CN114733460A - High-flux low-energy-consumption tetracyclic heptane continuous flow synthesis device and method - Google Patents
High-flux low-energy-consumption tetracyclic heptane continuous flow synthesis device and method Download PDFInfo
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 19
- 238000005265 energy consumption Methods 0.000 title claims abstract description 19
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 10
- 239000012530 fluid Substances 0.000 claims abstract description 7
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 3
- 238000003475 lamination Methods 0.000 claims description 7
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000004812 Fluorinated ethylene propylene Substances 0.000 claims description 2
- 239000004813 Perfluoroalkoxy alkane Substances 0.000 claims description 2
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000010453 quartz Substances 0.000 claims description 2
- 238000002834 transmittance Methods 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims 3
- 238000000926 separation method Methods 0.000 abstract 1
- 238000006352 cycloaddition reaction Methods 0.000 description 4
- 208000017983 photosensitivity disease Diseases 0.000 description 4
- 231100000434 photosensitization Toxicity 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 230000003321 amplification Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000003199 nucleic acid amplification method Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 238000004146 energy storage Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/123—Ultraviolet light
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/31—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/86—Ring systems containing bridged rings containing four rings
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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
- Y02P20/10—Process efficiency
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Abstract
A high throughput low energy consumption tetracyclic heptane continuous flow synthesis apparatus, comprising: the fluid conveying device is used for conveying reaction raw materials; the capillary continuous flow reactor is used for reacting raw materials to generate tetracyclic heptane and is arranged between the high-power panel type UV-LED lamp and the reflector. The invention takes tetraethyl mikrolon as a photosensitizer, the tetraethyl mikrolon is dissolved in norbornadiene to form homogeneous reaction liquid, the homogeneous reaction liquid is irradiated and reacted by an ultraviolet light source in a capillary continuous flow reactor, and the tetracycloheptane is obtained after the rotary evaporation and separation of reaction products.
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to a high-flux low-energy-consumption tetracyclic heptane continuous flow synthesis device and a method.
Background
The tetracycloheptane is a product of a photosensitization cycloaddition reaction of norbornadiene under ultraviolet light, has a high-tension cage-shaped structure and higher density, is a high-efficiency rocket propellant and missile attitude control agent, can be used as an additive to improve the energy density of hydrocarbon fuels, is a good solar energy storage material, and has wide attention in the field of solar energy storage.
The traditional batch still type photoreactor has a plurality of limitations, particularly in the aspects of uneven light intensity distribution, difficult amplification, low light energy utilization efficiency and the like. Compared with a kettle type photoreactor, the photochemical microreactor has the advantages of large specific surface area, high mixing efficiency, high heat and mass transfer rate, uniform illumination, high safety performance, easy process amplification and the like, and provides a powerful platform for strengthening photochemical transformation and improving the process efficiency.
Patent CN111790335A discloses an ultraviolet photochemical reaction system based on continuous flow technology, which includes: a capillary continuous flow reactor, a flexible light source, and a blower, wherein: the flexible light source is wound on the outer wall of the container, the capillary reactor is wound on the outer side of the flexible light source and communicated with the air blower, and air is blown in through the air blower to cool the flexible light source and the capillary microreactor.
The existing ultraviolet photochemical reaction device adopts a low-pressure or medium-pressure mercury lamp as a light source, and the mercury lamp has the defects of high energy consumption, high temperature rise, need of external water cooling equipment and the like; in contrast, the ultraviolet LED lamp strip has the advantages of small heat release, strong monochromaticity of light, and the like, but the power and light intensity are low, and it is difficult to meet the requirement of high-throughput photochemical synthesis.
Disclosure of Invention
The invention aims to solve the problems and provide a high-throughput low-energy consumption tetracyclic heptane continuous flow synthesis device and a method.
The purpose of the invention is realized by the following technical scheme:
a high throughput low energy consumption tetracyclic heptane continuous flow synthesis apparatus, comprising:
the fluid conveying device is used for conveying reaction raw materials;
the capillary continuous flow reactor is used for reacting raw materials to generate tetracyclic heptane and is arranged between the high-power panel type UV-LED lamp and the reflector.
Further, the capillary continuous flow reactor is composed of capillary channels which are arranged in a serpentine and/or annular manner.
Further, the capillary channels are arranged in a laminating mode, and the number of laminated layers is 2-5.
Furthermore, the capillary continuous flow reactor is made of materials with the light transmittance higher than 80% in an ultraviolet region, and comprises quartz, glass, PFA, FEP and ETFE, the inner diameter of the capillary is 0.5-6 mm, and the wall thickness is 0.1-2 mm.
Furthermore, the maximum emission wavelength range of the high-power panel type UV-LED lamp is 315-400 nm, the half-peak width of emitted light is 5-20 nm, and the luminous power is 20-2000 mW/cm2Radiation window at 150cm2～3000cm2The input power is between 200W and 2000W.
Furthermore, the reflectors or other light reflecting fittings are arranged below and around the high-power panel type UV-LED lamp.
Further, the high-power panel type UV-LED lamps are connected with the capillary continuous flow reactor in parallel, and the number of the parallel connection is 2-10.
Further, dissolving a photosensitizer tetraethyl mikrolon in norbornadiene to form homogeneous reaction liquid;
sending the reaction liquid to a capillary continuous flow reactor through a fluid conveying device;
irradiating the reaction product in a capillary continuous flow reactor by an ultraviolet light source, and separating the reaction product by rotary evaporation to obtain the tetracyclic heptane.
Further, the mass fraction range of the tetraethyl ketone is 0.01-5%.
Further, the reaction temperature is 0-50 ℃ and the reaction time is 5-60 min during the irradiation reaction.
Further, the fluid conveying device comprises a fluid conveying device such as an advection pump or an injection pump, reactants are injected, and the flow speed of liquid in the capillary is preferably 0.1-500 ml/min.
Compared with the prior art, the invention has the following beneficial effects:
the invention uses the high-power panel type UV-LED lamp without an additional water cooling device, reduces energy consumption and ensures high light power, uses the capillary reaction channel to effectively improve the surface area of unit reactant volume receiving illumination radiation, adopts a lamination method and a reflector to improve the utilization rate of light energy and reduce unit energy consumption. The method can realize high-flux production of the tetracycloheptane, shortens the reaction time to 5-60 min, and has the yield of over 98 percent. The flux can be further improved by adopting a parallel amplification technology, and data obtained in a laboratory can be directly used for industrial production.
Drawings
FIG. 1 is a front sectional view of a tetracycloheptane continuous flow synthesis apparatus according to the present invention;
FIG. 2 is a layout of capillaries according to the present invention;
FIG. 3 is a nuclear magnetic spectrum of tetracycloheptane prepared in the example;
in the figure: 1-high-power panel type UV-LED lamp; 2-a capillary continuous flow reactor with a serpentine arrangement; 3-arranging laminated capillaries in a serpentine shape; 4-annularly arranging a capillary continuous flow reactor; 5-annularly arranging the laminated capillaries; 6-a reflector.
Detailed Description
The invention is described in detail below with reference to the figures and specific embodiments.
Example 1
As shown in fig. 1 and fig. 2, the tetracyclic heptane continuous flow synthesis apparatus of the embodiment includes a capillary continuous flow reactor 2 with serpentine arrangement formed by a stacked capillary 3 with serpentine arrangement, and a capillary continuous flow reactor 4 with annular arrangement formed by a stacked capillary 5 with annular arrangement, wherein a high-power panel UV-LED lamp 1 is disposed at the upper part of the capillary continuous flow reactor 2 with serpentine arrangement and the capillary continuous flow reactor 4 with annular arrangement, and a reflector 6 is disposed at the lower part thereof.
The capillary continuous flow reactor is made of PFA, the inner diameter is 1mm, and the length is 16 m.
The capillary continuous flow reactor channels are arranged in a ring shape and are arranged in a lamination mode, and the number of lamination layers is 2.
The high-power panel type UV-LED lamp emits ultraviolet light with characteristic wavelength of 365nm, and the radiation window is 1200cm2The input power is 500W, and the optical power is 165mW/cm2。
In this embodiment, the above system is adopted to perform norbornadiene photosensitization cycloaddition reaction, the photosensitizing agent used is tetraethyl mikrone, the mass fraction of the photosensitizer is 0.55%, the system is solvent-free, the flow rate of the liquid phase in the capillary is 0.5ml/min, the reaction residence time is 25min, and the yield of the collected product, namely tetracycloheptane, is 99%.
Example 2
As shown in fig. 1, the present embodiment includes a high-power panel UV-LED lamp 1 and a capillary continuous flow reactor 2 arranged in a serpentine shape.
The capillary continuous flow reactor is made of quartz glass, and has the inner diameter of 2mm, the wall thickness of 1mm and the length of 2.26 m.
The capillary continuous flow reactor channels are arranged in a serpentine shape and are arranged in a single layer.
The high-power panel type UV-LED lamp emits ultraviolet light with characteristic wavelength of 365nm, and the radiation window is 1200cm2The input power is 500W, and the optical power is 165mW/cm2。
In this embodiment, the above system is adopted to perform norbornadiene photosensitization cycloaddition reaction, the photosensitizing agent used is tetraethyl mikrone, the mass fraction of the photosensitizer is 0.55%, the system is solvent-free, the flow rate of the liquid phase in the capillary is 0.18ml/min, the reaction residence time is 40min, and the yield of the collected product, namely tetracycloheptane, is 99%.
Example 3
The embodiment comprises the following steps: the device comprises a high-power panel type UV-LED lamp 1, a snakelike arrangement capillary continuous flow reactor 2, a snakelike arrangement laminated capillary 3 and a reflector 6.
The capillary continuous flow reactor is made of quartz glass, the inner diameter is 2mm, the wall thickness is 1mm, and the length is 22.6 m.
The capillary continuous flow reactor channels are arranged in a snake shape and are arranged in a lamination mode, and the number of lamination layers is 2.
The high-power panel type UV-LED lamp emits ultraviolet light with characteristic wavelength of 365nm, and the radiation window is 1200cm2The input power is 500W, and the optical power is 165mW/cm2。
A full reflector is arranged below the high-power panel type UV-LED lamp, and the capillary continuous flow reactor is arranged between the high-power panel type UV-LED lamp and the reflector.
In the embodiment, the system is adopted to carry out norbornadiene photosensitization cycloaddition reaction, the used photosensitizing agent is tetraethyl mikrone, the mass fraction of the photosensitizer is 0.55%, the photosensitizer is free of solvent, the flow rate of a liquid phase in a capillary is 2.2ml/min, the reaction retention time is 30min, the yield of the collected product, namely tetracycloheptane, is 99%, and the yield reaches 3 kg/day.
The embodiments described above are intended to facilitate a person of ordinary skill in the art in understanding and using the invention. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.
Claims (10)
1. A high throughput, low energy consumption, tetracyclic heptane continuous flow synthesis apparatus, comprising:
the fluid conveying device is used for conveying reaction raw materials;
the capillary continuous flow reactor is used for reacting raw materials to generate tetracyclic heptane and is arranged between the high-power panel type UV-LED lamp and the reflector.
2. The high throughput low energy consumption tetracycloheptane continuous flow synthesis apparatus according to claim 1, characterized in that said capillary continuous flow reactor is composed of capillary channels arranged in serpentine and/or circular shape.
3. The high-throughput low-energy consumption tetracycloheptane continuous flow synthesis device according to claim 2, wherein the capillary channels are arranged in a lamination mode, and the number of lamination layers is 2-5.
4. The tetracycloheptane continuous flow synthesis device with high throughput and low energy consumption as claimed in claim 2, wherein the material of the capillary continuous flow reactor has a light transmittance in the ultraviolet region higher than 80%, and comprises quartz, glass, PFA, FEP, ETFE, the inner diameter of the capillary is 0.5-6 mm, and the wall thickness is 0.1-2 mm.
5. A high-throughput low-energy consumption tetracycloheptane continuous flow synthesis device according to claim 1, characterized in that the maximum emission wavelength range of the high-power panel type UV-LED lamp is 315-400 nm, the half-peak width of the emitted light is 5-20 nm, and the light power is 20-2000 mW/cm2Radiation window at 150cm2～3000cm2The input power is between 200W and 2000W.
6. A high throughput low energy consumption tetracycloheptane continuous flow synthesis apparatus according to claim 1, wherein said reflectors or other light-reflecting fittings are placed under and around said high power panel UV-LED lamp.
7. The high-throughput low-energy consumption tetracyclic heptane continuous flow synthesis device according to claim 1, characterized in that the high-power panel type UV-LED lamps and the capillary continuous flow reactor are connected in parallel, and the number of the parallel connection is between 2 and 10 sets.
8. The synthesis method of the tetracycloheptane continuous flow synthesis device with high throughput and low energy consumption according to claim 1, characterized in that a photosensitizer tetraethyl mikrone is dissolved in norbornadiene to form a homogeneous reaction liquid;
sending the reaction liquid to a capillary continuous flow reactor through a fluid conveying device;
irradiating the reaction product in a capillary continuous flow reactor by an ultraviolet light source, and separating the reaction product by rotary evaporation to obtain the tetracyclic heptane.
9. The synthesis method of the high-throughput low-energy-consumption tetracycloheptane continuous flow synthesis device according to claim 1, characterized in that the mass fraction of the tetraethyl michelson ketone is in the range of 0.01% -5%.
10. The synthesis method of the tetracycloheptane continuous flow synthesis device with high throughput and low energy consumption according to claim 1, wherein during the irradiation reaction, the reaction temperature is 0-50 ℃, and the reaction time is 5-60 min.
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| CN202210361399.0A CN114733460A (en) | 2022-04-07 | 2022-04-07 | High-flux low-energy-consumption tetracyclic heptane continuous flow synthesis device and method |
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