CN111153824A - Method for preparing amide compound by catalyzing organic nitrile hydration with oxide material - Google Patents
Method for preparing amide compound by catalyzing organic nitrile hydration with oxide material Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07—ORGANIC CHEMISTRY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Abstract
The invention relates to a catalyst for preparing amide compounds, and aims to provide a method for preparing amide compounds by catalyzing organic nitrile hydration by using an oxide material. The method comprises the following steps: adding a solvent, an organic nitrile substrate, water and a catalyst into a sealable reaction vessel, and uniformly mixing; controlling the reaction temperature to be 50-180 ℃ and the reaction time to be 0.5-24 h; the nitrile compound is finally hydrated and converted into the corresponding amide compound by catalytic hydration in the reaction process. The catalyst is cheap and easy to obtain, and any noble metal is not used, so that the preparation cost of the catalyst is low, and the large-scale production of the catalyst is facilitated. The reaction process has high atom utilization rate and low reaction temperature, no reaction auxiliary agent is required to be additionally added in the synthesis process, no toxic and harmful by-products are generated after the reaction, and the whole synthesis process is green and environment-friendly.
Description
Technical Field
The invention relates to a catalyst for preparing amide compounds by hydration, in particular to a method for preparing amide compounds by catalyzing organic nitriles to hydrate by using oxides.
Background
Amides, which are important chemical products, have high economic and application values and are widely used in daily life, industrial production, and medical and health fields (for example, amides can be used as important intermediates in organic synthesis reactions, and as a raw material in the synthesis of plastics, pigments, detergents, lubricants, etc.). The conventional synthesis method of amide comprises: (1) carboxylic acid and its derivatives (such as acyl chloride, acid anhydride, ester) and amines (including ammonia) are subjected to condensation acylation reaction to obtain amide; (2) and performing acid-catalyzed rearrangement reaction on the ketoxime to obtain amide and the like. However, the synthesis of amides by these conventional methods is often accompanied by the production of a large amount of toxic chemical by-products, which can pollute the ecological environment and harm the health. Therefore, a green pollution-free path is searched for synthesizing the amide, and a large amount of chemical reagents or acidic and alkaline media are avoided.
The direct preparation of amide by direct hydration of organic nitrile compounds is a good alternative to the traditional method for producing amide, standing on the green chemistry, the process has the advantages of extremely high atomic efficiency and no generation of toxic byproducts (1 molecule of organic nitrile reacts with 1 molecule of water to generate 1 molecule of amide, and theoretically, the atomic utilization rate is 100%). In this hydration process, the activation of water molecules is an important control step in determining the reaction rate, but conventional non-noble metal catalysts have difficulty in activating water molecules, and therefore, it is generally necessary to use noble metal catalysts and catalyze the process under relatively severe conditions, such as noble metal Ru, at a temperature of 130 ℃ (Angew. chem. int. Ed.2004,43, 1576-; the noble metal Pd is used for reaction at 140 ℃ (ACS Catal.2012,2,2467-2474) and the like, thereby bringing the defects of high cost, large energy consumption and the like. Therefore, it is of great importance to find a method for carrying out the process under mild conditions by preparing a highly active, inexpensive catalyst.
Disclosure of Invention
The invention aims to solve the technical problem of overcoming the defects in the prior art and provides a method for preparing an amide compound by catalyzing organic nitrile hydration by using an oxide material.
In order to solve the technical problem, the solution of the invention is as follows:
the method for preparing the amide compound by catalyzing organic nitrile hydration by using the oxide material comprises the following steps:
(1) adding a solvent, an organic nitrile substrate, water and a catalyst into a sealable reaction vessel, and uniformly mixing; in the mixture, the mass percent of the catalyst is 0.04-10.6%, the mass percent of the organic nitrile substrate is 0.01-75.5%, the mass percent of the water is 0.01-19.1%, and the balance is solvent;
(2) controlling the reaction temperature to be 50-180 ℃ and the reaction time to be 0.5-24 hours; in the reaction process, the nitrile compound is finally hydrated and converted into the corresponding amide compound through catalytic hydration;
the active component of the catalyst is a metal oxide of any one or more of the following metal elements: fe. Ce, Co, Mn, Cu or Ni.
In the present invention, the metal oxide is any one of the following, or a mixed oxide composed of two or more crystal phases: (1) ferric oxide or ferrous oxide; (2) cerium oxide; (3) cobaltosic oxide; (4) manganese sesquioxide, manganomanganic oxide or manganese dioxide; (5) copper oxide; (6) and (3) nickel oxide.
In the present invention, the catalyst is a powdery ore material containing any one of the following metal oxides or two or more mixed phase oxides.
In the present invention, the solvent is any one or more of the following: water, tert-butanol, tert-amyl alcohol, toluene, dichloromethane, chloroform, dimethyl sulfoxide or acetone.
In the present invention, the organic nitrile substrate is any one or more of the following: benzonitrile, o-methoxybenzonitrile, 3-methoxybenzonitrile, 4-methoxybenzonitrile, p-fluorobenzonitrile, p-chlorobenzonitrile, p-bromobenzonitrile, 4- (trifluoromethyl) benzonitrile, 4-methylbenzonitrile, 2-cyanofuran, 3-cyanopyridine, 3-cyanothiophene, 2-cyanopyridine, 4-cyanopyridine or heptanenitrile.
Description of the inventive principles:
the invention takes the oxides of metals such as iron, cerium, cobalt, manganese and the like as catalysts, and can obtain oxide materials which are beneficial to activating water molecules by utilizing a mature preparation method and surface engineering, thereby catalyzing the hydration of organic nitrile compounds to prepare amide compounds. The whole process can be realized at a lower temperature, the use of noble metal or addition of an auxiliary agent is avoided, no toxic and harmful by-products are generated in the reaction process, and the method is green and environment-friendly.
Compared with the prior art, the invention has the beneficial effects that:
1. the catalyst provided by the invention is cheap and easy to obtain, and the active component in the catalyst is oxide of metal which is stored in the nature and is rich, and no precious metal is used, so that the preparation cost of the catalyst is low, and the large-scale production of the catalyst is facilitated.
2. The invention provides a more efficient method for preparing amide compounds, the atom utilization rate in the reaction process is high, the reaction temperature is low, no reaction auxiliary agent needs to be added in the synthesis process, no toxic and harmful by-products are generated after the reaction, and the whole synthesis process is environment-friendly.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments. The reactions of the following examples were all carried out in a closable reaction vessel. The examples may provide those skilled in the art with a more complete understanding of the present invention, and are not intended to limit the invention in any way.
Example 1
300mg of ferric oxide (mass% in the mixture: 4.6%; the catalyst is used herein, the same applies hereinafter), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 76.8%, and the selectivity to benzamide was 90.0%.
Example 2
To 6g of methylene chloride were added 300mg of ferrous oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%), followed by mixing uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 74.5%, and the selectivity to benzamide was 84.3%.
Example 3
To 6g of methylene chloride were added 300mg of cerium oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), and 200uL of water (mass% in the mixture: 3.0%), followed by mixing uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 50.9%, and the selectivity to benzamide was 93.8%.
Example 4
To 6g of methylene chloride were added 300mg of tricobalt tetroxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), and 200uL of water (mass% in the mixture: 3.0%), followed by mixing uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 64.5%, and the selectivity to benzamide was 95.1%.
Example 5
300mg of manganese oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed well; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 60.2%, and the selectivity of the corresponding benzamide is 98.3%.
Example 6
To 6g of methylene chloride were added 300mg of trimanganese tetroxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%), followed by uniform mixing; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 52.1%, and the selectivity to benzamide was 98.9%.
Example 7
300mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 67.4%, and the selectivity to benzamide was 95.6%.
Example 8
To 6g of methylene chloride were added 300mg of copper oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%), followed by mixing uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 42.1%, and the selectivity to benzamide was 93.5%.
Example 9
To 6g of methylene chloride were added 300mg of nickel oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), and 200uL of water (mass% in the mixture: 3.0%), followed by mixing uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 32.6%, and the selectivity to benzamide was 91.9%.
Based on the fact that ferric oxide (example 1) shows more excellent catalytic performance than ferrous oxide (example 2), mixed oxides of ferric oxide and other metal oxides are selected between the ferric oxide and the ferrous oxide, and the catalytic hydration performance of the mixed oxides is examined.
Example 10
150mg of iron trioxide and 150mg of ceria (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 83.7%, and the selectivity to benzamide was 92.7%.
Example 11
150mg of iron sesquioxide and 150mg of cobaltosic oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the benzonitrile conversion was 89.2%, and the selectivity to benzamide was 95.7%.
Manganese dioxide (example 7) was selected among the three to form a mixed oxide with other metal oxides, and catalytic hydration properties thereof were examined, based on the fact that manganese dioxide (example 5) showed more excellent catalytic properties than manganese dioxide (example 5) and manganese tetraoxide (example 6).
Example 12
150mg of iron sesquioxide and 150mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of methylene chloride, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 93.2%, and the selectivity to benzamide was 96.3%.
Example 13
150mg of iron sesquioxide and 150mg of copper oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of methylene chloride and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 79.3%, and the selectivity to benzamide was 90.4%.
Example 14
150mg of iron trioxide and 150mg of nickel oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 76.9%, and the selectivity to benzamide was 89.8%.
Example 15
150mg of cerium oxide and 150mg of tricobalt tetraoxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 70.1%, and the selectivity to benzamide was 95.9%.
Example 16
150mg of cerium oxide and 150mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 84.6%, and the selectivity to benzamide was 97.2%.
Example 17
150mg of cerium oxide and 150mg of copper oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of methylene chloride and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 56.0%, and the selectivity to benzamide was 93.3%.
Example 18
150mg of cerium oxide and 150mg of nickel oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of methylene chloride and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 39.1%, and the selectivity to benzamide was 91.0%.
Example 19
To 6g of methylene chloride were added 150mg of cobaltosic oxide and 150mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%), followed by mixing uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 95.3%, and the selectivity to benzamide was 98.9%.
Example 20
150mg of tricobalt tetraoxide and 150mg of copper oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 63.6%, and the selectivity to benzamide was 94.9%.
Example 21
150mg of tricobalt tetroxide and 150mg of nickel oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 53.6%, and the selectivity to benzamide was 94.3%.
Example 22
150mg of manganese dioxide and 150mg of copper oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 70.2%, and the selectivity to benzamide was 95.0%.
Example 23
150mg of manganese dioxide and 150mg of nickel oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 63.0%, and the selectivity to benzamide was 93.5%.
Example 24
To 6g of methylene chloride were added 150mg of copper oxide and 150mg of nickel oxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%), and they were mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, the conversion of benzonitrile was 33.8%, and the selectivity to benzamide was 90.5%.
Example 25
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 98.5%, and the selectivity of corresponding benzamide is 99.0%.
Example 26
1mg of ferric oxide, 1mg of cobaltosic oxide and 1mg of manganese dioxide (mass% in the mixture: 0.04%), 60mg of benzonitrile (mass% in the mixture: 0.96%), 200uL of water (mass% in the mixture: 3.2%) were added to 6g of dichloromethane, and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of the benzonitrile is 2.3 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 27
To 6g of methylene chloride were added 250mg of iron sesquioxide, 250mg of cobaltosic oxide and 250mg of manganese dioxide (mass% in the mixture: 10.6%), 60mg of benzonitrile (mass% in the mixture: 0.86%), 200uL of water (mass% in the mixture: 2.9%), followed by mixing; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is more than 99.0 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 28
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 1mg of benzonitrile (mass% in the mixture: 0.01%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of dichloromethane, and mixed uniformly; the reaction is carried out for 24 hours at 80 ℃, the conversion rate of benzonitrile is more than 99.0 percent, and the selectivity of corresponding benzamide is 29.1 percent.
Example 29
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 2.9%), 4g of benzonitrile (mass% in the mixture: 38.1%), 200uL of water (mass% in the mixture: 1.9%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours with a benzonitrile conversion of 38.1% and a corresponding benzamide selectivity of > 99.0%.
Example 30
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 1.1%), 20g of benzonitrile (mass% in the mixture: 75.5%), 200uL of water (mass% in the mixture: 0.75%) were added to 6g of dichloromethane, and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours with a benzonitrile conversion of 5.5% and a corresponding benzamide selectivity of > 99.0%.
Example 31
To 6g of chloroform were added 100mg of ferric oxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%), followed by mixing; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 97.9 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 32
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass percentage in the mixture: 4.6%), 60mg of benzonitrile (mass percentage in the mixture: 0.91%), 200uL of water (mass percentage in the mixture: 3.0%) were added to 6g of dimethyl sulfoxide, and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 98.8%, and the selectivity of corresponding benzamide is 99.0%.
Example 33
100mg of ferric oxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of acetone and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 99.0 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 34
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of water and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 99.0 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 35
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 99.0 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 36
100mg of ferric oxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-butanol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 99.0 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 37
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of toluene, and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 68.3 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 38
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at 50 ℃, the conversion rate of benzonitrile is 85.9 percent, and the selectivity of corresponding benzamide is 99.0 percent.
Example 39
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at 130 ℃, the conversion rate of benzonitrile is 99.0 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 40
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at 180 ℃, the conversion rate of benzonitrile is 99.0 percent, and the selectivity of the corresponding benzamide is 86.8 percent.
EXAMPLE 41
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction was carried out at 80 ℃ for 0.5 hour, the conversion of benzonitrile was 72.2%, and the selectivity to benzamide was 99.0%.
Example 42
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 12 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 99.0 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 43
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.7%), 60mg of benzonitrile (mass% in the mixture: 0.94%), 1uL of water (mass% in the mixture: 0.01%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is 8.9%, and the selectivity of corresponding benzamide is 99.0%.
Example 44
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.2%), 60mg of benzonitrile (mass% in the mixture: 0.85%), 700uL of water (mass% in the mixture: 9.9%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is more than 99.0 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 45
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 3.8%), 60mg of benzonitrile (mass% in the mixture: 0.76%), 1.5mL of water (mass% in the mixture: 19.1%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of benzonitrile is more than 99.0 percent, and the selectivity of the corresponding benzamide is 99.0 percent.
Example 46
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of o-methoxybenzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of the o-methoxybenzonitrile is 89.5 percent, and the selectivity of the corresponding o-methoxybenzamide is 99.0 percent.
Example 47
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of 3-methoxybenzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of the 3-methoxybenzonitrile is 99.0 percent, and the selectivity of the corresponding 3-methoxybenzamide is 99.0 percent.
Example 48
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of 4-methoxybenzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of the 4-methoxybenzonitrile is 99.0 percent, and the selectivity of the corresponding 4-methoxybenzamide is 99.0 percent.
Example 49
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of p-fluorobenzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of the p-fluorobenzonitrile is 99.0 percent, and the selectivity of the corresponding p-fluorobenzamide is 99.0 percent.
Example 50
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of p-chlorobenzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of the p-chlorobenzonitrile is 99.0 percent, and the selectivity of the corresponding p-chlorobenzamide is 99.0 percent.
Example 51
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of p-bromobenzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of the p-bromobenzonitrile is 99.0 percent, and the selectivity of the corresponding p-bromobenzamide is 99.0 percent.
Example 52
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of 4- (trifluoromethyl) benzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, with a conversion of 4- (trifluoromethyl) benzonitrile of 99.0% and a selectivity to the corresponding 4- (trifluoromethyl) benzamide of 99.0%.
Example 53
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of 4-methylbenzonitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, with a 4-methylbenzonitrile conversion of 99.0% and a corresponding 4-methylbenzamide selectivity of 99.0%.
Example 54
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of 2-cyanofuran (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of the 2-cyano furan is 99.0 percent, and the selectivity of the corresponding furfuryl amide is 99.0 percent.
Example 55
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of 3-cyanopyridine (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of the 3-cyanopyridine is 99.0 percent, and the selectivity of the corresponding nicotinamide is 99.0 percent.
Example 56
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of 3-cyanothiophene (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction is carried out for 24 hours at the temperature of 80 ℃, the conversion rate of the 3-cyanothiophene is 99.0 percent, and the selectivity of the corresponding 3-thiophenecarboxamide is 99.0 percent.
Example 57
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of 2-cyanopyridine (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, with a conversion of 99.0% for 2-cyanopyridine and a selectivity of 99.0% for the corresponding 2-pyridinecarboxamide.
Example 58
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of 4-cyanopyridine (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, with a 4-cyanopyridine conversion of 99.0% and a corresponding 4-pyridinecarboxamide selectivity of 99.0%.
Example 59
100mg of iron sesquioxide, 100mg of cobaltosic oxide and 100mg of manganese dioxide (mass% in the mixture: 4.6%), 60mg of heptanitrile (mass% in the mixture: 0.91%), 200uL of water (mass% in the mixture: 3.0%) were added to 6g of t-amyl alcohol and mixed uniformly; the reaction was carried out at 80 ℃ for 24 hours, with a heptanitrile conversion of 68.9% and a corresponding heptanamide selectivity of 99.0%.
Finally, it should be noted that the above-mentioned list is only a specific embodiment of the present invention. Obviously, the invention is not limited to the above embodiments, but may be modified in many ways, such as: in the mixed oxide composed of multiple crystal phases, the ratio of each crystal phase is not limited to 1: 1, can be mixed in any proportion. All modifications which can be derived or suggested by a person skilled in the art from the disclosure of the present invention are to be considered within the scope of the invention.
Claims (5)
1. A method for preparing amide compounds by catalyzing organic nitrile hydration by using oxide materials is characterized by comprising the following steps:
(1) adding a solvent, an organic nitrile substrate, water and a catalyst into a sealable reaction vessel, and uniformly mixing; in the mixture, the mass percent of the catalyst is 0.04-10.6%, the mass percent of the organic nitrile substrate is 0.01-75.5%, the mass percent of the water is 0.01-19.1%, and the balance is solvent;
(2) controlling the reaction temperature to be 50-180 ℃ and the reaction time to be 0.5-24 hours; in the reaction process, the nitrile compound is finally hydrated and converted into the corresponding amide compound through catalytic hydration;
the active component of the catalyst is a metal oxide of any one or more of the following metal elements: fe. Ce, Co, Mn, Cu or Ni.
2. The method according to claim 1, wherein the metal oxide is any one of the following, or a mixed oxide composed of two or more crystal phases: (1) ferric oxide or ferrous oxide; (2) cerium oxide; (3) cobaltosic oxide; (4) manganese sesquioxide, manganomanganic oxide or manganese dioxide; (5) copper oxide; (6) and (3) nickel oxide.
3. The method according to claim 1, wherein the catalyst is a powdery ore material containing any one of the following metal oxides or two or more mixed oxides.
4. The method of claim 1, wherein the solvent is any one or more of: water, tert-butanol, tert-amyl alcohol, toluene, dichloromethane, chloroform, dimethyl sulfoxide or acetone.
5. The method according to claim 1, wherein the organonitrile substrate is any one of: benzonitrile, o-methoxybenzonitrile, 3-methoxybenzonitrile, 4-methoxybenzonitrile, p-fluorobenzonitrile, p-chlorobenzonitrile, p-bromobenzonitrile, 4- (trifluoromethyl) benzonitrile, 4-methylbenzonitrile, 2-cyanofuran, 3-cyanopyridine, 3-cyanothiophene, 2-cyanopyridine, 4-cyanopyridine or heptanenitrile.
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