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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carbon nitride
nitrophenol
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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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Abstract

本发明涉及催化领域中金属/类石墨氮化碳（g-C3N4）复合物催化剂及其制备方法。本发明提供的金属/类石墨氮化碳的化学组成为M/g-C3N4，其中金属M为Au、Ag、Pt、Pd、Bi、Cu、Ru或Rh，金属的含量为0～50%（质量分数）。所述的金属/类石墨氮化碳复合物作为常温常压下的催化还原剂，所述的材料适合于还原硝基苯衍生物。

Figure 201310606627

The invention relates to a metal/graphite-like carbon nitride (gC 3 N 4 ) composite catalyst in the field of catalysis and a preparation method thereof. The chemical composition of the metal/graphite-like carbon nitride provided by the present invention is M/gC 3 N 4 , wherein the metal M is Au, Ag, Pt, Pd, Bi, Cu, Ru or Rh, and the metal content is 0-50% (quality score). The metal/graphite-like carbon nitride compound is used as a catalytic reducing agent under normal temperature and pressure, and the material is suitable for reducing nitrobenzene derivatives.

Figure 201310606627

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.金属/类石墨氮化碳复合物，其特征在于：其化学组成为M/g-C3N4，其中M选自Au,Ag,Cu,Fe,Pt,Pd,Sn,Bi,Zn,Ru或Rh。1. Metal/graphite-like carbon nitride composite, characterized in that its chemical composition is M/gC 3 N 4 , wherein M is selected from Au, Ag, Cu, Fe, Pt, Pd, Sn, Bi, Zn, Ru or Rh. 2.如权利要求1所述的复合物，其特征在于：以质量分数计，所述金属含量为0～50%。2. The compound according to claim 1, characterized in that, the metal content is 0-50% in mass fraction. 3.制备权利要求1所述复合物的光还原法，包括如下步骤：以类石墨氮化碳和可溶性金属盐硝酸银为起始原料，称取1.5g的类石墨氮化碳，加去离子水100mL，在搅拌的条件下，向上述溶液中加入硝酸银，继续搅拌30分钟；开启光源，光还原60分钟，然后将反应混合物溶液分离后，用去离子水洗涤5次，在80℃条件下干燥10小时得到最终产物。3. prepare the photoreduction method of the compound described in claim 1, comprise the steps: take class graphitic carbon nitride and soluble metal salt silver nitrate as starting raw material, take the class graphitic carbon nitride of 1.5g, add deionized Water 100mL, under the condition of stirring, add silver nitrate to the above solution, continue to stir for 30 minutes; turn on the light source, light reduction for 60 minutes, then separate the reaction mixture solution, wash with deionized water 5 times, at 80 ℃ Drying at low temperature for 10 hours gave the final product. 4.根据权利要求3所述的制备方法，其特征在于：所述的银盐、金盐和钯盐分别为硝酸银、氯金酸和氯化钯；所述的铂盐为氯铂酸钾或氯铂酸中的一种或两种；所述的铜盐选自绿化铜、绿化亚铜、硝酸铜、乙酸铜、硫酸铜或草酸铜中的一种或几种；所述的铁盐选自绿化铁、绿化亚铁、硝酸铁、乙酸铁、硫酸铁、硫酸亚铁氨或草酸铁中的一种或几种；所述的锡盐选自四绿化锡、绿化亚锡、硝酸锡、硫酸锡中的一种或几种；所述的铋盐选自绿化铋、硝酸铋、钒酸铋、卤氧化铋或钼酸铋中的一种或几种；所述的锌盐选自绿化锌、硝酸锌、乙酸锌、硫酸锌中的一种或几种；所述的钌盐和铑盐选自各自对应的绿化物盐。4. preparation method according to claim 3 is characterized in that: described silver salt, gold salt and palladium salt are silver nitrate, chloroauric acid and palladium chloride respectively; Described platinum salt is potassium chloroplatinate or one or both of chloroplatinic acid; the copper salt is selected from one or more of copper green, cuprous green, copper nitrate, copper acetate, copper sulfate or copper oxalate; the iron salt One or more selected from green iron, green ferrous, ferric nitrate, ferric acetate, ferric sulfate, ferrous ammonium sulfate or ferric oxalate; the tin salt is selected from tetragreen tin, green tin, tin nitrate , one or more of tin sulfate; the bismuth salt is selected from one or more of green bismuth, bismuth nitrate, bismuth vanadate, bismuth oxyhalide or bismuth molybdate; the zinc salt is selected from One or more of zinc green, zinc nitrate, zinc acetate, zinc sulfate; the ruthenium salt and rhodium salt are selected from the corresponding green salts. 5.根据权利要求3所述的制备方法，其特征在于：所述的光还原法、水热还原法以及化学还原剂还原法中，加入选自氢氧化钾、自氢氧化钠、硝酸、盐酸、草酸、氨水、柠檬酸、聚乙烯醇、聚乙二醇或尿素中的一种或几种作为添加剂。5. preparation method according to claim 3 is characterized in that: in described photoreduction method, hydrothermal reduction method and chemical reductant reduction method, add and be selected from potassium hydroxide, self-sodium hydroxide, nitric acid, hydrochloric acid , oxalic acid, ammonia water, citric acid, polyvinyl alcohol, polyethylene glycol or urea as additives. 6.根据权利要求3所述的金属/类石墨氮化碳复合物的制备方法，其特征在于：所述的水热还原反应温度为80～140℃。6. The method for preparing metal/graphite-like carbon nitride composites according to claim 3, characterized in that: the temperature of the hydrothermal reduction reaction is 80-140°C. 7.根据权利要求3所述的金属/类石墨氮化碳复合物的制备方法，其特征在于：所述的化学还原中还原剂为氢气、硼氢化钠或水合肼中的一种。7. The method for preparing metal/graphite-like carbon nitride composites according to claim 3, characterized in that: the reducing agent in the chemical reduction is one of hydrogen, sodium borohydride or hydrazine hydrate. 8.根据权利要求1所述的金属/类石墨氮化碳复合物作为常温常压下的催化还原的应用。8. The application of the metal/graphitic carbon nitride compound according to claim 1 as catalytic reduction under normal temperature and pressure. 9.根据权利要求8所述的金属/类石墨氮化碳复合物的应用，其特征在于：所述的材料适用于还原硝基苯衍生物为苯胺衍生物。9. The application of the metal/graphite-like carbon nitride composite according to claim 8, characterized in that: said material is suitable for reducing nitrobenzene derivatives to aniline derivatives. 10.根据权利要求9所述的金属/类石墨氮化碳复合物的应用，其特征在于：所述的硝基苯衍生物包括邻硝基苯酚、间硝基苯酚、对硝基苯酚、对硝基甲苯、邻硝基苯甲醛、间硝基苯甲醛、对硝基苯甲醛、邻硝基苯胺、间硝基苯胺、对硝基苯胺、对氯硝基苯、对溴硝基苯。10. The application of the metal/graphitic carbon nitride compound according to claim 9, characterized in that: the nitrobenzene derivatives include o-nitrophenol, m-nitrophenol, p-nitrophenol, p-nitrophenol, Nitrotoluene, o-nitrobenzaldehyde, m-nitrobenzaldehyde, p-nitrobenzaldehyde, o-nitroaniline, m-nitroaniline, p-nitroaniline, p-chloronitrobenzene, p-bromonitrobenzene.
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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CN115364886A (en) * 2022-06-20 2022-11-22 山东大学 Plasma photocatalytic material and application thereof in carbon dioxide cycloaddition reaction
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