CN103586064A - Metal/graphite-like carbon nitride compound catalyst and preparing method thereof - Google Patents

Metal/graphite-like carbon nitride compound catalyst and preparing method thereof Download PDF

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CN103586064A
CN103586064A CN201310606627.7A CN201310606627A CN103586064A CN 103586064 A CN103586064 A CN 103586064A CN 201310606627 A CN201310606627 A CN 201310606627A CN 103586064 A CN103586064 A CN 103586064A
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metal
salt
graphitic nitralloy
nitralloy carbon
class graphitic
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徐杨森
李广社
李莉萍
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Fujian Institute of Research on the Structure of Matter of CAS
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Fujian Institute of Research on the Structure of Matter of CAS
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Abstract

The invention relates to a metal/graphite-like carbon nitride (g-C3N4) compound catalyst and a preparing method thereof in the field of catalysis. The chemical constitution of a metal/graphite-like carbon nitride provided by the invention is M/g-C3N4, wherein the metal M is Au, Ag, Pt, Pd, Bi, Cu, Ru or Rh, wherein the content of metal is 0-50% (mass fraction). The metal/graphite-like carbon nitride compound is a catalytic reducing agent at normal pressure and temperature, and the material is suitable for reducing derivants of nitrobenzene.

Description

Metal/class graphitic nitralloy carbon composite catalyst and preparation method thereof
Technical field
The present invention relates to metal/class graphitic nitralloy carbon composite catalyst and preparation method thereof in catalytic field
Background technology
Aniline and derivative thereof are important Organic Chemicals and medicine intermediates, are widely used in the industries such as medicine, dyestuff and rubber chemicals.The method of synthetic aniline and derivative thereof is more, by raw material, can be divided into nitrophenol method, phynol method, nitro-chlorobenzene method and nitrobenzene method.Para-aminophenol is in anil, to apply more a kind ofly, is to reduce p-nitrophenol with glass putty the earliest for the synthesis of the method for para-aminophenol.There were afterwards the iron powder reducing of employing method, electrolytic reduction or catalytic hydrogenation method to prepare para-aminophenol.Wherein the research of catalytic hydrogenation method is more, and this method be take p-nitrophenol as raw material, conventionally with Pt/C, Pd/C, makes catalyst, and diluted acid or diluted alkaline are solvent, and under about 0.2-0.5MPa, Hydrogenation is standby.But the catalyst that hydrogenating reduction is used is more expensive, and material purity is had relatively high expectations, and the cost of raw material is high, and catalyst is easily poisoning, and suitability for industrialized production is more difficult.In order to reduce the dependence to noble metal, generally adopt the noble metal catalyst of support type, be about to the noble-metal-supported of minute quantity on carrier, to reduce costs.Therefore, just having very large requirement aspect the selection of carrier, selected carrier must be able to improve the activity of catalyst and the utilization rate of noble metal.
Class graphitic nitralloy carbon (g-C 3n 4) be the novel semi-conductor catalyst of a similar graphite-structure, there is suitable semiconductor width (about 2.7eV), Stability Analysis of Structures, acid and alkali-resistance, nontoxic and bio-compatibility good, cost is low and be easy to the advantages such as chemical modification.Be used to the synthetic reaction of photocatalysis, photocatalysis price reduction pollutant, photodissociation aquatic products hydrogen and produced in oxygen and oxygen reduction reaction.And noble metal can directly load on g-C as deposited absorption, photochemical precipitation and impregnating method by chemical method 3n 4upper formation metal/g-C 3n 4hetero-junctions.This directly synthetic metal/semiconductor hetero-junctions can accelerate the transfer of interface electronics effectively, thereby improves its catalytic performance.The present invention, by the feature of comprehensive graphitic nitralloy carbon, prepares metal/graphite carbonitride compound, and as catalytic reducer, can effectively make a price reduction organic dyestuff and reduction p-nitrophenyl amphyl.
Summary of the invention
The object of this invention is to provide novel metal/class graphitic nitralloy carbon composite catalyst and preparation method thereof.
Metal/class graphitic nitralloy carbon complex prepared by the present invention, its chemical composition is M/g-C 3n 4, wherein metal M is Au, Ag, Pt, Pd, Bi, Cu, Ru or Rh.Described compound, in mass fraction, described tenor is 0~50%.
The preparation method who the invention provides described compound, comprises the steps:
(1) class graphitic nitralloy carbon is dispersed in deionized water;
(2) to above-mentioned solution, add soluble metallic salt, described soluble metal salinity is 0.02~5.0mol/L;
(3) to the aqueous solution that adds hydrazine hydrate in the solution of step (2), until complete reaction;
(4) reaction mixture solution is separated, washing, and dry.
Described soluble metallic salt is selected from HAuCl 4, AgNO 3, H 2ptCl 6, PdCl 2, BiCl 3, CuCl 2, RuCl 3, RhCl 3.
Described metal/class graphitic nitralloy carbon complex is for being reduced to nitrobenzene derivative the catalyst of anil reaction.
Described nitrobenzene derivative is selected from o-nitrophenol, metanitrophenol, p-nitrophenol, para-nitrotoluene, o-nitrobenzaldehyde, m-nitrobenzaldehyde, paranitrobenzaldehyde, ortho-nitraniline, meta nitro aniline, paranitroanilinum, parachloronitrobenzene or p-Nitrobromobenzene.
Accompanying drawing explanation
Fig. 1 is the X-ray diffracting spectrum of gold/class graphitic nitralloy carbon complex powder in embodiment 1.
Fig. 2 is the transmission electron microscope photo of gold/class graphitic nitralloy carbon complex powder in embodiment 1.
Fig. 3 is the high-resolution-ration transmission electric-lens photo of gold/class graphitic nitralloy carbon complex powder in embodiment 1.
Fig. 4 is the rate curve of gold/class graphitic nitralloy carbon complex powder catalytic reduction p-nitrophenol in embodiment 1.
Fig. 5 is the UV, visible light all-wave scanning spectra of gold/class graphitic nitralloy carbon complex powder catalytic reduction para-nitrotoluene in embodiment 1.
Fig. 6 is the UV, visible light all-wave scanning spectra of gold/class graphitic nitralloy carbon complex powder catalytic reduction paranitrobenzaldehyde in embodiment 1.
Fig. 7 is the X-ray diffracting spectrum of silver/class graphitic nitralloy carbon complex powder in embodiment 2.
Fig. 8 is the rate curve of silver/class graphitic nitralloy carbon complex powder catalytic reduction p-nitrophenol in embodiment 2.
Fig. 9 is the X-ray diffracting spectrum of platinum/class graphitic nitralloy carbon complex powder in embodiment 3.
Figure 10 is the rate curve of platinum/class graphitic nitralloy carbon complex powder catalytic reduction p-nitrophenol in embodiment 3.
Figure 11 is the X-ray diffracting spectrum of palladium/class graphitic nitralloy carbon complex powder in embodiment 4.
Figure 12 is the rate curve of palladium/class graphitic nitralloy carbon complex powder catalytic reduction p-nitrophenol in embodiment 4.
Figure 13 is the X-ray diffracting spectrum of bismuth/class graphitic nitralloy carbon complex powder in embodiment 5.
Figure 14 is the rate curve of bismuth/class graphitic nitralloy carbon complex powder catalytic reduction p-nitrophenol in embodiment 5.
Figure 15 is the X-ray diffracting spectrum of copper/class graphitic nitralloy carbon complex powder in embodiment 6.
Figure 16 is the rate curve of rhodium/class graphitic nitralloy carbon complex powder catalytic reduction p-nitrophenol in ruthenium/class graphitic nitralloy carbon, embodiment 8 in copper/class graphitic nitralloy carbon, embodiment 7 in embodiment 6.
The specific embodiment
Tester and condition
X-ray powder diffraction instrument (XRD model: Rigaku MiniFlex II), test specification: 10-70 °.
Field emission scanning electron microscope (model of FE-SEM: JEOL JSM-6700), accelerating potential: 10kV.
Transmission electron microscope (model of TEM: JEM-2010), accelerating potential: 200kV.
Ultraviolet-visible spectrometer (model of UV-vis: PerKin-Elmer, lambda35), test specification: 200-800nm.
Catalytic reduction performance test condition
It is 10ppm p-nitrophenol (para-nitrotoluene, paranitrobenzaldehyde etc.) that the metal/class graphitic nitralloy carbon complex powder that takes 10mg is scattered in 100mL concentration, adding concentration is the sodium borohydride 0.3mL of 2.0M, under stirring condition, interval sampling in 1~4 minute, each 3mL, until catalytic reduction reaction carries out completely, stop reaction.The upper strata stillness of night is got in sampling after centrifugation, and is placed in the change in concentration of testing p-nitrophenol under ultraviolet-visible spectrometer, obtains the rate curve of metal/class graphitic nitralloy carbon complex powder catalytic reduction p-nitrophenol after data processing.Under same experimental procedure, change metal/class graphitic nitralloy carbon complex powder into class graphitic nitralloy carbon, interval samples for 3 minutes, can obtain the rate curve of class graphitic nitralloy carbon dust catalytic reduction p-nitrophenol.Do not add any catalysis material, simple sodium borohydride is catalytic reduction p-nitrophenol at normal temperatures, sample interval is 3 minutes, can obtain the rate curve of p-nitrophenol under catalyst-free condition, above-mentioned catalytic rate Drawing of Curve, on same figure, just can be compared and evaluates the catalytic reduction performance of the metal/class graphitic nitralloy carbon complex the present invention relates to clearly.
By example, further illustrate feature of the present invention below, but be not limited to embodiment.Experimental technique in following embodiment, if no special instructions, is conventional method.
Embodiment 1: gold/class graphitic nitralloy carbon complex
With the g-C synthesizing 3n 4and HAuCl 4for initiation material, take the g-C of 1.5g 3n 4, add deionized water 100mL; Under the condition stirring, in above-mentioned solution, dropwise add 0.6mol/L HAuCl 4, continue to stir 30 minutes.Dropwise add the aqueous solution of hydrazine hydrate, until react completely.Then by after reaction mixture solution separation, with deionized water washing 5 times, under 80 ℃ of conditions, be dried and within 10 hours, obtain final Au/g-C 3n 4product.
The X-ray diffracting spectrum of Fig. 1 gold/class graphitic nitralloy carbon complex that for this reason prepared by embodiment.With pure g-C 3n 4x-ray diffracting spectrum contrast can know, the spectrogram of powder can index be gold and g-C 3n 4phase, without the existence of other dephasigns.Fig. 2 and Fig. 3 be transmission electron microscope photo and the high-resolution-ration transmission electric-lens photo of sample for this reason, therefrom can find out g-C 3n 4laminate structure, and the gold nano grain of the high degree of dispersion of the about 5nm of particle diameter.
This gold/class graphitic nitralloy carbon complex can be used as the catalyst under normal temperature and pressure.According to above-mentioned catalytic performance test condition, the performance curve of the catalytic reduction p-nitrophenol obtaining as shown in Figure 4.As can be seen from the figure, adding under the condition of catalyst, the speed of catalytic reduction p-nitrophenol obviously increases.Au/g-C 3n 4the time of the complete catalytic reduction p-nitrophenol of compound is 20 minutes, and its catalytic rate is not add 35 times of catalyst.
This Au/g-C 3n 4compound can be used as the catalyst under normal temperature and pressure.According to above-mentioned catalytic performance test condition, the performance curve of the catalytic reduction para-nitrotoluene obtaining as shown in Figure 5.As can be seen from the figure, along with the increase in reaction time, the maximum absorption band at 285nm place weakens gradually, and the absworption peak at 235nm place strengthens gradually, this phenomenon explanation para-nitrotoluene revert to gradually final generation para-totuidine.
This Au/g-C 3n 4compound can be used as the catalyst under normal temperature and pressure.According to above-mentioned catalytic performance test condition, the performance curve of the catalytic reduction paranitrobenzaldehyde obtaining as shown in Figure 6.As can be seen from the figure, along with the increase in reaction time, the maximum absorption band at 280nm place weakens gradually, and the absworption peak at 240nm place strengthens gradually, this phenomenon explanation paranitrobenzaldehyde revert to gradually final generation para aminotenzaldehyde.
Embodiment 2: silver/class graphitic nitralloy carbon complex
With the g-C synthesizing 3n 4and AgNO 3for initiation material.Take the g-C of 1.5g 3n 4, add deionized water 100mL, under the condition stirring, in above-mentioned solution, add 0.8mol/L AgNO 3, continue to stir 30 minutes.Dropwise add the aqueous solution of hydrazine hydrate, until react completely.Then by after reaction mixture solution separation, with deionized water washing 5 times, under 80 ℃ of conditions, be dried and within 10 hours, obtain end product.
The X-ray diffracting spectrum of Fig. 7 carbon complex that for this reason prepared by embodiment, the spectrogram of powder can index be the phase of silver and class graphitic nitralloy carbon, without the existence of other dephasigns.
This Ag/g-C 3n 4compound can be used as the catalyst under normal temperature and pressure.According to above-mentioned catalytic performance test condition, the catalytic performance curve obtaining as shown in Figure 8.As can be seen from the figure, adding under the condition of catalyst, the speed of catalytic reduction p-nitrophenol obviously increases.Now completely the time of catalytic reduction p-nitrophenol is 20 minutes, and its catalytic rate is not add 30 times of catalyst.
Embodiment 3: platinum/class graphitic nitralloy carbon complex
With the g-C synthesizing 3n 4and H 2ptCl 6for initiation material.Take the g-C of 1.5g 3n 4, add deionized water 100mL, under the condition stirring, in above-mentioned solution, add 0.2mol/L H 2ptCl 6, continue to stir 30 minutes.Dropwise add the aqueous solution of hydrazine hydrate, until react completely.Then by after reaction mixture solution separation, with deionized water washing 5 times, under 80 ℃ of conditions, be dried and within 10 hours, obtain end product.
The X-ray diffracting spectrum of Fig. 9 carbon complex that for this reason prepared by embodiment.Can know with the X-ray diffracting spectrum contrast of pure class graphitic nitralloy carbon, in compound spectrogram the diffraction maximum of platinum very a little less than.
This Pt/g-C 3n 4compound can be used as the catalyst under normal temperature and pressure.According to above-mentioned catalytic performance test condition, the catalytic performance curve obtaining as shown in figure 10.As can be seen from the figure, adding under the condition of catalyst, the speed of catalytic reduction p-nitrophenol obviously increases.Now completely the time of catalytic reduction p-nitrophenol is 10 minutes, and its catalytic rate is not add 82 times of catalyst.
Execute example 4: palladium/class graphitic nitralloy carbon complex
With the g-C synthesizing 3n 4and PdCl 2for initiation material.Take the g-C of 1.5g 3n 4, add deionized water 60mL, under the condition stirring, in above-mentioned solution, add 0.1mol/L PdCl 2, continue to stir 30 minutes.Dropwise add the aqueous solution of hydrazine hydrate, until react completely.Then by after reaction mixture solution separation, with deionized water washing 5 times, under 80 ℃ of conditions, be dried and within 10 hours, obtain end product.
The X-ray diffracting spectrum of Figure 11 compound that for this reason prepared by embodiment.Can know with the X-ray diffracting spectrum contrast of pure class graphitic nitralloy carbon, the diffraction maximum of the spectrogram palladium of palladium/class graphitic nitralloy carbon complex very a little less than.
This Pd/g-C 3n 4compound can be used as the catalyst under normal temperature and pressure.According to above-mentioned catalytic performance test condition, the catalytic performance curve obtaining as shown in figure 12.As can be seen from the figure, adding under the condition of catalyst, the speed of catalytic reduction p-nitrophenol obviously increases.Now completely the time of catalytic reduction p-nitrophenol is 6 minutes, and its catalytic rate is not add 103 times of catalyst.
Embodiment 5: bismuth/class graphitic nitralloy carbon complex
With the g-C synthesizing 3n 4and BiCl 3for initiation material.Take the g-C of 1.5g 3n 4, add deionized water 100mL, under the condition stirring, under the condition stirring, in above-mentioned solution, add 0.2g BiCl 3, continue to stir 30 minutes.Dropwise add the aqueous solution of hydrazine hydrate, until react completely.Then by after reaction mixture solution separation, with deionized water washing 5 times, under 80 ℃ of conditions, be dried and within 10 hours, obtain end product.
Figure 13 for this reason embodiment prepares the X-ray diffracting spectrum of compound, and the spectrogram of powder can index be bismuth and g-C 3n 4phase, and the crystallinity of bismuth is good.
This Bi/g-C 3n 4compound can be used as the catalyst under normal temperature and pressure.According to above-mentioned catalytic performance test condition, the catalytic performance curve obtaining as shown in figure 14.Therefrom known, when adding catalyst, the speed of catalytic reduction p-nitrophenol obviously increases.Now completely the time of catalytic reduction p-nitrophenol is 20 minutes, and its catalytic rate is not add 28 times of catalyst.
Embodiment 6: copper/class graphitic nitralloy carbon complex
With the g-C synthesizing 3n 4and CuCl 2for initiation material.The class graphitic nitralloy carbon that takes 1.5g, adds deionized water 100mL, under the condition stirring, in above-mentioned solution, adds 4.0mol/L CuCl 2, continue to stir 30 minutes.Dropwise add the aqueous solution of hydrazine hydrate, until react completely.Then by after reaction mixture solution separation, with deionized water washing 5 times, under 80 ℃ of conditions, be dried and within 10 hours, obtain end product.
With pure g-C 3n 4x-ray diffracting spectrum contrast can know, the structured testing of synthetic product shows in compound and contains elemental copper also have the cupric oxide of partial oxidation.The X-ray diffracting spectrum of Figure 15 compound that for this reason prepared by embodiment, the spectrogram of powder can index be the phase of copper, cupric oxide and class graphitic nitralloy carbon.
This bismuth/g-C 3n 4compound can be used as the catalyst under normal temperature and pressure.According to above-mentioned catalytic performance test condition, the catalytic performance curve obtaining as shown in figure 16.As can be seen from the figure, adding under the condition of catalyst, the speed of catalytic reduction p-nitrophenol obviously increases.Now the time of catalytic reduction p-nitrophenol is 10 minutes completely.
Embodiment 7: ruthenium/class graphitic nitralloy carbon complex
With the g-C synthesizing 3n 4and RuCl 3for initiation material.The class graphitic nitralloy carbon that takes 1.5g, adds deionized water 100mL, under the condition stirring, in above-mentioned solution, adds 0.03mol/L RuCl 3, continue to stir 30 minutes.Dropwise add the aqueous solution of hydrazine hydrate, until react completely.Then by after reaction mixture solution separation, with deionized water washing 5 times, under 80 ℃ of conditions, be dried and within 10 hours, obtain end product.
This Ru/g-C 3n 4can be used as the catalyst under normal temperature and pressure.According to above-mentioned catalytic performance test condition, the catalytic performance curve obtaining as shown in figure 16.As can be seen from the figure, adding under the condition of catalyst, the speed of catalytic reduction p-nitrophenol obviously increases.
Embodiment 8: rhodium/class graphitic nitralloy carbon complex
With the g-C synthesizing 3n 4and RhCl 3for initiation material.The class graphitic nitralloy carbon that takes 1.5g, adds deionized water 100mL, under the condition stirring, in above-mentioned solution, adds 0.02mol/L RhCl 3, continue to stir 30 minutes.Dropwise add the aqueous solution of hydrazine hydrate, until react completely.Then by after reaction mixture solution separation, with deionized water washing 5 times, under 80 ℃ of conditions, be dried and within 10 hours, obtain end product.
This Rh/g-C 3n 4can be used as the catalyst under normal temperature and pressure.According to above-mentioned catalytic performance test condition, the catalytic performance curve obtaining as shown in figure 16.As can be seen from the figure, adding under the condition of catalyst, the speed of catalytic reduction p-nitrophenol obviously increases.

Claims (10)

1. metal/class graphitic nitralloy carbon complex, is characterized in that: its chemical composition is M/g-C 3n 4, wherein M is selected from Au, Ag, Cu, Fe, Pt, Pd, Sn, Bi, Zn, Ru or Rh.
2. compound as claimed in claim 1, is characterized in that: in mass fraction, described tenor is 0~50%.
3. the photoreduction met hod of compound described in preparation claim 1, comprise the steps: take that class graphitic nitralloy carbon and soluble metallic salt silver nitrate are initiation material, take the class graphitic nitralloy carbon of 1.5g, add deionized water 100mL, under the condition stirring, in above-mentioned solution, add silver nitrate, continue to stir 30 minutes; Open light source, photo-reduction 60 minutes, then by after reaction mixture solution separation, with deionized water washing 5 times, the dry end product that obtains for 10 hours under 80 ℃ of conditions.
4. preparation method according to claim 3, is characterized in that: described silver salt, golden salt and palladium salt are respectively silver nitrate, gold chloride and palladium bichloride; Described platinum salt is one or both in potassium chloroplatinate or chloroplatinic acid; Described mantoquita is selected from greening copper, afforests one or more in cuprous, copper nitrate, copper acetate, copper sulphate or cupric oxalate; Described molysite is selected from one or more in greening iron, greening ferrous iron, ferric nitrate, ferric acetate, ferric sulfate, ferrous sulfate ammonia or ferric oxalate; Described pink salt is selected from four tin chlorides, afforests sub-tin, one or more in nitric acid tin, STANNOUS SULPHATE CRYSTALLINE; Described bismuth salt is selected from one or more in greening bismuth, bismuth nitrate, pucherite, BiOX or bismuth molybdate; Described zinc salt is selected from one or more in greening zinc, zinc nitrate, zinc acetate, zinc sulfate; Described ruthenium salt and rhodium salt are selected from each self-corresponding greening thing salt.
5. preparation method according to claim 3, it is characterized in that: in described photoreduction met hod, hydrothermal reduction method and chemical reducing agent reducing process, add and be selected from potassium hydroxide, one or more in NaOH, nitric acid, hydrochloric acid, oxalic acid, ammoniacal liquor, citric acid, polyvinyl alcohol, polyethylene glycol or urea as additive.
6. the preparation method of metal/class graphitic nitralloy carbon complex according to claim 3, is characterized in that: described hydrothermal reduction reaction temperature is 80~140 ℃.
7. the preparation method of metal/class graphitic nitralloy carbon complex according to claim 3, is characterized in that: in described electronation, reducing agent is a kind of in hydrogen, sodium borohydride or hydrazine hydrate.
8. metal/class graphitic nitralloy carbon complex according to claim 1 is as the application of the catalytic reduction under normal temperature and pressure.
9. the application of metal/class graphitic nitralloy carbon complex according to claim 8, is characterized in that: it is anil that described material is applicable to reduce nitrobenzene derivative.
10. the application of metal/class graphitic nitralloy carbon complex according to claim 9, is characterized in that: described nitrobenzene derivative comprises o-nitrophenol, metanitrophenol, p-nitrophenol, para-nitrotoluene, o-nitrobenzaldehyde, m-nitrobenzaldehyde, paranitrobenzaldehyde, ortho-nitraniline, meta nitro aniline, paranitroanilinum, parachloronitrobenzene, p-Nitrobromobenzene.
CN201310606627.7A 2013-11-26 2013-11-26 Metal/graphite-like carbon nitride compound catalyst and preparing method thereof Pending CN103586064A (en)

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