CN113461500A - Device for refining cyclohexanone by cyclohexanol dehydrogenation - Google Patents
Device for refining cyclohexanone by cyclohexanol dehydrogenation Download PDFInfo
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- CN113461500A CN113461500A CN202110955188.5A CN202110955188A CN113461500A CN 113461500 A CN113461500 A CN 113461500A CN 202110955188 A CN202110955188 A CN 202110955188A CN 113461500 A CN113461500 A CN 113461500A
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- 238000006356 dehydrogenation reaction Methods 0.000 title claims abstract description 106
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 70
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000007670 refining Methods 0.000 title claims abstract description 20
- 238000000926 separation method Methods 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 116
- 238000010992 reflux Methods 0.000 claims description 72
- 150000002576 ketones Chemical class 0.000 claims description 69
- 230000008878 coupling Effects 0.000 claims description 30
- 238000010168 coupling process Methods 0.000 claims description 30
- 238000005859 coupling reaction Methods 0.000 claims description 30
- 239000007789 gas Substances 0.000 claims description 29
- 239000007791 liquid phase Substances 0.000 claims description 27
- 239000012071 phase Substances 0.000 claims description 22
- 230000018044 dehydration Effects 0.000 claims description 21
- 238000006297 dehydration reaction Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000007792 gaseous phase Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 33
- 238000000034 method Methods 0.000 abstract description 14
- 230000008569 process Effects 0.000 abstract description 10
- 239000002699 waste material Substances 0.000 abstract description 5
- 238000007599 discharging Methods 0.000 description 18
- 208000005156 Dehydration Diseases 0.000 description 16
- -1 alcohol ketone Chemical class 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 239000002994 raw material Substances 0.000 description 14
- 238000005265 energy consumption Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000003012 network analysis Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000002351 wastewater 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F28—HEAT EXCHANGE IN GENERAL
- F28D—HEAT-EXCHANGE APPARATUS, NOT PROVIDED FOR IN ANOTHER SUBCLASS, IN WHICH THE HEAT-EXCHANGE MEDIA DO NOT COME INTO DIRECT CONTACT
- F28D21/00—Heat-exchange apparatus not covered by any of the groups F28D1/00 - F28D20/00
- F28D21/0001—Recuperative heat exchangers
-
- 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
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F28—HEAT EXCHANGE IN GENERAL
- F28D—HEAT-EXCHANGE APPARATUS, NOT PROVIDED FOR IN ANOTHER SUBCLASS, IN WHICH THE HEAT-EXCHANGE MEDIA DO NOT COME INTO DIRECT CONTACT
- F28D21/00—Heat-exchange apparatus not covered by any of the groups F28D1/00 - F28D20/00
- F28D2021/0019—Other heat exchangers for particular applications; Heat exchange systems not otherwise provided for
- F28D2021/0022—Other heat exchangers for particular applications; Heat exchange systems not otherwise provided for for chemical reactors
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a device for refining cyclohexanone by cyclohexanol dehydrogenation. The device redesigns the six-tower process, realizes the refining and separation of cyclohexanol dehydrogenation materials, couples and utilizes a heat source and a cold source which can be utilized, and can improve the product yield, save the steam consumption, reduce the operation cost of the device and reduce the discharge amount of three wastes when being used for refining the cyclohexanone.
Description
Technical Field
The invention belongs to the field of organic chemical synthesis, and particularly relates to a device for refining cyclohexanone by cyclohexanol dehydrogenation.
Background
Cyclohexanone is an important chemical raw material, is mainly used for preparing nylon intermediates such as caprolactam, adipic acid and the like, and is widely applied to synthetic rubber, organic solvents and industrial coatings.
The traditional cyclohexene method cyclohexanone process mainly comprises main processes of benzene hydrogenation, cyclohexene refining, cyclohexene hydration, cyclohexanol refining, cyclohexanol dehydrogenation, cyclohexanone refining and the like, and a refining unit is a main energy consumption process of the whole process.
The invention patent with publication number CN106083544B discloses a method and a system for refining cyclohexanone and recycling cyclohexanol, which mainly comprise the following steps: sending the alcohol-ketone mixture into a light component removal tower to remove light components, sending materials extracted from the bottom of the tower into a cyclohexanone product tower, extracting a high-purity cyclohexanone product from the top of the tower, extracting a crude product mainly containing cyclohexanol from the bottom of the tower, then sending the crude product into a cyclohexanol recovery tower, and extracting cyclohexanol from the top of the tower; the method comprises the following steps of mixing the extracted cyclohexanol with a proper amount of water, heating the mixture, sending the mixture into a cyclohexanol dehydrogenation reactor for dehydrogenation reaction to obtain a mixed product containing cyclohexanol, cyclohexanone and water, carrying out two-stage cooling on the dehydrogenation product, carrying out gas-liquid separation on the dehydrogenation product, sending a gas phase and a liquid phase into a dehydration tower for dehydration treatment, sending oily wastewater removed from the top of the tower into a cyclohexane extraction tower, sending the obtained upper oil phase into an alcohol ketone recovery tower, and sending the oil phase containing cyclohexanone and cyclohexanol obtained from the bottom of the alcohol ketone recovery tower back to the dehydration tower for recycling.
However, the technical scheme of the invention needs to condense and vaporize cyclohexanol, so that energy consumption is increased, liquid-phase feeding is adopted for feeding, more energy consumption is needed for vaporizing the feeding, reaction intermediate products are independent from each other, heat in the intermediate products cannot be fully utilized, energy waste is generated, and part of cyclohexanone in an alcohol-ketone mixture cannot be recycled after entering a cyclohexanol recovery tower, so that product waste is caused, and production cost is increased.
Disclosure of Invention
In view of this, the present invention aims to provide a device for refining cyclohexanone by cyclohexanol dehydrogenation, so as to achieve comprehensive utilization of heat, reduce energy consumption, fully utilize raw materials, avoid waste, reduce production cost, and improve economic benefits.
In order to achieve the purpose, the technical scheme of the invention is realized as follows:
a device for refining cyclohexanone by cyclohexanol dehydrogenation comprises an alcohol tower and a dehydrogenation reactor, wherein a raw material cyclohexanol is injected into the alcohol tower through a feed inlet at the upper end of the alcohol tower, the cyclohexanol is separated by refluxing in the alcohol tower, a discharge outlet at the top of the alcohol tower can discharge cyclohexanol steam, and the cyclohexanol steam as a dehydrogenation reaction raw material can directly enter the dehydrogenation reactor to perform dehydrogenation reaction without condensation and re-vaporization, so that the energy consumption is reduced;
the dehydrogenation heat exchanger is characterized in that a tube pass feeding hole of the dehydrogenation heat exchanger is communicated with a top discharging hole of the first alcohol tower, the tube pass discharging hole of the dehydrogenation heat exchanger is communicated with a feeding hole of the dehydrogenation reactor, a shell pass feeding hole of the dehydrogenation heat exchanger is communicated with a discharging hole of the dehydrogenation reactor, gas discharged from the top discharging hole of the first alcohol tower exchanges heat with dehydrogenation products discharged from the dehydrogenation reactor in the dehydrogenation heat exchanger, the gas is preheated, heat is fully utilized, cyclohexanol after heat exchange enters the dehydrogenation reactor, dehydrogenation reaction is carried out, and crude alcohol ketone containing cyclohexanone is generated;
the shell side feed port of the alcohol tower feed heat exchanger is communicated with the shell side discharge port of the dehydrogenation heat exchanger, the heat-exchanged crude alcohol ketone is subjected to secondary heat exchange at the alcohol tower feed heat exchanger to realize secondary utilization of heat, the tube side discharge port of the alcohol tower feed heat exchanger is communicated with the middle feed port of the alcohol tower, and separation is carried out in the alcohol tower to realize material circulation;
a feed inlet in the middle of the light first tower is communicated with a shell-side liquid-phase discharge outlet of the alcohol tower feeding heat exchanger, and light components in the crude alcohol ketone are evaporated from a discharge outlet at the top of the light first tower;
a shell pass feed inlet of the coupling reboiler is communicated with a discharge outlet at the top of the light tower, a shell pass discharge outlet of the coupling reboiler is communicated with a reflux outlet at the top of the light tower, and a part of light components discharged from the top of the light tower are conveyed to the coupling reboiler for heat exchange to be used as a heat source of the coupling reboiler and can provide tower kettle heat for a cyclohexanone refining process, and the light components after heat exchange can return to the light tower again for circulation;
the middle feeding hole of the light second tower is communicated with the top discharging hole of the light first tower, the bottom discharging hole of the light second tower is communicated with the middle feeding hole of the light first tower, the other part of the light components discharged from the top of the light first tower is conveyed to the light second tower, the materials entering the light second tower are uncondensed gas-phase materials discharged from the top of the light first tower, the light second tower is used for recovering cyclohexanone in the materials discharged from the top of the light first tower, and the gas-phase feeding mode further improves the heat utilization rate and reduces the energy consumption;
the middle feed inlet of the ketone tower is respectively communicated with a bottom discharge outlet of the light tower and a tube pass discharge outlet of the coupling reboiler, materials discharged from the bottom discharge outlet of the light tower enter the ketone tower as raw materials, cyclohexanone is discharged from the top discharge outlet of the ketone tower, the bottom discharge outlet of the ketone tower is respectively communicated with the tube pass feed inlet of the coupling reboiler and the tube pass feed inlet of the alcohol tower feed heat exchanger, the materials discharged from the bottom discharge outlet of the ketone tower mainly comprise cyclohexanol and heavy components, one part of the materials returns to the ketone tower for separation after heat exchange is carried out at the coupling reboiler, the other part of the materials enters the alcohol tower for separation as the raw materials after heat exchange is carried out at the alcohol tower feed heat exchanger, and material circulation is realized;
the top feed inlet of the alcohol-water separation tower is communicated with the bottom feed inlet of the alcohol-water separation tower, the top feed outlet of the alcohol-water separation tower is communicated with the bottom feed inlet of the ketone tower, the alcohol-water separation tower is used for separating cyclohexanol and heavy components, the heavy component X oil is discharged from the bottom feed outlet of the alcohol-water separation tower, and the separated cyclohexanol enters the ketone tower to be recycled as a raw material.
Furthermore, a dehydration tower is arranged between the light tower and the alcohol tower feeding heat exchanger, a feed inlet of the dehydration tower is communicated with a shell side liquid phase discharge port of the alcohol tower feeding heat exchanger, a bottom discharge port of the dehydration tower is communicated with a middle feed inlet of the light tower, and crude alcohol ketone after heat exchange at the alcohol tower feeding heat exchanger enters the light tower after being dehydrated in the dehydration tower.
And furthermore, a dehydrogenation pump tank is arranged between the dehydration tower and the alcohol tower feeding heat exchanger, a feed inlet of the dehydrogenation pump tank is communicated with a shell side liquid phase discharge port of the alcohol tower feeding heat exchanger, and a discharge port of the dehydrogenation pump tank is communicated with a feed inlet of the dehydration tower.
The device further comprises a dehydrogenation condenser, wherein a feed inlet of the dehydrogenation condenser is communicated with a shell-side gas-phase discharge outlet of the alcohol tower feeding heat exchanger, a liquid-phase discharge outlet of the dehydrogenation condenser is communicated with a feed inlet of a dehydrogenation pump tank, a gas mixture is sent out from the dehydrogenation reactor, after heat exchange is carried out on the gas mixture through the dehydrogenation heat exchanger, the formed liquid phase automatically flows into the dehydrogenation pump tank after heat exchange is carried out on the gas mixture through a ketone tower kettle material at the alcohol tower feeding heat exchanger, and the uncondensed gas phase enters the dehydrogenation condenser for further condensation and then the recovered alcohol ketone enters the dehydrogenation pump tank.
The device further comprises a light first condenser and a light reflux tank, wherein a feed inlet of the light first condenser is communicated with a discharge outlet at the top of the light first tower, a liquid phase discharge outlet of the light first condenser is communicated with a feed inlet of the light reflux tank, a feed inlet of the light reflux tank is also communicated with a shell pass discharge outlet of a coupling reboiler, a discharge outlet of the light reflux tank is communicated with a reflux outlet at the top of the light first tower, a part of light components discharged from the top of the light first tower are conveyed to the coupling reboiler for heat exchange and used as a heat source of the coupling reboiler, the other part of light components are conveyed to a light second tower, and the rest part of light components are condensed at the light first condenser and then flow into the light first reflux tank and finally flow back to the light first tower for circulation.
The light second reflux tower is characterized by further comprising a light second condenser and a light second reflux tank, wherein a feeding hole of the light second condenser is communicated with a discharging hole at the top of the light second tower, a liquid-phase discharging hole of the light second condenser is communicated with a feeding hole of the light second reflux tank, a discharging hole of the light second reflux tank is communicated with a reflux hole at the top of the light second tower, light components are evaporated from the top of the light second tower, condensed liquid condensed at the light second condenser enters the light second reflux tank and flows back to the light second tower again for circulation, non-condensed gas is pumped out by a vacuum system, and light oil in the light second reflux tank can be sent out of a boundary area through a reflux pump for recovery.
The device comprises a ketone tower, a feeding hole of the ketone condenser is communicated with a discharging hole at the top of the ketone tower, a liquid-phase discharging hole of the ketone condenser is communicated with a feeding hole of the ketone reflux tank, a discharging hole of the ketone reflux tank is communicated with a top reflux hole of the ketone tower, cyclohexanone is evaporated from the top of the ketone tower, condensate after condensation of the ketone condenser flows into the ketone reflux tank, and non-condensable gas is extracted by a vacuum system. The condensate is used as reflux to the top of the ketone tower by the reflux pump part of the ketone tower, and the rest is used as cyclohexanone product to be sent out of the device.
The device further comprises an alcohol-condenser, wherein a feeding hole of the alcohol-condenser is communicated with a discharging hole at the top of the alcohol-tower, a discharging hole of the alcohol-condenser is communicated with a reflux hole at the top of the alcohol-tower, cyclohexanol is extracted from the top of the alcohol-tower, part of cyclohexanol is used as a reaction raw material to enter a dehydrogenation reactor, the other part of cyclohexanol is condensed at the alcohol-condenser to form condensate, and the condensate flows back to the alcohol-tower for circulation.
The device further comprises an alcohol reboiler and an alcohol reboiler, wherein a feed inlet of the alcohol reboiler is communicated with a bottom circulation material port of the alcohol first tower, a discharge outlet of the alcohol reboiler is communicated with a bottom feed inlet of the alcohol first tower, a feed inlet of the alcohol reboiler is communicated with a bottom circulation material port of the alcohol second tower, a discharge outlet of the alcohol reboiler is communicated with a bottom feed inlet of the alcohol second tower, and the alcohol reboiler and the alcohol second reboiler respectively provide external heat source support for the alcohol first tower and the alcohol second tower.
Further, the first alcohol tower is operated under positive pressure, the operating pressure is 30-100kPa, the gas phase pressure at the top of the first alcohol tower is greater than the pressure of the dehydrogenation reactor, the gas phase discharged from the first alcohol tower can directly enter the dehydrogenation reactor without condensation and re-vaporization, and the second alcohol tower is a stripping tower operated under negative pressure.
Compared with the prior art, the device for refining cyclohexanone by cyclohexanol dehydrogenation has the following advantages:
(1) the cyclohexanol in the device directly enters the dehydrogenation reactor through the top of the alcohol-tower, and is not condensed and re-vaporized, so that the steam consumption is saved;
(2) the light tower and the ketone tower in the device are thermally coupled, so that the consumption of steam and circulating water can be saved;
(3) the second light tower in the device adopts gas phase feeding, so that the consumption of steam and circulating water is saved;
(4) the alcohol second tower in the device adopts a stripping tower, and the gas phase at the top of the tower enters a ketone tower, so that the loss of cyclohexanone products is reduced;
(5) the alcohol secondary tower and the ketone tower in the device can share one set of vacuum system, so that the project investment is saved;
(6) the device adopts cyclohexanol dehydrogenation material to heat the feed of the alcohol tower, recovers the heat in the material and reduces the steam consumption.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate an embodiment of the invention and, together with the description, serve to explain the invention and not to limit the invention. In the drawings:
fig. 1 is a schematic view of a connection structure of a device according to an embodiment of the present invention.
Description of reference numerals:
1. an alcohol-first column; 2. a dehydrogenation reactor; 3. a feeding heat exchanger of the alcohol tower; 4. a light tower; 5. a coupling reboiler; 6. a light second tower; 7. a ketone column; 8. an alcohol-second column; 9. a dehydration tower; 10. a dehydrogenation pump tank; 11. a dehydrogenation condenser; 12. a condenser; 13. a light reflux drum; 14. a light second condenser; 15. a light second reflux tank; 16. a ketone condenser; 17. a ketone reflux drum; 18. an alcohol-condenser; 19. an alcohol reboiler; 20. an alcohol di-reboiler; 21. a dehydrogenation heat exchanger.
Detailed Description
Unless defined otherwise, technical terms used in the following examples have the same meanings as commonly understood by one of ordinary skill in the art to which the present invention belongs. The test reagents used in the following examples, unless otherwise specified, are all conventional biochemical reagents; the experimental methods are conventional methods unless otherwise specified.
The present invention will be described in detail with reference to the following examples and accompanying drawings.
In order to reduce the energy consumption of the device and reduce the consumption of steam and circulating water, the invention provides a six-tower process for refining and separating cyclohexanol dehydrogenation materials through full-process simulation and heat exchange network analysis, and a heat source and a cold source which are possibly utilized are coupled and utilized, so that the new process can not only save the steam consumption, but also reduce the discharge amount of three wastes.
According to the device for refining cyclohexanone by cyclohexanol dehydrogenation, disclosed by the invention, the raw material cyclohexanol is injected into the first alcohol tower 1 through a feed inlet at the upper end of the first alcohol tower 1, reflux separation of cyclohexanol is carried out in the first alcohol tower 1, cyclohexanol steam can be discharged from a discharge outlet at the top of the first alcohol tower 1, and the cyclohexanol steam can directly enter the dehydrogenation reactor 2 to carry out dehydrogenation reaction without being condensed and vaporized as a dehydrogenation reaction raw material, so that the energy consumption is reduced;
the tube side feed inlet of the dehydrogenation heat exchanger 21 is communicated with the top discharge outlet of the alcohol-first tower 1, the tube side discharge outlet of the dehydrogenation heat exchanger 21 is communicated with the feed inlet of the dehydrogenation reactor 2, the shell side feed inlet of the dehydrogenation heat exchanger 21 is communicated with the discharge outlet of the dehydrogenation reactor 2, gas discharged from the top discharge outlet of the alcohol-first tower 1 exchanges heat with dehydrogenation products discharged from the dehydrogenation reactor 2 in the dehydrogenation heat exchanger 21, the gas is preheated, heat is fully utilized, cyclohexanol subjected to heat exchange enters the dehydrogenation reactor 2, and dehydrogenation reaction is carried out, so that crude alcohol ketone containing cyclohexanone is generated;
the shell side feed inlet of the alcohol tower feed heat exchanger 3 is communicated with the shell side discharge outlet of the dehydrogenation heat exchanger 21, the heat-exchanged crude alcohol ketone is subjected to secondary heat exchange at the alcohol tower feed heat exchanger 3 to realize secondary utilization of heat, the tube side discharge outlet of the alcohol tower feed heat exchanger 3 is communicated with the middle feed inlet of the alcohol tower 1, and the material on the tube side of the alcohol tower feed heat exchanger 3 enters the alcohol tower 1 after heat exchange to be used as a raw material to be separated again to realize material circulation;
a feed inlet in the middle of the light first tower 4 is communicated with a shell-side liquid phase discharge outlet of the alcohol tower feeding heat exchanger 3, crude alcohol ketone after secondary heat exchange enters the light first tower 4, and light components in the crude alcohol ketone are evaporated from a discharge outlet at the top of the light first tower 4;
a shell pass feeding port of the coupling reboiler 5 is communicated with a top discharging port of the light first tower 4, a shell pass discharging port of the coupling reboiler 5 is communicated with a top reflux port of the light first tower 4, a part of light components discharged from the top of the light first tower 4 are conveyed to the coupling reboiler 5 for heat exchange, the light components are used as a heat source of the coupling reboiler 5 and can provide tower kettle heat for a cyclohexanone refining process, and the light components after heat exchange can return to the light first tower 4 again for circulation;
the middle feeding hole of the light second tower 6 is communicated with the top discharging hole of the light first tower 4, the bottom discharging hole of the light second tower 6 is communicated with the middle feeding hole of the light first tower 4, the other part of the light components discharged from the top of the light first tower 4 is conveyed to the light second tower 6, the materials entering the light second tower 6 are uncondensed gas-phase materials discharged from the top of the light first tower 4, the light second tower 6 is used for recovering cyclohexanone in the materials discharged from the top of the light first tower 4, and the gas-phase feeding mode further improves the heat utilization rate and reduces the energy consumption;
a middle feed inlet of the ketone tower 7 is respectively communicated with a bottom discharge outlet of the light tower 4 and a tube pass discharge outlet of the coupling reboiler 5, materials discharged from the bottom discharge outlet of the light tower 4 enter the ketone tower 7 as raw materials, cyclohexanone in the materials separated by the ketone tower 7 is discharged from a top discharge outlet of the ketone tower 7, the bottom discharge outlet of the ketone tower 7 is respectively communicated with a tube pass feed inlet of the coupling reboiler 5 and a tube pass feed inlet of the alcohol tower feeding heat exchanger 3, the materials discharged from the bottom discharge outlet of the ketone tower 7 mainly comprise cyclohexanol and heavy components, one part of the materials returns to the ketone tower 7 for separation after heat exchange is carried out at the coupling reboiler 5, the other part of the materials enters the alcohol tower 1 after heat exchange is carried out at the alcohol tower feeding heat exchanger 3 and is separated again as raw materials, and material circulation is realized;
the top feed inlet of the alcohol-water column 8 is communicated with the bottom discharge outlet of the alcohol-water column 1, the top discharge outlet of the alcohol-water column 8 is communicated with the bottom feed inlet of the ketone column 7, the alcohol-water column 8 is used for separating cyclohexanol and heavy components, wherein the heavy component X oil is discharged from the bottom discharge outlet of the alcohol-water column 8, and the separated cyclohexanol enters the ketone column 7 to be recycled as a raw material.
Further, a dehydration tower 9 is arranged between the light tower 4 and the alcohol tower feeding heat exchanger 3, a feed inlet of the dehydration tower 9 is communicated with a shell side liquid phase discharge port of the alcohol tower feeding heat exchanger 3, a bottom discharge port of the dehydration tower 9 is communicated with a middle feed inlet of the light tower 4, and crude alcohol ketone after heat exchange at the alcohol tower feeding heat exchanger 3 enters the light tower 4 after being dehydrated in the dehydration tower 9.
Further, a dehydrogenation pump tank 10 is arranged between the dehydration tower 9 and the alcohol tower feeding heat exchanger 3, a feed inlet of the dehydrogenation pump tank 10 is communicated with a shell side liquid phase discharge port of the alcohol tower feeding heat exchanger 3, and a discharge port of the dehydrogenation pump tank 10 is communicated with a feed inlet of the dehydration tower 9.
Further, the device also comprises a dehydrogenation condenser 11, wherein a feed inlet of the dehydrogenation condenser 11 is communicated with a shell pass gas phase discharge outlet of the alcohol tower feed heat exchanger 3, a liquid phase discharge outlet of the dehydrogenation condenser 11 is communicated with a feed inlet of the dehydrogenation pump tank 10, a gas mixture is sent out from the dehydrogenation reactor 2, is subjected to heat exchange through a dehydrogenation heat exchanger 21, is subjected to heat exchange through a material at the bottom of the ketone tower 7 at the alcohol tower feed heat exchanger 3, a formed liquid phase automatically flows into the dehydrogenation pump tank 10, and a non-condensed gas phase enters the dehydrogenation condenser 11 for further condensation and recovery of alcohol ketone and enters the dehydrogenation pump tank 10.
Further, the device also comprises a light first condenser 12 and a light first reflux tank 13, wherein a feed inlet of the light first condenser 12 is communicated with a discharge outlet at the top of the light first tower 4, a liquid phase discharge outlet of the light first condenser 12 is communicated with a feed inlet of the light first reflux tank 13, a feed inlet of the light first reflux tank 13 is also communicated with a shell pass discharge outlet of the coupling reboiler 5, a discharge outlet of the light first reflux tank 13 is communicated with a reflux outlet at the top of the light first tower 4, a part of light components discharged from the top of the light first tower 4 are conveyed to the coupling reboiler 5 for heat exchange and used as a heat source of the coupling reboiler 5, the other part of light components are conveyed to the light second tower 6, and the rest part of light components are condensed at the light first condenser 12 and then flow into the light first reflux tank 13, and finally flow back to the light first tower 4 for circulation.
Further, the device also comprises a light secondary condenser 14 and a light secondary reflux tank 15, wherein a feed inlet of the light secondary condenser 14 is communicated with a discharge outlet at the top of the light secondary tower 6, a liquid-phase discharge outlet of the light secondary condenser 14 is communicated with a feed inlet of the light secondary reflux tank 15, a discharge outlet of the light secondary reflux tank 15 is communicated with a reflux outlet at the top of the light secondary tower 6, light components are evaporated from the top of the light secondary tower 6, condensed liquid condensed at the light secondary condenser 14 enters the light secondary reflux tank 15 and flows back to the light secondary tower 6 again for circulation, non-condensed gas is extracted by a vacuum system, and light oil in the light secondary reflux tank 15 can be sent out of a boundary area by a reflux pump for recovery.
Further, the device also comprises a ketone condenser 16 and a ketone reflux tank 17, wherein a feed inlet of the ketone condenser 16 is communicated with a discharge outlet at the top of the ketone tower 7, a liquid-phase discharge outlet of the ketone condenser 16 is communicated with a feed inlet of the ketone reflux tank 17, a discharge outlet of the ketone reflux tank 17 is communicated with a reflux outlet at the top of the ketone tower 7, cyclohexanone is evaporated from the top of the ketone tower 7, condensate after condensation by the ketone condenser 16 flows into the ketone reflux tank 17, and non-condensable gas is extracted by a vacuum system. The condensate is sent to the top of the ketone tower 7 as reflux through the reflux pump part of the ketone tower 7, and the rest is sent out of the device as cyclohexanone products.
Further, the device also comprises an alcohol-condenser 18, wherein a feed inlet of the alcohol-condenser 18 is communicated with a discharge outlet at the top of the alcohol-tower 1, a discharge outlet of the alcohol-condenser 18 is communicated with a reflux outlet at the top of the alcohol-tower 1, cyclohexanol is extracted from the top of the alcohol-tower 1, part of cyclohexanol is used as a reaction raw material and enters the dehydrogenation reactor 2, the other part of cyclohexanol is condensed at the alcohol-condenser 18 to form condensate, and the condensate flows back to the alcohol-tower 1 for circulation.
Further, the device comprises an alcohol reboiler 19 and an alcohol reboiler 20, wherein a feed inlet of the alcohol reboiler 19 is communicated with a bottom circulation material port of the alcohol first tower 1, a discharge outlet of the alcohol reboiler 19 is communicated with a bottom feed inlet of the alcohol first tower 1, a feed inlet of the alcohol reboiler 20 is communicated with a bottom circulation material port of the alcohol second tower 8, a discharge outlet of the alcohol reboiler 20 is communicated with a bottom feed inlet of the alcohol second tower 8, and the alcohol reboiler 19 and the alcohol second reboiler 20 respectively provide external heat source support for the alcohol first tower 1 and the alcohol second tower 8.
Further, the alcohol tower 1 is operated under positive pressure, the operating pressure is 30-100kPa, the gas phase pressure at the top of the alcohol tower 1 is greater than the pressure of the dehydrogenation reactor 2, the gas phase discharged from the alcohol tower 1 can directly enter the dehydrogenation reactor 2 without condensation and re-vaporization, and the alcohol tower 8 is a stripping tower operated under negative pressure.
The process flow for the device to carry out the cyclohexanone dehydrogenation refining is as follows:
feeding cyclohexanol as the top reflux of the first alcohol tower 1, and directly feeding gas-phase cyclohexanol at the top of the first alcohol tower 1 into a dehydrogenation reactor 2 after heat exchange with a dehydrogenation product;
the gas mixture sent from the dehydrogenation reactor 2 is subjected to heat exchange through a dehydrogenation heat exchanger 21, and then subjected to heat exchange through the materials at the bottom of the ketone tower 7, the gas phase is condensed and then enters the dehydrogenation pump tank 10, and the liquid phase automatically flows into the dehydrogenation pump tank 10. Hydrogen is compressed and purified and then is sent out of a battery compartment, and crude alcohol ketone is sent to a light tower 4 after being dehydrated;
light components in the crude alcohol ketone are evaporated from the top of the light first tower 4, one part of the light components is heated for thermal coupling in the coupling reboiler 5, one part of the light components is extracted from the uncondensed part in the coupling reboiler 5 and enters the light second tower 6, the uncondensed gas phase is condensed at the top of the light first tower, and the condensate flows into the reflux tank of the light first tower 4. The condensed material in the coupling reboiler 5 enters the light reflux drum 13 by flowing into it. A part of the liquid in the light reflux tank 13 is used as reflux, and the rest is pumped to the ketone tower 7 through a discharge pump;
the light components are evaporated from the top of the light second tower 6, condensed liquid enters a light second reflux tank 15, non-condensable gas is pumped out by a vacuum system, and light oil in the light second reflux tank 15 is sent out of a boundary region by a reflux pump;
the cyclohexanone is evaporated from the top of the ketone tower 7, condensed liquid flows into the ketone reflux tank 17, and non-condensable gas is extracted by a vacuum system. Part of the condensate is sent to the top of the ketone tower 7 as reflux, the rest is sent out of the device as a cyclohexanone product, and the cyclohexanol and heavy components are sent to the alcohol tower feeding heat exchanger 3 by a ketone tower 7 discharge pump and enter the alcohol tower 1 after being preheated;
cyclohexanol is extracted from the top of the alcohol tower 1, heated by a dehydrogenation heat exchanger 21 and then enters a dehydrogenation reactor 2. The cyclohexanol and the X oil are quantitatively extracted from the tower bottom of the alcohol tower 1 to the alcohol tower 8. The gas phase at the top of the alcohol-water column 8 enters the bottom of the ketone column 7, and the X oil extracted from the bottom of the column is sent out of the device.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. The device for refining cyclohexanone by cyclohexanol dehydrogenation is characterized in that: comprises an alcohol tower and a dehydrogenation reactor;
the tube pass feed inlet of the dehydrogenation heat exchanger is communicated with the top discharge outlet of the alcohol tower, the tube pass discharge outlet of the dehydrogenation heat exchanger is communicated with the feed inlet of the dehydrogenation reactor, and the shell pass feed inlet of the dehydrogenation heat exchanger is communicated with the discharge outlet of the dehydrogenation reactor;
the shell side feed port of the alcohol tower feed heat exchanger is communicated with the shell side discharge port of the dehydrogenation heat exchanger, and the tube side discharge port of the alcohol tower feed heat exchanger is communicated with the middle feed port of the alcohol tower I;
a feed inlet in the middle of the light tower is communicated with a shell-side liquid-phase discharge outlet of the alcohol tower feeding heat exchanger;
the shell pass feed inlet of the coupling reboiler is communicated with the discharge outlet at the top of the light first tower, and the shell pass discharge outlet of the coupling reboiler is communicated with the reflux outlet at the top of the light first tower;
the middle feed inlet of the light second tower is communicated with the top discharge outlet of the light first tower, and the bottom discharge outlet of the light second tower is communicated with the middle feed inlet of the light first tower;
the middle feed inlet of the ketone tower is respectively communicated with the bottom discharge outlet of the light tower and the tube pass discharge outlet of the coupling reboiler, and the bottom discharge outlet of the ketone tower is respectively communicated with the tube pass feed inlet of the coupling reboiler and the tube pass feed inlet of the alcohol tower feed heat exchanger;
and the top feed inlet of the alcohol-water separation tower is communicated with the bottom feed outlet of the alcohol-water separation tower, and the top feed outlet of the alcohol-water separation tower is communicated with the bottom feed inlet of the ketone separation tower.
2. The apparatus of claim 1, wherein: and a dehydration tower is arranged between the light tower and the alcohol tower feeding heat exchanger, a feed inlet of the dehydration tower is communicated with a shell side liquid phase discharge port of the alcohol tower feeding heat exchanger, and a bottom discharge port of the dehydration tower is communicated with a middle feed inlet of the light tower.
3. The apparatus of claim 2, wherein: and a dehydrogenation pump tank is arranged between the dehydration tower and the alcohol tower feeding heat exchanger, a feed inlet of the dehydrogenation pump tank is communicated with a shell pass liquid phase discharge port of the alcohol tower feeding heat exchanger, and a discharge port of the dehydrogenation pump tank is communicated with a feed inlet of the dehydration tower.
4. The apparatus of claim 3, wherein: still include the dehydrogenation condenser, the feed inlet of dehydrogenation condenser and the shell side gaseous phase discharge gate intercommunication of alcohol tower feeding heat exchanger, the liquid phase discharge gate of dehydrogenation condenser and the feed inlet intercommunication of dehydrogenation pump groove.
5. The apparatus of claim 1, wherein: the device is characterized by further comprising a light condenser and a light reflux tank, wherein a feed inlet of the light condenser is communicated with a discharge outlet at the top of the light tower, a liquid-phase discharge outlet of the light condenser is communicated with a feed inlet of the light reflux tank, a feed inlet of the light reflux tank is also communicated with a shell pass discharge outlet of the coupling reboiler, and a discharge outlet of the light reflux tank is communicated with a reflux outlet at the top of the light tower.
6. The apparatus of claim 1, wherein: the device is characterized by further comprising a light secondary condenser and a light secondary reflux tank, wherein a feed inlet of the light secondary condenser is communicated with a discharge outlet at the top of the light secondary tower, a liquid-phase discharge outlet of the light secondary condenser is communicated with a feed inlet of the light secondary reflux tank, and a discharge outlet of the light secondary reflux tank is communicated with a reflux outlet at the top of the light secondary tower.
7. The apparatus of claim 1, wherein: the device comprises a ketone tower, a ketone reflux tank, a feed inlet, a liquid phase discharge port, and a liquid phase discharge port, a ketone column discharge port, a ketone reflux port, a ketone column discharge port, and a ketone column discharge port, a ketone column discharge port, a ketone column discharge port, a ketone column.
8. The apparatus of claim 1, wherein: the device also comprises an alcohol-condenser, wherein a feed inlet of the alcohol-condenser is communicated with a discharge outlet at the top of the alcohol-tower, and a discharge outlet of the alcohol-condenser is communicated with a reflux opening at the top of the alcohol-tower.
9. The apparatus of claim 1, wherein: the device comprises a first alcohol reboiler, a second alcohol reboiler and a first recycle feed inlet, wherein the first alcohol reboiler is communicated with a first recycle feed inlet at the bottom of the first alcohol tower, the second alcohol reboiler is communicated with a second recycle feed inlet at the bottom of the first alcohol tower, and the second alcohol reboiler is communicated with a second recycle feed inlet at the bottom of the second alcohol tower.
10. The apparatus of claim 1, wherein: the first alcohol tower is operated under positive pressure, the operating pressure is 30-100kPa, the gas phase pressure at the top of the first alcohol tower is greater than the pressure of the dehydrogenation reactor, and the second alcohol tower is a stripping tower operated under negative pressure.
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| CN202110955188.5A CN113461500A (en) | 2021-08-19 | 2021-08-19 | Device for refining cyclohexanone by cyclohexanol dehydrogenation |
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| CN202110955188.5A CN113461500A (en) | 2021-08-19 | 2021-08-19 | Device for refining cyclohexanone by cyclohexanol dehydrogenation |
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