CN113893785B - Pyridine base synthesis method and device - Google Patents
Pyridine base synthesis method and device Download PDFInfo
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- CN113893785B CN113893785B CN202111387435.2A CN202111387435A CN113893785B CN 113893785 B CN113893785 B CN 113893785B CN 202111387435 A CN202111387435 A CN 202111387435A CN 113893785 B CN113893785 B CN 113893785B
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- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0476—Moving receptacles, e.g. rotating receptacles
- B01D11/048—Mixing by counter-current streams provoked by centrifugal force, in rotating coils or in other rotating spaces
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
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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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
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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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0292—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate
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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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/10—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from acetaldehyde or cyclic polymers thereof
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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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Pyridine Compounds (AREA)
Abstract
The invention discloses a method and a device for synthesizing pyridine base, which comprises the following steps: activating the catalyst: fixing ZSM-5 molecular sieve loaded with ionic liquid as a catalyst on a distributor of a reactor, introducing nitrogen to activate for 2-4h at 300-350 ℃, introducing gasified mixed aldehyde into a bottom catalyst bed layer of the reactor through a bottom sleeve, and simultaneously introducing NH 3 Reacting, wherein reaction gas and a catalyst enter a regenerator through the top of a reactor, the catalyst is regenerated in the regenerator after passing through a gas-solid separator, the reaction gas discharged from the reactor sequentially enters an evaporator and a heat exchanger for cooling, the evaporator generates steam, and the heat exchanger heats raw materials; and (3) feeding the product from the heat exchanger into a centrifugal extractor, an evaporative condenser and a rectifying tower to separate a pyridine base product. The invention adopts the reactor of the renewable catalyst to synthesize the pyridine base on the basis of adopting the zeolite molecular sieve loaded by the ionic liquid, thereby improving the yield of the pyridine base.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a pyridine base synthesis method and device.
Background
Pyridine and its derivatives are very important chemical intermediates, widely used in the industries of medicine, pesticide, feed, synthetic rubber and dye, and also used in the production of surfactants, food additives and the like. Pyridine is mainly used in industry for producing sulfanilamide, penicillin, vitamin A, cortisone, anthelmintic, local anesthetic, etc., as well as for stabilizing agent, softener, paint solvent, condensing agent of synthetic resin, and for synthesizing herbicide, antiseptic, hydroxypyridine, etc.
The prior process for synthesizing pyridine base by an aldehyde ammonia method mainly adopts a metal-loaded ZSM-5 molecular sieve, so that the service life is short, and the yield of pyridine base is lower. Chinese patent CN200710150336.6 discloses a novel catalyst for synthesizing pyridine base and a preparation method and a use method thereof, a high-silicon molecular sieve is used as a matrix, and is subjected to dealuminization and desilication treatment to be used for preparing pyridine base in a catalytic manner, and the yield of the pyridine base can reach more than 65%; however, the yield of pyridine base catalytically synthesized by the catalyst is relatively low, and the steps are complicated because deacidification and desilication treatment are required.
In conclusion, the existing pyridine base production process has the following defects:
the yield of the pyridine base synthesis process by the aldehyde-ammonia method is low at present, formaldehyde and acetaldehyde are coked and blocked at the inlet of a reactor in the reaction process, the temperature is too high in the reaction process, heat is difficult to remove, the service life of a catalyst is short, and the product yield is low.
Disclosure of Invention
The invention aims to provide a pyridine base synthesis method and a pyridine base synthesis device, wherein the pyridine base is synthesized by adopting a reactor of a renewable catalyst on the basis of an ionic liquid loaded zeolite molecular sieve, the pyridine base yield is more than 87%, and the problems in the background art can be solved.
In order to achieve the purpose, the invention provides the following technical scheme:
a synthetic method of pyridine base comprises the following steps:
the method comprises the following steps: with formaldehyde, acetaldehyde and NH 3 Taking ZSM-5 molecular sieve loaded with ionic liquid as a catalyst to synthesize pyridine base, wherein the loaded ionic liquid is imidazole tetrafluoroborate ([ CnCnmim)][BF 4 ])；
Step two: activating the catalyst: fixing the catalyst on a distributor of a reactor, and then introducing nitrogen to activate for 2-4h at 300-350 ℃;
step three: reaction: after activation, the temperature is raised to the reaction temperature, the mixed aldehyde is gasified and then enters a bottom catalyst bed layer of the reactor through a bottom sleeve, and NH is introduced at the same time 3 Reacting, wherein reaction gas and a catalyst enter a regenerator through the top of the reactor, the reactor enters a post-treatment process after passing through a gas-solid separator, the catalyst is regenerated in the regenerator, and the regenerated catalyst enters the reactor for continuous reaction;
step four: cooling: the reaction gas from the reactor enters an evaporator after passing through a regenerator and a gas-solid separator, and then enters a heat exchanger for condensation, the evaporator generates steam, and the heat exchanger is connected with a mixed aldehyde inlet pipe to heat the raw materials;
step five: separation: and (3) feeding the product from the heat exchanger into a centrifugal extractor, an evaporative condenser and a rectifying tower to separate a pyridine base product.
Further, the content of the imidazole tetrafluoroborate in the catalyst is 0.1-10%, preferably 0.5-5%.
Further, the formaldehyde: acetaldehyde: NH (NH) 3 In a molar ratio of 1.1-2.5:1:3-3.8.
Furthermore, the reaction temperature of the step three is 300-450 ℃, the regeneration temperature of the regenerator is 400-500 ℃, and the reaction pressure is 0.01-1MPa.
The other technical scheme of the invention is as follows: a device for utilizing a pyridine base synthesis method comprises a reactor, a regenerator, a gas-solid separator, an evaporator, a heat exchanger, a centrifugal extractor, an evaporative condenser and a rectifying tower, wherein the reactor is connected with the regenerator, the top of the regenerator is provided with the gas-solid separator, the gas-solid separator is connected with the evaporative condenser, the evaporative condenser is connected with the heat exchanger, the heat exchanger is connected with the centrifugal extractor, the centrifugal extractor is connected with the evaporative condenser, the evaporative condenser is connected with the rectifying tower, and the evaporative condenser is also connected with a storage tank.
Further, the inside of reactor is equipped with two-layer distributor, and the bottom of reactor sets up the inlet pipe, and the inlet pipe is the sleeve pipe, advances the pipe including outer ammonia and the mixed aldehyde of inlayer advances the pipe.
Furthermore, the evaporator is of a steam drum type and is divided into an upper layer and a lower layer which are connected by a plurality of superconducting pipes.
Further, the rectifying tower is a falling film rectifying tower.
Further, the heat exchanger is also connected with a mixed aldehyde inlet pipe.
Compared with the prior art, the invention has the beneficial effects that:
1. the invention adopts the ZSM-5 molecular sieve loaded with the imidazole tetrafluoroborate as the catalyst for the first time, the catalyst can realize regeneration in the reaction process, the production efficiency is improved, and the pyridine base yield can reach more than 87%.
2. The invention changes the feeding mode of the raw materials, enables the raw materials to better participate in the reaction and reduces the occurrence of self-polymerization reaction.
3. The invention adopts a double-layer distributor, so that the catalyst is distributed more uniformly, and the coking phenomenon is obviously reduced.
4. The reaction heat of the invention can be recycled, steam is generated, and raw materials are heated at the same time, thus saving energy and lowering cost.
Drawings
FIG. 1 is a schematic structural diagram of a pyridine base synthesizing apparatus according to the present invention;
FIG. 2 is a schematic view of the structure of the reactor of the present invention.
In the figure: 1. a reactor; 11. a feed pipe; 111. ammonia gas inlet pipe; 112. feeding mixed aldehyde into a pipe; 2. a regenerator; 3. a gas-solid separator; 4. an evaporator; 5. a heat exchanger; 6. a centrifugal extractor; 7. an evaporative condenser; 8. a rectifying tower; 9. and (4) storage tank.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the 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.
Referring to fig. 1-2, a pyridine base synthesizing device comprises a reactor 1, a regenerator 2, a gas-solid separator 3, an evaporator 4, a heat exchanger 5, a centrifugal extractor 6, an evaporative condenser 7 and a rectifying tower 8, wherein the reactor 1 is connected with the regenerator 2, the top of the regenerator 2 is provided with the gas-solid separator 3, the gas-solid separator 3 is connected with the evaporative condenser 7, the evaporative condenser 7 is connected with the heat exchanger 5, the heat exchanger 5 is connected with the centrifugal extractor 6, the centrifugal extractor 6 is connected with the evaporative condenser 7, the evaporative condenser 7 is connected with the rectifying tower 8, and the evaporative condenser 7 is further connected with a storage tank 9. The inside of reactor 1 is equipped with two-layer distributor, and the bottom of reactor 1 sets up inlet pipe 11, and inlet pipe 11 is the sleeve pipe, advances pipe 111 and the mixed aldehyde of inlayer and advances pipe 112 including outer ammonia, and ammonia advances pipe 111 from ammonia and gets into, and mixed aldehyde advances pipe 112 from mixed aldehyde and gets into. The evaporator 4 is of a steam drum type and is divided into an upper layer and a lower layer which are connected by a plurality of superconducting pipes. The rectifying tower 8 is a falling film rectifying tower. The heat exchanger 5 is also connected to the mixed aldehyde inlet pipe 112, which can be secured.
Example 1:
fixing a ZSM-5 molecular sieve loaded with 2% of ionic liquid on a distributor of a reactor 1, then activating for 2 hours at 300 ℃, after the activation is finished, heating the reactor 1 to 350 ℃, and increasing the pressure of the reactor 1 to 1MPa to obtain formaldehyde: acetaldehyde: the NH3 ratio is 1.1.
Example 2:
fixing a ZSM-5 molecular sieve loaded with 3% of ionic liquid on a distributor of a reactor 1, then activating for 2 hours at 350 ℃, after the activation is finished, heating the reactor 1 to 350 ℃, and reacting formaldehyde: acetaldehyde: the NH3 proportion is 2.
Example 3:
fixing a ZSM-5 molecular sieve loaded with 5% of ionic liquid on a distributor of a reactor 1, then activating for 2 hours at 350 ℃, after the activation is finished, heating the reactor 1 to 400 ℃, and reacting formaldehyde: acetaldehyde: the NH3 ratio is 2.
Example 4:
fixing a ZSM-5 molecular sieve loaded with 7% of ionic liquid on a distributor of a reactor 1, then activating for 2 hours at 350 ℃, after the activation is finished, heating the reactor 1 to 400 ℃, and reacting formaldehyde: acetaldehyde: the NH3 ratio is 2.
Example 5:
fixing a ZSM-5 molecular sieve loaded with 10% of ionic liquid on a distributor of a reactor 1, then activating for 2h at 330 ℃, after the activation is finished, heating the reactor 1 to 450 ℃, and reacting formaldehyde: acetaldehyde: the NH3 ratio is 2.2.
Example 6:
fixing a ZSM-5 molecular sieve loaded with 10% of ionic liquid on a distributor of a reactor 1, then activating for 2h at 330 ℃, after the activation is finished, heating the reactor 1 to 350 ℃, and reacting formaldehyde: acetaldehyde: the NH3 ratio is 2.5.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be able to cover the technical solutions and the inventive concepts of the present invention within the technical scope of the present invention.
Claims (4)
1. A synthetic method of pyridine base is characterized by comprising the following steps:
the method comprises the following steps: with formaldehyde, acetaldehyde and NH 3 Taking ZSM-5 molecular sieve loaded with ionic liquid as a catalyst to synthesize pyridine base, wherein the loaded ionic liquid is imidazole tetrafluoroborate;
step two: activating the catalyst: fixing the catalyst on a distributor of the reactor (1), and then introducing nitrogen to activate for 2-4h at 300-350 ℃;
step three: reaction: after activation, the temperature is raised to the reaction temperature, the mixed aldehyde is gasified and then enters a bottom catalyst bed layer of the reactor (1) through a bottom sleeve, and NH is introduced at the same time 3 Reacting, wherein reaction gas and a catalyst enter a regenerator (2) through the top of the reactor (1), after passing through a gas-solid separator (3), the reactor (1) enters a post-treatment process, the catalyst is regenerated in the regenerator (2), and the regenerated catalyst enters the reactor (1) for continuous reaction;
step four: cooling: the reaction gas from the reactor (1) enters an evaporator (4) after passing through a regenerator (2) and a gas-solid separator (3), then enters a heat exchanger (5) for condensation, the evaporator (4) generates steam, and the heat exchanger (5) is connected with a mixed aldehyde inlet pipe (112) to heat the raw material;
step five: separation: and (3) feeding the product from the heat exchanger (5) into a centrifugal extractor (6), an evaporative condenser (7) and a rectifying tower (8) to separate the pyridine base product.
2. The pyridine base synthesis method according to claim 1, wherein the content of the imidazole tetrafluoroborate in the catalyst is 0.1-10%.
3. A process for the synthesis of pyridine base according to claim 1, characterized in that said formaldehyde: acetaldehyde: NH (NH) 3 In a molar ratio of 1.1-2.5:1:3-3.8.
4. The method for synthesizing pyridine base according to claim 1, wherein the reaction temperature of step three is 300-450 ℃, the regeneration temperature of the regenerator (2) is 400-500 ℃, and the reaction pressure is 0.01-1MPa.
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| CN202111387435.2A CN113893785B (en) | 2021-11-22 | 2021-11-22 | Pyridine base synthesis method and device |
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| CN202111387435.2A CN113893785B (en) | 2021-11-22 | 2021-11-22 | Pyridine base synthesis method and device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH0692369B2 (en) * | 1986-11-29 | 1994-11-16 | 広栄化学工業株式会社 | Method for producing pyridine bases |
| CN106117121A (en) * | 2016-08-17 | 2016-11-16 | 南京红太阳生物化学有限责任公司 | A kind of device and method of synthesis 2,2 bipyridyls |
| CN210057831U (en) * | 2019-05-31 | 2020-02-14 | 安徽国星生物化学有限公司 | Device for utilizing waste heat of tail gas generated in synthesis of alkylpyridine |
| CN111253229B (en) * | 2020-03-31 | 2022-08-30 | 山东明化新材料有限公司 | Formaldehyde pyridine hydrogen peroxide coproduction method |
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