CN116514643B - Production method and production system of beta-isophorone - Google Patents
Production method and production system of beta-isophorone Download PDFInfo
- Publication number
- CN116514643B CN116514643B CN202310500596.0A CN202310500596A CN116514643B CN 116514643 B CN116514643 B CN 116514643B CN 202310500596 A CN202310500596 A CN 202310500596A CN 116514643 B CN116514643 B CN 116514643B
- Authority
- CN
- China
- Prior art keywords
- isophorone
- inlet
- gas
- beta
- outlet
- 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.)
- Active
Links
- LKOKKQDYMZUSCG-UHFFFAOYSA-N 3,5,5-Trimethyl-3-cyclohexen-1-one Chemical compound CC1=CC(C)(C)CC(=O)C1 LKOKKQDYMZUSCG-UHFFFAOYSA-N 0.000 title claims abstract description 228
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 82
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims abstract description 106
- 239000003054 catalyst Substances 0.000 claims abstract description 97
- 239000007788 liquid Substances 0.000 claims abstract description 68
- 239000000463 material Substances 0.000 claims abstract description 28
- 238000010438 heat treatment Methods 0.000 claims abstract description 21
- 238000000926 separation method Methods 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 12
- 230000008016 vaporization Effects 0.000 claims abstract description 11
- 239000007858 starting material Substances 0.000 claims abstract description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 47
- 238000011049 filling Methods 0.000 claims description 16
- 239000002808 molecular sieve Substances 0.000 claims description 13
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 13
- 239000002994 raw material Substances 0.000 claims description 11
- 229910021536 Zeolite Inorganic materials 0.000 claims description 10
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 10
- 230000001105 regulatory effect Effects 0.000 claims description 10
- 239000010457 zeolite Substances 0.000 claims description 10
- 239000011344 liquid material Substances 0.000 claims description 8
- GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical compound [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 claims description 8
- 238000012546 transfer Methods 0.000 claims description 8
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 claims description 7
- 238000011068 loading method Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 238000009738 saturating Methods 0.000 claims description 2
- 238000003746 solid phase reaction Methods 0.000 abstract description 8
- 239000007791 liquid phase Substances 0.000 abstract description 7
- 238000007086 side reaction Methods 0.000 abstract description 6
- 238000009825 accumulation Methods 0.000 abstract description 3
- 230000000977 initiatory effect Effects 0.000 abstract description 2
- 235000021190 leftovers Nutrition 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000007789 gas Substances 0.000 description 18
- 238000006317 isomerization reaction Methods 0.000 description 18
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 13
- 229910052700 potassium Inorganic materials 0.000 description 13
- 239000011591 potassium Substances 0.000 description 13
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 13
- 239000012295 chemical reaction liquid Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 6
- 238000004891 communication Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- -1 p-toluenesulfonate anions Chemical class 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 229910010293 ceramic material Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
-
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/603—Unsaturated compounds containing a keto groups being part of a ring of a six-membered ring, e.g. quinone methides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a production method and a production system of beta-isophorone, which take alpha-isophorone as a starting material to prepare beta-isophorone, wherein the adopted production system comprises a heater for heating and vaporizing the alpha-isophorone, a gas-liquid separator, a packed column filled with a catalyst and a rectifying tower which are sequentially arranged, the production method comprises the steps of heating and vaporizing the alpha-isophorone by the heater, then entering the gas-liquid separator to perform gas-liquid separation to obtain a gas material, and entering the packed column to be catalyzed by the catalyst and then entering the rectifying tower to perform separation to obtain the beta-isophorone. The method converts the liquid-solid phase reaction into the gas-solid phase reaction, greatly reduces the loss of the catalyst, avoids the accumulation of the catalyst in the liquid phase and the initiation of side reaction, and also greatly avoids the instability of the product caused by the catalyst entering the product.
Description
Technical Field
The invention relates to the technical field of fine chemical engineering, in particular to a production method and a production system of beta-isophorone.
Background
Beta-isophorone is an important chemical intermediate and is widely used for preparing carotenoid, vitamin E and perfume. The prior art beta-isophorone is prepared from alpha-isophorone by a thermal isomerization reaction. Since α -isophorone has conjugated carbon-carbon double bonds and carbon-oxygen double bonds, thermodynamic equilibrium tends to be more toward α -isophorone. To prepare the beta-isophorone, only a small amount of beta-isophorone in a thermal isomerism balance system can be separated through high-efficiency rectification, so that balance is promoted to move towards the direction of forming the beta-isophorone, and the beta-isophorone meeting the quality requirement is finally obtained while the beta-isophorone is separated during thermal isomerism. This has the problems of high temperature, low yield, long time and high energy consumption for preparing the beta-isophorone.
Chinese patent CN1259299C discloses a synthesis method of beta-isophorone, which takes alpha-isophorone as a raw material, and under the condition that a catalyst and a separating agent for reaction are acid ceramic materials, isomerization reaction is carried out in a multi-stage reactor, and reaction rectification technology is adopted for reaction, so that beta-isophorone is obtained. In the method, the separation section is also made of an acidic ceramic material, so that the beta-isophorone is promoted to be formed into alpha-isophorone, the production efficiency is low, and meanwhile, the acidic ceramic material is filled in the reactor and is easy to flow out to enter the tower kettle of the rectifying tower to cause side reaction.
Chinese patent CN104649878B discloses a process for continuously synthesizing β -isophorone, which uses α -isophorone as a starting material, uses molecular sieve as a catalyst, adopts a reactive distillation technique to perform isomerization reaction in a reactor at a tower bottom, and collects β -isophorone at the top of the reactor at the tower bottom. The method has low yield, and the catalyst is in long-term contact with the reaction liquid, so that side reactions are easy to cause.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a production method of beta-isophorone with few byproducts and high yield.
The second object of the present invention is to provide a production system of beta-isophorone with few byproducts and high yield.
In order to achieve the purpose, the invention adopts the following technical scheme:
The production method of the beta-isophorone comprises the steps of taking alpha-isophorone as a starting material, carrying out isomerization reaction in a production system under the action of a catalyst to generate the beta-isophorone, wherein the production system comprises a heater, a gas-liquid separator, a packed column and a rectifying tower which are sequentially arranged and used for heating and vaporizing the alpha-isophorone;
The catalyst is filled in the packed column;
the production method comprises the steps of heating and vaporizing alpha-isophorone through the heater, then enabling the alpha-isophorone to enter the gas-liquid separator for gas-liquid separation to obtain a gas material, enabling the gas material to enter the packed column, catalyzing the gas material through the catalyst, and then enabling the gas material to enter the rectifying tower for separation to obtain beta-isophorone.
The catalyst is filled in the filling column, the filling column and the rectifying tower are arranged independently, the reaction starting material is heated and gasified to obtain a gas material, and the gas material is catalyzed and then enters the rectifying tower to be separated to obtain the beta-isophorone. According to the method, in the first aspect, the liquid-solid phase reaction for thermally isomerizing the alpha-isophorone to the beta-isophorone is converted into the gas-solid phase catalytic reaction, so that the scouring of liquid to the catalyst is avoided, the loss of the catalyst is reduced, the accumulation of the catalyst in the liquid phase is avoided, and the side reaction is avoided, in the second aspect, heavy components in the reaction liquid can directly flow into the tower kettle of the rectifying tower from the liquid phase outlet of the gas-liquid separator, the content of the heavy components in the gas material obtained by separation of the gas-liquid separator is extremely low, the heavy components cannot be adsorbed on a carrier of the catalyst and cover the surface of the active components to cause deactivation, the service life of the catalyst can be prolonged, and in the third aspect, the byproducts possibly formed by promoting the self polymerization of the alpha-isophorone or the beta-isophorone due to the loss of the catalyst entering the reaction liquid are reduced. The catalyst can only accelerate the thermal isomerization of alpha-isophorone to beta-isophorone and reach the speed of equilibrium composition, but does not influence the equilibrium composition. If the catalyst is lost to the rectifying tower or is further carried into the beta-isophorone product, the catalyst can catalyze the conversion of beta-isophorone to alpha-isophorone after the temperature is reduced, and the quality of the final product is affected. The gas-solid phase reaction mode can well solve the problem and improve the stability of the final product.
In some embodiments, the production method further comprises feeding the liquid material separated by the gas-liquid separator into a bottom of the rectifying tower.
According to some embodiments of the invention, the production method further comprises feeding the starting raw material into a tower kettle of the rectifying tower for heating, and then conveying materials in the tower kettle of the rectifying tower to the heater for heating and gasifying;
or/and, the production method further comprises the step of directly conveying the starting raw materials to the heater for heating and gasifying.
According to some embodiments of the invention, the catalyst is a supported p-toluenesulfonate catalyst.
The supported p-toluenesulfonate catalyst is used as a catalyst for preparing beta-isophorone through thermal isomerization reaction. The p-toluenesulfonate anions have strong nucleophilicity, and can rapidly attack 1 # carbonium positive ions of alpha-isophorone to promote electron rearrangement. P-toluenesulfonate is also a strong leaving group, readily leaving from 1 # carbonium ion to form β -isophorone. So that the p-toluenesulfonate is used as a catalyst for thermally isomerizing alpha-isophorone to beta-isophorone, and the thermal isomerization reaction can be quickly promoted to reach equilibrium. The ratio of alpha-isophorone and beta-isophorone in the equilibrium state is directly related to the temperature of the thermal isomerization reaction, and the higher the temperature of the thermal isomerization reaction is, the larger the ratio of beta-isophorone is, and the lower the temperature of the thermal isomerization reaction is, the smaller the ratio of beta-isophorone is. Compared with the prior art, the application adopts the supported p-toluenesulfonate catalyst to accelerate the speed of thermal isomerization reaction, so that the alpha-isophorone and beta-isophorone can reach balance rapidly.
When the technical scheme of the application is implemented, the aim of improving the conversion efficiency can also be achieved by directly mixing the p-toluenesulfonate with the raw material alpha-isophorone. The application adopts the supported p-toluenesulfonate as the catalyst, and can conveniently separate the p-toluenesulfonate from the final reaction liquid. On the one hand, the catalyst can be recycled, the cost and the solid waste amount of the catalyst prepared repeatedly are reduced, and on the other hand, the adverse effect on the stability of beta-isophorone or alpha-isophorone under the high temperature of strong acid and strong alkali salt is reduced. Preferably, the carrier of the supported p-toluenesulfonate catalyst is one or a combination of a plurality of zeolite and molecular sieve. The zeolite or molecular sieve is used as carrier and has the advantages of large particle size, strong adsorption capacity and convenient separation. The prior art also reports that solid acid can be used as a catalyst for isomerization reaction, but has the problems of more byproduct generation and serious corrosion. The zeolite and the molecular sieve have weak acidity and can catalyze the isomerization reaction of the application, but have the problems of weak catalysis effect and low production efficiency. According to the application, the p-toluenesulfonate is loaded on the molecular sieve or zeolite, and the p-toluenesulfonate microcrystals are uniformly dispersed on the surface of the molecular sieve or zeolite and in the micro-channels, so that the contact point of the p-toluenesulfonate and the alpha-isophorone is improved. The molecular sieve or zeolite provides an acidic activation center, and the p-toluenesulfonate provides a nucleophilic group, so that the aim of synergistic catalytic isomerization reaction is fulfilled.
The p-toluenesulfonate is an alkali metal salt or alkaline earth metal salt of p-toluenesulfonate, preferably, the p-toluenesulfonate is one or a combination of more of sodium p-toluenesulfonate and potassium p-toluenesulfonate. Sodium p-toluenesulfonate and potassium p-toluenesulfonate belong to strong alkali strong acid salts, and aqueous solutions at room temperature are neutral. As a catalyst for thermal isomerization reaction, the adverse effects of strong acidity and strong alkalinity on the stability of alpha-isophorone or beta-isophorone can be reduced to the maximum extent.
Preferably, the loading of the p-toluenesulfonate in the supported p-toluenesulfonate catalyst is 0.1-1.0wt%. The more the p-toluenesulfonate is loaded, the more the p-toluenesulfonate adsorbed in the inner pore canal of the carrier is, the less the p-toluenesulfonate is easy to fall off, the longer the service life of the catalyst is, but the catalytic activity is reduced, on the contrary, the more the p-toluenesulfonate is loaded, the more the p-toluenesulfonate adsorbed on the surface of the carrier is easy to fall off, the shorter the service life of the catalyst is, but the catalytic activity of the initial catalyst is strong. In practical applications, it is necessary to avoid the loss of the p-toluenesulfonate adsorbed on the carrier to the reaction liquid as much as possible, otherwise the reaction liquid is in contact with the p-toluenesulfonate in a free state for a long time to easily form polymerization byproducts. The loading of the p-toluenesulfonate in the catalyst is controlled to be 0.1-1.0wt%, so that the loss of active ingredients can be reduced on the premise of keeping the catalyst to have optimal catalytic activity.
The preparation method of the catalyst has great influence on the catalytic activity of the catalyst, and the inventor determines the optimal preparation method of the catalyst through a large number of comparison experiments, and preferably, the supported p-toluenesulfonate catalyst is prepared by immersing a carrier in a p-toluenesulfonate aqueous solution, adsorbing and saturating, filtering and drying.
Further preferably, the drying is performed at 100-140 ℃. The preparation method of the catalyst is simple and convenient, raw materials are easy to obtain, but the catalyst has strong catalytic activity, and the catalyst can be replaced in time when the activity of the catalyst is insufficient.
In order to further improve the technical effect, preferably, the theoretical plate number of the rectifying tower is 30-60. The design of the rectifying tower is critical, and the chemical reaction and the rectifying separation are combined by reactive rectification. To design a production system with excellent performance, it is first necessary to determine whether the control process of the whole production system belongs to reaction control or rectification control. When the method belongs to the reaction control, the adjustment of the catalyst and the reaction parameters can rapidly influence the performance of the whole production system, and when the method belongs to the rectification control, the adjustment of the catalyst and the reaction parameters can not rapidly influence the performance of the whole production system. In view of the fact that the high-efficiency supported p-toluenesulfonate is used as a catalyst for thermal isomerization reaction, when the theoretical plate number of the rectifying tower is 30-60, a production system can be artificially designed into a reaction control state.
In some embodiments, the reflux ratio of the top of the rectifying tower is controlled to be 4-8:1.
Preferably, the temperature of the tower bottom of the rectifying tower is controlled to be 200-250 ℃, the pressure in the rectifying tower is controlled to be 0.05-0.15 MPaA (absolute pressure), and more preferably, the temperature of the tower bottom of the rectifying tower is controlled to be the reflux temperature of reaction materials, specifically 220-230 ℃, and the pressure in the rectifying tower is controlled to be normal pressure. And heating the reaction liquid in the tower kettle of the rectifying tower to a reflux temperature of about 220-230 ℃, wherein the equilibrium concentration of beta-isophorone in the reaction liquid is about 2.5-3.5wt%. The catalyst can accelerate the time for reaching the equilibrium state and reduce the formation of byproducts at high temperature. And separating the beta-isophorone from the reaction liquid by rapid rectification, and collecting to obtain the beta-isophorone, wherein the p-toluenesulfonate is loaded on a carrier and does not enter the tower bottom of the rectifying tower. The vaporization amount in the reactive rectifying tower is controlled, and the p-toluenesulfonate and other active substances are further ensured not to enter the beta-isophorone finished product, so that the beta-isophorone finished product with stable quality is prepared.
According to some embodiments of the invention, the heater has an inlet and an outlet, the gas-liquid separator has an inlet, a gas outlet and a liquid outlet, the inlet of the gas-liquid separator is in communication with the outlet line of the heater, the packed column has an inlet and an outlet, the inlet of the packed column is in communication with the gas outlet line of the gas-liquid separator, the column bottom of the rectifying column has a first inlet, a second inlet and an outlet, the second inlet of the column bottom is disposed higher than the first inlet of the column bottom, the outlet of the column bottom is in communication with the inlet of the heater through a first connecting tube, the first inlet of the column bottom is in communication with the liquid outlet of the gas-liquid separator through a second connecting tube, and the second inlet of the column bottom is in communication with the outlet of the packed column through a third connecting tube.
In some embodiments, a first transfer pump is provided on the first connection tube.
In order to make the whole production system operate more stably, the balance of flow and pressure is needed. Preferably, the second connecting pipe is provided with a second delivery pump and a regulating valve, and the regulating valve is positioned at the downstream of the second delivery pump. When the gas-liquid separator has enough height difference relative to the rectifying tower kettle, the second conveying pump is not required, and the liquid phase can automatically enter the rectifying tower kettle through the liquid level difference. However, the provision of the second transfer pump can improve the stability of the overall system. The liquid level signal of the gas-liquid separator is transmitted to an automatic control system to finally control the opening degree of a regulating valve to control the liquid level in the gas-liquid separator at a proper position, so that the quantity of liquid phases in the gas-liquid separator is reduced as much as possible under the premise of ensuring the stable liquid phase discharging.
In some embodiments, the production system further comprises a feed tube connected to the first connecting tube.
According to some embodiments of the invention, the production system further comprises a condenser having an inlet and an outlet, the inlet of the condenser being connected to the top of the rectifying column via a fourth connecting pipe, the outlet of the condenser being connected to the top of the rectifying column via a fifth connecting pipe, and a β -isophorone receiving tank being connected to the fifth connecting pipe via a sixth connecting pipe.
In some embodiments, the heater is a reboiler.
The second technical scheme adopted by the invention is that the production system for producing beta-isophorone comprises a heater for heating and vaporizing alpha-isophorone, a gas-liquid separator, a filling column filled with a catalyst and a rectifying tower, wherein the heater is provided with an inlet and an outlet, the gas-liquid separator is provided with an inlet, a gas outlet and a liquid outlet, the inlet of the gas-liquid separator is communicated with an outlet pipeline of the heater, the filling column is provided with an inlet and an outlet, the inlet of the filling column is communicated with a gas outlet pipeline of the gas-liquid separator, a tower kettle of the rectifying tower is provided with a first inlet, a second inlet and an outlet, the second inlet of the tower kettle is higher than the first inlet of the tower kettle, the outlet of the tower kettle is communicated with the inlet of the heater through a first connecting pipe, the first inlet of the tower kettle is communicated with the liquid outlet of the gas-liquid separator through a second connecting pipe, and the second inlet of the tower kettle is communicated with the outlet of the filling column through a third connecting pipe;
the alpha-isophorone is gasified by heating by the heater and then enters the gas-liquid separator to carry out gas-liquid separation, so as to obtain a gas material and a liquid material;
the gas material is introduced into the filling column, catalyzed by the catalyst and then enters the rectifying tower for separation, and the beta-isophorone is obtained;
And the liquid material is introduced into the tower kettle of the rectifying tower, and the material in the tower kettle of the rectifying tower enters the heater again or is discharged.
Preferably, the second inlet of the tower kettle is higher than the first inlet of the tower kettle, and the first inlet of the tower kettle is higher than the outlet of the tower kettle.
In some embodiments, the first connecting pipe is provided with a first delivery pump, and the second connecting pipe is provided with a second delivery pump.
In some embodiments, the production system further comprises a feed tube connected to the first connecting tube.
In some embodiments, the theoretical plate number of the rectifying tower is 30-60.
In some embodiments, the production system further comprises a condenser having an inlet and an outlet, the inlet of the condenser being connected to the top of the rectifying column by a fourth connecting pipe, the outlet of the condenser being connected to the top of the rectifying column by a fifth connecting pipe, and a β -isophorone receiving tank being connected to the fifth connecting pipe by a sixth connecting pipe.
In some embodiments, the catalyst is a supported p-toluenesulfonate catalyst.
In some embodiments, the carrier of the catalyst is one or more of zeolite and molecular sieve, and/or the p-toluenesulfonate is one or more of sodium p-toluenesulfonate and potassium p-toluenesulfonate, and/or the loading of the p-toluenesulfonate in the supported p-toluenesulfonate catalyst is 0.1-1.0wt%.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
The production method of the invention firstly heats and gasifies the reaction initial raw material, and the gas material enters the rectifying tower to be separated to obtain the beta-isophorone after catalysis, on one hand, the liquid-solid phase reaction is converted into the gas-solid phase reaction, thereby greatly reducing the loss of active components in the catalyst, avoiding the accumulation of the catalyst in the liquid phase and the initiation of side reaction, and also greatly avoiding the instability of the product caused by the catalyst entering the product, on the other hand, the raw material is catalyzed by the catalyst and then separated in the rectifying tower, thereby greatly reducing the occurrence of reverse isomerization reaction in the separating section and improving the production efficiency.
The beta-isophorone obtained by the production method has the content of more than 99 weight percent, the yield of more than 95 percent and the tower still residue rate of the rectifying tower of less than 4 weight percent.
Drawings
FIG. 1 is a schematic diagram showing the structure of a production system for preparing beta-isophorone according to an embodiment of the present invention;
the device comprises a heater, a gas-liquid separator, a packed column, a rectifying tower, a condenser, a 6, beta-isophorone receiving tank, a first conveying pump, a second conveying pump, a first connecting pipe, a second connecting pipe, a third connecting pipe, a fourth connecting pipe, a fifth connecting pipe, a sixth connecting pipe, a fourth connecting pipe, a fifth connecting pipe, a sixth connecting pipe, a 15, a feeding pipe, a fourth connecting pipe and a regulating valve, wherein the first connecting pipe, the second connecting pipe, the third connecting pipe, the fourth connecting pipe, the fifth connecting pipe, the sixth connecting pipe, the fourth connecting pipe, the fifth connecting pipe, the fourth connecting pipe and the regulating valve.
Detailed Description
According to the application, the liquid-solid phase reaction is converted into the gas-solid phase reaction, and the filling column filled with the catalyst and the rectifying tower are arranged independently, so that the possibility that the catalyst enters the rectifying tower kettle is greatly reduced. The catalyst enters the tower kettle of the rectifying tower to enable the alpha-isophorone or beta-isophorone to contact the catalyst at high temperature for a long time, so that polymerization side reaction is easily initiated to form a high molecular byproduct. The catalyst entering the bottom of the rectifying tower can be also brought into the packing layer when the rectifying tower is abnormally operated and is flooded, and further can enter the beta-isophorone product. When a trace amount of catalyst exists in the beta-isophorone, the beta-isophorone can be slowly converted into alpha-isophorone, and the stability of the product is reduced.
One preferred and specific embodiment is as follows:
Taking alpha-isophorone as a starting material, and carrying out isomerization reaction in a production system under the action of a catalyst to generate beta-isophorone, wherein the production system comprises a heater, a gas-liquid separator, a packed column and a rectifying tower which are sequentially arranged and used for heating and vaporizing the alpha-isophorone;
The catalyst is filled in the packed column;
The production method comprises the steps of adding an initial raw material into a rectifying tower for heating, conveying the raw material to a heater for heating and vaporizing, and then enabling the raw material to enter a gas-liquid separator for gas-liquid separation to obtain a liquid material and a gas material;
the liquid material is conveyed to a tower kettle of a rectifying tower;
And the gas material enters the filling column, is catalyzed by the catalyst, enters the rectifying column for separation, and after the material at the top of the rectifying column is condensed by the condenser, one part of the material flows back to the rectifying column, and the other part of material is output to the beta-isophorone receiving tank to obtain a beta-isophorone finished product.
In a further preferred scheme, the catalyst is a supported p-toluenesulfonate catalyst, so that the possibility that the p-toluenesulfonate enters the tower kettle of the rectifying tower is reduced.
As shown in fig. 1, the production method of the present invention can be implemented in the production system shown in the figure.
The production system for producing beta-isophorone as shown in fig. 1 comprises a heater 1 for heating up and gasifying alpha-isophorone, a gas-liquid separator 2, a packed column 3 filled with a catalyst inside, a rectifying column 4, a condenser 5, and a beta-isophorone receiving tank 6.
The heater 1 is provided with an inlet and an outlet, the gas-liquid separator 2 is provided with an inlet, a gas outlet and a liquid outlet, the inlet of the gas-liquid separator 2 is communicated with an outlet pipeline of the heater 1, the packed column 3 is provided with an inlet and an outlet, the inlet of the packed column 3 is communicated with a gas outlet pipeline of the gas-liquid separator 2, the tower kettle of the rectifying tower 4 is provided with a first inlet, a second inlet and an outlet, the outlet of the tower kettle of the rectifying tower 4 is communicated with the inlet of the heater 1 through a first connecting pipe 9, the first inlet of the tower kettle of the rectifying tower 4 is communicated with the liquid outlet of the gas-liquid separator 2 through a second connecting pipe 10, and the second inlet of the tower kettle of the rectifying tower 4 is communicated with the outlet of the packed column 3 through a third connecting pipe 11.
The second inlet of the rectifying tower 4 tower kettle, the first inlet of the rectifying tower 4 tower kettle and the outlet of the rectifying tower 4 tower kettle are sequentially distributed from top to bottom in the vertical direction.
The first connecting pipe 9 is provided with a first delivery pump 7, the second connecting pipe 10 is provided with a second delivery pump 8 and a regulating valve 16 respectively, and the regulating valve 16 is arranged closer to the rectifying tower 4 than the second delivery pump 8.
The condenser 5 has an inlet and an outlet, the inlet of the condenser 5 is connected to the top of the rectifying column 4 through a fourth connecting pipe 12, the outlet of the condenser 5 is connected to the top of the rectifying column 4 through a fifth connecting pipe 13, and the beta-isophorone receiving tank 6 is connected to the fifth connecting pipe 13 through a sixth connecting pipe 14.
The production system further comprises a feed pipe 15, which feed pipe 15 is connected to the first connecting pipe 9.
In this example, the heater 1 is a reboiler, and is heated by heat conducting oil, and the heating temperature is 200-250 ℃.
In some embodiments, the parameters of rectifying column 4 are such that the column diameter is 0.6m, the internal packing is BX stainless steel wire mesh, and the packing layer height is 8m.
The following detailed description of the present invention is provided in connection with specific embodiments so that those skilled in the art may better understand and practice the present invention, but is not intended to limit the scope of the present invention.
Example 1
This example employs the production system shown in fig. 1 to produce β -isophorone, comprising:
(1) Preparation of the catalyst
Adding 0.05kg of potassium paratoluenesulfonate and 25kg of deionized water into a reaction kettle, stirring, controlling the temperature in the reaction kettle to be 25-35 ℃ for dissolution, and adding 5kg of potassium paratoluenesulfonate into the reaction kettle after dissolution is completedAfter molecular sieve adsorption for 30min, stirring is stopped and the mixture is allowed to stand overnight.
The next day, filtering, directly transferring the filter cake into a baking pan without washing, putting the baking pan into a baking oven, drying for 2 hours at 30-40 ℃, then raising the temperature of the baking oven to 120 ℃, and continuously drying for 4 hours to obtain about 5.03kg of supported potassium paratoluenesulfonate catalyst, wherein the load of the potassium paratoluenesulfonate catalyst is about 0.60wt%. The dried catalyst was all packed in the catalyst packed column 3.
(2) Preparation of beta-isophorone
The theoretical plate number of the rectifying tower 4 is 48, 1200kg of alpha-isophorone (the content of the alpha-isophorone is 99.4 wt%) is added into the tower kettle of the rectifying tower 4, the pressure in the rectifying tower 4 is controlled to be normal pressure, a first conveying pump 7 is started, a heat conducting oil inlet valve of a reboiler is started to heat materials, the heating temperature is 220-230 ℃, a second conveying pump 8 is started, the opening degree of a regulating valve 16 is automatically controlled through the liquid level of the gas-liquid separator 2, and the liquid level in the gas-liquid separator 2 is kept to be close to the constant minimum liquid level.
The steam separated by the gas-liquid separator 2 enters the packed column 3, is thermally isomerized by the catalyst, and then enters the rectifying tower 4, the reflux ratio of the top of the rectifying tower 4 is controlled to be 6:1, and the recovery flow of beta-isophorone is controlled to be 51kg/h.
Finally, 1169kg of beta-isophorone (beta-isophorone content: 99.3wt%, alpha-isophorone content: 0.21 wt%) was obtained, and the yield was 97.3%. 27kg of leftovers and 2.25wt% of leftovers.
Example 2
The production system and the production method adopted in this embodiment are basically the same as those in embodiment 1, except that:
in the step (1), 0.08kg of potassium paratoluenesulfonate is added into the reaction kettle to obtain about 5.05kg of supported potassium paratoluenesulfonate catalyst, wherein the supported potassium paratoluenesulfonate is about 1.0wt%.
In the step (2), the recovery flow rate of beta-isophorone at the top of the rectifying tower 4 is 77kg/h.
1148Kg of beta-isophorone (beta-isophorone content: 99.2% by weight, alpha-isophorone content: 0.25% by weight) was finally obtained, and the yield was 95.5%. 46kg of leftovers and 3.8wt% of leftovers.
Example 3
The production system and the production method adopted in this embodiment are basically the same as those in embodiment 1, except that:
In the step (1), 0.008kg of potassium paratoluenesulfonate is put into the reaction kettle to obtain about 5.005kg of supported potassium paratoluenesulfonate catalyst, and the potassium paratoluenesulfonate load is about 0.1wt%.
In the step (2), the recovery flow rate of beta-isophorone at the top of the rectifying tower 4 is 24kg/h.
Finally 1174kg of beta-isophorone (beta-isophorone content: 99.4wt%, alpha-isophorone content: 0.22 wt%) were obtained, and the yield was 97.8%. 21kg of leftovers and 1.75wt% of leftovers.
Example 4
The production system and the production method adopted in this embodiment are basically the same as those in embodiment 1, except that:
In the step (2), 1200kg of alpha-isophorone (alpha-isophorone content: 99.4 wt%) was charged into the bottom of the rectifying column 4, 1200kg of alpha-isophorone (alpha-isophorone content: 99.4 wt%) was added into the production system through the feed pipe 15, and the feed flow rate in the feed pipe 15 was controlled to be 50kg/h. The recovery flow rate of beta-isophorone at the top of the rectifying tower 4 is 48kg/h.
Finally, 2342kg of beta-isophorone (beta-isophorone content: 99.5% by weight, alpha-isophorone content: 0.18% by weight) was obtained, and the yield was 97.7%. 50kg of leftovers and 2.1wt% of leftovers.
Example 5
The production system and the production method adopted in this embodiment are basically the same as those in embodiment 1, except that:
In the step (2), the reflux ratio of the top of the rectifying tower 4 is controlled to be 4:1, and the recovery flow of beta-isophorone is 82kg/h.
1172Kg of beta-isophorone (beta-isophorone content: 99.0% by weight, alpha-isophorone content: 0.42% by weight) were finally obtained, and the yield was 97.3%. 24kg of leftovers and 2.0wt% of leftovers.
Example 6
The production system and the production method adopted in this embodiment are basically the same as those in embodiment 1, except that:
in the step (1), sodium p-toluenesulfonate is adopted to replace potassium p-toluenesulfonate, and zeolite is adopted to replace Molecular sieve, about 5.03kg of supported sodium p-toluenesulfonate catalyst was obtained, with a loading of about 0.59wt%.
In the step (2), the recovery flow rate of the beta-isophorone is 49kg/h.
1167Kg of beta-isophorone (beta-isophorone content: 99.2wt%, alpha-isophorone content: 0.33 wt%) was finally obtained, and the yield was 97.1%. 29kg of leftovers and 2.4wt% of leftovers.
Comparative example 1
The production system and the production method adopted in this comparative example are basically the same as those of example 1, except that 0.03kg of potassium p-toluenesulfonate as a catalyst was directly added to the column bottom of the rectifying column 4 without turning on the first transfer pump.
The recovery flow of beta-isophorone at the top of the rectifying tower 4 is 62kg/h.
Finally, 1122kg of beta-isophorone (beta-isophorone content: 98.9% by weight, alpha-isophorone content: 0.28% by weight) was obtained, and the yield was 93.0%. 73kg of leftovers and 6.1wt% of leftovers.
Comparative example 2
The production system and production method adopted in this comparative example are basically the same as those in example 1, except that:
In the step (1), 0.15kg of potassium paratoluenesulfonate is added into the reaction kettle to obtain about 5.11kg of supported potassium paratoluenesulfonate catalyst, wherein the supported potassium paratoluenesulfonate is about 2.15wt%.
In the step (2), the beta-isophorone extraction flow rate at the top of the rectifying tower 4 is 81kg/h.
Finally 1130kg of beta-isophorone (beta-isophorone content: 99.0wt%, alpha-isophorone content: 0.24 wt%) was obtained, and the yield was 93.8%. 64kg of leftovers and 5.3wt% of leftovers.
Comparative example 3
The production system and the production method adopted in this comparative example were basically the same as those of example 1, except that the first transfer pump 7 was not turned on and the rectifying column 4 was filled with supported potassium p-toluenesulfonate.
The yield of the beta-isophorone was 58kg/h.
Finally, 1139kg of beta-isophorone (beta-isophorone content: 99.1wt%, alpha-isophorone content: 0.2 wt%) was obtained, and the yield was 94.6%. 53kg of leftovers and 4.4wt% of leftovers.
Comparative example 4
The production system and production method adopted in this comparative example are basically the same as those in example 1, except that:
Filling 5kg in a packed column Molecular sieves.
The yield of the beta-isophorone was 6kg/h.
874Kg of beta-isophorone (beta-isophorone content: 98.4% by weight, alpha-isophorone content: 0.57% by weight) was finally obtained, and the yield was 72.1%. 312kg of leftovers and 26.0wt% of leftovers.
The above embodiments are provided to illustrate the technical concept and features of the present invention and are intended to enable those skilled in the art to understand the content of the present invention and implement the same, and are not intended to limit the scope of the present invention. All equivalent changes or modifications made in accordance with the spirit of the present invention should be construed to be included in the scope of the present invention.
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
Claims (14)
1. The production method of the beta-isophorone is characterized in that the production system comprises a heater, a gas-liquid separator, a filling column and a rectifying tower which are sequentially arranged for heating and vaporizing the alpha-isophorone;
The catalyst is filled in the packed column;
The production method comprises the steps of heating and vaporizing alpha-isophorone through the heater, then enabling the alpha-isophorone to enter the gas-liquid separator for gas-liquid separation to obtain a gas material, enabling the gas material to enter the packed column, catalyzing the gas material by the catalyst, and then enabling the gas material to enter the rectifying tower for separation to obtain beta-isophorone;
The catalyst is a supported p-toluenesulfonate catalyst;
the carrier of the catalyst is one or a combination of a plurality of zeolite and molecular sieve;
The loading of the p-toluenesulfonate in the supported p-toluenesulfonate catalyst is 0.1-1.0wt%.
2. The method for producing beta-isophorone according to claim 1, wherein the method further comprises inputting the liquid material separated by the gas-liquid separator to a bottom of the rectifying tower.
3. The method for producing beta-isophorone according to claim 1, wherein the method further comprises feeding the starting material into a column bottom of the rectifying column to heat, and then conveying the material in the column bottom of the rectifying column to the heater to heat and gasify;
or/and, the production method further comprises the step of directly conveying the starting raw materials to the heater for heating and gasifying.
4. The method for producing beta-isophorone according to claim 1, wherein the reflux ratio of the top of the rectifying tower is controlled to be 4-8:1, and/or the theoretical plate number of the rectifying tower is controlled to be 30-60, and/or the temperature of the bottom of the rectifying tower is controlled to be 200-250 ℃, and the pressure in the rectifying tower is controlled to be 0.05-0.15 MPaA.
5. The method for producing beta-isophorone according to claim 4, wherein the temperature of the bottom of the rectifying tower is controlled to 220-230 ℃, and the pressure in the rectifying tower is controlled to be normal pressure.
6. The method for producing beta-isophorone according to claim 1, wherein the p-toluenesulfonate salt is one or a combination of a plurality of sodium p-toluenesulfonate and potassium p-toluenesulfonate.
7. The method for producing beta-isophorone according to claim 1, wherein the supported p-toluenesulfonate catalyst is prepared by immersing a carrier in an aqueous solution of p-toluenesulfonate, adsorbing and saturating, filtering, and drying.
8. The method for producing beta-isophorone according to any one of claims 1 to 4, wherein the heater has an inlet and an outlet, the gas-liquid separator has an inlet, a gas outlet and a liquid outlet, the inlet of the gas-liquid separator is communicated with the outlet pipe of the heater, the packed column has an inlet and an outlet, the inlet of the packed column is communicated with the gas outlet pipe of the gas-liquid separator, the column bottom of the rectifying column has a first inlet, a second inlet and an outlet, the second inlet of the column bottom is higher than the first inlet of the column bottom, the outlet of the column bottom is communicated with the inlet of the heater through a first connecting pipe, the first inlet of the column bottom is communicated with the liquid outlet of the gas-liquid separator through a second connecting pipe, and the second inlet of the column bottom is communicated with the outlet of the packed column through a third connecting pipe.
9. The method for producing beta-isophorone according to claim 8, wherein the first connecting tube is provided with a first transfer pump, the second connecting tube is provided with a second transfer pump, and/or the second connecting tube is provided with a regulating valve, and/or the production system further comprises a feeding tube connected with the first connecting tube.
10. The process for producing beta-isophorone according to claim 8, wherein the production system further comprises a condenser and a beta-isophorone receiving tank, the condenser has an inlet and an outlet, the inlet of the condenser is connected to the top of the rectifying column via a fourth connecting pipe, the outlet of the condenser is connected to the top of the rectifying column via a fifth connecting pipe, and the beta-isophorone receiving tank is connected to the fifth connecting pipe via a sixth connecting pipe.
11. A production system for producing beta-isophorone, which is characterized by comprising a heater for heating and vaporizing alpha-isophorone, a gas-liquid separator, a filling column filled with a catalyst inside and a rectifying tower, wherein the heater is provided with an inlet and an outlet, the gas-liquid separator is provided with an inlet, a gas outlet and a liquid outlet, the inlet of the gas-liquid separator is communicated with an outlet pipeline of the heater, the filling column is provided with an inlet and an outlet, the inlet of the filling column is communicated with a gas outlet pipeline of the gas-liquid separator, the rectifying tower is provided with a first inlet, a second inlet and an outlet, the second inlet of the rectifying tower is higher than the first inlet of the tower, the outlet of the tower is communicated with the inlet of the heater through a first connecting pipe, the first inlet of the tower is communicated with the liquid outlet of the gas-liquid separator through a second connecting pipe, and the second inlet of the tower is communicated with the outlet of the filling column through a third connecting pipe;
the alpha-isophorone is gasified by heating by the heater and then enters the gas-liquid separator to carry out gas-liquid separation, so as to obtain a gas material and a liquid material;
the gas material is introduced into the filling column, catalyzed by the catalyst and then enters the rectifying tower for separation, and the beta-isophorone is obtained;
And the liquid material is introduced into the tower kettle of the rectifying tower, and the material in the tower kettle of the rectifying tower enters the heater again or is discharged.
12. The production system of beta-isophorone according to claim 11, wherein the first connection tube is provided with a first transfer pump, the second connection tube is provided with a second transfer pump, and/or,
The second connecting pipe is provided with a regulating valve and/or,
The production system further comprises a feed pipe connected with the first connecting pipe, and/or,
The theoretical plate number of the rectifying tower is 30-60, and/or,
The production system further comprises a condenser and a beta-isophorone receiving tank, wherein the condenser is provided with an inlet and an outlet, the inlet of the condenser is connected with the top of the rectifying tower through a fourth connecting pipe, the outlet of the condenser is connected with the top of the rectifying tower through a fifth connecting pipe, and the beta-isophorone receiving tank is connected with the fifth connecting pipe through a sixth connecting pipe.
13. The system for producing beta-isophorone according to claim 11, wherein the catalyst is a supported p-toluenesulfonate catalyst.
14. The production system of beta-isophorone according to claim 13, wherein the carrier of the catalyst is one or more of zeolite and molecular sieve, and/or the p-toluenesulfonate is one or more of sodium p-toluenesulfonate and potassium p-toluenesulfonate, and/or the loading of p-toluenesulfonate in the supported p-toluenesulfonate catalyst is 0.1-1.0wt%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310500596.0A CN116514643B (en) | 2023-04-28 | 2023-04-28 | Production method and production system of beta-isophorone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310500596.0A CN116514643B (en) | 2023-04-28 | 2023-04-28 | Production method and production system of beta-isophorone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN116514643A CN116514643A (en) | 2023-08-01 |
| CN116514643B true CN116514643B (en) | 2025-02-28 |
Family
ID=87400748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310500596.0A Active CN116514643B (en) | 2023-04-28 | 2023-04-28 | Production method and production system of beta-isophorone |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116514643B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117024258B (en) * | 2023-10-08 | 2023-12-15 | 山东富宇石化有限公司 | Method for preparing beta-isophorone by catalysis of modified X-type molecular sieve |
| CN117603031A (en) * | 2023-11-22 | 2024-02-27 | 万华化学集团股份有限公司 | A kind of preparation method of β-isophorone |
| CN120054374A (en) * | 2025-04-25 | 2025-05-30 | 山东新和成精化科技有限公司 | Preparation device and method of pseudo ionone |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101875602A (en) * | 2009-04-30 | 2010-11-03 | 中国石油天然气股份有限公司 | Heterogeneous catalysis method for synthesizing isophorone from acetone |
| CN104311407A (en) * | 2014-09-29 | 2015-01-28 | 万华化学集团股份有限公司 | Environmental-friendly preparation process of 3,5,5-trimethyl-3-cyclohexene-1-ketone |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19821379A1 (en) * | 1998-05-13 | 1999-11-18 | Degussa | Improved process for the preparation of 3,5,5-trimethylcyclohexa-3-en-1-one (beta-isophorone by isomerization of 3,5,5-trimethylcyclohexa-2-en-1-one (alpha-isophorone) (II) |
| FR2795409B1 (en) * | 1999-06-22 | 2001-08-24 | Atofina | CONTINUOUS MANUFACTURING PROCESS OF 3,5,5-TRIMETHYL CYCLOHEXA- 3-IN-1-ONE (BETA-ISOPHORONE) |
| CN1259299C (en) * | 2004-12-10 | 2006-06-14 | 浙江大学 | A kind of synthetic technique of β-isophorone |
| CN104649878B (en) * | 2013-11-21 | 2017-01-04 | 浙江新和成药业有限公司 | A kind of technique of continuous synthesis β-isophorone |
| CN106278854B (en) * | 2015-06-05 | 2018-10-26 | 浙江新和成药业有限公司 | A kind of preparation method by α-isophorone isomery β-isophorone |
| CN112920032B (en) * | 2019-12-06 | 2022-07-12 | 万华化学集团股份有限公司 | Preparation method of beta-isophorone |
| CN114805045B (en) * | 2021-01-18 | 2023-10-20 | 万华化学(四川)有限公司 | Method for continuously preparing beta-isophorone |
| CN115433067B (en) * | 2022-08-23 | 2023-12-19 | 万华化学集团股份有限公司 | Preparation method of beta-isophorone |
| CN115677461B (en) * | 2022-10-27 | 2024-10-18 | 万华化学集团股份有限公司 | Method for continuously producing 4-oxo-isophorone by using tower reactor |
-
2023
- 2023-04-28 CN CN202310500596.0A patent/CN116514643B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101875602A (en) * | 2009-04-30 | 2010-11-03 | 中国石油天然气股份有限公司 | Heterogeneous catalysis method for synthesizing isophorone from acetone |
| CN104311407A (en) * | 2014-09-29 | 2015-01-28 | 万华化学集团股份有限公司 | Environmental-friendly preparation process of 3,5,5-trimethyl-3-cyclohexene-1-ketone |
Also Published As
| Publication number | Publication date |
|---|---|
| CN116514643A (en) | 2023-08-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN116514643B (en) | Production method and production system of beta-isophorone | |
| CN107082741B (en) | Method for synthesizing ethylene glycol through oxalate deep hydrogenation catalytic reaction | |
| CN107739301B (en) | Polymethoxy dimethyl ether synthesis system and process | |
| CN110437200B (en) | Preparation method of propylene carbonate based on carbon dioxide raw material | |
| CN106673938A (en) | Method for producing cyclopentene by selective hydrogenation of cyclopentadiene | |
| CN102337160B (en) | High-water-steam-ratio saturated hot water tower split CO transformation process | |
| CN102337159B (en) | Saturated hot water tower high-water-steam-ratio CO transformation process | |
| CN108558941A (en) | Rearranged reaction prepares 2- chloroethyl di(2-ethylhexyl)phosphates（2- chloroethyls）The method of ester | |
| CN104140357B (en) | Method for producing ethanol with acetic acid as raw material | |
| EP2925707B1 (en) | Method for dehydrating ethanol into ethylene, with pretreatment of the feedstock | |
| CN201988202U (en) | Ammonia evaporating system in process of preparing acrylonitrile through propylene ammoniation and oxidation | |
| CN214299942U (en) | Baffle plate rectifying equipment for propynol and butynediol aqueous solution system | |
| CN211078494U (en) | Urea catalytic hydrolysis ammonia production equipment | |
| CN104829452B (en) | Energy-saving production system of ethyl acetate and corresponding energy-saving production technology | |
| CN115677461A (en) | Method for continuously producing 4-oxoisophorone by using tower reactor | |
| CN112023852B (en) | Production device for preparing cyclohexene by benzene partial hydrogenation | |
| CN103980090B (en) | The production method of natural fatty alcohol | |
| CN111167378B (en) | Method for producing n-propyl acetate by continuous two-stage esterification reaction | |
| CN114349589B (en) | Method for preparing p-methyl ethylbenzene by using toluene and ethylene | |
| CN206447580U (en) | A kind of polycrystalline silicon production system of coupling | |
| CN1272482A (en) | Three-phase bubbling slurry bed methyl alcohol synthesizing process and its equipment | |
| CN111943873A (en) | Semi-continuous process and device for synthesizing m-phthalic acid dihydroxy ethyl ester-5-sodium sulfonate with high ester exchange rate through catalytic reaction rectification | |
| CN109289721B (en) | Device and method for quickly taking away reaction heat in preparation of propylene oxide by HPPO method | |
| CN219003010U (en) | System for synthesizing methanol by carbon dioxide hydrogenation | |
| CN221536620U (en) | Etherification reactor and reaction system for etherification separation of isoolefins |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20250319 Address after: 261000 No. 00268, Longwei Branch Road, Binhai District, Weifang, Shandong Patentee after: SHANDONG XINHECHENG FINE CHEMICAL TECHNOLOGY Co.,Ltd. Country or region after: China Patentee after: Xinchang XinHeCheng vitamin Co.,Ltd. Patentee after: ZHEJIANG NHU Co.,Ltd. Address before: 261108 No. 00887, Lingang West Road, Binhai Economic and Technological Development Zone, Weifang City, Shandong Province Patentee before: SHANDONG NHU VITAMIN Co.,Ltd. Country or region before: China Patentee before: Xinchang XinHeCheng vitamin Co.,Ltd. Patentee before: ZHEJIANG NHU Co.,Ltd. |