CN109701638A - A kind of catalytic hydrogenation Pd-IL/AC catalyst and its preparation method and application being catalyzed halogenated aryl hydrocarbon object - Google Patents
A kind of catalytic hydrogenation Pd-IL/AC catalyst and its preparation method and application being catalyzed halogenated aryl hydrocarbon object Download PDFInfo
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Abstract
The present invention relates to a kind of catalytic hydrogenation Pd-IL/AC catalyst and its preparation method and application for being catalyzed halogenated aryl hydrocarbon object, belong to wastewater treating technology field.In order to solve the problems, such as that existing catalytic activity and stability are poor, a kind of catalytic hydrogenation Pd-IL/AC catalyst and preparation method and application being catalyzed halogenated aryl hydrocarbon object is provided, it is weighed in corresponding soluble palladium salt and ionic liquid starting material and carrier active carbon according to load capacity, obtains solidliquid mixture sample；Continue reduction treatment after being dried again in a hydrogen atmosphere, obtains corresponding catalytic hydrogenation Pd-IL/AC catalyst.The carrier of the catalyst is active carbon；First group is divided into Pd, and second group is divided into IL, and IL is a kind of ionic liquid.The specific palladium catalyst large specific surface area of the present invention, metal dispersion and thermal stability are good, and have the effect of that the activity of catalysis and stability are high.
Description
Technical field
The present invention relates to a kind of catalytic hydrogenation Pd-IL/AC catalyst for being catalyzed halogenated aryl hydrocarbon object and preparation method thereof and answer
With belonging to wastewater treating technology field.
Background technique
Halogenated phenolic compound is very common industrial chemicals and organic solvent in industries such as chemical industry, medicine.Pesticide,
It is also widely used in dyestuff.But this kind of compound is that one kind is difficult to the organic compound degraded, pollution life in the environment
State environment, while also by it is believed that also having very with carcinogenic, teratogenesis, mutagenic effect, and to the health of daily human body
Big influence.Due to containing chlorine element in the organic matter, and chlorine element has a great impact to the pollution of environment, therefore, if will
Chlorine element in compound removes, its toxicity can be effectively reduced and ring.2-chlorophenol (2-CP), 2,4 chlorophenesic acids (2,4-DCP),
The organic compounds such as 2,4,6- trichlorophenols (2,4,6-TCP) are paid attention to by Environmental Protection in China office and EPA (U.S.EPA), be included in after
Among the blacklist of continuous processing.Catalytic hydrogenation and dechlorination (hydrodechlorination, HDC) belongs in electronation technology
One kind, the technology are to replace the halogen atom in halogenated phenols to reach the de- of Pyrogentisinic Acid using reactive hydrogen provided by catalyst
Chlorine.HDC is to restore chlorophenol by catalytic hydrogenation and generate pollution-free recyclable compound, not only can remove halogen
For organic matter, and product can be recycled, collection utilizes herein.In order to more effectively remove pollutant, stability is prepared
Height, catalytic is strong, and selectivity waits the catalyst of excellent properties to be very important well.
Ionic liquid is non-volatile, non-combustible, electric conductivity is strong, the viscosity of ionic liquid is very big at room temperature, and its thermal capacitance is big, steams
Vapour pressure is small, property is stable, has good dissolubility to many inorganic salts and organic matter, in electrochemistry, organic synthesis, catalysis, divides
It is widely used from equal fields.Since ionic liquid can dissolve section transitions metal, thus to use ion in hydrogenation
Liquid has laid good basis.
Summary of the invention
For the above the deficiencies in the prior art, the present invention provides a kind of catalytic hydrogenation for being catalyzed halogenated aryl hydrocarbon object
Pd-IL/AC catalyst and its preparation method and application solves the problems, such as it is how to improve catalyst activity and stability to make to improve
To the catalytic capability of halogenated aryl hydrocarbon object.
An object of the present invention technical scheme is that, it is a kind of be catalyzed halogenated aryl hydrocarbon object catalysis
Add hydrogen Pd-IL/AC catalyst, which is characterized in that the carrier of catalyst is active carbon；First group is divided into Pd, and second group is divided into IL,
IL is a kind of ionic liquid.
In the catalytic hydrogenation Pd-IL/AC catalyst of above-mentioned catalysis halogenated aryl hydrocarbon object, preferably, the IL is 1- fourth
Base -3- methylimidazole trichloroacetate.The IL improves the dispersion degree of Pd nano particle, improves the activity and stabilization of catalysis
Property；The surface chemistry conditions for changing Pd are conducive to modulation Pd0And Pd2+Ratio, be applicable in different hydrogenation reactions.
In the catalytic hydrogenation Pd-IL/AC catalyst of above-mentioned catalysis halogenated aryl hydrocarbon object, preferably, the catalyst
Palladium load capacity is the 1% of carrier, and ionic liquid loaded amount is the 20% of carrier.Such proportion has reached suitable Pdn+/Pd0
Ratio, so that hydrogenation-dechlorination effect is substantially improved, and suitable ILx+-Pd0Ratio becomes stable catalyst.Institute in the present invention
The halogenated aryl hydrocarbon said can be monosubstituted or polysubstituted mode, such as chlorophenol, bromophenol or chlorophenesic acid, can be with
It is halogenated polycyclic aromatic hydrocarbon object etc..
The second object of the present invention is to what is be achieved by the following technical programs, a kind of catalysis being catalyzed halogenated aryl hydrocarbon object
Add the preparation method of hydrogen Pd-IL/AC catalyst, which is characterized in that method includes the following steps:
A, corresponding soluble palladium salt and ionic liquid starting material are weighed according to load capacity, is dissolved in stir in organic solvent and mixes
After closing uniformly, liquid mixture is taken out, incipient impregnation obtains solidliquid mixture sample on carrier active carbon.
B, the solidliquid mixture sample that above-mentioned steps A is obtained is dried；
C, the solidliquid mixture sample after being dried above-mentioned steps B continues reduction treatment in a hydrogen atmosphere, obtains
Corresponding catalytic hydrogenation Pd-IL/AC catalyst.
In the preparation method of the catalytic hydrogenation Pd-IL/AC catalyst of above-mentioned catalysis halogenated aryl hydrocarbon object, preferably,
The drying temperature of drying process described in step B is 70 DEG C -85 DEG C, drying time 8-10h.
In the preparation method of the catalytic hydrogenation Pd-IL/AC catalyst of above-mentioned catalysis halogenated aryl hydrocarbon object, preferably,
The hydrogen temperature of hydrogen atmosphere described in step C is 180 DEG C -200 DEG C, and the time of reduction treatment is 1-3h.
The third object of the present invention technical scheme is that, a kind of above-mentioned catalysis halogenated aryl hydrocarbon object
The application of catalytic hydrogenation Pd-IL/AC catalyst, which is characterized in that the catalytic hydrogenation Pd-IL/AC catalyst is used for halogenated virtue
The catalytic hydrogenation and dechlorination of hydrocarbon object, the hydrogen source that the catalytic hydrogenation and dechlorination uses are selected from hydrogen or formic acid-sodium formate.Hydrogen is as hydrogen
Source, cleaning, pollution-free, high-efficient, storage and transportation performance are good；And formic acid-sodium formate is as hydrogen source, relative to high pressure hydrogen,
Secure context has great advantage.Furthermore formic acid-sodium formate has good selective reduction, and reaction condition is mild, post-processing letter
Just.
Compared with prior art, the invention has the following advantages that
1. palladium catalyst large specific surface area, metal dispersion and thermal stability are good.
2. ionic liquid improves the dispersion degree of Pd nano particle, the activity and stability of catalysis, ionic liquid structural reform are improved
The surface chemistry conditions for having become Pd are conducive to modulation Pd0And Pd2+Ratio, be applicable in different hydrogenation reactions.
Detailed description of the invention
Fig. 1 is the stereoscan photograph (scale 20nm) of Pd-IL/AC catalyst prepared by the embodiment of the present invention 1.
Fig. 2 is the stereoscan photograph (scale 50nm) of Pd-IL/AC catalyst prepared by the embodiment of the present invention 1.
Fig. 3 is the FTIR map of Pd-IL/AC catalyst prepared by the embodiment of the present invention 1.
Fig. 4 is that the activity of Pd-IL/AC catalyst prepared by the embodiment of the present invention 1 investigates result.
Specific embodiment
Below by specific embodiments and the drawings, the technical solutions of the present invention will be further described, but this
Invention is not limited to these examples.
Embodiment one
1, prepared by catalyst Pd-IL/AC: weighing 1g activated carbon with electronic balance, 0.2g ion is added into round-bottomed flask
Liquid (1- butyl -3- methylimidazole trichloroacetate), 1.67ml H2PdCl4(0.1g/ml) solution and enough organic molten
Agent (anhydrous methanol) stirs 1h at 40 DEG C, and rear incipient impregnation is on 1g active carbon.Product is placed in 100 DEG C of drying boxes
Dry 8h, grinding, product restores (H in tube furnace after then grinding2Atmosphere, 200 DEG C), ground after reduction.It finally obtains
Palladium supported ion liquid activated carbon, is named as Pd-IL/AC catalyst.
2, it weighs 0.8g substrate tetrachlorophenol (4-CP) to be dissolved in 100ml deionized water, then pours into volumetric flask；
3, it takes 10ml water in clean round-bottomed flask, while the configured substrate of 10ml (8g/L), 10ml configuration is added
Good formic acid-sodium formate solution (1mol/L-0.8mol/L) is added magneton, is eventually adding Pd-IL/AC catalyst 0.05g.
4, reaction condition are as follows: 30 DEG C of water-baths open stirring, start simultaneously at timing.
5, reaction time 120min, in 10,20,30,60,120min sampling, promoting the circulation of qi analysis of hplc sample sets of going forward side by side
At.
6, chlorophenol degradation rate is 99%, phenol product 90%, cyclohexanone 8%, cyclohexanol 1%.
It randomly selects corresponding product obtained above to be tested accordingly, test result is as Figure 1-Figure 4, specifically may be used
To find out, Fig. 1 shows that IL reduces the size of Pd nano particle and improves the dispersion degree of Pd nano particle.Fig. 2 shows IL
It reduces the size of Pd nano particle and improves the dispersion degree of Pd nano particle.Fig. 3 shows that IL has been supported on carrier.
Fig. 4 shows that the Pd-IL/AC catalyst of preparation has good effect for the catalytic hydrogenation and dechlorination of chlorinated aromatic hydrocarbons object.
Embodiment two
1, prepared by catalyst Pd-IL/AC: weighing 1g activated carbon with electronic balance, 0.2g ion is added into round-bottomed flask
Liquid (1- butyl -3- methylimidazole trichloroacetate), 1.67ml H2PdCl4(0.1g/ml) solution and enough organic molten
Agent (anhydrous methanol) stirs 1h at 40 DEG C, and rear incipient impregnation is on 1g active carbon.Product is placed in 100 DEG C of drying boxes
Dry 8h, grinding, product restores (H in tube furnace after then grinding2Atmosphere, 200 DEG C), ground after reduction.It finally obtains
Palladium supported ion liquid activated carbon, is named as Pd-IL/AC catalyst.
2, it weighs 0.8g substrate tetrachlorophenol (4-CP) to be dissolved in 100ml deionized water, then pours into volumetric flask；
3, it takes 10ml water in clean round-bottomed flask, while the configured substrate of 10ml (8g/L), 10ml configuration is added
Good formic acid-sodium formate solution (1mol/L-0.8mol/L) is added magneton, is eventually adding Pd-IL/AC catalyst 0.05g.
4, reaction condition are as follows: 40 DEG C of water-baths open stirring, start simultaneously at timing.
5, reaction time 120min, in 10,20,30,60,120min sampling, promoting the circulation of qi analysis of hplc sample sets of going forward side by side
At.
6, chlorophenol degradation rate is 99%, phenol product 90%, cyclohexanone 7%, cyclohexanol 2%.
Embodiment three
1, prepared by catalyst Pd-IL/AC: weighing 1g activated carbon with electronic balance, 0.2g ion is added into round-bottomed flask
Liquid (1- butyl -3- methylimidazole trichloroacetate), 1.67ml H2PdCl4(0.1g/ml) solution and enough organic molten
Agent (anhydrous methanol) stirs 1h at 40 DEG C, and rear incipient impregnation is on 1g active carbon.Product is placed in 100 DEG C of drying boxes
Dry 8h, grinding, product restores (H in tube furnace after then grinding2Atmosphere, 220 DEG C), ground after reduction.It finally obtains
Palladium supported ion liquid activated carbon, is named as Pd-IL/AC catalyst.
2, it weighs 0.8g substrate tetrachlorophenol (4-CP) to be dissolved in 100ml deionized water, then pours into volumetric flask；
3, it takes 10ml water in clean round-bottomed flask, while the configured substrate of 10ml (8g/L), 10ml configuration is added
Good formic acid-sodium formate solution (1mol/L-0.8mol/L) is added magneton, is eventually adding Pd-IL/AC catalyst 0.05g.
4, reaction condition are as follows: 30 DEG C of water-baths open stirring, start simultaneously at timing.
5, reaction time 120min, in 10,20,30,60,120min sampling, promoting the circulation of qi analysis of hplc sample sets of going forward side by side
At.
6, chlorophenol degradation rate is 97%, phenol product 88%, cyclohexanone 7%, cyclohexanol 2%.
Example IV
1. prepared by catalyst Pd-IL/AC: weighing 1g activated carbon with electronic balance, 0.2g ion is added into round-bottomed flask
Liquid (1- butyl -3- methylimidazole trichloroacetate), 1.67ml H2PdCl4(0.1g/ml) solution and enough organic molten
Agent (anhydrous methanol) stirs 1h at 50 DEG C, and rear incipient impregnation is on 1g active carbon.Product is placed in 120 DEG C of drying boxes
Dry 10h, grinding, product restores (H in tube furnace after then grinding2Atmosphere, 200 DEG C), ground after reduction.It finally obtains
Palladium supported ion liquid activated carbon, is named as Pd-IL/AC catalyst.
2, it weighs 0.8g substrate tetrachlorophenol (4-CP) to be dissolved in 100ml deionized water, then pours into volumetric flask；
3, it takes 10ml water in clean round-bottomed flask, while the configured substrate of 10ml (8g/L), 10ml configuration is added
Good formic acid-sodium formate solution (1mol/L-0.8mol/L) is added magneton, is eventually adding Pd-IL/AC catalyst 0.05g.
4, reaction condition are as follows: 30 DEG C of water-baths open stirring, start simultaneously at timing.
5, reaction time 120min, in 10,20,30,60,120min sampling, promoting the circulation of qi analysis of hplc sample sets of going forward side by side
At.
6, chlorophenol degradation rate is 98%, phenol product 90%, cyclohexanone 7%, cyclohexanol 1%.
Embodiment five
1. prepared by catalyst Pd-IL/AC: weighing 1g activated carbon with electronic balance, 0.2g ion is added into round-bottomed flask
Liquid (1- butyl -3- methylimidazole trichloroacetate), 1.67ml H2PdCl4(0.1g/ml) solution and enough organic molten
Agent (anhydrous methanol) stirs 1h at 40 DEG C, and rear incipient impregnation is on 1g active carbon.Product is placed in 100 DEG C of drying boxes
Dry 8h, grinding, product restores (H in tube furnace after then grinding2Atmosphere, 200 DEG C), ground after reduction.It finally obtains
Palladium supported ion liquid activated carbon, is named as Pd-IL/AC catalyst.
2, it weighs 0.8g substrate tetrachlorophenol (4-CP) to be dissolved in 100ml deionized water, then pours into volumetric flask；
3, it takes 10ml water in clean round-bottomed flask, while the configured substrate of 10ml (8g/L), 10ml configuration is added
Good formic acid-sodium formate solution (1mol/L-0.8mol/L) is added magneton, is eventually adding Pd-IL/AC catalyst 0.08g.
4, reaction condition are as follows: 30 DEG C of water-baths open stirring, start simultaneously at timing.
5, reaction time 120min, in 10,20,30,60,120min sampling, promoting the circulation of qi analysis of hplc sample sets of going forward side by side
At.
6, chlorophenol degradation rate is 99%, phenol product 92%, cyclohexanone 6%, cyclohexanol 1%.
Corresponding chlorophenol is also possible to other halogenated phenols or halogenated aryl hydrocarbon object, such as bromophenol in the present embodiment
Or chlorophenesic acid etc..
Specific embodiment described in the present invention only illustrate the spirit of the present invention by way of example.The neck of technology belonging to the present invention
The technical staff in domain can make various modifications or additions to the described embodiments or replace by a similar method
In generation, however, it does not deviate from the spirit of the invention or beyond the scope of the appended claims.
It is skilled to this field although present invention has been described in detail and some specific embodiments have been cited
For technical staff, as long as it is obvious for can making various changes or correct without departing from the spirit and scope of the present invention.
Claims (7)
1. a kind of catalytic hydrogenation Pd-IL/AC catalyst for being catalyzed halogenated aryl hydrocarbon object, which is characterized in that the carrier of the catalyst is
Active carbon；First component is Pd, and second group is divided into IL, and IL is a kind of ionic liquid.
2. being catalyzed the catalytic hydrogenation Pd-IL/AC catalyst of halogenated aryl hydrocarbon object according to claim 1, which is characterized in that described
IL is 1- butyl -3- methylimidazole trichloroacetate.
3. being catalyzed the catalytic hydrogenation Pd-IL/AC catalyst of halogenated aryl hydrocarbon object according to claim 1, which is characterized in that described
The load capacity of palladium is the 1% of carrier, and the load capacity of ionic liquid is the 20% of carrier.
4. a kind of preparation method for the catalytic hydrogenation Pd-IL/AC catalyst for being catalyzed halogenated aryl hydrocarbon object, which is characterized in that this method
The following steps are included:
A, corresponding soluble palladium salt is weighed according to load capacity and ionic liquid starting material is dissolved in organic solvent and is stirred
After even, liquid mixture is taken out, incipient impregnation obtains solidliquid mixture sample on carrier active carbon.
B, the solidliquid mixture sample that above-mentioned steps A is obtained is dried；
C, the solidliquid mixture sample after being dried above-mentioned steps B continues reduction treatment in a hydrogen atmosphere, obtains corresponding
Catalytic hydrogenation Pd-IL/AC catalyst.
5. it is catalyzed the preparation method of the catalytic hydrogenation Pd-IL/AC catalyst of halogenated aryl hydrocarbon object according to claim 4, it is special
Sign is that the drying temperature of drying process described in step B is 70 DEG C -85 DEG C, drying time 8-10h.
6. it is catalyzed the preparation method of the catalytic hydrogenation Pd-IL/AC catalyst of halogenated aryl hydrocarbon object according to claim 4, it is special
Sign is that the reduction temperature of hydrogen atmosphere described in step C is 180 DEG C -200 DEG C, and the time of reduction treatment is 1-3h.
7. a kind of catalytic hydrogenation Pd-IL/AC catalyst for being catalyzed halogenated aryl hydrocarbon object as described in claim 1-3 any one is answered
With, which is characterized in that the catalytic hydrogenation Pd-IL/AC catalyst is used for the catalytic hydrogenation and dechlorination of halogenated aryl hydrocarbon object, the catalysis
The hydrogen source that hydrogenation-dechlorination uses is selected from hydrogen, formic acid-sodium formate, methanol, ethyl alcohol or ethylene glycol.
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Cited By (2)
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| CN111250158A (en) * | 2019-11-29 | 2020-06-09 | 浙江工业大学 | Carbon-supported alkaline ionic liquid-metal catalyst and preparation and application thereof |
| CN111282592A (en) * | 2019-11-29 | 2020-06-16 | 浙江工业大学 | Carbon-supported alkaline ionic liquid-metal catalyst, preparation thereof and application thereof in catalytic transfer hydrogenation reaction |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111250158A (en) * | 2019-11-29 | 2020-06-09 | 浙江工业大学 | Carbon-supported alkaline ionic liquid-metal catalyst and preparation and application thereof |
| CN111282592A (en) * | 2019-11-29 | 2020-06-16 | 浙江工业大学 | Carbon-supported alkaline ionic liquid-metal catalyst, preparation thereof and application thereof in catalytic transfer hydrogenation reaction |
| CN111250158B (en) * | 2019-11-29 | 2023-04-11 | 浙江工业大学 | Carbon-supported alkaline ionic liquid-metal catalyst and preparation and application thereof |
| CN111282592B (en) * | 2019-11-29 | 2023-07-21 | 浙江工业大学 | Carbon-supported alkaline ionic liquid-metal catalyst, preparation thereof and application thereof in catalytic transfer hydrogenation reaction |
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Application publication date: 20190503 |