CN114163616A - Melamine functionalized porous organic polymer and preparation method and application thereof - Google Patents
Melamine functionalized porous organic polymer and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a melamine functional porous organic polymer, which is obtained by the cross-linking reaction of melamine and a ketone polymer precursor: firstly, dissolving terephthaloyl chloride and triptycene in dichloromethane, adding anhydrous ferric chloride to form a mixed solution, carrying out reflux reaction for 12 hours, cooling to room temperature, and washing and purifying the obtained precipitate to obtain a ketone-based polymer precursor; dissolving the melamine-functionalized porous organic polymer in dimethyl sulfoxide, adding melamine, uniformly mixing, carrying out reflux reaction for 72 hours, cooling to room temperature, washing, purifying and drying the obtained white precipitate to obtain the melamine-functionalized porous organic polymer. The invention adopts Melamine (MA) with rigid triazine ring as the post modifier, obtains the nitrogen-rich porous organic polymer through a two-step method, has the advantages of low cost of the required raw materials, environmental friendliness, large-scale replication and repeated use, simple synthesis method and wide application range, and provides technical reference for the research of preparing the nitrogen-rich porous material.
Description
Technical Field
The invention relates to an adsorption material, in particular to a melamine functionalized porous organic polymer, and also relates to a preparation method of the porous organic polymer and an application of the porous organic polymer as a radioactive iodine adsorbent.
Background
With the continuous development of industry, nuclear energy is widely used as a clean, sustainable and efficient energy source worldwide. However, nuclear power plants produce high-and low-grade radioactive wastes or used nuclear fuel, which, although not large in volume, have radioactive rays and therefore have serious consequences if not properly treated.
Radioactive iodine from nuclear fission (e.g. nuclear fission)129I and131I) is a radioactive isotope in nuclear waste. Wherein the content of the first and second substances,129the half-life of I is longer and is 1.57 multiplied by 107And (5) year. Therefore, prevention of such iodine contamination with high volatility and high mobility has become a problem to be solved.
Adsorption technology is considered to be a low cost and efficient contaminant removal process. To date, various inorganic porous materials (such as zeolites, hydrogels, activated carbon, and biochar), organic porous materials (such as Metal Organic Frameworks (MOFs), Porous Organic Polymers (POPs), and inorganic-organic hybrid materials), natural minerals, and biosorbents have been studied for iodine capture. Among them, Porous Organic Polymers (POPs) are Polymers with ultrahigh crosslinking properties designed and synthesized from Organic structural units, and have the following characteristics: (1) the covalent bond bonding has good chemical stability and thermal stability; (2) the material is composed of common light elements (C, O, B, N, Si), so the material has low density; (3) the material is generally amorphous in structure, with a graded pore size distribution, mainly micropores and mesopores formed by the mutual cross-linking of rigid monomers; (4) contains a large conjugated system and has a rigid structure. However, practical application of porous organic polymers constructed only from light elements such as carbon and hydrogen as iodine adsorbents still faces significant challenges.
Disclosure of Invention
The invention aims to provide a melamine functionalized porous organic polymer aiming at the defects in the prior art; the invention also provides a preparation method of the porous organic polymer and application of the porous organic polymer in efficiently adsorbing radioactive iodine.
In order to achieve the purpose, the invention can adopt the following technical scheme:
the melamine functional porous organic polymer is obtained by taking melamine as a functional modifier and carrying out a crosslinking reaction with a chain ketone-based polymer precursor, and has the following structure:
a method for preparing a melamine functionalized porous organic polymer comprising the steps of:
dissolving terephthaloyl chloride and triptycene in a dichloromethane solvent, adding an anhydrous ferric chloride catalyst in a low-temperature environment to form a mixed solution, carrying out reflux reaction for 12 hours at 70 ℃ under the protection of nitrogen, cooling to room temperature, washing obtained white precipitates by using dichloromethane, methanol and water in sequence, purifying the obtained white precipitates by using a mixed solution of water and methanol for 24 hours, and carrying out vacuum drying on obtained white products for 12 hours at 60 ℃, thus obtaining a ketone-based polymer precursor;
secondly, dissolving the obtained ketone-based polymer precursor in dimethyl sulfoxide, adding melamine, uniformly mixing, carrying out reflux reaction at 160 ℃ for 72 hours under the protection of nitrogen, cooling to room temperature, washing the obtained white precipitate with dimethyl sulfoxide, methanol and water in sequence, and purifying with a mixed solution of water and methanol for 24 hours; and (3) drying the obtained white product at 60 ℃ for 12 hours in vacuum to obtain the melamine functionalized porous organic polymer.
Preferably, the molar ratio of terephthaloyl chloride to anhydrous ferric chloride as the catalyst used in the first step of the process of the present application is 2:3: 6.
Preferably, the low-temperature environment is 20 ℃ when the anhydrous ferric chloride catalyst is added in the first step of the preparation method.
Preferably, the mass ratio of the ketone-based polymer precursor to melamine used in the second step of the process of the present application is 1: 6.
Preferably, the volume ratio of water to methanol used for purifying the white precipitate in the first and second steps of the preparation method of the present application is 1: 1.
The melamine functional porous organic polymer prepared by the invention is used as a radioactive iodine adsorbent.
The invention has the advantages that the Melamine (MA) with rigid triazine ring is used as the post modifier, the nitrogen-rich porous organic polymer is obtained by a two-step method, the cost of the required raw materials is low, the advantages of environmental protection, large-scale replication and repeated use are achieved, the synthetic method is simple, the application range is wide, and the technical reference is provided for the research of preparing the nitrogen-rich porous material; the synthesized porous organic polymer has high specific surface area and rich nitrogen content. Experiments prove that the nitrogen-rich porous organic polymer material prepared by the invention has high adsorption capacity on iodine vapor and iodine/cyclohexane solution, can be recycled, and has practical application value for the nuclear waste problem which may face in the future.
Drawings
FIG. 1 is a schematic diagram of a synthetic route of a melamine functionalized porous organic polymer in example 1 of the present invention.
FIG. 2 is an infrared spectrum of a melamine functionalized porous organic polymer and monomers thereof in example 1.
FIG. 3 is a scanning electron micrograph of the melamine functionalized porous organic polymer of example 1.
FIG. 4 is a transmission electron micrograph of a melamine functionalized porous organic polymer in example 1.
FIG. 5 is an X-ray diffraction pattern of the melamine functionalized porous organic polymer of example 1.
FIG. 6 is a thermogravimetric analysis of the melamine functionalized porous organic polymer in example 1.
FIG. 7 is a nitrogen adsorption desorption isotherm of the melamine functionalized porous organic polymer of example 1.
FIG. 8 is a graph showing the pore size distribution of the melamine functionalized porous organic polymer in example 1.
FIG. 9 is a graph showing the adsorption curve of the melamine functionalized porous organic polymer to iodine vapor in example 1.
FIG. 10 is a graph showing the adsorption equilibrium of the melamine functionalized porous organic polymer in example 1 for iodine in cyclohexane.
FIG. 11 is a test of the recycling of iodine vapor by the melamine functionalized porous organic polymer of example 1.
Detailed Description
The present invention is further described below in conjunction with specific embodiments to facilitate understanding and application by those skilled in the art.
EXAMPLE 1 preparation of a Melamine-functionalized porous organic Polymer
1. Raw materials
Triptycene: shanghai Michelin Biochemical technology Limited, purity 99%;
terephthaloyl chloride: shanghai Michelin Biochemical technology Limited, purity 99%;
melamine: shanghai Michelin Biochemical technology Limited, purity 99%;
anhydrous ferric chloride: shanghai Michelin Biochemical technology Limited, purity 99%;
dichloromethane: the product of Tianjin Kemi European chemical reagent company, analytically pure;
methanol: the product of Tianjin Kemi European chemical reagent company, analytically pure;
dimethyl sulfoxide: the product of Tianjin Kemi European chemical reagent company, analytically pure;
water: the ultrapure water was purified by a Milli-Q purification apparatus (Millipore, USA) and the resistivity was 18.2 M.OMEGA.cm.
2. Reaction vessel and apparatus
Round bottom flask: 250mL and 100 mL;
and (3) vacuum drying oven: DZF-6050, a Hengchang scientific apparatus, Shanghai.
3. Preparation method
The method for preparing the melamine functionalized porous organic polymer comprises the following steps:
first, 0.609g of terephthaloyl chloride and 0.509g of triptycene are added to a 250mL round bottom flask containing 100mL of dichloromethane, the solution is maintained at 20 ℃, and then 0.973g of anhydrous ferric chloride is slowly added; then stirring the solution under the protection of nitrogen and carrying out reflux reaction for 12 hours at the temperature of 70 ℃; after the reaction is finished and cooled to room temperature, filtering to obtain white precipitates, respectively and thoroughly washing with dichloromethane, methanol and water (three times), further purifying with a water and methanol mixed solution with a volume ratio of 1:1 in a Soxhlet extractor for 24 hours to remove catalyst anhydrous ferric chloride, and finally vacuum-drying in a vacuum drying oven at 60 ℃ for 12 hours to obtain a ketone-based polymer precursor (TPC-TC) (white product);
secondly, dispersing 0.20g and 1.2g of the obtained ketone-based polymer precursor into a 100mL round-bottom flask containing 50mL of dimethyl sulfoxide, uniformly mixing, stirring under the protection of nitrogen, and carrying out reflux reaction at 160 ℃ for 72 hours; after the reaction is finished and the temperature is cooled to room temperature, the white precipitate obtained by filtering is respectively and thoroughly washed by dimethyl sulfoxide, methanol and water (three times), and then the mixture solution of water and methanol with the volume ratio of 1:1 is further purified for 24 hours in a Soxhlet extractor; and finally, putting the mixture into a vacuum drying oven to be dried for 12 hours in vacuum at the temperature of 60 ℃ to obtain the melamine functionalized porous organic polymer (TPC-TC-MA). The synthetic route is shown in figure 1.
Example 2 characterization of the porous organic Polymer (TPC-TC-MA) prepared in example 1 of the invention
1. Infrared spectrum analysis: the TPC-TC-MA prepared in example 1 and the corresponding monomer were characterized by Fourier transform infrared spectroscopy, the Fourier infrared spectrum of which is shown in FIG. 2, from which it can be seen that: TPC-TC 1657 cm-1Has a C = O expansion and contraction vibration absorption peakIt is shown that the TPC-TC, a ketone-based polymer precursor, was successfully acylated by Friedel-Crafts. And 1558 cm-1And 1350 cm-1The bands at (a) were attributed to the C = N and C-N stretching vibrations of the triazine ring, respectively, indicating successful crosslinking of melamine with the ketone-based polymer precursor.
2. Scanning electron microscope analysis: when the TPC-TC-MA prepared in example 1 is observed by a scanning electron microscope, the synthesized material is shown in FIG. 3 to have an irregular granular aggregation structure.
3. Transmission electron microscopy analysis: the TPC-TC-MA prepared in example 1 is observed by a transmission electron microscope, and the result is shown in FIG. 4, and the channel disorder of the synthesized material can be seen.
4. Analysis of crystal type: the crystal type of TPC-TC-MA prepared in example 1 was characterized by X-ray diffractometry (XRD), and its XRD pattern is shown in fig. 5, and it can be seen from fig. 5 that the prepared material exhibits amorphous characteristics.
5. Thermogravimetric analysis: the TPC-TC-MA prepared in example 1 was subjected to thermogravimetric analysis under an argon atmosphere at 5 deg.C/min, and the thermogravimetric curve is shown in FIG. 6. As can be seen, these polymers begin to decompose substantially at 350 ℃ in the backbone, indicating that the polymers have very good thermal stability. Meanwhile, the polymer is proved to have very good chemical stability by finding that the sample can not be dissolved or decomposed in common organic solvents (methanol, ethanol, dichloromethane, chloroform, tetrahydrofuran, acetone, N' -dimethylformamide and the like).
5. Nitrogen adsorption desorption analysis: the TPC-TC-MA prepared in example 1 was subjected to a nitrogen adsorption-desorption isotherm curve test, and as a result, as shown in FIG. 7, the BET specific surface area of the prepared polymer was 584 m2/g。
7. Pore size distribution: the calculation of the pore size distribution of the TPC-TC-MA prepared in example 1 was performed according to the non-local density functional theory method, and it can be seen from FIG. 8 that the prepared material has abundant micropores.
Example 3 adsorption of iodine molecules by porous organic Polymer (TPC-TC-MA) prepared in example 1 of the present invention
1. Adsorption of gaseous iodine by TPC-TC-MA
Putting 10 mg of melamine functionalized porous organic polymer (TPC-TC-MA) into an open small bottle, putting the small bottle into a glass small bottle containing 1.0 g of iodine simple substance, sealing the glass small bottle, and then putting the sealed glass small bottle into a 75 ℃ oven for keeping for a period of time; weighing at different intervals, and calculating the adsorption capacity of the material to iodine; as shown in FIG. 9, the material prepared by the present application has a very high adsorption capacity for iodine, up to 254.1 wt%.
2. Adsorption of TPC-TC-MA to iodine in cyclohexane solution
10 mg of adsorbent was dispersed in 10 mL of iodine/cyclohexane solutions of different concentrations (100, 200, 300, 400, 500, 600 mg/L) and adsorbed by shaking at room temperature for 2 hours. As can be seen from FIG. 10, the adsorption conformed to Langmuir and Frundlich models, and the highest adsorption capacity of TPC-TC-MA was 380.2 mg/g.
3. Repeated utilization test
The repeated utilization rate of the melamine functional porous organic polymer TPC-TC-MA prepared in example 1 is examined: and washing the material adsorbed with the iodine vapor for multiple times by using a methanol solution to remove iodine molecules in the pore channels, drying the material, and then using the dried material for the next round of adsorption of the iodine vapor. As can be seen from fig. 11, after five times of recycling, the material prepared in example 1 still has a high adsorption performance on iodine vapor, which proves that the material can be recycled, and has a good application prospect in treatment of radioactive iodine in nuclear waste.
Claims (7)
1. A melamine functionalized porous organic polymer characterized by: the melamine-modified ketone-based polymer is obtained by using melamine as a functional modifier and performing crosslinking reaction with a chain-like ketone-based polymer precursor, and has the following structure:
2. a method for preparing a melamine functionalized porous organic polymer, characterized by: the method comprises the following steps:
dissolving terephthaloyl chloride and triptycene in a dichloromethane solvent, adding an anhydrous ferric chloride catalyst in a low-temperature environment to form a mixed solution, carrying out reflux reaction for 12 hours at 70 ℃ under the protection of nitrogen, cooling to room temperature, washing obtained white precipitates by using dichloromethane, methanol and water in sequence, purifying the obtained white precipitates by using a mixed solution of water and methanol for 24 hours, and carrying out vacuum drying on obtained white products for 12 hours at 60 ℃, thus obtaining a ketone-based polymer precursor;
secondly, dissolving the obtained ketone-based polymer precursor in dimethyl sulfoxide, adding melamine, uniformly mixing, carrying out reflux reaction at 160 ℃ for 72 hours under the protection of nitrogen, cooling to room temperature, washing the obtained white precipitate with dimethyl sulfoxide, methanol and water in sequence, and purifying with a mixed solution of water and methanol for 24 hours; and (3) drying the obtained white product at 60 ℃ for 12 hours in vacuum to obtain the melamine functionalized porous organic polymer.
3. The method of preparing a melamine functionalized porous organic polymer according to claim 2, wherein: the molar ratio of the triptycene to the terephthaloyl chloride to the catalyst anhydrous ferric chloride used in the first step is 2:3: 6.
4. The method of preparing a melamine functionalized porous organic polymer according to claim 2, wherein: the low temperature environment when anhydrous ferric chloride catalyst is added in the first step is 20 ℃.
5. The method of preparing a melamine functionalized porous organic polymer according to claim 2, wherein: the mass ratio of the ketone-based polymer precursor to melamine in the second step was 1: 6.
6. The method of preparing a melamine functionalized porous organic polymer according to claim 2, wherein: the volume ratio of water to methanol used for purifying the white precipitate in the first step and the second step is 1: 1.
7. Use of a melamine functionalized porous organic polymer as a radioiodine adsorbent.
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| CN117069919A (en) * | 2023-08-17 | 2023-11-17 | 湖北大学 | Organic porous adsorption material based on pentapterine quinone for blood purification and preparation method thereof |
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|---|---|---|---|---|
| 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 |
| CN117069919A (en) * | 2023-08-17 | 2023-11-17 | 湖北大学 | Organic porous adsorption material based on pentapterine quinone for blood purification and preparation method thereof |
| CN117069919B (en) * | 2023-08-17 | 2024-02-09 | 湖北大学 | Organic porous adsorption material based on pentapterine quinone for blood purification and preparation method thereof |
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