CN111574341A - Intelligent reaction system and method for preparing cyclohexanone by selective hydrogenation of benzene - Google Patents
Intelligent reaction system and method for preparing cyclohexanone by selective hydrogenation of benzene Download PDFInfo
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 193
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 128
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 61
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 52
- 239000001257 hydrogen Substances 0.000 claims abstract description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 239000002994 raw material Substances 0.000 claims abstract description 31
- 239000007789 gas Substances 0.000 claims abstract description 16
- 239000007788 liquid Substances 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- 238000005886 esterification reaction Methods 0.000 claims description 27
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 22
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 22
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 19
- 230000032050 esterification Effects 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 230000033228 biological regulation Effects 0.000 claims description 15
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 claims description 14
- 238000005303 weighing Methods 0.000 claims description 14
- 230000006854 communication Effects 0.000 claims description 10
- 238000004891 communication Methods 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 238000007259 addition reaction Methods 0.000 claims description 8
- 238000001514 detection method Methods 0.000 claims description 4
- 230000007175 bidirectional communication Effects 0.000 claims description 3
- 238000012544 monitoring process Methods 0.000 claims description 3
- 238000007670 refining Methods 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 abstract description 15
- 238000012546 transfer Methods 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- 238000010992 reflux Methods 0.000 description 27
- 230000001105 regulatory effect Effects 0.000 description 19
- 239000000047 product Substances 0.000 description 10
- 238000004064 recycling Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 7
- 230000009471 action Effects 0.000 description 6
- 238000005265 energy consumption Methods 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 230000005501 phase interface Effects 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 2
- -1 alcohol ketone Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000013064 chemical raw material Substances 0.000 description 2
- 238000006477 desulfuration reaction Methods 0.000 description 2
- 230000023556 desulfurization Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- GHLZUHZBBNDWHW-UHFFFAOYSA-N nonanamide Chemical compound CCCCCCCCC(N)=O GHLZUHZBBNDWHW-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000026676 system process Effects 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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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
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- 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
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/10—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of aromatic six-membered rings
- C07C5/11—Partial hydrogenation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an intelligent reaction system and method for preparing cyclohexanone by selective hydrogenation of benzene, comprising a first raw material inlet arranged on the side wall of a hydrogenation reactor, wherein the first raw material inlet is provided with a first micro-interface generator for dispersing broken gas into bubbles; and a second raw material inlet is formed in the side wall of the addition reactor, and a second micro-interface generator is arranged at the second raw material inlet and used for dispersing the broken gas into bubbles. The intelligent control system comprises an intelligent control unit, an adjusting system and an automatic catalyst feeding system. On one hand, the intelligent reaction system increases the mass transfer area between the hydrogen and the liquid-phase material and improves the reaction efficiency after the micro-interface generator is arranged; the reaction temperature and pressure are reduced, and the safety and stability of the whole system are improved; on the other hand, full-automatic control is realized through an intelligent control system, so that the working efficiency is improved, the labor intensity of workers is reduced, and the automatic production and management level of enterprises is improved.
Description
Technical Field
The invention belongs to the technical field of micro-interface enhanced reaction, and particularly relates to an intelligent reaction system and method for preparing cyclohexanone by selective hydrogenation of benzene.
Background
The cyclohexanone is a chemical raw material which is widely applied and plays an important role in industrial production and daily life, the cyclohexanone is divided into two categories of amide and non-amide according to the usage of the cyclohexanone, wherein 70 percent of the amide cyclohexanone accounts for most of the usage of the cyclohexanone, and the fiber nylon 6 and the nylon 66 which are commonly used by people are prepared from the amide cyclohexanone; the cyclohexanone has the characteristics of high solubility, low volatility and the like, and can be used as an organic solvent, namely the non-amide cyclohexanone is used, and the cyclohexanone and other solvents are mixed for use, so that the evaporation speed of the system can be adjusted; in addition, cyclohexanone is widely used in the fields of medicines, anti-aging agents and the like, and is known to become a very important chemical raw material in industrial production, especially in the polyamide industry.
The selective hydrogenation of benzene to prepare cyclohexanone is the latest cyclohexanone production technology at present, and mainly comprises the benzene hydrogenation reaction to generate cyclohexene, the set of technology of the cyclohexene uses benzene as a raw material, the selective hydrogenation is carried out under the catalysis of a supported ruthenium catalyst to generate cyclohexene, the esterification reaction is carried out between the cyclohexene and acetic acid under the action of a solid acid catalyst, and the reaction is carried out to produce the cyclohexyl acetate. The produced cyclohexyl acetate and hydrogen are subjected to addition reaction in a ketone catalyst to generate acetic acid and cyclohexanol, and the cyclohexanol is dehydrogenated under the action of a dehydrogenation catalyst to prepare cyclohexanone. The process has high conversion rate and selectivity, almost no three wastes and high atom economy. Meanwhile, compared with a cyclohexene hydration method, the method omits a cyclohexane/cyclohexene separation process, and obviously reduces energy consumption. And the byproduct ethanol can be used for other chemical production, so that the added value of the product is increased, and the benefit is increased. However, although there are significant process advantages in the selective hydrogenation of benzene to cyclohexanone, there are some drawbacks: on one hand, the gas-liquid phase mass transfer areas of the existing hydrogenation reactor and the addition reactor are limited, hydrogen and liquid phase materials cannot be fully mixed in the reaction process, the mass transfer efficiency between the gas phase and the liquid phase is low, the reaction efficiency is low, and the energy consumption is high; meanwhile, the temperature and pressure inside the reactor are high, resulting in great reduction in the safety and stability of the whole system. On the other hand, the process has low automation degree and large supervision workload, a large amount of operators are required to perform field operation to complete the whole process in the treatment process, the operation is complex, the labor intensity of the operators is high, and meanwhile, the involved manual catalyst addition brings inconvenience to the operators and has extremely high danger.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
In view of the above, the first objective of the present invention is to provide an intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene, which, on one hand, can disperse and break hydrogen into microbubbles with micron-sized diameters by arranging micro interface generators at the raw material inlets of a hydrogenation reactor and an addition reactor, so as to increase the phase interface area between hydrogen and a liquid phase material, thereby fully satisfying the mass transfer space, increasing the retention time of hydrogen in the liquid phase, and reducing the consumption of hydrogen, thereby greatly improving the reaction efficiency and significantly reducing the energy consumption in the reaction process; meanwhile, the temperature and the pressure in the reactor are reduced, so that the safety and the stability of the whole system are improved; on the other hand, full-automatic control is realized through an intelligent control system, so that the working efficiency is improved, the labor intensity of workers is reduced, and the automatic production and management level of enterprises is improved.
The second purpose of the invention is to provide a method for preparing cyclohexanone by adopting the intelligent reaction system, the method has the advantages of milder operation condition, high automation degree, simple and convenient operation and better treatment effect than the prior art, and the reaction temperature and pressure are reduced while the reaction efficiency is ensured.
In order to achieve the above purpose of the present invention, the following technical solutions are adopted:
the invention provides an intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene, which comprises a hydrogenation reactor; the hydrogenation reactor is connected with a catalyst separator for separating the catalyst in the reaction product; the catalyst separator is connected with the esterification reactor and is used for carrying out esterification reaction on cyclohexene and acetic acid; the esterification reactor is connected with an addition reactor for addition reaction of cyclohexyl acetate and hydrogen; the addition reactor is connected with an ethanol rectifying tower and is used for separating ethanol; the ethanol rectifying tower is connected with the cyclohexanol rectifying tower and is used for separating gas-phase cyclohexanol; the cyclohexanol rectifying tower is connected with the dehydrogenation reactor and is used for performing cyclohexanol dehydrogenation reaction; the dehydrogenation reactor is connected with a gas-liquid separator for separating hydrogen; the gas-liquid separator is connected with the cyclohexanone rectifying tower and is used for separating the cyclohexanone;
the side wall of the hydrogenation reactor is provided with a first raw material inlet, and the first raw material inlet is provided with a first micro-interface generator for dispersing the crushed gas into bubbles; and a second raw material inlet is formed in the side wall of the addition reactor, and a second micro-interface generator is arranged at the second raw material inlet and used for dispersing the broken gas into bubbles.
The system also comprises an intelligent control system, wherein the intelligent control system comprises an intelligent control unit, an adjusting system and an automatic catalyst feeding system, and the adjusting system and the automatic catalyst feeding system are in two-way communication with the intelligent control unit; the adjusting system is connected with the hydrogenation reactor and the addition reactor for monitoring and adjusting the internal process parameters of the reactors in real time, and the automatic catalyst feeding system is connected with the hydrogenation reactor, the esterification reactor, the addition reactor and the dehydrogenation reactor for accurately feeding the catalyst.
In the prior art, the reaction for preparing cyclohexanone by selective hydrogenation of benzene has the following problems: on one hand, the gas-liquid phase mass transfer area of the existing reactor is limited, the reaction mixed raw material and hydrogen cannot be fully mixed in the reaction process, the energy consumption is high, and the reaction efficiency is low; meanwhile, the temperature and pressure are too high in the reaction process, so that the safety and stability of the whole system cannot be guaranteed. On the other hand, the process has low automation degree and large supervision workload, a large amount of operators are required to perform field operation to complete the whole process in the treatment process, the operation is complex, the labor intensity of the operators is high, and meanwhile, the involved manual catalyst addition brings inconvenience to the operators and has extremely high danger. According to the intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene, provided by the invention, on one hand, after micro-interface generators are arranged at the raw material inlets of a hydrogenation reactor and an addition reactor, hydrogen can be dispersed and crushed into micro-bubbles with micron-sized diameters, and the phase interface area between the hydrogen and a liquid phase material is increased, so that the mass transfer space is fully satisfied, the retention time of the hydrogen in a liquid phase is increased, the consumption of the hydrogen is reduced, the reaction efficiency is greatly improved, and the energy consumption in the reaction process is remarkably reduced; meanwhile, the temperature and the pressure in the reactor are reduced, so that the safety and the stability of the whole system are improved. On the other hand, full-automatic control is realized through an intelligent control system, so that the working efficiency is improved, the labor intensity of workers is reduced, and the automatic production and management level of enterprises is improved.
In the above-mentioned intelligent reaction system, the intelligent control unit gathers the signal from governing system and catalyst automatic feeding system, send corresponding command signal to governing system and catalyst automatic feeding system through data communication after analysis processes, catalyst automatic feeding system is automatic to begin to add the catalyst after receiving corresponding command signal, temperature control regulator, pressure regulation controller, liquid level regulation controller among the governing system receive corresponding command signal after to adjust temperature, pressure and liquid level.
Further, the regulation system comprises a temperature regulation controller, a pressure regulation controller and a liquid level regulation controller for controlling the temperature, pressure and liquid level inside the hydrogenation reactor and the addition reactor. It will be understood by those skilled in the art that the regulating system includes, but is not limited to, the above-mentioned ones, and various parameter-requiring control regulating controllers can be added according to the process requirements.
The device further comprises a feeding pipe, wherein an automatic regulating valve is arranged on the feeding pipe and used for automatically regulating the feeding amount of the catalyst according to an instruction.
Furthermore, the automatic catalyst feeding system is also provided with a weighing sensor for weighing before feeding the catalyst so as to facilitate accurate feeding; the weighing sensor is in communication connection with the automatic feeding system. And transmitting the weight signal to an automatic catalyst feeding system, and when the weight reaches a preset value, finishing feeding the catalyst, and closing the automatic regulating valve. The preferred high accuracy intelligence weighing sensor compares other weighing sensor, and transmission distance is far away, and the interference killing feature is strong.
Further, the intelligent control system further comprises a manual interface operating system, and the manual interface operating system is in two-way communication with the intelligent control unit. The system process parameters in the reaction process are transmitted to the human-computer interface, so that the running state of the system can be conveniently checked and controlled in real time, and the management and the use are safer and more efficient.
Further, the intelligent control system also comprises an alarm system which is connected with the intelligent control unit and is used for sending out a corresponding alarm when the related parameter exceeds a preset threshold value. Furthermore, a wireless communication module is arranged in the alarm system, and the alarm system is connected with the intelligent control unit through wireless communication.
Further, the first micro-interface generator and the second micro-interface generator are both pneumatic micro-interface generators; the number of the first micro-interface generator and the second micro-interface generator is at least more than one.
Furthermore, the first micro-interface generator and the second micro-interface generator are not limited in arrangement mode, arrangement position and number; more preferably, the number of the micro-interface generators is more than one, the micro-interface generators are arranged in parallel in front of the reactor from top to bottom, and the incoming hydrogen is dispersed and crushed simultaneously by the multi-row micro-interface generators arranged in parallel, so that the subsequent reaction efficiency can be effectively improved.
It will be appreciated by those skilled in the art that the micro-interface generator used in the present invention is described in the prior patents of the present inventor, such as the patents of application nos. CN201610641119.6, 201610641251.7, CN201710766435.0, CN106187660, CN105903425A, CN109437390A, CN205833127U and CN 207581700U. The detailed structure and operation principle of the micro bubble generator (i.e. micro interface generator) is described in detail in the prior patent CN201610641119.6, which describes that "the micro bubble generator comprises a body and a secondary crushing member, wherein the body is provided with a cavity, the body is provided with an inlet communicated with the cavity, the opposite first end and second end of the cavity are both open, and the cross-sectional area of the cavity decreases from the middle of the cavity to the first end and second end of the cavity; the secondary crushing member is disposed at least one of the first end and the second end of the cavity, a portion of the secondary crushing member is disposed within the cavity, and an annular passage is formed between the secondary crushing member and the through holes open at both ends of the cavity. The micron bubble generator also comprises an air inlet pipe and a liquid inlet pipe. "the specific working principle of the structure disclosed in the application document is as follows: liquid enters the micro-bubble generator tangentially through the liquid inlet pipe, and gas is rotated at a super high speed and cut to break gas bubbles into micro-bubbles at a micron level, so that the mass transfer area between a liquid phase and a gas phase is increased, and the micro-bubble generator in the patent belongs to a pneumatic micro-interface generator.
In addition, the first patent 201610641251.7 describes that the primary bubble breaker has a circulation liquid inlet, a circulation gas inlet and a gas-liquid mixture outlet, and the secondary bubble breaker communicates the feed inlet with the gas-liquid mixture outlet, which indicates that the bubble breakers all need to be mixed with gas and liquid, and in addition, as can be seen from the following drawings, the primary bubble breaker mainly uses the circulation liquid as power, so that the primary bubble breaker belongs to a hydraulic micro-interface generator, and the secondary bubble breaker simultaneously introduces the gas-liquid mixture into an elliptical rotating ball for rotation, thereby realizing bubble breaking in the rotating process, so that the secondary bubble breaker actually belongs to a gas-liquid linkage micro-interface generator. In fact, the micro-interface generator is a specific form of the micro-interface generator, whether it is a hydraulic micro-interface generator or a gas-liquid linkage micro-interface generator, however, the micro-interface generator adopted in the present invention is not limited to the above forms, and the specific structure of the bubble breaker described in the prior patent is only one of the forms that the micro-interface generator of the present invention can adopt.
Furthermore, the prior patent 201710766435.0 states that the principle of the bubble breaker is that high-speed jet flows are used to achieve mutual collision of gases, and also states that the bubble breaker can be used in a micro-interface strengthening reactor to verify the correlation between the bubble breaker and the micro-interface generator; moreover, in the prior patent CN106187660, there is a related description on the specific structure of the bubble breaker, see paragraphs [0031] to [0041] in the specification, and the accompanying drawings, which illustrate the specific working principle of the bubble breaker S-2 in detail, the top of the bubble breaker is a liquid phase inlet, and the side of the bubble breaker is a gas phase inlet, and the liquid phase coming from the top provides the entrainment power, so as to achieve the effect of breaking into ultra-fine bubbles, and in the accompanying drawings, the bubble breaker is also seen to be of a tapered structure, and the diameter of the upper part is larger than that of the lower part, and also for better providing the entrainment power for the liquid phase.
Since the micro-interface generator was just developed in the early stage of the prior patent application, the micro-interface generator was named as a micro-bubble generator (CN201610641119.6), a bubble breaker (201710766435.0) and the like in the early stage, and is named as a micro-interface generator in the later stage along with the continuous technical improvement, and the micro-interface generator in the present invention is equivalent to the micro-bubble generator, the bubble breaker and the like in the prior art, and has different names.
In summary, the micro-interface generator of the present invention belongs to the prior art, although some bubble breakers belong to the type of pneumatic bubble breakers, some bubble breakers belong to the type of hydraulic bubble breakers, and some bubble breakers belong to the type of gas-liquid linkage bubble breakers, the difference between the types is mainly selected according to the different specific working conditions, and in addition, the connection between the micro-interface generator and the reactor and other equipment, including the connection structure and the connection position, is determined according to the structure of the micro-interface generator, which is not limited.
Further, a catalyst outlet is formed in the bottom of the catalyst separator and used for recycling the catalyst into the hydrogenation reactor for recycling. The recovered catalyst is sent back to the interior of the hydrogenation reactor for recycling, so that the loss of the catalyst is reduced, the catalyst can be continuously taken out, regenerated and supplemented, and high activity and high selectivity are maintained, so that the catalyst can be continuously and stably produced for a long time.
Further, a kettle liquid outlet is formed in the bottom of the cyclohexanol rectifying tower, and the kettle liquid outlet is connected with the esterification reactor and used for recycling unreacted cyclohexyl acetate. The reactants after the esterification reaction contain a small amount of unreacted cyclohexyl acetate, flow out from a kettle liquid outlet after ethanol rectification and cyclohexanol rectification, return to the esterification reactor to participate in the esterification reaction again, and fully improve the utilization rate of raw materials.
Further, a hydrogen outlet is formed in the top of the gas-liquid separator, and the hydrogen outlet is connected with the second micro-interface generator and used for recycling the separated hydrogen. The product after cyclohexanol dehydrogenation contains a large amount of hydrogen, and the hydrogen can be recovered by a gas-liquid separator, so that the utilization rate of the hydrogen is fully improved.
Further, the system also comprises a benzene refiner for refining the raw material benzene, wherein a refined benzene outlet is arranged at the bottom of the benzene refiner and is connected with the first micro-interface generator. The benzene refiner is internally provided with a desulfurization adsorbent packing layer, the benzene refiner can refine the raw material benzene and is used for removing sulfur-containing impurities in the raw material benzene, and the sulfur content of the benzene coming out of the benzene refiner is less than or equal to 5PPb, so that the catalyst is prevented from being poisoned by the impurities in the raw material benzene.
And further, the device also comprises a cyclohexanone reflux tank, wherein a reflux pipeline for returning part of cyclohexanone to the cyclohexanone rectifying tower is arranged at the bottom of the cyclohexanone reflux tank. And a reflux pump is arranged on the reflux pipeline. And after being pressurized by a reflux pump, a part of condensate in the cyclohexanone reflux tank flows back to the cyclohexanone rectifying tower as a reflux pipeline so as to absorb the excess heat at the top of the cyclohexanone rectifying tower, maintain the heat balance of the whole tower, and improve the recovery purity of the cyclohexanone through multiple times of reflux. Compared with natural reflux, the reflux pump can adjust the reflux amount, so that the reflux amount is stable and the operability is good.
Further, the hydrogenation reactor and the addition reactor are both fixed bed catalytic reactors. Because the catalyst in the fixed bed catalytic reactor is directly filled on the fixed bed, the catalyst is not easy to wear in the bed layer, can be used for a long time, and has simple structure and convenient operation.
In addition, the invention also provides a method for preparing cyclohexanone by selective hydrogenation of benzene, which comprises the following steps:
after the hydrogen is dispersed and crushed into micro bubbles, the micro bubbles and benzene are subjected to catalytic hydrogenation reaction, and the micro bubbles and acetic acid are subjected to esterification reaction to obtain a reaction product;
and after the reaction product and the hydrogen which is dispersed and crushed continue to carry out addition reaction, dehydrogenating.
The intelligent control system in the steps realizes the automatic feeding of the catalyst and the full-automatic detection and control of the temperature, the pressure and the liquid level.
Further, refining crude benzene by a benzene refiner, introducing the refined crude benzene into the interior of a first micro-interface generator, introducing hydrogen into the interior of the first micro-interface generator, crushing the refined crude benzene into micro bubbles with the diameter of micron level, dispersing and crushing the hydrogen into the micro bubbles, fully emulsifying the micro bubbles with the benzene, introducing an emulsion into the interior of a hydrogenation reactor for hydrogenation reaction, introducing a reaction product into a catalyst separator for catalyst separation, returning the separated catalyst to the interior of the hydrogenation reactor for recycling, introducing cyclohexene with the catalyst removed into an esterification reactor for esterification reaction with acetic acid under the action of the catalyst, and introducing an esterification product, namely cyclohexyl acetate, into the interior of a second micro-interface generator; and simultaneously introducing hydrogen into the second micro-interface generator to break the hydrogen into micro-bubbles with the diameter of micron level, fully emulsifying the hydrogen and the cyclohexyl acetate, then introducing the emulsion into an addition reactor to perform addition reaction under the action of a catalyst, separating the product by ethanol, then introducing the product into a cyclohexanol rectifying tower, introducing gas-phase cyclohexanol into a dehydrogenation reactor to perform dehydrogenation reaction, simultaneously returning unreacted cyclohexyl acetate contained at the bottom of the cyclohexanol rectifying tower to the addition reactor for reuse, introducing the dehydrogenated product into a gas-liquid separator to separate the hydrogen, simultaneously returning the separated hydrogen to the second micro-interface generator for reuse, and finally introducing the alcohol ketone liquid after separating the hydrogen into the cyclohexanone rectifying tower to perform cyclohexanone separation and collection.
The intelligent control system in the steps realizes the automatic feeding of the catalyst and the full-automatic detection and control of the temperature, the pressure and the liquid level.
Further, the temperature of the hydrogenation reactor is 110-132 ℃; the pressure is 2.0-2.3 MPa; the temperature of the addition reactor is 178-205 ℃; the pressure is 2.1-3.0 MPa.
Compared with the prior art, the invention has the beneficial effects that:
according to the intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene, provided by the invention, on one hand, after micro-interface generators are arranged at the raw material inlets of a hydrogenation reactor and an addition reactor, hydrogen can be dispersed and crushed into micro-bubbles with micron-sized diameters, and the phase interface area between the hydrogen and a liquid phase material is increased, so that the mass transfer space is fully satisfied, the retention time of the hydrogen in a liquid phase is increased, the consumption of the hydrogen is reduced, the reaction efficiency is greatly improved, and the energy consumption in the reaction process is remarkably reduced; meanwhile, the temperature and the pressure in the reactor are reduced, so that the safety and the stability of the whole system are improved. On the other hand, full-automatic control is realized through an intelligent control system, so that the working efficiency is improved, the labor intensity of workers is reduced, and the automatic production and management level of enterprises is improved.
Drawings
Various other advantages and benefits will become apparent to those of ordinary skill in the art upon reading the following detailed description of the preferred embodiments. The drawings are only for purposes of illustrating the preferred embodiments and are not to be construed as limiting the invention. Also, like reference numerals are used to refer to like parts throughout the drawings. In the drawings:
FIG. 1 is a schematic structural diagram of an enhanced reaction system for preparing cyclohexanone by selective hydrogenation of benzene according to an embodiment of the present invention.
Description of the drawings:
10-a hydrogenation reactor; 11-a first feedstock inlet;
101-a first micro-interface generator; 20-a catalyst separator;
21-catalyst outlet; 30-an esterification reactor;
a 40-addition reactor; 41-a second feedstock inlet;
401-a second micro-interface generator; a 50-ethanol rectification column;
a 60-cyclohexanol distillation column; 61-a kettle liquid outlet;
70-a dehydrogenation reactor; 80-a gas-liquid separator;
81-hydrogen outlet; a 90-cyclohexanone rectifying tower;
100-an intelligent control unit; 110-a regulation system;
1101-a temperature regulation controller; 1102-a pressure regulating controller;
1103-level adjustment controller; 120-catalyst automatic feeding system;
1201-a weighing sensor; 1202-automatic regulating valve;
a 130-benzene refiner; 131-refined benzene outlet;
140-cyclohexanone reflux drum; 150-human interface operating system;
160-alarm system.
Detailed Description
The technical solutions of the present invention will be clearly and completely described below with reference to the accompanying drawings and the detailed description, but those skilled in the art will understand that the following described embodiments are some, not all, of the embodiments of the present invention, and are only used for illustrating the present invention, and should not be construed as limiting the scope of the present invention.
All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
In the description of the present invention, it should be noted that the terms "center", "upper", "lower", "left", "right", "vertical", "horizontal", "inner", "outer", etc., indicate orientations or positional relationships based on the orientations or positional relationships shown in the drawings, and are only for convenience of description and simplicity of description, but do not indicate or imply that the device or element being referred to must have a particular orientation, be constructed and operated in a particular orientation, and thus, should not be construed as limiting the present invention. Furthermore, the terms "first," "second," and "third" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance.
In the description of the present invention, it should be noted that, unless otherwise explicitly specified or limited, the terms "mounted," "connected," and "connected" are to be construed broadly, e.g., as meaning either a fixed connection, a removable connection, or an integral connection; can be mechanically or electrically connected; they may be connected directly or indirectly through intervening media, or they may be interconnected between two elements. The specific meanings of the above terms in the present invention can be understood in specific cases to those skilled in the art.
In order to more clearly illustrate the technical solution of the present invention, the following description is made in the form of specific embodiments.
Examples
Referring to fig. 1, the intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene according to the embodiment of the present invention includes a hydrogenation reactor 10; the hydrogenation reactor 10 is connected with a catalyst separator 20 for separating the catalyst in the reaction product; the catalyst separator 20 is connected with the esterification reactor 30 for esterification reaction of cyclohexene and acetic acid; the esterification reactor 30 is connected with an addition reactor 40 for addition reaction of cyclohexyl acetate and hydrogen; the addition reactor 40 is connected with an ethanol rectifying tower 50 for separating ethanol; the ethanol rectification column 50 is connected to a cyclohexanol rectification column 60 for separating gas-phase cyclohexanol; the cyclohexanol rectifying tower 60 is connected with a dehydrogenation reactor 70 for performing cyclohexanol dehydrogenation reaction; the dehydrogenation reactor 70 is connected with a gas-liquid separator 80 for separating hydrogen; the gas-liquid separator 80 connects a cyclohexanone rectification column 90 for separating cyclohexanone;
in this embodiment, the bottom of the catalyst separator 20 is provided with a catalyst outlet 21 for recycling the catalyst into the hydrogenation reactor 10, and the recycled catalyst is sent back to the hydrogenation reactor 10 for reuse, so that the loss of the catalyst is reduced, the catalyst can be continuously taken out, regenerated and supplemented, and high activity and high selectivity are maintained, thereby enabling long-term, continuous and stable production. A kettle liquid outlet 61 is formed in the bottom of the cyclohexanol rectifying tower 60, and the kettle liquid outlet 61 is connected with the esterification reactor 30 to be used for recycling unreacted cyclohexyl acetate; the top of the gas-liquid separator 80 is provided with a hydrogen outlet 81, and the hydrogen outlet 81 is connected with the second micro-interface generator 401 for reusing the separated hydrogen.
It is emphasized that the sidewall of the hydrogenation reactor 10 is provided with a first raw material inlet 11, and the first raw material inlet 11 is provided with a first micro-interface generator 101 for dispersing the crushing gas into bubbles; the side wall of the addition reactor 40 is provided with a second raw material inlet 41, and the second raw material inlet 41 is provided with a second micro-interface generator 401 for dispersing the fragmentation gas into bubbles. Preferably, the first micro-interface generator 101 and the second micro-interface generator 401 are both pneumatic micro-interface generators.
In this embodiment, a benzene refiner 130 is further included to refine the raw material benzene, a refined benzene outlet 131 is disposed at the bottom of the benzene refiner, and the refined benzene outlet 131 is connected to the first micro-interface generator 101. The benzene refiner 130 is internally provided with a desulfurization adsorbent packing layer, the benzene refiner can refine the raw material benzene and is used for removing sulfur-containing impurities in the raw material benzene, and the sulfur content of the benzene coming out of the benzene refiner is less than or equal to 5PPb, so that the catalyst is prevented from being poisoned by the impurities in the raw material benzene.
In this embodiment, the system further comprises a cyclohexanone reflux tank 140, and a reflux pipeline for returning part of cyclohexanone to the cyclohexanone rectification tower is arranged at the bottom of the cyclohexanone reflux tank 140. And a reflux pump is arranged on the reflux pipeline. A part of the condensate in the cyclohexanone reflux tank 140 is pressurized by the reflux pump and then flows back to the cyclohexanone rectifying tower 90 as a reflux pipeline so as to absorb the excess heat at the top of the cyclohexanone rectifying tower 90, maintain the heat balance of the whole tower, and improve the recovery purity of cyclohexanone through multiple reflux. Compared with natural reflux, the reflux pump can adjust the reflux amount, so that the reflux amount is stable and the operability is good.
In addition, the embodiment further comprises an intelligent control system, the intelligent control system comprises an intelligent control unit 100, a regulating system 110 and an automatic catalyst feeding system 120, and the regulating system 110 and the automatic catalyst feeding system 120 are in bidirectional communication with the intelligent control unit 100; the regulating system 110 comprises a temperature regulating controller 1101, a pressure regulating controller 1102 and a liquid level regulating controller 1103; it is understood that the regulating system includes, but is not limited to, the three types described above, and various parameter-requiring regulating controllers can be added according to the process requirements. The temperature regulation controller 1101, the pressure regulation controller 1102 and the liquid level regulation controller 1103 are connected with the hydrogenation reactor 10 and the addition reactor 40 for monitoring and regulating the internal process parameters of the reactors in real time, and the automatic catalyst feeding system 120 is connected with the hydrogenation reactor 10, the esterification reactor 30, the addition reactor 40 and the dehydrogenation reactor 70 for accurately feeding the catalyst. The catalyst automatic feeding system 120 is further provided with a weighing sensor 1201 for weighing before catalyst feeding so as to facilitate accurate feeding, and the weighing sensor 1201 is in communication connection with the catalyst automatic feeding system 120. Preferably, weighing sensor 1201 is intelligent weighing sensor, compares other weighing sensor, and transmission distance is far away, and the interference killing feature is strong. More preferably, the device also comprises a feeding pipe, and an automatic regulating valve 1202 is arranged on the feeding pipe and used for automatically regulating the feeding amount of the catalyst according to instructions. The weight signal is transmitted to the catalyst automatic feeding system 120, and when the weight reaches a preset value, the catalyst feeding is completed, and the automatic regulating valve 1202 is closed.
In the above embodiment, a human interface operating system 150 is further included, and the human interface operating system 150 is in bidirectional communication with the intelligent control unit 100. The system process parameters in the reaction process are transmitted to the human-computer interface, so that the running state of the system can be conveniently checked and controlled in real time, and the management and the use are safer and more efficient.
In the above embodiment, an alarm system 160 is further included, and the alarm system 160 is connected to the intelligent control unit 100 for issuing a corresponding alarm when the relevant parameter exceeds a predetermined threshold. Furthermore, a wireless communication module is arranged in the alarm system 160, and the alarm system 160 is connected with the intelligent control unit 100 through wireless communication.
The working process and principle of the intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene according to the invention are briefly described below.
Crude benzene enters the first micro-interface generator 101 after being refined by the benzene refiner 130, hydrogen is introduced into the first micro-interface generator 101 to be crushed into micro-bubbles with the diameter of micron level, the hydrogen is dispersed and crushed into the micro-bubbles and then fully emulsified with benzene, the emulsion enters the hydrogenation reactor 10 to carry out hydrogenation reaction, a reaction product enters the catalyst separator 20 to carry out catalyst separation, and the separated catalyst returns to the interior of the hydrogenation reactor 10 through the catalyst outlet 21 to be recycled. The cyclohexene with the catalyst removed enters an esterification reactor 30, is subjected to esterification reaction with acetic acid under the action of the catalyst, the esterification product, namely, the cyclohexyl acetate enters a second micro-interface generator 401, hydrogen is simultaneously introduced into the second micro-interface generator 401 to be crushed into micro-bubbles with the diameter of micron level, the hydrogen and the cyclohexyl acetate are fully emulsified, the emulsion then enters an addition reactor 40 to undergo addition reaction under the action of the catalyst, the product enters an ethanol rectifying tower 50 to separate ethanol, the mixture after ethanol separation enters a cyclohexanol rectifying tower 60, gas-phase cyclohexanone enters a dehydrogenation reactor 70 to undergo dehydrogenation reaction, meanwhile, unreacted cyclohexyl acetate returns to the addition reactor 40 through a still outlet 61 to be reused, the dehydrogenated product enters a gas-liquid separator 80 to separate the hydrogen, and simultaneously, the separated hydrogen returns to the second micro-interface generator 401 through a hydrogen outlet 81 to be reused, the separated alcohol ketone liquid enters a cyclohexanone rectifying tower 90 to separate and collect cyclohexanone.
The intelligent control system in the steps realizes the automatic feeding of the catalyst and the full-automatic detection and control of the temperature, the pressure and the liquid level.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. An intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene is characterized by comprising a hydrogenation reactor; the hydrogenation reactor is connected with a catalyst separator for separating the catalyst in the reaction product; the catalyst separator is connected with the esterification reactor and is used for carrying out esterification reaction on cyclohexene and acetic acid; the esterification reactor is connected with an addition reactor for addition reaction of cyclohexyl acetate and hydrogen; the addition reactor is connected with an ethanol rectifying tower and is used for separating ethanol; the ethanol rectifying tower is connected with the cyclohexanol rectifying tower and is used for separating gas-phase cyclohexanol; the cyclohexanol rectifying tower is connected with the dehydrogenation reactor and is used for performing cyclohexanol dehydrogenation reaction; the dehydrogenation reactor is connected with a gas-liquid separator for separating hydrogen; the gas-liquid separator is connected with the cyclohexanone rectifying tower and is used for separating the cyclohexanone;
the side wall of the hydrogenation reactor is provided with a first raw material inlet, and the first raw material inlet is provided with a first micro-interface generator for dispersing the crushed gas into bubbles; and a second raw material inlet is formed in the side wall of the addition reactor, and a second micro-interface generator is arranged at the second raw material inlet and used for dispersing the broken gas into bubbles.
The system also comprises an intelligent control system, wherein the intelligent control system comprises an intelligent control unit, an adjusting system and an automatic catalyst feeding system, and the adjusting system and the automatic catalyst feeding system are in two-way communication with the intelligent control unit; the adjusting system is connected with the hydrogenation reactor and the addition reactor for monitoring and adjusting the internal process parameters of the reactors in real time, and the automatic catalyst feeding system is connected with the hydrogenation reactor, the esterification reactor, the addition reactor and the dehydrogenation reactor for accurately feeding the catalyst.
2. The intelligent reaction system for the selective hydrogenation of benzene to cyclohexanone according to claim 1, wherein the regulation system comprises a temperature regulation controller, a pressure regulation controller and a liquid level regulation controller for controlling the temperature, pressure and liquid level inside the hydrogenation reactor and the addition reactor.
3. The intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene according to claim 1, further comprising a feeding pipe, wherein the feeding pipe is provided with an automatic adjusting valve for automatically adjusting the feeding amount of the catalyst according to an instruction.
4. The intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene according to claim 1, wherein the automatic catalyst feeding system is further provided with a weighing sensor for weighing before feeding the catalyst so as to accurately feed the catalyst.
5. The intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene according to claim 1, further comprising a manual interface operating system, wherein the manual interface operating system is in bidirectional communication with the intelligent control unit.
6. The intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene according to claim 1, further comprising an alarm system connected to the intelligent control unit for issuing a corresponding alarm when the relevant parameter exceeds a predetermined threshold.
7. The intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene according to claim 1, wherein the first micro-interface generator and the second micro-interface generator are pneumatic micro-interface generators; the number of the first micro-interface generator and the second micro-interface generator is at least more than one.
8. The intelligent reaction system for preparing cyclohexanone by selective hydrogenation of benzene according to claim 1, further comprising a benzene refiner for refining the raw material benzene, wherein a refined benzene outlet is arranged at the bottom of the benzene refiner, and the refined benzene outlet is connected to the first micro-interface generator.
9. The method for preparing cyclohexanone by using the intelligent reaction system as set forth in any one of claims 1 to 8, comprising the steps of:
after the hydrogen is dispersed and crushed into micro bubbles, the micro bubbles and benzene are subjected to catalytic hydrogenation reaction, and the micro bubbles and acetic acid are subjected to esterification reaction to obtain a reaction product;
and after the reaction product and the hydrogen which is dispersed and crushed continue to carry out addition reaction, dehydrogenating.
The intelligent control system in the steps realizes the automatic feeding of the catalyst and the full-automatic detection and control of the temperature, the pressure and the liquid level.
10. The process as claimed in claim 9, wherein the temperature of the hydrogenation reactor is 110-132 ℃; the pressure is 2.0-2.3 MPa; the temperature of the addition reactor is 178-205 ℃; the pressure is 2.1-3.0 MPa.
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| WO2021227136A1 (en) * | 2020-05-14 | 2021-11-18 | 南京延长反应技术研究院有限公司 | Enhanced reaction system and method for preparing cyclohexanone by selective hydrogenation of benzene |
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