CN112028014A - Liquid hydrogen storage material and preparation method thereof - Google Patents
Liquid hydrogen storage material and preparation method thereof Download PDFInfo
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- CN112028014A CN112028014A CN202010950092.5A CN202010950092A CN112028014A CN 112028014 A CN112028014 A CN 112028014A CN 202010950092 A CN202010950092 A CN 202010950092A CN 112028014 A CN112028014 A CN 112028014A
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- hydrogen storage
- carbazole
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 91
- 239000001257 hydrogen Substances 0.000 title claims abstract description 91
- 239000007788 liquid Substances 0.000 title claims abstract description 30
- 239000011232 storage material Substances 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title abstract description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000000654 additive Substances 0.000 claims abstract description 29
- 230000000996 additive effect Effects 0.000 claims abstract description 26
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims abstract description 12
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims abstract description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 5
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- SDFLTYHTFPTIGX-UHFFFAOYSA-N 9-methylcarbazole Chemical compound C1=CC=C2N(C)C3=CC=CC=C3C2=C1 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 claims description 4
- LSZJZNNASZFXKN-UHFFFAOYSA-N 9-propan-2-ylcarbazole Chemical compound C1=CC=C2N(C(C)C)C3=CC=CC=C3C2=C1 LSZJZNNASZFXKN-UHFFFAOYSA-N 0.000 claims description 4
- -1 N-N-propylcarbazole Chemical compound 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 238000002844 melting Methods 0.000 abstract description 16
- 230000008018 melting Effects 0.000 abstract description 16
- 238000006356 dehydrogenation reaction Methods 0.000 abstract description 10
- 230000005496 eutectics Effects 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 10
- QAWLNVOLYNXWPL-UHFFFAOYSA-N 9-propylcarbazole Chemical compound C1=CC=C2N(CCC)C3=CC=CC=C3C2=C1 QAWLNVOLYNXWPL-UHFFFAOYSA-N 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 3
- LCZUOKDVTBMCMX-UHFFFAOYSA-N 2,5-Dimethylpyrazine Chemical compound CC1=CN=C(C)C=N1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000001934 2,5-dimethylpyrazine Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- 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)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Inorganic Chemistry (AREA)
- Filling Or Discharging Of Gas Storage Vessels (AREA)
- Hydrogen, Water And Hydrids (AREA)
Abstract
The invention relates to a liquid hydrogen storage material and a preparation method thereof, wherein the liquid hydrogen storage material comprises carbazole hydrogen storage components and a heat conduction additive with low melting point and high heat transfer coefficient; the low-melting-point heat-conducting additive component is at least one of pyrazine and derivatives thereof or naphthyridine and derivatives thereof. The liquid hydrogen storage material is prepared by mixing the carbazole hydrogen storage component with high melting point and the heat conduction additive with low melting point, and the formed mixture has a eutectic point at least lower than the melting point of one component, so that the melting point of the whole hydrogen storage material can be reduced to below 0 ℃. Meanwhile, the low-melting-point additive has low dehydrogenation reaction temperature, and does not cause the reduction of hydrogen storage density after being mixed with the carbazole hydrogen storage components.
Description
Technical Field
The invention relates to the technical field of hydrogen storage, in particular to a liquid hydrogen storage material and a preparation method thereof.
Background
The hydrogen energy is a clean renewable energy source and has the characteristics of storage and transportation. The existing hydrogen storage methods mainly comprise high-pressure hydrogen storage, organic liquid hydrogen storage, metal alloy hydrogen storage, adsorption hydrogen storage, composite hydrogen storage and the like. In terms of the prior art, the organic liquid hydrogen storage not only has higher hydrogen storage density, but also has the characteristics of transportability and low cost. The organic liquid hydrogen storage technology has large hydrogen storage capacity, can realize the storage, transportation and maintenance of hydrogen at normal temperature and normal pressure, is convenient to utilize the existing oil storage and transportation equipment, and can be recycled for many times.
In the prior art, liquid organic hydrogen storage with better application prospect is a system based on carbazole and derivatives thereof, and although carbazole organic matters have higher hydrogen storage density, the carbazole organic matters have over-high melting points and are solid at room temperature, so that the hydrogen storage system recovered after hydrogenation and in the dehydrogenation process is easy to condense into solid after preferential dehydrogenation. These condensates tend to coat the surface of the dehydrogenation catalyst, thereby causing the dehydrogenation reaction to be interrupted. In order to lower the melting point, some additives are usually needed to be added, and at present, the additives are mainly aromatic compounds, but the temperature of the aromatic compound additives and dehydrogenation reaction is too high, thereby inevitably causing the reduction of hydrogen storage density.
For the above reasons, it is necessary to provide an additive which is liquid at room temperature and is easy to dehydrogenate, so as to solve the problems of difficult dehydrogenation and reduced hydrogen storage density caused by easy solidification of a liquid organic hydrogen storage system.
Disclosure of Invention
In view of the above technical problems in the prior art, the present invention aims to provide a liquid hydrogen storage material and a preparation method thereof.
A first aspect of embodiments of the present application illustrates a liquid hydrogen storage material comprising:
the heat-conducting additive is formed by mixing one or more of pyrazine and derivatives thereof or naphthyridine and derivatives thereof.
Alternatively, the carbazole-based hydrogen storage component comprises: one or more of carbazole, N-methylcarbazole, N-ethylcarbazole, N-N-propylcarbazole, N-isopropylcarbazole or N-N-butylcarbazole.
Optionally, the molecular structure general formula of the heat conducting additive is:
wherein R is1，R2,R3,R4,R5,R6Is alkyl, alkoxy and halide with 1-10 carbon atoms independently.
A second aspect of the embodiments of the present application shows a method for preparing a liquid hydrogen storage material, comprising:
slowly adding a heat-conducting additive with the mass fraction of 5-90% into the molten carbazole hydrogen storage component until the filling is finished to obtain a mixed material;
stopping heating, and cooling the mixed material to room temperature to obtain the hydrogen storage material.
Optionally, the method further comprises:
putting 10-95% by mass of carbazole hydrogen storage components into a three-necked bottle, heating to 70-300 ℃, after the carbazole hydrogen storage components are melted, putting magnetons into the carbazole hydrogen storage components, and stirring.
The invention relates to a liquid hydrogen storage material and a preparation method thereof, wherein the liquid hydrogen storage material comprises carbazole hydrogen storage components and a heat conduction additive with low melting point and high heat transfer coefficient; the low-melting-point heat-conducting additive component is at least one of pyrazine and derivatives thereof or naphthyridine and derivatives thereof. The liquid hydrogen storage material is prepared by mixing the carbazole hydrogen storage component with high melting point and the heat conduction additive with low melting point, and the formed mixture has a eutectic point at least lower than the melting point of one component, so that the melting point of the whole hydrogen storage material can be reduced to below 0 ℃. Meanwhile, the low-melting-point additive has low dehydrogenation reaction temperature, and does not cause reduction of hydrogen storage density when being mixed with carbazole hydrogen storage components.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art that other drawings can be obtained according to these drawings without creative efforts.
FIG. 1 is a graph showing the change in hydrogen storage density with time.
Detailed Description
In order to make the technical solutions in the embodiments of the present invention better understood and make the above objects, features and advantages of the embodiments of the present invention more comprehensible, the technical solutions in the embodiments of the present invention are described in further detail below with reference to the accompanying drawings.
A first aspect of embodiments of the present application illustrates a liquid hydrogen storage material comprising:
the heat-conducting additive is formed by mixing one or more of pyrazine and derivatives thereof or naphthyridine and derivatives thereof.
Alternatively, the carbazole-based hydrogen storage component comprises: one or more of carbazole, N-methylcarbazole, N-ethylcarbazole, N-N-propylcarbazole, N-isopropylcarbazole or N-N-butylcarbazole.
Optionally, the molecular structure general formula of the heat conducting additive is:
wherein R is1，R2,R3,R4,R5,R6Is alkyl, alkoxy and halide with 1-10 carbon atoms independently.
The technical solutions shown in the embodiments of the present application are described in detail below with reference to specific examples.
Example 1:
the hydrogen storage system formed by taking N-propylcarbazole and 2, 5-dimethylpyrazine as hydrogen storage components has the following eutectic point:
example 2:
the hydrogen storage system formed by taking N-propylcarbazole and quinoxaline as hydrogen storage components has the following eutectic point:
example 3:
the hydrogen storage system formed by taking N-propylcarbazole, N-ethylcarbazole and quinoxaline as hydrogen storage components has the following eutectic point:
the following is a quantitative analysis of the hydrogen rate of the liquid hydrogen storage material provided herein with reference to specific data.
N-propylcarbazole and N-ethylcarbazole (2:1) are used as a hydrogen storage system 1; taking N-propylcarbazole and quinoxaline (4:1) as a hydrogen storage system 2, taking N-propylcarbazole, N-ethylcarbazole and quinoxaline (2:1:2) as a hydrogen storage system 3, respectively taking 2g, and taking Ru-Al under the hydrogen of 8MPa2O3When the catalyst is used as a catalyst for hydrogenation reaction, the results of the change of the hydrogen storage density in the three systems along with the time can be seen in figure 1, and the curve shows that the hydrogenation rate of the system 3 is fastest, the hydrogenation can be completed within about 2.5 hours, and the hydrogenation in the other two systems within 3 hours is not completed; from the rate, the hydrogenation rate of the system can be effectively improved by adding quinoxaline.
The liquid hydrogen storage material can be prepared by the following method, and comprises the following steps:
putting the carbazole hydrogen storage component into a three-necked bottle, heating to 70-300 ℃, after the carbazole hydrogen storage component is melted, putting a magneton into the carbazole hydrogen storage component, and stirring to obtain a mixed material; slowly adding the low-melting-point heat-conducting additive into the mixed material until the filling is finished, and continuously stirring for 3-5 hours; and D, stopping heating, and cooling the mixed material in the step B to room temperature to obtain the hydrogen storage material.
Further, the carbazole-based hydrogen storage component is at least one of carbazole, N-methylcarbazole, N-ethylcarbazole, N-N-propylcarbazole, N-isopropylcarbazole and N-N-butylcarbazole.
Further, relative to the total mass of the liquid hydrogen storage material, the mass fraction of the carbazole hydrogen storage component is 10-95%, and the mass fraction of the low-melting-point heat-conducting additive is 5-90%.
Further, the low-melting-point heat-conducting additive component is at least one of pyrazine and derivatives thereof or naphthyridine and derivatives thereof.
Compared with the prior art, the invention has the beneficial effects that: the liquid hydrogen storage material is a mixture of a liquid carbazole hydrogen storage component and a low-melting-point heat-conducting additive. After the high-melting-point carbazole hydrogen storage component and the low-melting-point heat conduction additive are mixed, the formed mixture has a eutectic point at least lower than the melting point of one component, so that the melting point of the whole hydrogen storage material can be reduced to be below 0 ℃; meanwhile, the low-melting-point heat-conducting additive has better dehydrogenation performance and can not cause the reduction of hydrogen storage density.
As can be seen from the above embodiments, the liquid hydrogen storage material of the present invention is a mixture of a liquid carbazole-based hydrogen storage component and a low-melting-point heat-conducting additive. After the high-melting-point carbazole hydrogen storage component and the low-melting-point heat conduction additive are mixed, the formed mixture has a eutectic point at least lower than the melting point of one component, so that the melting point of the whole hydrogen storage material can be reduced to be below 0 ℃; meanwhile, the low-melting-point heat-conducting additive has better dehydrogenation performance and can not cause the reduction of hydrogen storage density. While there have been shown and described what are at present considered the fundamental principles and essential features of the invention and its advantages, it will be apparent to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, but is capable of other specific forms without departing from the spirit or essential characteristics thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
The embodiments of the present invention are described in detail, and the embodiments are only examples of the general inventive concept, and should not be construed as limiting the scope of the present invention. Any other embodiments extended by the solution according to the invention without inventive step will be within the scope of protection of the invention for a person skilled in the art.
Claims (5)
1. A liquid hydrogen storage material, comprising:
the heat-conducting additive is formed by mixing one or more of pyrazine and derivatives thereof or naphthyridine and derivatives thereof.
2. A liquid hydrogen storage material according to claim 1,
the carbazole-based hydrogen storage component comprises: one or more of carbazole, N-methylcarbazole, N-ethylcarbazole, N-N-propylcarbazole, N-isopropylcarbazole or N-N-butylcarbazole.
3. The liquid hydrogen storage material of claim 1, wherein the molecular structural formula of the heat conducting additive is:
wherein R is1，R2,R3,R4,R5,R6Is alkyl, alkoxy and halide with 1-10 carbon atoms independently.
4. A method of preparing a liquid hydrogen storage material, comprising:
slowly adding a heat-conducting additive with the mass fraction of 5-90% into the molten carbazole hydrogen storage component until the filling is finished to obtain a mixed material;
stopping heating, and cooling the mixed material to room temperature to obtain the hydrogen storage material.
5. The method of claim 4, further comprising:
putting 10-95% by mass of carbazole hydrogen storage components into a three-necked bottle, heating to 70-300 ℃, after the carbazole hydrogen storage components are melted, putting magnetons into the carbazole hydrogen storage components, and stirring.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113753850A (en) * | 2021-07-29 | 2021-12-07 | 苏州中车氢能动力技术有限公司 | Application of monomethyl quinoxaline compound, preparation method thereof, hydrogenation method and dehydrogenation method of monomethyl quinoxaline compound |
| CN114180516A (en) * | 2021-11-24 | 2022-03-15 | 株洲铂陆新能源科技有限公司 | Hydrogen storage material and preparation method thereof |
| CN114735643A (en) * | 2022-05-07 | 2022-07-12 | 北京瀚锐氢能科技有限公司 | Organic liquid hydrogen storage material and performance regulation method and application thereof |
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2020
- 2020-09-10 CN CN202010950092.5A patent/CN112028014A/en active Pending
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| CN114180516A (en) * | 2021-11-24 | 2022-03-15 | 株洲铂陆新能源科技有限公司 | Hydrogen storage material and preparation method thereof |
| CN114735643A (en) * | 2022-05-07 | 2022-07-12 | 北京瀚锐氢能科技有限公司 | Organic liquid hydrogen storage material and performance regulation method and application thereof |
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Application publication date: 20201204 |