CN111589429B - Phenanthroline polymer and preparation method and application thereof - Google Patents
Phenanthroline polymer and preparation method and application thereof Download PDFInfo
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- CN111589429B CN111589429B CN202010466648.3A CN202010466648A CN111589429B CN 111589429 B CN111589429 B CN 111589429B CN 202010466648 A CN202010466648 A CN 202010466648A CN 111589429 B CN111589429 B CN 111589429B
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- C02F1/00—Treatment of water, waste water, or sewage
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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Abstract
The invention provides a phenanthroline polymer and a preparation method and application thereof, and belongs to the technical field of water treatment. The preparation method of the phenanthroline polymer provided by the invention comprises the following steps: mixing the acetonitrile solution of 1, 10-phenanthroline with an oxidant, and carrying out oxidative polymerization to obtain the phenanthroline polymer. The invention takes 1, 10-phenanthroline as a monomer for the first time, and adopts an oxidative polymerization method to prepare the phenanthroline polymer, wherein the method belongs to bulk free radical polymerization and has the advantages of simple process, easy operation and no impurities. The phenanthroline polymer prepared by the method has a plurality of exposed sites, has the advantages of large adsorption capacity and high removal rate when used as a heavy metal ion adsorbent, and has a wide application prospect in removing heavy metal ions in water.
Description
Technical Field
The invention relates to the technical field of water treatment, and particularly relates to a phenanthroline polymer and a preparation method and application thereof.
Background
Currently, a lot of toxic heavy metal-containing industrial wastewater is generated in many industrial production processes, such as electroplating, metallurgy, metal finishing, mining and other industrial production processes. For many years, people are constantly developing and improving methods and technologies for treating heavy metal ion wastewater. At present, methods for removing harmful heavy metals in wastewater include a sulfuration method, a chemical precipitation method, a membrane filtration method, a flocculation method, a solvent extraction method, an adsorption method and the like. Among them, the adsorption method is attracting attention due to its unique advantages. The key materials in the adsorption method are adsorbents, the heavy metal ion adsorbents are various and have wide range, and the adsorbents comprise natural minerals, such as inorganic materials of zeolite, kaolinite and the like, natural high polymers, such as tannins, lignins, chitosan and the like, and artificially synthesized or modified polymers, such as polystyrene-based resin, silica gel-based resin and the like.
At present, the polymerization methods commonly used for synthesizing the polymers include bulk polymerization, suspension polymerization, solution polymerization and emulsion polymerization, and the currently common polymerization methods include thermal initiation polymerization, molecular imprinting polymerization, ring-opening polymerization and the like. However, the existing polymerization method has complex synthesis steps, few polymer exposed sites and low adsorption capacity rate to low-concentration heavy metal ions in water.
Disclosure of Invention
The invention aims to provide a phenanthroline polymer and a preparation method and application thereof, and the prepared phenanthroline polymer has many exposed sites and high adsorption capacity to heavy metal ions.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a preparation method of a phenanthroline polymer, which comprises the following steps:
mixing the acetonitrile solution of 1, 10-phenanthroline with an oxidant, and carrying out oxidative polymerization to obtain the phenanthroline polymer.
Preferably, the oxidant is ammonium persulfate, the oxidant is used in the form of a solution, and the concentration of the oxidant in the solution of the oxidant is 0.25 mol/L.
Preferably, the molar ratio of the 1, 10-phenanthroline to the oxidant is (1-4): 1.
Preferably, in the acetonitrile solution of 1, 10-phenanthroline, the concentration of 1, 10-phenanthroline is 0.15-0.30 mol/L.
Preferably, the temperature of the oxidative polymerization is 70-100 ℃, and the time is 3-15 h.
Preferably, the oxidative polymerization is carried out under the conditions of stirring and nitrogen protection, and the rotation speed of the stirring is 100-550 r/min.
Preferably, after the oxidative polymerization is completed, the method further comprises: and sequentially cooling, standing, separating, drying and grinding the obtained reaction system to obtain the phenanthroline polymer.
The invention provides the phenanthroline polymer prepared by the preparation method in the technical scheme.
The invention provides the application of the phenanthroline polymer in the technical scheme in adsorbing heavy metal ions in wastewater.
The invention provides a preparation method of a phenanthroline polymer, which comprises the following steps of mixing 1, 10-phenanthroline acetonitrile solution with an oxidant, and carrying out oxidative polymerization to obtain the phenanthroline polymer.
The invention takes 1, 10-phenanthroline as a monomer for the first time, and adopts an oxidative polymerization method to prepare the phenanthroline polymer, wherein the method belongs to bulk free radical polymerization and has the advantages of simple process, easy operation and no impurities.
The phenanthroline polymer prepared by the oxidative polymerization method is of a long-chain structure, all binding sites N can be exposed by the structure, and the N and metal can be bound in a coordination mode, so that the phenanthroline polymer prepared by the method disclosed by the invention has many exposed sites, has the advantages of large adsorption capacity and high removal rate when being used as a heavy metal ion adsorbent, and has a wide application prospect in removing heavy metal ions in a water body.
The phenanthroline polymer prepared by the invention is used for Ag+Has specific adsorption function and higher adsorption capacity, and the maximum adsorption capacity reaches 247.4 mg/g.
Drawings
FIG. 1 shows Ag in the application example+And (3) a trend graph of the influence of the initial concentration of the solution on the adsorption capacity of the phenanthroline polymer.
Detailed Description
The invention provides a preparation method of a phenanthroline polymer, which comprises the following steps:
mixing the acetonitrile solution of 1, 10-phenanthroline with an oxidant, and carrying out oxidative polymerization to obtain the phenanthroline polymer.
In the present invention, unless otherwise specified, all the starting materials required for the preparation are commercially available products well known to those skilled in the art.
The invention mixes 1, 10-phenanthroline acetonitrile solution with oxidant. In the invention, the 1, 10-phenanthroline is used as a monomer for preparing an o-phenanthroline polymer, and the structural formula of the 1, 10-phenanthroline is as follows:
in the invention, the concentration of 1, 10-phenanthroline in the acetonitrile solution of 1, 10-phenanthroline is 0.15-0.30 mol/L, and more preferably 0.25 mol/L. In the present invention, the preparation process of the acetonitrile solution of 1, 10-phenanthroline is preferably that 1, 10-phenanthroline and acetonitrile are mixed and ultrasonically dissolved. The process of the ultrasound is not particularly limited, and 1, 10-phenanthroline can be completely dissolved by adopting a process well known in the art.
In the invention, the oxidant is preferably ammonium persulfate, the oxidant is preferably used in the form of a solution, the solvent used for the solution of the oxidant is preferably water, more preferably deionized water, and the concentration of the oxidant in the solution of the oxidant is preferably 0.25 mol/L. The oxidant Ammonium Persulfate (APS) used in the invention does not contain metal ions, has strong oxidizing capability, does not introduce other impurities and byproducts which are not easy to remove, and has simple subsequent treatment.
In the invention, the molar ratio of the 1, 10-phenanthroline to the oxidant is preferably (1-4): 1, and more preferably (2-3): 1. The mixing process of the 1, 10-phenanthroline acetonitrile solution and the oxidant is not particularly limited, and the materials can be uniformly mixed by adopting a process well known in the art.
After mixing 1, 10-phenanthroline acetonitrile solution and an oxidant, carrying out oxidative polymerization on the obtained mixed system. In the invention, the temperature of the oxidative polymerization is preferably 70-100 ℃, more preferably 80-90 ℃, and the time is preferably 3-15 h, more preferably 5-10 h, and further preferably 6-8 h.
In the invention, the oxidative polymerization is preferably carried out under the conditions of stirring and nitrogen protection, and the rotation speed of the stirring is preferably 100-550 r/min, more preferably 200-450 r/min, and further preferably 300-400 r/min; the oxidative polymerization is preferably carried out under the heating condition of an oil bath, and the oxidative polymerization is preferably carried out in a sealed apparatus.
Before the oxidative polymerization reaction, H is connected to C at the N-ortho position on the 1, 10-phenanthroline monomer, when the oxidative polymerization reaction occurs, a redox reaction is caused by single electron transfer between an oxidant and the monomer 1, 10-phenanthroline to generate free radicals, the 1, 10-phenanthroline monomer is sequentially connected together through the free radicals to form a polymer long chain, namely, the 1, 10-phenanthroline monomer is subjected to self polymerization under the action of the oxidant to form an o-phenanthroline polymer.
In the present invention, after the completion of the oxidative polymerization, it is preferable to further include: and sequentially cooling, standing, separating, drying and grinding the obtained reaction system to obtain the phenanthroline polymer. In the present invention, the processes of cooling, standing, separating, drying and grinding are particularly preferably to cool the reaction system obtained by oxidative polymerization to room temperature, standing for 2 hours and then filtering; putting the obtained filtrate into acetonitrile, repeating ultrasonic ultrafiltration for 5 times, and washing away residual phenanthroline monomers; eluting the obtained filtrate in ultrapure water, performing ultrasonic treatment for 3min, performing suction filtration, repeating the ultrapure water elution-ultrasonic treatment-suction filtration process for 5 times, and washing off residual persulfate; putting the obtained product into a 70 ℃ oven for drying for 6 hours; and (3) putting the dried product into a mortar, and grinding until the powder has no granular sensation to obtain the phenanthroline polymer. As another scheme of the invention, after standing for 2 hours, separating a supernatant, mixing a subnatant with deionized water (the volume ratio of the subnatant to the deionized water is preferably 1:10), standing for 6 hours, filtering, and sequentially performing ultrasonic filtration, ultrapure water elution-ultrasonic filtration process, drying and grinding on the obtained filtrate according to the steps to obtain the phenanthroline polymer. The process of the present invention for the ultrasonic treatment, the suction filtration and the grinding is not particularly limited, and may be performed according to a process well known in the art.
The principle of the invention for separating out the polymer product by using deionized water is as follows: water is a good solvent for the polymer, and the polymer can convert a rigid chain into a flexible chain in water, so that more monomers can be polymerized, and the molecular weight of the polymer is increased.
The invention provides the phenanthroline polymer prepared by the preparation method in the technical scheme.
The structural unit of the phenanthroline polymer prepared by the invention is shown as a formula I:
The invention provides the application of the phenanthroline polymer in the technical scheme in adsorbing heavy metal ions in wastewater. The method for applying the phenanthroline polymer is not particularly limited in the invention, and the phenanthroline polymer is used for adsorbing heavy metal ions in wastewater according to an application method well known in the art. In the application example of the invention, an isothermal adsorption experiment is specifically adopted to test the adsorption performance of the phenanthroline polymer, and the specific method comprises the following steps: respectively preparing Ag with initial concentration of 0-1200 mg/L+Respectively taking 20mL of the solution into conical flasks, respectively adding 20mg of prepared phenanthroline polymer into the conical flasks, putting the conical flasks into a constant-temperature shaking box at 25 ℃ and 180r/min, reacting for 24 hours, respectively taking a small amount of reacted solution after reaction, and detecting Ag in the solution by using a flame atomic absorption spectrophotometer+Concentration and calculating the adsorption quantity Q of the adsorbent at different initial concentrationseThe formula for calculating the adsorption capacity of the phenanthroline polymer is as follows:
in the formula: c0Ag in the initial solution+Concentration (mg/L);
Ceag in solution after adsorption+Concentration (mg/L);
Qe-phenanthroline polymer vs. Ag+Adsorption capacity (mg/g);
V-Ag+volume of solution (L);
mass (g) of W-phenanthroline polymer.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Placing 1mol of 1, 10-phenanthroline monomer in a round-bottom flask, adding 160mL of acetonitrile, and performing ultrasonic treatment until the mixture is completely dissolved to obtain a solution with the concentration of 0.25 mol/L; preparing 0.25mol/L Ammonium Persulfate (APS) aqueous solution; slowly adding 40mLAPS aqueous solution into a flask, vacuumizing, introducing nitrogen for protection, starting a stirring switch, setting the stirring speed to be 550r/min, starting a heating switch, setting the oil bath temperature to be 70 ℃, carrying out oxidative polymerization for 15h, and keeping the device sealed; after the reaction is finished, cooling the obtained reaction system to room temperature, standing for 2 hours, and separating supernatant; adding the subnatant into deionized water (the volume ratio of the subnatant to the deionized water is 1:10), standing for 6h, and filtering; putting the obtained filtrate into acetonitrile, and repeating ultrasonic ultrafiltration for 5 times; eluting the obtained filtrate in ultrapure water, performing ultrasonic treatment for 3min, vacuum filtering, and repeating ultrapure water elution-ultrasonic treatment-vacuum filtering for 5 times; putting the obtained filtrate into ultrapure water, performing ultrasonic treatment for 3min, performing suction filtration, and repeating for 5 times; putting the obtained product into a 70 ℃ oven for drying for 6 hours; and (3) putting the dried product into a mortar, and grinding until the powder has no granular sensation to obtain the phenanthroline polymer.
And (3) testing molecular weight:
molecular weight measurement was performed on the phenanthroline polymer prepared in example 1 by gel chromatography, and the data were as follows: number average molecular weight 2797, weight average molecular weight 2902, Z average molecular weight 3015, and Z +1 average molecular weight 3134.
Example 2
Placing 1mol of 1, 10-phenanthroline monomer in a round-bottom flask, adding 160mL of acetonitrile, and performing ultrasonic treatment until the mixture is completely dissolved to obtain a solution with the concentration of 0.25 mol/L; preparing 0.25mol/L Ammonium Persulfate (APS) aqueous solution; slowly adding 40mLAPS aqueous solution into a flask, vacuumizing, introducing nitrogen for protection, starting a stirring switch, setting the stirring speed to be 550r/min, starting a heating switch, setting the oil bath temperature to be 70 ℃, carrying out oxidative polymerization for 15h, and keeping the device sealed; after the reaction is finished, cooling the obtained reaction system to room temperature, standing for 2 hours, filtering, putting the obtained filtrate into acetonitrile, and repeating ultrasonic ultrafiltration for 5 times; eluting the obtained filtrate in ultrapure water, performing ultrasonic treatment for 3min, vacuum filtering, and repeating ultrapure water elution-ultrasonic treatment-vacuum filtering for 5 times; putting the obtained filtrate into ultrapure water, performing ultrasonic treatment for 3min, performing suction filtration, and repeating for 5 times; putting the obtained product into a 70 ℃ oven for drying for 6 hours; and (3) putting the dried product into a mortar, and grinding until the powder has no granular sensation to obtain the phenanthroline polymer.
Number average molecular weight 1829, weight average molecular weight 1887, Z average molecular weight 1986, and Z +1 average molecular weight 2154.
Application example
Preparing Ag with initial concentrations of 20mg/L, 50mg/L, 100mg/L, 600mg/L, 1000mg/L and 1200mg/L respectively+Respectively taking 20mL of the solution, respectively putting 20mg of the phenanthroline polymer material prepared in the example 1 into a conical flask, putting the conical flask into a constant-temperature shaking box at the temperature of 25 ℃ and at the speed of 180r/min, reacting for 24 hours, respectively taking a small amount of solution after reaction after the reaction is finished, and detecting Ag in the solution by using a flame atomic absorption spectrophotometer+Concentration and calculating the adsorption quantity Q of the adsorbent at different initial concentrationseThe formula for calculating the adsorption capacity of the phenanthroline polymer is as follows:
in the formula: c0Ag in the initial solution+Concentration (mg/L);
Ceag in solution after adsorption+Concentration (mg/L);
Qe-phenanthroline polymer vs. Ag+Adsorption capacity (mg/g);
V-Ag+volume of solution (L);
mass (g) of W-phenanthroline polymer.
Study on Ag+The concentration of the solution is 0-1200 mg/L of phenanthroline polymer to Ag+The specific results are shown in table 1 and fig. 1.
TABLE 1Ag+Influence of initial concentration of solution on adsorption performance of phenanthroline polymer
| Initial concentration mg/L | Adsorption amount mg/g |
| 20 | 20.0 |
| 50 | 50.0 |
| 100 | 99.5 |
| 600 | 207.2 |
| 1000 | 234.6 |
| 1200 | 247.4 |
FIG. 1 shows Ag+The trend of the effect of the initial concentration of the solution on the adsorption capacity of the phenanthroline polymer is shown in Table 1 and FIG. 1, along with Ag+The initial concentration of the solution is increased, the adsorption capacity of the phenanthroline polymer to silver ions is increased, and the maximum adsorption is reached at 1200mg/LThe capacity, the maximum adsorption amount reaches 247.4mg/g and gradually becomes flat.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (3)
1. The preparation method of the phenanthroline polymer is characterized by comprising the following steps of:
mixing 1, 10-phenanthroline acetonitrile solution with an oxidant, and carrying out oxidative polymerization to obtain a phenanthroline polymer;
the oxidant is ammonium persulfate, the oxidant is used in the form of solution, and the concentration of the oxidant in the solution of the oxidant is 0.25 mol/L;
the molar ratio of the 1, 10-phenanthroline to the oxidant is (1-4) to 1;
in the acetonitrile solution of 1, 10-phenanthroline, the concentration of 1, 10-phenanthroline is 0.15-0.30 mol/L;
the temperature of the oxidative polymerization is 70-100 ℃, and the time is 3-15 h;
the oxidative polymerization is carried out under the conditions of stirring and nitrogen protection, and the stirring speed is 100-550 r/min;
after the oxidative polymerization is completed, the method further comprises the following steps: sequentially cooling, standing, separating, drying and grinding the obtained reaction system to obtain the phenanthroline polymer;
the structural unit of the prepared phenanthroline polymer is shown as a formula I:
2. The phenanthroline polymer produced by the production method according to claim 1.
3. The use of the phenanthroline polymer of claim 2 in adsorbing heavy metal ions in wastewater.
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| DE19757682A1 (en) * | 1997-12-23 | 1999-07-01 | Max Planck Gesellschaft | Application of alternating layers of oppositely charged polyelectrolyte by sequential adsorption |
| AU1022900A (en) * | 1999-11-05 | 2001-06-06 | Xijia Gu | Phosphorescent oxygen sensors |
| CN103214671A (en) * | 2013-05-07 | 2013-07-24 | 华东交通大学 | Chemical oxidation preparation method for novel N-substituted carboxyl polyaniline |
| KR20140117761A (en) * | 2013-03-26 | 2014-10-08 | 한양대학교 산학협력단 | Compound comprising polymer electrolyte membrane and preparation method thereof |
| CN105753861A (en) * | 2016-02-04 | 2016-07-13 | 浙江大学 | Phenanthroline derivative, and preparation method and application thereof |
| CN105906759A (en) * | 2016-07-02 | 2016-08-31 | 云南健牛生物科技有限公司 | Functional polymer microsphere, synthesis preparation method and application thereof |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19757682A1 (en) * | 1997-12-23 | 1999-07-01 | Max Planck Gesellschaft | Application of alternating layers of oppositely charged polyelectrolyte by sequential adsorption |
| AU1022900A (en) * | 1999-11-05 | 2001-06-06 | Xijia Gu | Phosphorescent oxygen sensors |
| KR20140117761A (en) * | 2013-03-26 | 2014-10-08 | 한양대학교 산학협력단 | Compound comprising polymer electrolyte membrane and preparation method thereof |
| CN103214671A (en) * | 2013-05-07 | 2013-07-24 | 华东交通大学 | Chemical oxidation preparation method for novel N-substituted carboxyl polyaniline |
| CN105753861A (en) * | 2016-02-04 | 2016-07-13 | 浙江大学 | Phenanthroline derivative, and preparation method and application thereof |
| CN105906759A (en) * | 2016-07-02 | 2016-08-31 | 云南健牛生物科技有限公司 | Functional polymer microsphere, synthesis preparation method and application thereof |
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