CN116999881A - Preparation method and preparation device for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol - Google Patents
Preparation method and preparation device for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol Download PDFInfo
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- CN116999881A CN116999881A CN202310950458.2A CN202310950458A CN116999881A CN 116999881 A CN116999881 A CN 116999881A CN 202310950458 A CN202310950458 A CN 202310950458A CN 116999881 A CN116999881 A CN 116999881A
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- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 title claims abstract description 67
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 33
- 238000003860 storage Methods 0.000 claims abstract description 16
- 238000002425 crystallisation Methods 0.000 claims abstract description 9
- 230000008025 crystallization Effects 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 238000002844 melting Methods 0.000 claims abstract description 9
- 230000008018 melting Effects 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims description 38
- 238000010992 reflux Methods 0.000 claims description 35
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000007599 discharging Methods 0.000 claims description 18
- RLMZELPHRPTNJX-UHFFFAOYSA-N 2,4-dioctylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(CCCCCCCC)=C1 RLMZELPHRPTNJX-UHFFFAOYSA-N 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 238000005804 alkylation reaction Methods 0.000 claims description 11
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 10
- 239000012295 chemical reaction liquid Substances 0.000 claims description 5
- 239000012535 impurity Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000010583 slow cooling Methods 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 7
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- 230000000630 rising effect Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 239000000110 cooling liquid Substances 0.000 description 3
- 230000017105 transposition Effects 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/10—Vacuum distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/02—Crystallisation from solutions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of p-tert-butylphenol rectification and crystallization co-production of p-tert-butylphenol, and particularly relates to a preparation method and a preparation device for p-tert-butylphenol rectification and crystallization co-production of p-tert-butylphenol. The preparation device used in the preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol comprises a first-stage rectifying tower, wherein the first-stage rectifying tower is connected with a second-stage rectifying tower through a first-stage rectifying tower discharge pump, the second-stage rectifying tower is connected with a circulating buffer tank through a mixed component temporary storage tank, the circulating buffer tank is connected with a crystallizer through a circulating pump, and the crystallizer is connected with a third-stage rectifying tower through a third-stage rectifying tower inlet pipeline. According to the method, the recovered p-tert-octyl phenol enters a continuous melting crystallizer, impurities such as isomers and the like are extracted step by step, and then rectification is carried out, so that the purity of the product can reach more than 99.9%, and meanwhile, the color change of the p-tert-octyl phenol is improved.
Description
Technical Field
The invention belongs to the technical field of p-tert-butylphenol rectification and crystallization co-production of p-tert-butylphenol, and particularly relates to a preparation method and a preparation device for p-tert-butylphenol rectification and crystallization co-production of p-tert-butylphenol.
Background
P-tert-octylphenol, also known as p-tert-octylphenol, is a raw material and an intermediate for fine chemical engineering, and is widely used for synthesizing octylphenol formaldehyde resin, nonionic surfactant and the like. In workshop production, because the p-tert-octyl phenol is often produced with isomers in the synthesis process, the melting boiling points of the isomers are similar to those of the p-tert-octyl phenol, and the problem that the product content cannot reach more than 99.9% purity due to separate rectification without separation exists.
Patent application CN113072429a, publication time 2021.07.06. The p-tert-octyl phenol continuous production process comprises the steps of continuously introducing phenol and diisobutylene into a mixer respectively, allowing mixed materials to enter a first-stage reaction kettle from the bottom of the first-stage reaction kettle for catalytic reaction, continuously discharging the materials from the upper part of the first-stage reaction kettle after the catalytic reaction reaches a certain liquid level, allowing the materials to enter a second-stage reaction kettle from the bottom of the second-stage reaction kettle for transposition reaction, continuously discharging the materials from the upper part of the second-stage reaction kettle after the catalyst is continuously transposed, and obtaining p-tert-octyl phenol alkylation liquid, and sequentially introducing the p-tert-octyl phenol alkylation liquid into a first-stage light removal tower, a second-stage light removal tower and a heavy removal tower for rectification and purification to obtain p-tert-octyl phenol. But the purity of the synthesized p-tert-octyl phenol can not reach 99.9 percent.
In summary, the prior art can produce p-tert-octylphenol with higher purity, but the purity can not reach more than 99.9%, and the requirement of downstream clients can not be met; and co-production of p-tert-butylphenol cannot be achieved.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol, wherein the recovered p-tert-octylphenol is fed into a continuous melting crystallizer, and impurities such as isomers and the like are extracted step by step and then rectified, so that the purity of the product can reach more than 99.9%, and the color change of the p-tert-octylphenol is improved.
The invention further aims to provide a preparation device for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol, and the product purity is greatly improved by adding a melt crystallizer, so that the device is beneficial to industrial production.
The technical scheme adopted by the invention is as follows:
the preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol comprises the following steps:
(1) Introducing the alkylation reaction liquid into a first-stage rectifying tower, extracting light-component phenol from the tower top, extracting o-octyl phenol, p-tert-butyl phenol, p-tert-octyl phenol isomer, 2,4 dioctyl phenol from the tower bottom, and then introducing the light-component phenol into a second-stage rectifying tower;
(2) Performing reduced pressure distillation in a secondary rectifying tower, extracting mixed components of o-octyl phenol and p-tert-butyl phenol from the tower top, extracting mixed components of p-tert-octyl phenol, p-tert-octyl phenol isomers and 2,4 dioctyl phenol from the tower bottom, entering a circulating buffer tank, then entering a crystallizer through a circulating pump, and after treatment in the crystallizer is completed, entering a tertiary rectifying tower;
(3) And (3) carrying out reduced pressure distillation in a three-stage rectifying tower, extracting p-tert-octyl phenol from the tower top, and extracting 2,4 dioctyl phenol from the tower bottom.
In the step (1), the temperature of the top of the primary rectifying tower is 95-105 ℃, the vacuum degree of the top of the tower is-0.09-0.096 MPa, the temperature of the bottom of the tower is 175-183 ℃, the vacuum degree of the bottom of the tower is-0.8-0.085 MPa, and internal reflux is adopted, wherein the reflux ratio is (1-2): 1.
in the step (2), the top temperature of the secondary rectifying tower is 128-132 ℃, the top vacuum degree is-0.092-0.098 MPa, the bottom temperature is 183-187 ℃, the bottom vacuum degree is-0.088-0.092 MPa, and the internal reflux and the reflux ratio (2-3) are adopted: 1.
the crystallizer in the step (2) is a melting crystallizer, the initial temperature in the crystallizer is 45-55 ℃, the heating rate is 4-6 ℃/min, the end temperature is 79-81 ℃, and then the temperature is reduced and extracted.
In the step (3), the top temperature of the three-stage rectifying tower is 148-152 ℃, the top vacuum degree is-0.096-0.098 MPa, the bottom temperature is 188-191 ℃, the bottom vacuum degree is-0.090-0.094 MPa, and the internal reflux is adopted, wherein the reflux ratio is 1:1.
The preparation device used in the preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol comprises a first rectifying tower, wherein the first rectifying tower is connected with a second rectifying tower through a first rectifying tower discharge pump, the second rectifying tower is connected with a circulating buffer tank through a mixed component temporary storage tank, the circulating buffer tank is connected with a crystallizer through a circulating pump, the crystallizer is connected with a third rectifying tower through a third rectifying tower inlet pipeline, a p-tert-octylphenol storage tank is connected to the third rectifying tower, and a feeding pipeline is connected to the first rectifying tower.
The light component storage tank is connected to the first-stage rectifying tower, a first-stage rectifying tower discharging pipeline is connected between the first-stage rectifying tower and the first-stage rectifying tower discharging pump, a second-stage rectifying tower discharging pipeline is arranged at the bottom of the second-stage rectifying tower, and a third-stage rectifying tower bottom discharging pipeline is arranged at the bottom of the third-stage rectifying tower.
The mixed component temporary storage tank is connected with the heat exchanger through the heat exchange pump, the heat exchanger is connected with the crystallizer, and a light material discharging pipeline is arranged on the crystallizer.
The circulating pump return pipeline is connected with a three-stage rectifying tower inlet pipeline through a tee joint, the three-stage rectifying tower inlet pipeline is connected with a three-stage rectifying tower, and a sampler is arranged on the three-stage rectifying tower inlet pipeline.
The primary rectifying tower is connected with the primary vacuumizing pump through a primary rectifying tower vacuumizing pipeline, the secondary rectifying tower is connected with the secondary vacuumizing pump through a secondary rectifying tower vacuumizing pipeline, and the tertiary rectifying tower is connected with the tertiary vacuumizing pump through a tertiary rectifying tower vacuumizing pipeline.
The crystallizer is internally provided with a heating box, a slow cooling box, a first-stage standing box and a second-stage standing box, a heating coil is arranged in the heating box, a product slow cooling coil is arranged in the slow cooling box, a crystallizer feed inlet is arranged at the upper and lower sides of the heating box, a heat exchanger outlet pipeline and a heat exchange pump inlet pipeline are connected to the heating coil, a slow cooling box inlet pipeline and a cooling liquid outlet slow cooling box pipeline are connected to the slow cooling box, a heating box first discharge port, a heating box second discharge port and a heating box third discharge port are sequentially arranged on the vertical wall of the heating box from top to bottom, the heating box first discharge port, the heating box second discharge port and the heating box third discharge port are all connected with the product slow cooling coil through pipelines, the product slow cooling coil is connected with a feeding and standing box pump, the feeding and standing box pump is connected with the first-stage standing box, and the feeding and standing box pump is connected with the second-stage standing box. An isomer discharge port and a product discharge port are arranged on the vertical wall of the first-stage standing box, the isomer discharge port is connected with a light material discharge pipeline, and the product discharge port is connected with a circulating buffer tank pipeline.
The device slowly heats the product from bottom to top in the heating box by introducing the crystallizer, and the heat conducting oil in the heating coil heats the product from top to bottom, so that the heat conducting oil and the heat conducting oil are opposite to each other, and the heat transfer efficiency and the heating stability are greatly improved. Under the condition that the flow rates of the heat conducting oil and the product are unchanged, the influence of the external temperature on the crystallizer is the greatest, particularly in summer and winter in the north, the temperature difference can reach more than 50 ℃, and the stability of melting crystallization is greatly influenced, so that the discharge ports of a plurality of heating boxes are arranged, the heights of the discharge ports are different, the discharge temperatures are different, and the discharge ports can be automatically determined by the external temperature. The product after temperature rising is introduced into the product slow cooling coil pipe, and the coil pipe is filled with low-temperature liquid with specified temperature, so that the product is slowly cooled, and is sent to a standing box after temperature reduction, isomers are discharged from the upper part, and the required product is discharged from the lower part.
Compared with the prior art, the invention has the following beneficial effects:
(1) The obtained p-tert-octyl phenol enters a continuous melting crystallizer, impurities such as isomers and the like are extracted step by step, and then rectification is carried out, so that the purity of the product can reach more than 99.9%, and the color change of the p-tert-octyl phenol is improved.
(2) By adding the melting crystallizer, the purity of the product is greatly improved, and the method is favorable for industrial production.
Drawings
FIG. 1 is a schematic diagram of a device for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol according to the present invention;
FIG. 2 is a schematic structural view of the crystallizer according to the present invention;
in the figure: 1. a first-stage rectifying tower; 2. a second-stage rectifying tower; 3. a crystallizer; 4. a three-stage rectifying tower; 5. a feed conduit; 6. a light component storage tank; 7. a mixed component temporary storage tank; 8. p-tert-octylphenol storage tank; 9. vacuumizing a pipeline of the primary rectifying tower; 10. vacuumizing a pipeline of the secondary rectifying tower; 11. vacuumizing pipelines of the three-stage rectifying tower; 12. a primary vacuumizing pump; 13. a secondary vacuumizing pump; 14. a three-stage vacuumizing pump; 15. a first-stage rectifying tower discharging pipeline; 16. a first-stage rectifying tower discharge pump; 17. a discharge pipeline of the secondary rectifying tower; 18. a circulation buffer tank; 19. a circulation pump; 20. feeding into a three-stage rectifying tower pipeline; 21. a light material discharging pipeline; 22. a sampler; 23. a pipeline for feeding the circulating buffer tank; 24. a heat exchange pump; 25. a heat exchanger; 26. a discharging pipeline at the bottom of the three-stage rectifying tower; 27. a pipeline for feeding the circulating buffer tank; 28. a crystallizer feed inlet; 29. a heat pump inlet and exchange pipeline; 30. a heat exchanger outlet pipe; 31. a heating box; 32. a slow cooling box; 33. a first-stage standing box; 34. a second-stage standing box; 35. heating coil pipe; 36. a coil pipe for slowly cooling the product; 37. a static tank pump is arranged; 38. feeding into a slow cooling box pipeline; 39. the cooling liquid is discharged from the slow cooling box pipeline; 40. a first discharge port of the heating box; 41. a second discharge port of the heating box; 42. a third discharge port of the heating box; 43. the circulation pump returns to the pipeline.
Detailed Description
The invention is further illustrated below with reference to examples, which are not intended to limit the practice of the invention.
Example 1
As shown in figures 1-2, the preparation device used in the preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-butylphenol comprises a first rectifying tower 1, wherein the first rectifying tower 1 is connected with a second rectifying tower 2 through a first rectifying tower discharging pump 16, the second rectifying tower 2 is connected with a circulating buffer tank 18 through a mixed component temporary storage tank 7, the circulating buffer tank 18 is connected with a crystallizer 3 through a circulating pump 19, the crystallizer 3 is connected with a third rectifying tower 4 through a third rectifying tower inlet pipeline 20, a p-tert-octylphenol storage tank 8 is connected on the third rectifying tower 4, and a feeding pipeline 5 is connected on the first rectifying tower 1. The light component storage tank 6 is connected to the primary rectifying tower 1, the primary rectifying tower discharge pipeline 15 is connected between the primary rectifying tower 1 and the primary rectifying tower discharge pump 16, the secondary rectifying tower 17 is arranged at the bottom of the secondary rectifying tower 2, and the tertiary rectifying tower 26 is arranged at the bottom of the tertiary rectifying tower 4. A circulating buffer tank feeding pipeline 27 is arranged between the mixed component temporary storage tank 7 and the circulating buffer tank 18, a circulating pump return pipeline 43 is arranged between the circulating pump 19 and the crystallizer 3, a circulating buffer tank feeding pipeline 23 is arranged between the crystallizer 3 and the circulating buffer tank 18, the crystallizer 3 is connected with a heat exchanger 25 through a heat exchange pump 24, the heat exchanger 25 is connected with the crystallizer 3, and a light material discharging pipeline 21 is arranged on the crystallizer 3. The circulating pump return pipeline 43 is connected with a third-stage rectifying tower inlet pipeline 20 through a tee joint, the third-stage rectifying tower inlet pipeline 20 is connected with the third-stage rectifying tower 4, and a sampler 22 is arranged on the third-stage rectifying tower inlet pipeline 20. The primary rectifying tower 1 is connected with a primary vacuumizing pump 12 through a primary rectifying tower vacuumizing pipeline 9, the secondary rectifying tower 2 is connected with a secondary vacuumizing pump 13 through a secondary rectifying tower vacuumizing pipeline 10, and the tertiary rectifying tower 4 is connected with a tertiary vacuumizing pump 14 through a tertiary rectifying tower vacuumizing pipeline 11.
The crystallizer 3 is internally provided with a heating box 31, a slow cooling box 32, a first-stage standing box 33 and a second-stage standing box 34, a heating coil 35 is arranged in the heating box 31, a product slow cooling coil 36 is arranged in the slow cooling box 32, a crystallizer feed inlet 28 is arranged above and below the heating box 31, a heat exchanger outlet pipeline 30 and a heat pump inlet pipeline 29 are connected to the heating coil 35, a slow cooling box inlet pipeline 38 and a cooling liquid outlet slow cooling box pipeline 39 are connected to the slow cooling box 32, a heating box first discharge port 40, a heating box second discharge port 41 and a heating box third discharge port 42 are sequentially arranged on the standing wall of the heating box 31 from top to bottom, the heating box first discharge port 40, the heating box second discharge port 41 and the heating box third discharge port 42 are all connected with the product slow cooling coil 36 through pipelines, the product slow cooling coil 36 is connected with a stewing box inlet pump 37, the stewing box inlet pump 37 is connected with the first-stage standing box 33, and the stewing box inlet pump 37 is connected with the second-stage standing box 34. An isomer discharge port and a product discharge port are arranged on the vertical wall of the primary standing box 33, the isomer discharge port is connected with a light material discharge pipeline, and the product discharge port is connected with a circulating buffer tank pipeline.
Example 2
This example was prepared by the preparation apparatus used in the preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol as described in example 1.
The preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol comprises the following steps:
(1) Introducing the alkylation reaction liquid into a first-stage rectifying tower, extracting light-component phenol from the tower top, extracting o-octyl phenol, p-tert-butyl phenol, p-tert-octyl phenol isomer and 2,4 dioctylphenol from the tower bottom, then introducing the light-component phenol into a second-stage rectifying tower, wherein the temperature of the tower top of the first-stage rectifying tower is 100 ℃, the vacuum degree of the tower top is-0.094 MPa, the temperature of the tower bottom is 180 ℃, the vacuum degree of the tower bottom is-0.083 MPa, and adopting internal reflux and the reflux ratio is 2:1;
(2) Performing reduced pressure distillation in a secondary rectifying tower, extracting mixed components of o-octyl phenol and p-tert-butyl phenol from the tower top, extracting mixed components of p-tert-octyl phenol, p-tert-octyl phenol isomer and 2,4 dioctyl phenol from the tower bottom, feeding tower bottom liquid into a circulating buffer tank, feeding the circulating buffer tank into a crystallizer, and feeding the circulating buffer tank into a tertiary rectifying tower after finishing treatment in the crystallizer, wherein the temperature of the tower top of the secondary rectifying tower is 130 ℃, the vacuum degree of the tower top is-0.094 MPa, the vacuum degree of the tower bottom is 185 ℃, the vacuum degree of the tower bottom is-0.09 MPa, and internal reflux is adopted, and the reflux ratio is 3:1;
the initial temperature in the crystallizer is 50 ℃, the heating rate is 4 ℃/min, the end temperature is 81 ℃, and then the temperature is reduced and extracted;
(3) And (3) carrying out reduced pressure distillation in a three-stage rectifying tower, wherein p-tert-octyl phenol is extracted from the tower top, 2,4 dioctyl phenol is extracted from the tower bottom, the temperature of the tower top of the three-stage rectifying tower is 152 ℃, the vacuum degree of the tower top is-0.097 MPa, the temperature of the tower bottom is 191 ℃, the vacuum degree of the tower bottom is-0.092 MPa, and internal reflux is adopted, wherein the reflux ratio is 1:1.
The raw materials of the alkylation reaction solution are phenol flow rate 1300L/h; the diisobutylene flow rate is 1500L/h; the catalyst was 430kg of resin catalyst KC102.
The purity of the p-tert-octylphenol obtained was: 99.95%.
Example 3
This example was prepared by the preparation apparatus used in the preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol as described in example 1.
The preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol comprises the following steps:
(1) Introducing the alkylation reaction liquid into a first-stage rectifying tower, extracting light-component phenol from the tower top, extracting o-octyl phenol, p-tert-butyl phenol, p-tert-octyl phenol isomer and 2,4 dioctylphenol from the tower bottom, then introducing the light-component phenol into a second-stage rectifying tower, wherein the temperature of the tower top of the first-stage rectifying tower is 105 ℃, the vacuum degree of the tower top is-0.096 MPa, the temperature of the tower bottom is 183 ℃, the vacuum degree of the tower bottom is-0.085 MPa, and adopting internal reflux and the reflux ratio is 2:1;
(2) Performing reduced pressure distillation in a secondary rectifying tower, extracting mixed components of o-octyl phenol and p-tert-butyl phenol from the tower top, extracting p-tert-octyl phenol from the tower bottom, extracting mixed components of p-tert-octyl phenol isomer and 2,4 dioctyl phenol, feeding tower bottom liquid into a circulating buffer tank, feeding the circulating buffer tank into a crystallizer, and feeding the circulating buffer tank into a tertiary rectifying tower after finishing treatment in the crystallizer, wherein the tower top temperature of the secondary rectifying tower is 128 ℃, the tower top vacuum degree is-0.092 MPa, the tower bottom temperature is 183 ℃, the tower bottom vacuum degree is-0.088 MPa, and adopting internal reflux with a reflux ratio of 2:1;
the initial temperature in the crystallizer is 45 ℃, the heating rate is 4 ℃/min, the end temperature is 81 ℃, and then the temperature is reduced and extracted;
(3) Reduced pressure distillation is carried out in a three-stage rectifying tower, p-tert-octyl phenol is extracted from the tower top, 2, 4-dioctyl phenol is extracted from the tower bottom, the temperature of the tower top of the three-stage rectifying tower is 150 ℃, the vacuum degree of the tower top is-0.096 MPa, the temperature of the tower bottom is 190 ℃, the vacuum degree of the tower bottom is-0.09 MPa, and internal reflux is adopted, wherein the reflux ratio is 1:1.
The raw materials of the alkylation reaction solution are phenol with the flow rate of 1400L/h; the diisobutylene flow rate is 1600L/h; the catalyst was 435kg of resin catalyst KC102.
The purity of the p-tert-octylphenol obtained was: 99.93%.
Example 4
This example was prepared by the preparation apparatus used in the preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol as described in example 1.
The preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol comprises the following steps:
(1) Introducing the alkylation reaction liquid into a first-stage rectifying tower, extracting light-component phenol from the tower top, extracting o-octyl phenol, p-tert-butyl phenol, p-tert-octyl phenol isomer and 2,4 dioctylphenol from the tower bottom, then introducing the light-component phenol into a second-stage rectifying tower, wherein the temperature of the tower top of the first-stage rectifying tower is 95 ℃, the vacuum degree of the tower top is-0.09 MPa, the temperature of the tower bottom is 175 ℃, the vacuum degree of the tower bottom is-0.08 MPa, and adopting internal reflux and the reflux ratio is 1:1;
(2) Performing reduced pressure distillation in a secondary rectifying tower, extracting mixed components of o-octyl phenol and p-tert-butyl phenol from the tower top, extracting mixed components of p-tert-octyl phenol, p-tert-octyl phenol isomer and 2,4 dioctyl phenol from the tower bottom, feeding tower bottom liquid into a circulating buffer tank, feeding the circulating buffer tank into a crystallizer, and feeding the circulating buffer tank into a tertiary rectifying tower after finishing treatment in the crystallizer, wherein the temperature of the tower top of the secondary rectifying tower is 132 ℃, the vacuum degree of the tower top is-0.098 MPa, the vacuum degree of the tower bottom is-0.092 MPa, and the internal reflux is adopted, wherein the reflux ratio is 2:1;
the initial temperature in the crystallizer is 55 ℃, the heating rate is 6 ℃/min, the end temperature is 79 ℃, and then the temperature is reduced and extracted;
(3) Reduced pressure distillation is carried out in a three-stage rectifying tower, p-tert-octyl phenol is extracted from the tower top, 2, 4-dioctyl phenol is extracted from the tower bottom, the temperature of the top of the three-stage rectifying tower is 148 ℃, the vacuum degree of the tower top is-0.097 MPa, the temperature of the tower bottom is 188 ℃, the vacuum degree of the tower bottom is-0.09 MPa, and internal reflux is adopted, wherein the reflux ratio is 1:1.
The raw materials of the alkylation reaction solution are phenol flow rate 1300L/h; the diisobutylene flow rate is 1400L/h; the catalyst was 410kg of resin catalyst KC102.
The purity of the p-tert-octylphenol obtained was: 99.92%.
Comparative example 1
The continuous p-tert-octyl phenol production process comprises the following steps:
(1) Preheating phenol to 90 ℃, and then respectively and continuously introducing the phenol and diisobutylene into a mixer, wherein the phenol flow is 900L/h, and the diisobutylene flow is 1200L/h; the mixed materials enter a first-stage reaction kettle from the bottom of the first-stage reaction kettle to carry out catalytic reaction, the first-stage reaction kettle (with the volume of 15m & lt 3 & gt) is filled with 400kg of resin catalyst KC102, the reaction temperature in the kettle is 90 ℃, the residence time of the materials in the kettle is 30min, the materials are continuously discharged from a discharge hole at the upper part of the first-stage reaction kettle after being subjected to catalytic reaction to a certain liquid level, then enter a second-stage reaction kettle from the bottom of the second-stage reaction kettle to carry out transposition reaction, the second-stage reaction kettle (with the volume of 10m & lt 3 & gt) is filled with 350kg of resin catalyst KC102, the reaction temperature in the kettle is 100 ℃, the residence time of the materials in the kettle is 20min, and the materials are continuously discharged from the upper part of the second-stage reaction kettle after being continuously transposed by the catalyst, so as to obtain p-tert-octyl phenol alkylating liquid;
(2) Introducing the para-tert-octyl phenol alkylation liquid obtained in the step (1) into a first-stage light component removal tower, wherein the temperature of the tower top is 120 ℃, the vacuum degree of the tower top is-0.093 MPa, the temperature of the tower bottom is 185 ℃, the vacuum degree of the tower bottom is-0.090 MPa, and introducing light components such as unreacted diisobutylene, phenol and the like into a first-stage reaction kettle for continuous catalytic reaction by adopting internal reflux with a reflux ratio of 1:2; then the mixture is introduced into a secondary light component removal tower, the temperature of the tower top is 1 ℃ and the vacuum degree of the tower top is-0.93M Pa, the temperature of the tower bottom is 1 ℃ and the vacuum degree of the tower bottom is-0.090 MPa, internal reflux is adopted, the reflux ratio is 1:2, components such as para-tert-butylphenol, ortho-tert-butylphenol and the like which are the middle by-products are removed are introduced into a secondary reaction kettle for continuous transposition reaction, finally the mixture is introduced into a heavy component removal tower, the temperature of the tower top is 1.0 ℃, the vacuum degree of the tower top is-0.096 MPa, the temperature of the tower bottom is 198 ℃, the vacuum degree of the tower top is-0.094 MPa, the external reflux ratio is 2:1, the heavy components are removed, and the para-tert-octylphenol with the purity of 99.2% is obtained from a discharge port at the upper end of the heavy component removal tower.
According to the invention, the crystallizer is introduced, the temperature of the product in the temperature rising box is slowly raised from bottom to top, and the heat conducting oil in the temperature rising coil pipe heats the product from top to bottom, so that the heat conducting oil and the heat conducting oil are opposite to each other, and the heat transfer efficiency and the temperature rising stability are greatly improved. The obtained p-tert-octyl phenol enters a continuous melting crystallizer, impurities such as isomers and the like are extracted step by step, and then rectification is carried out, so that the purity of the product can reach more than 99.9%, and the color change of the p-tert-octyl phenol is improved.
Claims (10)
1. The preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol is characterized by comprising the following steps:
(1) Introducing the alkylation reaction liquid into a first-stage rectifying tower, extracting light-component phenol from the tower top, extracting o-octyl phenol, p-tert-butyl phenol, p-tert-octyl phenol isomer, 2,4 dioctyl phenol from the tower bottom, and then introducing the light-component phenol into a second-stage rectifying tower;
(2) Performing reduced pressure distillation in a secondary rectifying tower, extracting mixed components of o-octyl phenol and p-tert-butyl phenol from the tower top, extracting mixed components of p-tert-octyl phenol, p-tert-octyl phenol isomers and 2,4 dioctyl phenol from the tower bottom, entering a circulating buffer tank, then entering a crystallizer through a circulating pump, and after treatment in the crystallizer is completed, entering a tertiary rectifying tower;
(3) And (3) carrying out reduced pressure distillation in a three-stage rectifying tower, extracting p-tert-octyl phenol from the tower top, and extracting 2,4 dioctyl phenol from the tower bottom.
2. The method for co-producing p-tert-butylphenol by rectification and crystallization of p-tert-octylphenol according to claim 1, wherein in the step (1), the top temperature of the primary rectification column is 95-105 ℃, the top vacuum degree is-0.09-0.096 MPa, the bottom temperature is 175-183 ℃, the bottom vacuum degree is-0.8-0.085 MPa, and the internal reflux and reflux ratio (1-2) are adopted: 1.
3. the method for co-producing p-tert-butylphenol by rectification and crystallization of p-tert-octylphenol according to claim 1, wherein in the step (2), the temperature at the top of the secondary rectifying column is 128-132 ℃, the vacuum degree at the top of the secondary rectifying column is-0.092-0.098 MPa, the temperature at the bottom of the secondary rectifying column is 183-187 ℃, the vacuum degree at the bottom of the secondary rectifying column is-0.088-0.092 MPa, and internal reflux is adopted, and the reflux ratio (2-3): 1.
4. the method for producing p-tert-butylphenol by rectification and crystallization co-production according to claim 1, wherein the crystallizer in the step (2) is a melting crystallizer, the initial temperature in the crystallizer is 45-55 ℃, the heating rate is 4-6 ℃/min, the termination temperature is 79-81 ℃, and then the temperature is reduced and extracted.
5. The method for co-producing p-tert-butylphenol by rectification and crystallization of p-tert-octylphenol according to claim 1, wherein in the step (3), the top temperature of the three-stage rectifying tower is 148-152 ℃, the top vacuum degree is-0.096-0.098 MPa, the bottom temperature is 188-191 ℃, the bottom vacuum degree is-0.090-0.094 MPa, and the internal reflux is adopted, wherein the reflux ratio is 1:1.
6. A preparation device used in a preparation method for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-butylphenol according to any one of claims 1-5 is characterized by comprising a primary rectifying tower (1), wherein the primary rectifying tower (1) is connected with a secondary rectifying tower (2) through a primary rectifying tower discharging pump (16), the secondary rectifying tower (2) is connected with a circulating buffer tank (18) through a mixed component temporary storage tank (7), the circulating buffer tank (18) is connected with a crystallizer (3) through a circulating pump (19), the crystallizer (3) is connected with a tertiary rectifying tower (4) through a tertiary rectifying tower inlet pipeline (20), a p-tert-octylphenol storage tank (8) is connected to the tertiary rectifying tower (4), and a feeding pipeline (5) is connected to the primary rectifying tower (1).
7. The preparation device according to claim 6, wherein the first-stage rectifying tower (1) is connected with a light component storage tank (6), a first-stage rectifying tower discharging pipeline (15) is connected between the first-stage rectifying tower (1) and a first-stage rectifying tower discharging pump (16), a second-stage rectifying tower discharging pipeline (17) is arranged at the bottom of the second-stage rectifying tower (2), and a third-stage rectifying tower bottom discharging pipeline (26) is arranged at the bottom of the third-stage rectifying tower (4).
8. The preparation device according to claim 6, characterized in that a circulating buffer tank feeding pipeline (27) is arranged between the mixed component temporary storage tank (7) and the circulating buffer tank (18), a circulating pump return pipeline (43) is arranged between the circulating pump (19) and the crystallizer (3), a circulating buffer tank feeding pipeline (23) is arranged between the crystallizer (3) and the circulating buffer tank (18), the crystallizer (3) is connected with the heat exchanger (25) through a heat exchange pump (24), the heat exchanger (25) is connected with the crystallizer (3), a light material discharging pipeline (21) is arranged on the crystallizer (3), and a crystallizer feed inlet (28) is arranged on the crystallizer (3).
9. The preparation device according to claim 8, wherein the circulating pump return pipeline (43) is connected with a third-stage rectifying tower inlet pipeline (20) through a tee joint, the third-stage rectifying tower inlet pipeline (20) is connected with the third-stage rectifying tower (4), and a sampler (22) is arranged on the third-stage rectifying tower inlet pipeline (20).
10. The preparation device according to claim 6, wherein the primary rectifying tower (1) is connected with the primary vacuumizing pump (12) through a primary rectifying tower vacuumizing pipeline (9), the secondary rectifying tower (2) is connected with the secondary vacuumizing pump (13) through a secondary rectifying tower vacuumizing pipeline (10), and the tertiary rectifying tower (4) is connected with the tertiary vacuumizing pump (14) through a tertiary rectifying tower vacuumizing pipeline (11).
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| CN202310950458.2A CN116999881A (en) | 2023-07-31 | 2023-07-31 | Preparation method and preparation device for co-producing p-tert-butylphenol by rectifying and crystallizing p-tert-octylphenol |
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