CN109939743A - Amination nano ferriferrous oxide supported metal phthalocyanine photocatalyst, preparation method and application - Google Patents
Amination nano ferriferrous oxide supported metal phthalocyanine photocatalyst, preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of amination nano ferriferrous oxide supported metal phthalocyanine photocatalysts, preparation method and application.It is by amination nano ferriferrous oxide direct impregnation in the metal phthalocyanine aqueous solution of 5~100mg/L, vibrate 3 at room temperature~for 24 hours, and it will be metal phthalocyanine loaded on amino ferroso-ferric oxide surface by electrostatic interaction, it is obtained through Magneto separate, washing, drying.The mass percentage of the metal phthalocyanine in the catalyst is 0.1~5.0%.Composite photo-catalyst produced by the present invention has the double effects of photocatalytic degradation and Magneto separate recycling, and catalyst can use visible-light activated oxygen in water, realize the oxidative degradation of organic pollutants in water body.Amination ferroso-ferric oxide supported metal phthalocyanine catalyst method prepared by the present invention is simple, low in cost, environmental-friendly, it has, and particle is small, easy dispersion, and reaction condition is mild, photocatalytic activity is high, easy Magneto separate, the advantages of can be recycled.
Description
Technical field
The present invention relates to a kind of amination nano ferriferrous oxide supported metal phthalocyanine photocatalyst, preparation method and answer
With, more specifically use amination nano ferriferrous oxide supported metal phthalocyanine photocatalyst and its preparation, be suitable for phenols
With the degradation of dyestuff contaminant.
Background technique
Metal phthalocyanine has very strong absorption in visible light region, as photosensitizer or photochemical catalyst environmental contaminants drop
Be widely used (material Leader A: a summary piece, 29 (2015), 57) in solution.But general phthalocyanine compound is in aqueous solution
Dissolubility is poor, causes its catalytic activity poor；And although the water soluble metal phthalocyanine catalytic activity containing functional group is higher,
Aggregation is easy there are Phthalocyanine in homogeneous catalytic reaction system and reduces catalytic activity, is difficult to separate and recover and is reused.
To overcome the above disadvantages, Phthalocyanine is loaded into ion exchange resin, layer using traditional infusion process or chemical modification method
On shape clay, Mg/Al hydrotalcite, molecular sieve or silicon-based mesoporous material (Langmuir, 20 (2004),
6302.J.Mol.Catal.A:Chem.,269(2007),183.Appl.Catal.B:Environ.,87(2009),
146.Environ.Sci.Technol.,39(2005)651.Chem.Mater.,19(2007),
1452.J.Hazard.Mater.193 (2011) 209.), the photocatalytic activity of metal phthalocyanine can be not only kept, but also be able to achieve and urge
The recycling and reuse of agent.But above-mentioned carrier loaded catalyst is needed in use by being centrifuged or filtering
Means separate catalyst from water phase, and separation process is relatively cumbersome.
In conjunction with the order mesoporous organic polymer of functional amido, FDU- is made in water-soluble sulfonic acids metal phthalocyanine by Xing Rong etc.
(application number: 201210589284.3) Chinese invention patent application, improves silicon-based mesoporous material and is not suitable for alkaline item PdPcS
The disadvantages such as part, other carrier specific surface areas be low, realize effectively removing for organic pollutant, but the material recovery still needs
By the means of centrifugation or filtering, it is unfavorable for large-scale Industrial Wastewater Treatment.
Summary of the invention
The present invention is directed to the above-mentioned deficiency of the prior art, provides one kind and does not need through centrifugation or filters separation,
Method is simple, low in cost, environmental-friendly, the amination nano ferriferrous oxide supported metal phthalocyanine photocatalysis that is easily recycled
Agent.
In order to solve the above-mentioned technical problem, a kind of the technical solution adopted by the present invention are as follows: amination nano ferriferrous oxide
The raw material for preparing of supported metal phthalocyanine catalyst, the catalyst includes amination nano ferriferrous oxide and metal phthalocyanine, described
The sulfonic group of metal phthalocyanine or the amino of carboxyl and nano ferriferrous oxide pass through electrostatic interaction and load.
The present invention also provides a kind of preparation method of above-mentioned amination nano ferriferrous oxide supported metal phthalocyanine catalyst,
Preparation step includes:
(1) it weighs trivalent iron salt and acetate is dissolved in ethylene glycol, dissolution is stirred at room temperature, organic amine is then added, stirs
Mix the orange solution stable to formation；Reaction solution is transferred in reaction kettle, 150~220 DEG C of reactions 2~for 24 hours；It is passed through after cooling
Magneto separate is respectively washed for several times with deionized water and ethyl alcohol until neutral；Sample after washing is placed in a vacuum drying oven drying,
Up to amination nano ferriferrous oxide；
(2) amination nano ferriferrous oxide made from step (1) is added in metal phthalocyanine aqueous solution, at room temperature
Oscillation dipping 3~be washed with deionized for 24 hours, after Magneto separate colourless to solution, is placed in vacuum drying for the sample after Magneto separate
It is dry in case, obtain amino functional nano ferriferrous oxide supported metal phthalocyanine catalyst.
Organic amine described in step (1) is one of ethylenediamine, Diethylenetriamine, three second tetramines or tetren.
The mass concentration of ferric iron and acetate in ethylene glycol is respectively 20-200g/L and 20 described in step (1)
~300g/L；5~30min is stirred at room temperature；Then organic amine is added, makes volume fraction of the organic amine in mixed solution
5~50%；Reaction solution in a kettle 150~220 DEG C reaction 2~for 24 hours.
Amination nano ferriferrous oxide described in step (1) is prepared by one step of solvent-thermal method, and size is 20
Between~200nm.
Metal phthalocyanine described in step (2) be aluminum phthalocyanine, sulfonation phthalocyanine phthalocyanine zinc, sulfonated phthalocyanine iron, sulfonated phthalocyanine palladium,
One of carboxyl aluminum phthalocyanine, carboxyl zinc phthalocyanine, carboxyl FePC；They have relatively strong inhale at visible region (500-700nm)
It receives；The pH of metal phthalocyanine aqueous solution after being added to amination nano ferriferrous oxide adjusts the metal after load between 2~7
Shared mass percent is 0.1~5.0% to phthalocyanine in the catalyst.
The concentration of metal phthalocyanine aqueous solution described in step (2) is 5~100mg/L.
The present invention also provides a kind of amination nano ferriferrous oxide supported metal phthalocyanine catalyst of above-mentioned preparation, are applicable in
In the absorption and degradation of organic pollutants, application in Visible Light Induced Photocatalytic organic wastewater, specific method are as follows:
The catalyst that quality is 3~50mg is put into the organic wastewater that concentration is 0.01~10mM of 50mL, pH value is
2~12, drum air, 30~300min can remove the organic pollutant in waste water under visible light source irradiation.
It is carried out under visible light (sunlight) using the reaction of the catalyst degradation organic pollutant.
The organic wastewater can be nitrophenol, bisphenol-A, the chlorophenol (compound that general formula C6H6-xClxO is indicated
One or more of, wherein x=0~5), dyestuff.The visible light source is tungsten halogen lamp, sunlight or xenon lamp artificial light sources.
Magneto separate of the invention exactly will be adsorbed on the substance on magnet with magnet and attract around magnet, play
Isolated effect.
The no particular/special requirement of vacuum drying of the invention, a conventional oven can also be with, usually 60 DEG C dry 12~for 24 hours can be real
Existing drying effect.
Metal phthalocyanine described in step (2) be aluminum phthalocyanine, sulfonation phthalocyanine phthalocyanine zinc, sulfonated phthalocyanine iron, sulfonated phthalocyanine palladium,
One of carboxyl aluminum phthalocyanine, carboxyl zinc phthalocyanine, carboxyl FePC, are specifically referred to literature method (Chinese
J.Chem., 21 (2003), 1092.Prog.Org.Coating, 31 (1997), 139.) it is prepared or commercial product.This
The advantages of invention and the utility model has the advantages that
1. the present invention provides a kind of preparation method of amination nano ferriferrous oxide supported metal phthalocyanine catalyst and
Using.Supported metal phthalocyanine catalyst obtained through the invention has fast degradation target contaminant and is easy to Magneto separate and returns
The advantage recycled is received, can be used for the photocatalytic degradation of phenols and dyestuff contaminant in industrial wastewater and drinking water.Compared to biography
Unite carrier loaded catalysis material, load capacity provided by the invention be 1% catalyst can in radiation of visible light 90min by 2,
The degradation of 4,6- trichlorophenol, 2,4,6,-Ts is complete, it is shown that superior photocatalytic activity and stability, catalyst have been reused 10 times, catalysis
Effect does not significantly decrease.
2. amination nano ferriferrous oxide supported metal phthalocyanine method for preparing catalyst prepared by the present invention is simple, at
This is cheap, environmental-friendly, performance is stable, is easily recycled, the application prospect with industrialization.
3. eight carboxyl zinc phthalocyanines are bonded in nanometer four different from existing use chemical bonding and aoxidized by method of the invention
The step of three ironing surface methods, this existing carrying method needs a series of complex, is first carried using silylating reagent processing
The silicone hydroxyl in body surface face, then it is bonded amino group, it is then chemically bonded to obtain supported catalyst with phthalocyanine, process is cumbersome.
And the present invention is to pass through water-soluble metal phthalocyanine and amination nano ferriferrous oxide between sulfonic group (or carboxyl) and amino
Electrostatic interaction, by metal phthalocyanine loaded arrive nano ferriferrous oxide surface, the recycling of photocatalytic degradation-Magneto separate may be implemented
Dual purpose.
4. method of the invention is directed to existing support type phthalocyanine catalyst, carrier does not have magnetic disadvantage；It is logical
Catalyst prepared by the present invention is crossed, oxygen in water can be activated under visible light illumination, realizes organic pollutants catalysis drop
Solution may be implemented catalyst by Magneto separate means and recycle.
5. method of the invention is different from the synthetic method of existing chitosan magnetic phthalocyanine, they use and are coated with chitosan
The carrier that is loaded as four carboxyl phthalocyanine cobalt of ferroso-ferric oxide, be mixed 60~80 hours using organic solvent DMF dissolution,
Then revolving is made, and preparation step is more, the time is long, be related to organic solvent, process is cumbersome；The present invention is with the oxidation of amination nanometer four
Three-iron is metal phthalocyanine loaded carrier, and NH can be presented in acid condition using its amino3 +, with sulfonated phthalocyanine (SO3 -) or
Carboxyl phthalocyanine (COO-) between the principle that is combined by electrostatic interaction, preparation method is simple to operation.
Use the ferroso-ferric oxide for being coated with amorphous c film layer for carrier 6. the prior art has.The phthalocyanine of load is four
Nitro copper phthalocyanine, type, carrying method and purposes are different from the present invention；They prepare Fe using solvent-thermal method3O4@C@
TNCuPc, catalyst obtained is used for the detection of chlorophenol pollutant, and the present invention prepares amination using solvent heat one-step method
Nano ferriferrous oxide is made magnetic using infusion process on this basis and carries phthalocyanine photochemical catalyst, pollutes for phenols and dye class
Object degradation.
Detailed description of the invention
Fig. 1 is catalyst preparation flow diagram of the invention.
Fig. 2 is according to embodiment 1, the Fourier of amination nano ferriferrous oxide supported metal phthalocyanine catalyst obtained
Transform infrared spectroscopy figure, wherein (a) NH2@nFe3O4, (b) AlPcS-NH2@nFe3O4。
Fig. 3 be according to embodiment 1, amination nano ferriferrous oxide supported metal phthalocyanine catalyst obtained it is ultraviolet-
It can be seen that diffusing reflection spectrum, wherein (a) NH2@nFe3O4(b) AlPcS-NH2@nFe3O4Diffusing reflection spectrum, (c) AlPcS is water-soluble
The visible absorption spectra of liquid.
Fig. 4 is according to embodiment 1, the transmission electricity of amination nano ferriferrous oxide supported metal phthalocyanine catalyst obtained
Mirror (TEM) photo.
Fig. 5 is according to embodiment 1, the X-ray of amination nano ferriferrous oxide supported metal phthalocyanine catalyst obtained
Diffraction pattern (XRD).
Fig. 6 is according to embodiment 1, and the magnetization of amination nano ferriferrous oxide supported metal phthalocyanine catalyst obtained is bent
Line (VSM), illustration are comparison diagram before and after Magneto separate.
Fig. 7 is degradation effect figure of the different components to TCP in the embodiment of the present invention 1.
Fig. 8 is the AlPcS@NH of different phthalocyanine load capacity in the embodiment of the present invention 42-Fe3O4To the shadow of TCP degradation efficiency
It rings.
Fig. 9 is influence of the different initial ph value to the degradation efficiency of TCP in the embodiment of the present invention 6.
Figure 10 is different type organic phenol degradation effect figure in the embodiment of the present invention 7.
Figure 11 is in the embodiment of the present invention 8, and catalyst continuously recycles the effect of 10 photocatalytic degradation 0.25mmol/L TCP
Fruit figure.
Specific embodiment
With reference to the accompanying drawing and specific implementation case further illustrates the contents of the present invention, makes the purpose of the present invention and effect
Fruit is more obvious, but the present invention is not limited solely to following embodiment.Preparation technology flow chart of the present invention is as shown in Figure 1, specific
Step is referring to each embodiment.
Embodiment 1
A 4.0g FeCl) is weighed3·6H2O, 12.00g anhydrous sodium acetate, the two is dissolved in the ethylene glycol of 120mL,
20min is stirred at room temperature, the ethylenediamine of 20mL is then added, stirring is to forming stable orange solution.Reaction solution is transferred to
In reaction kettle, 180 DEG C of reaction 8h.Through Magneto separate after cooling, respectively washed for several times with deionized water and ethyl alcohol until neutral.After washing
Sample in 60 DEG C of vacuum ovens dry 12h to get amination nano ferriferrous oxide (NH2-Fe3O4)。
B NH made from step A) is weighed2-Fe3O40.200g is added to the sulfonated phthalocyanine aluminum water solution that concentration is 80mg/L
In, pH to 3.0 is adjusted, 12h is vibrated at room temperature, is washed with deionized after Magneto separate to neutrality, by the sample after Magneto separate
It is placed in 60 DEG C of vacuum ovens dry 12h, obtains amino functional nano ferriferrous oxide load sulfonated phthalocyanine catalyst
(AlPcS@NH2-Fe3O4)。
Specific IR Characterization, ultraviolet-visible diffuse reflectance spectrum, transmission electron microscope (TEM) photo and x-ray diffraction pattern (XRD)
Attached drawing 2-6 is seen with magnetization curve (VSM).
It can be seen that the saturation flux numerical quantity of catalyst is big from magnetism testing attached drawing, illustrate that material can pass through magnetic
Field separation and recovery.The comparison photo before and after the visible Magneto separate of illustration in attached drawing 6, it can be seen that be able to achieve Magneto separate.
Photocatalytic degradation experiment condition: light-catalyzed reaction carries out under the irradiation of 500W tungsten lamp, and reaction solution is contained in 50mL band
In the transparent glass reactor for condensing water leg, apart from light source distance 10cm, catalyst is set to be suspended in solution by drum air method
In.Catalyst amount is 20mg in reaction system, and TCP concentration is 0.25mM, with Na2CO3-NaHCO3Buffer solution controls pH
9.9.Every 15 minutes Magneto separate sampling and testings, TCP concentration changes with time curve was obtained through efficient liquid phase chromatographic analysis.
Experimental result is shown in Fig. 7 for photocatalytic degradation, and as shown in Figure 7b, illumination 90min, TCP removal rate is up to 95%.And same batten
Under part, amination ferroso-ferric oxide can not degrade TCP (Fig. 7 a), and shown catalytic action is aluminum phthalocyanine, four oxygen of amino
Change three-iron and only plays carrier and Magneto separate.In addition, the aluminum phthalocyanine of comparable sodium, amination Fe3O4The sulfonation of load
The photocatalysis efficiency of aluminum phthalocyanine is close to (Fig. 7 b and 7c) in phthalocyanine catalyst and homogeneous phase solution, it is meant that load does not reduce
The catalytic effect of catalyst.
Embodiment 2
In implementation process except for the following differences, remaining operation is the same as embodiment 1.In step A the dosage of ethylenediamine become 5~
60mL.The AlPcS@NH of different amino contents is made2-Fe3O, and investigate their photocatalytic activity.
Embodiment 3
In implementation process except for the following differences, remaining operation is the same as embodiment 1.Ethylenediamine replaces with diethyl three in step A
One of amine, three second tetramines or tetren.The AlPcS@NH of different amine types is made2-Fe3O4, and investigate their light
Catalytic activity.
Embodiment 4
In implementation process except for the following differences, remaining is the same as embodiment 1.The concentration of aluminum phthalocyanine becomes 10 in step A
~100mg/L.The AlPcS@NH of different phthalocyanine load capacity is made2-Fe3O4, TCP removal effect is shown in after photocatalytic degradation 90min
Fig. 8.With the increase of aluminum phthalocyanine load capacity, the efficiency of photocatalytic degradation TCP first increases (sample 1 → 5), then declines
(sample 6).
Embodiment 5
In implementation process except for the following differences, remaining is the same as embodiment 4.Aluminum phthalocyanine replaces with sulfonation phthalein in step A
Cyanines aluminium or sulfonated phthalocyanine palladium.The MPcS@NH of different central metals, different loads amount is made2-Fe3O4Catalyst, and investigate them
Photocatalytic activity.
Embodiment 6
In implementation process except for the following differences, remaining is the same as embodiment 1.The pH of solution is adjusted to 2~12 models in step B
It encloses.TCP removal effect is shown in Fig. 9 after photocatalysis 90min under condition of different pH.As pH is increased, photocatalysis removal rate is accelerated, alkalinity
Condition is conducive to TCP degradation.
Embodiment 7
In implementation process except for the following differences, remaining is the same as embodiment 1.2,4,6- trichlorophenol, 2,4,6,-T (TCP) converts in step B
For other phenolic comp ' ds pollutions (such as 4- chlorophenol, 2,4 dichloro phenol, bisphenol-A).Different organic phenols are degraded under visible light
Removal rate after 90min is shown in Figure 10.
Embodiment 8
On the basis of embodiment 1, catalyst stability is investigated by circulation experiment.After each round degradation,
TCP and deionized water are added in reaction solution, so that liquor capacity is kept 50mL, TCP concentration is 0.25mmol/L, in circulation experiment
Appropriate NaOH solution adjustment pH is added and returns to 9.9.Figure 11 shows that catalyst has stable photocatalytic activity, has been recycled 10
It is secondary, still it is able to maintain higher photocatalytic activity.
Claims (10)
1. a kind of amination nano ferriferrous oxide supported metal phthalocyanine catalyst, it is characterised in that: the preparation of the catalyst is former
Material includes amination nano ferriferrous oxide and metal phthalocyanine, and the sulfonic group or carboxyl and nanometer four of the metal phthalocyanine aoxidize
The amino of three-iron is loaded by electrostatic interaction.
2. a kind of preparation method of amination nano ferriferrous oxide supported metal phthalocyanine catalyst, it is characterised in that: preparation step
Suddenly include:
(1) it weighs trivalent iron salt and acetate is dissolved in ethylene glycol, dissolution is stirred at room temperature, the organic amine being then added, stirring
The orange solution stable to formation；Reaction solution is transferred in reaction kettle, 150~220 DEG C of reactions 2~for 24 hours；Through magnetic after cooling
Separation is respectively washed for several times with deionized water and ethyl alcohol until neutral；Sample after washing is placed in a vacuum drying oven drying, i.e.,
Obtain amination nano ferriferrous oxide；
(2) amination nano ferriferrous oxide made from step (1) is added in metal phthalocyanine aqueous solution, is vibrated at room temperature
Dipping 3~be washed with deionized for 24 hours, after Magneto separate colourless to solution, the sample after Magneto separate is placed in a vacuum drying oven
It is dry, obtain amino functional nano ferriferrous oxide supported metal phthalocyanine catalyst.
3. the preparation method of amination nano ferriferrous oxide supported metal phthalocyanine catalyst according to claim 2,
Be characterized in that: organic amine described in step (1) is one of ethylenediamine, Diethylenetriamine, three second tetramines or tetren.
4. the preparation method of amination nano ferriferrous oxide supported metal phthalocyanine catalyst according to claim 2,
Be characterized in that: the mass concentration of ferric iron and acetate in ethylene glycol is respectively 20-200g/L and 20 described in step (1)
~300g/L；5~30min is stirred at room temperature；Then organic amine is added, makes volume fraction of the organic amine in mixed solution
5~50%.
5. the preparation method of amination nano ferriferrous oxide supported metal phthalocyanine catalyst according to claim 2,
Be characterized in that: amination nano ferriferrous oxide described in step (1) is prepared by solvent-thermal method, size 20~
Between 200nm.
6. the preparation method of amination nano ferriferrous oxide supported metal phthalocyanine catalyst according to claim 2,
Be characterized in that: metal phthalocyanine described in step (2) is aluminum phthalocyanine, sulfonation phthalocyanine phthalocyanine zinc, sulfonated phthalocyanine iron, sulfonated phthalocyanine
One of palladium, carboxyl aluminum phthalocyanine, carboxyl zinc phthalocyanine, carboxyl FePC.
7. the preparation method of amination nano ferriferrous oxide supported metal phthalocyanine catalyst according to claim 2,
Be characterized in that: the pH of the metal phthalocyanine aqueous solution after being added to amination nano ferriferrous oxide in step (2) is adjusted in 2~7
Between, shared mass percent is 0.1~5.0% to metal phthalocyanine in the catalyst after load, metal described in step (2)
The concentration of phthalocyanine aqueous solution is 5~100mg/L.
8. a kind of application of amination nano ferriferrous oxide supported metal phthalocyanine catalyst in Visible Light Induced Photocatalytic organic wastewater.
9. amination nano ferriferrous oxide supported metal phthalocyanine catalyst according to claim 8 has in Visible Light Induced Photocatalytic
Application in machine waste water, it is characterised in that: it is 0.01~10mM of 50mL that the catalyst that quality is 3~50mg, which is put into concentration,
Organic wastewater in, pH value be 2~12, drum air, visible light source irradiation under 30~300min remove waste water in organic dirt
Contaminate object.
10. amination nano ferriferrous oxide supported metal phthalocyanine catalyst according to claim 8 is in Visible Light Induced Photocatalytic
Application in organic wastewater, it is characterised in that: the organic waste water level nitrophenol, bisphenol-A, chlorophenol, dyestuff；Described
Visible light source is tungsten halogen lamp, sunlight or xenon lamp artificial light sources.
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