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CN-121975107-A - Adsorbent material for perfluoro compounds in water, and preparation method and application thereof

CN121975107ACN 121975107 ACN121975107 ACN 121975107ACN-121975107-A

Abstract

The invention discloses an adsorbent material for perfluoro compounds in water, a preparation method and application thereof, and belongs to the technical field of water treatment materials, wherein 1, 3-diamino-2-hydroxy propane, m-hydroxybenzoic acid and 3,3' -bis (1, 4-phenylene) bis [ 2-propynoic acid ] are taken as raw materials, a polyamide polymer is obtained through reaction, and finally m-hydroxybenzoic acid is removed through hydrolysis, so that the polymer adsorbent material is prepared; the adsorbent material for the perfluorinated compounds in the water, which is prepared by the invention, has larger specific surface area and adsorption capacity, can be used for adsorbing the perfluorinated compounds in the water, has stronger mechanical stability, service life and regeneration capacity, and has good application prospect in the aspect of removing the perfluorinated compounds in the water.

Inventors

  • YAN HAN
  • LENG YANQIU
  • YANG XUEQIAO

Assignees

  • 山东省环科院环境检测有限公司

Dates

Publication Date
20260505
Application Date
20260112

Claims (10)

  1. 1. An adsorbent material for perfluoro compound in water is prepared from 1, 3-diamino-2-hydroxy propane, m-triphenyl acid and 3,3' - (1, 4-phenylene) bis [ 2-propynoic acid ] through reaction to obtain polyamide polymer, and hydrolysis to remove m-triphenyl acid.
  2. 2. The method for preparing the adsorbent material for perfluoro compounds in water according to claim 1, which is characterized by comprising the following steps: 1) Adding 1, 3-diamino-2-hydroxy propane into an organic solvent 1, stirring and dissolving, then adding di-tert-butyl dicarbonate, reacting for 6-8 hours at 25-40 ℃, and after the reaction is finished, carrying out suction filtration, and distilling the obtained filtrate under reduced pressure to remove the solvent to obtain amino-protected hydroxy propane; 2) Adding the amino-protected hydroxy propane and the m-tribenzoic acid prepared in the step 1) into an organic solvent 2, stirring and mixing uniformly, adding 4-dimethylaminopyridine and 1-ethyl- (3-dimethylaminopropyl) carbodiimide, reacting for 12-24 hours at 25-40 ℃, after the reaction is finished, carrying out suction filtration, distilling the obtained filtrate under reduced pressure to remove the solvent, washing the obtained residue for 2-3 times by using 1-3 mol/L alkali liquor, adding the residue into the organic solvent 1, adding trifluoroacetic acid into the organic solvent, stirring and mixing uniformly, reacting for 5-12 hours at 25-35 ℃, after the reaction is finished, distilling the solvent under reduced pressure to remove the solvent, washing for 2-3 times by using 1-3 mol/L alkali liquor, and drying to obtain an amino-terminated esterified product; 3) Adding the amino-terminated ester prepared in the step 2) and 3,3' - (1, 4-phenylene) bis [ 2-propynoic acid ] into an organic solvent 2, adding diethyl azodicarboxylate and 1-hydroxybenzotriazole, reacting for 24-48 hours at 40-80 ℃, after the reaction is finished, performing suction filtration, washing the obtained filter cake with the organic solvent 3 for 3-5 times, washing with saturated sodium chloride aqueous solution for 3-5 times, and drying to obtain a polyamide polymer; 4) Adding the polyamide polymer prepared in the step 3) into an organic solvent 4, adding alkali, stirring and mixing uniformly, reacting for 12-24 hours at 40-80 ℃, carrying out suction filtration after the reaction is finished, washing the obtained filter cake with the organic solvent 2 for 3-5 times, washing with water for 3-5 times, and drying to obtain the adsorbent material for the perfluoro compound in water.
  3. 3. The method for preparing an adsorbent material for perfluoro compounds in water according to claim 2, wherein the organic solvent 1 in the step 1) is methylene chloride or chloroform, and the mass ratio of the 1, 3-diamino-2-hydroxypropane, the organic solvent 1 and the di-tert-butyl dicarbonate in the step 1) is 1:10-20:5-6.
  4. 4. The method for preparing an adsorbent material for a perfluoro compound in water according to claim 2, wherein the organic solvent 2 in the step 2) is tetrahydrofuran, dimethylformamide, acetone or dimethyl sulfoxide, and the mass ratio of the amino-protected hydroxypropane, m-tribenzoic acid, the organic solvent 2, 4-dimethylaminopyridine, 1-ethyl- (3-dimethylaminopropyl) carbodiimide, the organic solvent 1 and trifluoroacetic acid in the step 2) is 4.5-5:1:10-20:0.6-1:0.9-1.5:10-20:0.6-0.8.
  5. 5. The method of claim 2, wherein the alkali in step 2) is sodium hydroxide or potassium hydroxide.
  6. 6. The method for producing an adsorbent material for perfluoro compounds in water according to claim 2, wherein said organic solvent 3 in step 3) is ethanol, acetonitrile, acetone, methanol or tetrahydrofuran.
  7. 7. The method for producing an adsorbent material for a perfluoro compound in water according to claim 2, wherein the mass ratio of the amine-terminated ester, 3' - (1, 4-phenylene) bis [ 2-propynoic acid ], the organic solvent 2, diethyl azodicarboxylate and 1-hydroxybenzotriazole in the step 3) is 1:3 to 5:10 to 20:0.6 to 1:0.5 to 0.8.
  8. 8. The method for preparing an adsorbent material for a perfluoro compound in water according to claim 2, wherein the organic solvent 4 in the step 4) is methanol, ethanol or dimethylformamide, and the mass ratio of the polyamide polymer, the organic solvent 4 and the base in the step 4) is 1:10-20:0.5-1.
  9. 9. Use of the adsorbent material for perfluoro compounds in water according to claim 1 for the treatment of perfluoro compounds in water.
  10. 10. Use of the adsorbent material for perfluoro compounds in water according to claim 9, characterized in that: the perfluoro compound is perfluoro octanoic acid, perfluoro octyl sulfonic acid or perfluoro cyclohexane.

Description

Adsorbent material for perfluoro compounds in water, and preparation method and application thereof Technical Field The invention belongs to the technical field of water treatment materials, and particularly relates to an adsorbent material for perfluoro compounds in water, a preparation method and application thereof. Background Perfluorochemicals (PFCs) are widely used in daily necessities such as non-stick pan coating, waterproof clothes, food packaging and the like due to the excellent characteristics of hydrophobicity, oleophobicity, thermal stability, corrosion resistance and the like, PFCs are migrated to nearby surface water along with sewage discharge in the mass production, use and disposal processes, and the PFCs not only can produce different degrees of toxic action on aquatic animals and plants, but also can be accumulated in higher organisms and human bodies through food chains to endanger ecological safety and human health, so that the PFCs are effectively removed, but the PFCs are extremely stable in carbon-fluorine bond, are almost ineffective in conventional water treatment process and are necessary to rely on expensive advanced oxidation, adsorption or membrane technology. The traditional adsorbents have obvious defects in the aspect of removing perfluorinated compounds, firstly, the selective adsorption capability of the traditional adsorbents on perfluorinated compounds is generally poor, in complex wastewater with high salinity and multiple components, limited active sites of the traditional adsorbents are easily occupied by background impurities (such as natural organic matters) preferentially, so that the adsorption efficiency is drastically reduced, i.e. poisoning phenomenon occurs, secondly, the traditional adsorbents are solid particles, the adsorption process is seriously dependent on limited surface pore channels, the internal volume is difficult to effectively utilize, material waste and poor mass transfer permeability are caused, and finally, after adsorption saturation, the desorption and regeneration of the adsorbents are generally difficult, so that the operation cost is increased, and the problem of secondary disposal is brought. Therefore, the preparation of the perfluoro compound selective adsorption material has important significance for realizing economical, efficient and environment-friendly removal of perfluoro compounds in water. Disclosure of Invention In order to solve the problems, the invention aims to provide an adsorbent material for perfluoro compounds in water, and a preparation method and application thereof. The invention aims to achieve the aim, and the aim is achieved by the following technical scheme: An adsorbent material for perfluoro compound in water is prepared from 1, 3-diamino-2-hydroxy propane, m-triphenyl acid and 3,3' - (1, 4-phenylene) bis [ 2-propynoic acid ] through reaction to obtain polyamide polymer, and hydrolysis to remove m-triphenyl acid. The preparation method of the adsorbent material for the perfluoro compound in water specifically comprises the following steps: 1) Adding 1, 3-diamino-2-hydroxy propane into an organic solvent 1, stirring and dissolving, then adding di-tert-butyl dicarbonate, reacting for 6-8 hours at 25-40 ℃, and after the reaction is finished, carrying out suction filtration, and distilling the obtained filtrate under reduced pressure to remove the solvent to obtain amino-protected hydroxy propane; 2) Adding the amino-protected hydroxy propane and the m-tribenzoic acid prepared in the step 1) into an organic solvent 2, stirring and mixing uniformly, adding 4-dimethylaminopyridine and 1-ethyl- (3-dimethylaminopropyl) carbodiimide, reacting for 12-24 hours at 25-40 ℃, after the reaction is finished, carrying out suction filtration, distilling the obtained filtrate under reduced pressure to remove the solvent, washing the obtained residue for 2-3 times by using 1-3 mol/L alkali liquor, adding the residue into the organic solvent 1, adding trifluoroacetic acid into the organic solvent, stirring and mixing uniformly, reacting for 5-12 hours at 25-35 ℃, after the reaction is finished, distilling the solvent under reduced pressure to remove the solvent, washing for 2-3 times by using 1-3 mol/L alkali liquor, and drying to obtain an amino-terminated esterified product; 3) Adding the amino-terminated ester prepared in the step 2) and 3,3' - (1, 4-phenylene) bis [ 2-propynoic acid ] into an organic solvent 2, adding diethyl azodicarboxylate and 1-hydroxybenzotriazole, reacting for 24-48 hours at 40-80 ℃, after the reaction is finished, performing suction filtration, washing the obtained filter cake with the organic solvent 3 for 3-5 times, washing with saturated sodium chloride aqueous solution for 3-5 times, and drying to obtain a polyamide polymer; 4) Adding the polyamide polymer prepared in the step 3) into an organic solvent 4, adding alkali, stirring and mixing uniformly, reacting for 12-24 hours at 40-80 ℃, carrying