CN107235908A - A kind of methyl orange degradation agent and preparation method thereof - Google Patents
A kind of methyl orange degradation agent and preparation method thereof Download PDFInfo
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- CN107235908A CN107235908A CN201710478704.3A CN201710478704A CN107235908A CN 107235908 A CN107235908 A CN 107235908A CN 201710478704 A CN201710478704 A CN 201710478704A CN 107235908 A CN107235908 A CN 107235908A
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- methyl orange
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- 0 C*c1c(**)c(C(N(C(C)(C)C(C)(C)*)O)=[N+]O)c(C)c(*)c1* Chemical compound C*c1c(**)c(C(N(C(C)(C)C(C)(C)*)O)=[N+]O)c(C)c(*)c1* 0.000 description 3
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
-
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/26—Radicals substituted by carbon atoms having three bonds to hetero atoms
-
- 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
- C02F2101/308—Dyes; Colorants; Fluorescent agents
-
- 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
- C02F2101/34—Organic compounds containing oxygen
-
- 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
-
- 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
- C02F2101/40—Organic compounds containing sulfur
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Removal Of Specific Substances (AREA)
Abstract
The present invention provides a kind of methyl orange degradation agent and preparation method thereof, and the current waste water from dyestuff of class containing methyl orange has the characteristics of complicated component, colourity are high, discharge capacity is big, toxicity is big, biodegradability is poor, is always the problem in wastewater treatment.And NO free radical is that the class containing C, N, O and the single electron that spins has rock-steady structure organic compound in the degradation agent that the present invention is provided, the synthesis of compound is respectively with R1~R5Substituted benzaldehyde is raw material, and 2, the dihydroxy amido butane of 3 dimethyl 2,3 carries out condensation and formed.It can be carried out under its organic matter that can directly attack in waste water, normal temperature and pressure, easy to implement, the methyl orange in the dyeing waste water that quickly can thoroughly degrade, oxidation efficiency is high, decomposition rate is fast, will not produce secondary pollution；Configure technique simply inexpensive, and substantial amounts of fund purchase of equipment need not be put into and occupation of land is founded the factory, economize on resources fund.
Description
Technical field
The invention belongs to environmental protection technical field, specific a kind of methyl orange degradation agent and preparation method thereof.
Background technology
China's water pollution situation is on the rise, and existing Treatment process and facility are badly in need of renovating, some new and high technologies
Its development at home is limited because running expense is too high.In 129 kinds of basic pollutants that EPA announces, there is 9
Class totally 114 kinds be organic pollution.Wherein, organic dyestuff methyl orange is organic as typical highly difficult difficult degradation in industrial wastewater
Pollutant.The waste water from dyestuff of class containing methyl orange has complicated component, colourity height, the spy that discharge capacity is big, toxicity is big, biodegradability is poor
Point, is always the problem in wastewater treatment.
Current methyl orange class dye wastewater treatment includes biological treatment and materialization treatment process.Bioanalysis passes through biological suction
Attached, air stripping microorganism, the synthesis for carrying out neoblast material, consume and degrade.Biological treatment has operating cost low, easily
Again big with floor space in the advantage of management, but simultaneously, investment cost is high, is limited by waste component and concentration, during stop
Between it is long the shortcomings of.Materialization treatment process mainly has:Coagulant sedimentation, absorption method, chemical oxidization method etc., current most widely used side
Method is photocatalytic oxidation, and great potentiality are shown in dye wastewater treatment.Photocatalytic oxidation, which is mainly, makes oxidant
Decomposition is worked, and is promoted oxidant to occur chain reaction and is produced the group or ion of high oxidative, organic in attack waste water
Thing.Suitable for there is bio-toxicity and difficult degradation organic pollution, most of hardly degraded organic substances can be made to aoxidize or be coupled.Light
Catalytic degradation technology has can be carried out under normal temperature and pressure, can thoroughly destroy organic matter, and oxidation efficiency is high, and decomposition rate is fast, does not have
There is secondary pollution, but medicament is costly, and reaction unit is more complicated, and processing cost is higher.
The content of the invention
In view of this, it is an object of the invention to provide a kind of methyl orange degradation agent and preparation method thereof, can effectively reduce because
Reaction unit is more complicated, causes the problem of processing cost is higher.
The present invention provides a kind of methyl orange degradation agent, and its structure is as shown in logical formula (I)：
R in logical formula (I)1~R5Respectively NO2、OH、H、OCH3、OCH2CH3、
CF3, one kind in COOH or halogen.
R in the logical formula (I)1~R5In any three substituents be H.
R in the logical formula (I)1~R5Middle any four substituent is H.
The halogen is F, Cl or Br.
A kind of preparation method of methyl orange degradation agent, it is characterised in that：By 2.0mmol2,3- dimethyl -2,3- dihydroxylamines
Base butane is dissolved in 40ml and refined in methanol, is stirred at room temperature, and adds 1.0mmol with R1~R5In substituted benzaldehyde, back flow reaction
There is white precipitate precipitation in 24h, solution, methanol is removed under reduced pressure, residue is suspended in 20mlCH2Cl2In, ice-water bath cooling will
2.8mmolNaIO4It is dissolved in 5ml water, is stirred vigorously down and is slowly added into reaction system, drop continues to react 0.5h after finishing, and stops
Only react, organic phase is washed with water once, takes organic phase to be dried with anhydrous magnesium sulfate, solvent is evaporated off and obtains blue grease, column chromatography
Isolated blue powder.
Application of the described methyl orange degradation agent in Wastewater Dyes methyl orange degradation.
Compared with prior art, the beneficial effects of the invention are as follows：
NO free radical is that the class containing C, N, O and the single electron that spins has rock-steady structure in the degradation agent that the present invention is provided
It can be carried out under organic compound, its organic matter that can directly attack in waste water, normal temperature and pressure, it is easy to implement, can be fast
Methyl orange in speed thoroughly degraded dyeing waste water, oxidation efficiency is high, and decomposition rate is fast, and itself is nontoxic, will not produce secondary
Pollution；Configure technique simply inexpensive, and substantial amounts of fund purchase of equipment need not be put into and occupation of land is founded the factory, economize on resources fund.
Brief description of the drawings
Fig. 1 is degraded figure of the compound 1 to methyl orange of embodiment 1；
Fig. 2 is degraded figure of the compound 4 to methyl orange of embodiment 3.
Embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, it is right below in conjunction with drawings and Examples
The present invention is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, and
It is not used in the restriction present invention.
A kind of methyl orange degradation agent, its structure is as shown in logical formula (I)：
R in logical formula (I)1~R5Respectively NO2、OH、H、OCH3、OCH2CH3、CF3, one kind in COOH or halogen.It is described
Halogen is F, Cl or Br.
The synthesis of above-claimed cpd is respectively with R1~R5Substituted benzaldehyde is raw material, with 2,3- dimethyl -2,3- dihydroxylamines
Base butane carries out condensation and formed, for example：
With reference to said synthesis route, it can synthesize and obtain following structure medicaments：
Degrading experiment is proved：Such reagent has obvious degradation, and medicine poison to Pollutants in Wastewater methyl orange
Property is low.
A kind of preparation method of methyl orange degradation agent, specifically includes following step：By 2.0mmol2,3- dimethyl -2,3-
Dihydroxy amido butane is dissolved in 40ml and refined in methanol, is stirred at room temperature, and adds 1.0mmol with R1~R5In substituted benzaldehyde, backflow
Reacting in 24h, solution has white precipitate precipitation, methanol is removed under reduced pressure, residue is suspended in 20mlCH2Cl2In, ice-water bath cooling,
By 2.8mmolNaIO4It is dissolved in 5ml water, is stirred vigorously down and is slowly added into reaction system, drop continues to react 0.5h after finishing,
Stop reaction, organic phase is washed with water once, takes organic phase to be dried with anhydrous magnesium sulfate, solvent is evaporated off and obtains blue grease, post layer
Analyse isolated blue powder.Embodiment 1：The synthesis of compound 1
300mg (2.0mmol) 2,3- dimethyl -2,3- dihydroxy amido butane is dissolved in into 40ml to refine in methanol, room temperature is stirred
Mix, adding in 122mg (1.0mmol) parahydroxyben-zaldehyde, back flow reaction 24h, solution has white precipitate precipitation, and first is removed under reduced pressure
Alcohol, residue is suspended in 20mlCH2Cl2In, ice-water bath cooling, by 600mg (2.8mmol) NaIO4It is dissolved in 5ml water, acutely stirs
Mix down and be slowly added into reaction system, drop continues to react 0.5h after finishing, and stops reaction, organic phase is washed with water once, taken organic
Dried with anhydrous magnesium sulfate, solvent is evaporated off and obtains blue grease.Column chromatography for separation obtains blue powder 294mg.
Rf=0.3 (CHCl3/CH3OH,20:1).EI-MS(m/z)249.5[M]+.IR(KBr)3550(OH)；3080,
2880,1510,1430,910,870,670cm-1.Anal.Calcd forC13H17N2O3:C,62.67；H,6.88；N,
11.24.Found:C,62.68；H,6.86；N,11.25.ESR:AN=7.58G, g=2.0071.
Embodiment 2：The synthesis of compound 2
300mg (2.0mmol) 2,3- dimethyl -2,3- dihydroxy amido butane is dissolved in into 40ml to refine in methanol, room temperature is stirred
Mix, add 152mg (1.0mmol) to hydroxyl m-methoxybenzaldehyde, back flow reaction 24h has white precipitate precipitation in solution, subtracted
Pressure removes methanol, and residue is suspended in 20mlCH2Cl2In, ice-water bath cooling, by 600mg (2.8mmol) NaIO4It is dissolved in 5ml water
In, it is stirred vigorously down and is slowly added into reaction system, drop continues to react 0.5h after finishing, and stops reaction, organic phase is washed with water one
It is secondary, take organic phase to be dried with anhydrous magnesium sulfate, solvent is evaporated off and obtains blue grease.Column chromatography for separation obtains blue powder 156mg.
Rf=0.60 (CHCl3/CH3OH,20:1).EI-MS(m/z)278.3[M]+.IR(KBr)3475,2363,1660,
1148,880,760cm-1.Anal.Calcd forC14H19N2O4:C,60.20；H,6.86；N,10.03.Found:C,60.23；
H,6.88,N 10.06.ESR:AN=8.25G, g=2.0068.
Embodiment 3：The synthesis of compound 4
300mg (2.0mmol) 2,3- dimethyl -2,3- dihydroxy amido butane is dissolved in into 40ml to refine in methanol, room temperature is stirred
Mix, adding in 166mg (1.0mmol) p -carboxybenzaldehyde, back flow reaction 24h, solution has white precipitate precipitation, and first is removed under reduced pressure
Alcohol, residue is suspended in 20mlCH2Cl2In, ice-water bath cooling, by 600mg (2.8mmol) NaIO4It is dissolved in 5ml water, acutely stirs
Mix down and be slowly added into reaction system, drop continues to react 0.5h after finishing, and stops reaction, organic phase is washed with water once, taken organic
Dried with anhydrous magnesium sulfate, solvent is evaporated off and obtains blue grease.Column chromatography for separation obtains blue powder 114mg.
Rf=0.62 (CHCl3/CH3OH,20:1).EI-MS(m/z)278[M]+.IR(KBr)3300,2960,1650,
1390,1130,690cm-1.Anal.Calcd forC14H17N2O4:C,60.64；H,6.18；N,10.10.Found:C,60.67；
H,6.19；N,10.12.ESR:AN=8.22G, g=2.0096.
Exemplified by above-described embodiment 1, the compound 1 that it is synthesized is as follows to the degradation experiment of methyl orange：
1. experimental program：
(1) using electronic balance weighing 8mg methyl orange, methyl orange solution is configured with 1000mL volumetric flasks, is placed
It is standby at dark；
(2) 100mL beaker is taken, weighing 50mL methyl orange solutions with graduated cylinder pours into beaker, according to experimental factors
Difference weighs inequality catalyst and poured into beaker, it is stirred under dark room conditions；
(3) appropriate solution is taken with glue head dropper, takes syringe extrusion to filter out the catalyst in taken solution, to filter
Liquid carries out absorbance detection using 721 type visible spectrophotometers；
Take a sample to carry out absorbance with visible spectrophotometer per 10min to be detected, until methyl orange degradation is complete.
2. experimental result：
To embodiment 1 and the ultraviolet data mapping of the gained of embodiment 3, it can be seen that from Fig. 1 and Fig. 2, with mixing time
Extension, the content of methyl orange gradually reduces, and degradation effect is obvious.
The foregoing is only a preferred embodiment of the present invention, is not intended to limit the scope of the present invention.
Claims (6)
1. a kind of methyl orange degradation agent, its structure is as shown in logical formula (I)：
R in logical formula (I)1~R5Respectively NO2、OH、H、OCH3、OCH2CH3、CF3, one kind in COOH or halogen.
2. methyl orange degradation agent according to claim 1, it is characterised in that：R in the logical formula (I)1~R5In any three
Substituent is H.
3. methyl orange degradation agent according to claim 1, it is characterised in that：R in the logical formula (I)1~R5Middle any four
Substituent is H.
4. according to methyl orange degradation agent any one of in claims 1 to 3, it is characterised in that：The halogen is F, Cl
Or Br.
5. a kind of preparation method of methyl orange degradation agent according to claim 1, it is characterised in that：By 2.0mmol2,3-
Dimethyl -2,3- dihydroxy amido butane is dissolved in 40ml and refined in methanol, is stirred at room temperature, and adds 1.0mmol with R1~R5Substituted benzene
In formaldehyde, back flow reaction 24h has white precipitate precipitation in solution, methanol is removed under reduced pressure, residue is suspended in 20mlCH2Cl2In,
Ice-water bath is cooled down, by 2.8mmolNaIO4It is dissolved in 5ml water, is stirred vigorously down and is slowly added into reaction system, drips Bi Houji
Continuous reaction 0.5h, stops reaction, organic phase is washed with water once, takes organic phase to be dried with anhydrous magnesium sulfate, solvent is evaporated off and obtains blue
Grease, column chromatography for separation obtains blue powder.
6. methyl orange degradation agent described in claim 1 is in the application of Wastewater Dyes methyl orange degradation.
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| CN201710478704.3A CN107235908A (en) | 2017-06-22 | 2017-06-22 | A kind of methyl orange degradation agent and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111943935A (en) * | 2020-08-21 | 2020-11-17 | 西安工业大学 | Prolinol rapid desulfurizing agent and preparation method thereof |
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| JP2011124567A (en) * | 2009-11-16 | 2011-06-23 | Panasonic Electric Works Co Ltd | Organic solar cell |
| CN102341951A (en) * | 2009-03-06 | 2012-02-01 | 日本电气株式会社 | Photoelectric conversion element, process for producing same, optical sensor, and solar cell |
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2017
- 2017-06-22 CN CN201710478704.3A patent/CN107235908A/en active Pending
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| US20050256169A1 (en) * | 2004-05-12 | 2005-11-17 | Sujatha Karoor | Nitric oxide scavengers |
| CN1743316A (en) * | 2004-09-03 | 2006-03-08 | 首都医科大学 | 2-substituted phenyl-4,4,5,5-tetramethyl-1,3,-dioxy imidazolines, their preparation and pharmaceutical use |
| CN102341951A (en) * | 2009-03-06 | 2012-02-01 | 日本电气株式会社 | Photoelectric conversion element, process for producing same, optical sensor, and solar cell |
| JP2011124567A (en) * | 2009-11-16 | 2011-06-23 | Panasonic Electric Works Co Ltd | Organic solar cell |
| CN102070532A (en) * | 2011-01-25 | 2011-05-25 | 中国人民解放军第四军医大学 | Anti-tumor medicament structure |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111943935A (en) * | 2020-08-21 | 2020-11-17 | 西安工业大学 | Prolinol rapid desulfurizing agent and preparation method thereof |
| CN111943935B (en) * | 2020-08-21 | 2023-02-10 | 西安工业大学 | Prolinol rapid desulfurizing agent and preparation method thereof |
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