CN111704225A - Photocatalytic oxidation treatment process for wastewater containing dimethyl sulfoxide through photosensitizer under visible light - Google Patents
Photocatalytic oxidation treatment process for wastewater containing dimethyl sulfoxide through photosensitizer under visible light Download PDFInfo
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- CN111704225A CN111704225A CN202010420235.1A CN202010420235A CN111704225A CN 111704225 A CN111704225 A CN 111704225A CN 202010420235 A CN202010420235 A CN 202010420235A CN 111704225 A CN111704225 A CN 111704225A
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- dimethyl sulfoxide
- photosensitizer
- visible light
- hydrogen peroxide
- oxidation treatment
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 239000003504 photosensitizing agent Substances 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 21
- 230000003647 oxidation Effects 0.000 title claims abstract description 18
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 18
- 239000002351 wastewater Substances 0.000 title claims abstract description 17
- 230000001699 photocatalysis Effects 0.000 title claims abstract description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 46
- QQNLHOMPVNTETJ-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene] Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 QQNLHOMPVNTETJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims abstract description 16
- NTGBUUXKGAZMSE-UHFFFAOYSA-N phenyl n-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]carbamate Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(NC(=O)OC=3C=CC=CC=3)=CC=2)CC1 NTGBUUXKGAZMSE-UHFFFAOYSA-N 0.000 claims abstract description 12
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 241000282376 Panthera tigris Species 0.000 claims abstract description 5
- 229960000907 methylthioninium chloride Drugs 0.000 claims abstract description 5
- 229940043267 rhodamine b Drugs 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 abstract description 6
- 230000000977 initiatory effect Effects 0.000 abstract description 4
- 239000003403 water pollutant Substances 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 16
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 10
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000005286 illumination Methods 0.000 description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000005388 borosilicate glass Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010812 external standard method Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009303 advanced oxidation process reaction Methods 0.000 description 1
- WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000010887 waste solvent Substances 0.000 description 1
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
- C02F1/725—Treatment of water, waste water, or sewage by oxidation by catalytic 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
- C02F1/722—Oxidation by peroxides
-
- 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
- C02F2101/10—Inorganic compounds
- C02F2101/101—Sulfur compounds
Abstract
The invention belongs to the technical field of water pollutant purification treatment, and particularly relates to a process for carrying out photocatalytic oxidation treatment on dimethyl sulfoxide-containing wastewater by using a photosensitizer under visible light, wherein the photosensitizer and hydrogen peroxide are used for treating a water body containing dimethyl sulfoxide under the visible light, the photosensitizer comprises tiger red, rhodamine, methylene blue, nuclear fast red and spiro [ fluorene-9, 9' -xanthene ], and the mass ratio of the photosensitizer to the dimethyl sulfoxide in the water body is 0.5-1: 100. the photosensitizers themselves generate initiating free radicals after absorbing visible light, and the generated initiating free radicals can exchange with hydrogen peroxide to decompose the hydrogen peroxide into oxidizing free radicals to react with dimethyl sulfoxide.
Description
Technical Field
The invention belongs to the technical field of water pollutant purification treatment, and particularly relates to a photocatalytic oxidation treatment process for dimethyl sulfoxide-containing wastewater by using a photosensitizer under visible light.
Background
Dimethyl sulfoxide (DMSO) is a sulfur-containing polar aprotic organic solvent, can be mutually soluble with most organic solvents such as ethanol, toluene and chloroform and water at any ratio, has the characteristics of good solubility, high boiling point, no toxicity and the like, and is widely used in the industries such as petrochemical industry, artificial fibers, printing and dyeing, drug synthesis and the like. Although dimethyl sulfoxide is non-toxic, it can carry dissolved toxic substances into water and organisms, causing poisoning, and thus dimethyl sulfoxide in water needs to be separated from water even if it is present in a small amount.
The biochemical treatment of the dimethyl sulfoxide is difficult, and the wastewater generated by the process adopting the dimethyl sulfoxide as a raw material or an auxiliary material is high in Chemical Oxygen Demand (COD) and poor in biodegradability, and is easy to degrade into compounds with strong toxicity, such as dimethyl sulfide, methyl mercaptan, hydrogen sulfide and the like, due to the biochemical treatment, so that secondary pollution is easily caused. While the conventional reduced pressure distillation can effectively recover the high-concentration dimethyl sulfoxide waste solvent, the dimethyl sulfoxide has a high boiling point (the boiling point is 189 ℃ at normal pressure), about 1 percent of dimethyl sulfoxide has disproportionation reaction at the temperature of more than 90 ℃ to generate dimethyl sulfone and dimethyl sulfide with foul smell, so that the recovered dimethyl sulfoxide has poor quality and can be used after further purification.
For low-concentration dimethyl sulfoxide waste water, the traditional extraction, adsorption and separation method has poor effect due to strong association between dimethyl sulfoxide and water molecules.
Compared with a plurality of treatment methods of the dimethyl sulfoxide wastewater, one of the feasible treatment methods is an advanced oxidation method, and the method is characterized in that hydrogen peroxide is added into the dimethyl sulfoxide wastewater, and the wastewater is subjected to ultraviolet light illumination, so that the dimethyl sulfoxide is oxidized into the dimethyl sulfone which is easy to carry out biochemical treatment (the generated dimethyl sulfone is low in quantity and easy to be further oxidized, so that the residual quantity is lower, the degree of bringing other toxic substances into the dimethyl sulfone is far less than that of the dimethyl sulfoxide, the dimethyl sulfone can not be considered), methanesulfonic acid, sulfuric acid, formaldehyde and the like, malodorous and virulent compounds such as dimethyl sulfide, methyl mercaptan, hydrogen sulfide and the like can not be generated, and the green and environment-friendly industrial waste treatment requirement is met.
However, the ultraviolet light/hydrogen peroxide advanced oxidation process of the dimethyl sulfoxide wastewater is not widely applied, and has two defects: one is the generating device of ultraviolet light, and this type of device often consumes energy highly, and effectual ultraviolet band intensity is not enough in the spectrum, and most wavelength is not in the absorption wavelength range of hydrogen peroxide in the illumination for a large amount of energy is wasted in the illumination, and efficiency reduces, and its second is rigorous equipment light transmissivity requirement, has experimental study to show that hydrogen peroxide can decompose into HO and HO in a large number under UV-B and UV-C ultraviolet illumination into HO and HO under the illumination of UV-B and UV-C ultraviolet2The high oxidation active free radicals, but the UV-B and UV-C wave band purple can be transmitted only by using a glass container made of expensive quartz glass materials with high processing difficulty, so that the equipment processing becomes a threshold which is difficult to exceed by the process.
Disclosure of Invention
In order to solve the technical problems, the invention provides a process for carrying out photocatalytic oxidation treatment on waste water containing dimethyl sulfoxide by using a photosensitizer under visible light, the photosensitizer and hydrogen peroxide are used for treating water containing dimethyl sulfoxide under the irradiation of visible light,
wherein the photosensitizer comprises one or a combination of more of tiger red, rhodamine, methylene blue, nuclear fast red and spiro [ fluorene-9, 9' -xanthene ], the photosensitizers generate initiation free radicals after absorbing visible light, and the generated initiation free radicals can exchange with hydrogen peroxide to decompose the hydrogen peroxide into oxidation free radicals to further react with dimethyl sulfoxide,
preferably, the method comprises the following steps: the photosensitizer is rhodamine B, nuclear fast red, spiro [ fluorene-9, 9' -xanthene ] and the photosensitizer is prepared by mixing the following components in percentage by weight of 1.7-2.1: 2.2-2.4: 0.9-1.2 by mass ratio,
in terms of dosage, the mass ratio of the photosensitizer to the dimethyl sulfoxide in the water body is 0.5-1: 100,
the solute mass fraction of the hydrogen peroxide in the hydrogen peroxide is 10-30 percent,
the mass ratio of the hydrogen peroxide to the dimethyl sulfoxide in the water body is 150-200: 100.
Detailed Description
Example 1
A single photosensitizer was used:
250mL of DMSO aqueous solution (wherein the volume ratio of DMSO to water when mixing is 1: 99, that is, the initial concentration of DMSO in the aqueous solution is 11mg/mL) is added to a 500mL high borosilicate glass three-necked bottle, 35nmol of photosensitizer and 10g of hydrogen peroxide (hydrogen peroxide is 3g, 88.2mmol) with a solute mass fraction of hydrogen peroxide are added to the aqueous solution, and after sufficient stirring at room temperature (25 ℃, the same applies below), the mixture is kept in a stirring state and irradiated by a 400-watt metal halide lamp (Philips HPI-plus-BUS400W) (the irradiation light emitted by the metal halide lamp can be basically considered as the effect of natural light with the ultraviolet band removed), and the irradiation is continued for 24 hours, wherein samples are taken every 3 hours, and the DMSO concentration in the sampled water body is measured at 254nm by using an HPLC external standard method.
Different single photosensitizers were selected in turn, and the treatment effect data are shown in table 1.
Example 2
Adopts rhodamine B, nuclear fast red and spiro [ fluorene-9, 9' -xanthene ] according to the proportion of 10: 17: 8 (the total addition of the photosensitizers is still 35 nmol: 10nmol for rhodamine B, 17nmol for nuclear fast red, 8nmol for spiro [ fluorene-9, 9' -xanthene ]), and the rest of the operations are the same as in example 1.
The treatment effect data are shown in table 1.
Example 3
Rhodamine B and spiro [ fluorene-9, 9' -xanthene ] are adopted according to the proportion of 20: 15 (the total addition of the photosensitizers is still 35 nmol: rhodamine B20nmol, spiro [ fluorene-9, 9' -xanthene ]15nmol), and the rest of the operations are the same as in example 1.
The treatment effect data are shown in table 1.
Example 4
The compound is prepared from tiger red, nuclear fast red, spiro [ fluorene-9, 9' -xanthene ] according to the weight ratio of 10: 17: 8 (the total amount of the photosensitizer added is still 35 nmol: i.e. 10nmol of tiger red, 17nmol of fast red, 8nmol of spiro [ fluorene-9, 9' -xanthene ], etc.), and the rest of the operations are the same as in example 1.
The treatment effect data are shown in table 1.
Comparative example 1
Azure was chosen as the single photosensitizer (addition 35nmol) and the rest of the procedure was the same as in example 1. The treatment effect data are shown in table 1.
TABLE 1
Example 5
250mL of DMSO aqueous solution (wherein the volume ratio of DMSO to water when mixing is 1: 99, namely the initial concentration of DMSO in the aqueous solution is 11mg/mL) is added into a 500mL high borosilicate glass three-necked bottle, 32nmol of photosensitizer and 10g of hydrogen peroxide (hydrogen peroxide is 3g, 88.2mmol) with the solute mass fraction of hydrogen peroxide are added into the aqueous solution, the stirring state is kept after the mixture is fully stirred at room temperature (25 ℃, the same applies below), the mixture is irradiated by natural light for 5 days (depending on illumination in the day), wherein samples are taken every other day (24 hours), and the DMSO concentration in the sampled water body is measured at 254nm by using an HPLC external standard method.
Different single photosensitizers were selected in turn, and the treatment effect data are shown in table 2.
Example 6
Adopts rhodamine B, nuclear fast red and spiro [ fluorene-9, 9' -xanthene ] according to the proportion of 10: 15: 7 (the total addition of the photosensitizers is still 32 nmol: 10nmol for rhodamine B, 15mol for nuclear fast Red, 7nmol for Spiro [ fluorene-9, 9' -xanthene ]), and the rest of the operations are the same as those in example 5.
The treatment effect data are shown in table 2.
Example 7
Adopting rhodamine B and nuclear fixation according to the weight ratio of 10: 22 (the total addition of the photosensitizer is still 32 nmol: namely rhodamine B10nmol, nuclear fast Red 22mol), and the rest of the operations are the same as those in example 5.
The treatment effect data are shown in table 2.
Example 8
Adopting rhodamine B, methylene blue and spiro [ fluorene-9, 9' -xanthene ] according to the proportion of 10: 15: 7 (the total addition of the photosensitizers is still 32 nmol: 10nmol for rhodamine B, 15nmol for methylene blue, 7nmol for spiro [ fluorene-9, 9' -xanthene ]), and the rest of the operations are the same as in example 5.
The treatment effect data are shown in table 2.
Comparative example 2
Azure was chosen as the single photosensitizer (added in 32nmol) and the rest of the procedure was the same as in example 5. The treatment effect data are shown in table 2.
TABLE 2
Based on the purification effects in tables 1 and 2, when various photosensitizers are used alone, the catalytic oxidation effects of the photosensitizers are relatively close to each other under natural light irradiation (as shown in table 2), but under the irradiation of a metal halide lamp, the catalytic oxidation effect of spiro [ fluorene-9, 9' -xanthene ] is obviously better than that of other four photosensitizers, and the catalytic oxidation speed is higher (as shown in table 1);
when several photosensitizers are used in a matched manner, three photosensitizers, namely rhodamine B, nuclear fast red and spiro [ fluorene-9, 9' -xanthene ], are used together (example 2 and example 6), and on the basis of the same dosage of the photosensitizers, compared with the single use of any photosensitizer, the photosensitizer has obvious advantages in catalytic oxidation speed and purification degree; however, if the three photosensitizers are not compounded, the purification effect is not necessarily good, as in example 3, example 4, example 7 and example 8.
Claims (6)
1. A process for carrying out photocatalytic oxidation treatment on waste water containing dimethyl sulfoxide by a photosensitizer under visible light is characterized by comprising the following steps: the treatment process is that the water body containing the dimethyl sulfoxide is treated by using a photosensitizer and hydrogen peroxide under the irradiation of visible light.
2. The process of claim 1 for photocatalytic oxidation treatment of waste water containing dimethyl sulfoxide by means of a photosensitizer under visible light, characterized in that: the photosensitizer comprises one or more of tiger red, rhodamine, methylene blue, nuclear fast red and spiro [ fluorene-9, 9' -xanthene ].
3. The process of claim 2 for photocatalytic oxidation treatment of waste water containing dimethyl sulfoxide by means of a photosensitizer under visible light, characterized in that: the photosensitizer is rhodamine B, nuclear fast red, spiro [ fluorene-9, 9' -xanthene ] and is prepared by mixing the following raw materials in a proportion of 1.7-2.1: 2.2-2.4: 0.9-1.2 by mass ratio.
4. The process of claim 1 for photocatalytic oxidation treatment of waste water containing dimethyl sulfoxide by means of a photosensitizer under visible light, characterized in that: the mass ratio of the photosensitizer to the dimethyl sulfoxide in the water body is 0.5-1: 100.
5. the process of claim 1 for photocatalytic oxidation treatment of waste water containing dimethyl sulfoxide by means of a photosensitizer under visible light, characterized in that: the solute mass fraction of the hydrogen peroxide in the hydrogen peroxide is 10-30%.
6. The process of claim 1 for photocatalytic oxidation treatment of waste water containing dimethyl sulfoxide by means of a photosensitizer under visible light, characterized in that: the mass ratio of the hydrogen peroxide to the dimethyl sulfoxide in the water body is 150-200: 100.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113234184A (en) * | 2021-05-18 | 2021-08-10 | 深圳大学 | Methylene blue photosensitizer and application thereof in photo-Fenton-initiated RAFT reaction |
CN115385415A (en) * | 2022-07-07 | 2022-11-25 | 江苏理工学院 | Method for degrading organic wastewater by using waste to treat waste |
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US4008136A (en) * | 1974-08-09 | 1977-02-15 | Temple University | Process for the treatment of waste water by heterogeneous photosensitized oxidation |
CN101721988A (en) * | 2009-12-02 | 2010-06-09 | 南开大学 | Photocatalyst for treating methylene blue dye wastewater, preparation method thereof and application thereof |
CN102491450A (en) * | 2011-12-15 | 2012-06-13 | 南京大学 | Method for treating dye waste water by using ultraviolet-acetylacetone oxidation treatment process |
CN103318998A (en) * | 2013-06-19 | 2013-09-25 | 环境保护部华南环境科学研究所 | Novel treatment method for pentachlorophenol-containing wastewater |
CN109721128A (en) * | 2019-01-04 | 2019-05-07 | 南京林业大学 | A method of based on nitrate anion/nitrite anions photocatalytic degradation Organic substance in water |
CN110171866A (en) * | 2019-06-12 | 2019-08-27 | 河南大学 | A kind of Congo red and crystal violet organic pollutant processing method |
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2020
- 2020-05-18 CN CN202010420235.1A patent/CN111704225A/en active Pending
Patent Citations (6)
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US4008136A (en) * | 1974-08-09 | 1977-02-15 | Temple University | Process for the treatment of waste water by heterogeneous photosensitized oxidation |
CN101721988A (en) * | 2009-12-02 | 2010-06-09 | 南开大学 | Photocatalyst for treating methylene blue dye wastewater, preparation method thereof and application thereof |
CN102491450A (en) * | 2011-12-15 | 2012-06-13 | 南京大学 | Method for treating dye waste water by using ultraviolet-acetylacetone oxidation treatment process |
CN103318998A (en) * | 2013-06-19 | 2013-09-25 | 环境保护部华南环境科学研究所 | Novel treatment method for pentachlorophenol-containing wastewater |
CN109721128A (en) * | 2019-01-04 | 2019-05-07 | 南京林业大学 | A method of based on nitrate anion/nitrite anions photocatalytic degradation Organic substance in water |
CN110171866A (en) * | 2019-06-12 | 2019-08-27 | 河南大学 | A kind of Congo red and crystal violet organic pollutant processing method |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN113234184A (en) * | 2021-05-18 | 2021-08-10 | 深圳大学 | Methylene blue photosensitizer and application thereof in photo-Fenton-initiated RAFT reaction |
CN115385415A (en) * | 2022-07-07 | 2022-11-25 | 江苏理工学院 | Method for degrading organic wastewater by using waste to treat waste |
CN115385415B (en) * | 2022-07-07 | 2023-11-10 | 江苏理工学院 | Method for treating waste and degrading organic waste water by waste |
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