CN107952466A - In methods of the h-BN as catalyst reduction p-nitrophenol for loading Au or Pd - Google Patents
In methods of the h-BN as catalyst reduction p-nitrophenol for loading Au or Pd Download PDFInfo
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- CN107952466A CN107952466A CN201711440286.5A CN201711440286A CN107952466A CN 107952466 A CN107952466 A CN 107952466A CN 201711440286 A CN201711440286 A CN 201711440286A CN 107952466 A CN107952466 A CN 107952466A
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- catalyst
- nitrophenol
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- B01J37/031—Precipitation
- B01J37/035—Precipitation on carriers
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/70—Treatment of water, waste water, or sewage by reduction
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/34—Organic compounds containing oxygen
- C02F2101/345—Phenols
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/38—Organic compounds containing nitrogen
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- Life Sciences & Earth Sciences (AREA)
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- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention discloses a kind of h BN to load Au or Pd as the method for catalyst reduction p-nitrophenol, include the following steps：(1) dose volume ratio is 1:1 ethylene glycol:Aqueous solution, is put into h BN powder, and ultrasound makes it be uniformly dispersed, and adds the sodium citrate of 2 wt%, and ultrasound makes its dissolving；(2) H is added2PdCl4Solution or HAuCl4Solution, concussion 2 h of absorption, pH to 9 11 is adjusted with NaOH aqueous solutions, and 10 min are centrifuged with 4000 rpm, deionized water centrifuge washing three times, then with ethanol centrifuge washing three times；(3) clear liquid is abandoned, adds NaBH4Aqueous solution, stands 0.5 h of reaction, centrifuges 10 min with 4000 rpm, deionized water centrifuge washing three times, then with ethanol centrifuge washing three times, takes deposit to obtain catalyst in oven for drying；(4) water, p-nitrophenol, NaBH are added4Aqueous solution, stirs evenly, and adds catalyst and carries out reduction reaction, in-situ tracking.The present invention is participated in without hydrogen, and high income, reduces that the quality of p-nitrophenol is good, and pollution is small.
Description
Technical field
The present invention relates to a kind of methods of the h-BN as catalyst reduction p-nitrophenol to load Au or Pd.
Background technology
P-nitrophenol is a kind of is widely applied in the fine chemical product production process such as dyestuff, pesticide, medicine
Important organic synthesis raw material.Largely the waste water containing p-nitrophenol is with the fast-developing and more and more of Fine Chemical Industry
Be discharged into environment so that p-nitrophenol concentration increases sharply in earth's surface and underground water.Because of its nitro and hydroxyl and benzene
The conjugation of ring, so p-nitrophenol is difficult to be biodegradable, while the biodegradable nitroso produced and azanol are also
Carcinogenic substance.P-nitrophenol can be enriched with aquatile body, can extended stationary periods in water body environment, and it is not easy with steam
Volatilization, has serious pollution to environment.It can influence the mankind by breathing the approach such as suction, food intake, skin contact
Health, strong suction can cause expiratory dyspnea, body temperature rise, headache, nausea etc., death is resulted even in when serious.Cause
This, China and U.S.EPA have been classified as one of priority pollutants.Though p-nitrophenol is important organic conjunction
Into raw material, but the environmental pollution produced in its production process also should not be underestimated.So the life of p-nitrophenol how can be increased
Force of labor degree can reduce its pollution to environment again becomes the hot spot of more and more researchers concern.
At present, the domestic processing method on the waste water containing p-nitrophenol mainly has：Physical, bioanalysis and chemical method.
And p-nitrophenol catalysis is reduced to para-aminophenol, it is the major way for handling this type waste water.Gone compared to traditional
Except method, catalytic reduction method is because reaction condition is gentle, dangerous low, reduzate chemo-selective is high and environmental-friendly etc. excellent
Put and have broad application prospects.And the reduzate of p-nitrophenol catalytic hydrogenation -- para-aminophenol, can answer extensively
For medication chemistry industry.Para-aminophenol can be used as medicine intermediate, synthesis paracetamol, clofibrate, 6 monohydroxy quinoline,
The medicine such as benoral and practolol.In addition, para-aminophenol can be directly used as the additive of antioxidant and petroleum product, also may be used
For synthesis p-phenylenediamine rubber aging inhibitor, dyestuff, developer and oil dope, chemical reagent, anesthesia are also acted as
Agent etc..
The content of the invention
Mainly iron powder reducing method and Lei Ni are used in method present invention aim to address current reduction p-nitrophenol
Nickel catalytic hydrogenation method is high there are iron powder reducing method production cost, seriously polluted, and raney ni catalysis hydrogenation method is not square there is also use
Just, accessory substance growing amount is big, and catalyst consumption is big, what the technical problem for having the shortcomings that security risk proposed.
To realize above goal of the invention, a kind of h-BN to load Au or Pd of present invention offer is catalyst reduction to nitro
The method of phenol, includes the following steps：
(1) prepare certain volume than ethylene glycol:Aqueous solution, is put into h-BN powder, and ultrasound makes it be uniformly dispersed, and adds 2 wt%
Sodium citrate, ultrasound makes its dissolving；
(2) H is added2PdCl4Solution or HAuCl4Solution, concussion 2 h of absorption, pH to 9-11, centrifugation are adjusted with NaOH aqueous solutions
Taking precipitate with deionized water centrifuge washing three times, then with ethanol centrifuge washing three times；
(3) clear liquid is abandoned, adds NaBH4Aqueous solution, stands 0.5 h of reaction, and centrifugation taking precipitate spends ionized water centrifuge washing three
It is secondary, then, take deposit to obtain catalyst in oven for drying with ethanol centrifuge washing three times；
(4) by water, p-nitrophenol, NaBH4Aqueous solution mixes, and stirs evenly, and adds catalyst and carries out reduction reaction, is used in combination
UV-Vis carries out in-situ tracking.
Further, step（1）Described in ethylene glycol：The 1-3 that the volume ratio of aqueous solution is:1.
Further, step（1）Described in catalyst the load capacity of sodium citrate be 1 wt%-5 wt%.
Further, step（2）Described in catalyst, carried metal is Pd or Au, its load capacity is 0.5 %-5 %.
Further, step（3）Described in catalyst, NaBH4Amount as reducing agent is 0.05M-0.2M.
Compared with prior art, the beneficial effects of the invention are as follows：
（1）The present invention is participated in without hydrogen, and no security risk, catalyst preparation and catalytic condition are gentle.
（2）The present invention is easy to operate, and whole technological process is shorter.
（3）Catalyst performance is excellent, and yield is high, and pollution is small, is swift in response.
Brief description of the drawings
Fig. 1 is the SEM figures of Au/h-BN catalyst in embodiment 5 of the present invention；
Fig. 2 is the ultraviolet-visible spectrogram of Pd/h-BN catalyst reduction p-nitrophenols in embodiment 2 of the present invention；
Fig. 3 is the ultraviolet-visible spectrogram of Au/h-BN catalyst reduction p-nitrophenols in embodiment 5 of the present invention；
Fig. 4 is the XRD diagram of 0.5 wt% Pd/h-BN in the embodiment of the present invention 2；
Fig. 5 is the XRD diagram of 0.5 wt% Au/h-BN in the embodiment of the present invention 5.
Embodiment
The invention will be further described with specific embodiment below in conjunction with the accompanying drawings.
Embodiment 1：Dose volume ratio is 1:1 ethylene glycol:10 mL of aqueous solution, is put into 200 mg h-BN（Six sides nitrogenize
Boron）Powder, ultrasound make to be uniformly dispersed, and add the sodium citrate of 4 mg, and ultrasound makes it scattered.Add 470 mL, 20 mM
H2PdCl4Solution, 2 h of concussion absorption.PH to 9-11 is adjusted with 0.4 mg/mL NaOH aqueous solutions.10 are centrifuged with 4000 rpm
Min, taking precipitate with deionized water centrifuge washing three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000
Rpm, 10 min）.Clear liquid is abandoned, adds the NaBH of 3 mL, 0.378 mg/mL4Aqueous solution, stands 0.5 h of reaction.With 4000 rpm
Centrifuge 10 min, taking precipitate with deionized water centrifuge washing three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three
It is secondary（4000 rpm, 10 min）.Deposit is taken to obtain catalyst in oven for drying.In a clean cuvette, add 2.5 mL water,
200 mL, 1 mM p-nitrophenols, 200 mL, 0.1 M NaBH4Aqueous solution, stirs evenly, and carries out uv scan, adds
Enter 2 mg drying rear catalysts and carry out reduction reaction, with UV-Vis tracking reaction process, i.e., every 2 min carries out once ultraviolet sweep
Retouch.
Embodiment 2：Dose volume ratio is 1:1 ethylene glycol:10 mL of aqueous solution, is put into 200 mg h-BN powder, ultrasound
Make to be uniformly dispersed, add the sodium citrate of 4 mg, ultrasound makes it scattered.Add 470 mL, 20 mM H2PdCl4Solution, concussion are inhaled
Attached 2 h.PH to 9-11 is adjusted with 0.4 mg/mL NaOH aqueous solutions.With 4000 rpm centrifuge 10 min, taking precipitate spend from
Sub- water centrifuge washing is three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000 rpm, 10 min）.Abandon clear
Liquid, adds the NaBH of 3 mL, 0.378 mg/mL4Aqueous solution, stands 0.5 h of reaction.10 min are centrifuged with 4000 rpm, it is heavy to take
Starch with deionized water centrifuge washing three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000 rpm, 10
min）.Deposit is taken to obtain catalyst in oven for drying.In a clean cuvette, add 2.5 mL water, 200 mL, 1 mM to nitre
Base phenol, 200 mL, 0.1 M NaBH4Aqueous solution, stirs evenly, and carries out uv scan, adds 4mg drying rear catalysts
Reduction reaction is carried out, with UV-Vis tracking reaction process, i.e., every 2 min carries out a UV scanning.
Fig. 2 is the ultraviolet-visible spectrogram of Pd/h-BN catalyst reduction p-nitrophenols in this embodiment；Fig. 4 is this
The XRD diagram of 0.5 wt% Pd/h-BN in embodiment.
Embodiment 3：Dose volume ratio is 1:1 ethylene glycol:10 mL of aqueous solution, is put into 200 mg h-BN powder, ultrasound
Make to be uniformly dispersed, add the sodium citrate of 4 mg, ultrasound makes it scattered.Add 470 mL, 20 mM H2PdCl4Solution, concussion are inhaled
Attached 2 h.PH to 9-11 is adjusted with 0.4 mg/mL NaOH aqueous solutions.With 4000 rpm centrifuge 10 min, taking precipitate spend from
Sub- water centrifuge washing is three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000 rpm, 10 min）.Abandon clear
Liquid, adds the NaBH of 3 mL, 0.378 mg/mL4Aqueous solution, stands 0.5 h of reaction.10 min are centrifuged with 4000 rpm, it is heavy to take
Starch with deionized water centrifuge washing three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000 rpm, 10
min）.Deposit is taken to obtain catalyst in oven for drying.In a clean cuvette, add 2.5 mL water, 200 mL, 1 mM to nitre
Base phenol, 200 mL, 0.1 M NaBH4Aqueous solution, stirs evenly, and carries out uv scan, is catalyzed after adding 6 mg dryings
Agent carries out reduction reaction, and with UV-Vis tracking reaction process, i.e., every 2 min carries out a UV scanning.
Embodiment 4：Dose volume ratio is 1:1 ethylene glycol:10 mL of aqueous solution, is put into 200 mg h-BN powder, ultrasound
Make to be uniformly dispersed, add the sodium citrate of 4 mg, ultrasound makes it scattered.Add 101.5 mL, 17 mg/mL HAuCl4Solution,
2 h of concussion absorption.PH to 9-11 is adjusted with 0.4mg/mL NaOH aqueous solutions.10 min are centrifuged with 4000 rpm, taking precipitate is used
Deionized water centrifuge washing is three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000 rpm, 10 min）.
Clear liquid is abandoned, adds the NaBH of 3 mL, 0.378 mg/mL4Aqueous solution, stands 0.5 h of reaction.10 min are centrifuged with 4000 rpm,
Taking precipitate with deionized water centrifuge washing three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000
Rpm, 10 min）.Deposit is taken to obtain catalyst in oven for drying.In a clean cuvette, add 2.5 mL water, 200 mL 1
MM p-nitrophenols, 200 mL, 0.1 M NaBH4Aqueous solution, stirs evenly, and carries out uv scan, adds 2 mg dryings
Rear catalyst carries out reduction reaction, and with UV-Vis tracking reaction process, i.e., every 2 min carries out a UV scanning.
Embodiment 5：Dose volume ratio is 1:1 ethylene glycol:10 mL of aqueous solution, is put into 200 mg h-BN powder, ultrasound
Make to be uniformly dispersed, add the sodium citrate of 4 mg, ultrasound makes it scattered.Add 101.5 mL, 17 mg/mL HAuCl4Solution,
2 h of concussion absorption.PH to 9-11 is adjusted with 0.4 mg/mL NaOH aqueous solutions.10 min, taking precipitate are centrifuged with 4000 rpm
With deionized water centrifuge washing three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000 rpm, 10
min）.Clear liquid is abandoned, adds the NaBH of 3 mL, 0.378 mg/mL4Aqueous solution, stands 0.5 h of reaction.10 are centrifuged with 4000 rpm
Min, taking precipitate with deionized water centrifuge washing three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000
Rpm, 10 min）.Deposit is taken to obtain catalyst in oven for drying.In a clean cuvette, add 2.5 mL water, 200 mL 1
MM p-nitrophenols, 200 mL, 0.1 M NaBH4Aqueous solution, stirs evenly, and carries out uv scan, adds 4 mg dryings
Rear catalyst carries out reduction reaction, and with UV-Vis tracking reaction process, i.e., every 2 min carries out a UV scanning.
Fig. 1 is the SEM figures of Au/h-BN catalyst in this embodiment；Fig. 3 is Au/h-BN catalyst in this embodiment
Reduce the ultraviolet-visible spectrogram of p-nitrophenol；Fig. 5 is the XRD diagram of 0.5 wt% Au/h-BN in the present embodiment.
Embodiment 6：Dose volume ratio is 1:1 ethylene glycol:10 mL of aqueous solution, is put into 200 mg h-BN powder, ultrasound
Make to be uniformly dispersed, add the sodium citrate of 4 mg, ultrasound makes it scattered.Add 101.5 mL, 17 mg/mL HAuCl4Solution,
2 h of concussion absorption.PH to 9-11 is adjusted with 0.4 mg/mL NaOH aqueous solutions.10 min, taking precipitate are centrifuged with 4000 rpm
With deionized water centrifuge washing three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000 rpm, 10
min）.Clear liquid is abandoned, adds the NaBH of 3 mL, 0.378 mg/mL4Aqueous solution, stands 0.5 h of reaction.10 are centrifuged with 4000 rpm
Min, taking precipitate with deionized water centrifuge washing three times（4000 rpm, 10 min）, then with ethanol centrifuge washing three times（4000
Rpm, 10 min）.Deposit is taken to obtain catalyst in oven for drying.In a clean cuvette, add 2.5 mL water, 200 mL 1
MM p-nitrophenols, 200 mL, 0.1 M NaBH4Aqueous solution, stirs evenly, and carries out uv scan, adds 6 mg dryings
Rear catalyst carries out reduction reaction, and with UV-Vis tracking reaction process, i.e., every 2 min carries out a UV scanning.
It is complete by above-mentioned description, relevant staff using the above-mentioned desirable embodiment according to the present invention as enlightenment
Various changes and amendments can be carried out without departing from the scope of the technological thought of the present invention' entirely.The technology of this invention
Property scope is not limited to the content on specification, it is necessary to determines its technical scope according to right.
Claims (5)
1. in methods of the h-BN as catalyst reduction p-nitrophenol for loading Au or Pd, it is characterised in that include the following steps：
(1) prepare certain volume than ethylene glycol:Aqueous solution, is put into h-BN powder, and ultrasound makes it be uniformly dispersed, and adds 2 wt%
Sodium citrate, ultrasound makes its dissolving；
(2) H is added2PdCl4Solution or HAuCl4Solution, concussion 2 h of absorption, pH to 9-11, centrifugation are adjusted with NaOH aqueous solutions
Taking precipitate with deionized water centrifuge washing three times, then with ethanol centrifuge washing three times；
(3) clear liquid is abandoned, adds NaBH4Aqueous solution, stands 0.5 h of reaction, and centrifugation taking precipitate spends ionized water centrifuge washing three
It is secondary, then, take deposit to obtain catalyst in oven for drying with ethanol centrifuge washing three times；
(4) by water, p-nitrophenol, NaBH4Aqueous solution mixes, and stirs evenly, and adds catalyst and carries out reduction reaction, and uses UV-
Vis carries out in-situ tracking.
2. as claimed in claim 1 to load methods of the h-BN as catalyst reduction p-nitrophenol of Au or Pd, its feature
It is, step（1）Described in ethylene glycol：The 1-3 that the volume ratio of aqueous solution is:1.
3. as claimed in claim 1 to load methods of the h-BN as catalyst reduction p-nitrophenol of Au or Pd, its feature
It is, step（1）Described in catalyst the load capacity of sodium citrate be 1 wt%-5 wt%.
4. as claimed in claim 1 to load methods of the h-BN as catalyst reduction p-nitrophenol of Au or Pd, its feature
It is, step（2）Described in catalyst, carried metal is Pd or Au, its load capacity is 0.5 %-5 %.
5. as claimed in claim 1 to load methods of the h-BN as catalyst reduction p-nitrophenol of Au or Pd, its feature
It is, step（3）Described in catalyst, NaBH4Amount as reducing agent is 0.05M-0.2M.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109225326A (en) * | 2018-09-14 | 2019-01-18 | 浙江大学台州研究院 | The preparation method of composite catalyst based on polypyrrole and Carbon foam load gold nano line |
| CN113713839A (en) * | 2020-05-25 | 2021-11-30 | 中国科学院大连化学物理研究所 | Boron nitride loaded metal ruthenium catalyst, preparation method and application in imine preparation |
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| CN103111245A (en) * | 2013-03-20 | 2013-05-22 | 福州大学 | Method for preparing silver-nanoparticle-loaded multilayer graphite-phase boron nitride colloid |
| CN106881141A (en) * | 2017-04-19 | 2017-06-23 | 福州大学 | Cobalt/hexagonal boron nitride complex nucleus shell structural nano catalyst and its preparation and application |
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| CN103111245A (en) * | 2013-03-20 | 2013-05-22 | 福州大学 | Method for preparing silver-nanoparticle-loaded multilayer graphite-phase boron nitride colloid |
| CN106881141A (en) * | 2017-04-19 | 2017-06-23 | 福州大学 | Cobalt/hexagonal boron nitride complex nucleus shell structural nano catalyst and its preparation and application |
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| HENG SHEN ET AL.: "Facile in situ synthesis of silver nanoparticles on boron nitride nanosheets with enhanced catalytic performance", 《J. MATER. CHEM. A》 * |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109225326A (en) * | 2018-09-14 | 2019-01-18 | 浙江大学台州研究院 | The preparation method of composite catalyst based on polypyrrole and Carbon foam load gold nano line |
| CN113713839A (en) * | 2020-05-25 | 2021-11-30 | 中国科学院大连化学物理研究所 | Boron nitride loaded metal ruthenium catalyst, preparation method and application in imine preparation |
| CN113713839B (en) * | 2020-05-25 | 2023-04-07 | 中国科学院大连化学物理研究所 | Boron nitride loaded metal ruthenium catalyst, preparation method and application in imine preparation |
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