CN111013593A - In-situ prepared nickel-based catalyst for catalyzing hydrogen absorption and hydrogen desorption of liquid organic hydrogen carrier and preparation method thereof - Google Patents
In-situ prepared nickel-based catalyst for catalyzing hydrogen absorption and hydrogen desorption of liquid organic hydrogen carrier and preparation method thereof Download PDFInfo
- Publication number
- CN111013593A CN111013593A CN202010007967.8A CN202010007967A CN111013593A CN 111013593 A CN111013593 A CN 111013593A CN 202010007967 A CN202010007967 A CN 202010007967A CN 111013593 A CN111013593 A CN 111013593A
- Authority
- CN
- China
- Prior art keywords
- hydrogen
- carrier
- catalyst
- liquid organic
- nickel
- 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
- 239000001257 hydrogen Substances 0.000 title claims abstract description 133
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 133
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 128
- 239000003054 catalyst Substances 0.000 title claims abstract description 69
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 239000007788 liquid Substances 0.000 title claims abstract description 48
- 238000010521 absorption reaction Methods 0.000 title claims abstract description 40
- 229910052759 nickel Inorganic materials 0.000 title claims abstract description 22
- 238000011065 in-situ storage Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000003795 desorption Methods 0.000 title claims description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- 238000010438 heat treatment Methods 0.000 claims abstract description 21
- SNNVSEONCOCCRZ-UHFFFAOYSA-N C1CC=CCCC=C1[Ni]C1=CCCC=CCC1 Chemical compound C1CC=CCCC=C1[Ni]C1=CCCC=CCC1 SNNVSEONCOCCRZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 11
- 230000003197 catalytic effect Effects 0.000 claims abstract description 10
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 5
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 claims description 8
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 8
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910021389 graphene Inorganic materials 0.000 claims description 5
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims 1
- 229910004298 SiO 2 Inorganic materials 0.000 claims 1
- ROOUADGARLQCHR-UHFFFAOYSA-N [Ni]C1=CCCC=CCC1 Chemical compound [Ni]C1=CCCC=CCC1 ROOUADGARLQCHR-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000004914 cyclooctane Substances 0.000 claims 1
- 238000004321 preservation Methods 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 abstract description 5
- 238000003860 storage Methods 0.000 abstract description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 229910052593 corundum Inorganic materials 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 229910001845 yogo sapphire Inorganic materials 0.000 description 6
- 239000000969 carrier Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- HOQAPVYOGBLGOC-UHFFFAOYSA-N 1-ethyl-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2CC HOQAPVYOGBLGOC-UHFFFAOYSA-N 0.000 description 4
- 238000003917 TEM image Methods 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910003158 γ-Al2O3 Inorganic materials 0.000 description 2
- -1 5-Cyclooctadienyl Chemical group 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
Images
Classifications
-
- 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
- B01J23/70—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
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/0005—Reversible uptake of hydrogen by an appropriate medium, i.e. based on physical or chemical sorption phenomena or on reversible chemical reactions, e.g. for hydrogen storage purposes ; Reversible gettering of hydrogen; Reversible uptake of hydrogen by electrodes
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/32—Hydrogen storage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
Abstract
The invention belongs to the technical field of hydrogen storage and catalysis, and particularly relates to an in-situ prepared nickel-based catalyst for catalyzing a liquid organic hydrogen carrier to absorb and discharge hydrogen and a preparation method thereof. The catalyst comprises a catalyst carrier and an active catalytic component loaded on the catalyst carrier, wherein the active catalytic component is nano nickel formed in situ, and the catalyst is prepared by heating and insulating bis (1, 5-cyclooctadienyl) nickel, a reaction solvent liquid organic hydrogen carrier and the catalyst carrier under a vacuum condition, then heating and filling hydrogen for reaction. Compared with the prior art, the invention has the following advantages: (1) no complex catalyst preparation process exists; (2) the catalyst does not use noble metal, but simultaneously shows excellent catalytic performance of catalyzing the hydrogen absorption and the hydrogen release of the liquid organic hydrogen carrier, and has important significance for the practical application of the liquid organic hydrogen carrier.
Description
Technical Field
The invention belongs to the technical field of hydrogen storage and catalysis, and particularly relates to an in-situ prepared nickel-based catalyst for catalyzing a liquid organic hydrogen carrier to absorb and discharge hydrogen and a preparation method thereof.
Background
At present, the energy crisis and the environmental pollution problem are becoming more serious, energy conversion by replacing fossil energy with renewable energy is urgent. The hydrogen energy source, a clean and renewable secondary energy source, is considered as a core pillar in energy transformation. However, the development of hydrogen energy sources is limited by the lack of a sufficiently efficient and safe way of storing hydrogen. The liquid organic hydrogen carrier is one of the most potential hydrogen storage materials at present due to the advantages of high hydrogen storage amount, good reversibility, good thermal conductivity and the like, however, the liquid organic hydrogen carrier generally has the defects of slow hydrogen absorption and desorption kinetics and the need of using expensive noble metal catalysts, and different catalysts are needed in the hydrogen absorption and desorption processes. For example, for N-ethyl carbazole, which is one of the most promising liquid organic hydrogen carriers, Ru-based catalysts and Pd-based catalysts are the best catalysts for hydrogen absorption reaction and hydrogen desorption reaction, respectively.
Therefore, one of the major bottlenecks in catalytic hydrogenation and catalytic dehydrogenation technologies for liquid organic hydrogen carriers is the high cost associated with the use of noble metal catalysts.
Disclosure of Invention
In order to solve the problems in the prior art, an object of the present invention is to provide an in-situ prepared nickel-based catalyst for catalyzing hydrogen absorption and desorption of a liquid organic hydrogen carrier. The nickel-based catalyst can simultaneously and efficiently catalyze the hydrogen absorption and hydrogen desorption reactions of liquid organic hydrogen carriers such as N-ethyl carbazole and the like, and the catalytic performance of the nickel-based catalyst is close to that of a noble metal catalyst, so that the use cost of the liquid organic hydrogen carriers can be greatly reduced, and the practical application of the liquid organic hydrogen carriers is promoted.
The technical scheme adopted for realizing the aim of the invention is as follows: the nickel-based catalyst for catalyzing hydrogen absorption and hydrogen desorption of a liquid organic hydrogen carrier prepared in situ comprises a catalyst carrier and an active catalytic component loaded on the catalyst carrier, wherein the active catalytic component is nano nickel formed in situ, and the catalyst is prepared by heating and insulating bis (1, 5-cyclooctadienyl) nickel, a reaction solvent liquid organic hydrogen carrier and the catalyst carrier under a vacuum condition, then heating and filling hydrogen for reaction.
Preferably, the catalyst is prepared by the following steps:
adding 12-24 mg of bis (1, 5-cyclooctadienyl) nickel, 2.5-5 g of reaction solvent liquid organic hydrogen carrier and 250mg of catalyst carrier into a high-pressure reaction kettle, vacuumizing, detecting leakage, heating, keeping the temperature, continuously heating, filling hydrogen into the reaction kettle for reaction, and thus obtaining the nickel-based catalyst for catalyzing the hydrogen absorption and desorption of the liquid organic hydrogen carrier.
Further preferably, the reaction solvent liquid organic hydrogen carrier of the present invention includes one selected from N-ethyl carbazole, 2-methyl indole or phenazine.
Further preferably, the catalyst carrier of the present invention is selected from Al2O3、SiO2Graphene or C3N4One kind of (1).
The invention also aims to provide a preparation method of the nickel-based catalyst for catalyzing the hydrogen absorption and desorption of the liquid organic hydrogen carrier, which is prepared in situ.
The technical scheme adopted for realizing the other purpose of the invention is as follows: the preparation method of the nickel-based catalyst for catalyzing the hydrogen absorption and the hydrogen desorption of the liquid organic hydrogen carrier, which is prepared in situ, comprises the following preparation steps: adding bis (1, 5-cyclooctadienyl) nickel, a reaction solvent liquid organic hydrogen carrier and a catalyst carrier into a high-pressure reaction kettle, vacuumizing, detecting leakage, heating, preserving heat, heating, and introducing hydrogen for reaction to obtain the nickel-based catalyst for catalyzing the hydrogen absorption and desorption of the liquid organic hydrogen carrier.
Wherein the mass ratio of the bis (1, 5-cyclooctadienyl) nickel to the reaction solvent liquid organic hydrogen carrier to the catalyst carrier is (1-2): (208-417): 21.
the reaction conditions are as follows: heating to 80 ℃, and keeping the temperature for 2 h; heating to 120 ℃ and 180 ℃, filling hydrogen gas to 1-7 MPa, and reacting for 2 h.
In the above-mentioned process for preparing the objective catalyst, the charge amount of each raw material and the reaction conditions may be appropriately changed.
Compared with the prior art, the invention has the following advantages:
(1) no complex catalyst preparation process exists;
(2) the catalyst does not use noble metal, but simultaneously shows excellent catalytic performance of catalyzing the hydrogen absorption and the hydrogen release of the liquid organic hydrogen carrier, and has important significance for the practical application of the liquid organic hydrogen carrier.
Drawings
FIG. 1 shows Ni/Al prepared in example 2 of the present invention2O3X-ray diffraction pattern of (a).
FIG. 2 shows Ni/Al prepared in example 2 of the present invention2O3Transmission electron micrograph (c).
FIG. 3 shows Ni/Al prepared in example 2 of the present invention2O3CatalysisN-kinetic profile of hydrogen uptake and desorption of ethyl carbazole.
FIG. 4 is a schematic diagram of an apparatus for testing hydrogen absorption/desorption kinetic curves of a liquid organic hydrogen carrier according to the present invention.
Detailed Description
The present invention will be described in further detail with reference to the following embodiments.
Example 1
12 mg of bis (1, 5-cyclooctadienyl) nickel (Ni (COD))2）、2.5 gN-ethylcarbazole (NEC) and 250mg of gamma-Al2O3Vacuumizing, detecting leakage, heating to 80 ℃, preserving heat for 2h, heating to 180 ℃, filling 7MPa hydrogen, and reacting for 2h to obtain Ni/Al2O3A catalyst.
Directly catalyzing the catalyst in the reaction kettleNEvaluation of Hydrogen absorption and desorption Performance of-Ethylcarbazole (NEC) the hydrogen absorption reaction of which can be carried out at 180 ℃ under 1MPa H2Under the condition of (1), the reaction is completely carried out for 36H, and the corresponding hydrogen release reaction can be carried out at 200 ℃ and 0.1MPa H2The hydrogen is discharged for 20 h for more than 5.2 wt% (the hydrogen yield is 90%). Testing liquid organic hydrogenThe schematic diagram of the apparatus for the hydrogen absorption and desorption kinetics curve of the carrier is shown in FIG. 4.
Example 2
24 mg of bis (1, 5-cyclooctadienyl) nickel Ni (COD) were charged in an autoclave2、5 gN-ethylcarbazole (NEC) and 250mg of gamma-Al2O3Vacuumizing, detecting leakage, heating to 80 ℃, preserving heat for 2h, heating to 150 ℃, filling 5MPa hydrogen, and reacting for 2h to obtain Ni/Al2O3A catalyst. The Ni/Al2O3The X-ray diffraction spectrum of the catalyst is shown in figure 1, Ni/Al2O3The transmission electron micrograph of (a) is shown in FIG. 2.
Directly catalyzing the catalyst in the reaction kettleNEvaluation of Hydrogen absorption and desorption Performance of Ethyl carbazole (NEC), catalyst Ni/Al2O3CatalysisNThe kinetic profile of hydrogen uptake and desorption of ethyl carbazole is shown in FIG. 3. The hydrogen absorption reaction can be carried out at 180 ℃ and 7 MPaH2Under the condition of (1), the reaction is completely carried out for 20H, and the corresponding hydrogen release reaction can be carried out at 200 ℃ and 0.1MPa H2The hydrogen is discharged for 20 h for more than 5.6 wt% (hydrogen yield 97%). The apparatus for testing the hydrogen absorption and desorption kinetics curves of the liquid organic hydrogen carrier is the same as that of example 1.
Example 3
24 mg of bis (1, 5-cyclooctadienyl) nickel Ni (COD) were charged in an autoclave2、2.5 gNAnd (3) carrying out vacuum pumping and leakage detection on ethyl carbazole (NEC) and 250mg of reduced graphene (rGO), heating to 80 ℃, keeping the temperature for 2h, then heating to 120 ℃, filling 7MPa of hydrogen, and reacting for 2h to obtain the Ni/rGO catalyst.
Directly catalyzing the catalyst in the reaction kettleNEvaluation of Hydrogen absorption and desorption Performance of-Ethylcarbazole (NEC), Hydrogen absorption reaction being capable of 7MPa H at 180 deg.C2Under the condition of (1), the reaction is completely carried out for 20H, and the corresponding hydrogen release reaction can be carried out at 200 ℃ and 0.1MPa H2The hydrogen is discharged for more than 5.5 wt% in 8 h under the condition (the hydrogen yield is 95%). The apparatus for testing the hydrogen absorption and desorption kinetics curves of the liquid organic hydrogen carrier is the same as that of example 1.
Example 4
24 mg of bis (A), (B) was charged into an autoclave1, 5-Cyclooctadienyl) Nickel Ni (COD)22.5 g of phenazine and 250mg of reduced graphene (rGO), vacuumizing, detecting leakage, heating to 80 ℃, preserving heat for 2 hours, heating to 180 ℃, filling 7MPa of hydrogen, and reacting for 2 hours to obtain the Ni/rGO catalyst.
The catalyst is directly subjected to performance evaluation of catalyzing the hydrogen absorption and desorption of the phenazine in the reaction kettle, and the hydrogen absorption reaction can be carried out at 180 ℃ and 7MPa H2Under the condition of (1), the reaction is completely carried out for 10H, and the corresponding hydrogen discharge reaction can be carried out at 200 ℃ and 0.1MPa H2The hydrogen release for 8 h under the condition (7%) is over 7.0 wt%. The apparatus for testing the hydrogen absorption and desorption kinetics curves of the liquid organic hydrogen carrier is the same as that of example 1.
Example 5
24 mg of bis (1, 5-cyclooctadienyl) nickel Ni (COD) were charged in an autoclave22.5 g of 2-methylindole and 250mg of reduced graphene (rGO), vacuumizing, detecting leakage, heating to 80 ℃, preserving heat for 2 hours, heating to 150 ℃, filling 7MPa of hydrogen, and reacting for 2 hours to obtain the Ni/rGO catalyst. The apparatus for testing the hydrogen absorption and desorption kinetics curves of the liquid organic hydrogen carrier is the same as that of example 1.
The performance evaluation of catalyzing 2-methylindole hydrogen absorption and desorption is directly carried out on the catalyst in the reaction kettle, and the hydrogen absorption reaction can be carried out at 150 ℃ and 7MPa H2Under the condition of (1), the reaction is completely carried out for 8H, and the corresponding hydrogen release reaction can be carried out at 200 ℃ and 0.1MPa H2The hydrogen is discharged for more than 5.5 wt% in 8 h under the condition (the hydrogen yield is 95%). The apparatus for testing the hydrogen absorption and desorption kinetics curves of the liquid organic hydrogen carrier is the same as that of example 1.
Claims (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010007967.8A CN111013593B (en) | 2020-01-06 | 2020-01-06 | In-situ prepared nickel-based catalyst for catalyzing hydrogen absorption and desorption of liquid organic hydrogen carrier and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010007967.8A CN111013593B (en) | 2020-01-06 | 2020-01-06 | In-situ prepared nickel-based catalyst for catalyzing hydrogen absorption and desorption of liquid organic hydrogen carrier and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111013593A true CN111013593A (en) | 2020-04-17 |
| CN111013593B CN111013593B (en) | 2022-06-10 |
Family
ID=70198553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010007967.8A Active CN111013593B (en) | 2020-01-06 | 2020-01-06 | In-situ prepared nickel-based catalyst for catalyzing hydrogen absorption and desorption of liquid organic hydrogen carrier and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111013593B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113430420A (en) * | 2021-06-25 | 2021-09-24 | 北京大学 | LaNiAl alloy and preparation method and application thereof |
| CN114804020A (en) * | 2022-05-24 | 2022-07-29 | 苏州清德氢能源科技有限公司 | Slurry hydrogen storage material and preparation method thereof |
| CN115532266A (en) * | 2022-09-27 | 2022-12-30 | 西安交通大学 | A kind of Ni-Cu/AC catalyst and preparation method of indole and its derivatives hydrothermal conversion to gas fuel |
| CN116606240A (en) * | 2023-07-20 | 2023-08-18 | 北京海望氢能科技有限公司 | Hydrogenation reaction method and continuous hydrogenation reaction method |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005000457A2 (en) * | 2003-05-06 | 2005-01-06 | Air Products And Chemicals, Inc. | Hydrogen storage reversible hydrogenated of pi-conjugated substrates |
| JP2005093181A (en) * | 2003-09-16 | 2005-04-07 | Toyota Central Res & Dev Lab Inc | Three-dimensional polymer complex and porous hydrogen storage material comprising the same |
| CN1847152A (en) * | 2005-04-04 | 2006-10-18 | 北京大学 | Rare earth oxide powder with specific surface properties and preparation method thereof |
| US20070128475A1 (en) * | 2005-11-04 | 2007-06-07 | Blacquiere Johanna M | Base metal dehydrogenation of amine-boranes |
| CN101544594A (en) * | 2009-05-13 | 2009-09-30 | 南通海迪化工有限公司 | Method for preparing 3-amino-9-ethyl carbazole by green catalysis method |
| CN106046057A (en) * | 2015-04-07 | 2016-10-26 | 复旦大学 | Azacyclocarbene metal coordination polymer and preparation method thereof, and application of azacyclocarbene metal coordination polymer as catalyst |
| EP3093280A1 (en) * | 2015-05-13 | 2016-11-16 | Sasol Performance Chemicals GmbH | Process for the oligomerisation of olefins by coordinative chain transfer polymerisation and catalyst synthesis |
| CN109097612A (en) * | 2018-09-21 | 2018-12-28 | 北京大学 | A kind of storage hydrogen high-pressure hydrogen storing alloy and preparation method thereof |
-
2020
- 2020-01-06 CN CN202010007967.8A patent/CN111013593B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005000457A2 (en) * | 2003-05-06 | 2005-01-06 | Air Products And Chemicals, Inc. | Hydrogen storage reversible hydrogenated of pi-conjugated substrates |
| JP2005093181A (en) * | 2003-09-16 | 2005-04-07 | Toyota Central Res & Dev Lab Inc | Three-dimensional polymer complex and porous hydrogen storage material comprising the same |
| CN1847152A (en) * | 2005-04-04 | 2006-10-18 | 北京大学 | Rare earth oxide powder with specific surface properties and preparation method thereof |
| US20070128475A1 (en) * | 2005-11-04 | 2007-06-07 | Blacquiere Johanna M | Base metal dehydrogenation of amine-boranes |
| CN101544594A (en) * | 2009-05-13 | 2009-09-30 | 南通海迪化工有限公司 | Method for preparing 3-amino-9-ethyl carbazole by green catalysis method |
| CN106046057A (en) * | 2015-04-07 | 2016-10-26 | 复旦大学 | Azacyclocarbene metal coordination polymer and preparation method thereof, and application of azacyclocarbene metal coordination polymer as catalyst |
| EP3093280A1 (en) * | 2015-05-13 | 2016-11-16 | Sasol Performance Chemicals GmbH | Process for the oligomerisation of olefins by coordinative chain transfer polymerisation and catalyst synthesis |
| CN109097612A (en) * | 2018-09-21 | 2018-12-28 | 北京大学 | A kind of storage hydrogen high-pressure hydrogen storing alloy and preparation method thereof |
Non-Patent Citations (6)
| Title |
|---|
| WU, Y ET AL.: "Promoting hydrogen absorption of liquid organic hydrogen carriers by solid metal hydrides", 《JOURNAL OF MATERIALS CHEMISTRY A 》, 28 July 2019 (2019-07-28), pages 16677 - 16684 * |
| ZHANG, DX ET AL.: "Catalytic hydrogenation of phenanthrene over NiMo/Al2O3 catalysts as hydrogen storage intermediate", 《INTERNATIONAL JOURNAL OF HYDROGEN ENERGY 》, 20 July 2016 (2016-07-20), pages 11675 - 11681 * |
| 姜晓静等: "RE2MgTM2（RE=La,Y;TM=Ni,Cu）金属间化合物储氢性能的研究", 《中国稀土学会2017学术年会摘要集》, 11 May 2017 (2017-05-11), pages 255 * |
| 宋林等: "Ni/γ-Al2O3催化乙基咔唑加氢性能研究", 《化学工程》, 15 October 2015 (2015-10-15), pages 50 - 53 * |
| 杨明等: "液态有机储氢材料加氢脱氢用廉价高效金属催化剂的研究", 《中部四省化学化工学会2016年学术年会摘要集》, 23 September 2016 (2016-09-23), pages 102 * |
| 陆蕴华: "滤色试剂——吩嗪-1-羧酸的制备", 《化学试剂》, 2 March 1982 (1982-03-02), pages 41 - 43 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113430420A (en) * | 2021-06-25 | 2021-09-24 | 北京大学 | LaNiAl alloy and preparation method and application thereof |
| CN113430420B (en) * | 2021-06-25 | 2022-05-06 | 北京大学 | LaNiAl alloy and preparation method and application thereof |
| CN114804020A (en) * | 2022-05-24 | 2022-07-29 | 苏州清德氢能源科技有限公司 | Slurry hydrogen storage material and preparation method thereof |
| CN114804020B (en) * | 2022-05-24 | 2024-08-06 | 苏州清德氢能源科技有限公司 | Slurry hydrogen storage material and preparation method thereof |
| CN115532266A (en) * | 2022-09-27 | 2022-12-30 | 西安交通大学 | A kind of Ni-Cu/AC catalyst and preparation method of indole and its derivatives hydrothermal conversion to gas fuel |
| CN115532266B (en) * | 2022-09-27 | 2023-11-21 | 西安交通大学 | Ni-Cu/AC catalyst for preparing gas fuel by hydrothermally converting indole and derivative thereof and preparation method thereof |
| CN116606240A (en) * | 2023-07-20 | 2023-08-18 | 北京海望氢能科技有限公司 | Hydrogenation reaction method and continuous hydrogenation reaction method |
| CN116606240B (en) * | 2023-07-20 | 2023-10-31 | 北京海望氢能科技有限公司 | Hydrogenation reaction method and continuous hydrogenation reaction method |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111013593B (en) | 2022-06-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111013593A (en) | In-situ prepared nickel-based catalyst for catalyzing hydrogen absorption and hydrogen desorption of liquid organic hydrogen carrier and preparation method thereof | |
| CN113101933B (en) | Supported nickel-cobalt bimetallic nano catalyst and application thereof in catalyzing selective hydrogenation reaction of vanillin | |
| CN108899556B (en) | Method for preparing carbon-nitrogen-based monatomic iron catalyst with assistance of ball milling | |
| US20050002857A1 (en) | Hydrogen storage by reversible hydrogenation of pi-conjugated substrates | |
| US7351395B1 (en) | Hydrogen storage by reversible hydrogenation of pi-conjugated substrates | |
| JP5431647B2 (en) | Hydrogen storage by reversible hydrogenation of pi-conjugated substrates | |
| CN102658131A (en) | Ruthenium-based catalyst for preparing gamma-valerolactone from acetylpropionic acid, and preparation method for ruthenium-based catalyst | |
| Ali et al. | Hydrogenation of dibenzyltoluene and the catalytic performance of Pt/Al2O3 with various Pt loadings for hydrogen production from perhydro‐dibenzyltoluene | |
| CN111013662B (en) | Organic hydrogen storage liquid hydrogenation or dehydrogenation catalyst with enhanced performance of metal hydride and preparation method thereof | |
| CN105217568A (en) | A kind of loading type Ag-Pd/C 3n 4the method of nanocatalyst catalysis formate dehydrogenase | |
| CN111087370A (en) | A method for preparing furfuryl alcohol by non-precious metal supported nitrogen-doped carbon catalyzed transfer hydrogenation of furfural | |
| Xu et al. | Transfer hydrogenation of furfural to furfuryl alcohol over Keggin zirconium-heteropoly acid | |
| CN108133836A (en) | A kind of preparation method and applications of the supported porous carbon material of base metal | |
| CN106824188A (en) | A kind of preparation of tungsten-based catalyst of carrying transition metal and application process | |
| CN111041277B (en) | Rare earth nano hydrogen storage alloy for catalyzing organic hydrogen storage liquid to absorb and discharge hydrogen and preparation method thereof | |
| CN106711468A (en) | Carbon material with catalytic performance on ORR (Oxygen Reduction Reaction) as well as preparation method and application of carbon material | |
| CN111013663B (en) | Transition metal-boron-based catalyst for catalyzing hydrogen absorption and hydrogen desorption of liquid organic hydrogen carrier and preparation method thereof | |
| CN112403472B (en) | Method for preparing carbon-based transition metal hydrogenation catalyst based on pyrolysis bio-oil | |
| CN115108532B (en) | Magnesium-based hydrogen storage material and preparation method thereof | |
| CN112371145B (en) | Two-dimensional carbon nitride photocatalyst containing D-A structure, preparation method and application | |
| CN110229347B (en) | A metal-chelated biporous covalent organic framework material and its preparation and application | |
| CN108722413A (en) | A kind of preparation method and application of yolk-eggshell structure graphite carbon package transition metal material | |
| CN114804020A (en) | Slurry hydrogen storage material and preparation method thereof | |
| CN112547125B (en) | CdS/NiPc photocatalyst for water photolysis and preparation method thereof | |
| CN113926462A (en) | Hydrogenation catalytic material, preparation method and application |
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 | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20220915 Address after: 215500 602, building 6, 88 Xianshi Road, Changshu high tech Industrial Development Zone, Suzhou City, Jiangsu Province Patentee after: Suzhou Qingde Hydrogen Energy Technology Co.,Ltd. Address before: 215500 602, building 6, 88 Xianshi Road, Changshu high tech Industrial Development Zone, Suzhou City, Jiangsu Province Patentee before: Suzhou Mingde New Energy Technology Co.,Ltd. |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20250207 Address after: 528200 R&D Workshop 905-1, Building 10, Lihe Technology Industry Center, No. 99 Taoyuan East Road, Shishan Town, Nanhai District, Foshan City, Guangdong Province (Address Application) Patentee after: Foshan Qingde Hydrogen Energy Technology Co.,Ltd. Country or region after: China Address before: 215500 602, building 6, 88 Xianshi Road, Changshu high tech Industrial Development Zone, Suzhou City, Jiangsu Province Patentee before: Suzhou Qingde Hydrogen Energy Technology Co.,Ltd. Country or region before: China |
|
| TR01 | Transfer of patent right |