CN113372566A - For lifting AlH3Stable functionalized MOFs material, and preparation method and application thereof - Google Patents
For lifting AlH3Stable functionalized MOFs material, and preparation method and application thereof Download PDFInfo
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- CN113372566A CN113372566A CN202110752344.8A CN202110752344A CN113372566A CN 113372566 A CN113372566 A CN 113372566A CN 202110752344 A CN202110752344 A CN 202110752344A CN 113372566 A CN113372566 A CN 113372566A
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- 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
- Y02E60/32—Hydrogen storage
Abstract
The invention belongs to AlH3The field of hydrogen-containing energy storage materials, and discloses a method for improving AlH3Stable TEMPO free radical trapping agent functionalized MOFs materials and a preparation method and an application method thereof. The functionalized MOFs material comprises: metal organic framework material matrix UiO-66-NH2And radical scavenger 2,2,6, 6-tetramethylpiperidine nitroxide (TEMPO). The preparation method comprises the following steps: the metal organic framework material matrix UiO-66-NH is added2Reacting with diisocyanate to obtain active MOFs with end group of isocyanic acid radical; then the isocyanate and amino-substituted TEMPO are subjected to esterification reaction. The invention discloses a preparation method of the functionalized MOFs material, and the functionalized MOFs material is applied to improve AlH3And its effectiveness was verified by correlation characterization tests. The functionalized MOFs material has the advantages of low cost, easy preparation, nano-scale and the likeIs characterized by reacting with AlH3Can improve the stability after grinding and mixing, and is particularly suitable for AlH3Application in solid rocket propellants.
Description
Technical Field
The invention belongs to the field of hydrogen storage high-energy materials, and relates to a functionalized MOFs material suitable for improving the stability of AlH3, and a preparation method and application thereof.
Background
The replacement of the aluminum powder fuel commonly used at present by a higher energy fuel is an important way to improve the energy performance of the solid propellant. Aluminum trihydride (AlH)3) Has the obvious advantages of high hydrogen content, large combustion heat, good gas production performance, environmental protection, no toxicity, low flame signal and the like, and uses AlH3The replacement of aluminium powder can significantly improve the specific impulse of solid propellants, and therefore the development of AlH-based propellants3Solid propellants for high energy fuels are of great interest.
AlH3Al and H atoms in the crystal are connected through covalent bonds, but the covalent bonds are unstable, and can be gradually broken under the conditions of light, heat or long-time storage and the like, so that hydrogen atoms are separated from AlH3Dissociating in molecule to generate hydrogen and metallic aluminium, so that AlH3Decomposition, crystal structure destruction, and great damage to AlH3High energy properties of (2). How to prepare AlH with high stability3Is one of the key challenges in achieving practical application of such high energy fuels in propellants.
In recent years, researchers have attempted to promote AlH in different ways3Stability of (2). For example: 1) doping method: by reaction at AlH3The AlH can be improved by doping elements such as magnesium, silicon, mercury and the like3Thermal stability of (2). The research shows that the AlH is not doped with magnesium under the test condition of 60 DEG C3The time for 1% decomposition was 6 days, however in AlH3After 2% of magnesium is added, the time can be increased to 26 days. 2) Surface coating method: coating a layer of organic or inorganic material on the surface of AlH3 to isolate AlH3Contact with air or moisture can increase AlH3Stability of (2). Belf et al reported a diphenylacetylene coated AlH3Method of (1), discoveryCoated AlH3Than uncoated AlH3The thermal stability of the product is about doubled. 3) Surface treatment: the AlH can be purified by treatment such as inorganic acid washing or organic solution washing3Surface, increasing AlH3Stability of (2). 4) And (3) crystal form control: known as AlH3Has 8 phases, among which alpha-AlH3Is the most stable phase known. By reaction at AlH3During the preparation process, the additive is added to promote the alpha-AlH3Crystallization, inhibition of AlH in other phase3Can increase the generation of AlH3Stability of (2).
AlH promotion reported at present3The stability method improves AlH to some extent3Stability, but to really solve AlH3The stability problem of (a) also requires a more efficient process.
Disclosure of Invention
For AlH3The invention provides a method for improving AlH, which is used as a solid propellant and has the stability problem3Stable functionalized MOFs materials. The functionalized MOFs material adopts a nano-scale metal organic framework material matrix UiO-66-NH2The surface of the substrate is grafted with TEMPO free radical trapping agent. The functionalized MOFs material has larger specific surface area and nano-sized crystal grain size, and is mixed with AlH3After grinding and mixing, the AlH can be improved3Stability of (2).
The purpose of the invention is realized by the following technical scheme:
the invention provides a method for improving AlH3A stable functionalized MOFs material, comprising the following components: nanoscale metal organic framework material matrix UiO-66-NH2And a surface grafted TEMPO radical scavenger. The TEMPO radical trapping agent has strong trapping capacity on surrounding hydrogen radical active species, and can be covalently combined with the surrounding hydrogen radical active species to generate dormant species, so that AlH can be improved3Stability of (2).
The invention also provides a preparation method of the functionalized MOFs material, which comprises the following steps:
the metal organic framework material matrix UiO-66-NH is added2Dissolving the active MOFs and diisocyanate in an anhydrous DMF solution, and stirring to react for 6-8 h to obtain active MOFs with an end group of isocyanic acid radical; and dissolving the active MOFs with the end group of isocyanic acid radical and amino-substituted TEMPO in an anhydrous DMF solution according to a specific molar ratio, and stirring for reaction for 12 hours to obtain the TEMPO functionalized MOFs material.
Preferably, the active MOFs of isocyanate group are reacted with amino-substituted TEMPO (H)2N-TEMPO) in a molar ratio of 1: 0.5 to 1.5. The stirring reaction is carried out at the temperature of 30-50 ℃. When the temperature is higher than 50 ℃ or lower than 30 ℃, the functionalization effect of MOFs surface grafting TEMPO is reduced.
Preferably, the metal organic framework material matrix UiO-66-NH2The preparation method comprises the following steps:
zirconium tetrachloride, 2-amino terephthalic acid and benzoic acid are mixed according to a molar ratio of 1: 1: 20 is dissolved in DMF solution, then the solution is put into a stainless steel hydrothermal reaction kettle to be uniformly mixed, and the mixture is reacted for 24 hours at the temperature of 120 ℃; slowly cooling until the temperature is reduced to room temperature to obtain yellow powder, centrifugally cleaning the powder for 3-4 times by using a DMF (dimethyl formamide) solution, and removing unreacted ligands and metal ions; soxhlet extracting with ethanol as extractant for three days, removing residual DMF solution to obtain solid powder; drying and activating the obtained solid powder at 60 ℃ for 8 h.
The invention also provides a method for improving AlH by applying the functionalized MOFs material provided by the invention3The method of stability is as follows: the functionalized MOFs material and AlH3Fully grinding and mixing according to a specific proportion, thus improving AlH3The heat release hydrogen stability. Preferably, the functionalized MOFs material and AlH3The mass ratio of grinding and mixing is 1-10%. When the mass ratio of the two components is not in this range, AlH3The overall performance of (a) may be degraded. When the mass ratio is more than 1: at 10, AlH3The combustion performance and energy density of (2) may be reduced; when the mass ratio is less than 1: 100 hours, AlH3The stability of (2) may be reduced.
Definition of terms
The term "room temperature" as used herein means a temperature range of 25. + -. 5 ℃.
All ranges cited herein are inclusive, unless expressly stated to the contrary. For example, the temperature of the stirring reaction is 30-50 ℃, which means that the value range of the temperature is more than or equal to 30 ℃ and less than or equal to 50 ℃.
The terms "a" or "an" are used herein to describe elements and components described herein. This is done merely for convenience and to provide a general sense of the scope of the invention. Such description should be understood to include one or at least one and the singular also includes the plural unless it is obvious that it is meant otherwise.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. For example: TEMPO, known as 2,2,6, 6-tetramethylpiperidine oxide, is an organic nitrogen oxide of the formula C9H18 NO; MOFs materials are short for metal organic framework compound materials; soxhlet extraction refers to extraction using a Soxhlet extraction apparatus (Soxhlet extraction apparatus).
Compared with the prior art, the invention has the following beneficial effects:
1) can effectively promote AlH3The MOFs material with thermolysis hydrogen stability and TEMPO radical trapping agent functionalization and AlH3After being fully ground and mixed, the free radicals and AlH can be blocked3Reacting to promote AlH3The heat release hydrogen stability.
2) The TEMPO functionalized MOFs reserve the structural advantages of MOFs materials, have nano-scale grain size and large specific surface area, and ensure that the TEMPO radical trapping agent can be fully mixed with AlH3The contact and interaction are strong, and the AlH can be stabilized only by a small amount of functionalized MOFs3The purpose of (1).
3) A good active free radical research platform is provided for MOFs materials through TEMPO functionalization, and AlH of free radical trapping agents can be researched in real time3The capture of middle free radical, the interaction and the minactization of free radical and the change of the surrounding environment of free radical are important information, which is favorable for the deep understanding of AlH3The mechanism of stabilization of (1).
Drawings
Other features, objects and advantages of the invention will become more apparent upon reading of the detailed description of non-limiting embodiments with reference to the following drawings:
FIG. 1 is Electron Paramagnetic Resonance (EPR) spectra of MOFs before and after TEMPO functionalization according to example 1;
FIG. 2 is an X-ray diffraction (XRD) pattern of MOFs material before and after TEMPO functionalization of example 1;
Detailed Description
The present invention will be described in detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications can be made by persons skilled in the art without departing from the spirit of the invention. All falling within the scope of the present invention.
The invention provides a method for improving AlH3A stable functionalized MOFs material, comprising the following components: nanoscale metal organic framework material matrix UiO-66-NH2And a TEMPO radical scavenger for surface grafting. The TEMPO radical trapping agent has strong trapping capacity on surrounding hydrogen radical active species, and can be covalently combined with the surrounding hydrogen radical active species to generate dormant species, so that AlH can be improved3Stability of (2).
The invention also provides a preparation method of the functionalized MOFs material, which comprises the following steps:
step 1: zirconium tetrachloride, 2-amino terephthalic acid and benzoic acid are mixed according to a molar ratio of 1: 1: dissolving 20 in a DMF solution, then putting the solution into a stainless steel hydrothermal reaction kettle, uniformly mixing, reacting for 24 hours at 120 ℃, slowly cooling until the temperature is reduced to room temperature to obtain yellow powder, centrifugally cleaning the powder for 3-4 times by using the DMF solution, and removing unreacted ligands and metal ions; soxhlet extracting with ethanol as extractant for three days, removing residual DMF solution to obtain solid powder; drying and activating the obtained solid powder at 60 ℃ for 8h to obtain a nanoscale metal organic framework material matrixUiO-66-NH2；
Step 2: preparing the prepared nanoscale metal organic framework material matrix UiO-66-NH2Stirring and reacting with isocyanate at a specific temperature to obtain active MOFs with an end group of isocyanic acid radical;
step 3: active MOFs with end group of isocyanic acid radical and amino substituted TEMPO (H)2N-TEMPO) according to a specific molar ratio and at a specific temperature for 12 hours to obtain TEMPO functionalized MOFs.
Preferably, the active MOFs of isocyanate group in the functionalization process and amino-substituted TEMPO (H)2N-TEMPO) in a molar ratio of 1: 0.5-1.5, wherein the stirring reaction temperature in the Step2 and the Step3 is 30-50 ℃. After the functionalized MOFs material prepared under the condition is ground and mixed with AlH3, AlH is subjected to grinding3The thermal stability improvement effect of (2) can be equivalent to that of the following embodiment.
TEMPO functionalized MOFs material and AlH3Mixing and grinding according to a specific proportion, and carrying out AlH after grinding uniformly3Thermal stability test of (2). Preferably, the TEMPO functionalized MOFs material and AlH3Is 1 to 10% by mass, under which condition AlH is present3The thermal stability improvement effect of (2) can be equivalent to that of the following embodiment.
Example 1
The synthesis of the TEMPO functionalized MOFs material of this example is as follows:
8g of a matrix UiO-66-NH of a metal-organic framework material2Dissolving the powder in 30ml of anhydrous DMF, adding 15ml of isocyanate, stirring for 6 hours at 30 ℃ in a sealed anhydrous environment to obtain an active MOFs solution with an end group of isocyanate, and repeatedly centrifuging and cleaning the solution for 4-5 times by using the anhydrous DMF solution to obtain an active MOFs solid. Please refer to fig. 1, which shows Electron Paramagnetic Resonance (EPR) spectra of MOFs materials before and after TEMPO functionalization; the triplet width peak at g-2.006 in the spectrum is consistent with the peak of the TEMPO free radical, which shows that the TEMPO free radical is successfully grafted on the surface of the MOFs material by the functionalization method of example 1. FIG. 2 is an X-ray diffraction (XRD) pattern of MOFs material before and after TEMPO functionalization, and from the XRD pattern, the functionalized MOFs material can be seenThe material is completely matched with the characteristic peak position of the MOFs material before functionalization, which shows that the crystal structure of the MOFs material is not changed in the functionalization process, and TEMPO free radicals are successfully grafted on the surface.
TEMPO (H) substituted according to active MOFs with amino groups2N-TEMPO) in a molar ratio of 1: 1.5, then dissolving the sample in 30ml of anhydrous DMF, and stirring for 12 hours at 30 ℃ in a closed anhydrous environment to obtain the TEMPO functionalized MOFs material. Then TEMPO functionalized MOFs material and AlH3According to the mass ratio of 1: 100, heating at 60 deg.C for 72 hr, and measuring modified AlH by draining method3Volume of hydrogen evolved.
Measuring AlH added with the functionalized modified MOFs material after heating for 72h in an air atmosphere at 60 ℃ by a drainage method3The volume of hydrogen released was 80 ml.
Example 2
In the same manner as in example 1, in the preparation method of the TEMPO functionalized MOFs material of this embodiment, H is added when TEMPO is grafted on the surface of the MOFs2The molar ratio of N-TEMPO to MOFs was also the same as in example 1, but the reaction conditions were 40 ℃.
TEMPO functionalized MOFs material and AlH3According to the mass ratio of 1: 100, heating at 60 deg.C for 48 hr, and measuring modified AlH by draining method3Volume of hydrogen evolved.
Measuring AlH added with the functionalized modified MOFs material after heating for 72h in an air atmosphere at 60 ℃ by a drainage method3The volume of hydrogen released was 91 ml.
Example 3
In the same manner as in example 1, in the preparation method of the TEMPO functionalized MOFs material of this embodiment, H is added when TEMPO is grafted on the surface of the MOFs2The molar ratio of N-TEMPO to MOFs was also the same as in example 1, but the reaction conditions were 50 ℃.
TEMPO functionalized MOFs material and AlH3According to the mass ratio of 1: 100, heating at 60 deg.C for 48 hr, and measuring modified AlH by draining method3Volume of hydrogen evolved.
Measuring AlH added with the functionalized modified MOFs material after heating for 72h in an air atmosphere at 60 ℃ by a drainage method3The volume of hydrogen released was 94 ml.
Example 4
In the same manner as in example 1, in the preparation method of the TEMPO functionalized MOFs material of this embodiment, H is added when TEMPO is grafted on the surface of the MOFs2The molar weight ratio of N-TEMPO to MOFs was also the same as in example 1, except that TEMPO functionalized MOFs material was mixed with AlH3The mass ratio of the grinding and mixing is 1: 50.
TEMPO functionalized MOFs material and AlH3According to the mass ratio of 1: 50, fully grinding and uniformly mixing, then heating for 48 hours in an air atmosphere at 60 ℃, and measuring the modified AlH by using a drainage method3Volume of hydrogen evolved.
Measuring AlH added with the functionalized modified MOFs material after heating for 72h in an air atmosphere at 60 ℃ by a drainage method3The volume of hydrogen released was 89 ml.
Example 5
In the same manner as in example 1, in the preparation method of the TEMPO functionalized MOFs material of this embodiment, H is added when TEMPO is grafted on the surface of the MOFs2The molar weight ratio of N-TEMPO to MOFs was also the same as in example 1, except that TEMPO functionalized MOFs material was mixed with AlH3The mass ratio of the grinding and mixing is 1: 10.
TEMPO functionalized MOFs material and AlH3According to the mass ratio of 1: 50, fully grinding and uniformly mixing, then heating for 48 hours in an air atmosphere at 60 ℃, and measuring the modified AlH by using a drainage method3Volume of hydrogen evolved.
Measuring AlH added with the functionalized modified MOFs material after heating for 72h in an air atmosphere at 60 ℃ by a drainage method3The volume of hydrogen released was 98 ml.
Comparative example 1
The preparation method of MOFs material of the comparative example is the same as that of example 1, except that the MOFs material of the comparative example is not grafted with TEMPO radical scavenger and AlH3According to the mass ratio of 1: 100, and then subjected to the same procedure as in example 1 to test AlH3By liberation of hydrogenVolume.
Measuring AlH added with non-functionalized modified MOFs material after heating for 72h in 60 ℃ air atmosphere by using a drainage method3The volume of hydrogen released was 100 ml.
Comparative example 2
This comparative example uses AlH alone3For blank control, AlH was tested by the same procedure as in example 13Volume of hydrogen evolved.
AlH was measured by draining after heating at 60 ℃ for 72 hours in an air atmosphere3The volume of hydrogen released was 97 ml.
Experimental comparison of example 1, example 2 and example 3 shows that the prepared functionalized MOFs material is aligned to AlH at the functionalization temperature of 40 DEG C3The heat release hydrogen stability promotion effect is best. Experimental comparison of examples 1, 4 and 5 shows that when TEMPO is used to functionalize MOFs, AlH3When the mass ratio of (A) to (B) is 1%, the TEMPO functionalized MOFs material to AlH3The heat release hydrogen stability promotion effect is best. The experimental comparison of example 1, comparative example 1 and comparative example 2 shows that the TEMPO functionalized MOFs prepared in example 1 can convert AlH under the optimal conditions3The stability of the heat released hydrogen is improved by about 20 percent.
The foregoing description of specific embodiments of the present invention has been presented. It is to be understood that the present invention is not limited to the specific embodiments described above, and that various changes or modifications may be made by one skilled in the art within the scope of the appended claims without departing from the spirit of the invention. The embodiments and features of the embodiments of the present application may be combined with each other arbitrarily without conflict.
Claims (10)
1. Used for improving AlH3The stable functionalized MOFs material is characterized by comprising the following components: nanoscale metal organic framework material matrix UiO-66-NH2And a surface grafted TEMPO radical scavenger.
2. The method of claim 1 for lifting AlH3Stable functionalized MOFs material, characterized in that said gold is presentBelongs to an organic framework material matrix UiO-66-NH2Zirconium tetrachloride, 2-amino terephthalic acid and benzoic acid are mixed according to a molar ratio of 1: 1: 20 is dissolved in DMF solution and reacted at a predetermined temperature.
3. The method of claim 2 for lifting AlH3The stable functionalized MOFs material is characterized in that the metal organic framework material matrix UiO-66-NH2The predetermined reaction temperature in the preparation of (1) is 120 ℃, and the reaction time is 24 hours.
4. The method of claim 3 for lifting AlH3The stable functionalized MOFs material is characterized in that the method for functionalizing the surface of the functionalized MOFs material comprises the following steps: the metal organic framework material matrix UiO-66-NH is added2Reacting with diisocyanate to obtain active MOFs with end group of isocyanic acid radical; and then carrying out esterification reaction on the isocyanate and amino-substituted TEMPO to obtain the functionalized MOFs material.
5. Use according to any one of claims 1 to 4 for raising AlH3The preparation method of the stable functionalized MOFs material is characterized by comprising the following steps:
the metal organic framework material matrix UiO-66-NH is added2Dissolving the active MOFs and diisocyanate in an anhydrous DMF solution, and stirring to react for 6-8 h to obtain active MOFs with an end group of isocyanic acid radical;
and dissolving the active MOFs with the end group of isocyanic acid radical and amino-substituted TEMPO in an anhydrous DMF solution according to a specific molar ratio, and stirring for reaction for 12 hours to obtain the TEMPO functionalized MOFs material.
6. The process according to claim 5, wherein the molar ratio of active MOFs containing isocyanate groups to amino-substituted TEMPO is 1: 0.5 to 1.5.
7. The method according to claim 5, wherein the temperature of the stirring reaction is 30 to 50 ℃.
8. The method of claim 5, wherein the metal-organic framework material matrix UiO-66-NH2The preparation method comprises the following steps:
zirconium tetrachloride, 2-amino terephthalic acid and benzoic acid are mixed according to a molar ratio of 1: 1: 20 is dissolved in DMF solution, then the solution is put into a stainless steel hydrothermal reaction kettle to be uniformly mixed, and the mixture is reacted for 24 hours at the temperature of 120 ℃;
slowly cooling until the temperature is reduced to room temperature to obtain yellow powder, centrifugally cleaning the powder for 3-4 times by using a DMF (dimethyl formamide) solution, and removing unreacted ligands and metal ions;
soxhlet extracting with ethanol as extractant for three days, removing residual DMF solution to obtain solid powder;
drying and activating the obtained solid powder at 60 ℃ for 8 h.
9. Application of the functionalized MOFs material of any one of claims 1 to 4 to promote AlH3Method for stabilization, characterized in that the functionalized MOFs material and AlH are mixed3Mixing according to a specific proportion and grinding.
10. The method for applying according to claim 9, wherein said functionalized MOFs materials are reacted with AlH3The mass ratio of the mixture is 1 to 10 percent.
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| CN104624160A (en) * | 2015-01-21 | 2015-05-20 | 北京科技大学 | Preparation method of thermal conduction enhanced metal organic framework gas storage material |
| CN105175295A (en) * | 2015-09-24 | 2015-12-23 | 南昌航空大学 | Preparation for thiol-functionalization MOFs material and application thereof in adsorption and removal of heavy metal ions in water |
| CN109395698A (en) * | 2018-11-28 | 2019-03-01 | 大连理工大学 | A kind of preparation method using mixed ligand synthesis metal organic framework UiO-66 adsorbent |
| CN109569521A (en) * | 2018-12-10 | 2019-04-05 | 南昌航空大学 | A kind of rhodanine functionalization MOFs adsorbent and its preparation method and application |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104624160A (en) * | 2015-01-21 | 2015-05-20 | 北京科技大学 | Preparation method of thermal conduction enhanced metal organic framework gas storage material |
| CN105175295A (en) * | 2015-09-24 | 2015-12-23 | 南昌航空大学 | Preparation for thiol-functionalization MOFs material and application thereof in adsorption and removal of heavy metal ions in water |
| CN109395698A (en) * | 2018-11-28 | 2019-03-01 | 大连理工大学 | A kind of preparation method using mixed ligand synthesis metal organic framework UiO-66 adsorbent |
| CN109569521A (en) * | 2018-12-10 | 2019-04-05 | 南昌航空大学 | A kind of rhodanine functionalization MOFs adsorbent and its preparation method and application |
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