CN110040685A - A kind of liquid organic hydrogen storage material and preparation method - Google Patents
A kind of liquid organic hydrogen storage material and preparation method Download PDFInfo
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- CN110040685A CN110040685A CN201910356696.4A CN201910356696A CN110040685A CN 110040685 A CN110040685 A CN 110040685A CN 201910356696 A CN201910356696 A CN 201910356696A CN 110040685 A CN110040685 A CN 110040685A
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- 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
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- 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
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Abstract
This application discloses a kind of liquid organic hydrogen storage material and preparation methods, the material includes: low melting point liquid organic compound, solid-state organic compound and solubilizer, the mass fraction of the low melting point liquid organic compound are as follows: 40%~90%, the mass fraction of the solid-state organic compound are as follows: 5%~40%, the mass fraction of the solubilizer are as follows: 1%~20%；Wherein, the low melting point liquid organic compound is a benzyl toluene and/or dibenzyl toluene, and the solid-state organic compound is naphthalene and/or pyrene, and the solubilizer is benzene and/or toluene.It is low melting point liquid (fusing point≤- 25 DEG C) before and after adding hydrogen, there is the features such as storage and transportation is convenient, safe, and use environment adaptability is good, and material component and preparation method are simple, and recycling property is good.
Description
Technical field
This application involves hydrogen storage technology fields, more particularly to liquid organic hydrogen storage material and preparation method.
Background technique
Hydrogen energy source is due to having many advantages, such as that resourceful, pollution-free, renewable, energy density is high, it is considered to be ideal
The energy.In recent years, with the pressure of the shortage of fossil fuel, the requirement of environment and sustainable development, the exploitation and benefit of Hydrogen Energy
It is become more and more important with seeming.Currently, Main Countries have formulated hydrogen energy source exploitation plan.The numerous related enterprises in the whole world
Industry, scientific research institution are all in the exploitation dynamics for increasing hydrogen energy source industry.Hydrogen Energy industrial system mainly include hydrogen production, storage and
Transport, using etc. links.Therefore, the large-scale application of Hydrogen Energy needs to solve cheap convenient hydrogen scale technology of preparing, safety
Three critical issues such as Hydrogen Energy export technique of reliable hydrogen storaging and transport technology, high efficient and reliable.Develop at present from Hydrogen Energy industry existing
From the point of view of shape and future developing trend, the safe and efficient storage of hydrogen is the key that hydrogen utilization, and the hair of Hydrogen Energy industrialization at present
The major technology bottleneck of exhibition.
The memory technology of hydrogen can be divided into physical method and two kinds of chemical method, and physical method mainly includes high-pressure gaseous hydrogen storage, low
Warm liquid hydrogen storage, hydrogen physisorption etc..Chemical method mainly includes metal alloy hydrogen storage, organic liquid hydrogen storage, methanol recapitalization system
Hydrogen, metal hydride/complex compound hydrolytic hydrogen production etc..In recent years, the organic liquid hydrogen storage technology based on chemical reaction method is with its storage
Hydrogen density is high, safety is good, the concern of Many researchers is caused using the advantages that convenient transportation.Existing liquid hydrogen storage body
System, two different hydrogen storage components, hydrogen storage group are divided into unsaturated aromatic hydrocarbon or heterocycle unsaturated compound.The liquid hydrogen storage system
Actually Diversity liquid condensed hetero ring aromatic hydrocarbons hydrogen storage system, disadvantage is that the hydrogen storage material system is in dehydrogenation reaction mistake
Side reaction easily occurs for Cheng Zhong, heterocyclic compound component therein, generates the foreign gases components such as nitrogen oxides, oxysulfide,
Cause the purity of hydrogen that requirement is not achieved.In addition, the impurity compositions such as nitrogen oxides, oxysulfide are to fuel cell membrane electrode
With irreversible toxic action, thus the hydrogen storage material system is limited in the application of fuel cell field.
Summary of the invention
Aiming to overcome that the above problem or at least being partially solved or extenuate for the application solves the above problems.
According to the one aspect of the application, a kind of liquid organic hydrogen storage material is provided, comprising: low melting point liquid organises
Close object, solid-state organic compound and solubilizer, the mass fraction of the low melting point liquid organic compound are as follows: 40%~90%,
The mass fraction of the solid-state organic compound are as follows: 5%~40%, the mass fraction of the solubilizer are as follows: 1%~20%；Its
In, the low melting point liquid organic compound is a benzyl toluene and/or dibenzyl toluene, and the solid-state organic compound is naphthalene
And/or pyrene, the solubilizer are benzene and/or toluene.
In one embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 40%, it is described
The mass fraction of solid-state organic compound are as follows: 40%, the mass fraction of the solubilizer are as follows: 20%.
In one embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 90%, it is described
The mass fraction of solid-state organic compound are as follows: 8%, the mass fraction of the solubilizer are as follows: 2%.
In one embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 60%, it is described
The mass fraction of solid-state organic compound are as follows: 30%, the mass fraction of the solubilizer are as follows: 10%.
In one embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 50%, it is described
The mass fraction of solid-state organic compound are as follows: 35%, the mass fraction of the solubilizer are as follows: 15%.
In one embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 65%, it is described
The mass fraction of solid-state organic compound are as follows: 22%, the mass fraction of the solubilizer are as follows: 13%.
In one embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 70%, it is described
The mass fraction of solid-state organic compound are as follows: 16%, the mass fraction of the solubilizer are as follows: 14%.
In one embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 80%, it is described
The mass fraction of solid-state organic compound are as follows: 13%, the mass fraction of the solubilizer are as follows: 7%.
In one embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 85%, it is described
The mass fraction of solid-state organic compound are as follows: 12%, the mass fraction of the solubilizer are as follows: 3%.
According to further aspect of the application, a kind of preparation method of liquid organic hydrogen storage material is provided, including following
Step:
Adaptation step: first under room temperature, condition of normal pressure, successively will in ratio of any of claims 1-9
Low melting point liquid organic compound, solid-state organic compound and solubilizer are added in stirred tank；
Reaction step: being passed through high pure nitrogen or argon gas to stirred tank, blows down air and forms gas atmosphere, then opens
Heating mantle is opened, is warming up to 60 DEG C with the rate of 1-5 DEG C/min, while at the uniform velocity stirring with the speed of 60~200rpm 60~
300min is cooled to room temperature after the completion of stirring, filling after release.
The liquid organic hydrogen storage material of the application, by low melting point liquid organic compound, solid-state organic compound and increasing
Solvent composition, the mass fraction of low melting point liquid organic compound are as follows: 40%~90%, the mass fraction of solid-state organic compound
Are as follows: 5%~40%, the mass fraction of solubilizer are as follows: 1%~20%；Wherein, low melting point liquid organic compound is a benzyl first
Benzene and/or dibenzyl toluene, solid-state organic compound are naphthalene and/or pyrene, and solubilizer is benzene and/or toluene.Before and after adding hydrogen
For low melting point liquid, have storage and transportation convenient, safe, use environment adaptability is good, and material component and preparation method are simple, follows
The features such as ring usability is good.
Detailed description of the invention
Some specific embodiments of the application are described in detail by way of example and not limitation with reference to the accompanying drawings hereinafter.
Identical appended drawing reference denotes same or similar part or part in attached drawing.It should be appreciated by those skilled in the art that these
What attached drawing was not necessarily drawn to scale.In attached drawing:
Fig. 1 is the flow chart according to the preparation method of the liquid organic hydrogen storage material of the application one embodiment.
Specific embodiment
The application's in a first aspect, provide a kind of liquid organic hydrogen storage material, comprising: low melting point liquid organic compound
Object, solid-state organic compound and solubilizer, the mass fraction of the low melting point liquid organic compound are as follows: 40%~90%, institute
State the mass fraction of solid-state organic compound are as follows: 5%~40%, the mass fraction of the solubilizer are as follows: 1%~20%；Wherein,
The low melting point liquid organic compound be a benzyl toluene and/or dibenzyl toluene, the solid-state organic compound be naphthalene and/
Or pyrene, the solubilizer are benzene and/or toluene.It is low melting point liquid (fusing point≤- 25 DEG C) before and after adding hydrogen, there is storage
The features such as fortune is convenient, safe, and use environment adaptability is good, and material component and preparation method are simple, and recycling property is good.
High, low in cost, the safe and convenient to use liquid of the hydrogen-storage density height of the application, good environmental adaptability, hydrogen purity
State organic hydrogen storage material.
In this embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 40%, it is described solid
The mass fraction of state organic compound are as follows: 40%, the mass fraction of the solubilizer are as follows: 20%.By proportion optimizing, there is hydrogen
The features such as gas storage density is high, hydrogen storage material preparation facilitates.
In this embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 90%, it is described solid
The mass fraction of state organic compound are as follows: 8%, the mass fraction of the solubilizer are as follows: 2%.By proportion optimizing, there is former material
Expect the features such as at low cost, hydrogen storage material fusing point is low, good environmental adaptability.
In this embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 60%, it is described solid
The mass fraction of state organic compound are as follows: 30%, the mass fraction of the solubilizer are as follows: 10%.By proportion optimizing, there is storage
The features such as hydrogen density is high, hydrogen purity is high.
In this embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 50%, it is described solid
The mass fraction of state organic compound are as follows: 35%, the mass fraction of the solubilizer are as follows: 15%.By proportion optimizing, there is storage
The features such as hydrogen density is high, hydrogen purity is high.
In this embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 65%, it is described solid
The mass fraction of state organic compound are as follows: 22%, the mass fraction of the solubilizer are as follows: 13%.By proportion optimizing, there is storage
The features such as hydrogen density is high, the preparation time is short.
In this embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 70%, it is described solid
The mass fraction of state organic compound are as follows: 16%, the mass fraction of the solubilizer are as follows: 14%.By proportion optimizing, there is storage
The features such as hydrogen density is high, the preparation time is short.
In this embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 80%, it is described solid
The mass fraction of state organic compound are as follows: 13%, the mass fraction of the solubilizer are as follows: 7%.By proportion optimizing, having makes
With good environmental adaptability, prepare the features such as facilitating.
In this embodiment, optionally, the mass fraction of the low melting point liquid organic compound are as follows: 85%, it is described solid
The mass fraction of state organic compound are as follows: 12%, the mass fraction of the solubilizer are as follows: 3%.By proportion optimizing, having makes
With good environmental adaptability, prepare the features such as simple, safety is good.
In this embodiment, optionally, the raw material of the liquid organic hydrogen storage material by following mass percent wt% into
Row weighs: a benzyl toluene: 45%, pyrene: 40% and toluene: 15%, have that use environment adaptability is good, prepares simple, safety
The features such as property is good.
Preparation method: under room temperature, condition of normal pressure, stirred tank successively is added in a benzyl toluene, pyrene, toluene in proportion
In, be then passed through high pure nitrogen to stirred tank, blow down air and simultaneously form gas atmosphere, later on heating mantle, with 1 DEG C/
The rate of min is warming up to 60 DEG C, while at the uniform velocity stirring 60min with the speed of 60rpm, is cooled to room temperature after the completion of stirring, release
It is filling afterwards.Have the characteristics that preparing process is simple, high production efficiency, safe operation.
In this embodiment, optionally, the raw material of the liquid organic hydrogen storage material by following mass percent wt% into
Row weighs: a benzyl toluene: 10%, dibenzyl toluene: 30%, naphthalene: 40% and toluene: 20%, have materials'use Environmental
Well, the features such as hydrogen-storage density is high.
Preparation method: under room temperature, condition of normal pressure, successively a benzyl toluene, dibenzyl toluene naphthalene, toluene are added in proportion
Enter in stirred tank, be then passed through high pure nitrogen to stirred tank, blow down air and forms gas atmosphere, later on heating
Set is warming up to 60 DEG C with the rate of 5 DEG C/min, while at the uniform velocity stirring 300min with the speed of 60rpm, is cooled to after the completion of stirring
Room temperature, it is filling after release.Have the characteristics that easy to operate, process flow is easy.
In this embodiment, optionally, the raw material of the liquid organic hydrogen storage material by following mass percent wt% into
Row weighs: a benzyl toluene: 40%, dibenzyl toluene: 40%, naphthalene: 5%, pyrene: 5%, benzene: 5% and toluene: 5%, there is storage
The features such as hydrogen density height, good environmental adaptability.
Preparation method: under room temperature, condition of normal pressure, successively a benzyl toluene, dibenzyl toluene naphthalene, toluene are added in proportion
Enter in stirred tank, be then passed through high pure nitrogen to stirred tank, blow down air and forms gas atmosphere, later on heating
Set is warming up to 60 DEG C with the rate of 4 DEG C/min, while at the uniform velocity stirring 100min with the speed of 200rpm, cooling after the completion of stirring
It is filling after release to room temperature.Have the characteristics that process flow is simple, high production efficiency.
The second aspect of the application, as shown in Figure 1, a kind of preparation method of liquid organic hydrogen storage material is provided, including
Following steps:
S10 adaptation step: first under room temperature, condition of normal pressure, in ratio described in first aspect successively by low melting point liquid
State organic compound, solid-state organic compound and solubilizer are added in stirred tank；
S20 reaction step: being passed through high pure nitrogen or argon gas to stirred tank, blows down air and forms gas atmosphere, with
After open heating mantle, be warming up to 60 DEG C with the rate of 1-5 DEG C/min, while at the uniform velocity stirring with the speed of 60~200rpm 60~
300min is cooled to room temperature after the completion of stirring, filling after release.The features such as process flow is simple, production safety coefficient is high.
It should be noted that unless otherwise indicated, technical term or scientific term used in this application should be this Shen
It please the ordinary meaning that is understood of one of ordinary skill in the art.
The preferable specific embodiment of the above, only the application, but the protection scope of the application is not limited thereto,
Within the technical scope of the present application, any changes or substitutions that can be easily thought of by anyone skilled in the art,
Should all it cover within the scope of protection of this application.Therefore, the protection scope of the application should be with scope of protection of the claims
Subject to.
Claims (10)
1. a kind of liquid organic hydrogen storage material characterized by comprising
Low melting point liquid organic compound, solid-state organic compound and solubilizer；
The mass fraction of the low melting point liquid organic compound are as follows: 40%~90%；
The mass fraction of the solid-state organic compound are as follows: 5%~40%；
The mass fraction of the solubilizer are as follows: 1%~20%；
Wherein, the low melting point liquid organic compound is a benzyl toluene and/or dibenzyl toluene, the solid-state organic compound
Object is naphthalene and/or pyrene, and the solubilizer is benzene and/or toluene.
2. liquid organic hydrogen storage material according to claim 1, it is characterised in that:
The mass fraction of the low melting point liquid organic compound are as follows: 40%；
The mass fraction of the solid-state organic compound are as follows: 40%；
The mass fraction of the solubilizer are as follows: 20%.
3. liquid organic hydrogen storage material according to claim 1, it is characterised in that:
The mass fraction of the low melting point liquid organic compound are as follows: 90%；
The mass fraction of the solid-state organic compound are as follows: 8%；
The mass fraction of the solubilizer are as follows: 2%.
4. liquid organic hydrogen storage material according to claim 1, it is characterised in that:
The mass fraction of the low melting point liquid organic compound are as follows: 60%；
The mass fraction of the solid-state organic compound are as follows: 30%；
The mass fraction of the solubilizer are as follows: 10%.
5. liquid organic hydrogen storage material according to claim 1, it is characterised in that:
The mass fraction of the low melting point liquid organic compound are as follows: 50%；
The mass fraction of the solid-state organic compound are as follows: 35%；
The mass fraction of the solubilizer are as follows: 15%.
6. liquid organic hydrogen storage material according to claim 1, it is characterised in that:
The mass fraction of the low melting point liquid organic compound are as follows: 65%；
The mass fraction of the solid-state organic compound are as follows: 22%；
The mass fraction of the solubilizer are as follows: 13%.
7. liquid organic hydrogen storage material according to claim 1, it is characterised in that:
The mass fraction of the low melting point liquid organic compound are as follows: 70%；
The mass fraction of the solid-state organic compound are as follows: 16%；
The mass fraction of the solubilizer are as follows: 14%.
8. liquid organic hydrogen storage material according to claim 1, it is characterised in that:
The mass fraction of the low melting point liquid organic compound are as follows: 80%；
The mass fraction of the solid-state organic compound are as follows: 13%；
The mass fraction of the solubilizer are as follows: 7%.
9. liquid organic hydrogen storage material according to claim 1, it is characterised in that:
The mass fraction of the low melting point liquid organic compound are as follows: 85%；
The mass fraction of the solid-state organic compound are as follows: 12%；
The mass fraction of the solubilizer are as follows: 3%.
10. a kind of method for preparing the liquid organic hydrogen storage material as described in any one of claim 1-9, which is characterized in that packet
Include following steps:
Adaptation step: first under room temperature, condition of normal pressure, in ratio of any of claims 1-9 successively by eutectic
Point liquid organic compound, solid-state organic compound and solubilizer are added in stirred tank；
Reaction step: being passed through high pure nitrogen or argon gas to stirred tank, blows down air and forms gas atmosphere, later on to add
Hot jacket is warming up to 60 DEG C with the rate of 1-5 DEG C/min, while at the uniform velocity stirring 60~300min with the speed of 60~200rpm, stirs
It is cooled to room temperature after the completion of mixing, it is filling after release.
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| CN201910356696.4A CN110040685B (en) | 2019-04-29 | 2019-04-29 | Liquid organic hydrogen storage material |
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| CN113845086A (en) * | 2020-06-28 | 2021-12-28 | 中国石油化工股份有限公司 | Liquid hydrogen storage material and preparation method and application thereof |
| CN114436208A (en) * | 2022-01-30 | 2022-05-06 | 北京东方红升新能源应用技术研究院有限公司 | Catalytic hydrogen supply system based on organic liquid and hydrogen supply method thereof |
| CN114497630A (en) * | 2022-01-30 | 2022-05-13 | 北京东方红升新能源应用技术研究院有限公司 | Organic liquid material for hydrogen storage, catalytic hydrogen storage system and hydrogen storage method |
| CN114477081A (en) * | 2020-10-27 | 2022-05-13 | 中国石油化工股份有限公司 | Liquid hydrogen storage material and preparation method and application thereof |
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| FR3117114B1 (en) * | 2020-12-09 | 2024-04-12 | Arkema France | LIQUID FORMULATION FOR HYDROGEN STORAGE |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113845086A (en) * | 2020-06-28 | 2021-12-28 | 中国石油化工股份有限公司 | Liquid hydrogen storage material and preparation method and application thereof |
| CN114477081A (en) * | 2020-10-27 | 2022-05-13 | 中国石油化工股份有限公司 | Liquid hydrogen storage material and preparation method and application thereof |
| CN114477081B (en) * | 2020-10-27 | 2024-03-26 | 中国石油化工股份有限公司 | Liquid hydrogen storage material and preparation method and application thereof |
| CN114436208A (en) * | 2022-01-30 | 2022-05-06 | 北京东方红升新能源应用技术研究院有限公司 | Catalytic hydrogen supply system based on organic liquid and hydrogen supply method thereof |
| CN114497630A (en) * | 2022-01-30 | 2022-05-13 | 北京东方红升新能源应用技术研究院有限公司 | Organic liquid material for hydrogen storage, catalytic hydrogen storage system and hydrogen storage method |
| CN114497630B (en) * | 2022-01-30 | 2023-11-21 | 北京东方红升新能源应用技术研究院有限公司 | Organic liquid material for hydrogen storage, catalytic hydrogen storage system and hydrogen storage method |
| CN114436208B (en) * | 2022-01-30 | 2023-12-05 | 北京东方红升新能源应用技术研究院有限公司 | Catalytic hydrogen supply system based on organic liquid and hydrogen supply method thereof |
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| CN110040685B (en) | 2020-09-25 |
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