CN110921755A - Oxygen-enriched super-crosslinked porous organic polymer material, preparation method and application - Google Patents
Oxygen-enriched super-crosslinked porous organic polymer material, preparation method and application Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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- C02F1/00—Treatment of water, waste water, or sewage
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- 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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Abstract
The invention belongs to the technical field of industrial sewage treatment, and provides an oxygen-enriched super-crosslinked porous organic polymer material, a preparation method and application thereof, wherein the material contains an electron-enriched oxygen-containing functional group; the oxygen-enriched super-crosslinked porous organic polymer material is used for quickly enriching aniline in sewage, and high-capacity and high-selectivity adsorption of aniline in a complex sewage system is realized. Compared with the traditional immobilized microorganism-anaerobic biological filter treatment, Fenton catalytic degradation, formaldehyde polycondensation-Fenton oxidation-NaClO oxidation combination and iron-carbon micro-electrolysis technology, the method has the advantages of mild reaction conditions, cheap and efficient catalyst, environment-friendly reaction, high-efficiency aniline adsorption, good application prospect and high practical value.
Description
Technical Field
The invention belongs to the technical field of industrial sewage treatment, and particularly relates to preparation of an oxygen-rich super-crosslinked porous organic polymer material and application of the oxygen-rich super-crosslinked porous organic polymer material in purification of persistent aniline pollutants in sewage.
Background
The existing treatment technology for aniline sewage is divided into three categories of biology, physics and chemistry, and mainly comprises immobilized microorganism-anaerobic biological filter treatment, immobilized microorganism-aeration biological filter treatment, modified carbon material adsorption treatment and Fenton catalysisThe combined technology of degradation, formaldehyde polycondensation, Fenton oxidation and NaClO oxidation, iron-carbon micro-electrolysis and catalytic iron internal micro-electrolysis. The adsorption treatment of the modified carbon material and the Fenton catalytic degradation technology are common methods in the national standard. 201310572601.5 Aniline waste water is treated by Fenton catalytic degradation reaction, and they are decomposed by H2O2The generated hydroxyl free radicals degrade macromolecular aniline into small molecular organic matters or mineralize into CO2And H2O and other inorganic matters to achieve the aim of purifying the wastewater, and the method has the biggest defect that a large amount of sludge is generated in the aniline wastewater purification process, so that the difficulty and the cost of secondary treatment of enterprises are increased.
The adsorption treatment of the modified carbon material overcomes the defects of the common Fenton catalytic degradation technology, and has the advantages of high adsorption speed, high adsorption efficiency on aniline pollutants, economic and efficient treatment process and no secondary pollution, so the modified carbon material has good development prospect in the technical field of industrial sewage treatment. The greatest challenge of the existing adsorption material for purifying persistent aniline pollutants in sewage mainly comes from the limitation of the specific surface area and the content of functional groups of the material, so that the purification efficiency is not high, and the modified carbon material needs to be further optimized. Therefore, the development of a carbon material with high functional group content and large specific surface area is a key technology for realizing high-capacity and high-selectivity adsorption of persistent aniline pollutants in sewage.
Hypercrosslinked porous organic polymers (HCPs) are a new class of porous materials with abundant hierarchical pores, interconnected by covalent bonds from light elements (C, H, O, N, B, etc.). The modified epoxy resin has the advantages of low skeleton density, low cost, modifiable surface functional groups and large specific surface area, and has good stability under severe conditions of acid, alkali, solvent, moisture, high temperature and the like. In addition, the organic monomers for synthesizing HCPs have rich varieties, and the pore structure, the size and the functionalization of the pore structure can be regulated and controlled by selecting reaction monomers with different functional groups and different cross-linking agents. The synthesized HCPs material containing the oxygen-rich functional group and having the high specific surface area can be used for high-capacity and high-selectivity adsorption of persistent aniline pollutants in sewage through strong van der Waals force, pi-pi accumulation, hydrophobic interaction, acid-base interaction and multiple hydrogen bond interaction with aniline.
Disclosure of Invention
The invention aims to solve the technical problem of the adsorption rate of persistent aniline pollutants in the existing sewage, and provides an oxygen-rich super-crosslinked porous organic polymer material which contains electron-rich oxygen-containing functional groups; the other purpose of the invention is to provide a simple and easy-to-operate preparation method of the oxygen-enriched super-crosslinked porous organic polymer material; the invention also aims to provide the oxygen-rich hypercrosslinked porous organic polymer material for rapidly enriching the aniline in the sewage and realizing the high-capacity and high-selectivity adsorption of the aniline in a complex sewage system.
The technical scheme adopted by the invention for solving the technical problems is as follows: an oxygen-rich hypercrosslinked porous organic polymer material, the porous organic polymer material contains a skeleton rich in nucleophilic oxygen atoms, and has the following chemical formula:
the preparation method of the oxygen-rich hypercrosslinked porous organic polymer material is characterized by comprising the following steps: dimethoxymethane is added into the aromatic monomer containing the oxygen functional group, and the molar mass ratio of the aromatic monomer containing the oxygen functional group to the dimethoxymethane is 1: 1-10; adding Lewis acid as a catalyst for polymerization reaction, wherein the molar mass ratio of the aromatic monomer containing oxygen functional groups to the Lewis acid catalyst is 1: 1-10; adding 1, 2-dichloroethane as a solvent to completely dissolve the aromatic monomer, heating to 30-120 ℃ under the condition of vigorous stirring, and uniformly polymerizing the aromatic monomer containing oxygen functional groups for 12-48 h; performing Soxhlet extraction on the obtained tan solid with anhydrous methanol as solvent until the rainbow liquid is colorless and transparent, and extracting for 12-72 h; filtering and drying to obtain the oxygen-enriched super-crosslinked porous organic polymer material.
The aromatic monomer containing oxygen functional group is one or more than two of benzaldehyde, acetophenone, biphenol, anisole and phenol.
The Lewis acid catalyst is one of ferric trichloride, aluminum trichloride or boron trifluoride.
The preferable scheme of the method comprises the following steps: the molar mass ratio of the aromatic monomer containing the oxygen functional group to the dimethoxymethane is 1:2, and the molar mass ratio of the aromatic monomer containing the oxygen functional group to the Lewis acid catalyst is 1: 3; heating to 80 deg.C, polymerizing for 24h, and extracting for 24 h.
The invention also provides application of the oxygen-enriched hypercrosslinked porous organic polymer material in adsorption of persistent aniline pollutants.
In the application of the oxygen-rich super-crosslinked porous organic polymer material, the initial concentration ratio of the oxygen-rich super-crosslinked porous organic polymer material to aniline is 4-400: 1, the pH value of an adsorption system is 2-13, the adsorption temperature is 10-50 ℃, and the adsorption time is 2-15 h.
The preferable application scheme is as follows: the initial concentration ratio of the oxygen-rich hypercrosslinked porous organic polymer material to aniline is 50:1, the pH of an adsorption system is 3, the adsorption temperature is 30 ℃, and the adsorption time is 6 h.
Compared with the similar porous organic polymer material, the invention has the remarkable advantages that:
the oxygen-enriched super-crosslinked porous organic polymer material has a large specific surface area, rich mesoporous and microporous structures, high content of oxygen-containing functional groups uniformly distributed in a material framework, stability, low possibility of loss, long service life and reusability.
The invention is based on a super-crosslinked porous organic polymer material which has a large specific surface area and is rich in oxygen functional groups, and the super-crosslinked porous organic polymer material is used as a solid-phase adsorption material and can be used for high-capacity and high-selectivity adsorption of aniline in a sewage complex sample system through stronger van der Waals force, pi-pi accumulation, hydrophobic interaction, acid-base interaction and multiple hydrogen bond interaction.
Drawings
FIG. 1 shows a spectrum of a nitrogen physical adsorption analysis (adsorption-desorption isotherm of a benzaldehyde porous organic polymer material) of an oxygen-rich hypercrosslinked porous organic polymer material A of the present invention.
FIG. 2 is a nitrogen physical adsorption analysis spectrum (a pore size distribution diagram of a benzaldehyde porous organic polymer material) of an oxygen-rich hypercrosslinked porous organic polymer material A of the present invention.
FIG. 3 is a transmission electron microscope image of an oxygen-rich super-crosslinked porous organic polymer material A of the present invention.
FIG. 4 is a contact angle test chart of the oxygen-rich hypercrosslinked porous organic polymer material A of the present invention.
FIG. 5 is a graph of UV absorption of persistent aniline contaminants in wastewater.
FIG. 6 is a standard curve of UV absorption of persistent aniline pollutants in wastewater.
Detailed Description
The process provided by the present invention is described in detail below with reference to examples, but the present invention is not limited thereto in any way.
EXAMPLE 1 preparation of Material A
In a 50mL round-bottom single-neck flask, 2.1667g benzaldehyde, 4.33g dimethoxymethane, 20mL1, 2-dichloroethane as solvent, 6.5g FeCl were added3As a catalyst for polymerization reaction, heating to 80 ℃ under the condition of vigorous stirring to uniformly polymerize benzaldehyde and dimethoxymethane, wherein the polymerization time is 24 h. And performing Soxhlet extraction on the obtained tan solid by using absolute methanol as a solvent, extracting for 24h, filtering, and drying at 80 ℃ to obtain the oxygen-enriched super-crosslinked porous organic polymer material A.
EXAMPLE 2 preparation of Material B
In a 50mL round-bottom single-neck flask, 4.3334g of acetophenone, 8.66g of dimethoxymethane, 20mL of 1, 2-dichloroethane as a solvent, and 6.5g of FeCl were added3As a catalyst for polymerization reaction, the catalyst is heated to 40 ℃ under the condition of vigorous stirring, so that benzaldehyde and dimethoxymethane are uniformly polymerized for 12 h. And performing Soxhlet extraction on the obtained tan solid by using absolute methanol as a solvent, extracting for 12h, filtering, and drying at 80 ℃ to obtain the oxygen-enriched super-crosslinked porous organic polymer material B.
EXAMPLE 3 preparation of Material C
In a 50mL round bottom single-neck flask,6.5g of biphenol, 8.66g of dimethoxymethane, 20mL of 1, 2-dichloroethane as solvent and 13.0g of FeCl were added3As a catalyst for polymerization reaction, the catalyst is heated to 100 ℃ under the condition of vigorous stirring, so that benzaldehyde and dimethoxymethane are uniformly polymerized for 6 hours. And performing Soxhlet extraction on the obtained tan solid by using absolute methanol as a solvent, extracting for 42h, filtering, and drying at 80 ℃ to obtain the oxygen-enriched super-crosslinked porous organic polymer material C.
EXAMPLE 4 preparation of Material D
In a 50mL round-bottom single-neck flask, 8.67g anisole, 12.99g dimethoxymethane, 20mL1, 2-dichloroethane as solvent, and 19.5g FeCl were added3As a catalyst for polymerization reaction, the catalyst is heated to 110 ℃ under the condition of vigorous stirring, so that benzaldehyde and dimethoxymethane are uniformly polymerized for 10 h. And performing Soxhlet extraction on the obtained tan solid by using absolute methanol as a solvent, extracting for 20h, filtering, and drying at 80 ℃ to obtain the oxygen-enriched super-crosslinked porous organic polymer material D.
EXAMPLE 5 preparation of Material E
In a 50mL round-bottom single-neck flask, 10.8g of phenol, 21.65g of dimethoxymethane, 20mL of 1, 2-dichloroethane as a solvent, and 19.5g of FeCl were added3As a catalyst for polymerization reaction, the catalyst is heated to 120 ℃ under the condition of vigorous stirring, so that benzaldehyde and dimethoxymethane are uniformly polymerized, and the polymerization time is 18 h. And performing Soxhlet extraction on the obtained tan solid by using absolute methanol as a solvent, extracting for 36h, filtering, and drying at 80 ℃ to obtain the oxygen-enriched super-crosslinked porous organic polymer material E.
EXAMPLE 6 preparation of Material F
In a 50mL round-bottom single-neck flask, 1g benzaldehyde, 1.2g acetophenone, 12.99g dimethoxymethane, 20mL1, 2-dichloroethane as solvent, 13.0g FeCl were added3As a catalyst for polymerization reaction, heating to 80 ℃ under the condition of vigorous stirring to uniformly polymerize benzaldehyde, acetophenone and dimethoxymethane for 20 h. Subjecting the obtained brown solid to Soxhlet extraction with anhydrous methanol as solventExtracting for 48h, filtering, and drying at 80 ℃ to obtain the oxygen-enriched hypercrosslinked porous organic polymer material F.
EXAMPLE 7 preparation of Material G
In a 50mL round-bottom single-neck flask, 3g of acetophenone, 1.3g of biphenol, 8.66g of dimethoxymethane, 20mL of 1, 2-dichloroethane as a solvent, and 6.5g of FeCl were added3As a catalyst for polymerization reaction, the mixture is heated to 30 ℃ under the condition of vigorous stirring, so that acetophenone, biphenol and dimethoxymethane are uniformly polymerized for 24 hours. And performing Soxhlet extraction on the obtained tan solid by using absolute methanol as a solvent, extracting for 72h, filtering, and drying at 80 ℃ to obtain the oxygen-enriched super-crosslinked porous organic polymer material G.
EXAMPLE 8 preparation of Material H
In a 50mL round-bottom single-neck flask, 5g of biphenol, 1.5g of benzaldehyde, 8.66g of dimethoxymethane, 20mL of 1, 2-dichloroethane as a solvent, and 13.0g of FeCl were added3As a catalyst for polymerization reaction, heating to 120 ℃ under the condition of vigorous stirring to uniformly polymerize the diphenol benzaldehyde and the dimethoxymethane, wherein the polymerization time is 18 h. And performing Soxhlet extraction on the obtained tan solid by using absolute methanol as a solvent, extracting for 36H, filtering, and drying at 80 ℃ to obtain the oxygen-enriched super-crosslinked porous organic polymer material H.
Examples 9 to 16
Examples 9-16 disclose the effect of different adsorbent monomer species on aniline adsorption capacity, and the specific experimental procedures are described below:
0.5g of the material prepared above was added to an Erlenmeyer flask with 50ml of an aqueous aniline solution having an initial concentration of 200mg/L, the solution was adjusted to pH 3, and then the Erlenmeyer flask was transferred to a constant temperature shaker and shaken at 30 ℃ for 6 hours to ensure the sufficiency of adsorption and the stability of the process. After equilibrium of adsorption, and according to qe＝(Co-Ce) V/W determination of the adsorption Capacity qt(mg/g) and adsorption rate (%). The results are shown in Table 1
Table 1: effect of different adsorbents on the ability to adsorb Aniline
Examples 17 to 24
Examples 17-24 disclose the effect of the addition of the adsorbent on the ability to adsorb aniline, and the specific experimental procedure is described below:
a quantity of material A prepared as described above was added to an Erlenmeyer flask with 50ml of an initial 200mg/L aqueous aniline solution, the solution was adjusted to pH 3, and the Erlenmeyer flask was subsequently transferred to a constant temperature shaker at 30 ℃ for 6h with shaking, in order to ensure the adequacy of the adsorption and the stability of the process. After equilibrium of adsorption, and according to qe＝(Co-Ce) V/W determination of the adsorption Capacity qt(mg/g) and adsorption rate (%). The results are shown in Table 2
Table 2: influence of addition amount of adsorbent on aniline adsorption capacity
Examples 25 to 32
Examples 25-32 disclose the effect of different initial aniline concentrations on the ability to adsorb aniline, and the specific experimental procedures are described below:
0.5g of material A, prepared as described above, was added to an Erlenmeyer flask with 50ml of an aqueous aniline solution at a certain initial concentration, the solution was adjusted to pH 3, and the Erlenmeyer flask was subsequently transferred to a constant temperature shaker at 30 ℃ for 6h with shaking, in order to ensure the adequacy of the adsorption and the stability of the process. After equilibrium of adsorption, and according to qe＝(Co-Ce) V/W determination of the adsorption Capacity qt(mg/g) and adsorption rate (%). The results are shown in Table 3
Table 3: effect of different initial concentrations of Aniline on Aniline adsorption Capacity
Examples 33 to 37
Examples 33-37 disclose the effect of adsorption temperature on aniline adsorption capacity, and the specific experimental procedures are described below:
0.5g of material A, prepared as described above, is introduced into an Erlenmeyer flask with 50ml of an aqueous aniline solution having an initial concentration of 200mg/L, the solution is adjusted to pH 3, and the Erlenmeyer flask is subsequently transferred into a constant temperature shaker and shaken at constant temperature for 6h in order to ensure the completeness of the adsorption and the stability of the process. After equilibrium of adsorption, and according to qe＝(Co-Ce) V/W determination of the adsorption Capacity qt(mg/g) and adsorption rate (%). The results are shown in Table 4
Table 4: influence of adsorption temperature on Aniline adsorbing ability
Examples 38 to 42
Examples 38-42 disclose the effect of adsorption time on aniline adsorption capacity, and the specific experimental procedure is described below:
0.5g of material A, prepared as described above, is introduced into an Erlenmeyer flask with 50ml of an aqueous aniline solution having an initial concentration of 200mg/L, the solution is adjusted to pH 3, and the Erlenmeyer flask is subsequently transferred to a constant temperature shaker and shaken at 30 ℃ for a certain period of time in order to ensure the completeness of the adsorption and the stability of the process. After equilibrium of adsorption, and according to qe＝(Co-Ce) V/W determination of the adsorption Capacity qt(mg/g) and adsorption rate (%). The results are shown in Table 5
Table 5: influence of adsorption time on the ability to adsorb aniline
Examples 43 to 48
Examples 43-48 disclose the effect of the pH of the adsorption system on the ability to adsorb aniline, and the specific experimental procedure is described below:
0.5g of Material A, prepared as described above, was added to a solution having a viscosity of 50ml of an aqueous aniline solution with an initial concentration of 200mg/L, adjusting the pH of the solution, and then transferring the flask to a constant temperature oscillator, and oscillating the solution at 30 ℃ for 6 hours to ensure the sufficiency of adsorption and the stability of the process. After equilibrium of adsorption, and according to qe＝(Co-Ce) V/W determination of the adsorption Capacity qt(mg/g) and adsorption rate (%). The results are shown in Table 6
Table 6: influence of the pH of the reaction System on the ability to adsorb Aniline
Examples 49 to 53
Examples 49-53 disclose the universal impact of adsorbents on different adsorbates, and the specific experimental procedures are described below:
0.5g of material A, prepared as described above, was added to an Erlenmeyer flask with 50ml of an initial 200mg/L aqueous solution of the substance, the solution was adjusted to pH 3, and the Erlenmeyer flask was then transferred to a constant temperature shaker at 30 ℃ for 6h to ensure the adequacy of the adsorption and the stability of the process. After equilibrium of adsorption, and according to qe＝(Co-Ce) V/W determination of the adsorption Capacity qt(mg/g) and adsorption rate (%). The results are shown in Table 7
Table 7: universal influence of adsorbents on different adsorbates
Claims (8)
1. An oxygen-rich hypercrosslinked porous organic polymer material, characterized in that the porous organic polymer material contains a skeleton rich in nucleophilic oxygen atoms, and has the following chemical formula:
2. the method for preparing the oxygen-rich hypercrosslinked porous organic polymer material of claim 1, comprising the steps of: dimethoxymethane is added into the aromatic monomer containing the oxygen functional group, and the molar mass ratio of the aromatic monomer containing the oxygen functional group to the dimethoxymethane is 1: 1-10; adding Lewis acid as a catalyst for polymerization reaction, wherein the molar mass ratio of the aromatic monomer containing oxygen functional groups to the Lewis acid catalyst is 1: 1-10; adding 1, 2-dichloroethane as a solvent to completely dissolve the aromatic monomer, heating to 30-120 ℃ under the condition of vigorous stirring, and uniformly polymerizing the aromatic monomer containing oxygen functional groups for 12-48 h; performing Soxhlet extraction with the obtained brown solid anhydrous methanol as solvent until the siphon liquid is colorless and transparent, and extracting for 12-72 h; filtering and drying to obtain the oxygen-enriched super-crosslinked porous organic polymer material.
3. The method for preparing the oxygen-rich hypercrosslinked porous organic polymer material as claimed in claim 2, wherein the aromatic monomer containing oxygen functional group is one or more of benzaldehyde, acetophenone, biphenol, anisole and phenol.
4. The method for preparing the oxygen-rich hypercrosslinked porous organic polymer material as claimed in claim 2, wherein the Lewis acid catalyst is one of ferric trichloride, aluminum trichloride or boron trifluoride.
5. The method for preparing the oxygen-rich hypercrosslinked porous organic polymer material as claimed in claim 2, wherein the molar mass ratio of the aromatic monomer containing oxygen functional group to dimethoxymethane is 1:2, the molar mass ratio of the aromatic monomer containing oxygen functional group to Lewis acid catalyst is 1: 3; heating to 80 deg.C, polymerizing for 24h, and extracting for 24 h.
6. Use of the oxygen-rich hypercrosslinked porous organic polymeric material of claim 1 for adsorbing persistent aniline contaminants.
7. The application of the oxygen-rich hypercrosslinked porous organic polymer material as claimed in claim 6, wherein the initial concentration ratio of the oxygen-rich hypercrosslinked porous organic polymer material to aniline is 4-400: 1, the adsorption system pH is 2-13, the adsorption temperature is 10-50 ℃, and the adsorption time is 2-15 h.
8. The application of the oxygen-rich hypercrosslinked porous organic polymer material as claimed in claim 6, wherein the initial concentration ratio of the oxygen-rich hypercrosslinked porous organic polymer material to aniline is 50:1, the adsorption system pH is 3, the adsorption temperature is 30 ℃, and the adsorption time is 6 h.
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