CN110026146B - Device and method for preparing benzaldehyde by impinging stream rotating packed bed - Google Patents
Device and method for preparing benzaldehyde by impinging stream rotating packed bed Download PDFInfo
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- CN110026146B CN110026146B CN201910191824.4A CN201910191824A CN110026146B CN 110026146 B CN110026146 B CN 110026146B CN 201910191824 A CN201910191824 A CN 201910191824A CN 110026146 B CN110026146 B CN 110026146B
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- B01J4/00—Feed or outlet devices; Feed or outlet control devices
- B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
- B01J4/002—Nozzle-type elements
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J4/00—Feed or outlet devices; Feed or outlet control devices
- B01J4/02—Feed or outlet devices; Feed or outlet control devices for feeding measured, i.e. prescribed quantities of reagents
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
Abstract
A device and a method for preparing benzaldehyde by an impinging stream rotating packed bed belong to the technical field of fine chemical engineering and can solve the problems of harsh reaction conditions, multiple synthesis steps, low yield, high energy consumption cost and low quality of benzaldehyde products in the existing synthesis of benzaldehyde compounds.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a device and a method for preparing benzaldehyde by an impinging stream rotating packed bed.
Background
Benzaldehyde compounds are important organic synthesis intermediates and fine chemical products, and are widely applied to industries such as medicines, dyes, spices, resins and the like. At present, the method for synthesizing benzaldehyde compounds mainly comprises a benzyl chloride hydrolysis method and a toluene liquid-phase air oxidation method, and the two methods have the defects of harsh reaction conditions, low yield, more byproducts and the like.
Aiming at the defects of the traditional method for synthesizing benzaldehyde. In recent years, a plurality of scholars report researches on the synthesis of benzaldehyde by oxidizing benzyl alcohol, and the method has the advantages of simple process, environmental friendliness, good quality of benzaldehyde, no chlorine and the like, and is a novel green process for producing benzaldehyde. Master research student's position of Nanjing university of teacherIn the article "research on selective oxidation of benzyl alcohol catalyzed by polyoxometallate", a polyoxometallate [ TEAH ] is disclosed]H2PW12O40As a catalyst, a method for oxidizing benzyl alcohol by hydrogen peroxide. Master academic paper of Wuhan engineering university "aluminum-containing auxiliary agent pair Fe3O4In the study on the influence of the selective oxidation of benzyl alcohol, Fe is disclosed3O4Magnetic microspheres and modified Fe3O4Application thereof to catalysis of H2O2And selectively oxidizing the benzyl alcohol to prepare benzaldehyde. The university of Zhejiang Shuoshi academic paper "Green catalytic Process research for preparing benzaldehyde by oxidative dehydrogenation of benzyl alcohol", discloses a method for preparing benzaldehyde by using SBA-15-NH2-Au-Pd is used as a catalyst, tert-butyl hydroperoxide (TBHP) is used as an oxidant, and benzyl alcohol is oxidized to prepare benzaldehyde. The high-strength reports that benzyl alcohol is catalyzed by tetrabutylammonium bromide, sodium hypochlorite is used as an oxidant, and the method for synthesizing benzaldehyde by using ultrasonic-enhanced benzyl alcohol (high-strength reports, research on synthesizing benzaldehyde by ultrasonic-enhanced benzyl alcohol, and modern chemical engineering, 2018,38(6) 97-100) is characterized in that under the assistance of ultrasonic, a heterogeneous reaction interface is increased and is rapidly updated, so that benzaldehyde is synthesized by enhanced reaction, but the defect is that the product benzaldehyde contains a small amount of residual catalyst, so that the application of benzaldehyde in medicine synthesis is influenced. Therefore, the development of a benzaldehyde synthesis technology which has the advantages of simple process, environmental friendliness and no chlorine or other impurities in the product becomes a new field for green synthesis of benzaldehyde.
Disclosure of Invention
The invention provides a device and a method for preparing benzaldehyde by an impinging stream rotating packed bed, aiming at the problems of harsh reaction conditions, multiple synthesis steps, low yield, higher energy consumption and cost and low quality of benzaldehyde products in the existing synthesis of benzaldehyde compounds.
The invention adopts the following technical scheme:
a device for preparing benzaldehyde by using an impinging stream rotary packed bed comprises an impinging stream rotary packed bed, a liquid storage tank I, a liquid storage tank II and a liquid storage tank III, wherein the liquid storage tank II and the liquid storage tank III are provided with stirring rods, two sides of the impinging stream rotary packed bed are respectively provided with a liquid inlet I and a liquid inlet II which are opposite, packing is arranged in the middle of the impinging stream rotary packed bed, a liquid outlet is arranged at the bottom of the impinging stream rotary packed bed, the liquid inlet I of the impinging stream rotary packed bed is connected with the liquid outlet of the liquid storage tank I through a pipeline I which is sequentially provided with a liquid flowmeter I, a valve I and a pump I, the liquid inlet II of the impinging stream rotary packed bed is connected with the liquid outlet of the liquid storage tank III through a pipeline II which is sequentially provided with a liquid flowmeter II, a valve IV and a pump IV, the liquid outlet of the impinging stream rotary packed bed, pipeline IV is located between liquid flow meter I and valve I with the link of pipeline I, is equipped with pump II and valve II on the pipeline IV in proper order, and liquid outlet II is connected with pipeline II through pipeline V, and pipeline V is located between liquid flow meter II and the valve IV with the link of pipeline II, is equipped with pump III and valve III on the pipeline V in proper order.
A method for preparing benzaldehyde by using an impinging stream rotating packed bed device comprises the following steps:
firstly, dissolving benzyl alcohol in a reaction solvent at room temperature, placing the benzyl alcohol in a liquid storage tank I, placing a sodium hypochlorite solution in a liquid storage tank III, opening a valve I and a valve IV, closing a valve II and a valve III, opening a pump I and a pump IV, closing a pump II and a pump III, setting a liquid flow meter I and a liquid flow meter II to be equal, respectively ejecting reaction materials in the liquid storage tank I and the liquid storage tank III through opposite nozzles of a liquid distributor of an impinging stream rotating packed bed to form jet flow, and forming a fan-shaped film fog surface vertical to the jet flow direction after opposite impact is generated, wherein two reaction materials are mixed and reacted for the first time in the process;
secondly, after the reaction materials are subjected to the first mixing reaction, the reaction materials enter an inner cavity of the impinging stream rotating packed bed, flow to the outer edge along the pores of the packing of the impinging stream rotating packed bed under the action of centrifugal force, and the liquid is cut into liquid drops, liquid threads and a liquid film by the packing during the process, so that the second mixing reaction is completed;
thirdly, after the reaction materials are mixed for the second time, the reaction liquid is thrown onto the shell from the outer edge of the filler under the action of centrifugal force, and is converged and flows into the liquid storage tank II under the action of gravity, when the reaction materials in the liquid storage tank I and the liquid storage tank III all flow into the liquid storage tank II, the pump I, the pump IV, the valve I and the valve IV are closed, the valve II, the valve III, the pump II and the pump III are opened at the same time, the stirring rod of the liquid storage tank II is started, the reaction materials enter the impinging stream rotating filler bed again, and after the reaction is finished after the reaction is circulated for 120-180 min in sequence;
fourthly, extracting and separating an organic phase from the finally obtained reaction liquid, and removing a reaction solvent through a rotary evaporator to obtain a benzaldehyde crude product;
and fifthly, performing silica gel column chromatography on the benzaldehyde crude product to obtain benzaldehyde.
In the first step, the molar ratio of the benzyl alcohol to the sodium hypochlorite is 1: 1-5, the volume ratio of the reaction solvent to the sodium hypochlorite solution is 1:1, and the rotating speed of the rotating packed bed is 300-800 rpm.
In the first step, the reaction solvent is ethyl acetate or dichloromethane.
And in the fifth step, the eluent for silica gel chromatography is petroleum ether and ethyl acetate in a volume ratio of 5: 1.
The invention has the following beneficial effects:
the invention synthesizes the target product by means of the impinging stream-rotating packed bed, and the reaction system is a heterogeneous system, which seriously hinders the reaction and causes the defects of prolonged reaction time, low yield, high cost and the like. The impact flow-rotating packed bed is used for violently shearing and crushing the fluid to generate a huge and rapidly updated phase interface, so that the micromixing and mass transfer processes are greatly enhanced, the reaction rate is accelerated, and the method has the advantages of simple operation, high yield, mild reaction conditions, easy industrialization and the like.
Drawings
FIG. 1 is a schematic structural diagram of an apparatus for preparing benzaldehyde by using an impinging stream rotating packed bed according to the present invention;
FIG. 2 is a schematic diagram of the reaction of the present invention;
FIG. 3 is a hydrogen spectrum of benzaldehyde prepared according to the present invention;
wherein: 1-impinging stream rotating packed bed; 2-liquid storage tank I; 3-a stirring rod; 4-reservoir II; 5-reservoir III; 6-liquid inlet I; 7-liquid inlet II; 8-a filler; 9-a liquid outlet; 10-liquid flowmeter I; 11-valve I; 12-pump I; 13-pipeline I; 14-liquid flowmeter II; 15-valve iv; 16-pump IV; 17-line II; 18-line III; 19-line iv; 20-pump II; 21-valve II; 22-conduit V; 23-pump III; 24-valve III.
Detailed Description
Example 1
Adding 5.41 g (0.05 mol) of benzyl alcohol into a liquid storage tank I in sequence to be dissolved in 500mL of ethyl acetate, diluting a sodium hypochlorite solution (0.05 mol) to 500mL, placing the diluted sodium hypochlorite solution in a liquid storage tank III, setting the rotating speed of a rotating packed bed to be 300rpm, setting the flow rate to be 100L/h, opening a valve I and a valve IV, closing a valve II and a valve III, opening a pump I and a pump IV, closing a pump II and a pump III, immediately closing the pump I and the pump IV and the valve I and the valve IV when reaction liquid of the liquid storage tank I and the liquid storage tank III completely flows into a liquid storage tank II through an impinging stream rotating packed bed, simultaneously opening the valve II and the valve III and the pump II and the pump III, starting mechanical stirring of the liquid storage tank II, enabling reaction materials to pass through the impinging stream rotating packed bed again, introducing the reaction liquid into the liquid storage tank II, circularly conveying the reaction liquid into the impinging stream rotating, extraction with ethyl acetate, combination of the organic phases, drying over anhydrous sodium sulfate, evaporation of the solvent and column chromatography (eluent petroleum ether: ethyl acetate =5: 1) gave 0.63 g of benzaldehyde in 12% yield.
1H NMR(600 MHz, CDCl3) δ 10.02 (s, 1H), 7.88 (d, J = 12 Hz, 2H), 7.63 (t, J = 6 Hz, 1H), 7.53 (t, J = 6 Hz, 2H)。
Example 2
Adding 5.41 g (0.05 mol) of benzyl alcohol into a liquid storage tank I in turn to be dissolved in 500mL of ethyl acetate, diluting a sodium hypochlorite solution (0.15 mol) to 500mL and placing the solution in a liquid storage tank III, setting the rotating speed of a rotating packed bed to be 500rpm, setting the flow rate to be 100L/h, opening a valve I and a valve IV, closing a valve II and a valve III, opening a pump I and a pump IV, closing a pump II and a pump III, immediately closing the pump I and the pump IV and the valve I and the valve IV when reaction liquid of the liquid storage tank I and the liquid storage tank III completely flows into the liquid storage tank II through an impinging stream rotating packed bed, simultaneously opening the valve II and the valve III and the pump II and the pump III, starting mechanical stirring of the liquid storage tank II, enabling reaction materials to pass through the impinging stream rotating packed bed again, introducing the reaction liquid into the liquid storage tank II, circularly conveying the reaction liquid into the impinging stream rotating bed, reacting, extraction with ethyl acetate, combination of the organic phases, drying over anhydrous sodium sulfate, evaporation of the solvent and column chromatography (eluent petroleum ether: ethyl acetate =5: 1) gave 2.18 g of benzaldehyde in 41% yield.
1H NMR(600 MHz, CDCl3) δ 10.02 (s, 1H), 7.88 (d, J = 12 Hz, 2H), 7.63 (t, J = 6 Hz, 1H), 7.53 (t, J = 6 Hz, 2H)。
Example 3
Adding 5.41 g (0.05 mol) of benzyl alcohol into a liquid storage tank I in turn to be dissolved in 500mL of ethyl acetate, diluting a sodium hypochlorite solution (0.25 mol) to 500mL, placing the diluted sodium hypochlorite solution in a liquid storage tank III, setting the rotating speed of a rotating packed bed to be 800rpm, setting the flow rate to be 100L/h, opening a valve I and a valve IV, closing a valve II and a valve III, opening a pump I and a pump IV, closing a pump II and a pump III, immediately closing the pump I and the pump IV and the valve I and the valve IV when reaction liquid of the liquid storage tank I and the liquid storage tank III completely flows into a liquid storage tank II through an impinging stream rotating packed bed, simultaneously opening the valve II and the valve III and the pump II and the pump III, starting mechanical stirring of the liquid storage tank II, enabling reaction materials to pass through the impinging stream rotating packed bed again, introducing the reaction liquid into the liquid storage tank II, circularly conveying the reaction liquid into the impinging stream rotating, extraction with ethyl acetate, combination of the organic phases, drying over anhydrous sodium sulfate, evaporation of the solvent and column chromatography (eluent petroleum ether: ethyl acetate =5: 1) gave 4.4g of benzaldehyde in 82% yield.
1H NMR(600 MHz, CDCl3) δ 10.02 (s, 1H), 7.88 (d, J = 12 Hz, 2H), 7.63 (t, J = 6 Hz, 1H), 7.53 (t, J = 6 Hz, 2H)。
Example 4
Adding 5.41 g (0.05 mol) of benzyl alcohol into a liquid storage tank I in turn to be dissolved in 500mL of dichloromethane, diluting a sodium hypochlorite solution (0.25 mol) to 500mL, placing the diluted solution in a liquid storage tank III, setting the rotating speed of a rotating packed bed to be 800rpm and the flow rate to be 100L/h, opening a valve I and a valve IV, closing a valve II and a valve III, opening a pump I and a pump IV, closing a pump II and a pump III, immediately closing the pump I and the pump IV and the valve I and the valve IV when reaction liquid of the liquid storage tank I and the liquid storage tank III completely flows into a liquid storage tank II through an impinging stream rotating packed bed, simultaneously opening the valve II and the valve III and the pump II and the pump III, starting mechanical stirring of the liquid storage tank II, enabling reaction materials to pass through the impinging stream rotating packed bed again, introducing the reaction liquid into the liquid storage tank II, circularly conveying the reaction liquid into the impinging stream rotating packed bed in, extraction with ethyl acetate, combination of the organic phases, drying over anhydrous sodium sulfate, evaporation of the solvent and column chromatography (eluent petroleum ether: ethyl acetate =5: 1) gave 3.95 g of benzaldehyde in 75% yield.
1H NMR(600 MHz, CDCl3) δ 10.02 (s, 1H), 7.88 (d, J = 12 Hz, 2H), 7.63 (t, J = 6 Hz, 1H), 7.53 (t, J = 6 Hz, 2H)。
Claims (4)
1. A device used in the method comprises an impinging stream rotating packed bed (1), a liquid storage tank I (2), a liquid storage tank II (4) and a liquid storage tank III (5) which are provided with stirring rods (3), wherein two sides of the impinging stream rotating packed bed (1) are respectively provided with a liquid inlet I (6) and a liquid inlet II (7) which are opposite, the middle of the impinging stream rotating packed bed (1) is provided with a packing (8), the bottom of the impinging stream rotating packed bed is provided with a liquid outlet (9), the liquid inlet I (6) of the impinging stream rotating packed bed (1) is connected with the liquid outlet of the liquid storage tank I (2) through a pipeline I (13) which is sequentially provided with a liquid flow meter I (10), a valve I (11) and a pump I (12), the liquid inlet II (7) of the impinging stream rotating packed bed (1) is connected with the liquid outlet (9) of the liquid storage tank (5) through a pipeline II (17) which is sequentially provided with a liquid flow meter II (14), a valve IV (15, a liquid outlet (9) of the impinging stream rotating packed bed (1) is connected with a liquid inlet of a liquid storage tank II (4) through a pipeline III (18), a liquid outlet I and a liquid outlet II are respectively arranged on two sides of the liquid storage tank II (4), the liquid outlet I is connected with a pipeline I (13) through a pipeline IV (19), the connecting end of the pipeline IV (19) and the pipeline I (13) is positioned between a liquid flowmeter I (10) and a valve I (11), a pump II (20) and a valve II (21) are sequentially arranged on the pipeline IV (19), the liquid outlet II is connected with a pipeline II (17) through a pipeline V (22), the connecting end of the pipeline V (22) and the pipeline II (17) is positioned between a liquid flowmeter II (14) and a valve IV (15), and a pump III (23) and a valve III (24) are sequentially arranged on the pipeline V (22);
the method is characterized in that: the method comprises the following steps:
firstly, dissolving benzyl alcohol in a reaction solvent at room temperature, placing the benzyl alcohol in a liquid storage tank I (2), placing a sodium hypochlorite solution in a liquid storage tank III (5), opening a valve I (11) and a valve IV (15), closing a valve II (21) and a valve III (24), opening a pump I (12) and a pump IV (16), closing a pump II (20) and a pump III (23), setting a liquid flowmeter I (10) and a liquid flowmeter II (14) to be equal, and impacting reaction materials in the liquid storage tank I (2) and the liquid storage tank III (5) oppositely through a nozzle of a liquid distributor of an impact flow rotating packed bed (1) to complete a first mixing reaction;
secondly, after the reaction materials are subjected to the first mixing reaction, the reaction materials enter an inner cavity of the impinging stream rotating packed bed (1) and flow to the outer edge along the pores of the filler (8) of the impinging stream rotating packed bed (1) under the action of centrifugal force, so that the second mixing reaction is finished;
thirdly, after mixing the reaction materials for the second time, flowing the reaction materials into a liquid storage tank II (4), when the reaction materials in a liquid storage tank I (2) and a liquid storage tank III (5) all flow into the liquid storage tank II (4), closing a pump I (12), a pump IV (16), a valve I (11) and a valve IV (15), simultaneously opening a valve II (21), a valve III (24), a pump II (20) and a pump III (23), starting a stirring rod of the liquid storage tank II (4), enabling the reaction materials to enter the impinging stream rotating packed bed (1) again, and after circulating for 120-180 min in sequence, finishing the reaction;
fourthly, extracting and separating an organic phase from the finally obtained reaction liquid, and removing a reaction solvent through a rotary evaporator to obtain a benzaldehyde crude product;
and fifthly, performing silica gel column chromatography on the benzaldehyde crude product to obtain benzaldehyde.
2. The method for preparing benzaldehyde by using an impinging stream rotating packed bed according to claim 1, wherein: in the first step, the molar ratio of the benzyl alcohol to the sodium hypochlorite is 1: 1-5, the volume ratio of the reaction solvent to the sodium hypochlorite solution is 1:1, and the rotating speed of the rotating packed bed is 300-800 rpm.
3. The method for preparing benzaldehyde by using an impinging stream rotating packed bed according to claim 1, wherein: in the first step, the reaction solvent is ethyl acetate or dichloromethane.
4. The method for preparing benzaldehyde by using an impinging stream rotating packed bed according to claim 1, wherein: and in the fifth step, the eluent for the silica gel column chromatography is petroleum ether and ethyl acetate in a volume ratio of 5: 1.
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| CN112479340A (en) * | 2019-09-11 | 2021-03-12 | 南京延长反应技术研究院有限公司 | Wet oxidation treatment system and method for industrial wastewater |
| CN111170838B (en) * | 2020-01-14 | 2023-04-14 | 中北大学 | Method and reaction device for preparing benzaldehyde by supergravity ozone oxidation of styrene |
| CN113603597B (en) * | 2021-08-13 | 2023-02-03 | 中山大学 | Method for preparing benzyl aldehyde by quickly oxidizing benzyl alcohol |
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| US20100107474A1 (en) * | 2008-10-31 | 2010-05-06 | Mahesh Talwar | Apparatus and method for Rapid Biodiesel Fuel Production |
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