CN114163616B - 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 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, and obtaining the melamine functionalized porous organic polymer. The invention adopts Melamine (MA) with rigid triazine ring as a post-modifier, obtains the nitrogen-rich porous organic polymer through a two-step method, has the advantages of low cost of required raw materials, environmental friendliness, capability of being copied and reused in a large quantity, 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 application of the porous organic polymer as a radioactive iodine adsorbent.
Background
With the continuous development of industry, nuclear energy is widely used worldwide as a clean, sustainable and efficient energy source. However, the nuclear power plant generates high and low-order radioactive waste or used nuclear fuel, and the nuclear power plant occupies a small volume, but has serious consequences if mishandled due to radioactive rays.
Radioactive iodine generated by nuclear fission (e.g 129 I and 131 i) Is a radioisotope in nuclear waste. Wherein, the liquid crystal display device comprises a liquid crystal display device, 129 i has a longer half-life of 1.7X10 7 Year after year. Therefore, prevention of such iodine pollution having 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 zeolite, hydrogel, 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 biological adsorbents have been studied for iodine capture. Wherein, the porous organic polymer (Porous Organic Polymers, POPs) is a polymer with ultrahigh crosslinking property designed and synthesized by organic structural units, and has the following characteristics: (1) The covalent bond has good chemical stability and thermal stability; (2) The constituent elements of the material are common light elements (C, O, B, N, si), so the density of the material is low; (3) The material is generally amorphous in structure with a graded pore size distribution, primarily micropores and mesopores formed by cross-linking of rigid monomers; (4) comprising a large conjugated system, having a rigid structure. However, the practical use of porous organic polymers built with only light elements such as carbon and hydrogen as iodine adsorbents still presents a significant challenge.
Disclosure of Invention
The invention aims at overcoming the defects existing in the prior art and providing a melamine functionalized porous organic polymer; the invention also provides a preparation method of the porous organic polymer and application of the porous organic polymer in the aspect of efficiently adsorbing radioactive iodine.
In order to achieve the above purpose, the present invention may adopt the following technical scheme:
the melamine functional porous organic polymer is obtained by taking melamine as a functional modifier and performing a crosslinking reaction with a chain-shaped ketone-based polymer precursor, and has the following structure:
a process 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 at 70 ℃ for 12 hours under the protection of nitrogen, cooling to room temperature, washing an obtained white precipitate with dichloromethane, methanol and water in sequence, purifying for 24 hours with the mixed solution of water and methanol, and vacuum-drying the obtained white product at 60 ℃ for 12 hours to obtain a ketone-based polymer precursor;
secondly, dissolving the obtained ketone-based polymer precursor in dimethyl sulfoxide, adding melamine, carrying out reflux reaction for 72 hours at 160 ℃ under the protection of nitrogen after uniform mixing, cooling to room temperature, washing the obtained white precipitate with dimethyl sulfoxide, methanol and water in sequence, and purifying for 24 hours with a mixed solution of water and methanol; the white product obtained was dried in vacuo at 60 ℃ for 12 hours to give a melamine functionalized porous organic polymer.
Preferably, the molar ratio of terephthaloyl chloride to anhydrous ferric chloride 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 preparation process of the present application is 1:6.
Preferably, the volume ratio of water to methanol used in the first and second steps of purification of the white precipitate in the preparation process 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 preparation method has the advantages that Melamine (MA) with a rigid triazine ring is adopted as a post-modifier, the nitrogen-rich porous organic polymer is obtained through a two-step method, the cost of the required raw materials is low, the preparation method has the advantages of environmental friendliness and capability of being copied and reused in a large amount, and the synthesis method is simple and wide in application range, so that technical reference is provided for the research of preparing the nitrogen-rich porous material; the porous organic polymer obtained by synthesis has higher 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 to iodine vapor and iodine/cyclohexane solution, can be recycled, and has practical application value to nuclear waste problems possibly faced in future.
Drawings
FIG. 1 is a schematic representation of the synthetic route to the melamine functionalized porous organic polymer of example 1 of the present invention.
FIG. 2 is an infrared spectrum of the melamine functionalized porous organic polymer and its preparation monomer in example 1.
FIG. 3 is a scanning electron microscope image of the melamine functionalized porous organic polymer of example 1.
FIG. 4 is a transmission electron microscopy image of the melamine functionalized porous organic polymer of 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 of example 1.
Fig. 7 is a nitrogen adsorption desorption isotherm of the melamine functionalized porous organic polymer in example 1.
FIG. 8 is a pore size distribution plot of the melamine functionalized porous organic polymer of example 1.
Fig. 9 is an adsorption curve of iodine vapor by the melamine functionalized porous organic polymer of example 1.
FIG. 10 is an adsorption equilibrium curve of the melamine functionalized porous organic polymer to iodine in cyclohexane for example 1.
Fig. 11 is a graph of the reusability of the melamine functionalized porous organic polymer to iodine vapor in example 1.
Detailed Description
The present invention is further described in conjunction with specific embodiments below to facilitate understanding and application by those skilled in the art.
EXAMPLE 1 preparation of Melamine-functionalized porous organic Polymer
1. Raw materials
Triptycene: shanghai microphone Lin Biochemical technology Co., ltd, purity 99%;
terephthaloyl chloride: shanghai microphone Lin Biochemical technology Co., ltd, purity 99%;
melamine: shanghai microphone Lin Biochemical technology Co., ltd, purity 99%;
anhydrous ferric chloride: shanghai microphone Lin Biochemical technology Co., ltd, purity 99%;
dichloromethane: the product of Tianjin chemical reagent company, miou chemical reagent company, is analytically pure;
methanol: the product of Tianjin chemical reagent company, miou chemical reagent company, is analytically pure;
dimethyl sulfoxide: the product of Tianjin chemical reagent company, miou chemical reagent company, is analytically pure;
water: ultrapure water was purified by a Milli-Q purification apparatus (Miibo, USA) to have a resistivity of 18.2 M.OMEGA.cm.
2. Reaction vessel and apparatus
Round bottom flask: 250mL and 100mL;
vacuum drying box: DZF-6050, a constant scientific instrument, shanghai.
3. Preparation method
The method for preparing the melamine functional porous organic polymer comprises the following steps:
first, 0.609g of terephthaloyl chloride and 0.509g of triptycene were added to a 250mL round bottom flask containing 100mL of methylene chloride, the solution was kept at 20 ℃, and then 0.973g of anhydrous ferric chloride was slowly added; then stirring the solution under the protection of nitrogen and carrying out reflux reaction for 12 hours at 70 ℃; after the reaction is finished and cooled to room temperature, filtering to obtain white precipitate, thoroughly washing with dichloromethane, methanol and water respectively (three times), further purifying in a Soxhlet extractor with a mixed solution of water and methanol in a volume ratio of 1:1 for 24 hours to remove anhydrous ferric chloride serving as a catalyst, 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 melamine of the obtained ketone-based polymer precursor in 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 cooled to room temperature, the white precipitate obtained by filtration is thoroughly washed with dimethyl sulfoxide, methanol and water respectively (three times), and then is further purified for 24 hours by a mixed solution of water and methanol in a volume ratio of 1:1 in a Soxhlet extractor; finally, vacuum drying is carried out for 12 hours in a vacuum drying oven at 60 ℃ to obtain the melamine functionalized porous organic polymer (TPC-TC-MA). The synthetic route is shown in FIG. 1.
EXAMPLE 2 characterization of the porous organic Polymer (TPC-TC-MA) prepared in example 1 of the invention
1. And (3) infrared spectrum analysis: the TPC-TC-MA prepared in example 1 and its corresponding monomers were characterized by a Fourier transform infrared spectrometer, the Fourier transform infrared spectrometer of which is shown in FIG. 2, from which it can be seen that: TPC-TC at 1657 cm -1 The telescopic vibration absorption peak of c=o appears, indicating that the ketone based polymer precursor TPC-TC was successful by Friedel-Crafts acylation. And 1558 cm -1 And 1350 cm -1 The bands at this point were attributed to c=n and C-N stretching vibrations, respectively, of the triazine ring, indicating successful crosslinking of melamine with the ketone based polymer precursor.
2. Scanning electron microscope analysis: the TPC-TC-MA prepared in example 1 was observed using a scanning electron microscope, and the results were shown in FIG. 3, in which the synthesized material was seen to exhibit an irregular granular aggregate structure.
3. Transmission electron microscopy analysis: the TPC-TC-MA prepared in example 1 was observed by transmission electron microscopy, and the results are shown in fig. 4, in which the synthesized material was observed to be disordered in pore channels.
4. Crystal type analysis: the crystal type of TPC-TC-MA prepared in example 1 was characterized by X-ray diffractometer (XRD), the XRD pattern of which is shown in fig. 5, and as can be seen from fig. 5, the prepared material exhibited amorphous characteristics.
5. Thermogravimetric analysis: thermogravimetric analysis was performed on the TPC-TC-MA prepared in example 1 under argon atmosphere 5 ℃/min test conditions, and the thermogravimetric curve is shown in fig. 6. It can be seen from the figure that these polymer backbones start to decompose largely at 350 c, indicating that the polymers have very good thermal stability. Meanwhile, the samples are found not to be dissolved or decomposed in common organic solvents (methanol, ethanol, methylene dichloride, chloroform, tetrahydrofuran, acetone, N' -dimethylformamide and the like), and the polymer is proved to have very good chemical stability.
5. Nitrogen adsorption and desorption analysis: the TPC-TC-MA prepared in example 1 was subjected to a nitrogen adsorption-desorption isothermal curve test, and the BET specific surface area of the prepared polymer was 584 m as shown in FIG. 7 2 /g。
7. Pore size distribution: the pore size distribution of the TPC-TC-MA prepared in example 1 was calculated according to the non-localized density functional theory method, and as can be seen from FIG. 8, the prepared material had abundant micropores.
EXAMPLE 3 adsorption of iodine molecules by the porous organic Polymer (TPC-TC-MA) prepared in example 1 of the present invention
1. Adsorption of gaseous iodine by TPC-TC-MA
Placing 10 mg melamine functionalized porous organic polymer (TPC-TC-MA) into an open vial, placing the vial into a glass vial containing 1.0 g iodine simple substance, sealing the glass vial, and placing the glass vial into an oven at 75 ℃ 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 method has high adsorption capacity to iodine, which reaches 254.1wt%.
2. Adsorption of iodine in cyclohexane solution by TPC-TC-MA
10 mg adsorbents were dispersed in 10 mL 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 conforms to the Langmuir and Frundlich models, and the highest adsorption capacity of TPC-TC-MA is 380.2 mg/g.
3. Reuse efficiency test
Investigation of the recycling ratio of the melamine functionalized porous organic polymer TPC-TC-MA prepared in example 1: and washing the material after absorbing the iodine vapor with methanol solution for a plurality of times to remove iodine molecules in the pore channels, drying the material, and then using the dried material for the next round of iodine vapor absorption. From fig. 11, it can be seen that after five times of recycling, the material prepared in the embodiment 1 still has higher adsorption performance on iodine vapor, and proves that the material can be recycled, and has a good application prospect for treating radioactive iodine in nuclear waste.
Claims (5)
1. A process for preparing a melamine functionalized porous organic polymer characterized by: comprising the following steps:
dissolving terephthaloyl chloride and triptycene in a dichloromethane solvent, adding an anhydrous ferric chloride catalyst at 20 ℃ to form a mixed solution, carrying out reflux reaction at 70 ℃ for 12 hours under the protection of nitrogen, cooling to room temperature, washing an obtained white precipitate with dichloromethane, methanol and water in sequence, purifying for 24 hours with the mixed solution of water and methanol, and vacuum-drying the obtained white product at 60 ℃ for 12 hours to obtain a ketone-based polymer precursor;
secondly, dissolving the obtained ketone-based polymer precursor in dimethyl sulfoxide, adding melamine, carrying out reflux reaction for 72 hours at 160 ℃ under the protection of nitrogen after uniform mixing, cooling to room temperature, washing the obtained white precipitate with dimethyl sulfoxide, methanol and water in sequence, and purifying for 24 hours with a mixed solution of water and methanol; the white product obtained was dried in vacuo at 60 ℃ for 12 hours to give a melamine functionalized porous organic polymer having the following structural formula:
2. the method for preparing a melamine functionalized porous organic polymer according to claim 1, characterized in that: the mole ratio of triptycene, terephthaloyl chloride and anhydrous ferric chloride serving as a catalyst in the first step is 2:3:6.
3. The method for preparing a melamine functionalized porous organic polymer according to claim 1, characterized in that: the mass ratio of the ketone-based polymer precursor to the melamine in the second step is 1:6.
4. The method for preparing a melamine functionalized porous organic polymer according to claim 1, characterized in that: the volume ratio of water to methanol used for purifying the white precipitate in the first step and the second step is 1:1.
5. Use of the melamine functionalized porous organic polymer prepared according to any one of claims 1 to 4 as a radioiodinated adsorbent.
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