CN113683740A - Halogen ion functionalized organic porous material and preparation method and application thereof - Google Patents
Halogen ion functionalized organic porous material and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a halogen ion functionalized organic porous material, a preparation method and application thereof, and belongs to the technical field of porous organic material polymers. The invention firstly utilizes 5,5 '-diamino-2, 2' -bipyridyl and 2,4, 6-trihydroxy-1, 3, 5-benzenetricarboxylic aldehyde to react to obtain an organic porous material, and then the organic porous material is ionized and modified to obtain a halogen ion functionalized organic porous material.
Description
Technical Field
The invention belongs to the technical field of porous organic material polymers, and particularly relates to preparation of a halogen ion type porous material and application of the halogen ion type porous material in efficient adsorption of radioactive iodine
Background
Radioactive iodine is one of main harmful radioactive pollutants in nuclear waste treatment and nuclear accidents, has long half-life cycle, is easy to volatilize and fast to diffuse, and seriously threatens environmental safety and human health. Porous Organic Polymers (POPs) are a new class of Porous materials formed by covalent bonding using light elements such as C, H, O, N. The material has the advantages of high specific surface area, permanently adjustable porosity, controllable structure, high thermochemistry property, potential of post-synthesis modification and the like, and is widely concerned by researchers.
Currently, adsorption is the most commonly used radioiodination method. Commonly used adsorbents are mainly organic amine impregnated activated carbon, silver functionalized porous materials such as molecular sieves, silica gel, clay, etc. These materials have poor adsorption capacity due to low specific surface area, and silver-based adsorbents have problems of high cost, poor cyclability, and the like; recently, metal organic framework Materials (MOFs) and porous organic polymer materials (POPs) have also been used for adsorption of radioactive iodine. Despite their high specific surface area, these materials typically have high adsorption capacities at < 80 ℃ and high concentrations of iodine vapor (> 10000ppmv) due to their lack of strong adsorption sites, while the adsorption capacities at commercial use conditions (150 ℃ and 150ppmv) are typically poor, and thus the current commercial requirements are still not met by the existing adsorbents.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a method for efficiently adsorbing radioactive iodine under industrial application conditions (150 ℃, 150ppmv), and solves the problems of high energy consumption, high cost, complex material synthesis process and poor cyclability of the existing radioactive iodine adsorption technology by preparing a halogen ion type porous material.
In order to achieve the purpose, the invention adopts the technical scheme that:
a halogen ion functionalized organic porous material has a molecular formula structure as follows:
in the structural formula, X–Represents Br–Or I–The BET specific surface area of the material was 581m2g-1And 387m2g-1。
The preparation method of the halogen ion functionalized organic porous material is prepared by taking the following organic ligands as raw materials under the conditions of normal temperature and normal pressure; the synthesized organic porous material comprises but is not limited to one of imide, polyimide, hydrazone or borate; the catalyst used includes but is not limited to acetic acid or pyridine base capable of synthesizing organic porous materials; the solvent used includes water and common organic solvents including but not limited to one of chlorobenzene, N-dimethylacetamide, methanol, dioxane, acetonitrile, ethanol; the template agent is a common aromatic or hydrocarbon compound, and the common aromatic or hydrocarbon compound comprises but is not limited to one of mesitylene, o-dichlorobenzene, 1,2, 4-trichlorobenzene or dioxane; post-modification methods of the materials used include, but are not limited to, solvothermal, milling, or sonication; post-modification raw materials used include, but are not limited to, 1, 2-dibromotetrafluoroethane, 1, 2-dibromoethane, or 2, 3-dibromo 2, 3-dimethylbutane.
Furthermore, 2,4, 6-trihydroxy-1, 3, 5-benzene triformal and 5,5 '-diamino-2, 2' -bipyridyl are selected as raw materials for the organic porous material, and the molar ratio of the 2,4, 6-trihydroxy-1, 3, 5-benzene triformal to the 5,5 '-diamino-2, 2' -bipyridyl is 1: 1.5-2.
Further, the solvent is dioxane; the template agent is mesitylene; the catalyst is acetic acid; the ratio of the solvent to the catalyst is 3-10: 3-10: 1.
furthermore, a solvothermal method is selected as the post-modification method; the selected solvent is acetonitrile or ethanol, wherein the addition amount of the solvent is calculated according to the total mass of the synthesized organic porous material, and the mass fraction of the solid powder in the solvent is 0.1-20 wt%.
Further, 1, 2-dibromotetrafluoroethane is selected as a post-modification organic raw material, wherein the addition amount of the organic raw material is calculated according to the total molar weight of the organic raw material and the synthesized organic porous material, and the molar ratio of the organic raw material to the synthesized organic porous material is 1-20: 1; the post-modification temperature is 0-100 ℃, and the reaction time is 0.5-8 d.
The halogen ion functionalized organic porous material is used for adsorbing iodine.
Further, the concentration of iodine vapor at the time of adsorption was 150ppmv, and the temperature of adsorption was 150 ℃.
Further, the iodine adsorption time is 15-50 h.
The organic porous material after adsorbing iodine is reused after desorbing iodine, and the conditions for desorbing iodine are as follows: under the condition of room temperature, the organic porous material after iodine adsorption is prepared by the following steps of using a volume ratio of 1:1, stirring and washing a saturated potassium iodide solution prepared from ethanol and water for multiple times, then washing the solution with ultrapure water for multiple times, and performing suction filtration to obtain a solid powder product, and drying the solid powder product for 12 hours in a vacuum drying oven at the temperature of 50-120 ℃.
Compared with the prior art, the invention has the following characteristics:
the invention discloses a method for efficiently adsorbing low-concentration radioactive iodine by using a halogen ion type porous material under a high-temperature condition. Compared with the reported radioactive iodine adsorption material, the newly synthesized halogen ion functionalized organic porous material has the advantages of simple synthesis method, strong thermal stability, high adsorption performance to radioactive iodine vapor, good cyclicity and the like.
Drawings
FIG. 1 is a PXRD pattern of the organic porous material prepared by the present invention;
FIG. 2 is a PXRD pattern for preparing a halogen ion functionalized organic porous material according to the present invention;
FIG. 3 is an infrared spectrum of the present invention for preparing an organic porous material and a halogen ion functionalized organic porous material;
FIG. 4 is a thermogram of the present invention for preparing an organic porous material;
FIG. 5 is a scanning electron microscope image of the organic porous material prepared by the present invention;
FIG. 6 is a scanning electron microscope image of the halogen ion functionalized organic porous material prepared by the present invention;
FIG. 7 is a nitrogen adsorption/desorption graph of the halogen ion functionalized organic porous material prepared by the present invention;
FIG. 8 is a graph showing the adsorption profile of radioactive iodine vapor with time for the preparation of a halogen ion functionalized organic porous material according to the present invention;
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more clear, the present invention is further described in detail below with reference to embodiments.
The synthetic route of the halogen ion functionalized organic porous material is as follows:
example 1, preparation of porous organic material:
s1, 0.1 mmol of 2,4, 6-trihydroxy-1, 3, 5-benzenetricarboxylic acid and 0.15 mmol of 5,5 '-diamino-2, 2' -bipyridine were added to o.d. × i.d. ═ 9.5 × 7.5mm2In the glass tube
S2, adding dioxane, mesitylene and 6M acetic acid into the sample tube in sequence, wherein the volume ratio is 5: 5: 1;
s3, carrying out decompression freezing and sealing on the heat-resistant glass tube in liquid nitrogen, and reacting for 5d in an oven at 120 ℃ to obtain orange organic porous solid powder;
s4, washing the organic porous material powder with anhydrous tetrahydrofuran for 2d by a Soxhlet extraction method, removing residual organic solvent, and drying in a vacuum oven at 80-100 ℃ for 10-18 h to obtain the organic porous material TpBpy with the yield of 70%.
Fig. 1 is a PXRD pattern corresponding to this example, and it can be seen from the figure that the main characteristic peak observed at 2 θ ═ 3.6 is consistent with the characteristic peak position reported in the known literature, indicating that the organic porous material we obtained by this method is correct.
Fig. 4 is a thermogravimetric diagram corresponding to the example, and it can be seen from the graph that the organic porous material is stable at about 215 ℃ and starts to decompose.
FIG. 5 is a scanning electron microscope atlas corresponding to the embodiment, and it can be seen from the figure that the material has a uniform morphology and a stable structure.
B1：
s1, adding 0.5 mmol of porous material, 5 mmol of 1, 2-dibromo-1, 1,2, 2-tetrafluoroethane and 70mL of acetonitrile into a 150mL high-temperature pressure-resistant bottle, reacting for 24h at 90 ℃, then additionally adding 5 mmol of 1, 2-dibromo-1, 1,2, 2-tetrafluoroethane, and reacting for further 24h at 90 ℃;
and S2, cooling to room temperature, performing suction filtration, washing a filter cake by using ethanol for a few times to remove unreacted 1, 2-dibromo-1, 1,2, 2-tetrafluoroethane, and drying in a vacuum drying oven at the temperature of 80-100 ℃ for 10-24 h to obtain the bromide ion type porous material.
B2：
S1, adding 0.5 mmol of bromide ion type porous material into a saturated potassium iodide solution, violently stirring at normal temperature for 3 hours, carrying out suction filtration, and washing a filter cake with water to remove redundant potassium iodide salt; adding the filter cake into saturated potassium iodide solution, stirring vigorously for 3h at normal temperature, filtering, and repeating the above steps for 2 times;
s2, washing the product with water and ethanol in sequence, and then putting the product into a vacuum drying oven at 80-100 ℃ to dry for 10-24 h to obtain the iodonium type porous material TpBpy-4F.
Fig. 2 is a PXRD pattern corresponding to this example, and it can be seen from the pattern that a main characteristic peak is observed at 2 θ ═ 3.6, which indicates that the halogen ion functionalized covalent organic framework material prepared by the post-modification method of the organic porous material has a stable crystal form and a stable configuration.
FIG. 3 is an IR spectrum corresponding to this example, as can be seen at 1233cm-1The TpBpy-4F has more C-N pyridine peaks, which indicates that pyridine salt is formed; as can be seen from the figure, the infrared peak position after post-modification is from 827cm-1、987cm-1Is shifted to 831cm-1And 997cm-1All show that the organic porous material is successfully prepared.
FIG. 6 is a scanning electron microscope atlas corresponding to the embodiment, and it can be seen from the atlas that the post-modified organic porous material has uniform morphology and stable structure
FIG. 7 is a nitrogen adsorption/desorption graph corresponding to this example, from which it can be seen that the BET specific surface area of the TpBpy-4F-KI material is 387m2g-1Microporous materials with a predominant pore size distribution at 1.17 nm.
Example 3 preparation of a halogen ion functionalized organic porous material for iodine adsorption:
s1, placing the halogen ion functionalized organic porous material powder sample into a thermal weight machine, activating for 4 hours at 150 ℃, and recording the weight;
s2, then introducing iodine vapor with the concentration of 150ppmv and containing nitrogen at the temperature of 150 ℃;
and S3, recording the weight of the sample in the adsorption process, and researching the adsorption performance of the sample on the iodine vapor by using a gravimetric method.
FIG. 8 is a graph showing the adsorption of iodine vapor over time for this example, from which it can be seen that the halogen ion functionalized organic porous material adsorbed 36.5 wt% iodine at 150 ℃ and an iodine vapor concentration of 150 ppmv;
example 4 (preparation of Ionic porous Material for iodine Desorption experiment)
S1, under the condition of room temperature, the sample TpBpy-4F-I enriched with iodine2Placing the mixture in a saturated potassium iodide solution prepared by ethanol and water (the volume ratio is 1: 1);
s2, stirring for half an hour, filtering, washing a filter cake by using a mixed solution of ethanol and water (the volume ratio is 1: 1), and removing adsorbed iodine;
s3, repeating the operation of the step S2 for 3 times, and then washing the sample for 3 times by using ultrapure water to remove redundant potassium iodide;
s4, drying the sample in a dynamic vacuum oven at 100 ℃ for 10h to obtain a purified sample TpBpy-4F;
s5, 5 times of radioactive iodine adsorption circulationAfter the loop, TpBpy-4F-I2Still can keep the excellent iodine adsorption performance.
Claims (10)
1. The halogen ion functionalized organic porous material is characterized in that the molecular formula structure of the organic porous material is as follows:
in the structural formula, X–Represents Br–Or I–The BET specific surface area of the material was 581m2g-1And 387m2g-1。
2. The preparation method of the halogen ion functionalized organic porous material according to claim 1, which is characterized by being prepared by taking the following organic ligands as raw materials under the conditions of normal temperature and normal pressure; the synthesized organic porous material comprises but is not limited to one of imide, polyimide, hydrazone or borate; the catalyst used includes but is not limited to acetic acid or pyridine base capable of synthesizing organic porous materials; the solvent used includes water and common organic solvents including but not limited to one of chlorobenzene, N-dimethylacetamide, methanol, dioxane, acetonitrile, ethanol; the template agent is a common aromatic or hydrocarbon compound, and the common aromatic or hydrocarbon compound comprises but is not limited to one of mesitylene, o-dichlorobenzene, 1,2, 4-trichlorobenzene or dioxane; post-modification methods of the materials used include, but are not limited to, solvothermal, milling, or sonication; post-modification raw materials used include, but are not limited to, 1, 2-dibromotetrafluoroethane, 1, 2-dibromoethane, or 2, 3-dibromo 2, 3-dimethylbutane.
3. The method for preparing the halogen ion functionalized organic porous material according to claim 2, characterized in that the raw materials used for the organic porous material are 2,4, 6-trihydroxy-1, 3, 5-benzenetricarboxylic aldehyde and 5,5 '-diamino-2, 2' -bipyridine, and the molar ratio of the 2,4, 6-trihydroxy-1, 3, 5-benzenetricarboxylic aldehyde to the 5,5 '-diamino-2, 2' -bipyridine is 1: 1.5-2.
4. The method for preparing the halogen ion functionalized organic porous material according to claim 2, wherein the solvent is selected from dioxane; the template agent is mesitylene; the catalyst is acetic acid; the ratio of the solvent to the catalyst is 3-10: 3-10: 1.
5. the method for preparing the halogen ion functionalized organic porous material according to claim 2, wherein the post-modification method is a solvothermal method; the selected solvent is acetonitrile or ethanol, wherein the addition amount of the solvent is calculated according to the total mass of the synthesized organic porous material, and the mass fraction of the solid powder in the solvent is 0.1-20 wt%.
6. The preparation method of the halogen ion functionalized organic porous material according to claim 5, wherein the selected post-modification organic raw material is 1, 2-dibromotetrafluoroethane, wherein the addition amount of the organic raw material is calculated according to the total molar amount of the organic raw material and the synthesized organic porous material, and the molar ratio of the organic raw material to the synthesized organic porous material is 1-20: 1; the post-modification temperature is 0-100 ℃, and the reaction time is 0.5-8 d.
7. Use of a halogen ion functionalized organic porous material according to claim 1 for the adsorption of iodine.
8. Use of a halogen ion functionalised organic porous material according to claim 7, characterized in that the concentration of iodine vapour at adsorption is 150ppmv and the temperature of adsorption is 150 ℃.
9. The use of the halogen ion functionalized organic porous material according to claim 7, characterized in that the iodine adsorption time is 15h to 50 h.
10. The use of the halogen ion functionalized organic porous material according to claim 7, wherein the organic porous material after adsorbing iodine is reused after desorbing iodine under the following conditions: under the condition of room temperature, the organic porous material after iodine adsorption is prepared by the following steps of using a volume ratio of 1:1, stirring and washing a saturated potassium iodide solution prepared from ethanol and water for multiple times, then washing the solution with ultrapure water for multiple times, and performing suction filtration to obtain a solid powder product, and drying the solid powder product for 12 hours in a vacuum drying oven at the temperature of 50-120 ℃.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114456337A (en) * | 2022-02-16 | 2022-05-10 | 南开大学 | Preparation method of ionic porous organic cage material applied to radioactive iodine adsorption under high-temperature and low-concentration conditions |
| CN115254061A (en) * | 2022-08-15 | 2022-11-01 | 齐齐哈尔大学 | Preparation method of ultrahigh cross-linked porous organic polymer iodine adsorbent |
| CN115960326A (en) * | 2023-01-19 | 2023-04-14 | 大连理工大学 | For CO 2 Ionic covalent organic framework catalyst for preparing cyclic carbonate through cycloaddition, preparation method and application |
| CN116239779A (en) * | 2022-09-06 | 2023-06-09 | 武汉大学 | Two-dimensional halogen bond organic framework material for iodination reagent, preparation method and application thereof |
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| CN109180957A (en) * | 2018-08-29 | 2019-01-11 | 复旦大学 | Radical cation type covalent organic frame material and its preparation method and application |
| CN109705049A (en) * | 2018-12-29 | 2019-05-03 | 青岛科技大学 | A kind of preparation method and purposes of the schiff bases cyclic compound applied to the absorption of efficient iodine |
| CN112156758A (en) * | 2020-09-15 | 2021-01-01 | 清华大学 | Porous material and preparation method and application thereof |
| CN113024828A (en) * | 2021-03-09 | 2021-06-25 | 南开大学 | Method for preparing covalent organic framework material by utilizing high-pressure homogenization |
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| CN109180957A (en) * | 2018-08-29 | 2019-01-11 | 复旦大学 | Radical cation type covalent organic frame material and its preparation method and application |
| CN109705049A (en) * | 2018-12-29 | 2019-05-03 | 青岛科技大学 | A kind of preparation method and purposes of the schiff bases cyclic compound applied to the absorption of efficient iodine |
| CN112156758A (en) * | 2020-09-15 | 2021-01-01 | 清华大学 | Porous material and preparation method and application thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114456337A (en) * | 2022-02-16 | 2022-05-10 | 南开大学 | Preparation method of ionic porous organic cage material applied to radioactive iodine adsorption under high-temperature and low-concentration conditions |
| CN114456337B (en) * | 2022-02-16 | 2023-11-03 | 南开大学 | Preparation method of ionic porous organic cage material applied to radioactive iodine adsorption under high-temperature and low-concentration conditions |
| CN115254061A (en) * | 2022-08-15 | 2022-11-01 | 齐齐哈尔大学 | Preparation method of ultrahigh cross-linked porous organic polymer iodine adsorbent |
| CN116239779A (en) * | 2022-09-06 | 2023-06-09 | 武汉大学 | Two-dimensional halogen bond organic framework material for iodination reagent, preparation method and application thereof |
| CN115960326A (en) * | 2023-01-19 | 2023-04-14 | 大连理工大学 | For CO 2 Ionic covalent organic framework catalyst for preparing cyclic carbonate through cycloaddition, preparation method and application |
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