CN118056802A - Production method and production device of bridge-type tetrahydrodicyclopentadiene - Google Patents
Production method and production device of bridge-type tetrahydrodicyclopentadiene Download PDFInfo
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- CN118056802A CN118056802A CN202211455663.3A CN202211455663A CN118056802A CN 118056802 A CN118056802 A CN 118056802A CN 202211455663 A CN202211455663 A CN 202211455663A CN 118056802 A CN118056802 A CN 118056802A
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- LPSXSORODABQKT-UHFFFAOYSA-N tetrahydrodicyclopentadiene Chemical compound C1C2CCC1C1C2CCC1 LPSXSORODABQKT-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 65
- 239000002994 raw material Substances 0.000 claims abstract description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 57
- 238000000926 separation method Methods 0.000 claims abstract description 50
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims abstract description 27
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 26
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 24
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims description 31
- 238000011084 recovery Methods 0.000 claims description 31
- 238000010992 reflux Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 2
- 230000006835 compression Effects 0.000 abstract description 4
- 238000007906 compression Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000010924 continuous production Methods 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 description 3
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000004215 Carbon black (E152) Substances 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
- 239000013064 chemical raw material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The application discloses a production method and a production device of bridge-type tetrahydrodicyclopentadiene, wherein the production method comprises a reaction stage and a separation stage; the reaction stage comprises: introducing raw materials containing dicyclopentadiene I and hydrogen I into a reactor, contacting with a catalyst, and reacting to obtain a hydrogenation reaction product; the separation stage comprises: and sequentially carrying out gas-liquid separation, rectification separation I and rectification separation II on the hydrogenation reaction product to sequentially obtain hydrogen II, hydrogen III, dicyclopentadiene II and bridge-type tetrahydrodicyclopentadiene. The method can be used for the production of bridge-type tetrahydrodicyclopentadiene, has continuous process and simple flow, saves energy consumption through hydrogen multistage compression, and is suitable for industrialized large-scale continuous operation.
Description
Technical Field
The application relates to a production method and a production device of bridge-type tetrahydrodicyclopentadiene, and belongs to the technical field of chemical industry.
Background
Bridge tetrahydrodicyclopentadiene is an important chemical raw material for synthesizing adamantane and other high-energy fuels, and can also be used as a pharmaceutical chemical intermediate and a traditional Chinese medicine additive for fine chemicals such as lubricants, resins and the like.
Chinese patent CN109651045 discloses a method for separating bridge type tetrahydrodicyclopentadiene by low temperature crystallization in laboratory, chinese patent CN109651045 discloses a refining method for obtaining tetrahydrodicyclopentadiene by crystallization, washing and extraction. Chinese patent CN111217663 discloses a process for preparing tetrahydrodicyclopentadiene. Chinese patent CN111662148 discloses a process for preparing bridge tetrahydrodicyclopentadiene.
In the prior art, the research on the continuous synthesis method of bridge tetrahydrodicyclopentadiene is basically limited to a conceptual stage, and a detailed continuous full-flow design is not seen.
Disclosure of Invention
The application provides a production process of bridge-type tetrahydrodicyclopentadiene, which is characterized in that the bridge-type tetrahydrodicyclopentadiene is generated by hydrogenation of dicyclopentadiene, and qualified products are obtained by separation, the process is continuous, the flow is simple, the energy consumption is saved by multistage compression of hydrogen, and the method is suitable for industrial large-scale continuous operation.
In one aspect of the application, a method for producing bridge tetrahydrodicyclopentadiene is provided, which comprises a reaction stage and a separation stage;
the reaction stage comprises: introducing raw materials containing dicyclopentadiene I and hydrogen I into a reactor, contacting with a catalyst, and reacting to obtain a hydrogenation reaction product;
The separation stage comprises: and sequentially carrying out gas-liquid separation, rectification separation I and rectification separation II on the hydrogenation reaction product to sequentially obtain hydrogen II, hydrogen III, dicyclopentadiene II and bridge-type tetrahydrodicyclopentadiene.
Optionally, the raw materials also comprise recycled hydrogen II, hydrogen III and dicyclopentadiene II.
Optionally, the gas-liquid separation includes: cooling and flash evaporating the hydrogenation reaction product, and separating to obtain hydrogen II and condensate;
The cooling temperature is 0-100 ℃;
The pressure of the flash evaporation treatment is 0.1-15 MPa.
Alternatively, the temperature of the cooling is independently selected from any value or range of values between any two points of 0 ℃, 10 ℃,20 ℃, 42 ℃, 60 ℃, 80 ℃, 100 ℃.
Alternatively, the pressure of the flash treatment is independently selected from any of 0.1MPa, 1MPa, 2.2MPa, 5MPa, 7MPa, 9MPa, 10MPa, 12MPa, 15MPa or a range of values between any two of the foregoing.
Optionally, the rectifying separation I comprises:
Introducing the condensate into a raw material recovery tower for rectification separation I, obtaining hydrogen II at the tower top, obtaining dicyclopentadiene II at the tower side, and obtaining distillate at the tower bottom;
The temperature of the top of the raw material recovery tower is 0-60 ℃;
the tower top pressure of the raw material recovery tower is 1-400 kPaA.
Optionally, the top temperature of the raw material recovery tower is selected from any value of 0 ℃, 20 ℃, 42 ℃ and 60 ℃ or a range value between any two points.
Alternatively, the overhead pressure of the feed recovery column is independently selected from any of 1kPaA, 50kPaA, 105kPaA, 150kPaA, 200kPaA, 250kPaA, 300kPaA, 350kPaA, 400kPaA, or a range of values between any two of the foregoing.
Optionally, the rectifying separation II comprises:
Introducing the distillate into a product tower for rectification separation II, and obtaining the bridge-type tetrahydrodicyclopentadiene at the bottom of the tower;
the temperature of the top of the product tower is 100-200 ℃;
The tower top pressure of the product tower is 1-400 kPaA.
Alternatively, the product column top temperature is independently selected from any value or range of values between any two points of 100 ℃, 110 ℃, 127 ℃, 140 ℃, 160 ℃, 180 ℃, 200 ℃.
Alternatively, the overhead pressure of the product column is independently selected from any of 1kPaA, 20kPaA, 50kPaA, 80kPaA, 110kPaA, 150kPaA, 200kPaA, 300kPaA, 400kPaA, or a range of values between any two of the foregoing.
In another aspect of the application, a production device of bridge-type tetrahydrodicyclopentadiene is provided, and the production device comprises a reaction unit and a separation unit which are sequentially communicated through pipelines;
the reaction unit comprises a reactor, wherein the reactor is provided with a raw material inlet and a hydrogenation reaction product outlet;
The separation unit comprises a gas-liquid separation module, a raw material recovery tower and a product tower which are sequentially communicated;
The gas-liquid separation module is provided with a hydrogenation reaction product inlet and a hydrogen II outlet, and the hydrogenation reaction product outlet is communicated with the hydrogenation reaction product inlet pipeline;
The top of the raw material recovery tower is provided with a hydrogen III outlet, the side wall of the tower is provided with a dicyclopentadiene II outlet, and the bottom of the tower is provided with a distillate outlet;
the bottom of the product tower is provided with a bridge type tetrahydrodicyclopentadiene outlet;
wherein, the raw material recovery tower and the product tower are both rectifying towers.
Optionally, the reaction unit further comprises a raw material preheater;
the raw material preheater is communicated with the raw material inlet through a pipeline;
The hydrogen II outlet and the hydrogen III outlet are respectively communicated with the raw material preheater pipeline;
the dicyclopentadiene II outlet is communicated with the raw material preheater pipeline.
Optionally, the gas-liquid separation module comprises a condenser and a flash tank which are connected in sequence; the flash tank is provided with a hydrogen II outlet and a condensate outlet, and the condenser is provided with a hydrogenation reaction product inlet.
Optionally, the separation unit further comprises a supercharging device I, a supercharging device II and a supercharging device III;
the supercharging device I is arranged on a pipeline connected with the raw material preheater at the outlet of the hydrogen II;
the supercharging device II is arranged on a pipeline connected with the raw material preheater at the outlet of the hydrogen III;
The pressurizing device III is arranged on a pipeline connected with the raw material preheater through the dicyclopentadiene II outlet.
Optionally, the reflux ratio of the raw material recovery tower is 0.1-50, and the theoretical plate number is 10-80;
the reflux ratio of the product tower is 30-180, and the theoretical plate number is 10-100.
Optionally, the reflux ratio of the raw material recovery tower is independently selected from any value of 0.1, 1, 10, 20, 30, 40 and 50 or a range value between any two points; the theoretical plate number of the raw material recovery tower is independently selected from any value of 10, 15, 30, 45, 50, 60, 70 and 80 or a range value between any two points.
Optionally, the reflux ratio of the product column is independently selected from any of 30, 40, 80, 100, 120, 150, 180 or a range between any two points; the theoretical plate number of the light component removal tower I is independently selected from any value of 10, 20, 30, 40, 50, 60, 70, 80, 90 and 100 or a range value between any two points.
As a specific embodiment, the apparatus includes:
The device comprises a raw material preheater, a reactor, a condenser, a gas-liquid separation tank, a No. 1 hydrogen compressor, a raw material recovery tower, a No. 2 hydrogen compressor, a product tower and a circulating pump. The method for using the device comprises the following steps:
(1) Mixing fresh dicyclopentadiene and hydrogen with circulating dicyclopentadiene and circulating hydrogen, heating to a reaction temperature in a raw material preheater 1, and feeding the mixture into a reactor 2;
(2) The reaction raw materials are subjected to catalytic reaction in a reactor 2 to obtain a hydrogenation reaction product;
(3) Condensing the hydrogenation reaction product in a condenser 3, changing the hydrogenation reaction product into gas-liquid two phases at low temperature, and realizing gas-liquid separation in a gas-liquid separation tank 4;
(4) Unreacted hydrogen separated in the separation tank 4 is pressurized by a No. 1 hydrogen compressor 5 and then mixed with fresh hydrogen;
(5) The liquid phase separated by the separating tank 4 is sent to a raw material recovery tower 6, unreacted dicyclopentadiene and hydrogen are separated from the top of the tower through rectification, the dicyclopentadiene is pressurized by a circulating pump 9 and recycled, and the hydrogen is pressurized by a No. 2 hydrogen compressor 7 and then mixed with fresh hydrogen;
(6) The distillate at the bottom of the raw material recovery tower 6 is crude bridge-type tetrahydrodicyclopentadiene, which is sent to a product tower 8, light impurities are separated from the top of the tower through rectification, and the bridge-type tetrahydrodicyclopentadiene product is obtained from the bottom of the tower.
The application has the beneficial effects that:
The application discloses a method for synthesizing C5-based hydrocarbon, which takes dicyclopentadiene as a raw material to generate bridge-type tetrahydrodicyclopentadiene through hydrogenation. The process flow adopts the cyclic operation of raw material preheating, reaction, gas phase separation, sequential rectification and multistage compression recovery, can be used for the production of bridge-type tetrahydrodicyclopentadiene, has continuous process and simple flow, saves energy consumption through hydrogen multistage compression, and is suitable for industrialized large-scale continuous operation.
Drawings
FIG. 1 is a schematic diagram of a production apparatus of bridged tetrahydrodicyclopentadiene in an embodiment of the present application.
Wherein:
1. a raw material preheater; 2. a reactor; 3. a condenser; 4. a gas-liquid separation tank; 5. a 1# hydrogen compressor; 6. a raw material recovery tower; 7. a 2# hydrogen compressor; 8. a product tower; 9. and a circulation pump.
Detailed Description
The present application is described in detail below with reference to examples, but the present application is not limited to these examples.
The starting materials and catalysts in the examples of the present application were purchased commercially, unless otherwise specified.
Example 1
As shown in FIG. 1, a bridge type tetrahydrodicyclopentadiene production device comprises the following components:
A raw material preheater 1, a reactor 2, a condenser 3, a gas-liquid separation tank 4, a No. 1 hydrogen compressor 5, a raw material recovery tower 6, a No. 2 hydrogen compressor 7, a product tower 8 and a circulating pump 9.
The raw material preheater 1, the reactor 2, the condenser 3, the gas-liquid separation tank 4, the raw material recovery tower 6 and the product tower 8 are sequentially communicated.
The top of the gas-liquid separation tank 4 is provided with a hydrogen II outlet which is communicated with the raw material preheater 1 through a No. 1 hydrogen compressor 5.
The top of the raw material recovery tower 6 is provided with a hydrogen III outlet which is communicated with the raw material preheater 1 through a No. 2 hydrogen compressor 7.
The side wall of the raw material recovery tower 6 is provided with a dicyclopentadiene II outlet which is communicated with the raw material preheater 1 through a circulating pump 9.
The side wall of the product tower 8 is provided with a light impurity outlet, and the bottom of the product tower is provided with a bridge type tetrahydrodicyclopentadiene outlet.
Example 2
By adopting the production device obtained in the example 1, fresh dicyclopentadiene and hydrogen are mixed with circulating dicyclopentadiene and circulating hydrogen, then are heated to 120 ℃ in a raw material preheater 1, are fed into a reactor 2 together, are contacted with a Ni-loaded molecular sieve catalyst, and are subjected to catalytic reaction to obtain hydrogenation reaction products. Condensing the hydrogenation reaction product to 42 ℃ in a condenser 3, changing the hydrogenation reaction product into gas-liquid two phases at low temperature, realizing gas-liquid separation in a gas-liquid separation tank 4 under the pressure of 2.2MPa, wherein the content of hydrogen in the separated unreacted hydrogen is 99.5% mol, and mixing the hydrogen with fresh hydrogen after being pressurized by a No. 1 hydrogen compressor 5. The liquid phase separated in the gas-liquid separation tank 4 was sent to the raw material recovery column 6, the temperature at the top of the recovery column 6 was 42 ℃, the pressure at the top of the column was 105kPaA, and 50 theoretical plates were provided, with a reflux ratio of 30. Unreacted dicyclopentadiene and hydrogen are separated from the top of the raw material recovery tower 6 through fractional condensation rectification, the dicyclopentadiene is pressurized by a circulating pump 9 and recycled, the purity of the separated hydrogen is 99.1 percent mol, the hydrogen is pressurized by a No. 2 hydrogen compressor 7 and then mixed with fresh hydrogen, the distillate at the bottom of the raw material recovery tower 6 is crude bridge type tetrahydrodicyclopentadiene, and the crude bridge type tetrahydrodicyclopentadiene is sent to a product tower 8 for separation. The temperature of the top of the product tower 8 is 127 ℃, the pressure of the top of the tower is 20kPa, 70 theoretical plates are arranged, the reflux ratio is 120, light impurities are separated from the top of the product tower 8 through total condensation and rectification, and the bridge type tetrahydrodicyclopentadiene product with the purity of 99.3 percent weight is obtained from the bottom of the product tower.
While the application has been described in terms of preferred embodiments, it will be understood by those skilled in the art that various changes and modifications can be made without departing from the scope of the application, and it is intended that the application is not limited to the specific embodiments disclosed.
Claims (10)
1. A method for producing bridge tetrahydrodicyclopentadiene is characterized in that,
The production method comprises a reaction stage and a separation stage;
the reaction stage comprises: introducing raw materials containing dicyclopentadiene I and hydrogen I into a reactor, contacting with a catalyst, and reacting to obtain a hydrogenation reaction product;
The separation stage comprises: and sequentially carrying out gas-liquid separation, rectification separation I and rectification separation II on the hydrogenation reaction product to sequentially obtain hydrogen II, hydrogen III, dicyclopentadiene II and bridge-type tetrahydrodicyclopentadiene.
2. The method according to claim 1, wherein,
The raw materials also comprise recycled hydrogen II, hydrogen III and dicyclopentadiene II.
3. The method according to claim 1, wherein,
The gas-liquid separation comprises: cooling and flash evaporating the hydrogenation reaction product, and separating to obtain hydrogen II and condensate;
The cooling temperature is 0-100 ℃;
The pressure of the flash evaporation treatment is 0.1-15 MPa.
4. The method according to claim 3, wherein,
The rectification separation I comprises the following steps:
Introducing the condensate into a raw material recovery tower for rectification separation I, obtaining hydrogen II at the tower top, obtaining dicyclopentadiene II at the tower side, and obtaining distillate at the tower bottom;
The temperature of the top of the raw material recovery tower is 0-60 ℃;
the tower top pressure of the raw material recovery tower is 1-400 kPaA.
5. The method according to claim 4, wherein,
The rectification separation II comprises:
Introducing the distillate into a product tower for rectification separation II, and obtaining the bridge-type tetrahydrodicyclopentadiene at the bottom of the tower;
DD220647I-DL
the temperature of the top of the product tower is 100-200 ℃;
The tower top pressure of the product tower is 1-400 kPaA.
6. A production device of bridge type tetrahydrodicyclopentadiene is characterized in that,
The production device comprises a reaction unit and a separation unit which are sequentially communicated through pipelines;
the reaction unit comprises a reactor, wherein the reactor is provided with a raw material inlet and a hydrogenation reaction product outlet;
The separation unit comprises a gas-liquid separation module, a raw material recovery tower and a product tower which are sequentially communicated;
The gas-liquid separation module is provided with a hydrogenation reaction product inlet and a hydrogen II outlet, and the hydrogenation reaction product outlet is communicated with the hydrogenation reaction product inlet pipeline;
The top of the raw material recovery tower is provided with a hydrogen III outlet, the side wall of the tower is provided with a dicyclopentadiene II outlet, and the bottom of the tower is provided with a distillate outlet;
the bottom of the product tower is provided with a bridge type tetrahydrodicyclopentadiene outlet;
wherein, the raw material recovery tower and the product tower are both rectifying towers.
7. The apparatus for producing of claim 6, wherein,
The reaction unit also comprises a raw material preheater;
the raw material preheater is communicated with the raw material inlet through a pipeline;
The hydrogen II outlet and the hydrogen III outlet are respectively communicated with the raw material preheater pipeline;
the dicyclopentadiene II outlet is communicated with the raw material preheater pipeline.
8. The apparatus for producing of claim 6, wherein,
The gas-liquid separation module comprises a condenser and a flash tank which are connected in sequence; the flash tank is provided with a hydrogen II outlet and a condensate outlet, and the condenser is provided with a hydrogenation reaction product inlet.
9. The apparatus for producing of claim 7, wherein,
The separation unit further comprises a supercharging device I, a supercharging device II and a supercharging device III;
the supercharging device I is arranged on a pipeline connected with the raw material preheater at the outlet of the hydrogen II;
The supercharging device II is arranged on a pipe DD220647I-DL connected with the outlet of the hydrogen III and the raw material preheater
A road;
The pressurizing device III is arranged on a pipeline connected with the raw material preheater through the dicyclopentadiene II outlet.
10. The apparatus for producing of claim 6, wherein,
The reflux ratio of the raw material recovery tower is 0.1-50, and the theoretical plate number is 10-80;
the reflux ratio of the product tower is 30-180, and the theoretical plate number is 10-100.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211455663.3A CN118056802A (en) | 2022-11-21 | 2022-11-21 | Production method and production device of bridge-type tetrahydrodicyclopentadiene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211455663.3A CN118056802A (en) | 2022-11-21 | 2022-11-21 | Production method and production device of bridge-type tetrahydrodicyclopentadiene |
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| Publication Number | Publication Date |
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| CN202211455663.3A Pending CN118056802A (en) | 2022-11-21 | 2022-11-21 | Production method and production device of bridge-type tetrahydrodicyclopentadiene |
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| Country | Link |
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| CN (1) | CN118056802A (en) |
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