CN113976185B - Preparation method of macroporous anion exchange resin for water treatment - Google Patents
Preparation method of macroporous anion exchange resin for water treatment Download PDFInfo
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- CN113976185B CN113976185B CN202111247811.8A CN202111247811A CN113976185B CN 113976185 B CN113976185 B CN 113976185B CN 202111247811 A CN202111247811 A CN 202111247811A CN 113976185 B CN113976185 B CN 113976185B
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/12—Macromolecular compounds
- B01J41/14—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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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
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
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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
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
- C02F2001/422—Treatment of water, waste water, or sewage by ion-exchange using anionic exchangers
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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
- C02F2101/30—Organic compounds
- C02F2101/40—Organic compounds containing sulfur
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Abstract
The invention discloses a preparation method of macroporous anion exchange resin for water treatment, which relates to the technical field of anion exchange resin.
Description
Technical field:
the invention relates to the technical field of anion exchange resins, in particular to a preparation method of a macroporous anion exchange resin for water treatment.
The background technology is as follows:
the anion exchange resin refers to an ion exchange resin containing alkaline groups in molecules, has alkalinity in a solution, can exchange anions in the solution by using hydroxyl ions, can be divided into three types of strong alkalinity, weak alkalinity and strong and weak alkalinity mixtures, and is used for removing harmful anions (such as cyanide ions, thiocyanate ions and the like) in wastewater of water treatment (including hard water softening, high-pressure boiler water, deionized water, injection water, seawater desalination and the like), extracting rare elements, separating amino acids, vitamin C, tartaric acid, citric acid and the like.
The aromatic sulfonic acid compound is an important fine chemical product, is an indispensable raw material in the chemical industry, but because the production process is long, the side reaction is more, the water solubility is strong, waste water with complex components and higher concentration is easily generated in the production process, and in addition, the reduction product of the azo dye also contains a large amount of aromatic sulfonic acid compound. However, the biodegradability of the aromatic sulfonic acid compounds is poor, the high water solubility and the strong polarity thereof make it difficult to effectively treat the wastewater rich in the aromatic sulfonic acid compounds by using a flocculation method, an extraction method and an adsorption method which are conventional in the art, and the wastewater has the following main characteristics: (1) high contaminant concentration; (2) strong acidity; (3) deep color; (4) difficult biodegradation.
Chai Limin in "study of macroporous weakly basic anion exchange resin D301R for treating DSD acid reduction wastewater" the ion exchange resin method is adopted for treatmentDSD acid reduces wastewater and systematic studies of this process were performed. The macroporous weak-alkaline anion exchange resin D301R is determined by resin selection, and the removal rate of the macroporous weak-alkaline anion exchange resin D301R on the wastewater CODcr can reach 74.7 percent. Thermodynamic experiment researches are carried out on the adsorption and exchange of the DSD acid reduction wastewater by D301R under the influence of various factors, and the influence of time, temperature, pH value, salt content and the like on the process is respectively examined. Experimental results show that the adsorption equilibrium time of the ion exchange resin on DSD acid reduction wastewater is 6h, the adsorption exchange process is an exothermic process, the higher the temperature is, the lower the resin adsorption exchange amount is, and the low temperature is favorable for the resin adsorption exchange reaction; the high pH value is favorable for adsorption exchange; the effect of salt content on the process is mainly from the large amount of SO in the wastewater 4 2- Competitive exchange of ions. Although this document conducted systematic studies on the treatment of DSD acid reduction wastewater with macroporous weakly basic anion exchange resin D301R, the treatment effect and treatment period were still to be optimized.
The invention comprises the following steps:
the invention aims to provide a preparation method of macroporous anion exchange resin for water treatment, which is used for preparing the macroporous anion exchange resin by suspension polymerization reaction, chloromethylation reaction and amination reaction in sequence, wherein the macroporous anion exchange resin has good treatment effect on aromatic sulfonic acid compound wastewater, has good reproducibility and can be recycled.
The technical problems to be solved by the invention are realized by adopting the following technical scheme:
the invention aims to provide a preparation method of macroporous anion exchange resin for water treatment, which comprises the following preparation steps:
(1) Adding a dispersing agent, sodium chloride and methylene blue into water, heating and stirring to completely dissolve the dispersing agent, and cooling to obtain a water phase; then adding an oil phase consisting of styrene, a cross-linking agent, a pore-forming agent and an initiator into the water phase, heating to react, stopping the reaction, alternately washing the obtained white balls with hot water and ethanol until the liquid is clear, and drying to obtain polystyrene cross-linked microspheres;
(2) Swelling the polystyrene crosslinking microsphere obtained in the step (1) in chloromethyl ether, adding a catalyst, heating to perform chloromethylation reaction, washing with water, and drying to obtain chloromethylation polystyrene crosslinking microsphere;
(3) Swelling the chloromethylated polystyrene crosslinking microsphere prepared in the step (2) in dioxane, then adding triethylamine, heating for amination reaction, washing with water, and drying to obtain macroporous anion exchange resin.
The cross-linking agent is diallyl n-propyl isocyanurate.
Styrene-divinylbenzene microspheres are generally prepared in the art by using divinylbenzene as a crosslinking agent, and then the anion exchange resin is prepared through chloromethylation and amination. Even for the purpose of optimizing the adsorptivity of the anion exchange resin or enhancing the specificity of the anion exchange resin, the adjustment is generally made only in the choice of the amination agent, and thus the application performance of the anion exchange resin is limited. Starting from the cross-linking agent, the invention adopts diallyl n-propyl isocyanurate to replace divinylbenzene as the cross-linking agent, and is expected to prepare the macroporous anion exchange resin special for the wastewater treatment of aromatic sulfonic acid compounds.
The dispersing agent is polyvinyl alcohol or gelatin.
The pore-forming agent is isobutanol, and the initiator is benzoyl peroxide.
The dispersing agent is used in an amount of 0.5-1.5% of the water phase, the sodium chloride is used in an amount of 0.05-0.1% of the water phase, and the methylene blue is used in an amount of 0.01-0.05% of the water phase.
The usage amount of the cross-linking agent is 10-20% of the mass of the styrene, the usage amount of the pore-forming agent is 50-100% of the total mass of the styrene and the cross-linking agent, the usage amount of the initiator is 0.5-1% of the total mass of the styrene and the cross-linking agent, and the volume ratio of the water phase to the oil phase is (1-3): 1.
The catalyst is anhydrous ferric chloride or anhydrous zinc chloride.
The dosage of the catalyst is 20-50% of the mass of the polystyrene crosslinking microsphere.
The dosage of the triethylamine is 5-15% of the mass of the chloromethylated polystyrene crosslinking microsphere.
The invention also aims to provide the application of the macroporous anion exchange resin prepared by the method in the treatment of the aromatic sulfonic acid compound wastewater.
In terms of molecular structure, diallyl n-propyl isocyanurate and divinylbenzene are not compounds with similar structures, so that the prior art adopting divinylbenzene as a cross-linking agent in the field cannot give technical suggestion of replacing the diallyl n-propyl isocyanurate with the divinylbenzene, and in other cases, the macroporous anion exchange resin prepared by the application is specially used for treating wastewater of aromatic sulfonic acid compounds, and selectively adsorbs the aromatic sulfonic acid compounds, thereby efficiently removing the aromatic sulfonic acid compounds in the wastewater.
The beneficial effects of the invention are as follows: the macroporous anion exchange resin with a novel molecular structure is prepared through suspension polymerization reaction, chloromethylation reaction and amination reaction, and has good affinity to aromatic sulfonic acid compounds and strong adsorption selectivity, so that the macroporous anion exchange resin has excellent treatment effect on aromatic sulfonic acid compound wastewater, is not limited by the pH value of the wastewater, has good reproducibility, and can be recycled by regenerating the desorbed numerical value with sodium hydroxide solution.
The specific embodiment is as follows:
the invention is further described in connection with the following embodiments in order to make the technical means, the creation features, the achievement of the purpose and the effect of the invention easy to understand.
Example 1
(1) Adding gelatin, sodium chloride and methylene blue into water, heating and stirring to completely dissolve a dispersing agent, and cooling to obtain a water phase, wherein the dosage of the dispersing agent is 1.5% of the mass of the water phase, the dosage of the sodium chloride is 0.05% of the mass of the water phase, and the dosage of the methylene blue is 0.02% of the mass of the water phase; then adding an oil phase consisting of styrene, diallyl n-propyl isocyanurate, isobutanol and benzoyl peroxide into the water phase, wherein the dosage of the diallyl n-propyl isocyanurate is 15% of the mass of the styrene, the dosage of the isobutanol is 100% of the total mass of the styrene and the cross-linking agent, the dosage of the benzoyl peroxide is 0.5% of the total mass of the styrene and the diallyl n-propyl isocyanurate, the volume ratio of the water phase to the oil phase is 2:1, heating to 80 ℃ for reacting for 8 hours, stopping the reaction, and alternately washing the obtained white balls with hot water and ethanol until the liquid is clear, and drying to obtain the polystyrene cross-linked microspheres.
(2) Swelling the polystyrene crosslinking microsphere obtained in the step (1) in chloromethyl ether, adding anhydrous ferric chloride with the dosage of 35% of the mass of the polystyrene crosslinking microsphere, heating to 35 ℃ for chloromethylation reaction for 12h, washing with water, and drying to obtain the chloromethylation polystyrene crosslinking microsphere.
(3) Swelling the chloromethylated polystyrene crosslinking microsphere prepared in the step (2) in dioxane, then adding triethylamine with the dosage of 10% of the mass of the chloromethylated polystyrene crosslinking microsphere, heating to 50 ℃ for amination reaction for 8 hours, washing with water, and drying to obtain the macroporous anion exchange resin.
Example 2
(1) Adding gelatin, sodium chloride and methylene blue into water, heating and stirring to completely dissolve a dispersing agent, and cooling to obtain a water phase, wherein the dosage of the dispersing agent is 1% of the mass of the water phase, the dosage of the sodium chloride is 0.1% of the mass of the water phase, and the dosage of the methylene blue is 0.03% of the mass of the water phase; then adding an oil phase consisting of styrene, diallyl n-propyl isocyanurate, isobutanol and benzoyl peroxide into the water phase, wherein the dosage of the diallyl n-propyl isocyanurate is 10% of the mass of the styrene, the dosage of the isobutanol is 50% of the total mass of the styrene and the cross-linking agent, the dosage of the benzoyl peroxide is 1% of the total mass of the styrene and the diallyl n-propyl isocyanurate, the volume ratio of the water phase to the oil phase is 3:1, heating to 80 ℃ for reacting for 8 hours, stopping the reaction, and alternately washing the obtained white balls with hot water and ethanol until the liquid is clarified, and drying to obtain the polystyrene cross-linked microspheres.
(2) Swelling the polystyrene crosslinking microsphere obtained in the step (1) in chloromethyl ether, adding anhydrous zinc chloride with the dosage of 25% of the mass of the polystyrene crosslinking microsphere, heating to 35 ℃ for chloromethylation reaction for 12h, washing with water, and drying to obtain the chloromethylation polystyrene crosslinking microsphere.
(3) Swelling the chloromethylated polystyrene crosslinking microsphere prepared in the step (2) in dioxane, then adding triethylamine with the amount of 5% of the mass of the chloromethylated polystyrene crosslinking microsphere, heating to 50 ℃ for amination reaction for 8 hours, washing with water, and drying to obtain the macroporous anion exchange resin.
Example 3
(1) Adding polyvinyl alcohol, sodium chloride and methylene blue into water, heating and stirring to completely dissolve a dispersing agent, and cooling to obtain a water phase, wherein the dosage of the dispersing agent is 0.5% of the mass of the water phase, the dosage of the sodium chloride is 0.08% of the mass of the water phase, and the dosage of the methylene blue is 0.05% of the mass of the water phase; then adding an oil phase consisting of styrene, diallyl n-propyl isocyanurate, isobutanol and benzoyl peroxide into the water phase, wherein the dosage of the diallyl n-propyl isocyanurate is 20% of the mass of the styrene, the dosage of the isobutanol is 100% of the total mass of the styrene and the cross-linking agent, the dosage of the benzoyl peroxide is 0.5% of the total mass of the styrene and the diallyl n-propyl isocyanurate, the volume ratio of the water phase to the oil phase is 1:1, heating to 80 ℃ for reacting for 8 hours, stopping the reaction, and alternately washing the obtained white balls with hot water and ethanol until the liquid is clear, and drying to obtain the polystyrene cross-linked microspheres.
(2) Swelling the polystyrene crosslinking microsphere obtained in the step (1) in chloromethyl ether, adding anhydrous zinc chloride with the dosage of 20% of the mass of the polystyrene crosslinking microsphere, heating to 35 ℃ for chloromethylation reaction for 12h, washing with water, and drying to obtain the chloromethylation polystyrene crosslinking microsphere.
(3) Swelling the chloromethylated polystyrene crosslinking microsphere prepared in the step (2) in dioxane, then adding triethylamine with the amount of 15% of the mass of the chloromethylated polystyrene crosslinking microsphere, heating to 50 ℃ for amination reaction for 8 hours, washing with water, and drying to obtain the macroporous anion exchange resin.
Example 4
(1) Adding polyvinyl alcohol, sodium chloride and methylene blue into water, heating and stirring to completely dissolve a dispersing agent, and cooling to obtain a water phase, wherein the dosage of the dispersing agent is 1% of the mass of the water phase, the dosage of the sodium chloride is 0.1% of the mass of the water phase, and the dosage of the methylene blue is 0.01% of the mass of the water phase; then adding an oil phase consisting of styrene, diallyl n-propyl isocyanurate, isobutanol and benzoyl peroxide into the water phase, wherein the dosage of the diallyl n-propyl isocyanurate is 12% of the mass of the styrene, the dosage of the isobutanol is 50% of the total mass of the styrene and the cross-linking agent, the dosage of the benzoyl peroxide is 1% of the total mass of the styrene and the diallyl n-propyl isocyanurate, the volume ratio of the water phase to the oil phase is 2:1, heating to 80 ℃ for reacting for 8 hours, stopping the reaction, and alternately washing the obtained white balls with hot water and ethanol until the liquid is clarified, and drying to obtain the polystyrene cross-linked microspheres.
(2) Swelling the polystyrene crosslinking microsphere obtained in the step (1) in chloromethyl ether, adding anhydrous ferric chloride with the dosage of 50% of the mass of the polystyrene crosslinking microsphere, heating to 35 ℃ for chloromethylation reaction for 12h, washing with water, and drying to obtain the chloromethylation polystyrene crosslinking microsphere.
(3) Swelling the chloromethylated polystyrene crosslinking microsphere prepared in the step (2) in dioxane, then adding triethylamine with the dosage of 10% of the mass of the chloromethylated polystyrene crosslinking microsphere, heating to 50 ℃ for amination reaction for 8 hours, washing with water, and drying to obtain the macroporous anion exchange resin.
Example 5
(1) Adding gelatin, sodium chloride and methylene blue into water, heating and stirring to completely dissolve a dispersing agent, and cooling to obtain a water phase, wherein the dosage of the dispersing agent is 1% of the mass of the water phase, the dosage of the sodium chloride is 0.1% of the mass of the water phase, and the dosage of the methylene blue is 0.03% of the mass of the water phase; then adding an oil phase consisting of styrene, diallyl n-propyl isocyanurate, isobutanol and benzoyl peroxide into the water phase, wherein the dosage of the diallyl n-propyl isocyanurate is 15% of the mass of the styrene, the dosage of the isobutanol is 100% of the total mass of the styrene and the cross-linking agent, the dosage of the benzoyl peroxide is 0.5% of the total mass of the styrene and the diallyl n-propyl isocyanurate, the volume ratio of the water phase to the oil phase is 2:1, heating to 80 ℃ for reacting for 8 hours, stopping the reaction, and alternately washing the obtained white balls with hot water and ethanol until the liquid is clear, and drying to obtain the polystyrene cross-linked microspheres.
(2) Swelling the polystyrene crosslinking microsphere obtained in the step (1) in chloromethyl ether, adding anhydrous zinc chloride with the dosage of 30% of the mass of the polystyrene crosslinking microsphere, heating to 35 ℃ for chloromethylation reaction for 12h, washing with water, and drying to obtain the chloromethylation polystyrene crosslinking microsphere.
(3) Swelling the chloromethylated polystyrene crosslinking microsphere prepared in the step (2) in dioxane, then adding triethylamine with the amount of 12% of the mass of the chloromethylated polystyrene crosslinking microsphere, heating to 50 ℃ for amination reaction for 8 hours, washing with water, and drying to obtain the macroporous anion exchange resin.
Comparative example 1
Comparative example 1 was obtained by substituting divinylbenzene for diallyl n-propyl isocyanurate in step (3) of example 5, and the remaining procedure was unchanged.
Comparative example 2
Macroporous weak base anion exchange resin D301R is used.
200mL of a DSD sodium acid solution (DSD, chinese name 4, 4-diaminostilbene-2, 2-disulfonic acid) with a concentration of 1000mg/L, pH =7 was prepared, 0.1g of dried anion exchange resin was put in, and the solution was subjected to shaking adsorption at 25℃for 24 hours at a shaking frequency of 150rpm until the adsorption equilibrium was reached, and the concentration of the remaining DSD sodium acid in the solution was measured by HPLC method, and the adsorption capacity was calculated as shown in the following table.
From the above table, it can be seen that the modification of the crosslinking agent is beneficial to enhancing the adsorption effect of the anion exchange resin prepared in the example on sodium DSD, and the adsorption effect is obviously superior to that of the commercial macroporous weak basic anion exchange resin D301R.
The foregoing has shown and described the basic principles and main features of the present invention and the advantages of the present invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made without departing from the spirit and scope of the invention, which is defined in the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (9)
1. The preparation method of the macroporous anion exchange resin for water treatment is characterized by comprising the following preparation steps:
(1) Adding a dispersing agent, sodium chloride and methylene blue into water, heating and stirring to completely dissolve the dispersing agent, and cooling to obtain a water phase; then adding an oil phase consisting of styrene, a cross-linking agent, a pore-forming agent and an initiator into the water phase, heating to react, stopping the reaction, alternately washing the obtained white balls with hot water and ethanol until the liquid is clear, and drying to obtain polystyrene cross-linked microspheres;
(2) Swelling the polystyrene crosslinking microsphere obtained in the step (1) in chloromethyl ether, adding a catalyst, heating to perform chloromethylation reaction, washing with water, and drying to obtain chloromethylation polystyrene crosslinking microsphere;
(3) Swelling the chloromethylated polystyrene crosslinking microsphere prepared in the step (2) in dioxane, then adding triethylamine, heating for amination reaction, washing with water, and drying to obtain macroporous anion exchange resin;
the cross-linking agent is diallyl n-propyl isocyanurate.
2. The method for producing a macroporous anion exchange resin for water treatment according to claim 1, wherein: the dispersing agent is polyvinyl alcohol or gelatin.
3. The method for producing a macroporous anion exchange resin for water treatment according to claim 1, wherein: the pore-forming agent is isobutanol, and the initiator is benzoyl peroxide.
4. The method for producing a macroporous anion exchange resin for water treatment according to claim 1, wherein: the dispersing agent is used in an amount of 0.5-1.5% of the water phase, the sodium chloride is used in an amount of 0.05-0.1% of the water phase, and the methylene blue is used in an amount of 0.01-0.05% of the water phase.
5. The method for producing a macroporous anion exchange resin for water treatment according to claim 1, wherein: the usage amount of the cross-linking agent is 10-20% of the mass of the styrene, the usage amount of the pore-forming agent is 50-100% of the total mass of the styrene and the cross-linking agent, the usage amount of the initiator is 0.5-1% of the total mass of the styrene and the cross-linking agent, and the volume ratio of the water phase to the oil phase is (1-3): 1.
6. The method for producing a macroporous anion exchange resin for water treatment according to claim 1, wherein: the catalyst is anhydrous ferric chloride or anhydrous zinc chloride.
7. The method for producing a macroporous anion exchange resin for water treatment according to claim 1, wherein: the dosage of the catalyst is 20-50% of the mass of the polystyrene crosslinking microsphere.
8. The method for producing a macroporous anion exchange resin for water treatment according to claim 1, wherein: the dosage of the triethylamine is 5-15% of the mass of the chloromethylated polystyrene crosslinking microsphere.
9. Use of a macroporous anion exchange resin prepared by the method of any one of claims 1 to 8 in the treatment of aromatic sulfonic acid compound wastewater.
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