CN111760597A - Synthesis C9Catalyst for kerosene-like fuel oil and preparation method and application thereof - Google Patents
Synthesis C9Catalyst for kerosene-like fuel oil and preparation method and application thereof Download PDFInfo
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- CN111760597A CN111760597A CN201910262641.7A CN201910262641A CN111760597A CN 111760597 A CN111760597 A CN 111760597A CN 201910262641 A CN201910262641 A CN 201910262641A CN 111760597 A CN111760597 A CN 111760597A
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
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- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
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- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
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- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/48—Silver or gold
- B01J23/50—Silver
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
- B01J37/082—Decomposition and pyrolysis
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- 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
- C07D307/36—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
- C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
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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
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
Abstract
The invention provides a preparation method and application of a noble metal supported catalyst. And placing the sample A in a muffle furnace for roasting to prepare the supported catalyst. The invention adoptsThe C is prepared by one-pot continuous reaction of oxidizing furfural and ethanol into aldol condensation to 2, 2-dimethylfuran by one-step method and carrying out catalytic hydrogenation by using a noble metal supported catalyst9The kerosene-like fuel oil product has good catalytic activity, stability and selectivity and a novel synthesis path, so that the kerosene-like fuel oil product is emphasized.
Description
Technical Field
The invention belongs to the technical field of synthesis of liquid fuel (kerosene fuel oil), and particularly relates to a method for preparing furfural by catalyzing furfural and ethanol to oxidize aldolObtaining 2, 2-difuranmethyl and preparing C by one-pot continuous reaction9Application method of kerosene-like fuel oil product.
Background
The main ways of converting biomass into liquid fuel include thermochemical gasification to produce synthesis gas, biomass liquefaction or pyrolysis to produce bio-oil, conversion of sugar to ethanol and esterification of triglycerides to produce biodiesel. However, the development of new technologies is crucial to accelerate the development of renewable fuels from biomass. In this regard, the most efficient and effective utilization of renewable biomass resources is through the development of an integrated biorefinery in which the energy requirements of each process are balanced with the energy requirements of other processes similar to petroleum refining. To this end, the conversion of polysaccharides in lignocellulosic biomass to furfural using biological, thermal and chemical processes has been classified as one of the top 30 biomass-derived platform compounds by the U.S. department of energy.
Furfural can be converted to C by aldehyde condensation7And C8Molecules, which are an important basis for the production of liquid hydrocarbon fuels and fuel additives and the synthesis of valuable chemicals. For example, previous studies have shown that aldehyde condensation of furfural and acetone over basic catalysts (e.g., sodium hydroxide solution) forms oxidized C8A chemical. And the aldehyde condensation reaction is applied to the oxidation of furfural and 'cellulose' ethanol to prepare oxygenated C7A chemical. The condensation of furfural with ethanol by aldehyde oxidation mainly comprises two steps: (1) the selective oxidation of ethanol to acetaldehyde is typically catalyzed on metal particles: (2) reacting furfural with acetaldehyde to produce final C7Product, C7The product appears at the basic site. However, the direct synthesis of long-chain molecules with C being more than or equal to 9 by furfural and ethanol is rarely reported, and provides an important breakthrough for the diversification and sustainable development of biofuel production. Furfural can be converted to C by aldehyde condensation7And C8Molecules, which are an important basis for the production of liquid hydrocarbon fuels and fuel additives and the synthesis of valuable chemicals. For example, previous studies have shown that aldehyde condensation of furfural and acetone over basic catalysts (e.g., sodium hydroxide solution) forms oxidized C8A chemical. And the aldehyde condensation reaction is applied toOxidation of furfural with "cellulosic" ethanol to produce oxygenated C7A chemical. The condensation of furfural with ethanol by aldehyde oxidation mainly comprises two steps: (1) the selective oxidation of ethanol to acetaldehyde, typically catalyzed on metal particles; (2) reacting furfural with acetaldehyde to produce final C7Product, C7The product appears at the basic site. However, the direct synthesis of long-chain molecules with C being more than or equal to 9 by furfural and ethanol is rarely reported, and provides an important breakthrough for the diversification and sustainable development of biofuel production.
Disclosure of Invention
The invention adopts noble metal supported catalyst, and prepares C by one-pot continuous reaction of furfural and ethanol oxidized aldol condensation to 2, 2-dimethylfuran through one-step method, catalytic hydrogenation and the like9The kerosene-like fuel oil product has good catalytic activity, stability and selectivity and a novel synthesis path, so that the kerosene-like fuel oil product is emphasized.
In one aspect, the present invention provides a method for preparing a supported catalyst, the method comprising the steps of:
(1) stirring and dissolving the protective agent in hot water at the temperature of 60-90 ℃, cooling to room temperature, sequentially adding a metal precursor and a metal oxide carrier, and stirring for 120-360 min to obtain a solution A; the mass ratio of the metal precursor to the metal oxide carrier to the protective agent is 1 (30-50) to (40-50); (2) dissolving a reducing agent sodium borohydride in ice water to obtain a solution B; the mass ratio of the reducing agent to the precursor is 1 (1-3);
(3) adding the solution B into the solution A, stirring for 120-360 min, washing with deionized water, and drying in an oven at 50-150 ℃ for 4-24h to obtain solid powder A;
(4) and (3) roasting the solid powder A in a muffle furnace at 300-600 ℃ for 2-4 h, and naturally cooling after roasting to obtain the supported catalyst.
Based on the technical scheme, preferably, the metal precursor is a noble metal precursor, and the noble metal precursor is one of chloride, nitrate, acetate and carbonate of noble metal; the noble metal is platinum, palladium or gold.
Based on the technical scheme, preferably, theThe metal oxide carrier is Al2O3、TiO2、NiO、Fe3O4、SiO2、Co3O4、CeO2、ZnO、Fe2O3、La2O3、MnO2At least one of (1).
Based on the above technical scheme, preferably, the protective agent is PVA (Polyvinyl alcohol), PVP (Polyvinyl pyrrolidone), Silica sol (Silica sol), P123 (polyethylene oxide-polypropylene oxide-polyethylene oxide), or Poloxamer (polyoxyethylene polyoxypropylene ether block copolymer, Poloxamer).
Based on the technical scheme, the roasting temperature is preferably 300 ℃, 400 ℃ and 500 ℃.
Based on the technical scheme, preferably, the initial temperature of the roasting is 10-40 ℃, and the heating rate is 5-10 ℃/min.
In another aspect of the present invention, the supported catalyst prepared by the above method is provided, wherein the supported amount of the metal on the metal oxide carrier is 0.1 to 2 wt%.
The invention also provides a method for preparing 2, 2-difuranmethyl by the supported catalyst in the oxidation reaction of furfural by a series method and preparing C by hydrogenation9Use of a kerosene-like product.
Based on the technical scheme, the following steps are preferred: adding the catalyst, furfural and ethanol solvent into an air-filled reaction kettle, reacting for 3-6h at 80-150 ℃, and then carrying out one-step hydrogenation to prepare kerosene fuel oil to complete the whole series reaction; the mass ratio of the catalyst, the furfural and the ethanol solvent is 1 (2-5) to (0.2-0.5).
The method comprises the steps of stirring a noble metal salt precursor aqueous solution, adding a protective agent PVP, reducing by sodium borohydride, adding a carrier oxide, washing and drying to obtain a sample A. And placing the sample A in a muffle furnace to be roasted to prepare a supported catalyst B. The supported catalyst A is roasted in a muffle furnace to remove the protective agent PVP, so that the metal is better exposed on the surface of the carrier. And placing the obtained supported catalyst in an air-filled reaction kettle, adding a furfural and ethanol solvent, reacting at the temperature of 80-150 ℃ for 3-6 hours, further hydrogenating to prepare kerosene fuel oil, and detecting by GC/MS.
Compared with the prior art, the invention has the following advantages: the preparation method of the supported catalyst is simple, avoids loss of the noble metal precursor, is suitable for large-scale synthesis, and can be amplified to kilogram-level production; has wide development space and market application value; reducing agents, stabilizing agents and surface active agents which are not friendly to the environment are not used in the preparation process; the main product of furfural oxidation is C9The kerosene-like fuel oil product can provide important breakthrough for the diversification and sustainable development of hydrocarbon biofuel production.
High efficiency of catalyst, including conversion rate of furfural and C9The selectivity of the kerosene-like fuel oil product is high; the catalyst has very good reusability.
Drawings
Figure 1 is the XRD pattern of the catalyst prepared in example 1.
FIG. 2 is a scanning transmission electron microscope photograph of the catalyst prepared in example 5 with the AC-STEM spherical aberration correction.
FIG. 3 is a graph showing the catalytic oxidation activity test of example 8.
FIG. 4 is a schematic diagram of a hydrogenated kerosene fuel oil according to example 9.
Detailed Description
Example 1
1) 1g of PVA was dissolved in 400mL of water (80 ℃ C.), and 21mg of HAuCl was added thereto after cooling to room temperature4·4H2Stirring O at the rotation speed of 600rpm for 1 hour for dissolution, dissolving 9.6mg of sodium borohydride in ice water, quickly adding the sodium borohydride into a beaker, stirring for 4 hours, adding 1g of NiO carrier, stirring for 3 hours, centrifugally washing, putting the mixture into a vacuum drying oven, and drying at 50 ℃ for 12 hours to obtain solid powder A.
2) The powder A was calcined in a muffle furnace at 300 ℃ for 3h at 10 ℃/min to prepare a 1 wt.% Au/NiO catalyst.
Example 2
1) 1g of PVA was dissolved in 400mL of water (80 ℃ C.), and 21mg of HAuCl was added thereto after cooling to room temperature4·4H2Stirring O at the rotation speed of 600rpm for 1h for dissolution, dissolving 9.6mg of sodium borohydride in ice water, quickly adding into a beaker, stirring for 4h, and adding 1g of TiO2Stirring the carrier for 3h, centrifugally washing, putting into a vacuum drying oven, and drying at 50 ℃ for 12h to obtain solid powder B.
2) Roasting the powder B in a muffle furnace at 300 ℃ for 3h at the temperature of 10 ℃/min to prepare 1 wt% of Au/TiO2A catalyst.
As shown in fig. 1, which is the XRD pattern of the catalyst of example 1, it can be seen that three sharp and intense diffraction peaks appear at 37.5 °,43.6 ° and 63.2 ° respectively, and can be assigned to the (111), (200) and (220) crystal plane compositions (PDF 47-1049) of the pure NiO species. Due to the good dispersion of the gold nanoparticles on the NiO surface, no diffraction peak associated with the gold nanoparticles was found.
Example 3
Preparation of X/NiO (X ═ Pd)
The catalyst was prepared by the method of example 1 except that the metal precursor salt was changed to potassium tetrachloropalladate and the other steps were carried out in accordance with example 1 to prepare a 0.65 wt% Pd/NiO catalyst.
Example 4
Preparation of X/NiO (X ═ Pt)
A catalyst was prepared by the method of example 1 except that the metal precursor salt was changed to potassium tetrachloroplatinate, and the other steps were performed with reference to example 1 to prepare a 1.0 wt% Pt/NiO catalyst.
Examples 5 to 7
The catalyst was prepared by the method of example 1, and the calcination temperatures of the catalysts were changed to 300 deg.C, 400 deg.C, and 500 deg.C, respectively, to prepare Au/NiO-300 deg.C, Au/NiO-400 deg.C, and Au/NiO-500 deg.C catalysts (metal loading of 1 wt%). FIG. 2 is a scanning transmission electron microscope photograph of the Au/NiO prepared in example 5 with a spherical aberration correction at 300 ℃ from which it can be seen that Au nanoparticles are deposited on the NiO (200) plane with a 0.23nm lattice fringe of Au (111) cross section.
Example 8
FIG. 3 is a graph showing that the supported catalyst Au/NiO-300 ℃ (100mg) is placed in an air-filled (1MPa) reaction kettle, furfural and an ethanol solvent are added, the reaction is carried out at 130 ℃ under the conditions that 30mg of the ethanol solvent is used for 1-6 h and 400mg of furfural is used, and the conversion rate and the selectivity of products are detected and analyzed through GC/MS at different time periods. From the figure, it can be seen that the conversion rate of furfural rapidly increases at the initial stage, reaches the maximum value of 90% at about 2h, and is basically maintained at 92% along with the extension of the reaction time. In terms of product selectivity, 3- (2-Furfuryl) Acrolein (FA) is subjected to aldol condensation, and the selectivity is 61-63% within 1-4 h of reaction time and gradually reduced to 54% with the time. After 6 h. With increasing furfural conversion, the selectivity of the oxidized esterification product, ethyl Ester of Furfural (EF), increased to 27% from the first 1h and then rapidly dropped to 15% within 2 h. During the reaction, the selectivity of 2- (furan-2-methyl) furan (DFM) was from 6% for the first 1 hour to 20% for 2 hours, and then from 22% for 4 hours to 28% for 6 hours.
Example 9
The product obtained in example 8 was subjected to a hydrogen gas atmosphere of 1MPa (the other conditions were the same), and the final product of the reaction was analyzed by GC/MS detection. From FIG. 4, it can be seen that furfural reacted to form C7And C9The hydrocarbon reaction route is that in the presence of oxygen and potassium carbonate, the Au/NiO catalyst is used in the oxidative esterification reaction and the aldol condensation reaction of ethanol, and then the hydrogenation reaction is carried out on the reaction product and hydrogen.
Claims (9)
1. A method of preparing a supported catalyst, comprising the steps of:
(1) stirring and dissolving the protective agent in water at the temperature of 60-90 ℃, cooling to room temperature, sequentially adding a metal precursor and a metal oxide carrier, and stirring for 120-360 minutes to obtain a solution A: the mass ratio of the metal precursor to the metal oxide carrier to the protective agent is 1 (30-50) to (40-50);
(2) dissolving a reducing agent sodium borohydride in ice water to obtain a solution B; the mass ratio of the reducing agent sodium borohydride to the metal precursor is 1 (1-3);
(3) adding the solution B into the solution A, stirring for 120-360 minutes, washing with deionized water, and drying in an oven at 50-150 ℃ for 4-24 hours to obtain solid powder A;
(4) and (3) roasting the solid powder A in a muffle furnace at 300-600 ℃ for 2-4 hours, and naturally cooling after roasting to obtain the supported catalyst.
2. The method of claim 1, wherein the metal precursor is a noble metal precursor, and the noble metal precursor is one of a chloride, nitrate, acetate, and carbonate of a noble metal; the noble metal is platinum, palladium or gold.
3. The method of claim 1, wherein the metal oxide support is Al2O3、TiO2、NiO、Fe3O4、SiO2、Co3O4、CeO2、ZnO、Fe2O3、La2O3、MnO2At least one of (1).
4. The method of claim 1, wherein the protective agent is PVA (Polyvinyl alcohol), PVP (polyvinylpyrrolidone), Silica sol (Silica sol), P123 (polyethylene oxide-polypropylene oxide-polyethylene oxide), or Poloxamer (polyoxyethylene polyoxypropylene ether block copolymer, Poloxamer).
5. The method of claim 1, wherein the firing temperature is 300 ℃, 400 ℃, 500 ℃.
6. The method according to claim 1, wherein the initial temperature of the calcination is 10 to 40 ℃ and the temperature rise rate is 5 to 10 ℃/min.
7. A supported catalyst prepared by the method of any one of claims 1 to 6, wherein the amount of the supported metal oxide is 0.1 to 2 wt%.
8. The application of the supported catalyst of claim 7, which is characterized in that the catalyst is used for catalyzing the oxidation reaction of furfural to prepare 2, 2-difuranmethyl and hydrogenating to prepare C9Kerosene-like oil.
9. Use according to claim 8, characterized in that: adding the catalyst, furfural and ethanol solvent into an air-filled reaction kettle, reacting for 3-6h at 80-150 ℃, and further hydrogenating to prepare C9Kerosene-like fuel oil; the mass ratio of the catalyst, the furfural and the ethanol solvent is 1 (2-5) to (0.2-0.5).
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110479304A (en) * | 2019-07-27 | 2019-11-22 | 内蒙古农业大学 | A kind of gold prepares the application of hydro carbons liquid biological fuel with the preparation method and its catalysis biological ethyl alcohol of oxide carrier composite catalyst |
| CN115869951A (en) * | 2022-12-13 | 2023-03-31 | 鲁东大学 | Non-noble metal modified titanium dioxide catalyst and preparation method and application thereof |
Citations (1)
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| CN101822982A (en) * | 2008-03-19 | 2010-09-08 | 长春工业大学 | Catalyst for furan production by furfural liquid-phase decarbonylation, preparation method and application method thereof |
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2019
- 2019-04-02 CN CN201910262641.7A patent/CN111760597A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101822982A (en) * | 2008-03-19 | 2010-09-08 | 长春工业大学 | Catalyst for furan production by furfural liquid-phase decarbonylation, preparation method and application method thereof |
Non-Patent Citations (1)
| Title |
|---|
| FANG, QJHUA，ET AL: "Au/NiO Composite: A Catalyst for One-Pot Cascade Conversion of Furfural", 《ACS APPLIED ENERGY MATERIALS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110479304A (en) * | 2019-07-27 | 2019-11-22 | 内蒙古农业大学 | A kind of gold prepares the application of hydro carbons liquid biological fuel with the preparation method and its catalysis biological ethyl alcohol of oxide carrier composite catalyst |
| CN115869951A (en) * | 2022-12-13 | 2023-03-31 | 鲁东大学 | Non-noble metal modified titanium dioxide catalyst and preparation method and application thereof |
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