CN114180516A - Hydrogen storage material and preparation method thereof - Google Patents
Hydrogen storage material and preparation method thereof Download PDFInfo
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- CN114180516A CN114180516A CN202111406492.0A CN202111406492A CN114180516A CN 114180516 A CN114180516 A CN 114180516A CN 202111406492 A CN202111406492 A CN 202111406492A CN 114180516 A CN114180516 A CN 114180516A
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- carbazole
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- 239000001257 hydrogen Substances 0.000 title claims abstract description 116
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 116
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 113
- 239000011232 storage material Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 238000003860 storage Methods 0.000 claims abstract description 72
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000000543 intermediate Substances 0.000 claims abstract description 29
- 239000007788 liquid Substances 0.000 claims abstract description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 24
- 238000002844 melting Methods 0.000 claims abstract description 19
- 230000008018 melting Effects 0.000 claims abstract description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000009835 boiling Methods 0.000 abstract description 13
- 238000006356 dehydrogenation reaction Methods 0.000 abstract description 5
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 5
- 239000000969 carrier Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- PWJYOTPKLOICJK-UHFFFAOYSA-N 2-methyl-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(C)C=C3NC2=C1 PWJYOTPKLOICJK-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052987 metal hydride Inorganic materials 0.000 description 3
- 150000004681 metal hydrides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DJMRXHOKZAERIV-UHFFFAOYSA-N 3-ethyl-9h-carbazole Chemical compound C1=CC=C2C3=CC(CC)=CC=C3NC2=C1 DJMRXHOKZAERIV-UHFFFAOYSA-N 0.000 description 2
- NQZMCPWRYVQQIT-UHFFFAOYSA-N 4-propan-2-yl-9H-carbazole Chemical compound C(C)(C)C1=CC=CC=2NC3=CC=CC=C3C1=2 NQZMCPWRYVQQIT-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004146 energy storage Methods 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- -1 small-molecule compounds Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
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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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- 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)
- Indole Compounds (AREA)
- Filling Or Discharging Of Gas Storage Vessels (AREA)
- Hydrogen, Water And Hydrids (AREA)
Abstract
The application discloses a hydrogen storage material and a preparation method thereof, the hydrogen storage material comprises an R-carbazole hydrogen storage carrier and an intermediate of the R-carbazole hydrogen storage carrier, the R-carbazole hydrogen storage carrier is at least one of x-methyl carbazole, y-ethyl carbazole, z-isopropyl carbazole, m-tert-butyl carbazole, (m, n) -di-tert-butyl carbazole and a-aminocarbazole, and the intermediate of the R-carbazole hydrogen storage carrier is one or more of low-H or high-H content intermediates of the R-carbazole hydrogen storage carrier. The liquid hydrogen storage carrier provided by the invention is liquid before and after hydrogenation and dehydrogenation reactions, has the melting point of lower than-15 ℃, has the characteristics of high boiling point and low melting point, has high hydrogen storage density, is safe and efficient to store and transport, is environment-friendly, has mature preparation method, and can be applied in large scale.
Description
Technical Field
The application relates to the technical field of hydrogen storage, in particular to a hydrogen storage material and a preparation method thereof.
Background
The hydrogen energy storage is rich, and has the advantages of green, pollution-free, renewable preparation and high energy density, so that the hydrogen energy storage becomes a candidate of ideal energy. The safe and efficient storage and transportation of hydrogen is the key to the large-scale application of hydrogen energy. The existing hydrogen storage technologies include high-pressure gaseous hydrogen storage technology, low-temperature liquid hydrogen storage technology, metal hydride hydrogen storage and the like. Wherein, the high-pressure gaseous hydrogen storage efficiency is very low, in order to obtain the hydrogen storage amount of more than 4.5 wt.%, the pressurization is required to exceed 70MPa, and unsafe factors such as container explosion, easy hydrogen leakage and the like exist in the transportation and use processes; the low-temperature liquid hydrogen storage technology needs to be provided with a corresponding cooling device, the temperature of the liquefied hydrogen needs to be reduced to-252.8 ℃, a large amount of energy needs to be consumed, in order to maintain the low-temperature environment, energy which is equivalent to 30% of the mass energy of the liquid hydrogen is consumed, and the cost of the hydrogen storage mode is high; for metal hydride hydrogen storage, most metal hydrides have high dehydrogenation temperature or low hydrogen storage density, and cannot be applied in scale; liquid hydrogen storage carriers, as represented by carbazole, have the problem of high melting point, which makes them in a solid state without hydrogenation, thus making them impractical for large-scale use.
One of the effective solutions to the above problem is to lower the melting point of such materials so that they are in a liquid state. Generally, the melting point of the mixture can be reduced by adding a low-melting-point solvent, however, since most of the low-melting-point solvents have low boiling points and are mostly organic small-molecule compounds, such as benzene, toluene and the like, side reactions easily occur during the hydrogenation or dehydrogenation reaction of the hydrogen storage carrier, thereby generating organic by-products and impurity gases, such as ring opening and ring breaking phenomena and CO, CH4、C2H6And the hydrogen storage carrier and the purity of hydrogen are seriously influenced, so that the fuel cell cannot normally operate due to poisoning. And the low boiling point solvent can also form steam in the reaction process to take away part of the hydrogen storage carrier, thereby causing the continuous loss of the hydrogen storage carrier. These have severely affected the use of liquid hydrogen storage carriers in the hydrogen energy field.
Therefore, there is a need to invent a hydrogen storage carrier with high boiling point and low melting point to solve the problems faced by the prior art.
Disclosure of Invention
It is an object of the present application to overcome the above problems or to at least partially solve or mitigate the above problems.
According to one aspect of the present application, a high boiling point, low melting point hydrogen storage material is provided.
A hydrogen storage material comprises an R-carbazole hydrogen storage carrier and an intermediate of the R-carbazole hydrogen storage carrier, wherein the R-carbazole hydrogen storage carrier is at least one of x-methylcarbazole, y-ethylcarbazole, z-isopropylcarbazole, m-tert-butylcarbazole, (m, n) -di-tert-butylcarbazole and a-aminocarbazole, and the intermediate of the R-carbazole hydrogen storage carrier is one or more of low-H or high-H content intermediates of the R-carbazole hydrogen storage carrier.
Further, the volume percentage of the R-carbazole hydrogen storage carrier is 1-99%, and the rest is an intermediate of the R-carbazole hydrogen storage carrier.
Preferably, the volume percentage content of the R-carbazole hydrogen storage carrier is 1-65%; the rest is the intermediate of the R-carbazole hydrogen storage carrier. The resulting hydrogen storage material has the highest boiling point and the lowest melting point.
When the R-carbazole hydrogen storage carrier is x-methylcarbazole, the corresponding intermediate is one or more than two of 4H-x-methylcarbazole, 8H-x-methylcarbazole and 12H-x-methylcarbazole, wherein: x is 1,2,3,4 or 9.
When the R-carbazole hydrogen storage carrier is y-ethyl carbazole, the corresponding intermediate is at least one of 4H-y-ethyl carbazole, 8H-y-ethyl carbazole and 12H-y-ethyl carbazole, wherein: y is 1,2,3,4 or 9.
When the R-carbazole hydrogen storage carrier is z-isopropyl carbazole, the corresponding intermediate is at least one of 4H-z-isopropyl carbazole, 8H-z-isopropyl carbazole and 12H-z-isopropyl carbazole, wherein: z is 1,2,3,4 or 9.
When the R-carbazole hydrogen storage carrier is m-tert-butyl carbazole, the corresponding intermediate is at least one of 4H-m-tert-butyl carbazole, 8H-m-tert-butyl carbazole and 12H-m-tert-butyl carbazole, wherein: y is 1,2,3,4 or 9.
When the R-carbazole hydrogen storage carrier is (m, n) -di-tert-butyl carbazole, the corresponding intermediate is at least one of 4H-m, n-di-tert-butyl carbazole, 8H-m, n-di-tert-butyl carbazole and 12H-m, n-di-tert-butyl carbazole, wherein: m and n are (1,8), (2,7), (3,6) or (4, 5).
When the R-carbazole hydrogen storage carrier is a-aminocarbazole, the corresponding intermediate is at least one of 4H-a-aminocarbazole, 8H-a-aminocarbazole and 12H-a-aminocarbazole, wherein: a is 1,2,3,4 or 9.
In another aspect of the present invention, there is also provided a method for preparing a hydrogen storage material, comprising the steps of:
a. placing the R-carbazole hydrogen storage carrier with the volume fraction of 1-99% in a container, and heating and melting to obtain a first solution;
b. placing the intermediate of the R-carbazole hydrogen storage carrier with the volume fraction of 1-99% in another container to obtain a second solution;
c. and pouring the first solution into the second solution, mixing, stirring until the first solution is completely fused, and naturally cooling to room temperature to obtain a mixed liquid, namely the liquid hydrogen storage material at normal temperature and normal pressure.
The heating temperature is 50-120 DEG C
The liquid hydrogen storage material provided by the invention is a mixture of an R-carbazole hydrogen storage carrier and a hydrogen-containing intermediate of the R-carbazole hydrogen storage carrier. Wherein, the R-carbazole hydrogen storage carrier has higher melting point and higher hydrogen storage density, is solid in general, and the hydrogen-containing intermediate is liquid in general and has excellent heat conductivity, and the two are mixed to form a solution with low melting point and high boiling point. The method has the advantages that the method is not only beneficial to large-scale efficient and safe storage and transportation, but also beneficial to filling and releasing of hydrogen, and no impurity gas appears in the reaction process, so that a high-purity product and hydrogen can be obtained, and the method has a large-scale application prospect. In addition, the raw materials required by the invention can be obtained by purchasing.
Detailed Description
The present application is further illustrated by the following specific examples:
example 1
Preparing raw materials according to the following volume fractions:
50% of 2-methyl carbazole; 50% of 4H-2-methylcarbazole;
a method of making a hydrogen storage material comprising the steps of:
a. 2-methylcarbazole with the volume fraction of 50% is placed in a container and heated and melted at the temperature of 80 ℃ to obtain a first solution;
b. putting the 4H-2-methylcarbazole with the volume fraction of 50% in another container to obtain a second solution;
c. and pouring the first solution into the second solution, mixing, stirring until the first solution is completely fused, and naturally cooling to room temperature to obtain a mixed liquid, namely the liquid hydrogen storage material at normal temperature and normal pressure.
According to the invention, the hydrogen storage carrier material of a eutectic system is formed by blending the R-carbazole hydrogen storage carriers with high boiling points and high hydrogen storage capacity and the hydrogen-containing intermediates of the R-carbazole hydrogen storage carriers with different physicochemical characteristics, so that the melting point and the adsorption and desorption kinetics performances are reduced on the basis of keeping the high boiling points and the high hydrogen storage capacity, on one hand, the problems of safe storage and high-efficiency transportation of hydrogen are solved, and on the other hand, the problems of high melting point and low boiling point of the traditional liquid hydrogen storage material are solved.
Example 2
Preparing raw materials according to the following volume fractions:
40% of 3-ethyl carbazole, 30% of 4-isopropyl carbazole, 5% of 8H-3-ethyl carbazole, 10% of 12H-4-propyl carbazole and 15% of 4H-4-isopropyl carbazole;
a method of making a hydrogen storage material comprising the steps of:
a. 3-ethyl carbazole with volume fraction of 40% and 4-isopropyl carbazole with volume fraction of 30% are placed in a container to be heated and melted at 120 ℃, and a first solution is obtained;
b. placing 8H-3-ethyl carbazole with volume fraction of 5%, 12H-4-propyl carbazole with volume fraction of 10% and 4H-4-isopropyl carbazole with volume fraction of 15% in another container to obtain a second solution;
c. and pouring the first solution into the second solution, mixing, stirring until the first solution is completely fused, and naturally cooling to room temperature to obtain a mixed liquid, namely the liquid hydrogen storage material at normal temperature and normal pressure.
Example 3
Preparing raw materials according to the following volume fractions:
20% of (1,8) -di-tert-butyl carbazole, 30% of 4H-1, 8-di-tert-butyl carbazole, and 50% of 8H-1, 8-di-tert-butyl carbazole;
a method of making a hydrogen storage material comprising the steps of:
a. heating and melting (1,8) -di-tert-butyl carbazole with the volume fraction of 20% in a container at 50 ℃ to obtain a first solution;
b. placing 30% volume fraction of 4H-1, 8-di-tert-butyl carbazole and 50% volume fraction of 8H-1, 8-di-tert-butyl carbazole in another container to obtain a second solution;
c. and pouring the first solution into the second solution, mixing, stirring until the first solution is completely fused, and naturally cooling to room temperature to obtain a mixed liquid, namely the liquid hydrogen storage material at normal temperature and normal pressure.
Examples 4 to 8
Preparing raw materials according to the volume fractions in table 1;
the preparation method is the same as example 1.
TABLE 1 batch composition of Hydrogen storage Material for each example
The liquid hydrogen storage material provided by the invention is liquid before and after hydrogenation and dehydrogenation reactions, has the melting point of lower than-15 ℃, has the characteristics of high boiling point and low melting point, has high hydrogen storage density, is safe and efficient to store and transport, is environment-friendly, has mature preparation method, and can be applied in large scale.
The invention can obtain the high-efficiency liquid hydrogen storage carrier material with low melting point and high boiling point by selecting proper carrier matching and proper proportion. A eutectic system formed between hydrogen-containing intermediates of different R-carbazole hydrogen storage carriers and R-carbazole hydrogen storage carriers can bring a series of excellent physical and chemical characteristics, such as high hydrogen storage density, low melting point and high boiling point, and has no side reaction in the process of hydrogenation or dehydrogenation reaction, so that the obtained hydrogen has high purity.
It is to be noted that, unless otherwise specified, technical or scientific terms used herein shall have the ordinary meaning as understood by those skilled in the art to which this application belongs.
The above description is only for the preferred embodiment of the present application, but the scope of the present application is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present application should be covered within the scope of the present application. Therefore, the protection scope of the present application shall be subject to the protection scope of the claims.
Claims (10)
1. A hydrogen storage material, characterized by: the intermediate of the R-carbazole hydrogen storage carrier is one or more than two of low-H or high-H intermediates of the R-carbazole hydrogen storage carrier.
2. A hydrogen storage material as claimed in claim 1, wherein: according to the volume percentage, the volume percentage of the R-carbazole hydrogen storage carrier is 1-99%, and the rest is an intermediate of the R-carbazole hydrogen storage carrier.
3. A hydrogen storage material according to claim 1 or 2, characterized in that:
the volume percentage content of the R-carbazole hydrogen storage carrier is 1-65%; when the R-carbazole hydrogen storage carrier is x-methylcarbazole, the corresponding intermediate is one or more than two of 4H-x-methylcarbazole, 8H-x-methylcarbazole and 12H-x-methylcarbazole, wherein: x is 1,2,3,4 or 9.
4. A hydrogen storage material according to claim 3, characterized in that: when the R-carbazole hydrogen storage carrier is y-ethyl carbazole, the corresponding intermediate is at least one of 4H-y-ethyl carbazole, 8H-y-ethyl carbazole and 12H-y-ethyl carbazole, wherein: y is 1,2,3,4 or 9.
5. A hydrogen storage material according to claim 4, characterized in that: when the R-carbazole hydrogen storage carrier is z-isopropyl carbazole, the corresponding intermediate is at least one of 4H-z-isopropyl carbazole, 8H-z-isopropyl carbazole and 12H-z-isopropyl carbazole, wherein: z is 1,2,3,4 or 9.
6. A hydrogen storage material according to claim 5, characterized in that: when the R-carbazole hydrogen storage carrier is m-tert-butyl carbazole, the corresponding intermediate is at least one of 4H-m-tert-butyl carbazole, 8H-m-tert-butyl carbazole and 12H-m-tert-butyl carbazole, wherein: y is 1,2,3,4 or 9.
7. A hydrogen storage material according to claim 6, characterized in that: when the R-carbazole hydrogen storage carrier is (m, n) -di-tert-butyl carbazole, the corresponding intermediate is at least one of 4H-m, n-di-tert-butyl carbazole, 8H-m, n-di-tert-butyl carbazole and 12H-m, n-di-tert-butyl carbazole, wherein: m and n are (1,8), (2,7), (3,6) or (4, 5).
8. A hydrogen storage material according to claim 7, characterized in that: when the R-carbazole hydrogen storage carrier is a-aminocarbazole, the corresponding intermediate is at least one of 4H-a-aminocarbazole, 8H-a-aminocarbazole and 12H-a-aminocarbazole, wherein: a is 1,2,3,4 or 9.
9. A method of producing a hydrogen storage material according to any one of claims 1 to 8, comprising the steps of:
a. placing the R-carbazole hydrogen storage carrier with the volume fraction of 1-99% in a container, and heating and melting to obtain a first solution;
b. placing the intermediate of the R-carbazole hydrogen storage carrier with the volume fraction of 1-99% in another container to obtain a second solution;
c. and pouring the first solution into the second solution, mixing, stirring until the first solution is completely fused, and naturally cooling to room temperature to obtain a mixed liquid, namely the liquid hydrogen storage material at normal temperature and normal pressure.
10. The method according to claim 9, wherein the heating temperature is 50 to 120 ℃.
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| CN202111406492.0A CN114180516A (en) | 2021-11-24 | 2021-11-24 | Hydrogen storage material and preparation method thereof |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016110215A1 (en) * | 2015-01-06 | 2016-07-14 | 江苏氢阳能源有限公司 | Liquid hydrogen storage system |
| CN106252691A (en) * | 2016-08-27 | 2016-12-21 | 温州集智科技有限公司 | A kind of liquid state organics is as the hydrogen storage electricity generation system of hydrogen storage material |
| CN109353987A (en) * | 2018-11-23 | 2019-02-19 | 汽解放汽车有限公司 | A kind of liquid hydrogen storage material and preparation method thereof |
| CN112028014A (en) * | 2020-09-10 | 2020-12-04 | 云南电网有限责任公司电力科学研究院 | Liquid hydrogen storage material and preparation method thereof |
| CN113336189A (en) * | 2021-07-16 | 2021-09-03 | 西安海望能源科技有限公司 | Liquid hydrogen storage material and preparation method thereof |
-
2021
- 2021-11-24 CN CN202111406492.0A patent/CN114180516A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016110215A1 (en) * | 2015-01-06 | 2016-07-14 | 江苏氢阳能源有限公司 | Liquid hydrogen storage system |
| CN106252691A (en) * | 2016-08-27 | 2016-12-21 | 温州集智科技有限公司 | A kind of liquid state organics is as the hydrogen storage electricity generation system of hydrogen storage material |
| CN109353987A (en) * | 2018-11-23 | 2019-02-19 | 汽解放汽车有限公司 | A kind of liquid hydrogen storage material and preparation method thereof |
| CN112028014A (en) * | 2020-09-10 | 2020-12-04 | 云南电网有限责任公司电力科学研究院 | Liquid hydrogen storage material and preparation method thereof |
| CN113336189A (en) * | 2021-07-16 | 2021-09-03 | 西安海望能源科技有限公司 | Liquid hydrogen storage material and preparation method thereof |
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