CN107892733B - Heavy metal wastewater ion adsorption resin and preparation method thereof - Google Patents
Heavy metal wastewater ion adsorption resin and preparation method thereof Download PDFInfo
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- CN107892733B CN107892733B CN201711322929.6A CN201711322929A CN107892733B CN 107892733 B CN107892733 B CN 107892733B CN 201711322929 A CN201711322929 A CN 201711322929A CN 107892733 B CN107892733 B CN 107892733B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
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- B01J20/261—Synthetic macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
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Abstract
The invention discloses a preparation method of a heavy metal wastewater ion adsorption resin, which comprises the following steps: 1) mixing 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione and ethylene diamine tetraacetic acid in a solvent, stirring and reacting for 8-10 hours at room temperature, then distilling under reduced pressure at 40-50 ℃ to remove the solvent, 2) dissolving the product obtained in the step 1) and the tetra [4- (4-carboxyphenyl) phenyl ] ethylene in a high boiling point solvent, adding an initiator, carrying out polymerization reaction for 3-5 hours at 40-50 ℃, and then precipitating in water to obtain a resin; the invention also discloses the high-efficiency heavy metal ion adsorption resin prepared by the preparation method; the high-efficiency heavy metal ion adsorption resin disclosed by the invention has the advantages of good adsorption effect on heavy metal ions, low cost, large adsorption capacity and easiness in desorption.
Description
Technical Field
The invention belongs to the technical field of environmental protection, and particularly relates to a heavy metal wastewater ion adsorption resin and a preparation method thereof.
Background
In recent years, with the acceleration of global industrialization progress, environmental pollution is increasingly serious, and becomes a large barrier for hindering the development of human beings, wherein heavy metal ion pollution in water is a serious one of a plurality of environmental problems, which has great harm to human bodies, and can cause carcinogenesis, teratogenesis and chromosome mutation after entering the human bodies.
The existing methods for treating heavy metal ion wastewater comprise an ion exchange method, an electrochemical method, a membrane separation method, a chemical method and a biological method. The methods have the effect of removing heavy metal ions, but the equipment is complex, secondary pollution is caused, the operation cost is high, and the waste is difficult to treat. In the prior art, an adsorbing material is adopted to adsorb heavy metal ions, and the method is simple and effective and has ideal treatment effect. However, the adsorption materials on the market at present have the defects of lower adsorption capacity, poor reproducibility and high price.
Therefore, there is a need for an adsorbent material with good adsorption effect on heavy metal ions, low cost, large adsorption capacity and easy desorption.
Disclosure of Invention
The invention aims to solve the problems and provides the heavy metal wastewater ion adsorption resin and the preparation method thereof, the preparation method is simple and easy to implement, the requirement on equipment is not high, the raw materials are easy to obtain, the cost is low, the prepared heavy metal adsorption resin has excellent mechanical property, the adsorption effect on heavy metal ions is good, the cost is low, the adsorption capacity is large, and desorption is easy.
In order to achieve the above object, the present invention provides the following technical solution, a preparation method of a heavy metal wastewater ion adsorption resin, comprising the following steps:
1) preparation of a polymerizable monomer: mixing 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione and ethylenediamine tetraacetic acid in a solvent, stirring and reacting for 8-10 hours at room temperature, and then distilling under reduced pressure at 40-50 ℃ to remove the solvent;
2) preparation of resin: dissolving the polymerized monomer prepared in the step 1) and tetra [4- (4-carboxyphenyl) phenyl ] ethylene in a high-boiling-point solvent, adding an initiator, carrying out polymerization reaction for 3-5 hours at the temperature of 40-50 ℃, and then precipitating in water to obtain resin;
wherein, the mass ratio of the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, the ethylene diamine tetraacetic acid and the solvent in the step 1) is (1.2-2) to (1) (3-5);
the solvent is selected from one or more of isopropanol, ethanol and dichloromethane;
the mass ratio of the polymerization type monomer, the tetra [4- (4-carboxyphenyl) phenyl ] ethylene, the high-boiling-point solvent and the initiator in the step 2) is (3-5): (1-2): (10-15): (0.03-0.05);
the high boiling point solvent is selected from one or more of dimethyl sulfoxide, N-dimethylformamide and N-methylpyrrolidone;
the initiator is selected from one or more of azobisisobutyronitrile and azobisisoheptonitrile;
the heavy metal wastewater ion adsorption resin is prepared by adopting the preparation method of the high-efficiency heavy metal ion adsorption resin.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
(1) the preparation method of the high-efficiency heavy metal ion adsorption resin provided by the invention is simple and easy to implement, has low requirements on equipment, easily available raw materials and low price.
(2) The high-efficiency heavy metal ion adsorption resin provided by the invention has the advantages that through chemical modification, the molecular chain is rich in carboxyl, hydroxyl, amino and other groups, the adsorption capacity for heavy metal ions is greatly improved, the desorption capacity is strong, and the high-efficiency heavy metal ion adsorption resin can be repeatedly used for a plurality of times.
(3) The high-efficiency heavy metal ion adsorption resin provided by the invention has the advantages that the molecular main chain adopts tetra [4- (4-carboxyphenyl) phenyl ] ethylene as one of the polymerization monomers and contains a larger aromatic ring structure, so that the membrane has good mechanical properties and chemical stability while maintaining high-efficiency adsorption.
(4) The molecular chain of the high-efficiency heavy metal ion adsorption resin provided by the invention contains a conjugated structure, and the high-efficiency heavy metal ion adsorption resin has visible light catalysis effect while maintaining high-efficiency adsorption, so that other organic pollutants in sewage are effectively treated.
Detailed Description
In order to make the technical solution of the present invention better understood by those skilled in the art, the following provides a detailed description of the product of the present invention with reference to the examples.
Example 1
A preparation method of a heavy metal wastewater ion adsorption resin comprises the following steps:
1) preparation of a polymerizable monomer: mixing 120g of 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione and 100g of ethylenediamine tetraacetic acid in 300g of isopropanol, reacting the mixture with stirring at room temperature for 8 hours, and distilling the mixture at 40 ℃ under reduced pressure to remove the solvent;
2) preparation of resin: dissolving 90g of the polymeric monomer prepared in the step 1) and 30g of tetra [4- (4-carboxyphenyl) phenyl ] ethylene in 300g of dimethyl sulfoxide, adding 0.9g of azobisisobutyronitrile, carrying out polymerization reaction for 3 hours at 40 ℃, and then precipitating in water to obtain resin;
the heavy metal wastewater ion adsorption resin is prepared by adopting the preparation method of the high-efficiency heavy metal ion adsorption resin.
Example 2
A preparation method of a heavy metal wastewater ion adsorption resin comprises the following steps:
1) preparation of a polymerizable monomer: mixing 140g of 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione and 100g of ethylenediamine tetraacetic acid in 350g of ethanol, reacting the mixture with stirring at room temperature for 9 hours, and distilling the mixture at 45 ℃ under reduced pressure to remove the solvent;
2) preparation of resin: dissolving 110g of the polymeric monomer prepared in the step 1) and 40g of tetra [4- (4-carboxyphenyl) phenyl ] ethylene in 350g of N, N-dimethylformamide, adding 1.2g of azobisisoheptonitrile, carrying out polymerization reaction at 45 ℃ for 4 hours, and then precipitating in water to obtain resin;
the heavy metal wastewater ion adsorption resin is prepared by adopting the preparation method of the high-efficiency heavy metal ion adsorption resin.
Example 3
A preparation method of a heavy metal wastewater ion adsorption resin comprises the following steps:
1) preparation of a polymerizable monomer: mixing 180g of 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione and 100g of ethylenediaminetetraacetic acid in 400g of dichloromethane, reacting the mixture with stirring at room temperature for 9.5 hours, and distilling off the solvent at 47 ℃ under reduced pressure;
2) preparation of resin: dissolving 130g of the polymeric monomer prepared in the step 1) and 50g of tetra [4- (4-carboxyphenyl) phenyl ] ethylene in 400g of N-methylpyrrolidone, adding 1.3g of an initiator, carrying out polymerization reaction at 48 ℃ for 4.5 hours, and then precipitating in water to obtain resin;
the initiator is selected from a mixture formed by mixing azobisisobutyronitrile and azobisisoheptonitrile according to a mass ratio of 2: 1;
the heavy metal wastewater ion adsorption resin is prepared by adopting the preparation method of the high-efficiency heavy metal ion adsorption resin.
Example 4
A preparation method of a heavy metal wastewater ion adsorption resin comprises the following steps:
1) preparation of a polymerizable monomer: mixing 200g of 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione and 100g of ethylenediamine tetraacetic acid in 500g of isopropanol, reacting the mixture with stirring at room temperature for 10 hours, and distilling the mixture at 50 ℃ under reduced pressure to remove the solvent;
2) preparation of resin: dissolving 150g of the polymeric monomer prepared in the step 1) and 60g of tetra [4- (4-carboxyphenyl) phenyl ] ethylene in 450g of a high-boiling-point solvent, adding 1.5g of an initiator, carrying out polymerization reaction at 50 ℃ for 5 hours, and then precipitating in water to obtain resin;
the high-boiling-point solvent is a mixture formed by mixing N, N-dimethylformamide and N-methylpyrrolidone according to the mass ratio of 3: 7;
the initiator is selected from a mixture formed by mixing azodiisobutyronitrile and azodiisoheptonitrile according to a mass ratio of 5: 7;
the heavy metal wastewater ion adsorption resin is prepared by adopting the preparation method of the high-efficiency heavy metal ion adsorption resin.
Comparative example 1
Commercially available activated carbon granules;
the heavy metals prepared by the embodiment of the invention are as follows: the examples and comparative examples of the present invention were carried out by measuring the adsorption capacity of heavy metal ions by the following method: placing a certain mass of adsorption material in a conical flask with a plug, respectively adding a certain volume of heavy metal ion solution, vibrating in a constant-temperature oscillator at a constant temperature of 25 ℃ for a certain time, and calculating adsorption capacity according to the change of the concentration of heavy metal ions in the feed liquid; the concentration of heavy metal ions is measured by using a UV2450 type ultraviolet-visible spectrophotometer and calculated according to the adsorption capacity formula (1):
qeq-adsorption capacity of heavy metal ions, mg/g; cO-initial concentration of feed solution, mg/m L;
Ctconcentration of feed liquid at time t, mg/m L, VfVolume of feed solution, m L, weight of W-adsorbing material, g.
In this example, the desorption rate was measured by the following method: washing the adsorption material after adsorption balance with distilled water until no metal ions exist in the filtrate, then mixing with a certain volume of 2% sulfuric acid solution, oscillating for a certain time at constant temperature in a constant temperature oscillator, measuring the concentration of heavy metal ions in the solution, and calculating the desorption rate according to the formula (2):
wherein η represents the desorption rate, and C represents the concentration of metal ions in the eluate (mg. L)-1) V is the volume of the eluent (L), Q is the adsorption capacity of the membrane adsorbent before elution (mg. g)-1) And m is the mass (g) of the adsorbent.
This example selects Pb2+、Cu2+、Cd3+The adsorption capacity and desorption rate were determined and the test results are shown in table 1.
TABLE 1 test results of adsorption and desorption performances of inventive examples and comparative examples
As can be seen from table 1, compared with the traditional commercially available activated carbon particles, the high-efficiency heavy metal adsorption resin prepared in this example has high-efficiency adsorption and desorption properties for heavy metal ions.
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the invention in any manner; those of ordinary skill in the art can readily implement the present invention as described herein; however, those skilled in the art should appreciate that they can readily use the disclosed conception and specific embodiments as a basis for designing or modifying other structures for carrying out the same purposes of the present invention; meanwhile, any changes, modifications, and evolutions of the equivalent changes of the above embodiments according to the actual techniques of the present invention are still within the protection scope of the technical solution of the present invention.
Claims (5)
1. The preparation method of the heavy metal wastewater ion adsorption resin is characterized by comprising the following steps:
1) preparation of a polymerizable monomer: mixing 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione and ethylenediamine tetraacetic acid in a solvent, stirring and reacting for 8-10 hours at room temperature, and then distilling under reduced pressure at 40-50 ℃ to remove the solvent;
2) preparation of resin: dissolving the polymerized monomer prepared in the step 1) and tetra [4- (4-carboxyphenyl) phenyl ] ethylene in a high-boiling-point solvent, adding an initiator, carrying out polymerization reaction for 3-5 hours at the temperature of 40-50 ℃, and then precipitating in water to obtain resin;
wherein, the mass ratio of the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, the ethylene diamine tetraacetic acid and the solvent in the step 1) is (1.2-2) to (1) (3-5);
the mass ratio of the polymerization type monomer, the tetra [4- (4-carboxyphenyl) phenyl ] ethylene, the high-boiling-point solvent and the initiator in the step 2) is (3-5): (1-2): (10-15): (0.03-0.05).
2. The method for preparing the heavy metal wastewater ion adsorption resin according to claim 1, wherein the solvent is one or more selected from isopropanol, ethanol and dichloromethane.
3. The method for preparing the heavy metal wastewater ion adsorption resin according to claim 1, wherein the high boiling point solvent is one or more selected from dimethylsulfoxide, N-dimethylformamide and N-methylpyrrolidone.
4. The method for preparing the heavy metal wastewater ion adsorption resin of claim 1, wherein the initiator is one or more selected from azobisisobutyronitrile and azobisisoheptonitrile.
5. The heavy metal wastewater ion adsorption resin is characterized by being prepared by the preparation method of the high-efficiency heavy metal ion adsorption resin according to any one of claims 1 to 4.
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| CN112480316A (en) * | 2018-05-23 | 2021-03-12 | 湖南辰砾新材料有限公司 | Cyclodextrin-based cucurbituril triazine copolymer and application thereof |
| CN109225155A (en) * | 2018-10-26 | 2019-01-18 | 浙江海洋大学 | A kind of preparation method of the superior adsorbent for cerium ion recycling |
| CN109534528B (en) * | 2018-11-20 | 2021-11-12 | 新昌县泰如科技有限公司 | Method for treating ciprofibrate process wastewater |
| CN110885394B (en) * | 2019-12-17 | 2022-03-11 | 万华化学集团股份有限公司 | Triazine group modified macroporous resin and preparation method thereof |
| CN115181213A (en) * | 2021-08-18 | 2022-10-14 | 深圳市康益保健用品有限公司 | Polymer for adsorbing metal ions and application thereof |
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| CN101173019A (en) * | 2006-10-31 | 2008-05-07 | 广州市纳森化工有限公司 | Method for synthesizing polymer chelating agent with polyvinyl alcohol as base chain |
| CN101885797A (en) * | 2010-07-09 | 2010-11-17 | 浙江大学 | A kind of functional polymer and its preparation method and application |
| CN104511274A (en) * | 2014-06-27 | 2015-04-15 | 济南大学 | Preparation method of supported resin for heavy metal ion adsorption |
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| CN101173019A (en) * | 2006-10-31 | 2008-05-07 | 广州市纳森化工有限公司 | Method for synthesizing polymer chelating agent with polyvinyl alcohol as base chain |
| CN101885797A (en) * | 2010-07-09 | 2010-11-17 | 浙江大学 | A kind of functional polymer and its preparation method and application |
| CN104511274A (en) * | 2014-06-27 | 2015-04-15 | 济南大学 | Preparation method of supported resin for heavy metal ion adsorption |
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