CN115739097A - Efficient catalyst for preparing alkane by hydrodeoxygenation of palmitic acid and preparation method and application thereof - Google Patents
Efficient catalyst for preparing alkane by hydrodeoxygenation of palmitic acid and preparation method and application thereof Download PDFInfo
- Publication number
- CN115739097A CN115739097A CN202211602972.9A CN202211602972A CN115739097A CN 115739097 A CN115739097 A CN 115739097A CN 202211602972 A CN202211602972 A CN 202211602972A CN 115739097 A CN115739097 A CN 115739097A
- Authority
- CN
- China
- Prior art keywords
- catalyst
- palmitic acid
- powder
- atmosphere
- hydrodeoxygenation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- 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
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a high-efficiency catalyst for preparing alkane by hydrodeoxygenation of palmitic acid and a preparation method and application thereof 3 C 2 The material is taken as a carrier, and the Ti is prepared by room temperature impregnation-roasting coupling 3 C 2 The material loaded metal nickel particle catalyst has hydrodeoxygenation activity, can be used for preparing alkane by catalytic hydrodeoxygenation of palmitic acid, and has high yield of the obtained alkane.
Description
Technical Field
The invention relates to the technical field of biomass energy utilization, in particular to a high-efficiency catalyst for preparing alkane by hydrodeoxygenation of palmitic acid, and a preparation method and application thereof.
Background
Renewable biomass energy is a typical environment-friendly resource, is naturally sourced, has abundant reserves, is inexhaustible, and can absorb and convert carbon dioxide in air through photosynthesis to realize closed loop of cyclic utilization of the carbon dioxide. Among various biomasses, microalgae biomass in the ocean is considered to be a very promising biomass energy source, on one hand, the microalgae biomass can be converted into energy to prepare valuable oil products or chemicals, and on the other hand, the microalgae biomass can be converted into energy to treat the pollution of algae in the ocean. Nevertheless, there are significant challenges to energy-utilizing algae. Microalgae oil prepared after the thermochemical conversion of microalgae contains a large amount of oxygen-containing compounds, so that the quality of bio-oil products is poor and the calorific value is low. Fatty acids and fatty acid esters are the main constituents in microalgal oils. Lipid compounds can be further converted to higher alkane mixtures by Hydrodeoxygenation (HDO) techniques [ ACSCatalysis,2016, 4512-4525].
In recent years, ni-based catalysts have been generally used to catalyze HDO reactions because of their inexpensive price and high deoxygenation activity. Ni-based catalysts can catalyze the decarbonylation of aldehyde and alcohol intermediates, as well as the hydrogenation of-COOH, -CHO and C = C double bonds in reactants or intermediate derivatives [ angelavendte chemie international edition,2012, 51. However, the high C — C bond cleavage activity of the Ni-based catalyst leads to economic loss of carbon atoms of the target product, and Ni particles tend to agglomerate during preparation and reaction of the Ni-based catalyst, which is very disadvantageous to the stability of the catalyst. It is therefore necessary to study the coupling of dispersed Ni particles by the strong interaction of the support with Ni.
Disclosure of Invention
The invention aims to provide a novel two-dimensional Ti aiming at the technical problem that the activity of a hydrogenation reaction Ni-based catalyst is easy to agglomerate and influence 3 C 2 The material is used for loading and dispersing active Ni particles and is applied to the preparation of alkane through the catalytic hydrodeoxygenation reaction of palmitic acid.
In order to realize the purpose, the technical scheme adopted by the invention is as follows:
a preparation method of a high-efficiency catalyst for preparing alkane by hydrodeoxygenation of palmitic acid is characterized by comprising the following preparation steps:
Wherein, the Ti added in the step 1 3 AlC 2 The mass ratio of the powder to the hydrofluoric acid is 1. Preferably, ti is added in step 1 3 AlC 2 The mass ratio of powder to hydrofluoric acid was 2:9.
Wherein the pH value of the supernatant fluid after water washing in the step 2 is 5-7. Preferably, the pH of the washed supernatant is about 6.
Wherein, in step 3, black Ti 3 C 2 The mass ratio of the powder to the deionized water is 1. Preferably, black Ti in step 3 3 C 2 The mass ratio of powder to deionized water was 1:6. The mass ratio of the nickel nitrate hexahydrate solid to the deionized water in the step 3 is 1-1:3. Preferably, the mass ratio of nickel nitrate hexahydrate solid to deionized water is 1:5.
Wherein, the ultrasonic time at room temperature in the step 3 is 15-30 minutes, and the standing time is 8-24 hours. Preferably, the ultrasonic time is 20 minutes at room temperature and the standing time is 12 hours.
Wherein, the vacuum drying in the step 4 refers to vacuum drying for 24 hours at the temperature of 75-85 ℃. Preferably, vacuum drying in step 4 means vacuum drying at 80 ℃ for 24 hours.
Wherein, the step 5 of roasting in Ar atmosphere refers to roasting in Ar atmosphere for 2-5 hours at the temperature of 300-400 ℃, and the heating rate is 5-20 ℃/min; h 2 The reduction under the mixed Ar atmosphere refers to that H with the volume ratio of 3-8% is carried out at the temperature of 320-380 DEG C 2 Reducing for 3-6 hours in the mixed atmosphere of/Ar, wherein the heating rate is 5-20 ℃/min.
Preferably, the roasting in Ar atmosphere in the step 5 means roasting in Ar atmosphere at 350 ℃ for 3 hours at a heating rate of 10 ℃/min; h 2 The reduction under the mixed atmosphere of/Ar means that the volume ratio of H at 350 ℃ is 5 percent 2 And reducing for 4 hours in an Ar mixed atmosphere, wherein the heating rate is 10 ℃/min.
The catalyst Ti prepared by the method 3 C 2 The material carries metallic nickel particles (Ni/Ti) 3 C 2 ) The catalyst is used for preparing alkane by hydrogenation and deoxidation of palmitic acid, the load amount of Ni is 10-40 wt%, the particle size of Ni particles is 10-50nm (generally about 30 nm), and the Ni particles are wrapped in Ti 3 C 2 Of the surface of (a).
Preferably, the loading of Ni is 15wt%.
Preferably, the catalyst Ni/Ti 3 C 2 When the catalyst is applied to the hydrodeoxygenation reaction of palmitic acid, the catalyst Ni/Ti is added 3 C 2 Added to a 1.35wt% n-decane solution of palmitic acid, the reaction conditions were set as follows: the temperature is 230-350 ℃ (preferably 300 ℃), the pressure is 0-5MPa (preferably 4 MPa), and the reaction time is 2-5h (preferably 4 h). And after the reaction is finished, taking out the liquid product, and carrying out qualitative and quantitative analysis on the palmitic acid conversion rate and the alkane product by adopting a gas chromatograph and a gas chromatograph.
The invention has the beneficial effects that:
1.Ti 3 C 2 the surface of the material contains a large number of functional groups such as-O, -OH, -F and the like, and abundant surface electronegative functional groups are favorable for coupling with a metal Ni precursor.
2.Ti 3 C 2 The material has a large two-dimensional active surface, and can promote the dispersion of Ni particles through a synergistic coupling effect.
3. The invention prepares Ti by a room temperature dipping-roasting coupling method 3 C 2 The material is used as a carrier to couple the catalyst of active component Ni particles, and the improvement of the catalytic activity of the catalyst is mainly attributed to the Ni particles and Ti 3 C 2 Strong synergy between the two materials. Ti 3 C 2 The material is helpful for adsorption and conversion of carboxylic acid in palmitic acid; the Ni active site promotes decarbonylation and hydro-dehydration path, thereby realizing the efficient hydro-deoxidation of the palmitic acid to prepare the alkane. Ni/Ti 3 C 2 The catalyst shows excellent catalytic activity and stability, and has important significance for preparing alkane by hydrodeoxygenation of palmitic acid.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the embodiments or the description in the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without creative efforts.
FIG. 1 shows Ni/Ti ratios prepared in example 1 3 C 2 SEM image at 3 μm scale of (a);
FIG. 2 shows Ni/Ti prepared in example 1 3 C 2 SEM image at 1 μm scale of (a);
FIG. 3 shows Ni/Ti ratios prepared in example 1 3 C 2 A TEM image of (B);
FIG. 4 shows Ni/Ti prepared in example 1 3 C 2 XRD spectrum of (1);
FIG. 5 shows Ni/Ti prepared in example 1 3 C 2 N of (A) 2 Adsorption and desorption isotherms;
FIG. 6 shows the different reaction temperatures vs. Ni/Ti in example 2 3 C 2 The catalyst is used for preparing alkane through hydrogenation and deoxidation of palmitic acid;
FIG. 7 shows different reaction pressures for Ni/Ti in example 3 3 C 2 The catalyst is used for preparing alkane through hydrogenation and deoxidation of palmitic acid;
FIG. 8 shows the Ni/Ti ratio of the catalyst of example 4 3 C 2 The result of the deoxidation cycle stability of the palmitic acid is shown.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to examples, but it will be understood by those skilled in the art that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The present invention will be further explained with reference to specific embodiments.
Example 1
Catalyst Ni/Ti 3 C 2 The preparation of (1):
weighing 1gTi 3 AlC 2 The powder was placed in a centrifuge tube and 10mL of hydrofluoric acid solution was added. After 24h of reaction at room temperature in a fume hood, separating the reaction product by centrifugal water washing, centrifuging for many times to make the pH value of the supernatant close to 6, collecting the lower precipitate, and freeze-drying the lower precipitate by a freeze dryer to obtain multilayer Ti 3 C 2 A material.
0.5g of Ti was weighed 3 C 2 Material and 0.62gNi (NO) 3 ) 2 ·6H 2 Dispersing O in 3mL of deionized water, performing ultrasonic treatment for 20min, and standing the mixed solution at room temperature for 12h. Due to the synthesized Ti 3 C 2 The surface of the material contains a large number of functional groups (e.g., -OH, -O, and-F) whose presence contributes to the Ni in the Ni source 2+ With Ti 3 C 2 The material is sufficiently adsorbed by electrostatic attraction. After standing for 12h, the mixed solution was dried in a vacuum oven at 80 ℃ for 24h, then the dried powder was ground and calcined in an Ar atmosphere at 350 ℃ for 3h, followed by 5%H at 350 ℃ 2 Roasting in the mixed gas of/Ar for 4h at a heating rate of 10 ℃ for min –1 . Under the action of the vacuum drying and thermal reduction, ti 3 C 2 Ni adsorbed on surface of material 2+ Can be further converted into Ni particles; finally successfully prepares Ni/Ti by the steps 3 C 2 And (3) compounding a catalyst. The characterization results of the catalyst are shown in FIGS. 1 to 5. The results show that Ni/Ti 3 C 2 In the catalyst, black Ni particles are wrapped in Ti 3 C 2 The particle size of the surface of the material is about 30nm, the catalyst has an obvious mesoporous structure, and the pore size distribution is 3-27 nm.
The molecular sieve, the metal oxide and the carbon material are generally selected as the carriers to disperse Ni particles, excellent catalytic property is shown, and the carriers with different chemical surface properties can further improve the stability of the Ni-based catalyst and enrich the application of the Ni-based catalyst. Novel two-dimensional Ti 3 C 2 The material has a large number of functional groups (-OH, -O and-F) on the surface after being prepared, and the existence of the functional groups-OH, -O and-F enables Ti 3 C 2 Has abundant surface chemistry and stronger compatibility, and can form a composite catalyst with better activity by strong interface coupling with other metal ions.
The Ti with the surface rich in a large number of electronegative functional groups is prepared by a fluorine-containing etching method 3 C 2 Material, by means of a carrier Ti 3 C 2 The non-noble metal Ni component with lipid deoxidation activity and Ti are successfully introduced under the action of electrostatic adsorption and chemical coupling between the material and the Ni active component 3 C 2 The large two-dimensional surface of the material can fully promote the dispersion of Ni, so that the problem that Ni particles are easy to agglomerate is solved.
The experimental result shows that the improvement of the deoxidation performance of the palmitic acid is mainly attributed to Ni and Ti 3 C 2 Strong synergy between the two materials. Ti (titanium) 3 C 2 The material is helpful for adsorption and conversion of carboxylic acid in palmitic acid; the Ni active sites promote the C-C bond cleavage of the hexadecanal intermediate product to form pentadecane in a decarbonylation mode, and promote the hexadecanol intermediate product to form hexadecane through a hydro-dehydration path. Catalyst Ni/Ti 3 C 2 The catalyst shows excellent catalytic activity and stability, and has important significance for preparing alkane by hydrodeoxygenation of palmitic acid.
Example 2
Different reaction temperature pairs of Ni/Ti 3 C 2 Catalyst for preparing alkane by hydrodeoxygenation of palmitic acidThe result should be:
ultrasonic dissolving 0.5g palmitic acid in 50mL n-decane solvent, mixing uniformly, pouring the solution into a reaction kettle, and adding 0.1gNi/Ti 3 C 2 A catalyst. The air in the sealed reaction kettle is replaced by 0.2MPa hydrogen for 3 times, and finally the hydrogen is filled to 4MPa. And then, sequentially starting circulating condensed water and stirring, adjusting the rotating speed to 300rpm, setting a certain reaction temperature and reaction time for 4 hours, and then starting the reaction. Collecting supernatant by centrifuging after reaction, qualitatively and quantitatively detecting the filtered and dewatered sample by gas chromatography, setting the temperature of gas chromatography injection port and detector to 325 deg.C, setting the programmed temperature condition of column box to 120 deg.C, maintaining for 2min, and maintaining at 10 deg.C for min −1 The temperature was raised to 260 ℃ and maintained for 10min. The results are shown in FIG. 6, the temperature is 280 ℃, the conversion rate of palmitic acid can reach 95.93%, the total yield of alkane reaches 49.70%, and the results show that Ni/Ti 3 C 2 The catalyst has better palmitic acid hydrodeoxygenation activity.
Example 3
Different reaction pressure pairs of Ni/Ti 3 C 2 The result of the reaction of the catalyst in the preparation of alkane by hydrogenation and deoxidation of palmitic acid is as follows:
ultrasonic dissolving 0.5g palmitic acid in 50mL n-decane solvent, mixing uniformly, pouring the solution into a reaction kettle, and adding 0.1gNi/Ti 3 C 2 A catalyst. The air in the sealed reaction kettle is replaced by 0.2MPa hydrogen for 3 times, and finally the hydrogen is filled to a certain pressure. Then, the circulating condensed water and the stirring are sequentially started, the rotating speed is adjusted to 300rpm, the reaction temperature is set to 300 ℃, and the reaction time is set to 4 hours, and then the reaction is started. Collecting supernatant by centrifugation after reaction, qualitatively and quantitatively detecting the filtered and dewatered sample by gas chromatography, setting the temperature of gas chromatography injection port and detector to 325 deg.C, setting the programmed temperature condition of column box to 120 deg.C, maintaining for 2min, and maintaining at 10 deg.C for min −1 The temperature was raised to 260 ℃ and maintained for 10min. As shown in FIG. 7, the conversion rate of palmitic acid was 100%, the total yield of product alkanes was 78.11%, and the main alkanes were completely converted at 300 deg.C for 4h under 4MPa of hydrogen pressureThe yield of the hydrocarbon product pentadecane was 56.51%, indicating Ni/Ti 3 C 2 The catalyst facilitates decarbonylation such that C-C is cleaved to form pentadecane. The above results show that the Ni/Ti 3 C 2 The catalyst has excellent palmitic acid hydrodeoxygenation activity.
Example 4
Catalyst Ni/Ti 3 C 2 Palmitic acid deoxidation cycle stability results:
ultrasonic dissolving 0.5g palmitic acid in 50mL n-decane solvent, mixing uniformly, pouring the solution into a reaction kettle, and adding 0.1gNi/Ti 3 C 2 A catalyst. The air in the sealed reaction kettle is replaced by 0.2MPa hydrogen for 3 times, and finally the hydrogen is filled to 4MPa. Then, the circulating condensed water and the stirring are sequentially started, the rotating speed is adjusted to 300rpm, the reaction temperature is set to 300 ℃, and the reaction time is set to 4 hours, and then the reaction is started. Collecting supernatant liquid in a centrifugal mode after the reaction is finished, and qualitatively and quantitatively detecting the filtered and dewatered sample through gas chromatography. The separated solid catalyst was used in the next cycle. Setting the temperature of the gas chromatography sample inlet and the detector to 325 ℃, setting the temperature programming condition of the column box to be 120 ℃ at the initial temperature for 2min, and keeping the temperature for 10 ℃ for min −1 The temperature was raised to 260 ℃ and maintained for 10min. The results are shown in fig. 8, the conversion rate of the palmitic acid catalyzed by the catalyst is 100% after 5 times of repeated use, and the target product C 15 +C 16 Has no obvious reduction in selectivity, indicating that Ni/Ti 3 C 2 The catalyst has excellent catalytic deoxidation stability of the palmitic acid.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (13)
1. A preparation method of a high-efficiency catalyst for preparing alkane by hydrodeoxygenation of palmitic acid is characterized by comprising the following preparation steps:
step 1. Mixing Ti 3 AlC 2 Adding the powder into hydrofluoric acid solution, and reacting in a fume hood at room temperature for 24 hours to obtain a mixed solution A;
step 2, centrifugally washing the mixed solution A with deionized water for multiple times, collecting the lower-layer precipitate, and freeze-drying to obtain black Ti 3 C 2 Powder;
step 3, adding black Ti 3 C 2 Mixing the powder and nickel nitrate hexahydrate solid in deionized water, performing ultrasonic dispersion at room temperature, and standing to obtain a mixed solution B;
step 4, carrying out vacuum drying and grinding on the mixed solution B to obtain precursor powder;
step 5, roasting the precursor powder in Ar atmosphere, and then in H 2 Reducing under the mixed atmosphere of/Ar to obtain multilayer Ti 3 C 2 Catalyst of material loaded metallic nickel particles, denoted as catalyst Ni/Ti 3 C 2 。
2. The method according to claim 1, wherein the Ti added in step 1 is 3 AlC 2 The mass ratio of the powder to the hydrofluoric acid is 1.
3. The method according to claim 1, wherein the pH of the washed supernatant in the step 2 is 5 to 7.
4. The method according to claim 1, wherein black Ti in step 3 3 C 2 The mass ratio of the powder to the deionized water is 1.
5. The preparation method according to claim 1, wherein the mass ratio of the nickel nitrate hexahydrate solid to the deionized water in the step 3 is 1.
6. The method according to claim 1, wherein the sonication time at room temperature in step 3 is 15 to 30 minutes.
7. The method according to claim 1, wherein the standing time at room temperature in step 3 is 8 to 24 hours.
8. The method according to claim 1, wherein the vacuum drying in step 4 is performed at 75 to 85 ℃ for 24 hours.
9. The method of claim 1, wherein the firing in Ar atmosphere in step 5 is performed at a temperature of 300-400 ℃ for 2-5 hours in Ar atmosphere at a heating rate of 5-20 ℃/min.
10. The method according to claim 1, wherein H in step 5 2 The reduction under the mixed Ar atmosphere refers to that H with the volume ratio of 3-8% is carried out at the temperature of 320-380 DEG C 2 Reducing for 3-6 hours in the mixed atmosphere of/Ar, wherein the heating rate is 5-20 ℃/min.
11. A high-efficiency catalyst prepared by the preparation method according to any one of claims 1 to 10.
12. The use of the high efficiency catalyst of claim 11, wherein the catalyst is Ni/Ti 3 C 2 The method is used for preparing alkane by hydrodeoxygenation of palmitic acid;
the catalyst Ni/Ti 3 C 2 Wherein the loading amount of Ni is 10-40 wt%, the particle diameter of Ni particles is 10-50nm, and the Ni particles are wrapped in Ti 3 C 2 T x Of the surface of (a).
13. Use according to claim 12, characterised in that the catalyst Ni/Ti 3 C 2 When the catalyst is applied to the hydrogenation deoxidation reaction of palmitic acid, the catalyst Ni/Ti is added 3 C 2 Added to a 1.35wt% n-decane solution of palmitic acid, the reaction conditions were set as follows: temperature 230-350 ℃, 0-5MPa pressure and 2-5h reaction time.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211602972.9A CN115739097B (en) | 2022-12-14 | 2022-12-14 | Efficient catalyst for preparing alkane by hydrodeoxygenation of palmitic acid as well as preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211602972.9A CN115739097B (en) | 2022-12-14 | 2022-12-14 | Efficient catalyst for preparing alkane by hydrodeoxygenation of palmitic acid as well as preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115739097A true CN115739097A (en) | 2023-03-07 |
| CN115739097B CN115739097B (en) | 2023-08-08 |
Family
ID=85345814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211602972.9A Active CN115739097B (en) | 2022-12-14 | 2022-12-14 | Efficient catalyst for preparing alkane by hydrodeoxygenation of palmitic acid as well as preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115739097B (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10967363B1 (en) * | 2017-10-16 | 2021-04-06 | Iowa State University Research Foundation, Inc. | Two-dimensional metal carbide catalyst |
| CN112958095A (en) * | 2021-03-03 | 2021-06-15 | 太原理工大学 | Two-dimensional carrier material loaded catalyst and preparation method and application thereof |
| CN113262789A (en) * | 2021-05-28 | 2021-08-17 | 厦门大学 | Ni/RM hydrodeoxygenation catalyst and preparation method and application thereof |
| CN113441159A (en) * | 2021-07-30 | 2021-09-28 | 陕西科技大学 | Nickel/titanium carbide photo-thermal catalytic material and preparation method and application thereof |
| CN114471646A (en) * | 2021-12-22 | 2022-05-13 | 湘潭大学 | Preparation method and application of single-atom iron-series metal loaded on surface of titanium carbide |
| EP4023331A1 (en) * | 2020-12-30 | 2022-07-06 | Shell Internationale Research Maatschappij B.V. | Hydrogenation catalyst and hydrogenation process |
-
2022
- 2022-12-14 CN CN202211602972.9A patent/CN115739097B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10967363B1 (en) * | 2017-10-16 | 2021-04-06 | Iowa State University Research Foundation, Inc. | Two-dimensional metal carbide catalyst |
| EP4023331A1 (en) * | 2020-12-30 | 2022-07-06 | Shell Internationale Research Maatschappij B.V. | Hydrogenation catalyst and hydrogenation process |
| CN112958095A (en) * | 2021-03-03 | 2021-06-15 | 太原理工大学 | Two-dimensional carrier material loaded catalyst and preparation method and application thereof |
| CN113262789A (en) * | 2021-05-28 | 2021-08-17 | 厦门大学 | Ni/RM hydrodeoxygenation catalyst and preparation method and application thereof |
| CN113441159A (en) * | 2021-07-30 | 2021-09-28 | 陕西科技大学 | Nickel/titanium carbide photo-thermal catalytic material and preparation method and application thereof |
| CN114471646A (en) * | 2021-12-22 | 2022-05-13 | 湘潭大学 | Preparation method and application of single-atom iron-series metal loaded on surface of titanium carbide |
Non-Patent Citations (2)
| Title |
|---|
| HAIGUANG GAO 等: "Interface effect in sandwich like Ni/Ti3C2 catalysts on hydrogen storage performance of MgH2", APPLIED SURFACE SCIENCE, vol. 564, pages 150302 * |
| 左华亮;刘琪英;王铁军;史娜;刘建国;马隆龙;: "负载的Ni催化剂上植物油脂加氢脱氧制备第二代生物柴油", 燃料化学学报, vol. 40, no. 09, pages 1067 - 1073 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115739097B (en) | 2023-08-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105921168B (en) | A kind of preparation method of hydrogenation deoxidation heterogeneous catalyst, hydrogenation deoxidation heterogeneous catalyst and application | |
| CN110117499B (en) | Method for preparing alkane by hydrodeoxygenation of oxygen-containing organic compound | |
| CN112547134B (en) | Polymerization microcrystal catalyst for packaging Cu and Fe oxide and preparation method and application thereof | |
| CN112495424B (en) | Modified molecular sieve supported ruthenium catalyst, preparation thereof and application thereof in preparation of hydrocarbon substances from lignin | |
| Wang et al. | Co-presence of hydrophilic and hydrophobic sites in Ni/biochar catalyst for enhancing the hydrogenation activity | |
| CN112195036B (en) | Method for preparing biodiesel by using seaweed carbon to improve quality of bio-oil | |
| CN110787841B (en) | Super-strong solid acid material containing nitrogen MOFs and application thereof | |
| CN109603908B (en) | Method for preparing aviation oil by catalyzing algal oil hydrothermal reaction through nickel-based sulfonated zeolite organic framework | |
| CN108947786B (en) | Method for preparing acrolein by glycerol dehydration | |
| CN115739097A (en) | Efficient catalyst for preparing alkane by hydrodeoxygenation of palmitic acid and preparation method and application thereof | |
| CN115138392B (en) | Multifunctional biochar catalyst rich in oxygen-containing functional groups and preparation method thereof | |
| CN113663735B (en) | Surface hydrophobization variable-valence copper-based metal organic framework catalyst and preparation method and application thereof | |
| CN112275282B (en) | Preparation method and application of Pt nanoparticle-loaded biochar catalyst | |
| CN107497451A (en) | A kind of preparation method of bamboo charcoal based solid acid catalyst | |
| CN114436809A (en) | Method for preparing diethyl maleate by carrying out depolymerization on lignin under catalysis of iron oxide loaded by USY molecular sieve | |
| CN111203275A (en) | Series reaction catalyst and preparation method and application thereof | |
| CN112191257A (en) | Preparation method of solid acid catalyst and application of catalyst | |
| CN111569889A (en) | Nano zero-valent iron loaded ZnO doped Co3O4Process for preparing catalyst | |
| CN112569945A (en) | Metal-loaded dolomite catalyst for preparing ethanol by glycerol dehydration and preparation thereof | |
| CN113893871B (en) | Preparation method of nitrogen-doped high-dispersivity cobalt catalyst for preparing second-generation biodiesel by oil hydrogenation | |
| CN102059136B (en) | Compound dual-functional catalyst for hydrogenation and esterification reaction of furfural acetic acid and preparation method thereof | |
| CN115608409B (en) | Magnesium-aluminum composite oxide/HZSM-5 dual-function catalyst and preparation method and application thereof | |
| CN116715567B (en) | Preparation method of creosol based on alkali lignin-based catalyst | |
| CN109053357B (en) | Method for catalytically converting poly-3-hydroxybutyrate by using metal oxide | |
| CN115636720A (en) | Method for producing 1, 2-propylene glycol by one-step method catalysis biomass |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |