CN112521256B - Method for efficiently separating cyclohexanone and removing impurities in cyclohexanol - Google Patents
Method for efficiently separating cyclohexanone and removing impurities in cyclohexanol Download PDFInfo
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- CN112521256B CN112521256B CN201910880368.4A CN201910880368A CN112521256B CN 112521256 B CN112521256 B CN 112521256B CN 201910880368 A CN201910880368 A CN 201910880368A CN 112521256 B CN112521256 B CN 112521256B
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 170
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims abstract description 141
- 239000012535 impurity Substances 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 58
- 238000005192 partition Methods 0.000 claims abstract description 69
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 48
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 30
- -1 alcohol ketone Chemical class 0.000 claims abstract description 21
- 238000010992 reflux Methods 0.000 claims description 26
- 238000007599 discharging Methods 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 16
- 238000000926 separation method Methods 0.000 abstract description 21
- 238000005265 energy consumption Methods 0.000 abstract description 13
- 150000002170 ethers Chemical class 0.000 abstract description 12
- 238000007670 refining Methods 0.000 abstract description 12
- 238000010276 construction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 18
- GKRALBJDXHXFNB-UHFFFAOYSA-N butoxycyclohexane Chemical compound CCCCOC1CCCCC1 GKRALBJDXHXFNB-UHFFFAOYSA-N 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- HLTMUYBTNSVOFY-UHFFFAOYSA-N pentylcyclohexane Chemical compound CCCCCC1CCCCC1 HLTMUYBTNSVOFY-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000004886 process control Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 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
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
-
- 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
-
- 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
Abstract
The invention discloses a method for efficiently separating cyclohexanone and removing impurities in cyclohexanol, which comprises the following process flows: the crude alcohol ketone at the bottom of the light component removal tower enters a partition tower, cyclohexanone product is extracted from the top of the partition tower, cyclohexanol is extracted from the side line, intermediate ether components and heavy matters containing cyclohexanol extracted from the tower bottom enter a impurity removal tower, the intermediate ether components and the heavy matters are continuously removed from the bottom of the impurity removal tower, and the cyclohexanol extracted from the top of the impurity removal tower and the cyclohexanol extracted from the side line of the partition tower are directly used as the feed of a dehydrogenation reactor after being combined. The invention not only achieves the refining purpose of cyclohexanone and cyclohexanol, but also can flexibly remove the intermediate components of ethers in cyclohexanol on line, and reduces the energy consumption, investment and construction occupation of the alcohol-ketone separation device.
Description
Technical Field
The invention belongs to the technical field of cyclohexanone preparation, and in particular relates to a method for efficiently separating cyclohexanone and removing impurities in cyclohexanol.
Background
Cyclohexanone is a major intermediate for the production of caprolactam and adipic acid and is also an important industrial solvent. At present, the production methods of cyclohexanone mainly comprise a cyclohexane oxidation method, a cyclohexene hydration method and a phenol hydrogenation method, and in the process of catalyzing and dehydrogenating cyclohexanol generated by the production methods at a certain temperature to generate cyclohexanone, light component and heavy component impurities which are inevitably generated are more generated in the cyclohexane oxidation process.
The separating and refining flow of the cyclohexanone product and cyclohexanol as a dehydrogenation reaction raw material is generally as follows: and (3) sequentially dehydrating crude alcohol ketone (the crude alcohol ketone generated by oxidation, cyclohexyl hydrogen peroxide decomposition and other reactions in the cyclohexane oxidation process) after the cyclohexanol dehydrogenation by a drying tower, removing light components by a light component removal tower, refining a cyclohexanone product by a cyclohexanone tower, separating heavy component impurities such as cyclohexanol and X oil by the cyclohexanol tower, and finally obtaining the cyclohexanol raw material of the cyclohexanone product and a dehydrogenation reactor. In the cyclohexanol separating tower, there is one small tower with 8 small tower plates and with reduced diameter, and the material in the bottom of the main tower overflows into the small tower to heat and distill, and the temperature of the small tower is controlled to control the outward throwing amount of heavy component and the purity of cyclohexanol in the tower top. In the flow, the operating pressure of the light component removal tower top is 20 KPaA-57 KPaA, the operating temperature of the corresponding tower top is 110 ℃ to 130 ℃, the operating pressure of the cyclohexanone refining tower top is about 5KPaA, the operating temperature of the tower bottom is about 100 ℃, the operating pressure of the cyclohexanol separation tower top is 5 KPaA-8 KPaA, the operating temperature of the corresponding main tower bottom is 116 ℃ to 130 ℃, and the operating temperature of the small tower bottom is 150 ℃ to 165 ℃.
The boiling points of cyclohexanone and cyclohexanol are 155 ℃ and 161 ℃ respectively, and the boiling points of the cyclohexanone and cyclohexanol are close to each other; the boiling point (140-150 ℃) of light impurities such as methyl cyclopentanone, methyl cyclopentanol and the like is very similar to that of cyclohexanone; while the boiling point of heavy impurities such as amyl cyclohexane and butyl cyclohexyl ether is higher than that of cyclohexanol, the heavy impurities are azeotroped with cyclohexanol under the condition of reduced pressure rectification of an alcohol tower, the heavy impurities are distilled off from the top of the tower along with the cyclohexanol, and the heavy impurities accumulate in a rectification system along with long-time operation of the device, so that the content of intermediate components between the cyclohexanol and heavy components in raw alcohol ketone is always 10%. The boiling points of the separated substances are similar, and a larger reflux ratio is needed during separation, so that the separation energy consumption of the device is very large, the separation capacity of equipment is occupied, and a small amount of impurities enter cyclohexanone products at the top of the ketone tower, so that the quality of the cyclohexanone is reduced; in order to ensure the quality of cyclohexanone, the content of cyclohexanone in the ketone tower kettle has to be improved, so that the content of cyclohexanone in cyclohexanol of a dehydrogenation raw material is high, the conversion rate of cyclohexanol is reduced, the condensation side reaction of cyclohexanone is increased, and the selectivity of cyclohexanol dehydrogenation is reduced.
In the existing cyclohexanone dehydrogenation process:
patent 201610919752.7 discloses a method for efficiently separating and refining cyclohexanone products, which utilizes a single cyclohexanone tower to remove light components and simultaneously refine cyclohexanone, namely crude alcohol ketone generated by cyclohexanol dehydrogenation is dehydrated and then sent to the cyclohexanone tower, the light components are extracted from the top of the cyclohexanone tower, the cyclohexanone is extracted from the side line, and the heavy components of cyclohexanol and X oil are extracted from the bottom of the cyclohexanone tower. Patent 201610389965.3 discloses a method and a system for refining cyclohexanone and recycling cyclohexanol, wherein after alcohol-ketone mixture is sent to a light component removal tower to remove light components, a tower bottom material is sent to a cyclohexanone product tower, cyclohexanone is produced at the tower top of the ketone, a tower bottom produced material is sent to an alcohol refining tower, cyclohexanol is produced at the tower top of the alcohol, the alcohol is mixed with a proper amount of water and sent to a dehydrogenation reactor, after the dehydrogenation product is cooled and separated in gas-liquid mode, a gas phase and a liquid phase are sent to a dehydration tower, waste water containing trace oil at the tower top is sent to a cyclohexane extraction tower, and an extract is sent to an alcohol-ketone recovery tower to recover alcohol ketone. Patent 201510660301.1 discloses a process for producing cyclohexanone by dehydrogenation of cyclohexanol, wherein vaporized cyclic alcohol is fed into a dehydrogenation reactor, heavy substances in the product are separated out from the dehydrogenation product before hydrogen is separated out, heat contained in the reaction product is fully utilized, the production energy consumption of cyclohexanone is reduced, and side reactions caused by repeated distillation of cyclohexanol are reduced.
Wu Shouhui in petrochemical 1983,12 (10): 642-649 it is pointed out that impurities contained in cyclohexanol can increase the thermal instability of cyclohexanol itself, with an increase of 3-4% in high boiling substances when 90-91% of cyclohexanol by industrial rectification is passed through a superheater, and with 98-98.8% of cyclohexanol, almost unchanged. The dehydrogenation selectivity is reduced by about 4% when using industrially distilled cyclohexanol compared to pure cyclohexanol, so that the cyclohexanol dehydrogenation feed should be refined to reduce the impurity content in cyclohexanol as much as possible, for example by adding a cutting tower in the alcohol ketone rectification system. However, no specific method is given. Patent 200410097596.8 proposes a method for obtaining high-purity cyclohexanol from cyclohexane oxidation products, wherein a raw material is an alcohol tower distillate containing 80% -95% of cyclohexanol, residual low-boiling components and cyclohexanone are removed by vacuum distillation, and then the residue is subjected to normal pressure or pressure distillation to remove substances such as amyl cyclohexane and butyl cyclohexyl ether which are difficult to separate from cyclohexanol in vacuum distillation, thereby obtaining cyclohexanol with purity of more than 99%. However, the "residual low boiling point component and cyclohexanone removed by vacuum distillation" of the method contains not only about 43% of cyclohexanone but also about 45% of cyclohexanol, and more than 10% of intermediate components such as butylcyclohexyl ether and pentylcyclohexane which are azeotroped together with cyclohexanol, and if this material is returned to the system, the intermediate components are still accumulated in the system, and if this material is discharged from the system, the material consumption is increased. The patent 201620707871.1 discloses a device for removing impurities of butyl cyclohexyl ether in the production process of cyclohexanone, which is characterized in that a rectifying tower is added behind a cyclohexanol evaporator to carry out normal pressure or pressurized rectification on crude cyclohexanol, and part of butyl cyclohexyl ether is discharged from a tower kettle to a heavy component tank, so that the aim of reducing the content of intermediate components in the crude cyclohexanol is fulfilled. But the content of butyl cyclohexyl ether in the discharged tower kettle liquid is only 25-35%, and the rest components are cyclohexanol, which means that 2-3 times of cyclohexanol with butyl cyclohexyl ether is treated as a byproduct, thereby increasing material consumption. Patent 201610837394.5 discloses a process for preparing cyclohexanone by dehydrogenating cyclohexanol, wherein the equipment of the cyclohexanol dehydrogenation procedure consists of a cyclohexanol evaporator, a vapor-liquid separator, a normal pressure or pressurized rectifying tower and a cyclohexanol dehydrogenation reactor; the rectifying tower is only provided with a stripping section, and the tower kettle is provided with a reboiler. The technology can greatly reduce the concentration of the methylcyclohexanone, the heptanone and the analogues thereof contained in the materials of the cyclohexanone rectification process and the cyclohexanol dehydrogenation process, and reduce the circulation and accumulation of the methylcyclohexanone, the heptanone and the analogues thereof in the cyclohexanone rectification process and the cyclohexanol dehydrogenation process. However, the materials discharged from the tower kettle of the process still contain about 30 percent of cyclohexanol, thereby increasing material consumption. In addition, these impurities, which are very low in content, are removed from the column bottom under normal pressure or pressurized conditions, requiring high energy consumption.
One common point of these patent technologies is that no new energy saving technology is introduced, but some combinations and improvements are made on the separation flow, and the energy consumption of the device is still large. When refining the intermediate components in the cyclohexanol fed to the dehydrogenation reactor, the engineering design and operating conditions of the cyclohexanol tower are not optimized to remove impurities in the cyclohexanol, but only after the dehydrogenation reactor is fed to the dehydrogenation reactor and heated by cooling, the impurities are separated and partially removed by means of tank flash evaporation or tower rectification, which requires additional energy consumption, and the amount of treated material cannot be too large, otherwise the energy consumption will be higher.
Disclosure of Invention
The invention aims to develop a method for efficiently separating cyclohexanone and removing impurities in cyclohexanol on line, so as to overcome the defects of the prior art, achieve the purposes of refining cyclohexanone and removing impurities in cyclohexanol, reduce energy consumption, reduce loss of cyclohexanone and device investment and operation cost.
In order to achieve the technical aim, the invention provides a method for efficiently separating cyclohexanone and removing impurities in cyclohexanol, which comprises the following process flows: the crude alcohol ketone at the bottom of the light component removal tower enters a partition tower, cyclohexanone product is extracted from the top of the partition tower, cyclohexanol is extracted from the side line, intermediate ether components and heavy matters containing cyclohexanol extracted from the tower bottom enter a impurity removal tower, the intermediate ether components and the heavy matters are continuously removed from the bottom of the impurity removal tower, and the cyclohexanol extracted from the top of the impurity removal tower and the cyclohexanol extracted from the side line of the partition tower are directly used as the feed of a dehydrogenation reactor after being combined.
The vertical partition board is arranged in the axial middle position in the partition wall tower, the partition wall tower is divided into a feeding side and a discharging side, crude alcohol ketone from the light component removing tower bottom enters the feeding side of the partition wall tower, part of the condensed gas phase at the top of the partition wall tower flows back to the top of the partition wall tower, and the rest part of the condensed gas phase is taken as cyclohexanone product to be extracted.
The liquid collecting tank is arranged between the inner member at the top of the partition wall tower and the vertical partition plate, liquid in the liquid collecting tank is respectively and internally refluxed to the inner members at the tops of the feeding side and the discharging side through the distributor, and the equipment investment can be saved by adopting an internal reflux mode, the operation process control is convenient, and a reflux pump is not needed to be externally arranged.
The impurity removing tower is operated under normal pressure or under pressure.
The tower top operation temperature of the partition wall tower is 45-65 ℃, the operation pressure is 2 KPaA-8 KPaA, the reflux ratio is 2-5, the internal reflux from the liquid collecting box to the feeding side and the discharging side is 1/3-1/2, 1/2-2/3 respectively, the tower bottom operation temperature is 100-120 ℃, and the operation pressure is 8 KPaA-15 KPaA.
The operating temperature of the tower top of the impurity removal tower is 150-185 ℃, the operating pressure is normal pressure-100 KPaG, the reflux ratio is 0-2, the operating temperature of the tower kettle is 170-220 ℃, and the operating pressure is 100 KPaG-200 KPaG.
The partition tower adopts a plate tower or a packed tower, and the theoretical plate number of the feeding side is 10-150, preferably 60-100; the theoretical plate number of the discharging side is 10-150, preferably 60-100; the theoretical plate number of the top of the partition board is 10-60, preferably 20-40; the theoretical number of the partition plates is 10-50, preferably 20-30.
The impurity removing tower adopts a plate tower or a packed tower, and the theoretical plate number is 5-60, preferably 10-40.
According to the research of the invention, in the prior art, the purity requirement of cyclohexanone is higher, but the purity requirement of cyclohexanol is not higher, the bottom of the tower basically has no index requirement, but a small tower with a plurality of reduced tower plates is embedded at the bottom of the alcohol tower, the material at the bottom of the main tower overflows into the small tower to be heated and distilled, and the external throwing amount of heavy components is controlled by controlling the temperature of the small tower kettle. Therefore, the physical properties of cyclohexanol and cyclohexanone are accurately mastered, and the verification of the existing industrial operation data is assisted, and the separation of alcohol, ketone and heavy components by utilizing a stream of cold and heat in a bulkhead tower by an industrial device is realized by establishing a simulation model for separating crude alcohol ketone by the bulkhead tower.
The partition tower is characterized in that a vertical partition plate is arranged in the rectifying tower, so that a single tower can realize the functions of two towers. The dividing wall divides the column into a prefractionation section, a main fractionation section, a common overhead rectification section, and a bottom stripping section. The multicomponent mixture is fed to the prefractionation section, the top product is withdrawn from the common rectification section, the bottom product is withdrawn from the common stripping section, and the intermediate product is withdrawn as a side stream from the main fractionation section, allowing for efficient separation between the three components with similar relative volatilities and steady operating pressure within the column. By adopting the partition tower technology, one rectifying tower and auxiliary equipment, including a reboiler, a condenser, a reflux tank, a reflux pump, a control system and the like, are saved, the equipment investment is reduced, and the occupied area is reduced. The partition tower technology can strengthen the heat and mass transfer process, improve the thermodynamic efficiency, avoid the back mixing effect of intermediate components, reduce the back mixing caused by different compositions at the feeding plate, and the like, so that the energy consumption of the device can be greatly reduced.
The separation of cyclohexanone, cyclohexanol and heavy components is integrated in one tower by utilizing a partition tower technology, cyclohexanone is extracted from the tower top, cyclohexanol is extracted from the side line, and intermediate components of ethers and heavy substances are extracted from the tower bottom.
According to the invention, when the separation wall tower technology is adopted to separate crude alcohol ketone, under similar tower top operation pressure, the reflux ratio of the tower top and the reflux in the tower are larger than those of the alcohol tower, at the moment, the operation temperature of the tower bottom of the separation wall tower is lower than that of the main alcohol tower bottom of the existing industrial process by 15 ℃ and lower than that of the embedded small tower bottom by 40 ℃, the separation precision is greatly improved, and the ether intermediate components which are easy to be entrained into the product cyclohexanol originally can be pressed into heavy substances in the tower bottom to be discharged, so that the ether intermediate components in the side line cyclohexanol are ensured to be much lower than those in the existing industrial process; the material of the partition tower kettle containing a large amount of cyclohexanol directly enters the positive pressure rectifying tower, the relative volatility of the ether intermediate components is lower than that of the cyclohexanol under the positive pressure condition, the ether intermediate components are continuously removed along with heavy matters while the cyclohexanol is recovered, the accumulation phenomenon of the ether intermediate components in a crude alcohol ketone refining system and the increased material consumption and energy consumption are eliminated, the cyclohexanol extracted from the side line of the discharging side of the partition tower and the cyclohexanol extracted from the top of the impurity removing tower are combined, the process of removing the ether intermediate components is not required, the purity quality requirement of the dehydrogenation reaction on alcohol is met, and the material can be directly used as the feed of a dehydrogenation reactor.
Compared with the prior art, the invention has the beneficial effects that:
1. the separation of cyclohexanone, cyclohexanol, intermediate ether components and heavy components is carried out in one tower by adopting a partition tower technology, so that the high-efficiency separation of alcohol and ketone is realized, and the reboilers, coolers, reflux tanks and the like of the cyclohexanone and cyclohexanol separation towers required by the traditional process are integrated into one set, thereby avoiding the secondary vaporization and secondary condensation of materials, saving more than 29 percent of energy consumption, reducing equipment investment and reducing occupied area.
And 2, controlling the cyclohexanol content in heavy components of the tower kettle by adopting the operation temperature of 109-120 ℃ of a partition tower kettle, which is lower than the operation temperature of 116-130 ℃ of the tower kettle in the existing process by more than 15 ℃ and lower than the operation temperature of 150-165 ℃ of an embedded small tower kettle by more than 40 ℃, so that intermediate ether components which are difficult to remove easily enter the heavy components.
3. The characteristic that the volatility of the intermediate ether component is lower than that of cyclohexanol under the positive pressure operation condition is utilized, the temperature of the tower bottom of the impurity removal tower is 170-205 ℃, the temperature of the tower bottom of the impurity removal tower is over 20 ℃ higher than that of the tower bottom of the existing small flow process, and the theoretical plate number is over 3 times higher, so that the ether intermediate impurities are continuously thrown out of the system together with heavy matters through the tower bottom only when a small amount of cyclohexanol is recovered, the accumulation phenomenon of the ether intermediate components in a crude alcohol ketone refining system and the increased material consumption and energy consumption are eliminated, and the purity of dehydrogenation feeding is ensured.
4. In the existing process, the small tower and the main separation tower are integrated, and the ether intermediate components in the cyclohexanol cannot be removed and are accumulated in the system continuously due to the limitation of the operation pressure of the main tower and the operation temperature of the small tower. The invention changes the small towers which are arranged at the bottom of the cyclohexanol separating tower and the cyclohexanol main separating tower in the existing cyclohexanol separating tower process flow under the same negative pressure operation condition into independent ones, and takes the hot discharge of the separating wall tower kettle as the feed, thereby ensuring the stable operation of the separating wall tower, realizing the on-line flexible removal of intermediate ether components in cyclohexanol under the positive pressure operation condition by the operation pressure of the impurity removing tower, and ensuring the recovery of cyclohexanol.
5. The invention reduces the temperature during the separation of alcohol and ketone and the distillation times of cyclohexanol, thereby effectively reducing the loss of cyclohexanone and cyclohexanol and improving the yield of alcohol and ketone of the device.
Drawings
Fig. 1 is a process flow chart according to the present invention.
Wherein, 1, a light component removing tower is used for coarse alcohol ketone, 2, a partition tower, 21, a vertical partition plate, 22, a feeding side, 23, a discharging side, 3, cyclohexanone products, 4, a side line is used for extracting cyclohexanol, 5, an intermediate ether component containing cyclohexanol and heavy matters, 6, a impurity removing tower, 7, a tower top is used for extracting cyclohexanol, 8, an intermediate ether component and heavy matters.
Fig. 2 is a conventional process flow diagram in contrast to the present invention.
Description of the embodiments
The invention will be further described with reference to the drawings and the specific examples. The following description is merely exemplary in nature and is in no way intended to limit the scope of the invention and its application.
As shown in figure 1, the method for efficiently separating cyclohexanone and removing impurities in cyclohexanol comprises the following process flows: the crude alcohol ketone 1 at the bottom of the light component removal tower enters a partition tower 2, cyclohexanone 3 is extracted from the top of the partition tower 2, cyclohexanol 4 is extracted from the side line, intermediate ether components containing cyclohexanol and heavy matters 5 extracted from the tower bottom enter a impurity removal tower 6, the intermediate ether components and heavy matters 8 are removed on line from the bottom of the impurity removal tower 6, and cyclohexanol 7 extracted from the top of the impurity removal tower 6 and cyclohexanol 4 extracted from the side line of the partition tower 2 are combined and then discharged from the device.
The vertical partition plate 21 is arranged in the axial middle position in the partition wall tower 2, the partition wall tower is divided into a feeding side 22 and a discharging side 23, the crude alcohol ketone 1 from the light component removing tower bottom enters the feeding side 22 of the partition wall tower 2, part of the condensed gas phase at the tower top of the partition wall tower 2 flows back to the tower top of the partition wall tower 2, and the rest part of the condensed gas phase is taken as cyclohexanone product 3.
A liquid collecting tank is arranged between the inner member at the top of the partition wall tower 2 and the vertical partition plate 21, and liquid in the liquid collecting tank is respectively and internally refluxed to the inner member at the top of the feeding side 22 and the discharging side 23 through a distributor, so that equipment investment can be saved by adopting an internal reflux mode, and the operation process control is convenient without externally arranging a reflux pump.
And after the side line of the discharging side 22 of the partition tower 2 is combined with the side line of the cyclohexanol 4 of the tower top of the impurity removal tower 6, the side line of the cyclohexanol 7 is directly used as the feed of the dehydrogenation reactor without the process of removing the intermediate components of ethers.
Example 1
The alcohol-ketone separation of the device for producing cyclohexanone by using the oxidation method of cyclohexane with annual yield of 15 ten thousand tons adopts the high-efficiency separation and impurity removal process flow, the partition tower adopts regular packing, and the impurity removal tower adopts a plate tower, as shown in figure 1.
The crude alcohol ketone from the bottom of the light component removal tower enters the feeding side of the partition tower, the feeding amount is 40t/h, and the feeding composition comprises 42w% of cyclohexanol, 51.7w% of cyclohexanone, 5.1w% of intermediate component and 0.3w% of heavy component. The operation pressure of the top of the partition wall is 3KPaA, the operation temperature is 55 ℃, the gas phase of the top of the tower is cooled by a condenser, one part of the gas phase of the top of the tower is refluxed to the top of the tower, the reflux ratio of the top of the tower is 3.5, and the other part of the gas phase of the top of the tower is 20.5t/h, and the mass fraction of the cyclohexanone product is more than or equal to 99.95%; the internal reflux ratio of the liquid collecting tanks above the feeding side and the discharging side is 1:2, the mass fraction of cyclohexanol produced by the side line of the dividing wall tower is more than or equal to 93.75 percent (and the total mass of cyclohexanol is 18.5 tons after the top of the impurity removing tower is converged, the mass fraction of cyclohexanol is about 93.41 percent, wherein, the mass fraction of cyclohexanone is 0.34 percent, the mass fraction of butylcyclohexyl ether is 4.51 percent, the mass fraction of pentylcyclohexane is 1.31 percent, and the mass fraction of other components is 0.43 percent); the operation pressure of the partition tower kettle is 11KPaA, the operation temperature is 103 ℃, and the partition tower kettle extracts the intermediate component and the heavy component of the ethers containing cyclohexanol which are 2.86t/h, wherein the cyclohexanol content is 45%. The operation pressure of the tower top for removing impurities is 108KPaA, the operation temperature is 166 ℃, the reflux ratio is 0.6, the quantity of cyclohexanol recovered from the tower top is 2.0t/h, the mass fraction of cyclohexanol is more than or equal to 88%, the operation pressure of the tower bottom is 129KPaA, the operation temperature is 201 ℃, the thrown-out intermediate components and heavy components of ethers are about 0.87t/h, and the mass fraction of the intermediate components and the heavy components is more than or equal to 80%. The theoretical plates of the partition tower are 132, the feeding position is positioned at the 75 th theoretical plate, and the lateral line extraction is positioned at the 75 th theoretical plate; the theoretical plates of the impurity removal tower are 24, and the feeding position is positioned on the 1 st theoretical plate. The steam consumption is 17t/h by adopting the method.
Comparative example 1
If the process flow of fig. 2 is adopted, the operation pressure of the ketone tower top is 3KPaA, the operation temperature is 55 ℃, the operation pressure of the tower kettle is 9KPaA, the operation temperature is 99 ℃ and the reflux ratio of the tower top is 3 under the same feeding amount and composition as in the example 1; the operating pressure of the alcohol tower top is 6KPaA, the operating temperature is 86 ℃, the reflux ratio of the tower top is 0.95, the operating pressure of the tower kettle is 17KPaA, the operating temperature of the main tower kettle of the alcohol tower is 119 ℃, the operating temperature of the embedded small tower kettle is 156 ℃, and the operating pressure is 21KPaA. The mass fraction of the cyclohexanone product extracted from the top of the ketone tower is 20.6t/h, which is more than or equal to 99.95 percent, the mass fraction of the cyclohexanol product extracted from the top of the alcohol tower is 18.2t/h, the mass fraction of the cyclohexanol is about 90.18 percent (wherein, the cyclohexanone is 1.34 percent, the butyl cyclohexyl ether is 6.23 percent, the amyl cyclohexane is 1.68 percent and the other components are 0.57 percent), the mass fraction of the intermediate component and the heavy component extracted from the bottom of the tower is about 1.1t/h, and the mass fraction of the intermediate component and the heavy component is more than or equal to 95 percent. Under the process, the ether intermediate components entrained in the cyclohexanol can not be continuously discharged out of the device, and can gradually accumulate to 10% or even 12% along with the long-period running of the device, so that the energy consumption and the material consumption of the crude alcohol ketone refining device are increased; there is also a further distillation of cyclohexanol, 10% of the total feed, before it enters the dehydrogenation reactor, to remove these intermediate ethers components, which is significantly more energy-intensive than the present invention.
Compared with the invention, the consumption steam amount of the cyclohexanone tower in the prior process flow is 14.5t/h, the consumption steam amount of the cyclohexanol tower is 6.5t/h, the total consumption steam amount is 21t/h, and the consumption steam amount is 4t/h higher than the consumption steam amount of 17t/h in the prior process flow; the intermediate components of ethers are also higher than the invention by nearly 3 percent, and can accumulate to about 10 percent in the system, and the invention can maintain about 5 percent.
Example 2
The alcohol-ketone separation of the device for producing cyclohexanone by using the oxidation method of cyclohexane with annual yield of 15 ten thousand tons adopts the high-efficiency separation and impurity removal process flow, the partition tower adopts regular packing, and the impurity removal tower adopts a plate tower, as shown in figure 1.
The crude alcohol ketone from the bottom of the light component removal tower enters the feeding side of the partition tower, the feeding amount is 44t/h, and the feeding composition comprises 44.34w% of cyclohexanol, 51.20w% of cyclohexanone, 3.5w% of intermediate component and 0.9w% of heavy component. The operation pressure of the top of the partition wall is 4KPaA, the operation temperature is 56 ℃, the gas phase of the top of the tower is cooled by a condenser, one part of the gas phase of the top of the tower is refluxed to the top of the tower, the reflux ratio of the top of the tower is 3.8, and the other part of the gas phase of the top of the tower is 22.7t/h, and the mass fraction of the cyclohexanone product is more than or equal to 99.96%; the internal reflux ratio of the liquid collecting tray above the feeding side and the discharging side is 1:2, the mass fraction of cyclohexanol produced by the side line of the dividing wall tower is more than or equal to 94.24 percent (and the total mass of cyclohexanol is 20.26 tons after the cyclohexanol is collected and converged at the top of the impurity removing tower, wherein the mass fraction of cyclohexanone is about 93.46 percent, and the cyclohexanone is 0.53 percent, the butylcyclohexyl ether is 3.74 percent, the pentylcyclohexane is 1.57 percent, and the other components are 0.72 percent); the operation pressure of the partition tower kettle is 13KPaA, the operation temperature is 105 ℃, the partition tower kettle extracts the intermediate component and the heavy component of the ethers containing cyclohexanol which are 4.01t/h, wherein the content of cyclohexanol is 74.4%. The operation pressure of the tower top for removing impurities is 105KPaA, the operation temperature is 163 ℃, the reflux ratio is 0.2, the quantity of cyclohexanol recovered from the tower top is 3.21t/h, the mass fraction of cyclohexanol is more than or equal to 89%, the operation pressure of the tower bottom is 125KPaA, the operation temperature is 193 ℃, the thrown-out intermediate components and heavy components of ethers are about 1.04t/h, and the mass fraction of the intermediate components and the heavy components is more than or equal to 84%. The theoretical plates of the partition tower are 132, the feeding position is positioned on the 70 th theoretical plate, and the side line extraction is positioned on the 70 th theoretical plate; the theoretical plates of the impurity removal tower are 15, and the feeding position is positioned on the 6 th theoretical plate. The steam consumption is 18.8t/h by adopting the method.
Comparative example 2
If the process flow of fig. 2 is adopted, the operation pressure of the ketone tower top is 3KPaA, the operation temperature is 55 ℃, the operation pressure of the tower kettle is 9KPaA, the operation temperature is 101 ℃ and the reflux ratio of the tower top is 3.5 under the same feeding amount and composition as in the example 2; the operating pressure of the alcohol tower top is 5KPaA, the operating temperature is 87 ℃, the reflux ratio of the tower top is 1.15, the operating pressure of the tower kettle is 18KPaA, the operating temperature of the main tower kettle of the alcohol tower is 121 ℃, the operating temperature of the embedded small tower kettle is 161 ℃, and the operating pressure is 22KPaA. The mass fraction of the cyclohexanone product extracted from the top of the ketone tower is more than or equal to 99.97%, the mass fraction of the cyclohexanol product extracted from the top of the alcohol tower is 21.6t/h, the mass fraction of the cyclohexanol is about 91.18% (wherein, 1.25% of cyclohexanone, 5.43% of butyl cyclohexyl ether, 1.34% of amyl cyclohexane and 0.8% of other components) and the mass fraction of the intermediate component and heavy component extracted from the bottom of the tower is about 0.92t/h, and the mass fraction of the intermediate component and heavy component is more than or equal to 75%. Under this scheme, the intermediate components of ethers in cyclohexanol gradually accumulate up to 10% and even up to 12% with long period operation of the apparatus, and it is necessary to further withdraw cyclohexanol 10% of the total feed before cyclohexanol enters the dehydrogenation reactor and distill to remove these intermediate components of ethers, which is significantly more energy-consuming than the present invention. In the existing process flow, the consumption steam amount of the cyclohexanone tower is 16.3t/h, the consumption steam amount of the cyclohexanol tower is 9.2t/h, and the total consumption steam amount is 25.5t/h.
Compared with the invention, the consumption steam amount of the cyclohexanone tower in the prior process flow is 16.3t/h, the consumption steam amount of the cyclohexanol tower is 9.2t/h, the total consumption steam amount is 25.5t/h, and the consumption steam amount is 6.7t/h higher than that of the cyclohexanone tower in the prior process flow of 18.8 t/h; the intermediate components of ethers are also higher than the invention by nearly 3 percent, and can accumulate to about 10 percent in the system, and the invention can maintain about 6 percent.
Claims (5)
1. A method for efficiently separating cyclohexanone and removing impurities in cyclohexanol is characterized in that: feeding crude alcohol ketone from the bottom of the light component removal tower into a partition tower, extracting cyclohexanone product from the top of the partition tower, extracting cyclohexanol from the side line, feeding intermediate ether components and heavy matters containing cyclohexanol from the tower kettle into a impurity removal tower, continuously removing the intermediate ether components and the heavy matters from the bottom of the impurity removal tower, and directly taking the cyclohexanol from the top of the impurity removal tower and the cyclohexanol from the side line of the partition tower as the feed of a dehydrogenation reactor after being combined;
a vertical baffle is arranged in the axial middle position in the partition tower, the partition tower is divided into a feeding side and a discharging side, crude alcohol ketone from the light component removal tower bottom enters the feeding side of the partition tower, part of the condensed gas phase at the top of the partition tower flows back to the top of the partition tower, and the rest part of the condensed gas phase is taken as cyclohexanone product to be extracted;
the tower top operation temperature of the partition wall tower is 45-65 ℃, the operation pressure is 2 KPaA-8 KPaA, the reflux ratio is 2-5, the internal reflux from the liquid collecting box to the feeding side and the discharging side is 1/3-1/2, 1/2-2/3 respectively, the tower kettle operation temperature is 100-120 ℃, and the operation pressure is 8 KPaA-15 KPaA;
the operating temperature of the tower top of the impurity removal tower is 150-185 ℃, the operating pressure is normal pressure-100 KPaG, the reflux ratio is 0-2, the operating temperature of the tower kettle is 170-220 ℃, and the operating pressure is 100 KPaG-200 KPaG;
a liquid collecting tank is arranged between the inner member at the top of the partition wall tower and the vertical partition plate, and liquid in the liquid collecting tank flows back to the inner members at the tops of the feeding side and the discharging side respectively through a distributor;
the theoretical plates of the impurity removal tower are 10-40.
2. The method for efficiently separating cyclohexanone and removing impurities from cyclohexanol according to claim 1, wherein: the impurity removing tower is operated under normal pressure or under pressure.
3. The method for efficiently separating cyclohexanone and removing impurities from cyclohexanol according to claim 1, wherein: the partition tower adopts a plate tower or a packed tower, and the theoretical plate number at the feeding side is 10-150; the theoretical plate number of the discharging side is 10-150; the theoretical plate number of the top of the partition board is 10-60; the theoretical plate number of the partition plate bottom is 10-50.
4. A method for efficiently separating cyclohexanone and removing impurities from cyclohexanol according to claim 3, wherein: the theoretical plate number of the feeding side is 60-100; the theoretical plate number of the discharging side is 60-100; the theoretical plate number of the top of the partition board is 20-40; the theoretical plate number of the partition plate bottom is 20-30.
5. The method for efficiently separating cyclohexanone and removing impurities from cyclohexanol according to claim 1, wherein: the impurity removing tower adopts a plate tower or a packed tower.
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