CN115138346A - Magnetic zeolite composite material, preparation method thereof and application of magnetic zeolite composite material in treatment of printing and dyeing wastewater - Google Patents
Magnetic zeolite composite material, preparation method thereof and application of magnetic zeolite composite material in treatment of printing and dyeing wastewater Download PDFInfo
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Abstract
The scheme relates to a magnetic zeolite composite material, a preparation method thereof and application of the magnetic zeolite composite material in treatment of printing and dyeing wastewater, wherein a ferrocene polymer is prepared by taking vinyl ferrocene, acrylic acid and p-styrene sulfonic acid as raw materials; then reacting with phenolic resin, wherein zeolite is added in the reaction process; continuously adding urotropine, polyethylene glycol and ethanol into the system after the reaction is finished, stirring and roasting at 350-500 ℃; crushing the obtained solid, adding the crushed solid into a prepared surfactant solution, carrying out water bath, then dropwise adding a hydrochloric acid solution, washing with water, and drying to obtain a magnetic zeolite composite material; said surfaceThe active agent solution is prepared by dissolving the following siloxane-containing Gemini surfactant in water,
r is an alkyl chain of C6-12. The magnetic zeolite composite material prepared by the scheme can be applied to adsorption of anionic dyes, is easy to recover after water treatment due to high stability and magnetism, and still has high adsorption of the regenerated anionic dyes.
Description
Technical Field
The invention relates to the technical field of printing and dyeing wastewater treatment, in particular to a magnetic zeolite composite material, a preparation method thereof and application of the magnetic zeolite composite material in printing and dyeing wastewater treatment.
Background
With the rapid development of the dye industry, a large amount of dye wastewater is generated. The printing and dyeing wastewater contains a large amount of organic matters which are difficult to degrade, has complex components and is difficult to decolor, and is one of the most difficult industrial wastewater to treat. Azo dyes are the most widely used dyes, have stable properties and high toxicity of intermediate products, and are a difficult problem in dye wastewater.
Zeolite is a natural aluminosilicate ore, has wide distribution and low cost, and is widely used in sewage treatment because of the ion exchange capacity and adsorption capacity of the aluminosilicate crystal with a frame structure and porosity. Mainly used for adsorbing cation inorganic pollutants such as ammonia nitrogen, heavy metals and the like, but has poor adsorption to anion organic matters. At present, the cationic surfactant CTAB is adopted to modify natural zeolite in the prior art, so that the method can be applied to decolorization and adsorption of anionic dye wastewater, the decolorization rate can reach about 73%, and a technical reference is provided for further application of the natural zeolite in the field of wastewater treatment. However, in the current research, the decolorization rate still needs to be improved; secondly, the zeolite is easily regenerated, but the recovery rate is low.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides the magnetic zeolite composite material which is easy to recycle and regenerate, can be applied to the treatment of anionic dye wastewater and has high decolorization rate.
In order to achieve the purpose, the invention provides the following technical scheme:
a preparation method of a magnetic zeolite composite material comprises the following steps:
s1: adding vinyl ferrocene, acrylic acid and p-styrenesulfonic acid into a reaction bottle, adding an organic solvent and an initiator, reacting for 24 hours at the temperature of 60-70 ℃ under the protection of nitrogen, and precipitating in toluene after the reaction is finished to obtain a ferrocene polymer;
s2: dissolving ferrocene polymer, phenolic resin and 4-dimethylaminopyridine in an organic solvent, adding a certain amount of zeolite, ultrasonically dispersing uniformly, then dropwise adding an organic solution containing dicyclohexylcarbodiimide, and stirring at normal temperature overnight;
s3: continuously adding urotropin, polyethylene glycol and ethanol into the S2, heating and refluxing for 1-2 h, distilling under reduced pressure to remove the organic solvent, and then roasting at 350-500 ℃ for 1-3 h;
s4: crushing the solid obtained by roasting the S3, adding the crushed solid into a prepared surfactant solution, carrying out water bath for 1-3 h at the temperature of 40-60 ℃, then dropwise adding a hydrochloric acid solution, continuously stirring for 2-4 h, then washing with water, and drying to obtain a magnetic zeolite composite material;
wherein the surfactant solution is prepared by dissolving a siloxane-containing Gemini surfactant shown in a formula 1) in water,
r is an alkyl chain of C6-12.
Furthermore, the mol ratio of the vinylferrocene, the acrylic acid and the p-styrenesulfonic acid in the S1 is 1.
Further, the organic solvent is selected from one of THF, chloroform, DMF and DMSO; the initiator is azobisisobutyl or azobisisoheptyl.
Furthermore, the mass ratio of the ferrocene polymer, the phenolic resin and the zeolite in the S2 is 1-3.
Further, the mass of the urotropine, the polyethylene glycol and the ethanol is 10%, 10% and 200% of the mass of the zeolite.
Furthermore, the mass fraction of the surfactant solution in the S4 is 1-5%, and the mass of the solid is 10-20 times of that of the surfactant.
The invention further provides a magnetic zeolite composite material prepared by the preparation method.
The invention further provides an application of the magnetic zeolite composite material in treating printing and dyeing wastewater.
At present, the organic modification of zeolite is usually to adsorb small molecular surfactant such as cetyl trimethyl ammonium bromide on the surface of zeolite, so as to change the surface characteristics of zeolite and adsorb anionic organic dye. However, the modification method usually adopts an impregnation method, the modification degree depends on the degree of the surfactant adsorbed on the zeolite, and the micromolecular surfactant has low degree of combination with the zeolite surface, low adsorption efficiency and easy removal in the water treatment process, so that the decoloration rate of the printing and dyeing wastewater is low; and the recovery rate is difficult, and the decolorizing effect after recovery and regeneration is also greatly reduced.
Compared with the prior art, the invention has the beneficial effects that: on one hand, ferrocene polymer and phenolic resin are added in the early stage of zeolite roasting, the ferrocene polymer firstly reacts with the phenolic resin through carboxyl in a polymer chain, and zeolite is coated in the ferrocene polymer through the reaction process, so that the iron loading rate is improved; in the roasting process, the aperture of the zeolite is promoted to be increased due to the larger steric hindrance effect of the ferrocene polymer, and iron easily enters pore channels of the zeolite, so that the zeolite is endowed with magnetism and is easy to recover through magnetic separation; on the other hand, the roasted zeolite is soaked in a siloxane-containing Gemini surfactant solution, contains two cationic quaternary ammonium salts, increases hydrophobic groups, and forms micelle-like coatings on the surface of the zeolite by double long carbon chains, so that the adsorption efficiency is high; the siloxane structure is hydrolyzed and polymerized under acidic condition to form polymer chain on the surface of zeolite, so that the binding force between the siloxane structure and zeolite is improved. Therefore, the finally prepared magnetic zeolite composite material can be applied to the adsorption of anionic dyes, and is easy to recover after water treatment due to high stability and magnetism, and still has high adsorption to the anionic dyes after regeneration.
Drawings
FIG. 1 is a graph showing the decolorization ratio of the samples obtained in examples 1 to 3 and comparative examples 1 to 3 after the simulated wastewater treatment.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments, and it should be apparent that the described embodiments are some, but not all, embodiments of the present 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.
In addition, the technical features involved in the different embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
Example 1:
s1: adding 0.1mol of vinyl ferrocene, 0.06mol of acrylic acid and 0.05mol of p-styrene sulfonic acid into a reaction bottle, adding 100ml of DMF and 1mmol of AIBN, reacting for 24h at the temperature of 60-70 ℃ under the protection of nitrogen, and precipitating in toluene after the reaction is finished to obtain a ferrocene polymer;
s2: dissolving 1g of ferrocene polymer, 2g of phenolic resin and 0.2g of 4-dimethylamino pyridine in THF, adding 6g of zeolite, ultrasonically dispersing uniformly, then dropwise adding 10g of 10wt% organic solution containing dicyclohexyl carbodiimide, and stirring at normal temperature overnight;
s3: continuously adding 0.6g of urotropin, 0.6g of polyethylene glycol and 12g of ethanol into the S2, heating and refluxing for 1-2 h, distilling under reduced pressure to remove the organic solvent, and then roasting at 380 ℃ for 1-3 h;
s4: crushing the solid obtained by roasting S3, adding 3g of the crushed solid into 50ml of 0.5wt% surfactant aqueous solution, performing water bath for 1-3 h at the temperature of 40 ℃, dropwise adding 5ml of 2mol/L hydrochloric acid solution, continuously stirring for 2-4 h, and then washing and drying to obtain the magnetic zeolite composite material; denoted sample 1.
The surfactant solution is prepared by dissolving a siloxane-containing Gemini surfactant in water, and the preparation process comprises the following steps:
r is C8 alkyl chain.
Example 2:
s1: adding 0.1mol of vinyl ferrocene, 0.06mol of acrylic acid and 0.05mol of p-styrenesulfonic acid into a reaction bottle, adding 100ml of DMF and 1mmol of AIBN, reacting for 24 hours at the temperature of 60-70 ℃ under the protection of nitrogen, and precipitating in toluene after the reaction is finished to obtain ferrocene polymer;
s2: dissolving 1.5g of ferrocene polymer, 4g of phenolic resin and 0.2g of 4-dimethylamino pyridine in THF, adding 7g of zeolite, ultrasonically dispersing uniformly, then dropwise adding 10g of 10wt% organic solution containing dicyclohexyl carbodiimide, and stirring at normal temperature overnight;
s3: continuously adding 0.7g of urotropin, 0.7g of polyethylene glycol and 14g of ethanol into the S2, heating and refluxing for 1-2 h, distilling under reduced pressure to remove the organic solvent, and then roasting at 380 ℃ for 1-3 h;
s4: and (2) crushing the solid obtained by roasting S3, adding 4g of the crushed solid into 50ml of 0.5wt% surfactant solution, performing water bath for 1-3 h at 40 ℃, then dropwise adding 5ml of 2mol/L hydrochloric acid solution, continuously stirring for 2-4 h, then washing with water, and drying to obtain the magnetic zeolite composite material, wherein the sample is marked as sample 2.
The surfactant solution is prepared from siloxane-containing Gemini surfactant
Dissolving in water to obtain the final product, wherein R is C10 alkyl chain.
Example 3:
s1: adding 0.1mol of vinyl ferrocene, 0.06mol of acrylic acid and 0.05mol of p-styrene sulfonic acid into a reaction bottle, adding 100ml of DMF and 1mmol of AIBN, reacting for 24h at the temperature of 60-70 ℃ under the protection of nitrogen, and precipitating in toluene after the reaction is finished to obtain a ferrocene polymer;
s2: dissolving 2g of ferrocene polymer, 4.5g of phenolic resin and 0.2g of 4-dimethylamino pyridine in THF, adding 7g of zeolite, ultrasonically dispersing uniformly, then dropwise adding 10g of 10wt% organic solution containing dicyclohexyl carbodiimide, and stirring at normal temperature overnight;
s3: continuously adding 0.7g of urotropin, 0.7g of polyethylene glycol and 14g of ethanol into the S2, heating and refluxing for 1-2 h, distilling under reduced pressure to remove the organic solvent, and then roasting at 380 ℃ for 1-3 h;
s4: and (3) crushing the solid obtained by roasting the S3, adding 5g of the crushed solid into 50ml of 0.5wt% surfactant solution, performing water bath for 1-3 h at the temperature of 40 ℃, dropwise adding 5ml of 2mol/L hydrochloric acid solution, continuously stirring for 2-4 h, then washing with water, and drying to obtain the magnetic zeolite composite material, wherein the sample is marked as sample 3.
The surfactant solution is prepared from siloxane-containing Gemini surfactant
Dissolving in water, wherein R is C12 alkyl chain.
Comparative example 1:
immersing natural zeolite in hexadecyl trimethyl ammonium bromide, oscillating at 40 ℃ for 12h, washing with water and drying to obtain a control sample 1.
Comparative example 2:
soaking natural zeolite in mixed solution of cetyl trimethyl ammonium bromide and KH560, oscillating at 40 deg.C for 12 hr, washing with water, and oven drying to obtain control 2.
Comparative example 3:
adding 1g of ferrocene, 6g of zeolite, 0.6g of urotropine, 0.6g of polyethylene glycol and 12g of ethanol into a reaction bottle, heating and refluxing for 1-2 h, distilling under reduced pressure to remove the organic solvent, and then roasting at 380 ℃ for 1-3 h;
and (3) crushing the solid obtained by roasting, adding 3g of the crushed solid into 50ml of 0.5wt% surfactant solution, performing water bath for 1-3 h at 40 ℃, then dropwise adding 5ml of 2mol/L hydrochloric acid solution, continuously stirring for 2-4 h, then washing with water, and drying to obtain the magnetic zeolite composite material, wherein the record of the magnetic zeolite composite material is reference 3.
The surfactant solution is prepared from siloxane-containing Gemini surfactant
Dissolving in water to obtain the final product, wherein R is C8 alkyl chain.
The application comprises the following steps:
preparing 50mg/L of orange G simulated wastewater, adding 50ml of simulated wastewater into 5 reaction bottles respectively, adding 0.1G of prepared sample 1-3 and control sample 1-2 respectively, stirring for 2h at room temperature, and calculating the decolorization rate by measuring the absorbance of orange G in the adsorbed wastewater.
As shown in fig. 1, the decolorization ratio of samples 1 to 3 is as high as more than 90%, wherein the adsorption effect of sample 2 is optimal; the decolorization rate of control 3 also reached 80%, compared to about 70% for controls 1 and 2.
After regeneration by magnetic separation (where controls 1 and 2 were recovered by centrifugation), adsorption was repeated five times, and after repeating five times, the fifth recovery and decolorization rates were calculated and reported in table 1.
TABLE 1
| Sample(s) | Percent recovery% | Decolorization ratio/% |
| Sample 1 | 92.3 | 87.2 |
| Sample 2 | 93.2 | 88.6 |
| Sample 3 | 92.1 | 86.9 |
| Control 1 | 79.8 | 35.6 |
| Control 2 | 75.7 | 36.4 |
| Control 3 | 48％ | 80.2 |
From the table above, the magnetic zeolite composite material prepared by the scheme can be recovered through magnetic separation, the recovery rate can reach more than 90%, the recovery is convenient, and the decolorization rate after regeneration can still keep more than 85%. The control sample 1 and the control sample 2 have no magnetism and can be recovered only by centrifugal separation, and the micromolecule surfactant has low adsorption efficiency on the surface of zeolite and good water solubility, is washed off after multiple times of centrifugal separation, and greatly reduces the adsorption effect on anionic dye; comparative sample 3, although having magnetic properties, had poor stability, and after multiple separations, iron was separated from the zeolite pores, and only a recovery rate of 48% was obtained after the fifth recovery by magnetic separation.
While embodiments of the invention have been disclosed above, it is not intended to be limited to the details shown in the description and the examples, which are set forth, but are fully applicable to various fields of endeavor as are suited to the particular use contemplated, and further modifications will readily occur to those skilled in the art, since the invention is not limited to the details shown and described without departing from the general concept as defined by the appended claims and their equivalents.
Claims (8)
1. The preparation method of the magnetic zeolite composite material is characterized by comprising the following steps of:
s1: adding vinyl ferrocene, acrylic acid and p-styrenesulfonic acid into a reaction bottle, adding an organic solvent and an initiator, reacting for 24 hours at the temperature of 60-70 ℃ under the protection of nitrogen, and precipitating in toluene after the reaction is finished to obtain a ferrocene polymer;
s2: dissolving ferrocene polymer, phenolic resin and 4-dimethylaminopyridine in an organic solvent, adding a certain amount of zeolite, ultrasonically dispersing uniformly, then dropwise adding an organic solution containing dicyclohexylcarbodiimide, and stirring at normal temperature overnight;
s3: continuously adding urotropin, polyethylene glycol and ethanol into the S2, heating and refluxing for 1-2 h, distilling under reduced pressure to remove the organic solvent, and then roasting at 350-500 ℃ for 1-3 h;
s4: crushing the solid obtained by roasting the S3, adding the crushed solid into a prepared surfactant solution, carrying out water bath for 1-3 h at the temperature of 40-60 ℃, then dropwise adding a hydrochloric acid solution, continuously stirring for 2-4 h, then washing with water, and drying to obtain a magnetic zeolite composite material;
wherein the surfactant solution is prepared by dissolving a siloxane-containing Gemini surfactant shown in a formula 1) in water,
r is an alkyl chain of C6-12.
2. The method for preparing a magnetic zeolite composite material according to claim 1, wherein the molar ratio of vinylferrocene, acrylic acid and p-styrenesulfonic acid in S1 is 1.
3. The method for preparing a magnetic zeolite composite material according to claim 1 wherein the organic solvent is selected from one of THF, chloroform, DMF, DMSO; the initiator is azobisisobutyl or azobisisoheptyl.
4. The method for preparing the magnetic zeolite composite material according to claim 1, wherein the mass ratio of the ferrocene polymer, the phenolic resin and the zeolite in the S2 is 1-3.
5. The method of preparing a magnetic zeolite composite material according to claim 1, wherein the mass of urotropin, polyethylene glycol and ethanol is 10%, 10% and 200% of the mass of zeolite.
6. The method for preparing a magnetic zeolite composite material according to claim 1, wherein the mass fraction of the surfactant solution in S4 is 1% to 5%, and the mass of the solid is 10 to 20 times the mass of the surfactant therein.
7. A magnetic zeolite composite material obtained by the production method according to any one of claims 1 to 6.
8. Use of a magnetic zeolite composite according to claim 7 for the treatment of printing and dyeing wastewater.
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| CN113457718A (en) * | 2021-06-25 | 2021-10-01 | 复旦大学 | Magnetic functional zeolite molecular sieve catalyst and preparation method thereof |
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2022
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| CN106365199A (en) * | 2016-10-19 | 2017-02-01 | 复旦大学 | Yolk-shell type structure material taking zeolite molecular sieve as core and mesoporous layer as shell, and preparation method of yolk-shell type structure material |
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