CN1332891C - Hydrogen peroxide catalytic decomposing method of phenol compound - Google Patents
Hydrogen peroxide catalytic decomposing method of phenol compound Download PDFInfo
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- CN1332891C CN1332891C CNB2004100693711A CN200410069371A CN1332891C CN 1332891 C CN1332891 C CN 1332891C CN B2004100693711 A CNB2004100693711 A CN B2004100693711A CN 200410069371 A CN200410069371 A CN 200410069371A CN 1332891 C CN1332891 C CN 1332891C
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- hydrogen peroxide
- acetonitrile
- phenolic compound
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- vanadate
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Abstract
The present invention discloses a hydrogen peroxide catalytic decomposition method of a phenolic compound, which belongs to the technical field of environmental treatment. Vanadate or heteropoly vanadate is used as a catalyst, hydrogen dioxide is used as an oxidizing agent, and the vanadate or the heteropoly vanadate and the hydrogen dioxide are added in a water-acetonitrile (4: 1 v/v) solution together with the phenolic compound and are catalyzed and decomposed under heating and stirring conditions, so the decomposition conversion rate of the phenolic compound reaches more than 97 %. The phenolic compound which is difficult to degrade is quickly catalyzed and decomposed into CO2, corresponding inorganic anions and nitromethane or acetic acid with high efficiency in a neutral water-acetonitrile solution with the present invention.
Description
Technical field
The invention belongs to the environmental improvement technical field, particularly a kind of hydrogen peroxide catalytic decomposing method of phenolic compound.
Background technology
The fast development of chemical industry and the environmental problem that causes has become one of focus of paying close attention to the world today.Phenolic compound in the trade effluent is principal pollutant, for example as sterilant, sterilizing agent, wood preservative and the chlorophenol that is widely used; As sterilant, dyestuff, explosive, widely used nitrophenol etc. in the commercial runs such as preparation of textiles and paper.Even the phenolic compound in these trade effluents that are discharged still has great pollution to environment under very low concentration, and these compounds are difficult to handle with biodegradable method owing to their stability.The chemical process of using mainly contains at present: chemical oxidization method and photocatalysis Decomposition method.Miguel L.Rodriguez, Vitaliy I.Timokhin waits report in document " Advances inEnvironmental Research 7 (2003) 583-595 ", and chemical oxidization method can not make phenol decompose fully.And C.-H.Yoon, S.-H.Cho, S.-H.Kim and S.-R.Ha, Deng report in document " WaterScience and Technology Vol43, No.2, pp.229-236 ", pressurized aqueous combustion must carry out under High Temperature High Pressure, the easy inactivation of catalyzer, processing costs height.P.V.Kamat, report in " Chem.Rev.3 (1993) 267 ", the photocatalysis Decomposition method mainly is under the UV, visible light rayed, in the presence of hydrogen peroxide or ozone or titanium dioxide, makes phenolic compound resolve into biodegradable organic molecule, CO
2Accordingly by the inorganic anion of mineralising.At document " A.Mylonas; E.Papaconstantinou; J.Photochemistry and Photobiology A:Chemistry 94 (1996) 77-82 ", " A.Hiskia; E.Androulaki et al.Res.Chem.Intermed.Vol.26; No.3; pp.235-251 (2000) " and " P.Kormali; D.Dimoticali; E.Papaconstantinou, et al.AppliedCatalysis B:Enviromental 48 (2004) 175-183) " report in; Keggin type phospho-wolframic acid is found to be a kind of and the same effectively photocatalyst of titanium dioxide, can make chlorophenol be decomposed into carbonic acid gas and hydrochloric acid.Yet (pH～2) are carried out in this light-catalyzed reaction under acidic conditions, are not reported for the catalyzed degradation of the nitrophenol of more difficult decomposition.
Summary of the invention
The hydrogen peroxide catalytic decomposing method that the purpose of this invention is to provide a kind of phenolic compound, it is characterized in that with vanadate or hetero-vanadate be catalyzer, aqueous hydrogen peroxide solution is an oxygenant, in water-acetonitrile mixing solutions, heating, stirring, carry out the cartalytic decomposition effect of phenolic compound, this system catalytic degradation reaction may further comprise the steps:
1) with the vanadate of (20-70) μ mol or (2-6) μ mol hetero-vanadate catalyzer be dissolved in (1-8) ml, in 30% (v/v) hydrogen peroxide, be made into the 10ml homogeneous aqueous solution by water-acetonitrile (4: 1 v/v) and acetonitrile;
2) phenolic compound is dissolved in (4: 1v/v), heat 30-70 ℃, under agitation reacted 10-120 minute, phenolic compound is decomposed into CO in the water-acetonitrile solution that contains catalyzer and hydrogen peroxide in the step (1)
2, H
2O and corresponding inorganic anion and Nitromethane 99Min. or acetate.
Described vanadate is KVO
3,, NaVO
3, or NH
4VO
3
Described hetero-vanadate is K
7NiV
13O
38And K
7MnV
13O
38
The invention has the beneficial effects as follows: the present invention compared with the prior art, the phenolic compound that makes difficult degradations such as nitrophenol rapidly and efficiently is decomposed into CO under neutrallty condition
2With corresponding inorganic anion and Nitromethane 99Min. or acetate.The rates of decomposing and transforming of all kinds of phenol is reached more than 97%.
Embodiment
The present invention is the hydrogen peroxide catalyzed degradation method of new a kind of phenolic compound.Being to be catalyzer with vanadate or hetero-vanadate, is oxygenant with the hydrogen peroxide, water-acetonitrile (4: 1v/v) carry out the cartalytic decomposition effect of phenols aromatic hydroxy compound under the mixed solvent condition of heating and stirring, this system cartalytic decomposition effect may further comprise the steps:
1) vanadate or the 3 μ mol hetero-vanadate catalyzer with preferred 40 μ mol are dissolved in (1-8) ml, in 30% (v/v) hydrogen peroxide, by water-acetonitrile (4: 1v/v) be made into the 10ml homogeneous aqueous solution with acetonitrile;
2) phenolic compound is dissolved in the water-acetonitrile solution that contains catalyzer and hydrogen peroxide in (1), heats 30-70 ℃, under agitation reacted 10-120 minute, phenolic compound is degraded to CO
2, H
2O and corresponding inorganic salt and a spot of phenols organic degradation small molecules (as Nitromethane 99Min. or acetate).
Above-mentioned vanadate is KVO
3,, NaVO
3, or NH
4VO
3Hetero-vanadate is K
7NiV
13O
38Or K
7MnV
13O
38
For embodiment the present invention is further specified again below.
Embodiment 1:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in the 8ml30% hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 15 minutes, and reaction result is: p-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of p-NP reaches 99.2%.
Embodiment 2:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 50 ℃ is carried out catalytic degradation reaction.Reaction times is 40 minutes, and reaction result is: p-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of p-NP reaches 98.7%.
Embodiment 3:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 30 ℃ is carried out catalytic degradation reaction.Reaction times is 10 hours, and reaction result is: p-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of p-NP reaches 99.5%.
Embodiment 4:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 1ml30% (v/v) hydrogen peroxide, is made into uniform solution with 2ml acetonitrile and 7ml water.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 60 minutes, and reaction result is: p-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of p-NP reaches 53%.
Embodiment 5:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 2ml30% (v/v) hydrogen peroxide, is made into uniform solution with 2ml acetonitrile and 6ml water.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 60 minutes, and reaction result is: p-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of p-NP reaches 66.5%.
Embodiment 6:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 3ml30% (v/v) hydrogen peroxide, is made into uniform solution with 2ml acetonitrile and 5ml water.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 30 minutes, and reaction result is: p-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of p-NP reaches 88%.
Embodiment 7:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 4ml30% (v/v) hydrogen peroxide, is made into uniform solution with 2ml acetonitrile and 4ml water.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 30 minutes, and reaction result is: p-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of p-NP reaches 91%.
Embodiment 8:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 6ml30% (v/v) hydrogen peroxide, is made into uniform solution with 2ml acetonitrile and 2ml water.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 30 minutes, and reaction result is: p-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of p-NP reaches 94%.
Embodiment 9:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) o-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 15 minutes, and reaction result is: o-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of o-NP reaches 97.5%.
Embodiment 10:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) m-nitrophenol is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 15 minutes, and reaction result is: m-nitrophenol is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of m-nitrophenol reaches 99%.
Embodiment 11:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.38g (4mmol) Pyrogentisinic Acid is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 60 minutes, and reaction result is: phenol is decomposed into CO
2With water and a spot of acetone, the rates of decomposing and transforming of phenol reaches 97.5%.
Embodiment 12:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.51g (4mmol) P-Chlorophenol is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 15 minutes, and reaction result is: P-Chlorophenol is decomposed into CO
2And Cl
-, the rates of decomposing and transforming of P-Chlorophenol reaches 98.5%.
Embodiment 13:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.51g (4mmol) orthomonochlorphenol is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 15 minutes, and reaction result is: orthomonochlorphenol is decomposed into CO
2And Cl
-, the rates of decomposing and transforming of orthomonochlorphenol reaches 98%.
Embodiment 14:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.51g (4mmol) m-Chlorophenol is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 15 minutes, and reaction result is: m-Chlorophenol is decomposed into CO
2And Cl
-, the rates of decomposing and transforming of m-Chlorophenol reaches 99%.
Embodiment 15:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.43g (4mmol) p-methyl phenol is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 120 minutes, and reaction result is: p-methyl phenol is decomposed into CO
2And water, the rates of decomposing and transforming of p-methyl phenol reaches 99.1%.
Embodiment 16:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.5g (4mmol) MEHQ is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 60 minutes, and reaction result is: MEHQ is decomposed into CO
2And water, the rates of decomposing and transforming of MEHQ reaches 99.2%.
Embodiment 17:
Take by weighing 5.3mg (3 μ mol) KVO
3Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 15 minutes, and reaction result is: p-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And acetate, the rates of decomposing and transforming of p-NP reaches 99.5%.
Embodiment 18:
Take by weighing 5.7mg (3 μ mol) K
7MnV
13O
38Catalyzer is dissolved in 8ml30% (v/v) hydrogen peroxide and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is carried out catalytic degradation reaction.Reaction times is 15 minutes, and reaction result is: p-NP is decomposed into CO
2, NO
3 -With minor N O
2 -And Nitromethane 99Min., the rates of decomposing and transforming of p-NP reaches 99%.
Comparative Examples 1:
Under the catalyst-free condition, 0.57g (4mmol) p-nitrophenyl is dissolved in 8ml30% (v/v) hydrogen peroxide is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, stir, reflux to 70 ℃ is reacted.Reaction times is 120 minutes, and reaction result is: the p-NP rates of decomposing and transforming has only 15%.
Comparative Examples 2:
Take by weighing 5.7mg (3 μ mol) K
7NiV
13O
38Catalyzer is dissolved in the 8ml water and is made into uniform solution with the 2ml acetonitrile.In 50ml two neck round-bottomed flasks, 0.57g (4mmol) p-NP is dissolved in the above-mentioned uniform solution, stir, reflux to 70 ℃ is reacted.Reaction times is 120 minutes, and reaction result is: p-NP decomposes hardly.
By the contrast of top embodiment, can draw the present invention and make phenolic compound under neutrallty condition, efficiently catalytic decomposition is CO fast
2With corresponding inorganic anion and a spot of phenols organic degradation small molecules.
Claims (2)
1. the hydrogen peroxide catalytic decomposing method of a phenolic compound, it is characterized in that: this method is catalyzer with the hetero-vanadate, with the hydrogen peroxide is oxygenant, in the water-acetonitrile solution of 4: 1 (v/v), carry out the phenolic compound cartalytic decomposition effect under condition of heating and stirring, this cartalytic decomposition effect may further comprise the steps:
1) 2-6 μ mol hetero-vanadate catalyzer is dissolved in 1-8ml, in 30% (v/v) hydrogen peroxide, by water-acetonitrile (4: 1v/v) be made into the 10ml homogeneous aqueous solution with acetonitrile;
2) phenolic compound is dissolved in 4: 1 (v/v) water-acetonitrile solutions that contain catalyzer and hydrogen peroxide in the step (1), heats 30-70 ℃, under agitation reacted 10-120 minute, phenolic compound is decomposed into CO
2, H
2O and corresponding inorganic anion and Nitromethane 99Min. or acetate.
2. according to the hydrogen peroxide catalytic decomposing method of the described phenolic compound of claim 1, it is characterized in that: described hetero-vanadate is K
7NiV
13O
38And K
7MnV
13O
38
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| CNB2004100693711A CN1332891C (en) | 2004-07-21 | 2004-07-21 | Hydrogen peroxide catalytic decomposing method of phenol compound |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100693711A CN1332891C (en) | 2004-07-21 | 2004-07-21 | Hydrogen peroxide catalytic decomposing method of phenol compound |
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| CN1332891C true CN1332891C (en) | 2007-08-22 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1056893A (en) * | 1991-07-04 | 1991-12-11 | 东北煤气化设计研究所 | Gas sewage extracting and dephenolizing, ammonia still process treatment process |
| CN1133600A (en) * | 1993-07-29 | 1996-10-16 | 普罗格特-甘布尔公司 | Oxidation process |
| CN1150128A (en) * | 1995-11-15 | 1997-05-21 | 陶荣达 | Paper-mill waste water treatment technique |
-
2004
- 2004-07-21 CN CNB2004100693711A patent/CN1332891C/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1056893A (en) * | 1991-07-04 | 1991-12-11 | 东北煤气化设计研究所 | Gas sewage extracting and dephenolizing, ammonia still process treatment process |
| CN1133600A (en) * | 1993-07-29 | 1996-10-16 | 普罗格特-甘布尔公司 | Oxidation process |
| CN1150128A (en) * | 1995-11-15 | 1997-05-21 | 陶荣达 | Paper-mill waste water treatment technique |
Non-Patent Citations (1)
| Title |
|---|
| 光催化氧化处理污水的研究 河北化工，第1期 2002 * |
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