CN102964194A - Rh3Ni1 catalyst and method for preparing arylamine by carrying out catalytic reduction on nitro aromatic hydrocarbon through Rh3Ni1 catalyst - Google Patents
Rh3Ni1 catalyst and method for preparing arylamine by carrying out catalytic reduction on nitro aromatic hydrocarbon through Rh3Ni1 catalyst Download PDFInfo
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Abstract
The invention relates to a Rh3Ni1 catalyst and a method for preparing arylamine by carrying out catalytic reduction on nitro aromatic hydrocarbon through the Rh3Ni1 catalyst, and belongs to the technical field of heterogeneous catalysis. The method for preparing the arylamine by carrying out the catalytic reduction on the nitro aromatic hydrocarbon through the Rh3Ni1 catalyst comprises the following steps of putting the nitro aromatic hydrocarbon as a substrate and bimetal Rh3Ni1 as a catalyst in an organic solvent to react in the atmosphere of room-temperature constant-pressure hydrogen to selectively reduce the nitro aromatic hydrocarbon so as to prepare the arylamine, wherein the utilized bimetal Rh3Ni1 is bimetal Rh3Ni1 nano alloy prepared in octadecylamine by taking rhodium chloride trihydrate and nickel acetylacetonate as precursors. The method disclosed by the invention has the advantages that a preparation process of the catalyst is simple, the reaction condition is mild (room temperature and constant pressure), the activity and selectivity of the catalyst are high and the like.
Description
Technical field
The present invention relates to bimetal Rh
3Ni
1Preparation and the catalytic reduction nitro-aromatic method for preparing arylamine thereof, belong to the heterogeneous catalysis technology field.
Background technology
Functionalized aniline is the important intermediate of the chemical such as synthetic drugs, macromolecular material and dyestuff.Current, people mainly prepare aniline by the reduction nitro-aromatic, as use stoichiometric reductive agent, adopt metal complexes catalysis method or the approach such as hydrogen transference hydrogenation or catalytic hydrogenation.Wherein, catalytic hydrogenation has outstanding advantage at aspects such as environment friendly, atom utilizations.Yet, the Industrial Catalysis hydrogenation process carries out under High Temperature High Pressure usually, except energy consumption was higher, for the reduction with the polysubstituted nitro-aromatic of other reducible group (such as halogen, carbonyl, ester group etc.), traditional catalyzer such as the selectivity of commercial Pd/C were relatively poor.For example, take the 4-nitrobenzaldehyde as substrate, carry out hydrogenation reaction take commercial Pd/C as catalyzer, principal product is not the 4-aminobenzaldehyde, but para-totuidine (Scheme1).Thereby, be necessary to develop a kind of catalyzer that can under mild conditions, realize the high selectivity reduction of nitro-aromatic.
Scheme1.Pd/C SCR 4-nitrobenzaldehyde
Studies show that much that recently the single metal nanoparticle of bimetal nano alloy ratio has higher catalytic activity, selectivity and stability, simultaneously, at aspects such as reducing catalyzer cost, simplification catalyst separating a lot of advantages are arranged also.Yet it is still rare at present that the SCR that can carry out at normal temperatures and pressures nitro-aromatic prepares the different-phase catalyst of arylamine.Recently, the people such as Yamamoto has prepared the single Rh of dispersion that loads on the dendrimer
32Fe
28Nanoparticle, and realized at normal temperatures and pressures selective catalytic reduction reaction (Angew.Chem.2011,123, the 5952-5955 of the nitro-aromatics such as oil of mirbane, 4-N-methyl-p-nitroaniline and 4-Nitroanisole; Angew. Chem.Int.Ed.2011,50,5830-5833).Although bimetal Rh
32Fe
28Nanoparticle has represented higher activity than monometallic Rh, yet, in order to stablize bimetal nano particles, need to add baroque dendrimer supports.
In view of this, be necessary to develop a kind of easy single dispersion bimetal nano method for preparing catalyst, and under mild conditions, realize the high selectivity amines preparation by reducing aromatic of nitro-aromatic.
Summary of the invention
The purpose of this invention is to provide a kind of easy single dispersion bimetal nano method for preparing catalyst, and under mild conditions, realize the high selectivity amines preparation by reducing aromatic of a series of nitro-aromatics.
Technical scheme of the present invention is as follows:
A kind of Rh
3Ni
1The catalytic reduction nitro-aromatic prepares the method for arylamine, it is characterized in that the method carries out as follows:
1) take nitro-aromatic as substrate, with bimetal Rh
3Ni
1Be catalyzer, under room temperature normal pressure nitrogen atmosphere, place organic solvent to react substrate, wherein the volumetric molar concentration of substrate is 0.05～0.5mol/L, and the volumetric molar concentration of catalyzer is 0.00015～0.004mol/L;
Described substrate structure formula is as follows,
Wherein R is selected from a kind of in hydrogen, alkyl, halogen, carbonyl, ether, amino, hydroxyl, methylol, ethanoyl and the ester group;
2) hydrogenation reaction 6～24 hours at normal temperatures and pressures, reaction finishes, and centrifugal recovery catalyzer supernatant liquor underpressure distillation desolventizing is obtained target product, or column chromatography for separation obtains target product.
The used organic solvent of the present invention adopts any in methyl alcohol, tetrahydrofuran (THF) and the ethyl acetate.
Rh provided by the invention
3Ni
1Catalyzer is characterized in that this catalyzer prepares as follows:
1) stearylamine is added the thermosetting settled solution as solvent, tensio-active agent and reductive agent;
2) continue to be heated to 120～150 ° of C, then add three rhodium trichloride hydrates and acetylacetonate nickel, wherein the molality of three rhodium trichloride hydrates is 0.015～0.075mmol/g, and the molality of acetylacetonate nickel is 0.005～0.025mmol/g, obtains clarified liq;
3) under the state of high degree of agitation, above-mentioned clarified liq is injected in the stearylamine that is warming up in advance 230～250 ° of C dilutes, the molality of making three rhodium trichloride hydrates is 0.006～0.015mmol/g, and the molality of acetylacetonate nickel is the solution of 0.002～0.005mmol/g;
4) with mentioned solution under 230～250 ° of C aging 1.5～5 minutes, be cooled to and separate out throw out after adding ethanol behind 50 ° of C～80 ° C, centrifugally namely obtain bimetal Rh with washing with alcohol afterwards
3Ni
1, at last with the Rh that obtains
3Ni
1Be dispersed in the hexanaphthene for subsequent use.
Rh described in the present invention
3Ni
1Catalyzer is the mixture of worm-like particles and granular particles, and wherein the grain fineness number of granular particles is 6～10 nanometers.
The present invention compares with the existing single preparation of bimetal nano alloy and method of catalytic reduction nitro-aromatic thereof of disperseing, and the method has that the catalyzer preparation procedure is simple, reaction conditions is gentle (normal temperature and pressure), the catalyst activity and selectivity advantages of higher.
Description of drawings
Fig. 1 is bimetal Rh
3Ni
1The transmission electron microscope picture of catalyzer.
Embodiment
A kind of Rh provided by the invention
3Ni
1The catalytic reduction nitro-aromatic prepares the method for arylamine, and its concrete steps are as follows:
One, at first prepares bimetal Rh
3Ni
1Catalyzer, this catalyzer prepares as follows:
1) stearylamine is added the thermosetting settled solution as solvent, tensio-active agent and reductive agent;
2) continue to be heated to 120～150 ° of C, then add three rhodium trichloride hydrates and acetylacetonate nickel, wherein the molality of three rhodium trichloride hydrates is 0.015～0.075mmol/g, and the molality of acetylacetonate nickel is 0.005～0.025mmol/g, obtains clarified liq;
3) under the state of high degree of agitation, above-mentioned clarified liq is injected in the stearylamine that is warming up in advance 230～250 ° of C dilutes, the molality of making three rhodium trichloride hydrates is 0.006～0.015mmol/g, and the molality of acetylacetonate nickel is the solution of 0.002～0.005mmol/g;
4) with mentioned solution under 230～250 ° of C aging 1.5～5 minutes, be cooled to and separate out throw out after adding ethanol behind 50 ° of C～80 ° C, centrifugally namely obtain bimetal Rh with washing with alcohol afterwards
3Ni
1, at last with the Rh that obtains
3Ni
1Be dispersed in the hexanaphthene for subsequent use.
This bimetal Rh
3Ni
1Catalyzer is the mixture of worm-like particles and granular particles, and wherein the grain fineness number of granular particles is 6～10 nanometers.
Two, the catalytic reduction nitro-aromatic prepares arylamine
1) take nitro-aromatic as substrate, with Rh
3Ni
1Be catalyzer, under room temperature normal pressure nitrogen atmosphere, place organic solvent to react substrate and catalyzer, wherein the volumetric molar concentration of substrate is 0.05～0.5mol/L, and the volumetric molar concentration of catalyzer is 0.00015～0.004mol/L; Used organic solvent generally adopts any in methyl alcohol, tetrahydrofuran (THF) and the ethyl acetate;
Described substrate structure formula is as follows,
Wherein R is selected from a kind of in hydrogen, alkyl, halogen, carbonyl, ether, amino, hydroxyl, methylol, ethanoyl and the ester group;
2) reacted 6～24 hours under the state that stirs, reaction finishes, and centrifugal recovery catalyzer supernatant liquor underpressure distillation desolventizing is obtained target product, or column chromatography for separation obtains target product.
The below enumerates embodiment the present invention is further described, but the invention is not restricted to following embodiment, and under the scope of described aim, change is included in the technical scope of the present invention before and after not breaking away from.
Embodiment one
Implementation method: stearylamine is added the thermosetting settled solution as solvent, tensio-active agent and reductive agent.Continue to be heated to 120 ° of C, then add three rhodium trichloride hydrates and acetylacetonate nickel, wherein the molality of three rhodium trichloride hydrates is 0.015mmol/g, and the molality of acetylacetonate nickel is 0.005mmol/g, obtains clarified liq.Under the state of high degree of agitation, above-mentioned clarified liq is injected in the stearylamine that is warming up in advance 230 ° of C dilutes, the molality of making three rhodium trichloride hydrates is 0.006mmol/g, and the molality of acetylacetonate nickel is the solution of 0.002mmol/g.With mentioned solution under 230 ° of C aging 1.5 minutes, be cooled to and separate out throw out after adding ethanol behind 50 ° of C, centrifugally namely obtain bimetal Rh with washing with alcohol afterwards
3Ni
1, wherein the particle diameter of spherical particle is 6 nanometers, at last with the Rh that obtains
3Ni
1Be dispersed in the hexanaphthene for subsequent use.
Embodiment two
Implementation method: stearylamine is added the thermosetting settled solution as solvent, tensio-active agent and reductive agent.Continue to be heated to 140 ° of C, then add three rhodium trichloride hydrates and acetylacetonate nickel, wherein the molality of three rhodium trichloride hydrates is 0.045mmol/g, and the molality of acetylacetonate nickel is 0.015mmol/g, obtains clarified liq.Under the state of high degree of agitation, above-mentioned clarified liq is injected in the stearylamine that is warming up in advance 240 ° of C dilutes, the molality of making three rhodium trichloride hydrates is 0.012mmol/g, and the molality of acetylacetonate nickel is the solution of 0.004mmol/g.With mentioned solution under 240 ° of C aging 3 minutes, be cooled to and separate out throw out after adding ethanol behind 70 ° of C, centrifugally namely obtain bimetal Rh with washing with alcohol afterwards
3Ni
1, wherein the particle diameter of spherical particle is 8 nanometers, at last with the Rh that obtains
3Ni
1Be dispersed in the hexanaphthene for subsequent use.
Embodiment three
Implementation method: stearylamine is added the thermosetting settled solution as solvent, tensio-active agent and reductive agent.Continue to be heated to 150 ° of C, then add three rhodium trichloride hydrates and acetylacetonate nickel, wherein the molality of three rhodium trichloride hydrates is 0.075mmol/g, and the molality of acetylacetonate nickel is 0.025mmol/g, obtains clarified liq.Under the state of high degree of agitation, above-mentioned clarified liq is injected in the stearylamine that is warming up in advance 250 ° of C dilutes, the molality of making three rhodium trichloride hydrates is 0.015mmol/g, and the molality of acetylacetonate nickel is the solution of 0.005mmol/g.With mentioned solution under 250 ° of C aging 5 minutes, be cooled to and separate out throw out after adding ethanol behind 80 ° of C, centrifugally namely obtain bimetal Rh with washing with alcohol afterwards
3Ni
1, wherein the particle diameter of spherical particle is 10 nanometers, at last with the Rh that obtains
3Ni
1Be dispersed in the hexanaphthene for subsequent use.
Embodiment four
Implementation method: at normal temperatures, with oil of mirbane and Rh
3Ni
1Place ethyl acetate, wherein the volumetric molar concentration of substrate is 0.05mol/L, and the volumetric molar concentration of catalyzer is 0.00015mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 8h at normal temperatures, centrifugal recovery catalyzer, to obtaining aniline after the supernatant liquor underpressure distillation desolventizing, productive rate is 99%.
Embodiment five
Implementation method: at normal temperatures, with 2-nitro-naphthalene and Rh
3Ni
1Place methyl alcohol, wherein the volumetric molar concentration of substrate is 0.15mol/L, and the volumetric molar concentration of catalyzer is 0.0009mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 10h at normal temperatures, centrifugal recovery catalyzer, to obtaining the 2-amino naphthalenes after the supernatant liquor underpressure distillation desolventizing, productive rate is 99%.
Embodiment six
Implementation method: at normal temperatures, with 4-nitrotoluene and Rh
3Ni
1Place methyl alcohol, wherein the volumetric molar concentration of substrate is 0.15mol/L, and the volumetric molar concentration of catalyzer is 0.0008mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 14h at normal temperatures, centrifugal recovery catalyzer, to obtaining the 4-phenylmethylamine after the supernatant liquor underpressure distillation desolventizing, productive rate is 99%.
Embodiment seven
Implementation method: at normal temperatures, with 4-nitrobenzaldehyde and Rh
3Ni
1Place tetrahydrofuran (THF), wherein the volumetric molar concentration of substrate is 0.10mol/L, and the volumetric molar concentration of catalyzer is 0.0015mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 12h at normal temperatures, centrifugal recovery catalyzer, to obtaining the 4-aminobenzaldehyde after the supernatant liquor underpressure distillation desolventizing, productive rate is 99%.
Embodiment eight
Implementation method: at normal temperatures, with 4-N-methyl-p-nitroaniline and Rh
3Ni
1Place methyl alcohol, wherein the volumetric molar concentration of substrate is 0.20mol/L, and the volumetric molar concentration of catalyzer is 0.0015mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 6h at normal temperatures, centrifugal recovery catalyzer, to obtaining pentanoic after the supernatant liquor underpressure distillation desolventizing, productive rate is 99%.
Embodiment nine
Implementation method: at normal temperatures, with the pure and mild Rh of 4-nitrobenzoyl
3Ni
1Place methyl alcohol, wherein the volumetric molar concentration of substrate is 0.13mol/L, and the volumetric molar concentration of catalyzer is 0.0015mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 13h at normal temperatures, centrifugal recovery catalyzer obtains 4-amino-benzene methyl alcohol to crossing the post separation after the supernatant liquor underpressure distillation desolventizing, and productive rate is 95%.
Embodiment ten
Implementation method: at normal temperatures, with 4-nitro-acetophenone and Rh
3Ni
1Place methyl alcohol, wherein the volumetric molar concentration of substrate is 0.5mol/L, and the volumetric molar concentration of catalyzer is 0.004mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture reacted 10h at normal temperatures after, centrifugal recovery catalyzer, to obtaining the 4-aminoacetophenone after the supernatant liquor underpressure distillation desolventizing, productive rate is 98%.
Embodiment 11
Implementation method: at normal temperatures, with 1-chloro-4-oil of mirbane and Rh
3Ni
1Place tetrahydrofuran (THF), wherein the volumetric molar concentration of substrate is 0.05mol/L, and the volumetric molar concentration of catalyzer is 0.0005mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 11h at normal temperatures, centrifugal recovery catalyzer separates and obtains the 4-chloroaniline crossing post after the supernatant liquor underpressure distillation desolventizing, and productive rate is 97%.
Embodiment 12
Implementation method: at normal temperatures, with 2,4, dinitraniline and Rh
3Ni
1Place methyl alcohol, wherein the volumetric molar concentration of substrate is 0.21mol/L, and the volumetric molar concentration of catalyzer is 0.002mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 15h at normal temperatures, and centrifugal recovery catalyzer obtains 1 to crossing the post separation after the supernatant liquor underpressure distillation desolventizing, 2,4-triaminobenzene, productive rate are 94%.
Embodiment 13
Implementation method: at normal temperatures, with 1-fluoro-4-oil of mirbane and Rh
3Ni
1Place tetrahydrofuran (THF), wherein the volumetric molar concentration of substrate is 0.025mol/L, and the volumetric molar concentration of catalyzer is 0.0025mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 14h at normal temperatures, centrifugal recovery catalyzer obtains the 4-fluoroaniline to supernatant liquor underpressure distillation desolventizing, and productive rate is 99%.
Embodiment 14
Implementation method: at normal temperatures, with 1-methoxyl group-4-oil of mirbane and Rh
3Ni
1Place methyl alcohol, wherein the volumetric molar concentration of substrate is 0.025mol/L, and the volumetric molar concentration of catalyzer is 0.0002mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 22h at normal temperatures, centrifugal recovery catalyzer obtains the 4-anisidine to crossing the post separation after the supernatant liquor underpressure distillation desolventizing, and productive rate is 99%.
Embodiment 15
Implementation method: at normal temperatures, with 4-nitrobenzene methyl and Rh
3Ni
1Place methyl alcohol, wherein the volumetric molar concentration of substrate is 0.10mol/L, and the volumetric molar concentration of catalyzer is 0.0025mol/L.The airtight rear adding of reactor is full of the balloon of hydrogen, takes a breath continuously 3 times, under the state that stirs, mixture is reacted 24h at normal temperatures, centrifugal recovery catalyzer obtains the PABA methyl esters to crossing the post separation after the supernatant liquor underpressure distillation desolventizing, and productive rate is 94%.
Claims (4)
1. Rh
3Ni
1The catalytic reduction nitro-aromatic prepares the method for arylamine, it is characterized in that the method carries out as follows:
1) take nitro-aromatic as substrate, with bimetal Rh
3Ni
1Be catalyzer, under room temperature normal pressure nitrogen atmosphere, place organic solvent to react substrate and catalyzer, wherein the volumetric molar concentration of substrate is 0.05～0.5mol/L, and the volumetric molar concentration of catalyzer is 0.00015～0.004mol/L;
Described substrate structure formula is as follows,
Wherein R is selected from a kind of in hydrogen, alkyl, halogen, carbonyl, ether, amino, hydroxyl, methylol, ethanoyl and the ester group;
2) reacted 6～24 hours under the state that stirs, reaction finishes, and centrifugal recovery catalyzer supernatant liquor underpressure distillation desolventizing is obtained target product, or column chromatography for separation obtains target product.
2. a kind of Rh as claimed in claim 1
3Ni
1The catalytic reduction nitro-aromatic prepares the method for arylamine, it is characterized in that, used organic solvent adopts any in methyl alcohol, tetrahydrofuran (THF) and the ethyl acetate.
3. one kind is used for the as claimed in claim 1 Rh of method
3Ni
1Catalyzer is characterized in that this catalyzer prepares as follows:
1) stearylamine is added the thermosetting settled solution as solvent, tensio-active agent and reductive agent;
2) continue to be heated to 120～150 ° of C, then add three rhodium trichloride hydrates and acetylacetonate nickel, wherein the molality of three rhodium trichloride hydrates is 0.015～0.075mmol/g, and the molality of acetylacetonate nickel is 0.005～0.025mmol/g, obtains clarified liq;
3) under the state of high degree of agitation, above-mentioned clarified liq is injected in the stearylamine that is warming up in advance 230～250 ° of C dilutes, the molality of making three rhodium trichloride hydrates is 0.006～0.015mmol/g, and the molality of acetylacetonate nickel is the solution of 0.002～0.005mmol/g;
4) with mentioned solution under 230～250 ° of C aging 1.5～5 minutes, be cooled to and separate out throw out after adding ethanol behind 50 ° of C～80 ° C, centrifugally namely obtain bimetal Rh with washing with alcohol afterwards
3Ni
1, at last with the Rh that obtains
3Ni
1Be dispersed in the hexanaphthene for subsequent use.
4. Rh as claimed in claim 3
3Ni
1Catalyzer is characterized in that: this catalyzer is the mixture of worm-like particles and granular particles, and wherein the grain fineness number of granular particles is 6～10 nanometers.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496040A (en) * | 2016-10-10 | 2017-03-15 | 同济大学 | A kind of method that fragrant nitro compound transfer hydrogenation synthesizes arylamine |
| CN106748753A (en) * | 2016-12-28 | 2017-05-31 | 江苏扬农化工集团有限公司 | The method of ethanol ethyl acetate coproduction arylamine |
| CN108997138A (en) * | 2018-08-17 | 2018-12-14 | 济南和润化工科技有限公司 | A kind of method of solvent-free catalytic hydrogenation production para-fluoroaniline |
-
2012
- 2012-11-30 CN CN2012105073387A patent/CN102964194A/en active Pending
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| Title |
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| HAOHONG DUAN ET AL.: "Rhodium–nickel bimetallic nanocatalysts: high performance of room-temperature hydrogenation", 《CHEM. COMMUN.》 * |
| XIANGWEN LIU ET AL.: "Synthesis and catalytic properties of bimetallic nanomaterials with various architectures", 《NANO TODAY》 * |
| YUEN WU ET AL.: "Syntheses of Water-Soluble Octahedral, Truncated Octahedral, and Cubic Pt−Ni Nanocrystals and Their Structure−Activity Study in Model Hydrogenation Reactions", 《J. AM. CHEM. SOC.》 * |
| YUEN WU ET AL.: "Syntheses of Water-Soluble Octahedral, Truncated Octahedral, and Cubic Pt−Ni Nanocrystals and Their Structure−Activity Study in Model Hydrogenation Reactions", 《J. AM. CHEM. SOC.》, vol. 134, 22 April 2012 (2012-04-22) * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496040A (en) * | 2016-10-10 | 2017-03-15 | 同济大学 | A kind of method that fragrant nitro compound transfer hydrogenation synthesizes arylamine |
| CN106748753A (en) * | 2016-12-28 | 2017-05-31 | 江苏扬农化工集团有限公司 | The method of ethanol ethyl acetate coproduction arylamine |
| CN106748753B (en) * | 2016-12-28 | 2019-04-12 | 江苏扬农化工集团有限公司 | The method of ethyl alcohol ethyl acetate coproduction arylamine |
| CN108997138A (en) * | 2018-08-17 | 2018-12-14 | 济南和润化工科技有限公司 | A kind of method of solvent-free catalytic hydrogenation production para-fluoroaniline |
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Application publication date: 20130313 |