CN109675534B - Waste plastic-based super-crosslinked polymer with adjustable pore diameter and preparation method and application thereof - Google Patents
Waste plastic-based super-crosslinked polymer with adjustable pore diameter and preparation method and application thereof Download PDFInfo
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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- C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
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Abstract
The invention provides a preparation method of a waste plastic-based hypercrosslinked polymer with adjustable aperture, which comprises the following steps: mixing the polystyrene foamed plastic with 1, 2-dichloroethane and methylal, fully dissolving, adding anhydrous ferric chloride for catalysis to perform one-step crosslinking reaction or performing secondary crosslinking after pre-crosslinking by using acetic acid and methylal, and purifying to obtain the super-crosslinked polymer with adjustable pore diameter and high specific surface area. Compared with molecular sieves, zeolite and various commercial activated carbons used in the market, the hypercrosslinked polymer prepared by the preparation method has the advantages of obvious removal effect and low cost; the preparation method provided by the invention has mild process, changes waste polystyrene foamed plastics into valuables, effectively solves the problem of environmental pollution caused by the waste plastics, and has good market application prospect.
Description
Technical Field
The invention relates to the technical field of super-crosslinked polymers, in particular to a waste plastic-based super-crosslinked polymer with adjustable aperture and a preparation method and application thereof.
Background
The polystyrene foamed plastic is a polystyrene with a linear structure, has excellent mechanical and insulating properties, and is a large amount of high polymer materials used for preparing resin molded articles. Waste polystyrene is converted into a material with high added value, and the problem of environmental pollution caused by solid waste can be solved to a certain extent. Therefore, the research for changing waste polystyrene into valuable has been the research focus of researchers. The polystyrene foamed plastic is a porous material, is mainly prepared into hollow carbon and carbon film materials by using polystyrene as a template agent, or is prepared into various carbon materials by direct carbonization, composite carbonization with other substances and catalytic carbonization, and is widely applied to the fields of adsorption, catalysis, batteries and the like. However, during the carbonization of polystyrene, some intermediates are obtained, which are mostly Polycyclic Aromatic Hydrocarbons (PAHs), and are reported as potential carcinogenic substances. In addition, the polystyrene-based porous activated carbon material is difficult to efficiently remove organic pollutant molecules with different sizes, and cannot solve the problem that the water pollutes the environment increasingly seriously at present. Therefore, the polystyrene-based porous material prepared by the traditional method cannot adapt to and meet the requirements of production and practical application.
Disclosure of Invention
In view of the above, the invention provides a preparation method of a waste plastic-based hypercrosslinked polymer with adjustable pore size, which has a simple process, the hypercrosslinked polymer has adjustable pore size and a high specific surface area, and can be used for efficiently removing organic pollutant molecules with different sizes in a water body.
The invention provides a preparation method of a waste plastic-based hypercrosslinked polymer with adjustable aperture, which comprises the following steps:
s1, mixing the polystyrene foaming plastic with 1, 2-dichloroethane and methylal, adding anhydrous ferric chloride for crosslinking reaction after fully dissolving, and cooling to room temperature.
S2, washing, carrying out Soxhlet extraction and drying to obtain the super-crosslinked polymer.
Further, the polystyrene foamed plastic is selected from waste polystyrene foamed plastic.
Further, the mass ratio of the polystyrene foamed plastic to the anhydrous ferric chloride is 1:4-1:10, and the mass ratio of the polystyrene foamed plastic to the methylal is 1: 10.
Further, in the step (b), the reaction temperature of the crosslinking reaction is 80 ℃ and the time is 12 h.
Further, in step S2, the washing process is: washed 3 times with acetone, dilute hydrochloric acid and water, respectively.
Further, in step S2, the soxhlet extraction process is performed for 24h with methanol.
Further, in step S2, the drying process is drying under vacuum for 12 h.
Further, before the crosslinking reaction, the polystyrene foamed plastic is subjected to pre-crosslinking treatment, so that the hypercrosslinked polymers with different pore diameters can be obtained, wherein the pre-crosslinking treatment process comprises the following steps: mixing the polystyrene foamed plastic with acetic acid and methylal, adding anhydrous ferric chloride for pre-crosslinking reaction after fully dissolving, purifying, and performing crosslinking reaction on the purified substances to obtain the hypercrosslinked polymers with different pore diameters.
Furthermore, the adsorption capacity of the waste plastic-based hypercrosslinked polymer with adjustable pore diameter to tetracycline is 152.21-621.12mg g-1。
The waste plastic based hypercrosslinked polymer provided by the invention is prepared from polystyrene foaming plastic.
The invention also provides application of the waste plastic-based super-crosslinked polymer, and the super-crosslinked polymer can be used for efficiently removing organic pollutant molecules with different sizes in a water body.
The technical scheme provided by the invention has the beneficial effects that: the preparation method provided by the invention can be used for obtaining the super-crosslinked polymer with adjustable pore diameter and higher specific surface area through one-step crosslinking and gradual crosslinking; compared with molecular sieves, zeolite and various commercial activated carbons used in the market, the hypercrosslinked polymer prepared by the preparation method has the advantages of obvious removal effect and low cost; the preparation method provided by the invention has mild process, changes waste polystyrene foamed plastics into valuables, effectively solves the problem of environmental pollution caused by the waste plastics, and has good market application prospect.
Drawings
FIG. 1 is a schematic flow chart of the process for preparing the hypercrosslinked polymer EPS-FDA-2 of example 1 of the present invention.
FIG. 2 is a comparison of the adsorption performance of the hypercrosslinked polymer EPS-FDA-2 prepared in example 1 of the present invention with various commercial activated carbons.
FIG. 3 is a schematic flow chart of the process for preparing the hypercrosslinked polymer EPS-FDA-1 of example 2 of the present invention.
FIG. 4 is an SEM image of the polystyrene foam of the invention, the super-crosslinked polymer EPS-FDA-2 and the super-crosslinked polymer EPS-FDA-1.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, embodiments of the present invention will be further described with reference to the accompanying drawings.
The embodiment of the invention provides a preparation method of a waste plastic-based hypercrosslinked polymer with adjustable aperture, which comprises the following steps:
mixing polystyrene foamed plastic with a solvent 1, 2-dichloroethane and a cross-linking agent methylal, adding a catalyst anhydrous ferric chloride to perform cross-linking reaction for 12 hours at the temperature of 80 ℃, respectively washing with acetone, diluted hydrochloric acid and water for 3 times when a reaction system is cooled to room temperature, performing Soxhlet extraction for 24 hours with methanol, and performing vacuum drying for 12 hours to obtain a super cross-linked polymer; the polystyrene foamed plastic is selected from waste polystyrene foamed plastic; the mass ratio of the polystyrene foaming plastic to the anhydrous ferric chloride is 1:4-1:10, and the mass ratio of the polystyrene foaming plastic to the methylal is 1: 10.
In the above process, if the polystyrene foamed plastic is pre-crosslinked, the hypercrosslinked polymers with different pore diameters can be obtained, and the pre-crosslinking process is as follows: mixing polystyrene foamed plastic with acetic acid and methylal, adding anhydrous ferric chloride for pre-crosslinking reaction for 1h after fully dissolving, purifying, mixing the purified substance with 1, 2-dichloroethane and methylal, fully dissolving, adding anhydrous ferric chloride for crosslinking reaction for 12h at 80 ℃, respectively washing with acetone, dilute hydrochloric acid and water for 3 times after the reaction system is cooled to room temperature, performing Soxhlet extraction with methanol for 24h, and vacuum drying for 12h to obtain the hypercrosslinked polymer with different pore size distributions.
The super-crosslinked polymer prepared by the invention is prepared by taking a Friedel-crafts alkylation reaction as a principle and utilizing a crosslinking agent in a reaction formula to perform a Friedel-crafts alkylation reaction with polystyrene in the presence of a Lewis acid catalyst. In the preparation method, corresponding production processes can be added according to the related requirements of removing by-products and purifying products and the like.
The reaction formula of the preparation method is as follows:
the present invention provides a waste plastic based hypercrosslinked polymer with adjustable pore diameter and a method for preparing the same.
Example 1: 0.5006g of Polystyrene foamed plastic (EPS) is weighed and dissolved in a mixed solution of 40mL of acetic acid and 5.6mL of methylal at room temperature, and then 2.23g of anhydrous ferric chloride is added; the system is subjected to pre-crosslinking reaction for 1h at 80 ℃, and then is subjected to purification treatment to obtain a secondary crosslinking precursor; adding a mixed solution of 1 mL, 2-dichloroethane and 5.6mL of methylal into the obtained precursor, then adding 10g of anhydrous ferric chloride for secondary crosslinking, respectively washing with acetone, diluted hydrochloric acid and water for 3 times when the reaction system is cooled to room temperature, then performing Soxhlet extraction with methanol for 24h, and performing vacuum drying for 12h to obtain the super-crosslinked polymer EPS-FDA-2.
The preparation process of example 1 of the present invention is shown in FIG. 1.
The comparison result of the adsorption performance of the super-crosslinked polymer EPS-FDA-2 prepared in example 1 of the present invention with various commercial activated carbons is shown in FIG. 2, and it can be seen from FIG. 2 that the super-crosslinked polymer EPS-FDA-2 of the present invention has excellent adsorption performance on tetracycline, which is higher than that of various activated carbons.
The preparation cost of the hypercrosslinked polymer EPS-FDA-2 prepared in example 1 of the present invention is compared with that of various commercial activated carbons in Table 1.
Table 1: comparison of preparation costs of the hypercrosslinked Polymer EPS-FDA-2 with various commercial activated carbons
As can be seen from Table 1, the hypercrosslinked polymer EPS-FDA-2 of example 1 of the present invention is produced at a low cost, and the estimated price is higher than that of ordinary activated carbon having poor adsorption property, but is much lower than that of commercially available high-performance activated carbon, which is only half of the price.
Example 2:
0.5006g of Polystyrene foamed plastic (Expandable Polystyrene; EPS) is weighed and dissolved in 40mL of mixed solution of 1, 2-dichloroethane and 5.6mL of methylal at room temperature, and then 2.23g of anhydrous ferric chloride is added; the system is subjected to crosslinking reaction at 80 ℃ for 12h, after the reaction system is cooled to room temperature, acetone, dilute hydrochloric acid and water are respectively used for washing for 3 times, then methanol is used for Soxhlet extraction for 24h, and vacuum drying is carried out for 12h, so that the super-crosslinked polymer EPS-FDA-1 is obtained.
The procedure for the preparation of example 2 of the present invention is shown in FIG. 3.
The specific surface area and pore size distribution parameters of the hypercrosslinked polymer EPS-FDA-2 prepared in example 1 of the present invention and the hypercrosslinked polymer EPS-FDA-1 prepared in example 2 are shown in Table 2.
Table 2: specific surface area and pore size distribution parameters of the hypercrosslinked Polymer EPS-FDA-2 and the hypercrosslinked Polymer EPS-FDA-1
As can be seen from Table 2, the hypercrosslinked polymer EPS-FDA-2 prepared in example 1 of the present invention and the hypercrosslinked polymer EPS-FDA-1 prepared in example 2 both have a high specific surface area.
The comparison of the adsorption performance of the super-crosslinked polymer EPS-FDA-2 prepared in the embodiment 1 of the invention and the super-crosslinked polymer EPS-FDA-1 in the embodiment 2 with that of tetracycline (tetracycline) reported in various documents is shown in Table 3.
Table 3: comparison of adsorption Properties of the hypercrosslinked Polymer EPS-FDA-2 and the hypercrosslinked Polymer EPS-FDA-1 with various literature reported materials
As can be seen from Table 3, the adsorption amount of tetracycline by the hypercrosslinked polymer EPS-FDA prepared in example 1 of the present invention at-225 ℃ was 621.12mg g-1The adsorption amount of the hypercrosslinked polymer EPS-FDA prepared in example 2 to tetracycline at 125 ℃ was 310.60mg g-1All far exceeding other materials.
SEM (Scanning Electron Microscope) images of the polystyrene foamed plastics used in examples 1 and 2 of the present invention, which are derived from waste plastics in the laboratory, the raw polystyrene foamed plastics, the super crosslinked polymer EPS-FDA-2, and the super crosslinked polymer EPS-FDA-1 are shown in FIG. 4, FIG. 4a is an SEM image of a raw material polystyrene foamed plastic, FIG. 4b is an SEM image of a hypercrosslinked polymer EPS-FDA-2, FIG. 4c is an SEM image of the super crosslinked polymer EPS-FDA-1. As can be seen from FIG. 4, the super crosslinked polymer EPS-FDA-2 has a layered pore structure with uniform pore size distribution, and a certain structure of the polystyrene foaming plastic is reserved, the EPS-FDA-1 has a pore size obviously smaller than that of EPS-FDA-2, but has a pore volume larger than that of EPS-FDA-2.
5mg of the hypercrosslinked polymer EPS-FDA-2 from example 1 and 5mg of the EPS-FDA-1 from example 2 were each placed in a 40mL concentration of 20 mg. multidot.L-1In the tetracycline solution, the pH value range of the tetracycline solution is 3-10, and the absorbance of the adsorbed solution is measured by an ultraviolet visible spectrophotometer, and the maximum absorption wavelength of the tetracycline is 358 nm;
the mass concentrations are respectively 40, 60, 80, 100 and 200 mg.L-1The absorbance of the tetracycline at 358nm is measured by ultraviolet visible spectrophotometer to establish a standard curve between the absorbance and the concentration, namely Y is 0.03275X-0.002 (Y: absorbance; X: tetracycline concentration, unit is mg.L)-1) (ii) a The calculation formula of the equilibrium adsorption amount is as follows: q. q.se＝((C0-Ce)V)/m(qeFor equilibrium adsorption, the unit is mg.g-1；C0、 CeThe initial concentration and the equilibrium concentration of tetracycline are respectively expressed in mg.L-1(ii) a V is the volume of the solution inL; m is the mass of the adsorbent used, in mg);
experiments prove that the super-crosslinked polymers EPS-FDA-1 and EPS-FDA-2 have the best adsorption effect when the pH is 6; and in the range of 40-500 mg.L-1Respectively adding 5mg of the super-crosslinked polymers EPS-FDA-1 and EPS-FDA-2 into the tetracycline solution, and obtaining the super-crosslinked polymers EPS-FDA-1 and EPS-FDA-2 with the adsorption capacity of 152.21-621.12mg g for tetracycline after adsorption balance at room temperature-1。
The features of the embodiments and embodiments described herein above may be combined with each other without conflict.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (4)
1. A preparation method of waste plastic-based hypercrosslinked polymer with adjustable aperture is characterized by comprising the following steps: mixing polystyrene foamed plastic with acetic acid and methylal, adding anhydrous ferric chloride for pre-crosslinking reaction for 1h after fully dissolving, purifying, mixing the purified substance with 1, 2-dichloroethane and methylal, adding anhydrous ferric chloride for crosslinking reaction for 12h at 80 ℃ after fully dissolving, cooling to room temperature, washing for 3 times by using acetone, dilute hydrochloric acid and water respectively, then performing soxhlet extraction for 24h by using methanol, and drying for 12h under vacuum to obtain a super-crosslinked polymer; the structural formula of the hypercrosslinked polymer is
Wherein the polystyrene foamed plastic is selected from waste polystyrene foamed plastic; the mass ratio of the polystyrene foamed plastic to the anhydrous ferric chloride is 1:4-1:10, and the mass ratio of the polystyrene foamed plastic to the methylal is 1: 10.
2. A waste plastic-based hypercrosslinked polymer having an adjustable pore size, characterized by being produced by the production method of claim 1.
3. The waste plastic-based hypercrosslinked polymer with adjustable pore size as claimed in claim 2, wherein the adsorption capacity of the hypercrosslinked polymer for tetracycline is 152.21-621.12 mg-g-1。
4. Use of the adjustable pore size waste plastic-based hypercrosslinked polymer as claimed in claim 2, wherein the hypercrosslinked polymer can be used for removing organic contaminant molecules of different sizes in water.
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| "sorption of tetracycline antibiotics on hyper-crosslinked polystyrene from aqueous and aqueous-organic media";Udalova A. Yu;《RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A》;20150514;第89卷(第6期);摘要 * |
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