CN108658714A - A kind of preparation method of aromatic amine compounds - Google Patents
A kind of preparation method of aromatic amine compounds Download PDFInfo
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- CN108658714A CN108658714A CN201810415587.0A CN201810415587A CN108658714A CN 108658714 A CN108658714 A CN 108658714A CN 201810415587 A CN201810415587 A CN 201810415587A CN 108658714 A CN108658714 A CN 108658714A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/04—Formation or introduction of functional groups containing nitrogen of amino groups
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/06—Formation or introduction of functional groups containing nitrogen of amide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/325—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups reduction by other means than indicated in C07C209/34 or C07C209/36
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Abstract
The invention discloses a kind of preparation methods of aromatic amine compounds, a certain amount of support type cobalt-containing catalyst and a certain amount of fragrant nitro compound are added in reactor in the method, then ammonium formate is added, with tetrahydrofuran and water mixed solvent, under stirring, reaction temperature is 80~200 DEG C, reaction 0.5~for 24 hours, and obtain corresponding aromatic amine compounds.Preparation in accordance with the present invention is environmentally protective using cheap, reproducible bamboo shoots as the raw material for preparing carbon matrix precursor, simple and easy to get, need not additionally add nitrogen source material；It is cheap simultaneously using triphenylphosphine as phosphorus source.Replace hydrogen as reducing agent using ammonium formate, easy to operate, reaction condition is mild, more easy to control especially for chemo-selective for the fragrant nitro compound containing easy reduction functional group.
Description
Technical field
The invention belongs to field of fine chemical, more particularly to a kind of including aniline, N- phenyl formamides
The preparation method of aromatic amine compounds.
Background technology
Aniline is the very extensive organic chemical industry's intermediate of purposes, be widely used in fuel, medicine, pigment, rubber chemicals,
The production of pesticide and fine-chemical intermediate.Especially as the raw materials for production of MDI, there is prodigious market potential.N- phenyl
Important derivatives one of of the formamide as aniline, also in medicine, pesticide, natural industry and polymer and protein, polypeptide
Equal fields play an important role.Currently, most aniline are the effects by fragrant nitro compound in noble metal catalyst
Lower direct hydrogenation reduction is made, and N- phenyl formamides are then the products of aniline and the further formylation reaction of carbon source.The synthesis side
Method path is simple, meets Atom economy requirement, but reaction is related to hydrogen, and reaction condition is harsher, needs high temperature height
Pressure, and it is more demanding to consersion unit, energy consumption is higher.In addition, the chemo-selective of hydrogenation reaction is also poor, especially for
Fragrant nitro compound containing easy reduction functional group.Therefore, new synthesis aniline and its derivatives method is developed still with good
Good Commercial Prospect.
Invention content
The problems in for the above-mentioned prior art, according to an aspect of the present invention, it is an object of the present invention to carry
For a kind of preparation method of the aromatic amine compounds including aniline, N- phenyl formamides, the method carries out as follows：
A certain amount of support type cobalt-containing catalyst and a certain amount of fragrant nitro compound are added in reactor, are then added
Ammonium formate and tetrahydrofuran and water mixed solvent, under stirring, reaction temperature is 80~200 DEG C, reaction 0.5~for 24 hours, and obtain phase
The aromatic amine compounds answered.
Preferably, the fragrant nitro compound is selected from
Preferably, the quality of the support type cobalt-containing catalyst and the molar ratio of fragrant nitro compound are 40mg:1mmol is extremely
120mg:1mmol, preferably 80mg:1mmol.
Preferably, the fragrant nitro compound and ammonium formate molar ratio 1:1 to 1:20, preferably 1:2 to 1:15, more preferably
It is 1:4 to 1:10.
Preferably, the solvent is tetrahydrofuran and water mixed solvent, and the volume ratio of tetrahydrofuran and water is 20:1 to 1:
1, preferably 15:1 to 5:1, more preferably 9:1.
Preferably, the molar ratio of the total volume of the mixed solvent and fragrant nitro compound is 20ml:1mmol to 3ml:
1mmol, preferably 15ml:1mmol to 7ml:1mmol, more preferably 10ml:1mmol.
Preferably, using the nano particle of cobalt or its oxide as active component in the support type cobalt-containing catalyst, with life
The porous carbon materials of object base nitrogen and phosphorus doping are the composition of carrier, and wherein activated centre cobalt nano-particle is by carrier porous carbon packet
It wraps up in.
Preferably, the support type cobalt-containing catalyst by 0.1wt%~10wt% cobalt active component and 90wt%~
The biology base nitrogen of 99.9wt% and the porous carbon materials carrier of phosphorus doping are constituted, the cobalt active component of preferably 1wt%~5wt%
With the carrier porous carbon of 90wt%~95wt%, the cobalt active component and 95wt%~98wt% of more preferably 2wt%~5wt%
Carrier porous carbon, and the specific surface area of the porous carbon materials carrier be 100~1000m2/ g, nitrogen content are 1~20wt%,
Phosphorus content is 0.1~20wt%.
Preferably, the specific surface area of the porous carbon materials carrier is 200~1000m2/ g, nitrogen content are 1~10wt%,
Phosphorus content is 0.1~10wt%.
Preferably, support type cobalt-containing catalyst according to the present invention is prepared as follows method and is prepared：
(1) using bamboo shoots as raw material, first bamboo shoots are sliced, the grind into powder after washing, drying, bamboo shoots powder is taken to be added
It in deionized water, moves on in the hydrothermal reaction kettle of polytetrafluoroethyllining lining, is reacted 6 hours in 180 DEG C, mistake after being uniformly mixed
Filter, washing, it is dry after to get to the porous carbon materials support precursor of the N doping of brown solid；
(2) it takes cobalt salt to be dissolved in deionized water, triphenylphosphine is added, ultrasonic dissolution adds the biology base N doping
Porous carbon materials support precursor, after stirring evenly, by drying, grinding, formed particle；
(3) particle obtained in step (2) is placed in tube furnace 800 DEG C of calcining 2h in inert atmosphere, drops to room temperature
After take out to get to nitrogen, phosphorus doping carbon Encapsulation nanoparticle Co catalysts.
Preferably, cobalt salt described in step (2) is selected from nitric hydrate cobalt, cobalt chloride, cobalt carbonate, cobaltous sulfate, preferably water
Close cobalt nitrate.
Advantageous effect
The present invention has following advantage compared with prior art：
1, using cheap, reproducible bamboo shoots as the raw material for preparing carbon matrix precursor, feed distribution is extensive, environmentally protective,
It is simple and easy to get, and due to nitrogenous compound (such as protein, amino acid etc.) of the bamboo shoots containing 8wt% itself, it need not be additional
Add nitrogen source material；It is cheap simultaneously using triphenylphosphine as phosphorus source.
2, nitrogen of the present invention, phosphorus doping carbon Encapsulation nanoparticle Co catalysts are as base metal heterogeneous catalyst,
Common noble metal catalyst is restored with fragrant nitro compound to compare, cheap, rich reserves, chemism are stable and easy
Separation and recycling.
3, nitrogen of the present invention, phosphorus doping carbon Encapsulation nanoparticle Co catalysts are in fragrant nitro compound reduction reaction
Show excellent catalytic activity and stability.On the one hand the doping of nitrogen, phosphorus can be effectively increased the active sites of catalyst surface
Point；On the other hand it can enhance the interaction of cobalt nano-particle and carbon carrier, point of the raising cobalt nano-particle in carrier surface
Divergence effectively inhibits the loss of cobalt active component during the reaction so that the catalyst is recycling six times later still
It can keep the conversion ratio of 90% or more nitrobenzene.In addition, the nitrogen, phosphorus doping carbon Encapsulation nanoparticle Co catalysts are to fragrant nitro
The wide application range of substrates of compound is general, and no matter substrate is powered subbase group substitution or is substituted with electron withdrawing groups, substrate
It can convert completely, and obtain the yield of 90% or more target product.
4, the reaction use ammonium formate replace hydrogen as reducing agent, easy to operate, reaction condition is mild, especially for containing
There is chemo-selective for the fragrant nitro compound of easily reduction functional group more easy to control.
5, in the reaction, ammonium formate can also be used as the carbon source that the further formylation reaction of aniline generates benzamide；Wherein,
The dosage of ammonium formate is the important indicator of modulation selectivity of product.
Description of the drawings
Fig. 1 is the catalysis of the nitrogen, phosphorus doping porous carbon support Encapsulation nanoparticle cobalt active constituent that are prepared according to embodiment 1
The high-resolution-ration transmission electric-lens figure of agent.
Fig. 2 is the catalysis of the nitrogen, phosphorus doping porous carbon support Encapsulation nanoparticle cobalt active constituent that are prepared according to embodiment 1
The XPS datagrams of agent.
Fig. 3 is the catalysis of the nitrogen, phosphorus doping porous carbon support Encapsulation nanoparticle cobalt active constituent that are prepared according to embodiment 1
The XRD datagrams of agent.
Specific implementation mode
Hereinafter, will be described in detail the present invention.Following embodiment is enumerated only as the example of embodiment of the present invention,
It does not limit the present invention in any way, it will be appreciated by those skilled in the art that in the model of essence and design without departing from the present invention
Modification in enclosing each falls within protection scope of the present invention.Unless stated otherwise, the reagent and instrument used in following embodiment is equal
For commercially available product.
Material characterization instrument：
Transmission electron microscope：Model H-7650, manufacturer are Hitachi Hitachi, Ltds of Japan
XPS：Model ESCALAB 250Xi, manufacturer are Thermo Scientific companies of Britain
Physical adsorption appearance：Model ASAP2020, manufacturer are micrometritics companies of the U.S.
ICP-AES：Model 5300DV, manufacturer are PerkinElmer Optima companies of the U.S.
XRD：Model D8Advance, manufacturer are Bruker companies of Germany
Embodiment 1：The preparation of nitrogen, phosphorus doping porous carbon Encapsulation nanoparticle Co catalysts
(1) using bamboo shoots as raw material, first bamboo shoots are sliced, at 70 DEG C, drying for 24 hours, obtains solid, grind into powder.Take 2g powder
End is added in 20mL deionized waters, is moved on to after being uniformly mixed in the hydrothermal reaction kettle of polytetrafluoroethyllining lining, anti-in 180 DEG C
It answers 6 hours, is filtered, washed, 70 DEG C of dryings obtain brown solid afterwards for 24 hours.
(2) 0.4mmol Co (NO are taken3)2·6H2O is dissolved in 30mL deionized waters, and 0.2g triphenylphosphines, ultrasound is added
30min adds the brown solid of the above-mentioned preparations of 1g, and after 60 DEG C are stirred 2h, 100 DEG C of dry 10h, grinding is placed in tube furnace
800 DEG C of calcining 2h in nitrogen gas atmosphere, sample is taken out be catalyzed containing cobalt to get to support type after tube furnace drops to room temperature
Agent.The load capacity that cobalt in the nitrogen, phosphorus doping carbon Encapsulation nanoparticle Co catalysts is measured by ICP is 3.54wt%；Pass through XPS
It is 2.74wt%, phosphorus element content 0.52wt% to measure nitrogen element content in the catalyst；Pass through N2Adsorption-desorption method measures
The specific surface area of the catalyst is 400m2g-1。
Fig. 1 is to transmit electricity according to the high-resolution of nitrogen manufactured in the present embodiment, phosphorus doping carbon Encapsulation nanoparticle Co catalysts
Mirror figure.As shown in Figure 1, cobalt nano-particle is wrapped up by carbon in the material, and it is dispersed in carbon material surface, cobalt nano-particle
Size is about 23nm.
Fig. 2 is to be urged according to nitrogen manufactured in the present embodiment, phosphorus doping porous carbon support Encapsulation nanoparticle cobalt active constituent
The XPS datagrams of agent.Can be seen that N from the data of XPS, the doping of P can promote cobalt phosphorus, the coordination of cobalt nitrogen, formed Co-N and
Co-P species increase the cloud density of cobalt, to be conducive to reactant nitrobenzene and ammonium formate on cobalt active component surface
Absorption promotes the progress of reaction.
Fig. 3 is to be urged according to nitrogen manufactured in the present embodiment, phosphorus doping porous carbon support Encapsulation nanoparticle cobalt active constituent
The XRD datagrams of agent.
Embodiment 2：Application load type cobalt-containing catalyst synthesizes aniline method
The support type prepared in 40mg embodiments 1 is added in the heavy-walled glass reaction tube with magnetic stir bar at one to contain
It is molten to add 0.5mmol nitrobenzenes, 2mmol ammonium formates and tetrahydrofuran/water (4.5/0.5, v/v, mL) mixing for Co catalysts
Agent, stirring, 120 DEG C of reaction 12h after being cooled to room temperature, are analyzed with gas chromatographic detection.The result shows that the conversion ratio of nitrobenzene is
100%, the selectivity of product aniline is 97%.
It is identical as aforesaid operations step, change the type of fragrant nitro compound (i.e. substrate), in support type cobalt-containing catalyst
Under the action of obtain corresponding anil.The selectivity of specific substrate conversion efficiency and anil is as shown in table 1：
Table 1
Comparative example 1 to 6：The influence of different solvents
According to 2 identical operating procedure of embodiment, using different solvents under the action of support type cobalt-containing catalyst by
Nitrobenzene aniline, the results are shown in Table 2：
Table 2
As can be seen from Table 2 only when using tetrahydrofuran and water for mixed solvent, conversion ratio and selectivity are all
It is very excellent, and other solvents are used, such as when the organic solvent of DMSO, DMF as in the mixed solvent, conversion ratio is simultaneously paid no attention to
Think.And when using single solvent tetrahydrofuran or water, then conversion ratio and selectivity are also undesirable.
Comparative example 7 to 10：The influence of different ammonium formate dosages
According to 2 identical operating procedure of embodiment, using different proportion ammonium formate support type cobalt-containing catalyst work
By nitrobenzene aniline, the results are shown in Table 3 under：
Table 3
Number 4 to 1 in table 3 in one column of ammonium formate is respectively that the mole of ammonium formate is 4 times to 1 of reactant nitrobenzene
Times.It can be seen from table 3 to data when the mole of ammonium formate is 4 times of nitrobenzene, reaction effect is best, and works as formic acid
When the mole of ammonium is less than 4 times of nitrobenzene, conversion ratio is too low, valueless.
Comparative example 11 to 14：The influence of different catalysts
According to 2 identical operating procedure of embodiment, using different catalysts by nitrobenzene aniline result such as 4 institute of table
Show：
Table 4
Catalyst " Co@NCP " indicates that the Carriers Active carbon for preparing in embodiment 1 is be doped with N, P porous carbon supported in table 4
Cobalt-containing catalyst prepared by body, " Co NC " are represented without phosphorus doping, and " Co C " representative is both without phosphorus or without N doping, only activated carbon
Do carrier.After being doped with N, P element in the carrier that can be seen that catalyst in 4 data of table, the conversion ratio and selectivity of reaction
It is very excellent, and in the case of undoping, conversion ratio is not ideal enough.
Embodiment 11：Application load type cobalt-containing catalyst synthesizes N- phenyl formamide methods
The support type prepared in 40mg embodiments 1 is added in the heavy-walled glass reaction tube with magnetic stir bar at one to contain
Co catalysts add 0.5mmol nitrobenzenes, 5mmol ammonium formates and tetrahydrofuran solvent, stirring, 120 DEG C of reaction 12h, cooling
To room temperature, analyzed with gas chromatographic detection.The result shows that the conversion ratio of nitrobenzene is 100%, product N- phenyl formamides
Selectivity is 95%.
It is identical with aforesaid operations step, change the type of fragrant nitro compound (i.e. substrate), in support type cobalt-containing catalyst
Under the action of obtain corresponding N- aryl carboxamides.The selectivity of specific substrate conversion efficiency and N- aryl carboxamides is as shown in table 5：
Table 5
Comparative example 11 to 14：The influence of different catalysts
According to 11 identical operating procedure of embodiment, using different catalysts by nitrobenzene N- aryl carboxamides results
As shown in table 6.There it can be seen that after being doped with N, P element in the carrier of catalyst, the reaction of nitrobenzene N- aryl carboxamides
Conversion ratio and selectivity it is very excellent, and in the case of undoping, conversion ratio is not ideal enough.
Table 6
Claims (10)
1. a kind of preparation method of aromatic amine compounds, the method carry out as follows：
A certain amount of support type cobalt-containing catalyst and a certain amount of fragrant nitro compound are added in reactor, formic acid is then added
Ammonium and tetrahydrofuran and water mixed solvent, under stirring, reaction temperature is 80~200 DEG C, reaction 0.5~for 24 hours, and it obtains corresponding
Aromatic amine compounds.
2. the preparation method of aromatic amine compounds according to claim 1, which is characterized in that the virtue nitro compound choosing
From
3. the preparation method of aromatic amine compounds according to claim 1, which is characterized in that the support type is catalyzed containing cobalt
The quality of agent and the molar ratio of fragrant nitro compound are 40mg:1mmol to 120mg:1mmol, preferably 80mg:1mmol.
4. the preparation method of aromatic amine compounds according to claim 1, which is characterized in that it is described virtue nitro compound with
Ammonium formate molar ratio 1:1 to 1:20, preferably 1:2 to 1:15, more preferably 1:4 to 1:10.
5. the preparation method of aromatic amine compounds according to claim 1, which is characterized in that the solvent is tetrahydrofuran
With water mixed solvent, the volume ratio of tetrahydrofuran and water is 20:1 to 1:1, preferably 15:1 to 5:1, more preferably 9:1.
6. the preparation method of aromatic amine compounds according to claim 1, which is characterized in that the totality of the mixed solvent
Product and the molar ratio of fragrant nitro compound are 20ml:1mmol to 3ml:1mmol, preferably 15ml:1mmol to 7ml:1mmol,
More preferably 10ml:1mmol.
7. the preparation method of aromatic amine compounds according to claim 1, which is characterized in that the support type is catalyzed containing cobalt
Using the nano particle of cobalt or its oxide as active component in agent, using the porous carbon materials of biology base nitrogen and phosphorus doping as carrier
It constitutes, wherein activated centre cobalt nano-particle is wrapped up by carrier porous carbon.
8. the preparation method of aromatic amine compounds according to claim 1, which is characterized in that the support type is catalyzed containing cobalt
Agent by 0.1wt%~10wt% cobalt active component and the biology base nitrogen of 90wt%~99.9wt% and the porous carbon of phosphorus doping
Expect that carrier is constituted, the cobalt active component of preferably 1wt%~5wt% and the carrier porous carbon of 90wt%~95wt%, more preferably
For the cobalt active component of 2wt%~5wt% and the carrier porous carbon of 95wt%~98wt%, and the porous carbon materials carrier
Specific surface area is 100~1000m2/ g, nitrogen content are 1~20wt%, and phosphorus content is 0.1~20wt%；Preferably, described porous
The specific surface area of carbon material carrier is 200~1000m2/ g, nitrogen content are 1~10wt%, and phosphorus content is 0.1~10wt%.
9. the preparation method of aromatic amine compounds according to claim 1, which is characterized in that the support type is catalyzed containing cobalt
Agent is prepared as follows method and is prepared：
(1) using bamboo shoots as raw material, first bamboo shoots are sliced, the grind into powder after washing, drying, take bamboo shoots powder addition go from
It in sub- water, moves on to after being uniformly mixed in the hydrothermal reaction kettle of polytetrafluoroethyllining lining, is reacted 6 hours in 180 DEG C, filtering,
Washing, it is dry after to get to the porous carbon materials support precursor of the N doping of brown solid；
(2) it takes cobalt salt to be dissolved in deionized water, triphenylphosphine is added, ultrasonic dissolution adds the life prepared in step (1)
The porous carbon materials support precursor of object base N doping after stirring evenly, by drying, grinding, forms particle；
(3) particle obtained in step (2) is placed in tube furnace 800 DEG C of calcining 2h in inert atmosphere, is taken after dropping to room temperature
Go out to get to nitrogen, phosphorus doping carbon Encapsulation nanoparticle Co catalysts.
10. the preparation method of aromatic amine compounds according to claim 9, which is characterized in that cobalt salt described in step (2)
Selected from nitric hydrate cobalt, cobalt chloride, cobalt carbonate, cobaltous sulfate, preferably nitric hydrate cobalt.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111138309A (en) * | 2020-01-21 | 2020-05-12 | 浙江工业大学 | Catalytic hydrogenation reduction method for aromatic nitro compound |
| CN114950404A (en) * | 2022-05-19 | 2022-08-30 | 中国科学院兰州化学物理研究所 | Wear-resistant ammonia oxidation catalyst and preparation method and application thereof |
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| CN103539596A (en) * | 2013-10-25 | 2014-01-29 | 上海交通大学 | Method for catalyzing transfer of hydrogen controllable reduction nitro-compound in formic acid or formate |
| CN104174421A (en) * | 2014-08-08 | 2014-12-03 | 浙江大学 | Heterogeneous catalyst for selective hydrogenation reaction of aryl nitro-compound and application of heterogeneous catalyst |
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| CN103539596A (en) * | 2013-10-25 | 2014-01-29 | 上海交通大学 | Method for catalyzing transfer of hydrogen controllable reduction nitro-compound in formic acid or formate |
| CN104174421A (en) * | 2014-08-08 | 2014-12-03 | 浙江大学 | Heterogeneous catalyst for selective hydrogenation reaction of aryl nitro-compound and application of heterogeneous catalyst |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111138309A (en) * | 2020-01-21 | 2020-05-12 | 浙江工业大学 | Catalytic hydrogenation reduction method for aromatic nitro compound |
| CN111138309B (en) * | 2020-01-21 | 2023-05-16 | 浙江工业大学 | Catalytic hydrogenation reduction method for aromatic nitro compound |
| CN114950404A (en) * | 2022-05-19 | 2022-08-30 | 中国科学院兰州化学物理研究所 | Wear-resistant ammonia oxidation catalyst and preparation method and application thereof |
| CN114950404B (en) * | 2022-05-19 | 2023-11-17 | 中国科学院兰州化学物理研究所 | Wear-resistant ammonia oxidation catalyst and preparation method and application thereof |
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