CN111939953B - Preparation method of MXene-based catalyst for preparing furfural with high selectivity - Google Patents
Preparation method of MXene-based catalyst for preparing furfural with high selectivity Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 43
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 239000006185 dispersion Substances 0.000 claims abstract description 37
- 239000007788 liquid Substances 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 25
- -1 1-butyl-3-methylimidazolium tetrafluoroborate Chemical compound 0.000 claims abstract description 12
- 239000011148 porous material Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000001132 ultrasonic dispersion Methods 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 8
- 239000012263 liquid product Substances 0.000 abstract description 11
- 238000000197 pyrolysis Methods 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 7
- 239000002028 Biomass Substances 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000012075 bio-oil Substances 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000007233 catalytic pyrolysis Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000010902 straw Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000010828 animal waste Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- B01J35/647—
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/20—Carbon compounds
- B01J27/22—Carbides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0254—Nitrogen containing compounds on mineral substrates
-
- B01J35/651—
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention discloses a preparation method of an MXene-based catalyst for preparing furfural with high selectivity. The method mainly comprises the following steps: multilayer titanium carbide MXene was dispersed in water to obtain a dispersion A. Chloroiridic acid was added to the dispersion liquid a, and 1-butyl-3-methylimidazolium tetrafluoroborate was added while performing ultrasonic dispersion to obtain a dispersion liquid B. Adjusting the pH value of the dispersion liquid B to 10-12, reacting for 1-5 h, then filtering, washing and drying to obtain a dispersion liquid B with the surface alkaline constant Kb and the acid constant Ka in a ratio of 1.0-2.0: MXene-based catalyst with 1,30-250 nm pore diameter structure. The method synthesizes the MXene-based catalyst for preparing the furfural with high selectivity by using the chloroiridic acid as an active metal raw material and the layered MXene as a catalyst framework, and has the advantages of simple preparation process, high furfural selectivity and yield in biomass pyrolysis liquid products, easiness in large-scale production and the like.
Description
Technical Field
The invention belongs to the technical field of biomass recycling, and particularly relates to a preparation method of an MXene-based catalyst for preparing furfural with high selectivity.
Background
The technology for preparing high-quality bio-oil by biomass rapid catalytic pyrolysis can realize the preparation of chemicals and liquid fuels, and is considered to be one of effective ways for realizing fossil energy substitution. However, the bio-oil has the defects of complex components, high oxygen content, difficult separation and the like, and can be used as alternative fuel after catalytic upgrading. To improve bio-oil yield and target product selectivity, it is important to select a suitable catalyst. Microporous (such as ZSM-5, Y-type and type zeolite, etc.) and mesoporous molecular sieves (such as MCM-41, MSU, SBA-15, etc.) are ideal catalysts for preparing aromatic hydrocarbon by catalytic rapid thermal cracking due to the advantages of regular pore channel structures, good hydrothermal stability, proper acidity, ideal shape-selective catalytic selectivity, etc. In some researches, modification researches are carried out on rice straw pyrolysis oil steam by using HZSM-5 as a catalyst and adopting a fluidized bed pyrolysis and fixed bed catalytic device. As a result, it was found that the bio-oil yield was reduced from 28.5% to 7.2% after passing the oil vapor through the catalyst bed, and the oxygen content was correspondingly reduced from 40.2% to 14.5%. In addition, the catalytic pyrolysis research of pine sawdust is carried out by respectively using P-type, Y-type, mordenite and ZSM-5 as catalysts. The results show that the components of the bio-oil are greatly influenced by the structure and acidity of the zeolite molecular sieve, the bio-oil ketones and polycyclic aromatic hydrocarbon compounds obtained by using the ZSM-5 catalyst are increased, and the acids and alcohols are reduced; as acid sites increase, oil yield decreases and water and aromatic heterocyclic compounds increase. But the single micropore structure of the microporous molecular sieve leads to overlarge mass transfer resistance in the reaction process, thereby not only limiting the reaction rate and the effective utilization of active sites, but also increasing carbon deposition in the reaction process. The deactivation of the carbon deposition of the catalyst is a selective catalytic process with acid catalysis, the carbon deposition is a very complex polycyclic compound, the determination of the chemical composition and the structure is difficult, and the factors influencing the carbon deposition mainly comprise the pore structure of the catalyst, the distribution of acid sites and the operating conditions. For the microporous or mesoporous ZSM-5 molecular sieve catalyst, the main reason for the reduction of the activity is that the acid sites on the outer surface of the catalyst are active sites of coking reaction, and the generated macromolecular coke causes the blockage of catalyst pore channels, so that the activity of the catalyst is rapidly reduced. Therefore, the development of a novel catalyst is a key factor for improving the quality of the bio-oil and the yield and selectivity of chemicals, and the improvement of the catalytic performance of the catalyst has important significance for the biomass catalytic pyrolysis technology.
MXene is a very attractive two-dimensional material due to its unusual structure and properties. They have the formula M n+1 X n T x (N = 1-3), wherein M is a transition metal (e.g., ti, V, nb, mo, etc.), X is a C or N element, and T represents a chemical group, such as-OH, -O, -Cl, and-F. Having broad chemical and structural change properties making them attractive, e.g. for attachment to the fermi levelHigh conductivity associated with near high electron density of states, excellent hydrophilicity, good mechanical stability and abundant surface chemistry achieved by grafting chemical groups. The advantages enable MXene to have wide application prospects in the fields such as energy storage, catalysis, transparent electronic devices, separation membranes, sensors, composite material reinforcement, electromagnetic shielding, biomedicine and the like.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a preparation method of an MXene-based catalyst for preparing furfural with high selectivity.
The method mainly comprises the following steps:
dispersing multilayer titanium carbide MXene in water to obtain a dispersion liquid A; the solid-to-liquid ratio of the multilayer titanium carbide MXene to water is 1: 100-300, unit is g/ml;
step (2), adding chloroiridic acid and 1-butyl-3-methylimidazole tetrafluoroborate into the dispersion liquid A in sequence, and performing ultrasonic dispersion to obtain a dispersion liquid B; wherein the solid-to-liquid ratio of the chloroiridic acid to the dispersion liquid A is 0.3-1: 100, unit is g/ml; the volume ratio of the 1-butyl-3-methylimidazole tetrafluoroborate to the dispersion liquid A is 1-10: 100, respectively;
and (3) adjusting the pH value of the dispersion liquid B to 10-12 by using sodium hydroxide, reacting for 1-5 h, filtering, washing and drying to obtain a product with the surface alkaline constant Kb and the acid constant Ka being 1.0-2.0: MXene-based catalyst with 1,30-250 nm pore diameter structure.
The method synthesizes the MXene-based catalyst for preparing furfural with high selectivity by using chloroiridic acid as an active metal raw material and layered MXene as a catalyst framework. The ratio of the surface basic constant Kb to the acid constant Ka of the prepared catalyst is 1.0-2.0: 1, the catalyst has proper acidity and alkalinity, and simultaneously has a porous channel structure with the aperture of 30-250 nm, so that the mass transfer resistance is small in the catalytic reaction process, and oxygen-containing biomass macromolecules can quickly enter a catalyst pore channel to be directionally cut, so that the catalyst has good selectivity for furfural, and the defects of complex preparation process, low catalytic performance, easy coking and inactivation and the like of the traditional zeolite molecular sieve are overcome.
Detailed Description
The present invention is further illustrated by the following examples, but the content of the present invention is not limited to the contents of the examples.
Example 1:
(1) 1g of multi-layered titanium carbide MXene was dispersed in 100mL of water to obtain a dispersion A.
(2) To 100ml of dispersion A were added 0.3g of chloroiridic acid and 1ml of 1-butyl-3-methylimidazolium tetrafluoroborate, followed by ultrasonic dispersion to obtain dispersion B.
(3) Adjusting the pH value of the dispersion liquid B to 10 by using sodium hydroxide, reacting for 1h, filtering, washing and drying to obtain a solution with the surface alkaline constant Kb and the acid constant Ka being 1.0: MXene-based catalyst with 1,30-100 nm pore diameter structure.
(4) The rice hull is used as a raw material, the catalyst is adopted to carry out pyrolysis reaction for 4 hours at 400 ℃, and a liquid product is collected. The yield of the liquid product is 41.2 percent, and the content of the 5-hydroxymethylfurfural is 40.5 percent.
Example 2:
(1) 1g of multi-layered titanium carbide MXene was dispersed in 300mL of water to obtain dispersion A.
(2) Adding 1g of chloroiridic acid and 10ml of 1-butyl-3-methylimidazolium tetrafluoroborate into 100ml of the dispersion liquid A, and performing ultrasonic dispersion to obtain a dispersion liquid B;
(3) Adjusting the pH value of the dispersion liquid B to be 12 by using sodium hydroxide, reacting for 5 hours, filtering, washing and drying to obtain a solution with the surface alkaline constant Kb and the acid constant Ka being 2.0: MXene-based catalyst with 1,50-150 nm pore diameter structure;
(4) The wood dust is used as a raw material, the catalyst is adopted to carry out pyrolysis reaction for 6 hours at 500 ℃, and a liquid product is collected. The yield of the liquid product is 43.1 percent, and the content of the 5-hydroxymethylfurfural is 44.5 percent.
Example 3:
(1) 1g of multi-layered titanium carbide MXene was dispersed in 200mL of water to obtain a dispersion A.
(2) To 100ml of dispersion A were added 0.5g of chloroiridic acid, and 3ml of 1-butyl-3-methylimidazolium tetrafluoroborate, followed by ultrasonic dispersion to obtain dispersion B.
(3) Adjusting the pH value of the dispersion liquid B to 10 by using sodium hydroxide, reacting for 2 hours, filtering, washing and drying to obtain a solution with the surface alkaline constant Kb and the acid constant Ka being 1.3: MXene-based catalyst with 1,80-200 nm pore diameter structure;
(4) The wheat straw is used as a raw material, the catalyst is adopted to carry out pyrolysis reaction for 8 hours at 450 ℃, and a liquid product is collected. The yield of the liquid product is 46.5 percent, and the content of the 5-hydroxymethyl furfural is 41.7 percent.
Example 4:
(1) 1g of multi-layered titanium carbide MXene was dispersed in 250ml of water to obtain a dispersion A.
(2) 0.6g of chloroiridic acid and 7ml of 1-butyl-3-methylimidazolium tetrafluoroborate were added to 100ml of the dispersion A, and ultrasonic dispersion was carried out to obtain a dispersion B.
(3) Adjusting the pH value of the dispersion liquid B to 11.5 by using sodium hydroxide, reacting for 4 hours, filtering, washing and drying to obtain a solution with the surface alkaline constant Kb and the acid constant Ka being 1.8: MXene-based catalyst with 1,30-110 nm pore diameter structure;
(4) Animal wastes and sludge are used as raw materials, the catalyst is adopted to carry out pyrolysis reaction for 6 hours at 480 ℃, and liquid products are collected. The yield of the liquid product is 42.5 percent, and the content of the 5-hydroxymethylfurfural is 41.3 percent.
Example 5:
(1) 1g of multi-layered titanium carbide MXene was dispersed in 250ml of water to obtain a dispersion A.
(2) To 100ml of the dispersion A were added 0.9g of chloroiridic acid and 8ml of 1-butyl-3-methylimidazolium tetrafluoroborate, followed by ultrasonic dispersion to obtain a dispersion B.
(3) Adjusting the pH value of the dispersion liquid B to 10.5 by using sodium hydroxide, reacting for 4.5h, then filtering, washing and drying to obtain a solution with the surface alkaline constant Kb and the acid constant Ka being 1.0: MXene-based catalyst with pore diameter structure of 1,40-130 nm.
(4) The method takes vinasse and mushroom dregs as raw materials, adopts the catalyst of the invention to carry out pyrolysis reaction for 6.5 hours at 650 ℃, and collects liquid products. The yield of the liquid product is 41.3 percent, and the content of the 5-hydroxymethylfurfural is 40.2 percent.
The above embodiments are not intended to limit the present invention, and the present invention is not limited to the above embodiments, and all embodiments are within the scope of the present invention as long as the requirements of the present invention are met.
Claims (1)
1. The application of the MXene-based catalyst in preparing furfural with high selectivity is characterized in that the ratio of the surface basic constant Kb to the acid constant Ka of the MXene-based catalyst is (1.0-2.0): 1,30-250 nm pore diameter structure; the MXene-based catalyst is characterized by being prepared by the following steps:
dispersing multilayer titanium carbide MXene in water to obtain a dispersion liquid A; the solid-to-liquid ratio of the multilayer titanium carbide MXene to water is 1: 100-300 (g/ml);
step (2), adding chloroiridic acid and 1-butyl-3-methylimidazole tetrafluoroborate into the dispersion liquid A in sequence, and performing ultrasonic dispersion to obtain a dispersion liquid B; the solid-liquid ratio of the chloroiridic acid to the dispersion liquid A is 0.3-1: 100 (g/ml); the volume ratio of the 1-butyl-3-methylimidazole tetrafluoroborate to the dispersion liquid A is 1-10: 100;
and (3) adjusting the pH value of the dispersion liquid B to 10-12, reacting for 1-5 h, and then filtering, washing and drying to obtain the MXene-based catalyst.
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| AU2012362300A1 (en) * | 2011-12-28 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Process for the production of furfural |
| CN102766119B (en) * | 2012-08-14 | 2014-04-09 | 中国科学技术大学 | Method for preparing 5-methylfurfural |
| CN108793166B (en) * | 2018-07-10 | 2020-06-19 | 中国科学院宁波材料技术与工程研究所 | Composite material of subgroup metal composite MXenes, preparation method and application thereof |
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