CN116216905A - Composition for selectively degrading aniline pollutants as well as preparation method and application thereof - Google Patents
Composition for selectively degrading aniline pollutants as well as preparation method and application thereof Download PDFInfo
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- CN116216905A CN116216905A CN202310189919.9A CN202310189919A CN116216905A CN 116216905 A CN116216905 A CN 116216905A CN 202310189919 A CN202310189919 A CN 202310189919A CN 116216905 A CN116216905 A CN 116216905A
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims abstract description 210
- 230000000593 degrading effect Effects 0.000 title claims abstract description 49
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 239000003344 environmental pollutant Substances 0.000 title claims abstract description 44
- 231100000719 pollutant Toxicity 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000002131 composite material Substances 0.000 claims abstract description 51
- 229920002678 cellulose Polymers 0.000 claims abstract description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 150000002989 phenols Chemical class 0.000 claims abstract description 15
- 239000002351 wastewater Substances 0.000 claims abstract description 14
- 239000007800 oxidant agent Substances 0.000 claims abstract description 13
- 239000001913 cellulose Substances 0.000 claims abstract description 12
- 230000001590 oxidative effect Effects 0.000 claims abstract description 11
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims abstract description 5
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 80
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 53
- 239000011259 mixed solution Substances 0.000 claims description 15
- 239000000356 contaminant Substances 0.000 claims description 14
- 239000012286 potassium permanganate Substances 0.000 claims description 13
- 239000002608 ionic liquid Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- HFLGBNBLMBSXEM-UHFFFAOYSA-N 4-Ethyl-1,2-benzenediol Chemical compound CCC1=CC=C(O)C(O)=C1 HFLGBNBLMBSXEM-UHFFFAOYSA-N 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 6
- MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-N 0.000 claims description 5
- JYLNVJYYQQXNEK-UHFFFAOYSA-N 3-amino-2-(4-chlorophenyl)-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(CN)C1=CC=C(Cl)C=C1 JYLNVJYYQQXNEK-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- SYWXNZXEJFSLEU-UHFFFAOYSA-M lithium;periodate Chemical compound [Li+].[O-]I(=O)(=O)=O SYWXNZXEJFSLEU-UHFFFAOYSA-M 0.000 claims description 4
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract description 16
- 239000006227 byproduct Substances 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- 238000004065 wastewater treatment Methods 0.000 abstract description 2
- 239000004005 microsphere Substances 0.000 description 35
- 230000015556 catabolic process Effects 0.000 description 24
- 238000006731 degradation reaction Methods 0.000 description 24
- 239000007864 aqueous solution Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910021642 ultra pure water Inorganic materials 0.000 description 10
- 239000012498 ultrapure water Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000000149 chemical water pollutant Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000010865 sewage Substances 0.000 description 4
- ZXLOSLWIGFGPIU-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;acetate Chemical compound CC(O)=O.CCN1CN(C)C=C1 ZXLOSLWIGFGPIU-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- PBIDWHVVZCGMAR-UHFFFAOYSA-N 1-methyl-3-prop-2-enyl-2h-imidazole Chemical compound CN1CN(CC=C)C=C1 PBIDWHVVZCGMAR-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000009303 advanced oxidation process reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 231100000693 bioaccumulation Toxicity 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- -1 nitrate ions Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- PVGBHEUCHKGFQP-UHFFFAOYSA-N sodium;n-[5-amino-2-(4-aminophenyl)sulfonylphenyl]sulfonylacetamide Chemical compound [Na+].CC(=O)NS(=O)(=O)C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 PVGBHEUCHKGFQP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 231100000378 teratogenic Toxicity 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Images
Classifications
-
- 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
- C02F1/72—Treatment of water, waste water, or sewage by oxidation
-
- 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
- C02F1/72—Treatment of water, waste water, or sewage by oxidation
- C02F1/76—Treatment of water, waste water, or sewage by oxidation with halogens or compounds of halogens
-
- 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
- C02F2101/38—Organic compounds containing nitrogen
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- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Removal Of Specific Substances (AREA)
Abstract
The invention belongs to the technical field of wastewater treatment, and discloses a composition for selectively degrading aniline pollutants, a preparation method and application thereof. The composition for selectively degrading aniline pollutants comprises a composite material and an oxidant, wherein the composite material comprises cellulose serving as a carrier and a phenolic compound containing two ortho-phenolic hydroxyl groups and loaded in the carrier, and the oxidant comprises periodate and/or permanganate. The invention can selectively oxidize the phenolic compounds containing two ortho-phenolic hydroxyl groups in the composite material by using the oxidant to generate the quinone active species, wherein the quinone active species is an active species which can selectively react with aniline pollutants with strong nucleophilicity and does not react with water quality matrixes, so that the aniline pollutants in the wastewater can be selectively and efficiently removed; meanwhile, the generated quinone byproducts are loaded in the composite material, so that the recovery is convenient, the toxicity of the wastewater is reduced, the composite material has good stability and strong repeatability, and can be recycled.
Description
Technical Field
The invention belongs to the technical field of wastewater treatment, and particularly relates to a composition for selectively degrading aniline pollutants, a preparation method and application thereof.
Background
Aniline is widely used as an important chemical raw material in the industries of dye, medicine, rubber and the like. With the development of industrial level and the increasing demand of chemicals for humans, the demand of aniline increases, resulting in an increase in the concentration of aniline pollutants in the environment. Aniline pollutants with different concentration levels (ng/L-mug/L) are detected in the water environment at present. The aniline pollutant has the characteristics of wide pollution range, multiple types, long half life and high toxicity, can be subjected to cancerogenic, teratogenic and mutagenic risks after being exposed to the environment for a long time, has bioaccumulation and causes irreversible damage to human health.
Although the advanced oxidation process based on hydroxyl radicals, which is recently developed, can remove aniline pollutants with high efficiency, water quality substrates in wastewater affect the removal effect of aniline pollutants, such as chloride ions, carbonate ions, soluble organic matters and the like, can react with the hydroxyl radicals to consume the concentration of the radicals, thereby inhibiting the degradation of the aniline pollutants. Therefore, how to avoid the influence of water quality matrix in the wastewater and improve the removal effect of aniline pollutants in the wastewater is a technical problem to be solved in the field.
Disclosure of Invention
The present invention aims to solve at least one of the technical problems in the prior art described above. Therefore, the invention provides a composition for selectively degrading aniline pollutants, which has the advantage of strong resistance to water quality substrates and can selectively and efficiently remove aniline pollutants in wastewater.
In a first aspect the invention provides a composition for selectively degrading aniline contaminants, comprising a composite material comprising cellulose as a carrier and a phenolic compound containing two ortho phenolic hydroxyl groups supported in the carrier, and an oxidising agent comprising a periodate and/or a permanganate.
Preferably, the periodate salt comprises at least one of sodium periodate, potassium periodate and lithium periodate.
Preferably, the permanganate comprises at least one of potassium permanganate, sodium permanganate, ammonium permanganate.
Preferably, the phenolic compound containing two ortho-phenolic hydroxyl groups comprises at least one of catechol, 4-methyl catechol and 4-ethyl catechol.
The second aspect of the invention provides a preparation method of the composition for selectively degrading aniline pollutants, which comprises the following steps:
dissolving the phenolic compound containing two ortho-phenolic hydroxyl groups and the cellulose in ionic liquid to obtain a mixed solution;
dropping the mixed solution into water such that the mixed solution forms a pre-composite;
washing the pre-composite material with water and drying to obtain a composite material;
and mixing the composite material with the oxidant to obtain the composition for selectively degrading the aniline pollutants.
Preferably, the preparation method of the composition for selectively degrading aniline pollutants comprises the following steps:
the specific process of dissolution comprises the following steps: adding the phenolic compound containing two ortho-phenolic hydroxyl groups and the cellulose into ionic liquid, and stirring for 1-5h at the temperature of 65-95 ℃.
Preferably, the mass ratio of the phenolic compound containing two ortho-phenolic hydroxyl groups to the cellulose is 1 (0.3-3).
Preferably, the concentration of the phenolic compound containing two ortho-phenolic hydroxyl groups in the ionic liquid is 16-140g/L.
Preferably, the number of water flushes is 3-5.
Preferably, the drying temperature is 20-30 ℃.
Preferably, the ionic liquid is 1-allyl-3-methylimidazole chloride or 1-ethyl-3-methylimidazole acetate.
Preferably, the water is ultrapure water.
The third aspect of the invention provides application of the composition for selectively degrading aniline pollutants in preparation of organic wastewater degradation agents.
According to a fourth aspect of the invention, a method for selectively degrading aniline pollutants in wastewater is provided, the composition for selectively degrading aniline pollutants is put into wastewater, the input amount of the composite material is 10-15g/L, and the input amount of the oxidant is 20-40 mu M.
Compared with the prior art, the invention has the following beneficial effects:
in the composition for selectively degrading aniline pollutants, the oxidant can selectively oxidize phenolic compounds containing two ortho-phenolic hydroxyl groups in the composite material to generate quinone active species, wherein the quinone active species are active species which can selectively react with aniline pollutants with strong nucleophilicity and do not react with water quality matrixes, so that the aniline pollutants in the wastewater can be selectively and efficiently removed; because toxic quinone byproducts are generated by the addition reaction of the quinone active species and the aniline pollutants, the invention adopts a mode of a composite material, so that the generated quinone byproducts are loaded in the composite material, the recovery is convenient, the toxicity of wastewater is reduced, the composite material has good stability and strong repeatability, and the composite material can be recycled.
Drawings
The invention is further described below with reference to the drawings and examples.
FIG. 1 is a physical view of the composite material of example 1;
FIG. 2 is a graph of the degradation of aniline by the composition of example 1 and sodium periodate alone or the composite;
FIG. 3 is a graph of the cyclic effect of the composition of example 1 on aniline degradation;
FIG. 4 is a graph of the degradation of aniline in various bodies of water by the composition of example 1;
fig. 5 is a graph of the degradation of aniline by the composition of example 2 and potassium permanganate alone.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples will be presented. It should be noted that the following examples do not limit the scope of the invention.
The starting materials, reagents, apparatus used in the examples below were obtained from conventional commercial sources, unless otherwise specified, or may be obtained by methods known in the art.
Example 1
A composition for selectively degrading aniline contaminants, comprising a composite material and sodium periodate, the composite material comprising cellulose as a carrier and catechol supported in the carrier.
The preparation method of the composition for selectively degrading aniline pollutants comprises the following steps:
(1) 0.5g of alpha-cellulose and 0.5g of catechol are placed in a 50mL brown bottle, 10mL of 1-allyl-3-methylimidazole chloride ionic liquid is added, the mixture is stirred and mixed uniformly by using a rotor, and then the mixed solution is placed in a water bath kettle, heated to 85 ℃ and stirred at constant temperature for 3 hours.
(2) Adding the heated mixed solution into a plastic injector with a specification of 26-G needle, slowly dripping the mixed solution into a 50mL beaker containing ultrapure water at a constant speed by means of external force to prepare a pre-composite material, flushing the pre-composite material with the ultrapure water for 3 times, and drying at 25 ℃ for 24 hours to prepare the composite material (marked as catechol@cellulose microspheres);
(3) The composite material and sodium periodate are mixed to prepare the composition (named sodium periodate/catechol@cellulose microsphere) for selectively degrading aniline pollutants.
As shown in fig. 1, the composite material prepared in this embodiment has regular morphology, uniform particle size, and transparent shape.
Test for degrading aniline pollutants
1. Sodium periodate/catechol@cellulose microspheres degrade aniline in water.
The sodium periodate/catechol@cellulose microspheres provided in example 1, and the degradation effects of the individual sodium periodate, the individual catechol@cellulose microspheres on aniline in 50mL of 5 μm aniline aqueous solution were examined under conditions of ph=7±0.2, solid-to-liquid ratio of catechol@cellulose microspheres to aniline aqueous solution of 10g/L, addition amount of sodium periodate of 20 μm, reaction temperature of 20 ℃, degradation time of 60s, respectively, as shown in fig. 2. As can be seen from fig. 2, when sodium periodate is added alone, the degradation of aniline within 60s is 0; when catechol@cellulose microspheres are independently added, the degradation of aniline within 60 seconds is 0; when sodium periodate/catechol @ cellulose microspheres were added, the aniline was completely degraded after 60s of reaction. The sodium periodate and catechol@cellulose microspheres are combined to efficiently degrade aniline in a water body.
2. And (3) a circulating experiment for degrading aniline in the water body by using sodium periodate/catechol@cellulose microspheres.
Under the conditions that the pH=7+/-0.2, the solid-to-liquid ratio of catechol@cellulose microspheres to an aniline aqueous solution is 10g/L, the adding amount of sodium periodate is 20 mu M, the reaction temperature is 20 ℃, and the degradation time is 60s, the recycling property of the catechol@cellulose microspheres after the sodium periodate/catechol@cellulose microspheres provided in the example 1 are degraded in 150mL of 5 mu M aniline aqueous solution is examined. After each degradation, catechol @ cellulose microspheres were fished out and rinsed 3 times with ultra pure water and dried at room temperature for 24 hours before the next use, as shown in fig. 3. As can be seen from FIG. 3, the experiment of adding sodium periodate and catechol @ cellulose microsphere was repeated 5 times, and after each cycle of reaction for 60 seconds, the aniline was completely degraded. The experiment shows that the catechol@cellulose microsphere has good reusability.
3. Sodium periodate/catechol@cellulose microspheres degrade aniline in an actual water body.
Under the conditions that the solid-to-liquid ratio of catechol@cellulose microspheres to aqueous aniline solution is 10g/L, the adding amount of sodium periodate is 40 mu M, the reaction temperature is 20 ℃, and the degradation time is 60s, the degradation effect of the sodium periodate/catechol@cellulose microspheres provided in example 1 on aniline in 50mL of 5 mu M aniline different actual aqueous solutions (river water, sewage and landfill leachate) is examined, and the water bodies contain chloride ions, carbonate ions, sulfate ions, bromide ions, nitrate ions, soluble organic matters and the like, and ultrapure water is used as a control. As shown in fig. 4. As can be seen from FIG. 4, sodium periodate and catechol@cellulose microspheres are respectively added into river water, sewage and landfill leachate containing aniline, and the aniline can be completely degraded after 60 seconds of reaction. The sodium periodate and catechol@cellulose microspheres can degrade aniline in different actual water bodies with high efficiency, and are not influenced by water quality matrixes basically.
Example 2
A composition for selectively degrading aniline pollutants, comprising a composite material and potassium permanganate, wherein the composite material comprises cellulose serving as a carrier and catechol loaded in the carrier.
The preparation method of the composition for selectively degrading aniline pollutants comprises the following steps:
(1) 0.25g of alpha-cellulose and 0.7g of catechol are placed in a 50mL brown bottle, 5mL of 1-ethyl-3-methylimidazole acetate ionic liquid is added, the mixture is stirred and mixed uniformly by using a rotor, and then the mixed solution is placed in a water bath kettle, heated to 65 ℃ and stirred at constant temperature for 5 hours.
(2) Adding the heated mixed solution into a plastic injector with a specification of 26-G needle, slowly dripping the mixed solution into a 50mL beaker containing ultrapure water at a constant speed by means of external force to prepare a pre-composite material, flushing the pre-composite material with the ultrapure water for 3 times, and drying at 20 ℃ for 24 hours to prepare the composite material (marked as catechol@cellulose microspheres);
(3) The composite material and potassium permanganate are mixed to prepare the composition (marked as potassium permanganate/catechol@cellulose microsphere) for selectively degrading aniline pollutants.
And (3) testing the degradation of the aniline in the water body by the potassium permanganate/catechol@cellulose microspheres.
Under the conditions of ph=7±0.2, solid-to-liquid ratio of catechol@cellulose microspheres to aniline aqueous solution of 10g/L, addition amount of potassium permanganate of 20 μm, reaction temperature of 20 ℃, degradation time of 60s, the potassium permanganate/catechol@cellulose microspheres provided in example 2 and degradation effect of individual potassium permanganate on aniline in 50mL of 5 μm aniline aqueous solution were examined, respectively, as shown in fig. 5. As can be seen from fig. 5, when potassium permanganate was dosed alone, the degradation of aniline within 60s was 0; when potassium permanganate/catechol@cellulose microspheres are added, the aniline is completely degraded after 60s of reaction. The potassium permanganate and catechol@cellulose microspheres can be used for efficiently degrading the aniline in the water body.
Example 3
A composition for selectively degrading aniline contaminants, comprising a composite material and potassium periodate, the composite material comprising cellulose as a carrier and catechol supported in the carrier.
The preparation method of the composition for selectively degrading aniline pollutants comprises the following steps:
(1) 0.7g of alpha-cellulose and 0.25g of catechol are placed in a 50mL brown bottle, 15mL of 1-ethyl-3-methylimidazole acetate ionic liquid is added, the mixture is stirred and mixed uniformly by using a rotor, and then the mixed solution is placed in a water bath kettle, heated to 95 ℃ and stirred at constant temperature for 1 hour.
(2) Adding the heated mixed solution into a plastic injector with a specification of 26-G needle, slowly dripping the mixed solution into a 50mL beaker containing ultrapure water at a constant speed by means of external force to prepare a pre-composite material, flushing the pre-composite material with the ultrapure water for 5 times, and drying at 30 ℃ for 24 hours to prepare the composite material (marked as catechol@cellulose microspheres);
(3) The composite material and potassium periodate are mixed to prepare the composition (marked as potassium periodate/catechol@cellulose microsphere) for selectively degrading aniline pollutants.
Example 4
The difference from example 1 is that example 4 replaces sodium periodate with lithium periodate and the other components and preparation method are the same as example 1. The composition provided in example 4 for selectively degrading aniline contaminants is designated lithium periodate/catechol @ cellulose microspheres.
Example 5
The difference from example 1 is that example 5 replaces sodium periodate with sodium permanganate and the other components and preparation method are the same as example 1. The composition provided in example 5 for selectively degrading aniline contaminants is designated sodium permanganate/catechol @ cellulose microspheres.
Example 6
The difference from example 1 is that example 6 replaces sodium periodate with ammonium permanganate and the other components and preparation method are the same as example 1. The composition provided in example 6 for selectively degrading aniline contaminants is designated ammonium permanganate/catechol @ cellulose microspheres.
Example 7
The difference from example 1 is that example 7 replaces catechol with 4-methylcatechol, and other components and preparation methods are the same as example 1. The composition for selectively degrading aniline contaminants provided in example 7 is designated sodium periodate/4-methylcatechol @ cellulose microsphere.
Example 8
The difference from example 1 is that example 8 replaces catechol with 4-ethyl catechol, and other components and preparation methods are the same as example 1. The composition provided in example 8 for selectively degrading aniline contaminants is designated sodium periodate/4-ethyl catechol @ cellulose microspheres.
Test for degrading aniline pollutants
1. Under the conditions that the pH=7+/-0.2, the solid-to-liquid ratio of the composite material to the aniline aqueous solution is 10g/L, the addition amount of the oxidant is 20 mu M, the reaction temperature is 20 ℃, and the degradation time is 60s, the degradation effect of the composition for selectively degrading the aniline pollutants provided in the examples 3-8 on aniline in 50mL of 5 mu M aniline aqueous solution is examined respectively.
Test results: when the compositions for selectively degrading aniline pollutants provided in examples 3 to 8 are respectively added, the aniline can be completely degraded after 60 seconds of reaction. The composition for selectively degrading aniline pollutants provided by the invention can be used for degrading aniline in water with high efficiency.
2. Under the conditions that the pH=7+/-0.2, the solid-to-liquid ratio of the composite material to the aniline aqueous solution is 10g/L, the addition amount of the oxidant is 20 mu M, the reaction temperature is 20 ℃, and the degradation time is 60s, the recyclability of the composite material provided in the examples 3-8 after the composite material is degraded to aniline in 150mL of 5 mu M aniline aqueous solution is examined respectively. After each degradation, the composite material was fished out and rinsed 3 times with ultrapure water, dried at room temperature for 24 hours and then ready for the next use.
Test results: the addition experiment of the composite material provided in examples 3-8 was repeated 5 times, and after 60s of each cyclic reaction, the aniline was completely degraded. The composite material provided by the invention has good reusability.
3. Under the conditions that the solid-to-liquid ratio of the composite material to the aniline aqueous solution is 15g/L, the addition amount of the oxidant is 40 mu M, the reaction temperature is 20 ℃, and the degradation time is 60s, the degradation effects of the composition for selectively degrading aniline pollutants provided in examples 3-8 on aniline in 50mL of 5 mu M aniline different actual aqueous solutions (river water, sewage and landfill leachate) are examined respectively.
Test results: the composition for selectively degrading the aniline pollutants provided in examples 3-8 is respectively added into river water, sewage and landfill leachate containing aniline, and the aniline can be completely degraded after reacting for 60 seconds. The composition for selectively degrading the aniline pollutants can degrade aniline in different actual water bodies with high efficiency, and is basically not influenced by water quality matrixes.
While the preferred embodiments of the present invention have been illustrated and described, the present invention is not limited to the embodiments, and various equivalent modifications and substitutions can be made by one skilled in the art without departing from the spirit of the present invention, and these are intended to be included in the scope of the present invention as defined in the appended claims.
Claims (10)
1. A composition for selectively degrading aniline contaminants, comprising a composite material comprising cellulose as a carrier and a phenolic compound containing two ortho phenolic hydroxyl groups supported in the carrier, and an oxidizing agent comprising periodate and/or permanganate.
2. The composition for selectively degrading aniline contaminants according to claim 1, wherein the periodate salt includes at least one of sodium periodate, potassium periodate, lithium periodate.
3. The composition for selectively degrading aniline contaminants of claim 1, wherein the permanganate salt includes at least one of potassium permanganate, sodium permanganate, ammonium permanganate.
4. The composition for selectively degrading aniline contaminants according to claim 1, characterized in that the phenolic compound containing two ortho phenolic hydroxyl groups includes at least one of catechol, 4-methyl catechol, 4-ethyl catechol.
5. A method for preparing a composition for selectively degrading aniline contaminants according to any one of claims 1 to 4, comprising the steps of:
dissolving the phenolic compound containing two ortho-phenolic hydroxyl groups and the cellulose in ionic liquid to obtain a mixed solution;
dropping the mixed solution into water such that the mixed solution forms a pre-composite;
washing the pre-composite material with water and drying to obtain a composite material;
and mixing the composite material with the oxidant to obtain the composition for selectively degrading the aniline pollutants.
6. The method of manufacturing according to claim 5, comprising the steps of:
the specific process of dissolution comprises the following steps: adding the phenolic compound containing two ortho-phenolic hydroxyl groups and the cellulose into ionic liquid, and stirring for 1-5h at the temperature of 65-95 ℃.
7. The method according to claim 5, wherein the mass ratio of the phenolic compound containing two ortho-phenolic hydroxyl groups to the cellulose is 1 (0.3-3).
8. The method according to claim 5, wherein the concentration of the phenolic compound containing two ortho-phenolic hydroxyl groups in the ionic liquid is 16-140g/L.
9. Use of a composition for selectively degrading aniline contaminants according to any one of claims 1-4 in the preparation of an organic wastewater degrading agent.
10. A method for selectively degrading aniline pollutants in wastewater, which is characterized in that the composition for selectively degrading aniline pollutants according to any one of claims 1-4 is put into wastewater, the input amount of the composite material is 10-15g/L, and the input amount of the oxidant is 20-40 mu M.
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