comparative example 3, the nitrogen-doped NC122-700 has more advantages in the aspect of catalytic conversion of 5-hydroxymethylfurfural, and the NC122-700 not only improves the conversion rate of 5-hydroxymethylfurfural, but also improves the product selectivity. The nitrogen-doped carbon material is beneficial to the conversion of 5-hydroxymethylfurfural. Therefore, a series of different nitrogen-doped carbon materials are prepared continuously, and the catalytic performance of the nitrogen-doped carbon material is further examined.
Example 2
Dissolving 0.1260g of 5-hydroxymethyl furfural (1mmol) in 10mL of dioxane, adding 0.1000g of NC at 122-800800 ℃, performing ultrasonic treatment for 20min, adding 0.2019g of ferric nitrate nonahydrate (0.5mmol), and reacting at 80 ℃ and the stirring speed of 900rpm in an air atmosphere for 6h to obtain the 2, 5-diformylfuran. The results of the experiment were analyzed by high performance liquid chromatography: the conversion of 5-hydroxymethylfurfural was 94.87%, and the selectivity of 2, 5-diformylfuran was 99%. Compared with the performance of NC122-700 with the nitrogen content of 7.89 percent in the comparative example 1, the catalytic performance of NC122-800 with the nitrogen content of 8.05 is further improved, and almost all 5-hydroxymethylfurfural can be directionally converted into 2, 5-diformylfuran.
Example 3
Dissolving 0.1260g of 5-hydroxymethyl furfural (1mmol) in 10mL of dioxane, adding 0.1000NC122-900, performing ultrasonic treatment for 20min, adding 0.2018g of ferric nitrate nonahydrate (0.5mmol), and reacting at 80 ℃ and 900rpm in air atmosphere for 6h to obtain 2, 5-diformylfuran. The results of the experiment were analyzed by high performance liquid chromatography: the conversion of 5-hydroxymethylfurfural was 82.4% and the selectivity to 2, 5-diformylfuran was 81.87%. The catalytic performance of NC122-900 was reduced compared to that of the carbon material of NC122-800, which is related to the relatively low nitrogen content of NC122-900, and it is clear from Table 1 and FIG. 2 that the nitrogen content of the surface of NC122-900 was only 4.53%.
Example 4
Dissolving 0.1260g of 5-hydroxymethyl furfural (1mmol) in 10mL of dioxane, adding 0.1000NC122-1000, performing ultrasonic treatment for 20min, adding 0.2018g of ferric nitrate nonahydrate (0.5mmol), and reacting at 80 ℃ and 900rpm in air atmosphere for 6h to obtain 2, 5-diformylfuran. The results of the experiment were analyzed by high performance liquid chromatography: the conversion of 5-hydroxymethylfurfural was 80.1%, and the selectivity of 2, 5-diformylfuran was 80.9%. Compared with the material calcined at 700 ℃,800 ℃ and 900 ℃, the nitrogen-doped carbon material prepared at 1000 ℃ has the lowest nitrogen content of only 4.50 percent. Correspondingly, the performance of NC-122-800 for catalyzing and converting 5-hydroxymethylfurfural is lower than that of the three materials.
Example 5
Dissolving 0.1260g of 5-hydroxymethyl furfural (1mmol) in 10mL of dioxane, adding 0.1000g of NC122-800, performing ultrasonic treatment for 20min, adding 0.2024g of ferric nitrate nonahydrate (0.5mmol), and reacting at 70 ℃ and 900rpm in air atmosphere for 6h to obtain 2, 5-diformylfuran. The results of the experiment were analyzed by high performance liquid chromatography: the conversion of 5-hydroxymethylfurfural was 88.6%, and the selectivity of 2, 5-diformylfuran was 99.0%.
Example 6
Dissolving 0.1260g of 5-hydroxymethyl furfural (1mmol) in 10mL of dioxane, adding 0.1000g of NC122-800, performing ultrasonic treatment for 20min, adding 0.2019g of ferric nitrate nonahydrate (0.5mmol), and reacting at 90 ℃ and 900rpm in air atmosphere for 6h to obtain 2, 5-diformylfuran. The results of the experiment were analyzed by high performance liquid chromatography: the conversion of 5-hydroxymethylfurfural was 97.2%, and the selectivity of 2, 5-diformylfuran was 90.0%.
Claims (9)
1. An application of a nitrate-assisted carbon catalytic system in catalytic conversion of 5-hydroxymethylfurfural to 2, 5-furandicarboxaldehyde is characterized in that the application method is as follows:
mixing 5-hydroxymethylfurfural, a solvent and a nitrogen-doped carbon nano material according to the proportion of 1 mmol: 10mL of: (0.05-0.1) g of the mixture is added into a three-neck flask, the mixture is reacted in a gas atmosphere, the temperature is raised to 80-100 ℃, when the temperature reaches a target temperature, (0.5-1) mmol of nitrate is added, and the mixture is reacted for 6-10 hours at a stirring speed of (700-900) rpm, so that 2, 5-furandicarboxaldehyde is prepared;
the nitrate is nitrate with the decomposition temperature lower than 300 ℃;
the carbon material of the nitrate-assisted carbon catalytic system is a nitrogen-doped carbon nanomaterial with a nitrogen doping amount of more than 5%, wherein the content of pyridine nitrogen and pyrrole nitrogen is not less than 3%.
2. Use of a nitrate-assisted carbon catalytic system according to claim 1 for the catalytic conversion of 5-hydroxymethylfurfural to 2, 5-furandicarboxaldehyde, wherein the nitrate comprises one of ferric nitrate, cupric nitrate, and aluminum nitrate.
3. Use of the nitrate-assisted carbon catalytic system according to claim 1 for the catalytic conversion of 5-hydroxymethylfurfural to 2, 5-furandicarboxaldehyde, characterized in that the gas atmosphere is an oxygen or air reaction atmosphere.
4. The use of the nitrate-assisted carbocatalysis system of claim 1 for catalytically converting 5-hydroxymethylfurfural to 2, 5-furandicarboxaldehyde, wherein the solvent is one or more of 1, 4-dioxane, N-dimethylformamide, dimethylsulfoxide, acetonitrile, and toluene.
5. The application of the nitrate-assisted carbon catalytic system in the preparation of 2, 5-furandicarboxaldehyde by catalytic conversion of 5-hydroxymethylfurfural according to claim 1, wherein the preparation method of the nitrogen-doped carbon nanomaterial comprises the following steps:
1) adding corncob powder into warm water at the temperature of 40-60 ℃, stirring and mixing for 20-30 min, adding calcium chloride and dicyanodiamide after the corncob powder is dispersed, continuously stirring to obtain uniform paste, and drying the paste in an oven at the temperature of 110-115 ℃ to obtain a precursor;
2) calcining the precursor at 700-900 ℃ for 2-4 h under the protection of inert gas atmosphere, taking out the product when the temperature of the product is reduced to room temperature, and grinding the product into powder;
3) pickling the powder obtained in the step 2) in 8-12M concentrated hydrochloric acid for 12-16 h, washing with water, filtering, and drying to obtain the nitrogen-doped carbon nanomaterial.
6. Use of the nitrate-assisted carbon catalytic system according to claim 5 for the catalytic conversion of 5-hydroxymethylfurfural to 2, 5-furandicarboxaldehyde, characterized in that: the mass ratio of the corncob meal to the calcium chloride to the dicyanodiamide is 1: (1-4): (1-4).
7. The application of the nitrate-assisted carbon catalytic system in the preparation of 2, 5-furandicarboxaldehyde by catalytic conversion of 5-hydroxymethylfurfural according to claim 5, wherein the mass ratio of corncob meal, calcium chloride and dicyanodiamide is 1:2: 4.
8. Use of the nitrate-assisted carbon catalytic system according to claim 5 for the catalytic conversion of 5-hydroxymethylfurfural to 2, 5-furandicarboxaldehyde, characterized in that in step 2), the calcination is carried out under the following specific conditions: under the flow rate of nitrogen or argon gas of (80-200) mL/min, with the flow rate of 4oHeating the mixture from room temperature to 700-900 ℃ at the temperature rising rate of C/min, and then preserving heat for 2-4 hours.
9. Use of the nitrate-assisted carbon catalytic system according to claim 5 for the catalytic conversion of 5-hydroxymethylfurfural to 2, 5-furandicarboxaldehyde, characterized in that in step 2), the inert gas atmosphere is nitrogen or argon.
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| CN113559930A (en) * | 2021-07-26 | 2021-10-29 | 南京林业大学 | Preparation method and application of solid catalyst taking sodium lignosulfonate as carrier |
| CN113800509A (en) * | 2021-10-11 | 2021-12-17 | 安徽工业大学 | Method for preparing high-nitrogen-doped graphitized porous carbon material by metal nitrate catalytic carbonization method |
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| CN109174153A (en) * | 2018-09-11 | 2019-01-11 | 中南民族大学 | Nitrogen-doped carbon material catalyst and its application in 2,5- diformyl furans is prepared in catalysis 5 hydroxymethyl furfural oxidation |
| CN110452193A (en) * | 2019-07-29 | 2019-11-15 | 中国科学技术大学 | The method that 2,5- furans dicarbaldehyde is prepared by 5 hydroxymethyl furfural |
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| CN101823705A (en) * | 2009-03-04 | 2010-09-08 | 南京大学 | Method for preparing high-surface-area nitrogenous mesoporous carbon material |
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| CN113559930A (en) * | 2021-07-26 | 2021-10-29 | 南京林业大学 | Preparation method and application of solid catalyst taking sodium lignosulfonate as carrier |
| CN113559930B (en) * | 2021-07-26 | 2023-05-23 | 南京林业大学 | Preparation method and application of solid catalyst taking sodium lignin sulfonate as carrier |
| CN113800509A (en) * | 2021-10-11 | 2021-12-17 | 安徽工业大学 | Method for preparing high-nitrogen-doped graphitized porous carbon material by metal nitrate catalytic carbonization method |
| CN113800509B (en) * | 2021-10-11 | 2024-02-06 | 安徽工业大学 | Method for preparing high-nitrogen-doped graphitized porous carbon material by metal nitrate catalytic carbonization method |
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