CN113087864B - Preparation method of heterocyclic covalent organic polymer and application of heterocyclic covalent organic polymer in uranyl ion adsorption - Google Patents
Preparation method of heterocyclic covalent organic polymer and application of heterocyclic covalent organic polymer in uranyl ion adsorption Download PDFInfo
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Abstract
The invention discloses a preparation method of a heterocyclic covalent organic polymer and application of the heterocyclic covalent organic polymer in uranyl ion adsorption, and belongs to the technical field of environmental protection. 2,4, 6-trialdehyde resorcinol and 3,3 '-diaminodiphenylamine are reacted through Schiff base to prepare the 2,4, 6-trialdehyde resorcinol-3, 3' -diaminodiphenylamine heterocycle covalent organic polymer. The heterocyclic covalent organic polymer takes the imidazole functional group as a connecting unit, and a large number of hydroxyl functional groups are arranged around the imidazole functional group, so that the adsorption capacity of uranyl ions can be improved, and the heterocyclic covalent organic polymer has good selectivity on adsorption of the uranyl ions. The method for preparing the heterocyclic covalent organic polymer is simple, stable in structure, environment-friendly, high in adsorption efficiency and good in selectivity on uranyl ions in a water body, and can be used as a high-efficiency adsorbent for the uranyl ions.
Description
Technical Field
The invention belongs to the technical field of environmental protection, and particularly relates to a preparation method of a heterocyclic covalent organic polymer and application of the heterocyclic covalent organic polymer in uranyl ion adsorption.
Background
As a primary fuel for the nuclear industry, uranium plays a key role in sustainable energy supply and development. However, unreasonable discharge of large-scale nuclear power wastewater, traditional mining of terrestrial uranium ores, unpredictable nuclear accidents and improper disposal of nuclear-containing wastewater in the nuclear waste post-treatment process can cause radioactive uranium elements to be discharged into the environment, and seriously threaten the ecological environment and human health. Therefore, the safe and efficient uranium adsorbent is very important for environmental protection and social development. However, conventional adsorbent Materials (e.g. zeolites, activated carbon, clays, etc.) have difficulty meeting practical application requirements for uranium-containing waste liquids due to relatively low adsorption capacity and poor selectivity (c.w. abney, r.t. mayes, t.saito, s.dai, Materials for the recovery of uranium from seawater, chem.rev.2017,117, 13935-14013). Covalent organic polymers have the advantages of firm covalent bond connection, high chemical stability, adjustable function and the like, are a new-generation porous material with great prospect and are widely applied to the fields of environmental protection and the like (X.Li, Y.Zou, Z.jia, J.Zhang, Y.Li, X.Guo, M.Zhang, K.Li, J.Li, L.Ma, Afully conjugated organic polymeric via Knoevenagel condensation for fast separation of ammonium, J.Hazard.Mater.2021,401, 123802). Meanwhile, due to the high affinity to uranyl ions, amidoxime groups are widely applied to the post-treatment process of uranium-containing wastewater. However, modification of amidoxime groups on porous materials usually requires complex post-treatment, which is time-consuming and results in a decrease in the yield, stability and porosity of the material. In addition, the amidoxime group selectivity is not satisfactory, and has a certain affinity for other metal ions such as vanadium, copper, iron, etc. (J.Wang, S.Zhuang, Extraction and adsorption of U (VI) from aqueous solution using affinity-based technologies: an overview, Rev.Environ.Sci.Biotechnology.2019, 18, 437-452). Therefore, it is important to develop a novel uranyl ion adsorption functional group and an adsorption material which are easy to prepare, high in adsorption capacity, fast in adsorption rate and high in selectivity.
Generally, biomolecules containing multiple functional groups in the human body can coordinate with metal ions, and for example, uranium element forms a stable complex with transferrin, albumin, and red blood cells in blood when taken into or inhaled into the human body. According to literature, the binding site between transferrin and uranium is a histidine residue, whereas histidine is a polar basic amino acid consisting of imidazole side chains (n.c. li, b.e. doody, j.m. white, Some metal complexes of glycerol peptides 1, j.am.chem. soc.1957,79, 5859-5863). Further studies have shown that the imidazole group in histidine can coordinate with uranyl ion (K.E. Gutowski, V.A. Cocalia, S.T. Griffin, N.J. Bridges, D.A. Dixon, R.D. Rogers, Interactions of 1-methylimidazol with UO2(CH3CO2)2and UO2(NO3)2Structural, spectroscopic, and cosmetic evidence for binding of an imidazole to the urea, J.Am.chem.Soc.2007,129, 526-536). Thus, imidazole can be used as a novel uranyl ion adsorption functional group. However, in the practical application process, because the coordination capacity of nitrogen atoms to uranium is poor, the application of imidazole functional groups to uranyl ion adsorption is receivedAnd (5) determining a limit. According to the theory of soft-hard acid-base (HSAB), oxygen atoms can effectively enhance coordination affinity to metal ions (C.Bai, M.Zhang, B.Li, Y.Tian, S.Zhang, X.ZHao, Y.Li, L.Wang, L.Ma, S.Li, Three novel triazine-based materials with differential O/S/N set of donor atoms: One-step prediction and compliance of the coordination in selected section of ruthenium, J.Hazard.Mater.2015,300,368-377), and therefore, introduction of hydroxyl groups around imidazole functional groups would be a promising approach to increase the affinity of imidazole functional groups for uranyl ions.
In order to simplify the preparation process of the material and improve the adsorption capacity, the adsorption speed and the adsorption selectivity of the uranyl ion adsorption functional group, the heterocyclic covalent organic polymer is prepared by Schiff base reaction. At present, no report is found for preparing heterocyclic covalent organic polymers by Schiff base reaction and applying the polymers to adsorption of uranyl ions.
Disclosure of Invention
The invention aims to provide a preparation method of a heterocyclic covalent organic polymer and application of the heterocyclic covalent organic polymer in uranyl ion adsorption, and the heterocyclic covalent organic polymer has the advantages of simple preparation method, high adsorption capacity, high adsorption rate, strong anti-interference capability and the like, and is a high-efficiency uranyl ion adsorbent.
The invention provides a preparation method of a heterocyclic covalent organic polymer, which comprises the following steps:
1) taking 2,4, 6-trialdehyde resorcinol and 3,3' -diaminodiphenylamine as reaction raw materials, adding 1, 4-dioxane and mesitylene, carrying out ultrasonic treatment on the mixed solution, and adding an HAc solution to obtain a reaction mixed solution;
2) degassing the container containing the reaction mixture by freezing-thawing cycle, sealing with flame, heating at 120 deg.C for 2-4 days, cooling, and filtering;
3) and (3) taking the solid precipitate after filtration, washing the solid precipitate with anhydrous tetrahydrofuran, N-dimethylformamide and N, N-dimethylacetamide respectively, and drying the solid precipitate in vacuum at the temperature of 60 ℃ for 8 hours to obtain the heterocyclic covalent organic polymer (BdDAB) with the imidazole functional group as the connecting unit.
Further, the mass ratio of the 2,4, 6-trialdehyde resorcinol to the 3,3' -diaminodiphenylamine in the step 1) is 1: (1.5-2).
The invention also provides an application of the heterocyclic covalent organic polymer in adsorption of uranyl ions, which comprises the following steps:
and adding the heterocyclic covalent organic polymer into a solution to be treated containing uranyl ions, and oscillating at constant temperature.
Further, the concentration range of the solution to be treated containing the uranyl ions is 25-280 mg/L.
Further, before the heterocyclic covalent organic polymer is mixed with the solution to be treated containing the uranyl ions, a pH regulator is adopted to regulate the pH value of the heterocyclic covalent organic polymer to be 1.0-8.0; preferably, the pH is 4.5.
Further, the method also comprises the step of filtering the mixed solution after oscillation by adopting a 0.22 mu m microporous filter membrane.
Compared with the prior art, the invention has the beneficial effects that:
(1) the heterocyclic covalent organic polymer is synthesized by adopting a one-step method, the preparation method is simple, the structure is stable, the environment is friendly, and the complex post-treatment is not needed, so that the heterocyclic covalent organic polymer can be directly used for adsorbing uranyl ions.
(2) The heterocyclic covalent organic polymer prepared by the invention takes imidazole functional groups as uranyl ion adsorption groups, replaces the traditional amidoxime functional groups with larger toxicity, and is beneficial to sustainable development of ecological environment.
(3) The heterocyclic covalent organic polymer taking imidazole as a connecting unit prepared by the invention has a large number of hydroxyl functional groups around the imidazole functional group, so that the adsorption capacity of uranyl ions is greatly improved.
(4) The heterocyclic covalent organic polymer prepared by the invention has excellent selectivity on uranyl ions.
(5) The heterocyclic covalent organic polymer prepared by the invention realizes rapid high-capacity adsorption of uranyl ions in a water sample, is a high-efficiency adsorbent and remover of the uranyl ions, and has good application prospect.
Drawings
FIG. 1 is a schematic diagram of the preparation process of heterocyclic covalent organic polymer BdDAB.
FIG. 2 is an infrared spectrum of Bd, DAB and BdDAB.
Figure 3 is an SEM image of heterocyclic covalent organic polymer BdDAB.
FIG. 4 shows pH value versus adsorption UO of heterocyclic covalent organic polymer BdDAB2 2+Impact graph of performance.
FIG. 5 is a heterocyclic covalent organic polymer BdDAB vs UO2 2+Adsorption isotherm diagram of (1).
FIG. 6 is a heterocyclic covalent organic polymer BdDAB vs UO2 2+Adsorption kinetics of (c).
Detailed Description
The technical solution of the present invention will be described clearly and completely with reference to the following examples, which are only a part of the examples of the present invention, but not all of them, which are conventional processes unless otherwise specified, and the raw materials which are commercially available from the public unless otherwise specified. All other embodiments, which can be derived by a person skilled in the art from the embodiments of the present invention without making creative efforts, fall within the protection scope of the present invention.
Example 1: preparation method and property characterization of heterocyclic covalent organic polymer (BdDAB)
2,4, 6-trialdehyde resorcinol (Bd, 0.048g, 0.25mmol), 3' -diaminodiphenylamine (DAB, 0.082g, 0.38mmol), 1, 4-dioxane (4.0mL) and mesitylene (2.0mL) were charged into a 20mL pyrex glass tube, sonicated for 10 minutes, and HAc solution (0.5mL, 6M) was added to obtain a reaction mixture solution; degassing a pyrex glass tube filled with a reaction mixed solution by three times of freeze pump-unfreezing circulation, sealing the pyrex glass tube by flame, heating the pyrex glass tube in an oven at 120 ℃ for 3 days, cooling, filtering and separating brick red products, washing the brick red products by anhydrous Tetrahydrofuran (THF), N-Dimethylformamide (DMF) and N, N-Dimethylacetamide (DMA) for several times respectively, collecting solids, and drying the solids in vacuum at 60 ℃ for 8 hours to obtain the 2,4, 6-trialdehyde resorcinol-3, 3' -diaminodiphenylamine heterocycle covalent organic polymer (BdDAB) with imidazole functional groups as connecting units.
FIG. 1 is a schematic diagram of the preparation process of heterocyclic covalent organic polymer BdDAB.
FIG. 2 is an infrared spectrum of Bd, DAB and BdDAB. Compared with the infrared spectrograms of Bd and DAB, the infrared spectrogram of BdDAB is 3434cm-1、1616cm-1And 1280cm-1New absorption bands appear, corresponding to the stretching vibration peaks of N-H, C ═ N and C-N of imidazole ring respectively, and the successful preparation of 2,4, 6-trialdehyde resorcinol-3, 3' -diamino diphenylamine heterocycle covalent organic polymer BdDAB with imidazole functional group as a connecting unit is shown.
And (3) adopting a Scanning Electron Microscope (SEM) to represent the shape of BdDAB. As can be seen from FIG. 3, the heterocyclic covalent organic polymer BdDAB has an obvious loose porous structure, the structure greatly increases the number of active sites of BdDAB, and is favorable for adsorbing uranyl ions (UO)2 2+) And increase the ratio of the pair UO2 2+The adsorption capacity of (c).
SEM and infrared characterization results show that the heterocyclic covalent organic polymer BdDAB is successfully prepared by the method.
Example 2: optimization of the Experimental conditions
The pH value has an effect on the basic morphology of uranium and the extraction capacity of the adsorbent, and therefore the effect of pH (1.0-4.5) on the performance of the adsorbent was investigated. Adjusting the pH value of the solution to be changed within the range of 1.0-4.5 by using nitric acid or sodium hydroxide solution, adding 4mg of heterocyclic covalent organic polymer into 20mL of aqueous solution with the uranyl ion concentration of 75mg/L, oscillating for 12 hours by using a constant-temperature oscillator, filtering by using a 0.22 mu m microporous filter membrane, measuring the content of residual uranyl ions in the filtrate by using inductively coupled plasma mass spectrometry, and calculating the adsorption capacity of the heterocyclic covalent organic polymer on the uranyl ions. FIG. 4 shows pH value versus adsorption UO of heterocyclic covalent organic polymer BdDAB2 2+Impact graph of performance. As can be seen from fig. 4, the adsorption capacity increases with increasing pH. Heterocyclic covalent organic polymers BdDAB to UO at pH 1.02 2+The adsorption capacity is high; BdDAB vs UO at pH 4.52 2+The maximum adsorption capacity of (A) was 276.5 mg/g. The pH value affects the basic form of uranium element, and when the pH value is more than 4.5，UO2 2+A precipitate will form in aqueous solution. Therefore, pH 4.5 was selected as the optimum pH.
Example 3: heterocyclic covalent organic polymers BddDAB to UO2 2+Adsorption and removal of
Researches on adsorption of initial concentration and adsorption time of uranium on UO of heterocyclic covalent organic polymer BdDAB2 2+The influence of (c). Adjusting pH of the solution to 4.5 with nitric acid or sodium hydroxide solution, adding 4mg of heterocyclic covalent organic polymer BdDAB into 20mL solution containing UO of different concentrations2 2+(25-280mg/L) in the water solution, shaking for 12 hours by using a constant temperature oscillator, filtering by using a 0.22 mu m microporous membrane, and measuring the remaining UO in the filtrate by using an inductively coupled plasma mass spectrometry2 2+Content, calculation of heterocyclic covalent organic Polymer Pair UO2 2+The adsorption capacity of (A) is used for drawing heterocyclic covalent organic polymer BdDAB to UO2 2+Adsorption isotherm of (1). FIG. 5 is a heterocyclic covalent organic polymer BdDAB vs UO2 2+Adsorption isotherm diagram of (1). As can be seen from FIG. 5, the driving force of the concentration gradient of the solid-liquid interface is large, and the heterocyclic covalent organic polymer BdDAB is used for UO2 2+Adsorption capacity of (2) with UO2 2+The ion concentration is increased until reaching an equilibrium state, and the isothermal adsorption process is found to accord with a Langmuir model through fitting, which indicates that the heterocyclic covalent organic polymer BdDAB is used for UO2 2+The adsorption is single-layer adsorption, and heterocyclic covalent organic polymers BdDAB are used for UO2 2+The maximum adsorption capacities of (A) and (B) were 368.3mg/g, respectively.
With 0.1M nitric acid or sodium hydroxide solution2 2+The pH of the aqueous solution of (1) was adjusted to 4.5, and 4mg of heterocyclic covalent organic polymer BdDAB was placed in 200mL of UO2 2+Stirring 25mg/L water solution for different time, sampling, filtering with 0.22 μm microporous membrane, and measuring remaining UO in the filtrate by inductively coupled plasma mass spectrometry2 2+Content, calculation of heterocyclic covalent organic Polymer Pair UO2 2+The adsorption capacity of (A) is used for drawing heterocyclic covalent organic polymer BdDAB to UO2 2+Adsorption of (2)Kinetic curves. FIG. 6 is a heterocyclic covalent organic polymer BdDAB vs UO2 2+Adsorption kinetics of (c). As can be seen in FIG. 6, the heterocyclic covalent organic polymers BdDAB vs UO2 2+The adsorption kinetics of the method accord with a pseudo-second-order kinetics process, the adsorption speed is high, the adsorption capacity is increased rapidly within 3 hours and then is increased slowly, saturated adsorption is achieved within about 5.5 hours, and the high adsorption rate shows that the heterocyclic covalent organic polymer BdDAB prepared by the method has high uranium adsorption efficiency and good application prospect.
Example 4: heterocyclic covalent organic polymer BdDAB adsorbs UO2 2+Selectivity of (2)
The adsorption of other coexisting metal ions on the heterocyclic covalent organic polymer BdDAB to UO is investigated2 2+The influence of selectivity of (c). La3+,Ce3+,Nd3+,Sm3+,Gd3+,VO3-,Cd2+,Ni2+,Co2+,Na+,K+,Mg2+,Al3+,Zn2+And Ca2+Plasma metal ions are widely present in natural water bodies and nuclear industrial wastewater, and tend to interfere with the UO pairing by occupying binding sites on the surface of the adsorbent or changing the surface charge of the adsorbent through competition2 2+Adsorption of (3). In 30mL of UO containing 5mg/L2 2+Adding 4mg heterocyclic covalent organic polymer BdDAB into the mixed solution of the same concentration interference metal ions, stirring for 12h, filtering by using a 0.22 mu m microporous filter membrane, and measuring the remaining UO in the filtrate by using inductively coupled plasma mass spectrometry2 2+Content, calculation of heterocyclic covalent organic Polymer Pair UO2 2+Adsorption capacity of (1), test La3+,Ce3+,Nd3+,Sm3+,Gd3+,VO3-,Cd2+,Ni2+,Co2+,Na+,K+,Mg2+,Al3+,Zn2+And Ca2+Metal ions and above metal ions and UO2 2+Absorbing UO on heterocyclic covalent organic polymer BdDAB during mixing2 2+The influence of (c). As a result, it was revealed that the above coexisting metalsThe ions have little influence on uranium adsorption of the heterocyclic covalent organic polymer BdDAB, the adsorption capacity of the heterocyclic covalent organic polymer BdDAB on uranyl ions is still as high as 25.0mg/g under the condition of the existence of mixed metal ions, and the adsorption capacity on other metal ions including lanthanide metal elements, transition metal elements and main group metal elements is lower than 2.0 mg/g. This is mainly due to the heterocyclic covalent organic polymer BdDAB selectively reacting with UO via imidazole and hydroxyl groups2 2+Chelation occurs. The results show that the heterocyclic covalent organic polymer BdDAB prepared by the method is used for UO2 2+The adsorption has the advantage of strong anti-interference capability, and is a high-efficiency uranyl ion adsorbent.
The foregoing is only a preferred embodiment of the present invention and it should be noted that modifications and adaptations can be made by those skilled in the art without departing from the principle of the present invention and are intended to be included within the scope of the present invention.
Claims (8)
1. A method of preparing a heterocyclic covalent organic polymer, comprising the steps of:
1) taking 2,4, 6-trialdehyde resorcinol and 3,3' -diaminodiphenylamine as reaction raw materials, adding 1, 4-dioxane and mesitylene, carrying out ultrasonic treatment on the mixed solution, and adding an HAc solution to obtain a reaction mixed solution;
2) degassing the container containing the reaction mixture by freezing-thawing cycle, sealing with flame, heating at 120 deg.C for 2-4 days, cooling, and filtering;
3) and (3) taking the filtered solid precipitate, washing the solid precipitate with anhydrous tetrahydrofuran, N-dimethylformamide and N, N-dimethylacetamide respectively, and drying the solid precipitate in vacuum at the temperature of 60 ℃ for 8 hours to obtain the heterocyclic covalent organic polymer with the imidazole functional group as the connecting unit.
2. The method of claim 1, wherein the mass ratio of 2,4, 6-trianilino resorcinol to 3,3' -diaminodiphenylamine in step 1) is 1: (1.5-2).
3. Use of a heterocyclic covalent organic polymer obtained by the process of claim 1 or 2 for adsorbing uranyl ions.
4. The use of the heterocyclic covalent organic polymer for adsorbing uranyl ions according to claim 3, wherein the heterocyclic covalent organic polymer is added to a solution to be treated containing uranyl ions and shaken at a constant temperature.
5. Use of the heterocyclic covalent organic polymer for the adsorption of uranyl ions according to claim 4, wherein the solution to be treated containing uranyl ions has a concentration ranging from 25 to 280 mg/L.
6. The use of a heterocyclic covalent organic polymer for adsorbing uranyl ions according to claim 4 wherein the heterocyclic covalent organic polymer is further adjusted to a pH of 1.0 to 8.0 with a pH adjusting agent prior to mixing with the solution to be treated containing uranyl ions.
7. Use of the heterocyclic covalent organic polymer for the adsorption of uranyl ions according to claim 6 wherein the pH is adjusted to 4.5.
8. The use of the heterocyclic covalent organic polymer for adsorbing uranyl ions according to claim 4, further comprising filtering the shaken mixture through a 0.22 μm microfiltration membrane.
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