CN115041160A - Fixed bed 2-cyanopyridine catalyst and preparation method and application thereof - Google Patents
Fixed bed 2-cyanopyridine catalyst and preparation method and application thereof Download PDFInfo
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- CN115041160A CN115041160A CN202210851202.1A CN202210851202A CN115041160A CN 115041160 A CN115041160 A CN 115041160A CN 202210851202 A CN202210851202 A CN 202210851202A CN 115041160 A CN115041160 A CN 115041160A
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/28—Molybdenum
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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- Y02P20/584—Recycling of catalysts
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Abstract
The invention belongs to the technical field of catalytic synthesis, and discloses a fixed bed 2-cyanopyridine catalyst, and a preparation method and application thereof. Mixing citric acid, vanadium pentoxide and water to obtain a complex solution; dissolving molybdenum trioxide in hydrochloric acid to obtain a molybdenum trioxide solution; mixing the complex solution and the molybdenum trioxide solution, and adjusting the pH value to obtain a spraying liquid; and spraying the spraying liquid on a carrier, drying and activating to obtain the fixed bed 2-cyanopyridine catalyst. According to the invention, by controlling the raw material types and the component ratios of the catalysts, the weight yield of the 2-cyanopyridine generated by the fixed bed 2-cyanopyridine catalyst can reach 86-91%, the load can reach 80 g/h/tube, the catalytic activity of the fixed bed 2-cyanopyridine catalyst is improved, the generation of decarboxylation side reactions is reduced, and the method has the characteristics of environmental protection and high atom economy.
Description
Technical Field
The invention relates to the technical field of catalytic synthesis, in particular to a fixed bed 2-cyanopyridine catalyst and a preparation method and application thereof.
Background
2-cyanopyridine is used as an important intermediate of medicines and pesticides, can obtain fine chemicals such as amide, carboxylic acid, organic amine and the like through a series of reactions, and is widely used in fine chemical industries such as pesticides, foods, feed additives and the like. 2-cyanopyridine is produced primarily from 2-methylpyridine by ammoxidation, the key to the ammoxidation is the use of a catalyst which affects the conversion of 2-methylpyridine and the selectivity of 2-cyanopyridine.
At present, the catalyst for preparing 2-cyanopyridine by ammoxidation is usually a vanadium-based catalyst, such as a pure vanadium oxide catalyst, V 2 O 5 /TiO 2 Composite catalyst, V 2 O 5 /Sb 2 O 3 Composite catalyst, VP x Sb y O z The yield of the 2-cyanopyridine can reach 80% after the vanadium catalyst is used for catalytic reaction, and the catalyst has good catalytic activity. However, the preparation method of the catalyst is usually an impregnation method and a kneading and extruding molding method, which easily causes uneven catalyst loading, easy loss of active components and poor recycling property, and is not beneficial to efficient continuous production of enterprises.
Therefore, how to provide a catalyst for preparing 2-cyanopyridine by ammoxidation and a preparation method thereof have important significance for the development of the fine chemical industry.
Disclosure of Invention
The invention aims to provide a fixed bed 2-cyanopyridine catalyst, a preparation method and application thereof, and solves the problems of easy loss of active components and low catalytic efficiency of the existing catalyst.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a preparation method of a fixed bed 2-cyanopyridine catalyst, which comprises the following steps:
(1) mixing citric acid, vanadium pentoxide and water to obtain a complex solution;
dissolving molybdenum trioxide in hydrochloric acid to obtain a molybdenum trioxide solution;
mixing the complex solution and the molybdenum trioxide solution, and adjusting the pH value to obtain a spraying liquid;
(2) and spraying the spraying liquid on a carrier, drying and activating to obtain the fixed bed 2-cyanopyridine catalyst.
Preferably, in the preparation method of the fixed bed 2-cyanopyridine catalyst, in the step (1), the mass ratio of vanadium pentoxide to citric acid to molybdenum trioxide to water is 1-2: 3-6: 0.5-0.7: 15 to 18.
Preferably, in the preparation method of the fixed bed 2-cyanopyridine catalyst, the mass fraction of the hydrochloric acid in the step (1) is 30-37%; the mass-volume ratio of the molybdenum trioxide to the hydrochloric acid is 1-4 g: 1-5 mL.
Preferably, in the preparation method of the fixed bed 2-cyanopyridine catalyst, the pH in the step (1) is adjusted to 3-4 by using 25-28% by mass of ammonia water.
Preferably, in the above method for preparing a fixed bed 2-cyanopyridine catalyst, the carrier in the step (2) further comprises preheating before use; the preheating temperature is 70-80 ℃.
Preferably, in the preparation method of the fixed bed 2-cyanopyridine catalyst, the carrier in the step (2) is titanium dioxide, and the particle size of the carrier is 1-10 mm; the mass ratio of the spraying liquid to the carrier is 0.5-1: 1.
preferably, in the above method for preparing a fixed bed 2-cyanopyridine catalyst, the activation in the step (2) is activated by introducing air; the flow of the introduced air is 1-1.2 m 3 H; the activation temperature is 500-540 ℃; the activation time is 5-7 h.
The invention also provides a fixed bed 2-cyanopyridine catalyst prepared by the preparation method.
The invention also provides application of the fixed bed 2-cyanopyridine catalyst in catalyzing 2-methylpyridine to prepare 2-cyanopyridine.
Through the technical scheme, compared with the prior art, the invention has the following beneficial effects:
according to the invention, by controlling the raw material types and the component ratios of the catalysts, the weight yield of the 2-cyanopyridine generated by the fixed bed 2-cyanopyridine catalyst can reach 86-91%, the load can reach 80 g/h/tube, the catalytic activity of the fixed bed 2-cyanopyridine catalyst is improved, the generation of decarboxylation side reactions is reduced, and the method has the characteristics of environmental protection and high atom economy.
Detailed Description
The invention provides a preparation method of a fixed bed 2-cyanopyridine catalyst, which comprises the following steps:
(1) mixing citric acid, vanadium pentoxide and water to obtain a complex solution;
dissolving molybdenum trioxide in hydrochloric acid to obtain a molybdenum trioxide solution;
mixing the complex solution and the molybdenum trioxide solution, and adjusting the pH value to obtain a spraying liquid;
(2) and spraying the spraying liquid on a carrier, drying and activating to obtain the fixed bed 2-cyanopyridine catalyst.
In the invention, in the step (1), the mass ratio of vanadium pentoxide to citric acid to molybdenum trioxide to water is preferably 1-2: 3-6: 0.5-0.7: 15 to 18, and more preferably 1.2 to 1.9: 3.3-5.4: 0.54-0.68: 15.2 to 17.5, more preferably 1.6: 4.4: 0.58: 16.5. in the invention, citric acid is taken as a complexing agent, vanadium pentoxide is dissolved in an aqueous solution of citric acid, the pH of the solution is about 2.9, a vanadium complex exists in a valence state of +4, and the catalyst has optimal selectivity under the valence state. If the loading amount of vanadium pentoxide is too low, the activity of the catalyst is low, and the reaction is not facilitated; when the loading amount of vanadium pentoxide is too high, the vanadium pentoxide is not distributed in an amorphous state any more, but vanadium pentoxide crystals can appear to form isolated vanadium pentoxide to block micropores of the carrier, so that the activity of the catalyst is reduced. If the amount of citric acid is too small, vanadium pentoxide cannot be completely dissolved; too much citric acid, too low a solution pH, negatively affects the catalyst performance. If the content of the molybdenum trioxide is too low, the activity of the catalyst is easily greatly reduced, and the selectivity of the catalyst is influenced. The density of the solution is influenced by the amount of water, the water is too little, the density of the solution is too high, and the carrier is not easy to absorb, so that the falling rate of a finished catalyst product is high, and the catalyst can be cracked; too much water and too low solution density lead to low catalyst loading and affect catalyst activity.
In the invention, the method for mixing citric acid, vanadium pentoxide and water in the step (1) specifically comprises the following steps: mixing citric acid and water at 45-55 ℃, heating to 65-75 ℃, and adding vanadium pentoxide.
In the invention, the mass fraction of the hydrochloric acid in the step (1) is preferably 30-37%, more preferably 31-35%, and even more preferably 33%; the mass-volume ratio of the molybdenum trioxide to the hydrochloric acid is preferably 1-4 g: 1-5 mL, more preferably 1.3-3.6 g: 2-5 mL, more preferably 2 g: 3 mL.
In the invention, in the step (1), the pH is preferably adjusted to 3-4 by using 25-28% by mass of ammonia water, more preferably adjusted to 3.2-3.9 by using 26-28% by mass of ammonia water, and even more preferably adjusted to 3.4 by using 27% by mass of ammonia water.
In the invention, the carrier in the step (2) further comprises preheating before use; the preheating temperature is preferably 70-80 ℃, more preferably 71-78 ℃, and even more preferably 74 ℃.
In the invention, the temperature of the spraying liquid in the step (2) is preferably 70-75 ℃, more preferably 71-74 ℃, and even more preferably 72 ℃.
In the present invention, the carrier in the step (2) is preferably titanium dioxide; the particle size of the carrier is preferably 1-10 mm, more preferably 3-8 mm, and even more preferably 5 mm; the water absorption of the carrier is preferably not less than 0.4mL/g, more preferably not less than 0.45mL/g, and still more preferably not less than 0.55 mL/g; the mass ratio of the spraying liquid to the carrier is preferably 0.5-1: 1, more preferably 0.6 to 0.9: 1, more preferably 0.8: 1.
in the invention, the drying temperature in the step (2) is preferably 100-120 ℃, more preferably 105-117 ℃, and more preferably 113 ℃; the drying time is preferably 2 to 7 hours, more preferably 3 to 6 hours, and even more preferably 4 hours.
In the invention, the activation in the step (2) is preferably activated by introducing air; the flow rate of the introduced air is preferably 1-1.2 m 3 H, more preferably 1.1m 3 H; the activation temperature is preferably 500-540 ℃, more preferably 505-531 ℃, and more preferably 526 ℃; the activation time is preferably 5 to 7 hours, more preferably 5.3 to 6.7 hours, and even more preferably 6.1 hours.
The invention also provides a fixed bed 2-cyanopyridine catalyst prepared by the preparation method.
The invention also provides application of the fixed bed 2-cyanopyridine catalyst in catalyzing 2-methylpyridine to prepare 2-cyanopyridine.
In the invention, the method for preparing 2-cyanopyridine by catalyzing 2-methylpyridine comprises the following steps: and (3) loading the fixed bed 2-cyanopyridine catalyst into a fixed bed reactor, and introducing 2-methylpyridine, ammonia gas, water and air to perform reaction to obtain the 2-cyanopyridine.
In the present invention, the fixed bed reactor is preferably a reaction tube having a length of 4000mm and an inner diameter of 25 mm; the filling amount of the fixed bed 2-cyanopyridine catalyst in the fixed bed reactor is 1100g, the bed height is 2100mm, and an inert magnetic ring with the height of 50mm is arranged at the bottom of the bed.
In the present invention, the molar ratio of the 2-methylpyridine, ammonia gas, water and air is preferably 1: 6: 3.5: 25.
in the invention, the reaction temperature is preferably 345-375 ℃, more preferably 347-368 ℃, and more preferably 353 ℃; the reaction time is preferably 6 to 8 hours, more preferably 6.5 to 7.5 hours, and even more preferably 7 hours.
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
This example provides a fixed bed 2-cyanopyridine catalyst, the preparation method of which comprises the following steps:
(1) mixing citric acid and water at 45 ℃, heating to 65 ℃, adding vanadium pentoxide, and uniformly stirring to obtain a complex solution; dissolving molybdenum trioxide in hydrochloric acid with the mass fraction of 37% to obtain a molybdenum trioxide solution; mixing the complex solution and the molybdenum trioxide solution, adjusting the pH to 3.2 by using ammonia water with the mass fraction of 27% to obtain a spraying liquid, and keeping the temperature at 70 ℃ for later use;
wherein the mass volume ratio of vanadium pentoxide to citric acid to molybdenum trioxide to water to hydrochloric acid is 1 g: 3 g: 0.5 g: 15 g: 1 mL;
(2) preheating titanium dioxide (with the particle size of 4-5 mm and the water absorption of 0.4mL/g) to 70 ℃, starting a spray head switch of a spraying tank, spraying a spraying liquid on the titanium dioxide (the mass ratio of the spraying liquid to a carrier is 0.8: 1), and then drying at 110 ℃ for 4 hours to obtain a semi-finished catalyst;
placing the catalyst semi-finished product in a heating furnace at a rate of 1m 3 Air is introduced at the flow rate of/h, and the catalyst is activated for 6h at 520 ℃ to obtain the fixed bed 2-cyanopyridine catalyst.
Example 2
This example provides a fixed bed 2-cyanopyridine catalyst, the preparation method of which comprises the following steps:
(1) mixing citric acid and water at 50 ℃, heating to 70 ℃, adding vanadium pentoxide, and uniformly stirring to obtain a complex solution; dissolving molybdenum trioxide in hydrochloric acid with the mass fraction of 37% to obtain a molybdenum trioxide solution; mixing the complex solution and the molybdenum trioxide solution, adjusting the pH to 3.4 by using ammonia water with the mass fraction of 25% to obtain a spraying liquid, and keeping the temperature at 75 ℃ for later use;
wherein the mass volume ratio of the vanadium pentoxide to the citric acid to the molybdenum trioxide to the water to the hydrochloric acid is 2 g: 6 g: 0.7 g: 18 g: 2 mL;
(2) preheating titanium dioxide (with the particle size of 4.5-5 mm and the water absorption of 0.5mL/g) to 80 ℃, starting a nozzle switch of a spraying tank, spraying a spraying liquid on the titanium dioxide (the mass ratio of the spraying liquid to a carrier is 0.7: 1), and drying at 105 ℃ for 5 hours to obtain a semi-finished catalyst;
placing the catalyst semi-finished product in a heating furnace at a speed of 1.2m 3 And introducing air at the flow rate of/h, and activating at 530 ℃ for 5h to obtain the fixed bed 2-cyanopyridine catalyst.
Example 3
This example provides a fixed bed 2-cyanopyridine catalyst, the preparation method of which comprises the following steps:
(1) mixing citric acid and water at 55 ℃, heating to 75 ℃, adding vanadium pentoxide, and uniformly stirring to obtain a complex solution; dissolving molybdenum trioxide in hydrochloric acid with the mass fraction of 37% to obtain a molybdenum trioxide solution; mixing the complex solution and the molybdenum trioxide solution, adjusting the pH to 4 by using ammonia water with the mass fraction of 28% to obtain a spraying liquid, and keeping the temperature at 75 ℃ for later use;
wherein the mass volume ratio of the vanadium pentoxide to the citric acid to the molybdenum trioxide to the water to the hydrochloric acid is 2 g: 6 g: 0.6 g: 17 g: 1.2 mL;
(2) preheating titanium dioxide (with the particle size of 7-8 mm and the water absorption of 0.6mL/g) to 76 ℃, starting a spray head switch of a spraying tank, spraying a spraying liquid on the titanium dioxide (the mass ratio of the spraying liquid to a carrier is 0.9: 1), and then drying at 115 ℃ for 4 hours to obtain a semi-finished catalyst;
placing the catalyst semi-finished product in a heating furnace at a speed of 1.1m 3 Air is introduced at the flow rate of/h, and the catalyst is activated for 7h at 540 ℃ to obtain the fixed bed 2-cyanopyridine catalyst.
Example 4
The method for preparing 2-cyanopyridine by catalyzing 2-methylpyridine by using the fixed bed 2-cyanopyridine catalyst in example 1 comprises the following steps:
1100g of fixed bed 2-cyanopyridine catalyst is loaded into a fixed bed reactor (a single tube of a reaction tube with the length of 4000mm and the inner diameter of 25 mm), the height of a bed layer is controlled to be 2100mm, and an inert magnetic ring with the height of 50mm is placed at the bottom of the bed layer; then 2-methylpyridine, ammonia gas, water and air (molar ratio is 1: 6: 3.5: 25) are introduced to react for 6h at 347 ℃, so that 2-cyanopyridine is obtained with the weight yield of 88%.
Example 5
The method for preparing 2-cyanopyridine by catalyzing 2-methylpyridine by using the fixed bed 2-cyanopyridine catalyst in example 2 comprises the following steps:
1100g of fixed bed 2-cyanopyridine catalyst is loaded into a fixed bed reactor (a single tube of a reaction tube with the length of 4000mm and the inner diameter of 25 mm), the height of a bed layer is controlled to be 2100mm, and an inert magnetic ring with the height of 50mm is placed at the bottom of the bed layer; then 2-methylpyridine, ammonia gas, water and air (molar ratio is 1: 6: 3.5: 25) are introduced to react for 6h at 373 ℃ to obtain 2-cyanopyridine with the weight yield of 86%.
Example 6
The method for preparing 2-cyanopyridine by catalyzing 2-methylpyridine by using the fixed bed 2-cyanopyridine catalyst in example 3 comprises the following steps:
1100g of fixed bed 2-cyanopyridine catalyst is loaded into a fixed bed reactor (a single tube of a reaction tube with the length of 4000mm and the inner diameter of 25 mm), the height of a bed layer is controlled to be 2100mm, and an inert magnetic ring with the height of 50mm is placed at the bottom of the bed layer; then 2-methylpyridine, ammonia gas, water and air (molar ratio is 1: 6: 3.5: 25) are introduced to react for 8 hours at 353 ℃, so that 2-cyanopyridine is obtained with the weight yield of 91%.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (9)
1. A preparation method of a fixed bed 2-cyanopyridine catalyst is characterized by comprising the following steps:
(1) mixing citric acid, vanadium pentoxide and water to obtain a complex solution;
dissolving molybdenum trioxide in hydrochloric acid to obtain a molybdenum trioxide solution;
mixing the complex solution and the molybdenum trioxide solution, and adjusting the pH value to obtain a spraying liquid;
(2) and spraying the spraying liquid on a carrier, drying and activating to obtain the fixed bed 2-cyanopyridine catalyst.
2. The preparation method of the fixed bed 2-cyanopyridine catalyst as claimed in claim 1, wherein the mass ratio of vanadium pentoxide to citric acid to molybdenum trioxide to water in step (1) is 1-2: 3-6: 0.5-0.7: 15 to 18.
3. The preparation method of the fixed bed 2-cyanopyridine catalyst according to claim 1 or 2, wherein the mass fraction of the hydrochloric acid in the step (1) is 30-37%; the mass-volume ratio of the molybdenum trioxide to the hydrochloric acid is 1-4 g: 1-5 mL.
4. The method for preparing a fixed bed 2-cyanopyridine catalyst according to claim 1 or 2, wherein the pH is adjusted to 3 to 4 in step (1) by using 25 to 28% by mass of ammonia water.
5. The process for preparing a fixed bed 2-cyanopyridine catalyst in accordance with claim 4, wherein said step (2) further comprises preheating the support before use; the preheating temperature is 70-80 ℃.
6. The method for preparing a fixed bed 2-cyanopyridine catalyst according to claim 1, 2 or 5, wherein in the step (2), the carrier is titanium dioxide, and the particle size of the carrier is 1-10 mm; the mass ratio of the spraying liquid to the carrier is 0.5-1: 1.
7. the method for preparing a fixed bed 2-cyanopyridine catalyst in accordance with claim 6, wherein the activation in the step (2) is an activation by introducing air; the flow of the introduced air is 1-1.2 m 3 H; the activation temperature is 500-540 ℃; the activation time is 5-7 h.
8. A fixed bed 2-cyanopyridine catalyst obtainable by the process of any one of claims 1 to 7.
9. Use of a fixed bed 2-cyanopyridine catalyst of claim 8 in the catalysis of 2-methylpyridine to produce 2-cyanopyridine.
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| US3970657A (en) * | 1975-11-18 | 1976-07-20 | Merck & Co., Inc. | Preparation of cyanopyridines |
| CN101433836A (en) * | 2008-12-05 | 2009-05-20 | 浙江师范大学 | Catalyst for producing 3-cyano pyridine as well as preparation method and use thereof |
| CN104072414A (en) * | 2014-07-04 | 2014-10-01 | 兰州大学 | Method for preparing cyanopyridine |
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| CN105749984A (en) * | 2014-12-16 | 2016-07-13 | 中国石油化工股份有限公司 | Hydrogenation catalyst and preparation method thereof and preparation method of tertralin |
| CN107537537A (en) * | 2017-09-19 | 2018-01-05 | 河南省科学院高新技术研究中心 | A kind of catalyst that 2 cyanopyridines are prepared for ammoxidation reaction |
| CN108126723A (en) * | 2017-12-29 | 2018-06-08 | 兄弟科技股份有限公司 | A kind of catalyst for being used to prepare nicotinonitrile and preparation method thereof |
-
2022
- 2022-07-20 CN CN202210851202.1A patent/CN115041160A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3970657A (en) * | 1975-11-18 | 1976-07-20 | Merck & Co., Inc. | Preparation of cyanopyridines |
| CN101433836A (en) * | 2008-12-05 | 2009-05-20 | 浙江师范大学 | Catalyst for producing 3-cyano pyridine as well as preparation method and use thereof |
| CN104072414A (en) * | 2014-07-04 | 2014-10-01 | 兰州大学 | Method for preparing cyanopyridine |
| CN105749984A (en) * | 2014-12-16 | 2016-07-13 | 中国石油化工股份有限公司 | Hydrogenation catalyst and preparation method thereof and preparation method of tertralin |
| CN105618078A (en) * | 2015-12-07 | 2016-06-01 | 沧州临港亚诺化工有限公司 | Catalyst for performing ammoxidation on alkyl pyridinium |
| CN107537537A (en) * | 2017-09-19 | 2018-01-05 | 河南省科学院高新技术研究中心 | A kind of catalyst that 2 cyanopyridines are prepared for ammoxidation reaction |
| CN108126723A (en) * | 2017-12-29 | 2018-06-08 | 兄弟科技股份有限公司 | A kind of catalyst for being used to prepare nicotinonitrile and preparation method thereof |
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