CN110026146A - A kind of rotary packed bed device and method for preparing benzaldehyde of percussion flow - Google Patents
A kind of rotary packed bed device and method for preparing benzaldehyde of percussion flow Download PDFInfo
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- CN110026146A CN110026146A CN201910191824.4A CN201910191824A CN110026146A CN 110026146 A CN110026146 A CN 110026146A CN 201910191824 A CN201910191824 A CN 201910191824A CN 110026146 A CN110026146 A CN 110026146A
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
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Abstract
A kind of rotary packed bed device and method for preparing benzaldehyde of percussion flow, belong to technical field of fine, it can solve severe reaction conditions present in existing synthesizing benzaldehyde class compound, synthesis step is more, low yield, energy consumption cost is higher, the not high problem of benzaldehyde product quality, it is rotary packed bed including percussion flow, reservoir I, reservoir II and reservoir III equipped with stirring rod, fluid is acutely sheared and is crushed using Impinging Stream-Rotating Packed Bed, generate phase interface that is huge and quickly updating, so that microcosmic mixing and mass transport process have obtained great reinforcing, accelerate reaction rate, the present invention has easy to operate, high income, reaction condition is mild and is easy to the advantages that industrializing.
Description
Technical field
The invention belongs to technical field of fine, and in particular to a kind of rotary packed bed dress for preparing benzaldehyde of percussion flow
It sets and method.
Background technique
Compound of benzaldehyde category is a kind of important organic synthesis intermediate and fine chemical product, is widely used in doctor
The industries such as medicine, dyestuff, fragrance, resin.Currently, the method for synthesizing benzaldehyde class compound mainly has benzyl chloride Hydrolyze method and toluene
Liquid-phase air oxidation, both methods the disadvantages of there are severe reaction conditions, low yield, more by-products.
For the method for conventional synthesis benzaldehyde, there are many deficiencies.In recent years, many scholars report benzyl alcohol oxygen
It is combined to the research of benzaldehyde, this method has many advantages, such as that simple process, environmental-friendly, benzaldehyde is high-quality and is free of chlorine, is
A kind of technique of novel green production benzaldehyde.Nanjing Normal University's Master degree candidate's academic dissertation " urge by polyoxometallate
The research of the benzyl alcohol Selective Oxidation of change " in, one kind is disclosed in polyoxometallate [TEAH] H2PW12O40As catalysis
Agent, the method for hydrogen peroxide oxidation benzyl alcohol." auxiliary agent containing aluminium is to Fe for Wuhan Engineering Univ's master thesis3O4Catalytic phenylmethanol choosing
The influence research of selecting property oxidation " in, disclose Fe3O4Magnetic microsphere and modified Fe3O4, it is applied to catalysis H2O2Selectivity
Oxybenzene methyl alcohol prepares benzaldehyde.Zhejiang University's master thesis " benzyl alcohol oxidation dehydrogenation producing benzaldehyde green catalysis technique
Research " in, it discloses a kind of using SBA-15-NH2- Au-Pd is used as catalyst, is oxidation with tert-butyl hydroperoxide (TBHP)
Agent, the method that Oxybenzene methyl alcohol prepares benzaldehyde.High text is strong to wait report benzyl alcohol under tetrabutylammonium bromide catalysis, with hypochlorous acid
Sodium is as oxidant, and using the method for ultrasound-enhanced benzyl alcohol synthesizing benzaldehyde, (high text is strong etc., and ultrasound-enhanced benzyl alcohol synthesizes benzene
The research of formaldehyde, modern chemical industry, 2018,38 (6) 97 ~ 100), this technology is to increase heterogeneous reaction under ultrasonic wave added
Interface simultaneously updates reaction interface rapidly, thus strengthen reaction synthesizing benzaldehyde, but shortcoming is contained in product benzaldehyde
There is a small amount of remaining catalyst, is applied in medicine synthesis to influence benzaldehyde.Therefore, exploitation has simple process, ring
The benzaldehyde synthetic technology of border close friend, product without chlorine and other impurity, it has also become the frontier of green syt benzaldehyde.
Summary of the invention
The present invention is for severe reaction conditions present in existing synthesizing benzaldehyde class compound, and synthesis step is more, yield
Problem low, that energy consumption cost is higher, benzaldehyde product quality is not high provides a kind of percussion flow the rotary packed bed benzaldehyde for preparing
Device and method, the preparation method do not need catalyst, have simple process, yield is high, the few advantage of by-product.
The present invention adopts the following technical scheme:
A kind of rotary packed bed device for preparing benzaldehyde of percussion flow, including percussion flow is rotary packed bed, reservoir I, equipped with stirring
The reservoir II and reservoir III of stick are mixed, the rotary packed bed two sides of percussion flow are respectively equipped with opposite inlet I and inlet
II, the rotary packed bed centre of percussion flow is equipped with filler, and bottom is equipped with liquid outlet, and the rotary packed bed inlet I of percussion flow passes through
The pipeline I for being successively arranged fluid flowmeter I, valve I and pump I is connect with the liquid outlet of reservoir I, and percussion flow is rotary packed bed
Inlet II is connect by being successively arranged the pipeline II of fluid flowmeter II, valve IV and pump IV with the liquid outlet of reservoir III,
The rotary packed bed liquid outlet of percussion flow is connect by pipeline III with the inlet of reservoir II, and the two sides of reservoir II are set respectively
There are liquid outlet I and liquid outlet II, liquid outlet I is connect by pipeline IV with pipeline I, and the connecting pin of pipeline IV and pipeline I is located at liquid
Between flowmeter body I and valve I, pump II and valve II are successively arranged on pipeline IV, liquid outlet II passes through pipeline V and pipeline II
The connecting pin of connection, pipeline V and pipeline II is successively arranged pump III between fluid flowmeter II and valve IV on pipeline V
With valve III.
A method of benzaldehyde being prepared using the rotary packed bed device for preparing benzaldehyde of percussion flow, including is walked as follows
It is rapid:
Benzyl alcohol is dissolved in reaction dissolvent by the first step at room temperature, is placed in reservoir I, liquor natrii hypochloritis is set
In reservoir III, valve I and valve IV are opened, closes valve II and valve III, opens pump I and pump IV, closes pump II and pump III,
Fluid flowmeter I is set and fluid flowmeter II is equal, the reaction mass in reservoir I and reservoir III passes through percussion flow respectively
The opposite nozzle of rotary packed bed liquid distribution trough sprays to form jet stream, and is formed after opposite hit occurs perpendicular to jet stream
The fan-shaped membrane cloudy surface in direction, in the process, two strands of reaction masses realize mixing for the first time, reaction；
Second step, after reaction mass first time hybrid reaction, the inner cavity rotary packed bed into percussion flow, in the effect of centrifugal force
The hole of the lower filler rotary packed bed along percussion flow is flowed to outer rim, and liquid by filler is cut into drop, liquid during this period
Silk, liquid film complete second of hybrid reaction；
Third step, after second of reaction mass mixes, reaction solution is thrown on shell from the outer rim of filler under the influence of centrifugal force,
Convergence flows into reservoir II under the effect of gravity, when the reaction mass in reservoir I and reservoir III all flows into reservoir
When in II, pump I and pump IV and valve I and valve IV are closed, opens simultaneously valve II and valve III and pump II and pump III, and
Start the stirring rod of reservoir II, it is rotary packed bed that reaction mass is again introduced into percussion flow, after circuiting sequentially 120 ~ 180min, instead
It should terminate；
4th step removes reaction dissolvent through Rotary Evaporators, obtains benzene by the reaction solution finally obtained through extraction and separation organic phase
Formaldehyde crude product；
5th step obtains benzaldehyde by benzaldehyde crude product through silica gel column chromatography.
Benzyl alcohol described in the first step is 1:1 ~ 5, reaction dissolvent and liquor natrii hypochloritis with the molar ratio with sodium hypochlorite
Volume ratio be 1:1, rotary packed bed revolving speed be 300 ~ 800rpm.
Reaction dissolvent described in the first step is ethyl acetate or methylene chloride.
The eluant, eluent of silica gel column chromatography described in 5th step is the petroleum ether and ethyl acetate of volume ratio 5:1.
Beneficial effects of the present invention are as follows:
The present invention synthesizes target product by Impinging Stream-Rotating Packed Bed, since reaction system is heterogeneous system, this serious resistance
Hindered reaction carry out, cause the reaction time to extend, yield is low, it is at high cost the disadvantages of.Using Impinging Stream-Rotating Packed Bed to fluid
It is acutely sheared and is crushed, generate phase interface that is huge and quickly updating, so that microcosmic mixing and mass transport process have obtained pole
Big reinforcing, accelerates reaction rate, and the present invention has easy to operate, high income, reaction condition mild and is easy to industrialize
The advantages that.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of the rotary packed bed device for preparing benzaldehyde of percussion flow of the present invention；
Fig. 2 is reaction principle figure of the present invention；
Fig. 3 is the hydrogen spectrogram of benzaldehyde prepared by the present invention；
Wherein: 1- percussion flow is rotary packed bed；2- reservoir I；3- stirring rod；4- reservoir II；5- reservoir III；6- inlet
Ⅰ；7- inlet II；8- filler；9- liquid outlet；10- fluid flowmeter I；11- valve I；12- pump I；13- pipeline I；14- liquid
Flow meter II；15- valve IV；16- pump IV；17- pipeline II；18- pipeline III；19- pipeline IV；20- pump II；21- valve II；
22- pipeline V；23- pump III；24- valve III.
Specific embodiment
Embodiment 1
5.41 g (0.05 mol) benzyl alcohol is sequentially added into reservoir I and is dissolved in 500 mL ethyl acetate, by sodium hypochlorite
Solution (0.05mol) is diluted to 500mL and is placed in reservoir III, sets rotary packed bed revolving speed as 300rpm, flow 100L/h,
Valve I and valve IV are opened, valve II and valve III are closed, opens pump I and pump IV, pump II and pump III are closed, when I He of reservoir
The reaction solution of reservoir III by the rotary packed bed whole of percussion flow be flowed into reservoir II when, immediately close off pump I and pump IV with
And valve I and valve IV, valve II and valve III and pump II and pump III are opened simultaneously, and the machinery for starting reservoir II stirs
It mixes, two strands of reaction masses are rotary packed bed through percussion flow again, and reaction solution is passed into reservoir II, and reaction solution is divided to two bursts of circulations
It during feeding percussion flow is rotary packed bed, after reacting 120 min, is extracted with ethyl acetate, merges organic phase, it is dry with anhydrous sodium sulfate
It is dry, solvent is boiled off, obtains 0.63 g of benzaldehyde through column chromatography for separation (eluent is petroleum ether: ethyl acetate=5:1), yield is
12%。
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)。
Embodiment 2
5.41 g (0.05 mol) benzyl alcohol is sequentially added into reservoir I and is dissolved in 500 mL ethyl acetate, by sodium hypochlorite
Solution (0.15mol) is diluted to 500mL and is placed in reservoir III, sets rotary packed bed revolving speed as 500rpm, flow 100L/h,
Valve I and valve IV are opened, valve II and valve III are closed, opens pump I and pump IV, pump II and pump III are closed, when I He of reservoir
The reaction solution of reservoir III by the rotary packed bed whole of percussion flow be flowed into reservoir II when, immediately close off pump I and pump IV with
And valve I and valve IV, valve II and valve III and pump II and pump III are opened simultaneously, and the machinery for starting reservoir II stirs
It mixes, two strands of reaction masses are rotary packed bed through percussion flow again, and reaction solution is passed into reservoir II, and reaction solution is divided to two bursts of circulations
It during feeding percussion flow is rotary packed bed, after reacting 160 min, is extracted with ethyl acetate, merges organic phase, it is dry with anhydrous sodium sulfate
It is dry, solvent is boiled off, obtains 2.18 g of benzaldehyde through column chromatography for separation (eluent is petroleum ether: ethyl acetate=5:1), yield is
41%。
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)。
Embodiment 3
5.41 g (0.05 mol) benzyl alcohol is sequentially added into reservoir I and is dissolved in 500 mL ethyl acetate, by sodium hypochlorite
Solution (0.25mol) is diluted to 500mL and is placed in reservoir III, sets rotary packed bed revolving speed as 800rpm, flow 100L/h,
Valve I and valve IV are opened, valve II and valve III are closed, opens pump I and pump IV, pump II and pump III are closed, when I He of reservoir
The reaction solution of reservoir III by the rotary packed bed whole of percussion flow be flowed into reservoir II when, immediately close off pump I and pump IV with
And valve I and valve IV, valve II and valve III and pump II and pump III are opened simultaneously, and the machinery for starting reservoir II stirs
It mixes, two strands of reaction masses are rotary packed bed through percussion flow again, and reaction solution is passed into reservoir II, and reaction solution is divided to two bursts of circulations
It during feeding percussion flow is rotary packed bed, after reacting 180 min, is extracted with ethyl acetate, merges organic phase, it is dry with anhydrous sodium sulfate
It is dry, solvent is boiled off, obtains benzaldehyde 4.4g through column chromatography for separation (eluent is petroleum ether: ethyl acetate=5:1), yield is
82%。
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)。
Embodiment 4
5.41 g (0.05 mol) benzyl alcohol is sequentially added into reservoir I and is dissolved in 500 mL methylene chloride, by sodium hypochlorite
Solution (0.25mol) is diluted to 500mL and is placed in reservoir III, sets rotary packed bed revolving speed as 800rpm, flow 100L/h,
Valve I and valve IV are opened, valve II and valve III are closed, opens pump I and pump IV, pump II and pump III are closed, when I He of reservoir
The reaction solution of reservoir III by the rotary packed bed whole of percussion flow be flowed into reservoir II when, immediately close off pump I and pump IV with
And valve I and valve IV, valve II and valve III and pump II and pump III are opened simultaneously, and the machinery for starting reservoir II stirs
It mixes, two strands of reaction masses are rotary packed bed through percussion flow again, and reaction solution is passed into reservoir II, and reaction solution is divided to two bursts of circulations
It during feeding percussion flow is rotary packed bed, after reacting 180 min, is extracted with ethyl acetate, merges organic phase, it is dry with anhydrous sodium sulfate
It is dry, solvent is boiled off, obtains 3.95 g of benzaldehyde through column chromatography for separation (eluent is petroleum ether: ethyl acetate=5:1), yield is
75%。
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 (5)
1. a kind of rotary packed bed device for preparing benzaldehyde of percussion flow, it is characterised in that: rotary packed bed including percussion flow
(1), reservoir I (2), reservoir II (4) and reservoir III (5) equipped with stirring rod (3), percussion flow rotary packed bed (1)
Two sides are respectively equipped with opposite inlet I (6) and inlet II (7), are equipped with filler (8) among percussion flow rotary packed bed (1),
Bottom is equipped with liquid outlet (9), the inlet I (6) of percussion flow rotary packed bed (1) by be successively arranged fluid flowmeter I (10),
Valve I (11) and pump I (12) pipeline I (13) connect with the liquid outlet of reservoir I (2), percussion flow rotary packed bed (1) into
Liquid mouth II (7) is by being successively arranged fluid flowmeter II (14), valve IV (15) and the pipeline II (17) and liquid storage that pump IV (16)
The liquid outlet (9) of slot III (5) connects, and the liquid outlet (9) of percussion flow rotary packed bed (1) passes through pipeline III (18) and reservoir II
(4) inlet connection, the two sides of reservoir II (4) are respectively equipped with liquid outlet I and liquid outlet II, and liquid outlet I passes through pipeline IV
(19) it is connect with pipeline I (13), the connecting pin of pipeline IV (19) and pipeline I (13) is located at fluid flowmeter I (10) and valve I
(11) between, pump II (20) and valve II (21) are successively arranged on pipeline IV (19), liquid outlet II passes through pipeline V (22) and pipe
Road II (17) connection, the connecting pin of pipeline V (22) and pipeline II (17) be located at fluid flowmeter II (14) and valve IV (19) it
Between, pump III (23) and valve III (24) are successively arranged on pipeline V (22).
2. a kind of method for preparing benzaldehyde using device as described in claim 1, characterized by the following steps:
Benzyl alcohol is dissolved in reaction dissolvent by the first step at room temperature, is placed in reservoir I (2), and sodium hypochlorite is molten
Liquid is placed in reservoir III (5), opens valve I (11) and valve IV (15), closes valve II (21) and valve III (24), opens pump
IV (16) of I (12) and pump close III (23) of II (20) of pump and pump, fluid flowmeter I (10) and fluid flowmeter II (14) are arranged
Equal, the reaction mass in reservoir I (2) and reservoir III (5) passes through the liquid distribution of percussion flow rotary packed bed (1) respectively
The nozzle of device is hit in opposite directions completes first time hybrid reaction；
Second step, after reaction mass first time hybrid reaction, into the inner cavity of percussion flow rotary packed bed (1), in centrifugal force
It is flowed along the hole of the filler (8) of percussion flow rotary packed bed (1) to outer rim under effect, completes second of hybrid reaction；
Third step flows into reservoir II (4), after second of reaction mass mixes when in reservoir I (2) and reservoir III (5)
Reaction mass when all flowing into reservoir II (4), close I (12) of pump and pump IV (16) and valve I (11) and valve IV
(15), valve II (21) and valve III (24) and II (20) of pump and III (23) of pump are opened simultaneously, and start reservoir II (4)
Stirring rod, reaction mass are again introduced into that percussion flow is rotary packed bed (1), and after circuiting sequentially 120 ~ 180min, reaction terminates；
4th step removes reaction dissolvent through Rotary Evaporators, obtains benzene by the reaction solution finally obtained through extraction and separation organic phase
Formaldehyde crude product；
5th step obtains benzaldehyde by benzaldehyde crude product through silica gel column chromatography.
3. a kind of rotary packed bed method for preparing benzaldehyde of percussion flow according to claim 2, it is characterised in that: first
Benzyl alcohol described in step be 1:1 ~ 5 with the molar ratio of sodium hypochlorite, the volume ratio of reaction dissolvent and liquor natrii hypochloritis are 1:
1, rotary packed bed revolving speed is 300 ~ 800rpm.
4. a kind of rotary packed bed method for preparing benzaldehyde of percussion flow according to claim 2, it is characterised in that: first
Reaction dissolvent described in step is ethyl acetate or methylene chloride.
5. a kind of rotary packed bed method for preparing benzaldehyde of percussion flow according to claim 2, it is characterised in that: the 5th
The eluant, eluent of silica gel column chromatography described in step is the petroleum ether and ethyl acetate of volume ratio 5:1.
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| CN201910191824.4A CN110026146B (en) | 2019-03-14 | 2019-03-14 | Device and method for preparing benzaldehyde by impinging stream rotating packed bed |
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| CN201910191824.4A CN110026146B (en) | 2019-03-14 | 2019-03-14 | Device and method for preparing benzaldehyde by impinging stream rotating packed bed |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111170838A (en) * | 2020-01-14 | 2020-05-19 | 中北大学 | Method and reaction device for preparing benzaldehyde by supergravity ozone oxidation of styrene |
| 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 |
| CN113603597A (en) * | 2021-08-13 | 2021-11-05 | 中山大学 | Method for preparing benzyl aldehyde by quickly oxidizing benzyl alcohol |
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| CN110026146B (en) | 2021-05-18 |
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