CN112717939B - Emulsion Ni/ZrO for catalytic hydrogenation upgrading of caprylic acid 2 Process for preparing catalyst - Google Patents
Emulsion Ni/ZrO for catalytic hydrogenation upgrading of caprylic acid 2 Process for preparing catalyst Download PDFInfo
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- 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
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
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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
- C10G3/45—Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
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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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/02—Gasoline
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
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Abstract
The invention discloses a preparation method of an emulsion Ni/ZrO2 catalyst for catalytic hydrogenation upgrading of caprylic acid, which relates to the technical field of catalysts and comprises the following steps: (1) Dissolving zirconium propanol in propanol, dripping deionized water into the solution to generate a white precipitate, filtering the white precipitate until the white precipitate is not increased any more, and drying the white precipitate; (2) Impregnation of Ni (NO) 3 ) 2 Loading on white precipitate, calcining, and reducing to obtain Ni/ZrO 2 Powder; (3) Ni/ZrO2 under vacuum environment 2 Drying to completely remove water, and cooling to room temperature in a dryer; (4) Mixing Ni/ZrO 2 Adding into dichloromethane, and adding C 17 H 38 Si, slowly stirring the solution uniformly, and then adding B (C) 6 F 5 ) 3 Significant bubbles are generated; (5) After the reaction is carried out until no bubbles exist, washing the sample by using dichloromethane and hexane, washing away residual and physically adsorbed hydrosilane, and then drying the sample in a vacuum environment again to obtain the modified emulsion catalyst Ni/ZrO 2 。
Description
Technical Field
The invention relates to the technical field of catalysts for catalytic hydrogenation and upgrading of biomass, in particular to a catalyst for catalytic hydrogenation and upgrading of biomassRelates to emulsion Ni/ZrO used for catalytic hydrogenation upgrading of octanoic acid 2 A method for preparing the catalyst.
Background
The excessive consumption of fossil fuels raises concerns about environmental issues and national energy safety, and thus, the demand for environmentally friendly and renewable alternative fuels is increasing. At present, biomass plays an increasingly important role in the chemical industry as an alternative renewable carbon source, and is one of promising renewable energy sources. However, direct utilization of biomass as a liquid fuel is not feasible because biomass has a high oxygen content, a low combustion heat value, poor chemical stability and strong corrosiveness, which all hinder practical use of the product as a renewable energy source. Therefore, the production of liquid fuel with high combustion heat value by catalytic hydrogenation upgrading of biomass will provide significant environmental, economic and strategic advantages for the future. The main biomass product obtained by co-pyrolysis of the wood chips and the plastics at the early stage is the octanoic acid, and the octanoic acid is subjected to catalytic hydrogenation to prepare fuels with high combustion heat values such as gasoline and the like, so that the method has extremely high economic value.
At present, octanoic acid is subjected to catalytic hydrogenation to prepare fuel with high combustion heat value such as gasoline, and if common Ni/ZrO is adopted 2 The catalyst carries out catalytic hydrogenation on the octanoic acid, and common Ni/ZrO can be seen from figure 1 2 The catalytic hydrogenation activity to the caprylic acid is not high, the conversion rate of the caprylic acid is increased along with the increase of the temperature, and the conversion rate of the caprylic acid reaches the highest at 240 ℃, but the conversion rate is only 53.2%, the yield of heptane is also low, only 23.6% and the yield of octane is only 17.6%.
Disclosure of Invention
The invention aims to provide an emulsion Ni/ZrO for catalytic hydrogenation upgrading of octanoic acid 2 The preparation method of the catalyst aims to solve the technical problems of low reaction conversion rate and low product yield in the prior art.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a preparation method of an emulsion Ni/ZrO2 catalyst for catalytic hydrogenation upgrading of caprylic acid comprises the following steps:
(1) Dissolving zirconium propanol in propanol, dripping deionized water into the solution to generate a white precipitate, filtering the white precipitate until the white precipitate is not increased any more, and drying the white precipitate;
(2) Impregnation of Ni (NO) 3 ) 2 Loading on white precipitate, calcining, and reducing to obtain Ni/ZrO 2 A powder;
(3) Ni/ZrO2 under vacuum environment 2 Drying to completely remove water, and cooling to room temperature in a dryer;
(4) Mixing Ni/ZrO 2 Adding into dichloromethane, and adding C 17 H 38 Si, slowly stirring the solution uniformly, and then adding B (C) 6 F 5 ) 3 Significant bubbles are generated;
(5) After the reaction is carried out until no bubbles exist, washing the sample by using dichloromethane and hexane, washing away residual and physically adsorbed hydrosilane, and then drying the sample in a vacuum environment again to obtain the modified emulsion catalyst Ni/ZrO 2 。
Preferably, in the step (1), the ratio of the added zirconium propanol, the added propanol and the added deionized water is as follows: 1 g: 10 ml: 2ml.
Preferably, in the step (2), ni (NO) is loaded 3 ) 2 The calcination temperature of the white precipitate is about 450 ℃, the calcination time is 3-5 h, and the calcination gas is air.
Preferably, in step (2), the reduction reaction after calcination is carried out at a temperature of about 450 ℃ in the presence of H 2 Under the condition of reducing gas.
Preferably, in the step (3), the dryer is a vacuum oven, and the drying temperature is 200 ℃.
Preferably, in step (4), ni/ZrO 2 Dichloromethane, C 17 H 38 The ratio of the added amount of Si is as follows: 1g to 20-40 ml to 1-1.5 g.
Compared with the prior art, the invention has the following beneficial effects:
1. the emulsion provided by the invention is Ni/ZrO 2 The catalyst can form a layer between water phase and oil phase interfacesA powdered film. Stirring at high speed to make the water phase form small liquid beads to be dispersed in the oil phase, and emulsion Ni/ZrO 2 The catalyst is attached to the aqueous phase beads, encapsulating the droplets, such that the emulsion Ni/ZrO 2 The catalyst can better contact reactants in a water-oil two-phase, so that the catalytic activity is improved;
2. the emulsion provided by the invention is Ni/ZrO 2 The catalyst has high dispersion degree in water and oil phases. Emulsion Ni/ZrO 2 The catalyst has high dispersity in the water-oil phase, better contacts reactants in the water-oil two-phase, and improves the catalytic activity;
3. the emulsion provided by the invention is Ni/ZrO 2 The catalyst has relatively low cost, the used raw material medicament is safe and easy to obtain, the process flow is convenient and fast, the operation is simple, the energy is saved, and the engineering popularization is facilitated.
Drawings
FIG. 1 is a view of conventional Ni/ZrO 2 A catalytic hydrogenation result diagram of the catalyst on the octanoic acid;
FIG. 2 is an emulsion Ni/ZrO 2 A catalytic hydrogenation result diagram of the catalyst on the octanoic acid;
FIG. 3 shows emulsion catalyst Ni/ZrO 2 Distribution pattern at water-oil phase interface.
Detailed Description
In order to make those skilled in the art better understand the technical solution of the present invention, the present invention is further described below with reference to various embodiments and drawings, and the implementation manner of the present invention includes, but is not limited to, the following embodiments.
Example 1
The emulsion provided by the invention is Ni/ZrO 2 The catalyst is prepared by the following steps:
a) 10g of zirconium propoxide was dissolved in 100mL of propanol and 20mL of deionized water was added dropwise to the solution. A white precipitate was obtained by filtration and then dried in an oven at 80 ℃ for 6 hours.
b) Adding a certain amount of Ni (NO) by impregnation 3 ) 2 Loaded on the white precipitate. Then calcining at 450 deg.C for 4H in air, and finally calcining with H at 450 deg.C 2 Reduction for 2h to obtain Ni/ZrO 2 And (3) powder.
c) Drying with a vacuum oven at 200 deg.C with 1g of Ni/ZrO 2 Drying for 12h, completely removing water, and cooling to room temperature in a dryer.
d) Mixing Ni/ZrO 2 30ml of methylene chloride and 5mmol of C were added 17 H 38 And (3) Si. Slowly stirring the solution uniformly, adding B (C) 6 F 5 ) 3 ，B(C 6 F 5 ) 3 After the addition, hydrogen generation was clearly observed.
e) After the reaction is carried out for 20min, washing the sample by using dichloromethane and hexane, washing away residual and physically adsorbed hydrosilane, and then drying the sample in a vacuum oven again to obtain the modified emulsion catalyst Ni/ZrO with the Ni load of 5 wt% 2 The distribution of the catalyst on the water-oil phase interface is shown in figure 3, and the emulsion catalyst Ni/ZrO 2 Between the water-oil phase interfaces.
Using emulsion Ni/ZrO 2 Catalyst and conventional Ni/ZrO 2 The catalyst is used for catalytic hydrogenation of octanoic acid, and the hydrogenation experimental process is as follows:
the octanoic acid catalytic hydrogenation test was conducted in two 100mL batch autoclaves. 0.1g of an emulsion Ni/ZrO2 catalyst and 3g of octanoic acid were ultrasonically dispersed in a mixed solvent of 7.5mL of deionized water and 42.5mL of n-decane, and 0.1g of a conventional Ni/ZrO2 catalyst and 3g of octanoic acid were ultrasonically dispersed in a mixed solvent of 7.5mL of deionized water and 42.5mL of n-decane, and then the two solutions were transferred to two 100mL stainless steel autoclave reactors, respectively. Reactor H 2 Purging three times to remove impurity gas, and then using H 2 The pressure was increased to 2MPa and the stirring rate was constant (200 rpm). The reactor was then heated to the desired reaction temperature and maintained for 2h. After the reaction was completed, after the autoclave was cooled to room temperature, a liquid sample was taken out, and the conversion of phenol and the yield of the reaction product were analyzed using a gas chromatograph of agilent GC 6820. Gas chromatography uses a (GsBP Inowax 30m by 0.32 mm by 0.25 m) capillary column to separate the different component compounds, and finally the components are analyzed with a Flame Ionization Detector (FID).
Ordinary Ni/ZrO 2 The catalytic hydrogenation result of the catalyst on the octanoic acid is shown in figure 1, emulsion Ni/ZrO 2 CatalysisThe catalytic hydrogenation result of the agent on octanoic acid is shown in figure 2, and common Ni/ZrO can be seen from figure 1 2 The catalytic hydrogenation activity for octanoic acid is not high. The conversion of octanoic acid increased with increasing temperature, and at 240 ℃, the conversion of octanoic acid reached the highest, with a conversion of only 53.2%, the yield of heptane was also lower, only 23.6%, and the yield of octane was only 17.6%. As can be seen from FIG. 2, the emulsion catalyst Ni/ZrO 2 The activity of catalytic hydrogenation of the octanoic acid is improved. The conversion rate of the octanoic acid can reach 73.3 percent at 240 ℃, compared with the common Ni/ZrO 2 The octanoic acid conversion rate is improved by 20.1 percent. The yield of heptane was also improved to 50.9%. In aqueous-oil phase reaction systems, ordinary Ni/ZrO 2 Easily agglomerate in the aqueous phase, making it difficult for the oil phase reactants to reach the catalyst activity. And emulsion catalyst Ni/ZrO 2 The catalyst is dispersed on a water-oil phase interface, and can better contact with reactants to perform catalytic reaction through the dispersion of surface tension, so that the conversion rate is improved.
The above-mentioned embodiment is only one of the preferred embodiments of the present invention, and should not be used to limit the scope of the present invention, but all the insubstantial modifications or changes made within the spirit and scope of the main design of the present invention, which still solve the technical problems consistent with the present invention, should be included in the scope of the present invention.
Claims (6)
1. Emulsion Ni/ZrO for catalytic hydrogenation upgrading of caprylic acid 2 The preparation method of the catalyst is characterized by comprising the following steps:
(1) Dissolving zirconium propanol in propanol, dripping deionized water into the solution to generate a white precipitate, filtering the white precipitate until the white precipitate is not increased any more, and drying the white precipitate;
(2) Impregnation of Ni (NO) 3 ) 2 Loading on white precipitate, calcining, and reducing to obtain Ni/ZrO 2 Powder;
(3) Ni/ZrO2 under vacuum environment 2 Drying to completely remove water, and cooling to room temperature in a dryer;
(4) Ni is combinedZrO 2 Adding into dichloromethane, and adding C 17 H 38 Si, slowly stirring the solution uniformly, and then adding B (C) 6 F 5 ) 3 Significant bubbles are generated;
(5) After the reaction is carried out until no bubbles exist, washing the sample by using dichloromethane and hexane, washing away residual and physically adsorbed hydrosilane, and then drying the sample in a vacuum environment again to obtain the modified emulsion catalyst Ni/ZrO 2 。
2. The method according to claim 1, wherein in the step (1), the ratio of the amounts of zirconium propanol, propanol and deionized water added is: 1 g: 10 mL: 2mL.
3. The production method according to claim 1 or 2, wherein in the step (2), ni (NO) is supported 3 ) 2 The calcination temperature of the white precipitate is 450 ℃, the calcination time is 3-5 h, and the calcination gas is air.
4. The method according to claim 3, wherein in the step (2), the reduction reaction after calcination is carried out at a temperature of 450 ℃ in the form of H 2 Under the condition of reducing gas.
5. The method according to claim 1 or 2, wherein in the step (3), the dryer is a vacuum oven, and the drying temperature is 200 ℃.
6. The production method according to claim 1 or 2, wherein in the step (4), ni/ZrO 2 Dichloromethane, C 17 H 38 The ratio of the added Si is as follows: 1g to 20-40 mL to 1-1.5 g.
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| CN113477254A (en) * | 2021-06-10 | 2021-10-08 | 中国船舶重工集团公司第七一九研究所 | Three-dimensional ordered macroporous structure Ni/ZrO for catalytic hydrogenation upgrading of caprylic acid2Catalyst and preparation method thereof |
| CN113351213B (en) * | 2021-06-10 | 2023-06-02 | 中国船舶重工集团公司第七一九研究所 | Hollow sphere shell-shaped Ni/ZrO for octanoic acid catalytic hydrogenation upgrading 2 Catalyst and preparation method thereof |
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