CN1027638C - Method for production of 2,2-di (4-hydroxyl phenyl) propane - Google Patents
Method for production of 2,2-di (4-hydroxyl phenyl) propane Download PDFInfo
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- CN1027638C CN1027638C CN 93101418 CN93101418A CN1027638C CN 1027638 C CN1027638 C CN 1027638C CN 93101418 CN93101418 CN 93101418 CN 93101418 A CN93101418 A CN 93101418A CN 1027638 C CN1027638 C CN 1027638C
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- Prior art keywords
- tower
- acetone
- reaction
- phenol
- dihydroxyphenyl propane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title abstract description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000011347 resin Substances 0.000 claims abstract description 10
- 229920005989 resin Polymers 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 239000000725 suspension Substances 0.000 claims abstract description 8
- 230000000630 rising effect Effects 0.000 claims abstract description 6
- 238000009833 condensation Methods 0.000 claims abstract 2
- 230000005494 condensation Effects 0.000 claims abstract 2
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 239000012071 phase Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 7
- 241000282326 Felis catus Species 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000009834 vaporization Methods 0.000 claims description 4
- 230000008016 vaporization Effects 0.000 claims description 4
- 230000007423 decrease Effects 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000011068 loading method Methods 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 1
- 238000003756 stirring Methods 0.000 abstract description 8
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 5
- 230000009471 action Effects 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000012808 vapor phase Substances 0.000 abstract 1
- 235000013824 polyphenols Nutrition 0.000 description 8
- -1 phenolic ketone Chemical class 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000007599 discharging Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000003245 working effect Effects 0.000 description 2
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a new method of producing bisphenol A from propanone and phenol by condensation under the action of modified cation exchange resin in a suspended reaction knockout tower; inert gas is led into the tower bottom as a rising vapor phase, and plates in the tower are filled with enough resin catalysts for stirring suspension and eliminating water generated in reactions. Phenol and propanone are added respectively from the upper part and side lines of the tower. With the new method, bisphenol A condensed liquid with a concentration of 30% can be obtained, the selectivity of bisphenol A can be as high as 95.5% and the conversion rate of acetone can also reach 95.8%.
Description
The present invention relates to a kind of new manufacturing 2, the method for 2-two (4-hydroxy phenyl) propane (abbreviation dihydroxyphenyl propane).IPCC07C50/00。
Dihydroxyphenyl propane is to produce polycarbonate, Resins, epoxy, and the intermediate of polysulfones and modified phenolic resins particularly requires use colourless when being used to produce polycarbonate, highly purified dihydroxyphenyl propane.
Dihydroxyphenyl propane is under the katalysis of modified cation-exchange resin, is generated by acetone and phenol condensation reaction.Except that dihydroxyphenyl propane, also contain unreacted acetone, unreacted phenol in the reaction product, the water that reaction generates and other by products.The main component of byproduct of reaction is the 2-(2-hydroxy phenyl)-the 2-(4-hydroxy phenyl) propane (is designated hereinafter simply as 2, the 4-isomer) and the dianin (compound of Dianin ' s), also contain 2 in addition, what 4-two [2-(4-hydroxy phenyl) sec.-propyl] phenol (hereinafter to be referred as triphenol), polyphenol and some did not wish to exist can cause painted material.It is that the resin property that raw material is produced reduces that these materials can make with the dihydroxyphenyl propane.
The method of the production dihydroxyphenyl propane in past mainly contains:
1) be Catalyst Production dihydroxyphenyl propane still formula method with hydrochloric acid.This method catalyst levels is little, and speed of response is fast, the acetone conversion height.Shortcoming is that corrodibility is strong, the equipment claimed special substance, and the separation of reaction back hydrochloric acid needs complicated purification apparatus, and easy polluted product.
2) be Catalyst Production dihydroxyphenyl propane still formula method with hydrochloric acid and sulfuric acid.Though this method has been done a little improvement to the salt acid system, do not produce the shortcoming that dihydroxyphenyl propane exists but still fundamentally solve acid system.
3) make Catalyst Production dihydroxyphenyl propane fixed bed process with modified cation-exchange resin.This method is the dihydroxyphenyl propane production method that grows up the late nineteen eighties and be widely adopted, and there is not corrodibility in the ion-exchange resin method, because resin is insoluble to the reaction system, very easily separate after the reaction, and the quality products that is easy to get, but its shortcoming is:
A) speed of response is slow, and the residence time is long, and catalyst levels is big.
B) acetone conversion is low, and production concentration is low, and selectivity is low.
C) phenolic ketone is than high, and the phenol internal circulating load is big, causes the postprocessing working procedures complexity, and load is big.
The objective of the invention is to overcome existing shortcoming of producing the dihydroxyphenyl propane method, and provide a kind of operating process reasonable, consume few, the multistage suspension partition method that productive rate is high, this method is included under the existence of modified ion-exchange resin catalyst, in a multistage suspension reaction tower, produce dihydroxyphenyl propane by acetone and phenol condensation reaction, wherein feeding rare gas element at the bottom of the tower is the main component of rising gas phase, be mixed into phenol and part acetone is the decline liquid phase from cat head, after the vaporization of another part acetone, enter in the tower from certain one or a few column plate at tower middle part, realize the flowing reactive of gas-liquid two-phase adverse current.This reaction process has following characteristics.
A) because the stirring action of rare gas element can make reaction mass fully contact with catalyst surface, reduce diffusional resistance, fast reaction speed, the while is unlikely to shorten the work-ing life of catalyzer again.
B) rare gas element can remove the water that reaction generates, and makes catalyzer keep the high reactivity state, has also accelerated reaction process greatly.
C) adopted the limit to absorb the mode of acetone limit reaction, thus higher local phenolic ketone mol ratio can be guaranteed, thus the reaction preference that can obtain; Because selectivity is good and then can select higher temperature of reaction and lower phenolic ketone mol ratio again for use, thus the concentration of fast reaction speed and dihydroxyphenyl propane further.
D) stirring action of rare gas element and heat-transfer effect help reducing as thermopositive reaction, and the radial and axial temperature difference that produces in reaction prevents from the local superheating of catalyzer and reaction mass to make operation be easier to carry out.
E) every block of column plate all designs a discharging side line, then can be under the condition of not stopping step by step tray catalyst changeout more, promptly adopt the reactor that provides among the present invention can save a standby reactor that is provided with for catalyst changeout more.
F) owing to can obtain higher purpose product bisphenol A concentration, condensated liquid can directly carry out the adducts crystallization operation without lightness-removing column, so can save and take off light thickening equipment, reduced the chance of being heated of reaction mass, can realize real " cold process " operation, help the raising of quality product greatly.
G) overall phenolic ketone has reduced the unreacting phenol internal circulating load than low, helps alleviating follow-up workshop section load.
H) overcome and pack solid catalyst (U.S4471154) with screen cloth and place the catalyzer on the board-like column plate that inconvenience is installed, having overcome short circuit and Bao Nei between the Bao Ji has external diffusion resistance etc. may reduce the shortcoming of catalyst utilization.
I) boiling temperature of phase reaction rectifier unit requirement material and the restriction that the solid-phase catalyst active temperature must mate have been broken away from.Multistage suspension reaction fractionating tower carries light component with rare gas element, and aforementioned two kinds of temperature do not match and can normally move yet, and have widened the range of application of reaction separating device.Accompanying drawing is a technology flow graph of the present invention.Wherein 1 is phenol storage, and 2 is the phenol pump, and 3 is the acetone basin, and 4 is the acetone pump, and 5 is the acetone vaporizer, and 6 is multistage suspension reaction fractionating tower, and 7 is vapour liquid separator, and 8 is cold well, and 9 is moisture eliminator, and 10 is gas compressor, and 11 is gas cylinder, and 12 is discharging pump.
Method operating process of the present invention is: phenol is got to first opening for feed of cat head by phenol pump 2, goes into tower after mixing mutually with the liquid acetone of being made by acetone pump 4 then, and meanwhile the acetone steam after vaporization enters in the tower from upper and lower two opening for feeds of body of the tower.In the tower charging, by gas compressor 10 a certain amount of nitrogen is sent in the tower at the bottom of by tower, so just form vapour-liquid two phase countercurrent flow flow state in the tower, the catalyzer on each plate ceaselessly stirs on the tower inner panel with suspended state under the blowing of steam flow.The stirring action of gas has reduced the external diffusion resistance of catalyst surface.So just formed the reaction process that absorbs while stirring.The nitrogen gas stream that rises can be emitted reaction in the water that generates in the process on the one hand and be taken out of outside the tower, helps keeping activity of such catalysts and accelerated reaction process; It can be taken the part heat that reaction is emitted outside the tower out of on the one hand, plays the effect of certain adjusting tower temperature; The stirring action of air-flow can reduce the radial temperature difference on each plate in the tower on the one hand, does not make its local superheating.Gas stirring also can not produce the high shear force district, thereby can prolong the work-ing life of catalyzer, and the rare gas element (nitrogen) that enters in the tower is discharged from cat head, through vapour liquid separator 7, and cold well 8, moisture eliminator 9 and gas compressor 10 recirculation are got back at the bottom of the tower.Condensation reaction solution is arranged tower by discharging pump 12 and is entered next contrary separation circuit outward.
Among the present invention, the phenolic ketone mol ratio of generally using is 4-12, preferably 5～8.The loadings of resin catalyst is 5～70% of total volume of material of comprising catalyzer on each piece plate.Preferably 10～50%.
Be reflected among the present invention under normal pressure or the pressure-fired and carry out, temperature of reaction is 30～130 ℃, preferably 60～90 ℃.
Among the present invention, be 0.25～2 hour in total residence time of material of dried resin catalyst weight, preferably 0.3～1 hour, the void tower vapour speed of rising vapour phase was 0.006～0.075m/s, preferably 0.025～0.045m/s.
Under the aforementioned processing condition among the present invention, it is 11.4% that condensation reaction products concentration can reach the 30%(prior art), it is 80.5% that the selectivity of purpose product dihydroxyphenyl propane on average can reach the 95.5%(prior art), it is 50.0% that the transformation efficiency of acetone on average can reach the 95.8%(prior art).
The present invention compares with existing processes, not only has the reaction times weak point, and the phenolic ketone mol ratio is low, and catalyst levels is few, and can obtain higher bisphenol A concentration, higher dihydroxyphenyl propane selectivity and higher acetone conversion.
Example
Below specify method of the present invention with example.
By aforementioned technical process, under following processing condition:
80 ℃ of temperature of reaction
Phenolic ketone mol ratio 7: 1
The residence time (in dry catalyst) 0.38h
Phenol flow 5.604Kg/h
Acetone total flux 0.494Kg/h
Followed ring nitrogen flow 2.9m
3/ h
80～90 ℃ of acetone vaporization temperatures
72～74 ℃ of vapor-liquid separation actuator temperatures
Condensation reaction is carried out the operation of about 100 hours continous-stable and is investigated to the multistage suspension tower, and it is analytical results and reaction result in its continuous 12 hours that following table is listed a part of representative data.The average conversion of acetone is 95.8% in the meantime, and the average selectivity of dihydroxyphenyl propane is 95.5%.
Claims (5)
1, a kind of novel method of making dihydroxyphenyl propane, it is characterized in that in the presence of nature-changed cation resin catalyst, in a multistage suspension reaction fractionating tower, produce dihydroxyphenyl propane by acetone and phenol condensation, wherein feeding rare gas element at the bottom of the tower is the rising gas phase, be mixed into phenol and part acetone is the decline liquid phase from cat head, another part acetone vaporization back enters in the tower from certain one or a few column plate of tower middle part, and the reaction process of realization gas-liquid two-phase counter-current flow, wherein the mol ratio of phenol and acetone is 4～12, temperature of reaction is 30～130 ℃, total residence time of material in the dried resin catalyst weight is 0.25～2 hour, and the empty tower gas velocity of rising gas phase is 0.006～0.075m/s.
2, according to the process of claim 1 wherein that the multistage suspension reaction fractionating tower that uses is sieve-tray tower or valve tray column or other form tray columns.
3,, the resin catalyst of q.s is housed on each the piece column plate in the tray column wherein according to the method for claim 2.
4, according to the process of claim 1 wherein that the loadings of resin catalyst is to comprise that total volume of material of catalyzer is 5～70% on each piece plate.
5, according to the process of claim 1 wherein that the rare gas element as the rising gas phase can be a nitrogen.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93101418 CN1027638C (en) | 1993-02-17 | 1993-02-17 | Method for production of 2,2-di (4-hydroxyl phenyl) propane |
| KR1019950703371A KR100216163B1 (en) | 1993-02-17 | 1994-02-16 | A multiple stage suspended reactive stripping process and apparatus |
| AU61056/94A AU6105694A (en) | 1993-02-17 | 1994-02-16 | A multiple stage suspended reactive stripping process and apparatus |
| RU95121590A RU2126706C1 (en) | 1993-02-17 | 1994-02-16 | Multistage method of suspension reaction steaming and device for its embodiment |
| US08/505,311 US5679312A (en) | 1993-02-17 | 1994-02-16 | Multiple stage suspended reactive stripping process and apparatus |
| JP51852294A JP3437575B2 (en) | 1993-02-17 | 1994-02-16 | Multi-stage suspension reaction stripping method and apparatus |
| BR9406248A BR9406248A (en) | 1993-02-17 | 1994-02-16 | Multistage suspended reactive distillation process and apparatus |
| EP94907484A EP0693957B1 (en) | 1993-02-17 | 1994-02-16 | A multiple stage suspended reactive stripping process and apparatus |
| DE69408130T DE69408130T2 (en) | 1993-02-17 | 1994-02-16 | MULTI-STAGE, SUSPENDED, REACTIVE STRIPING AND DEVICE THEREFOR |
| CA002155969A CA2155969C (en) | 1993-02-17 | 1994-02-16 | A multiple stage suspended reactive stripping process and apparatus |
| PCT/CN1994/000012 WO1994019079A1 (en) | 1993-02-17 | 1994-02-16 | A multiple stage suspended reactive stripping process and apparatus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93101418 CN1027638C (en) | 1993-02-17 | 1993-02-17 | Method for production of 2,2-di (4-hydroxyl phenyl) propane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1077187A CN1077187A (en) | 1993-10-13 |
| CN1027638C true CN1027638C (en) | 1995-02-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 93101418 Expired - Fee Related CN1027638C (en) | 1993-02-17 | 1993-02-17 | Method for production of 2,2-di (4-hydroxyl phenyl) propane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1027638C (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005030687A1 (en) | 2003-09-28 | 2005-04-07 | China Petroleum & Chemical Corporation | Method for preparing bisphenol a |
| WO2007058234A1 (en) * | 2005-11-21 | 2007-05-24 | Mitsubishi Chemical Corporation | Process for producing bisphenol a and vertical fixed-bed reactor |
| CN102580631A (en) * | 2012-03-01 | 2012-07-18 | 王健祥 | Double-circular plate tower |
| KR20170031137A (en) * | 2014-07-15 | 2017-03-20 | 사빅 글로벌 테크놀러지스 비.브이. | Synthesis of bisphenols |
| CH712479A1 (en) * | 2016-05-20 | 2017-11-30 | Flumroc Ag | Plant and method of making an airgel composite and airgel composite. |
-
1993
- 1993-02-17 CN CN 93101418 patent/CN1027638C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1077187A (en) | 1993-10-13 |
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