CN112390225A - Homogeneous catalytic dehydrogenation method by utilizing interface between aqueous solution and organic liquid hydrogen storage - Google Patents
Homogeneous catalytic dehydrogenation method by utilizing interface between aqueous solution and organic liquid hydrogen storage Download PDFInfo
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- 239000001257 hydrogen Substances 0.000 title claims abstract description 85
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 85
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 84
- 239000007788 liquid Substances 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000006356 dehydrogenation reaction Methods 0.000 title claims abstract description 23
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 17
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 229910052751 metal Inorganic materials 0.000 claims abstract description 28
- 239000002184 metal Substances 0.000 claims abstract description 28
- 239000011232 storage material Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- -1 salt chloride Chemical class 0.000 claims description 6
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 4
- QFSMMXJBEBXTJP-UHFFFAOYSA-N 7-benzyl-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCNCC1 QFSMMXJBEBXTJP-UHFFFAOYSA-N 0.000 claims description 3
- KVSWZGISCXEZGZ-UHFFFAOYSA-N C(C)C1=CC=CC=2C3=CC=CC=C3NC12.[N] Chemical compound C(C)C1=CC=CC=2C3=CC=CC=C3NC12.[N] KVSWZGISCXEZGZ-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- SZKMTZNASRXXCE-UHFFFAOYSA-N [2-[2-(diphenylphosphanylmethyl)phenyl]phenyl]methyl-diphenylphosphane Chemical compound C=1C=CC=C(C=2C(=CC=CC=2)CP(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 SZKMTZNASRXXCE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- FTTNHUULIMOCKS-WAYWQWQTSA-N n-[(z)-3-acetamidobut-2-en-2-yl]acetamide Chemical compound CC(=O)N\C(C)=C(\C)NC(C)=O FTTNHUULIMOCKS-WAYWQWQTSA-N 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 229910001510 metal chloride Inorganic materials 0.000 claims description 2
- 230000006378 damage Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 229910021645 metal ion Inorganic materials 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract 2
- 238000012360 testing method Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 2
- 238000007210 heterogeneous catalysis Methods 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
Classifications
-
- 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
- C01B3/001—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 characterised by the uptaking medium; Treatment thereof
- C01B3/0015—Organic compounds; Solutions thereof
-
- 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
- C01B3/50—Separation of hydrogen or hydrogen containing gases from gaseous mixtures, e.g. purification
- C01B3/52—Separation of hydrogen or hydrogen containing gases from gaseous mixtures, e.g. purification by contacting with liquids; Regeneration of used liquids
- C01B3/54—Separation of hydrogen or hydrogen containing gases from gaseous mixtures, e.g. purification by contacting with liquids; Regeneration of used liquids including a catalytic reaction
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Catalysts (AREA)
- Hydrogen, Water And Hydrids (AREA)
Abstract
The invention discloses a method for carrying out homogeneous catalytic dehydrogenation by utilizing an interface between aqueous solution and organic liquid hydrogen storage, which is a reaction system consisting of a liquid hydrogen storage material, a metal salt catalyst, aqueous solution and a hydrogen-containing high-pressure reaction kettle, and realizes the dehydrogenation of the liquid hydrogen storage material. The method takes water as a solvent, exerts the advantages of high solubility of the hydrosolvent to the metal ion catalyst and similar density to the organic liquid hydrogen storage material, is beneficial to fully expanding a reaction interface, improving the reaction activity, reducing the reaction temperature, and being beneficial to the separation of the catalyst and a product, and has the advantages of difficult damage of the catalyst structure, cyclic utilization, mild reaction conditions, high catalytic activity, good selectivity and the like.
Description
Technical Field
The invention belongs to the field of liquid hydrogen storage, and particularly relates to a homogeneous catalytic dehydrogenation method by utilizing an aqueous solution and organic liquid hydrogen storage interface.
Background
Hydrogen, the lightest element on earth, is very low in density whether it exists in a gaseous or liquid state. As a fuel, the utilization of hydrogen energy has the characteristics of dispersibility, intermittency and the like, so the problems of storage and transportation of the hydrogen energy are to be solved. To achieve large-scale storage and utilization of hydrogen energy, hydrogen storage systems need to have the following characteristics: high hydrogen storage density, flexible and convenient use requirements and a safe and reliable hydrogen storage mode.
At present, the common hydrogen storage technologies include high-pressure gaseous hydrogen storage, low-temperature liquid hydrogen storage, metal hydride hydrogen storage, metal organic matter skeleton compound hydrogen storage, organic liquid hydrogen storage, and the like. The organic liquid hydrogen storage material is an effective means for realizing large-scale hydrogen storage and long-distance delivery of hydrogen energy due to a safe and efficient hydrogen storage mode. Compared with the traditional hydrogen storage method, the organic liquid has high hydrogen storage capacity and density, low requirements on temperature and pressure, good reversibility, recyclable reactants and products, similar properties to gasoline, and can be transported and stored by imitating the existing infrastructure such as pipelines, gas stations and the like.
At present, most of catalytic hydrogenation/dehydrogenation reactions researched by liquid organic hydrogen storage materials are heterogeneous reactions, and the mass transfer problem in the reactions becomes a main bottleneck restricting the hydrogenation/dehydrogenation efficiency. Therefore, it is necessary to increase the temperature and speed up the mass transfer process so that the reaction proceeds more thoroughly. However, an excessively high temperature increases the storage cost of hydrogen energy on the one hand, and causes side reactions such as destruction of the pore structure of the catalyst material and decomposition of the organic liquid on the other hand.
Disclosure of Invention
The invention aims to solve the problem of solubility of an organic liquid hydrogen storage material, improve the conductivity of electrolyte and provide a hydrogen source through an auxiliary agent, improve the reaction activity, reduce the reaction temperature and pressure and realize the defect of electrochemical hydrogenation of the hydrogen storage material, and provides a method for homogeneous catalytic dehydrogenation by utilizing an aqueous solution and an organic liquid hydrogen storage interface.
The invention adopts the following technical scheme:
a method for homogeneous catalytic dehydrogenation by utilizing an aqueous solution and organic liquid hydrogen storage interface is characterized in that: the dehydrogenation of the liquid hydrogen storage material is realized by a reaction system which consists of the liquid hydrogen storage material, a metal salt catalyst, an aqueous solution and a hydrogen-containing high-pressure reaction kettle.
Preferably, the method comprises the following steps:
s1, adding deionized water into a density reaction kettle;
s2, adding a metal salt catalyst into deionized water, and fully stirring until the metal salt catalyst is dissolved;
s3, adding the organic hydrogen storage material to be dehydrogenated into a reaction kettle, and fully stirring;
s4, fully introducing nitrogen into the reaction kettle, sealing, continuously magnetically stirring, heating at a certain temperature, and collecting and removing hydrogen;
s5, after no gas is separated out, cooling the reaction kettle to room temperature, standing until a water phase and an organic phase are layered, and separating out a dehydrogenation product.
Preferably, the metal salt in the metal salt catalyst is Pt, Cr, Co, Fe, Mo, W, Rh, Ru, Ir, Pd, Ni, Ti, Ta, Ag, etc. and their corresponding chlorides.
Preferably, the metal salt catalyst is a water-soluble metal salt chloride catalyst of diphosphine ligand, and the diphosphine ligand is any one or combination of DPPM, BDPX, BISBI and BDNA.
Preferably, the organic hydrogen storage material is hydrogenated organic solution such as nitrogen-ethyl carbazole, nitrogen-propyl carbazole, pyrazine, indole, and the like.
Preferably, the heating temperature of step S4 is 100-150 ℃.
Has the advantages that: the invention provides a method for homogeneous catalytic dehydrogenation by utilizing an aqueous solution and organic liquid hydrogen storage interface, which takes water as a solvent, exerts the advantages of high solubility of a hydrosolvent to a metal ion catalyst and similar density to an organic liquid hydrogen storage material, is favorable for fully expanding a reaction interface, improving the reaction activity, reducing the reaction temperature, and is favorable for separating the catalyst and a product, and has the advantages of difficult damage of the catalyst structure, cyclic utilization, mild reaction conditions, high catalytic activity, good selectivity and the like.
Detailed Description
The present invention will be described in further detail with reference to the following examples:
a method for homogeneous catalytic dehydrogenation by utilizing an aqueous solution and organic liquid hydrogen storage interface is characterized in that: the dehydrogenation of the liquid hydrogen storage material is realized by a reaction system which consists of the liquid hydrogen storage material, a metal salt catalyst, an aqueous solution and a hydrogen-containing high-pressure reaction kettle.
Preferably, the method comprises the following steps:
s1, adding deionized water into a density reaction kettle;
s2, adding a metal salt catalyst into deionized water, and fully stirring until the metal salt catalyst is dissolved;
s3, adding the organic hydrogen storage material to be dehydrogenated into a reaction kettle, and fully stirring;
s4, fully introducing nitrogen into the reaction kettle, sealing and continuously magnetically stirring, heating at the temperature of 100-150 ℃, and collecting and removing hydrogen;
s5, after no gas is separated out, cooling the reaction kettle to room temperature, standing until a water phase and an organic phase are layered, and separating out a dehydrogenation product.
In specific implementation, the metal salt in the metal salt catalyst is Pt, Cr, Co, Fe, Mo, W, Rh, Ru, Ir, Pd, Ni, Ti, Ta, Ag, and the like and metal chlorides corresponding to the metal; the metal salt catalyst is a water-soluble metal salt chloride catalyst of a diphosphine ligand, wherein the diphosphine ligand is any one or a combination of DPPM, BDPX, BISBI and BDNA; the organic hydrogen storage material is hydrogenated organic solution of nitrogen-ethyl carbazole, nitrogen-propyl carbazole, pyrazine, indole and the like.
Example 1:
adding RuCl2(DPPM)2(4mg) was thoroughly dispersed in (20mL) deionized water, 5g of dodecahydroethylcarbazole was added, and the reaction mixture was placed in a closed reactionAnd introducing nitrogen into the container, sealing, fully stirring, heating to 90 ℃, collecting hydrogen released in the reaction along with the change of time, and testing the hydrogen release amount in the reaction system. Through tests, the hydrogen release rate is relatively high in 1-30min, and the hydrogen release amount is 0.11mol and is 75.9% of the maximum hydrogen release amount. As the reaction proceeded, by the end of 50min, the final hydrogen evolution was 0.13mol, which was 89.6% of the maximum hydrogen evolution. After the reaction is finished, cooling to room temperature, and standing for separation to realize separation of the catalyst layer and the organic liquid.
Example 2:
the procedure and conditions were the same as in example 1 except that the reactor temperature was increased to 110 deg.C, and it was found through the test that the hydrogen release rate was fast from 1 to 30min, the hydrogen release amount was 0.12mol, which is 82.8% of the maximum hydrogen release amount, and the reaction was terminated after 43min, the final hydrogen release amount was 0.14mol, which is 96.6% of the maximum hydrogen release amount.
Example 3:
for comparison with the traditional heterogeneous catalysis, the steps and conditions are the same as those in example 1 except that deionized water is not added into the reaction system, and tests show that the hydrogen release rate is relatively high in 1-30min, the hydrogen release amount is 0.05mol and is 34.5% of the maximum hydrogen release amount, and the reaction is finished after 60min, and the final hydrogen release amount is 0.08mol and is 55.2% of the maximum hydrogen release amount.
Example 4
Comparative example 1 illustrates the catalytic effect of different metals. The experimental method is the same as that of example 4, except that Fe is used as a central metal instead of Ru, and tests show that the hydrogen release rate is high in 1-30min, the hydrogen release amount is 0.07mol and is 48.3% of the maximum hydrogen release amount, and the reaction is finished after 60min, and the final hydrogen release amount is 0.09mol and is 62.1% of the maximum hydrogen release amount.
According to the above embodiments, it can be seen that: in the organic liquid hydrogen storage material dehydrogenation method, compared with the traditional heterogeneous catalysis, the homogeneous catalysis reaction has faster reaction rate and higher reaction degree; compared with non-noble metals, noble metals adopted by the metal salt catalyst have higher catalytic efficiency; and according to the reaction principle, the method can be used for the hydrogenation process of the organic liquid hydrogen storage material under the condition of changing the temperature condition and the pressure.
Finally, it should be noted that the above-mentioned description is only a preferred embodiment of the present invention, and those skilled in the art can make various similar representations without departing from the spirit and scope of the present invention.
Claims (6)
1. A method for homogeneous catalytic dehydrogenation by utilizing an aqueous solution and organic liquid hydrogen storage interface is characterized by comprising the following steps: the dehydrogenation of the liquid hydrogen storage material is realized by a reaction system which consists of the liquid hydrogen storage material, a metal salt catalyst, an aqueous solution and a hydrogen-containing high-pressure reaction kettle.
2. The method of claim 1, comprising the steps of:
s1, adding deionized water into a density reaction kettle;
s2, adding a metal salt catalyst into deionized water, and fully stirring until the metal salt catalyst is dissolved;
s3, adding the organic hydrogen storage material to be dehydrogenated into a reaction kettle, and fully stirring;
s4, fully introducing nitrogen into the reaction kettle, sealing, continuously magnetically stirring, heating at a certain temperature, and collecting and removing hydrogen;
s5, after no gas is separated out, cooling the reaction kettle to room temperature, standing until a water phase and an organic phase are layered, and separating out a dehydrogenation product.
3. A method for the homogeneous catalytic dehydrogenation using an aqueous solution and organic liquid hydrogen storage interface according to claim 1 or 2, characterized in that: the metal salt in the metal salt catalyst is Pt, Cr, Co, Fe, Mo, W, Rh, Ru, Ir, Pd, Ni, Ti, Ta, Ag and the like and metal chlorides corresponding to the metal.
4. The method of claim 3, wherein the method comprises the step of performing homogeneous catalytic dehydrogenation by using an interface between the aqueous solution and the organic liquid hydrogen storage material, wherein the interface comprises: the metal salt catalyst adopts a water-soluble metal salt chloride catalyst of diphosphine ligand, and the diphosphine ligand is any one or combination of DPPM, BDPX, BISBI and BDNA.
5. The method of claim 1, wherein the method comprises the step of performing homogeneous catalytic dehydrogenation by using an interface between an aqueous solution and an organic liquid hydrogen storage medium, wherein the interface comprises: the organic hydrogen storage material is hydrogenated organic solution of nitrogen-ethyl carbazole, nitrogen-propyl carbazole, pyrazine, indole and the like.
6. The method of claim 2, wherein the method comprises the step of performing homogeneous catalytic dehydrogenation by using an interface between the aqueous solution and the organic liquid hydrogen storage material, wherein the interface comprises: the heating temperature of step S4 is 100-150 ℃.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115417374A (en) * | 2022-10-19 | 2022-12-02 | 云南电网有限责任公司电力科学研究院 | Dehydrogenation method and dehydrogenation device for organic liquid hydrogen storage material |
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