CN111632629A - Method for recovering ionic liquid catalyst in preparation process of coal-based methacrolein - Google Patents
Method for recovering ionic liquid catalyst in preparation process of coal-based methacrolein Download PDFInfo
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- CN111632629A CN111632629A CN202010583758.8A CN202010583758A CN111632629A CN 111632629 A CN111632629 A CN 111632629A CN 202010583758 A CN202010583758 A CN 202010583758A CN 111632629 A CN111632629 A CN 111632629A
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
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- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
- B01J38/50—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids
- B01J38/52—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids oxygen-containing
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- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
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- 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
- C07C45/68—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 by increase in the number of carbon atoms
- C07C45/72—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 by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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Abstract
The invention relates to a method for recovering an ionic liquid catalyst in a coal-based methacrolein preparation process, which utilizes a plurality of means to remove organic impurities and redundant water from ionic liquid, and comprises the steps of firstly separating a methacrolein phase and an ionic liquid catalyst phase after reaction, then carrying out solvent extraction on the ionic liquid catalyst phase, finally adding the extracted ionic liquid catalyst phase into a film evaporation device for film evaporation, and collecting the obtained heavy component, namely the recovered ionic liquid catalyst; the invention combines phase separation, extraction and thin film evaporation, on one hand, residual organic matters in the ionic liquid phase can be effectively reduced, on the other hand, excessive water and the like brought by reaction can be effectively removed, so that the obtained ionic liquid has high purity and proper water content, and is beneficial to multiple uses. The method has the advantages of simple process, convenient operation, low energy consumption, high purity of the obtained catalyst and stable catalytic effect after multiple treatments.
Description
Technical Field
The invention relates to a method for recovering an ionic liquid catalyst, in particular to a method for recovering an ionic liquid catalyst in a coal-based methacrolein preparation process.
Technical Field
Methacrolein is an important chemical raw material, methacrylic acid can be prepared by oxygen molecular oxidation, and methyl methacrylate can be further prepared by esterification reaction of the methacrylic acid and methanol; the methyl allyl alcohol can be prepared by aldehyde group reduction; as a polymerization monomer, the product can be used for producing surface coatings, such as water-based coatings, solvent-based coatings, emulsion paints and the like, can be used as a raw material to generate impact modifiers ACR and MRS which can effectively improve the rigidity, toughness, dimensional stability, processing fluidity and color tone of polyvinyl chloride (PVC) products, and can also be used as an adhesive, a cross-linking agent, an additive and the like.
In the past, the synthesis of methacrolein mostly adopts an isobutene/tert-butyl alcohol high-temperature catalytic oxidation method, namely mixed raw material gas containing isobutene/tert-butyl alcohol and oxygen is subjected to catalytic oxidation reaction through a solid catalyst bed layer, the reaction temperature is 300-400 ℃, the retention time is about 2-5 s, the conversion rate of isobutene is more than 95%, and the yield of methacrolein and methacrylic acid is 82-88%. The method for preparing the methacrolein has low selectivity and high reaction energy consumption, and the solid catalyst is not beneficial to mass transfer.
In recent years, researchers at home and abroad increasingly study on the low-temperature synthesis of methacrolein by using a coal-based liquid phase, namely, methacrolein is obtained by taking formaldehyde and propionaldehyde as raw materials through aldol condensation. The reported catalysts are different from each other and are summarized to be mainly amine ionic liquid organic acid salts or inorganic acid salts and other ionic liquid salts. An ionic liquid catalyst is a new liquid which has been recently developed, and is more and more favored by scientists because of its advantages such as diversity, designability, low vapor pressure, and the like. In the process of preparing methyl methacrylate by ethylene carbonylation method initiated by BASF company, the preparation of methacrolein adopts Mannich reaction formaldehyde and propionaldehyde condensation method, the catalyst is secondary amine halogen salt or secondary amine organic acid salt, patent CN101074192A uses diethylamine hydrochloride as catalyst, US4408079 uses secondary amine and carboxylic acid as catalyst, US2639295 and other patents use organic amine and inorganic acid as catalyst, the literature reports on the catalyst are many, but the research on the recovery of ionic liquid catalyst after preparing methacrolein is less.
The ionic liquid catalyst is used as an excellent catalyst, has good catalytic effect, greatly improves the reaction and the reaction process, and has stable property, high efficiency, low corrosivity, mild reaction process, high yield of the methacrolein and high purity of the prepared methacrolein. But good economics can only be achieved with multiple uses of ionic liquid catalysts. The recovery and reuse of ionic liquids are of great significance both from an economic and environmental perspective.
In respect to the recovery of ionic liquid, a great deal of reports are provided, and in patent CN101219840A, a combined method of pretreatment, ultrafiltration, nanofiltration and reduced pressure distillation is adopted to recover an ionic liquid solvent from spinning wastewater; some patents have added inorganic salts to ionic liquids to recover ionic liquids, such as CN 1973943A; some employ ion exchange resins to recover ionic liquids, such as 200819200367.2; these patents are viable for the recovery of small amounts of ionic liquid, but are not applicable for the recovery of large amounts of ionic liquid and for ionic liquids with high water content. The patent reports mainly the recovery of ionic liquid solvent and little to no recovery of ionic liquid catalyst.
The thin film evaporation is a quick and efficient special liquid-liquid separation technology, the separation temperature can be far lower than the boiling point, meanwhile, the retention time of materials is short, and the thin film evaporation is favorable for separating materials with high boiling points, heat sensitivity and easy oxidation; the thin film evaporation is carried out under high vacuum, the materials are not easy to oxidize and damage, and the mass transfer efficiency and the heat transfer efficiency are high under the thin film state; the liquid boiling during the distillation process is weak and no bubbling occurs. As a mild and efficient liquid-liquid separation method, thin film evaporation is widely used for separating high molecular weight, high boiling point, high viscosity, heat sensitivity and easily oxidized substances in petrochemical, food, daily chemical, medicine and other industries.
Disclosure of Invention
Based on the existing recovery method of the ionic liquid catalyst, particularly aiming at the problems that the recovery method of the ionic liquid catalyst is few and is not applicable in the preparation process of the coal-based methacrolein, the invention particularly provides a novel recovery method of the ionic liquid catalyst in the preparation process of the coal-based methacrolein.
The ionic liquid catalyst phase in the preparation process of the coal-based methacrolein mainly has the following characteristics: 1) the mutual solubility of the methacrolein and the ionic liquid catalyst is not large, and the layering is easy; 2) the reaction is complex, and the organic substances after the reaction have more components and are partially dissolved in the ionic liquid phase; 3) the ionic liquid catalyst system contains water, the water content of the raw material formaldehyde is large, water is generated by reaction, and the like, so that the water content of the ionic liquid catalyst phase after the reaction is high; 4) the ionic liquid catalyst is easy to generate other reactions at high temperature and easy to denature after being heated for a long time.
Aiming at the characteristics of the ionic liquid catalyst phase in the preparation process of the coal-based methacrolein, the invention provides a novel method for recovering the ionic liquid catalyst. The method combines the phase separation, extraction and thin film evaporation technologies, on one hand, residual organic matters in the ionic liquid phase can be effectively reduced, on the other hand, excessive water and the like brought by reaction can be effectively removed, so that the obtained ionic liquid has high purity and proper water content, and is beneficial to multiple uses. The method has the advantages of simple process, convenient operation, low energy consumption, high purity of the obtained catalyst and repeated recycling.
The invention relates to a method for recovering an ionic liquid catalyst in a coal-based methacrolein preparation process, which is to recover the ionic liquid catalyst in the coal-based methacrolein preparation process by combining a standing phase splitting method, a solvent extraction method and a film evaporation method, wherein firstly, a product after reaction is subjected to phase splitting to obtain an ionic liquid catalyst phase, and then the ionic liquid catalyst phase is subjected to solvent extraction and film evaporation in sequence, and the method comprises the following specific steps:
(1) quickly cooling a product after reaction, standing and layering for a period of time at a certain temperature to respectively obtain a methacrolein phase and an ionic liquid catalyst phase;
(2) adding a certain amount of extraction solvent into the ionic liquid catalyst phase obtained in the first step at a certain temperature, stirring for a certain time, and then carrying out extraction phase splitting to obtain an extractant phase and an extracted ionic liquid catalyst phase;
(3) and adding the extracted ionic liquid catalyst phase into a thin film evaporator, and performing thin film evaporation by adjusting the feeding speed, the film scraping temperature, the film scraping pressure, the film scraping speed and the condensation temperature to obtain the recyclable ionic liquid catalyst aqueous solution.
In the invention, the phase separation temperature in the step (1) is 0-30 ℃, and the phase separation time is 0-3 h.
In the invention, the extractant is at least one of benzene, toluene, diethyl ether, carbon tetrachloride, hexane and cyclohexane, the dosage of the extractant is 30-200% of the mass of the ionic liquid catalyst phase in the step (1), the extraction temperature is 20-80 ℃, the extraction time is 1-60 min, and the extraction times are not limited.
In the invention, the evaporation pressure of the film is 5-35 bar, and the temperature is 50-100 ℃.
In the invention, the coal-based methacrolein preparation process is to prepare methacrolein by liquid phase condensation of formaldehyde and propionaldehyde.
In the invention, the ionic liquid catalyst system is an organic acid salt or inorganic acid salt aqueous solution of amines or alcohol amines.
Detailed Description
The present invention is described by the following examples, but the present invention is not limited to the following examples, and variations and implementations are included in the technical scope of the present invention without departing from the spirit of the invention described above and below.
Example 1
Rapidly cooling the reacted mixed solution containing formaldehyde, propionaldehyde, methacrolein, water, diethylamine acetate and the like, standing for 1h at 30 ℃, and layering to obtain 2144g of ionic liquid catalyst phase after the two-phase interface is clear; adding 2100g of cyclohexane solution into the ionic liquid catalyst phase at 70 ℃, extracting and phase-separating for 10min, and extracting for three times under the same conditions; adding the extracted diethylamine acetate ionic liquid phase into a thin film evaporator feeder, keeping the liquid temperature at 25 ℃, starting a heating device, setting the evaporation surface temperature at 60 ℃, starting a circulating cooling pump, setting the internal condensation temperature at-20 ℃, setting the secondary condensation temperature at-20 ℃, adding liquid nitrogen, starting a vacuum pump, enabling the pressure to reach 35bar, starting a film scraper, enabling the rotating speed of a film scraping rotor to be 85r/min, opening a feeding valve, controlling the feeding speed at 15ml/min, starting film scraping, collecting the obtained heavy components into a recovered ionic liquid catalyst diethylamine acetate aqueous solution, and enabling other components to pass through secondary condensation and a liquid nitrogen cold trap to obtain light components with different compositions.
Example 2
Quickly cooling the reacted mixed solution containing formaldehyde, propionaldehyde, methacrolein, water, diethanolamine acetate and the like, standing for 2 hours at 0 ℃, and layering to obtain 1852g of ionic liquid catalyst phase after the two-phase interface is clear; adding 3600g of hexane solution into the ionic liquid catalyst phase at 40 ℃, extracting and phase-separating for 30min, and extracting twice under the same conditions; adding the extracted diethanolamine acetate ionic liquid phase into a thin film evaporator feeder, keeping the liquid temperature at 40 ℃, starting a heating device, setting the evaporation surface temperature at 90 ℃, starting a circulating cooling pump, setting the internal condensation temperature at 0 ℃, setting the secondary condensation temperature at-20 ℃, adding liquid nitrogen, starting a vacuum pump to enable the pressure to reach 15bar, starting a film scraper to enable the rotating speed of a film scraping rotor to be 105r/min, opening a feeding valve, controlling the feeding speed at 25ml/min, starting film scraping, collecting the obtained heavy components into a recovered ionic liquid catalyst diethanolamine acetate aqueous solution, and enabling other components to pass through secondary condensation and a liquid nitrogen cold trap to obtain light components with different compositions.
Example 3
Quickly cooling the reacted mixed solution containing formaldehyde, propionaldehyde, methacrolein, water, diethanolamine hydrochloride and the like, standing for 1.5h at 15 ℃, and layering to obtain 800g of ionic liquid catalyst phase when the interfaces of the two phases are clear; adding 400g of benzene solution into the ionic liquid catalyst phase at 80 ℃, extracting and phase-separating for 10min, and extracting for 5 times under the same conditions; adding the extracted diethanolamine hydrochloride ionic liquid into a feeder of a thin film evaporator, keeping the liquid temperature at 20 ℃, starting a heating device, setting the evaporation surface temperature at 50 ℃, starting a circulating cooling pump, setting the internal condensation temperature at 10 ℃, setting the secondary condensation temperature at-20 ℃, adding liquid nitrogen, starting a vacuum pump to enable the pressure to reach 5bar, starting a film scraper to enable the rotating speed of a film scraping rotor to be 125r/min, opening a feed valve, controlling the feed speed to be 30ml/min, starting film scraping, collecting the obtained heavy components into a recovered ionic liquid catalyst diethanolamine hydrochloride aqueous solution, and enabling other components to pass through secondary condensation and a liquid nitrogen cold trap to obtain light components with different compositions.
Example 4
Quickly cooling the reacted mixed solution containing formaldehyde, propionaldehyde, methacrolein, water, diethylamine phosphate and the like, standing for 2 hours at 25 ℃, and layering to obtain 1000g of ionic liquid catalyst phase when the interfaces of the two phases are clear; adding 1500g of ether solution into the ionic liquid catalyst phase at 20 ℃, extracting and phase-separating for 20min, and extracting twice under the same conditions; adding the extracted diethylamine phosphate ionic liquid phase into a thin film evaporator feeder, keeping the liquid temperature at 20 ℃, starting a heating device, setting the evaporation surface temperature at 100 ℃, starting a circulating cooling pump, setting the internal condensation temperature at 20 ℃, setting the secondary condensation temperature at-10 ℃, adding liquid nitrogen, starting a vacuum pump to enable the pressure to reach 20bar, starting a film scraper to enable the rotating speed of a film scraping rotor to be 150r/min, opening a feeding valve, controlling the feeding speed at 50ml/min, starting film scraping, collecting the obtained heavy components into a recovered ionic liquid catalyst diethylamine phosphate aqueous solution, and enabling other components to pass through secondary condensation and a liquid nitrogen cold trap to obtain light components with different compositions.
Example 5
Quickly cooling the reacted mixed solution containing formaldehyde, propionaldehyde, methacrolein, water, diethanolamine sulfonate and the like, standing for 3 hours at 20 ℃, and layering to obtain 500g of ionic liquid catalyst phase after the two-phase interface is clear; adding 150g of carbon tetrachloride solution into the ionic liquid catalyst phase at 60 ℃, extracting and phase-separating for 30min, and extracting for four times under the same conditions; adding the extracted diethanolamine sulfonate ionic liquid phase into a feeder of a thin film evaporator, keeping the liquid temperature at 50 ℃, starting a heating device, setting the evaporation surface temperature at 100 ℃, starting a circulating cooling pump, setting the internal condensation temperature at 20 ℃, setting the secondary condensation temperature at 0 ℃, adding liquid nitrogen, starting a vacuum pump to enable the pressure to reach 25bar, starting a film scraper to enable the rotating speed of a film scraping rotor to be 150r/min, opening a feeding valve, controlling the feeding speed at 50ml/min, starting film scraping, collecting the obtained heavy components into a recovered ionic liquid catalyst diethanolamine sulfonate aqueous solution, and enabling other components to pass through secondary condensation and a liquid nitrogen cold trap to obtain light components with different compositions.
Example 6
Quickly cooling the reacted mixed solution containing formaldehyde, propionaldehyde, methacrolein, water, diethanolamine acetate and the like, standing for 0.5h at 30 ℃, and layering to obtain 1811g of an ionic liquid catalyst phase when the interfaces of the two phases are clear; adding 2000g of toluene solution into the ionic liquid catalyst phase at 30 ℃, extracting and phase splitting for 60min, and extracting for three times under the same conditions; adding the extracted diethanolamine acetate ionic liquid phase into a thin film evaporator feeder, keeping the liquid temperature at 30 ℃, starting a heating device, setting the evaporation surface temperature at 80 ℃, starting a circulating cooling pump, setting the internal condensation temperature at-20 ℃, setting the secondary condensation temperature at-20 ℃, adding liquid nitrogen, starting a vacuum pump to enable the pressure to reach 10bar, starting a film scraper to enable the rotating speed of a film scraping rotor to be 85r/min, opening a feeding valve, controlling the feeding speed at 15ml/min, starting film scraping, collecting the obtained heavy component into a recovered ionic liquid catalyst diethanolamine acetate aqueous solution, and enabling other components to pass through secondary condensation and a liquid nitrogen cold trap to obtain light components with different compositions.
Example 7
The catalyst before reaction is a catalyst which is recycled for many times, the mixed solution containing formaldehyde, propionaldehyde, methacrolein, water, diethanolamine acetate and the like after reaction is rapidly cooled and then stands for 0.5h at 30 ℃, and 1875g of ionic liquid catalyst phase is obtained after two-phase interfaces are clear and layered; adding 2100g of toluene solution into the ionic liquid catalyst phase at 30 ℃, extracting and phase separating for 50min, and extracting for five times under the same conditions; adding the extracted diethanolamine acetate ionic liquid phase into a thin film evaporator feeder, keeping the liquid temperature at 30 ℃, starting a heating device, setting the evaporation surface temperature at 80 ℃, starting a circulating cooling pump, setting the internal condensation temperature at-20 ℃, setting the secondary condensation temperature at-20 ℃, adding liquid nitrogen, starting a vacuum pump to enable the pressure to reach 10bar, starting a film scraper to enable the rotating speed of a film scraping rotor to be 85r/min, opening a feeding valve, controlling the feeding speed at 17ml/min, starting film scraping, collecting the obtained heavy component into a recovered ionic liquid catalyst diethanolamine acetate aqueous solution, and enabling other components to pass through secondary condensation and a liquid nitrogen cold trap to obtain light components with different compositions.
Comparative example 1
The first and third steps were the same as in example 6, except that no extraction was performed. Rapidly cooling the reacted mixed solution containing formaldehyde, propionaldehyde, methacrolein, water, diethanolamine acetate and the like, standing for 0.5h at 30 ℃, and layering when the two-phase interface is clear to obtain 1811g of the ionic liquid catalyst; directly adding the layered diethanolamine acetate ionic liquid phase into a thin film evaporator feeder, keeping the liquid temperature at 30 ℃, starting a heating device, setting the evaporation surface temperature at 80 ℃, starting a circulating cooling pump, setting the internal condensation temperature at-20 ℃, setting the secondary condensation temperature at-20 ℃, adding liquid nitrogen, starting a vacuum pump to enable the pressure to reach 10bar, starting a film scraper to enable the rotating speed of a film scraping rotor to be 85r/min, opening a feeding valve, controlling the feeding speed at 15ml/min, starting film scraping, collecting the obtained heavy component into a recovered ionic liquid catalyst diethanolamine acetate aqueous solution, and obtaining light components with different compositions by secondary condensation and a liquid nitrogen cold trap for other components.
Comparative example 2
The second and third steps were the same as in example 6, except that the extraction was carried out without phase separation. 2523g of the reacted mixture containing formaldehyde, propionaldehyde, methacrolein, water, diethanolamine acetate and the like; adding 2800g of toluene solution into the mixed solution at 30 ℃ for extraction phase separation for 1h, and extracting for three times under the same conditions; adding the extracted diethanolamine acetate ionic liquid phase into a thin film evaporator feeder, keeping the liquid temperature at 30 ℃, starting a heating device, setting the evaporation surface temperature at 80 ℃, starting a circulating cooling pump, setting the internal condensation temperature at-20 ℃, setting the secondary condensation temperature at-20 ℃, adding liquid nitrogen, starting a vacuum pump to enable the pressure to reach 10bar, starting a film scraper to enable the speed of a film scraping rotor to be 85r/min, opening a feeding valve, controlling the feeding speed at 15ml/min, starting film scraping, collecting the obtained heavy component into a recovered ionic liquid catalyst diethanolamine acetate aqueous solution, and enabling other components to pass through secondary condensation and a liquid nitrogen cold trap to obtain light components with different compositions.
Comparative example 3
The first and second steps were the same as in example 6, and the third step was conducted by distillation under reduced pressure. Quickly cooling the reacted mixed solution containing formaldehyde, propionaldehyde, methacrolein, water, diethanolamine acetate and the like, standing for 0.5h at 30 ℃, and layering to obtain 1811g of an ionic liquid catalyst phase when the interfaces of the two phases are clear; 2000g of toluene solution is added into the ionic liquid catalyst phase at 30 ℃, and phase separation is carried out for 1h by extraction under the same conditions for three times. And (3) distilling the extracted diethanolamine acetate ionic liquid phase under reduced pressure at the temperature of 80 ℃ and the pressure of 0.1Mpa and water cooling at the temperature of minus 20 ℃, and obtaining the heavy component ionic liquid catalyst diethanolamine acetate aqueous solution and light components after 4 hours.
| Catalyst and process for preparing same | Content of ionic liquid% | Water content% | Content of impurities% | Colour(s) |
| Fresh catalyst | 60 | 40 | 0 | Is transparent |
| EXAMPLE 1 | 59.3 | 40.3 | 0.4 | Light yellow |
| EXAMPLE 2 | 59.2 | 40.6 | 0.2 | Light yellow |
| EXAMPLE 3 | 59.4 | 39.8 | 0.8 | Light yellow |
| EXAMPLE 4 | 59.1 | 40.1 | 0.8 | Light yellow |
| EXAMPLE 5 | 58.9 | 41.1 | 0.6 | Light yellow |
| EXAMPLE 6 | 59.7 | 40.1 | 0.2 | Light yellow |
| EXAMPLE 7 | 59.6 | 40.2 | 0.2 | Light yellow |
| Comparative example 1 | 58.1 | 40.3 | 1.6 | Light yellow |
| Comparative example 2 | 57.4 | 40.6 | 2 | Deep yellow |
| Comparative example 3 | 55.8 | 41.8 | 2.4 | Brown colour |
Claims (6)
1. The method for recovering the ionic liquid catalyst in the coal-based methacrolein preparation process is to recover the ionic liquid catalyst in the coal-based methacrolein preparation process by combining the standing phase splitting, the solvent extraction and the thin film evaporation, firstly, the phase splitting is carried out on the mixed solution after the reaction to obtain the ionic liquid catalyst phase, and then, the solvent extraction and the thin film evaporation are carried out on the ionic liquid catalyst phase in sequence, and the method comprises the following specific steps:
(1) quickly cooling the reacted mixed solution, standing at a certain temperature for phase splitting to respectively obtain a methacrolein phase and an ionic liquid catalyst phase;
(2) adding a certain amount of extractant into the ionic liquid catalyst phase obtained in the step (1), mixing and extracting at a certain temperature, and separating phases to obtain an extractant phase and an extracted ionic liquid catalyst phase;
(3) and (3) carrying out film evaporation on the extracted ionic liquid catalyst phase, and obtaining the recyclable ionic liquid catalyst aqueous solution after the film evaporation.
2. The method for recovering the ionic liquid catalyst in the preparation process of coal-based methacrolein according to claim 1, wherein: in the step (1), the phase separation temperature is 0-30 ℃, and the phase separation time is 0-3 h.
3. The method for recovering the ionic liquid catalyst in the preparation process of coal-based methacrolein according to claim 1, wherein: the extractant is at least one of benzene, toluene, diethyl ether, carbon tetrachloride, hexane and cyclohexane, the dosage of the extractant in the step (2) is 30-200% of the mass of the ionic liquid catalyst phase in the step (1), the extraction temperature is 20-80 ℃, the extraction time is 1-60 min, and the extraction times are not limited.
4. The method for recovering the ionic liquid catalyst in the preparation process of coal-based methacrolein according to claim 1, wherein: in the step (3), the evaporation pressure of the film is 5-35 bar, and the temperature is 50-100 ℃.
5. The process for preparing coal-based methacrolein according to claims 1 to 4, wherein the process is a process for preparing methacrolein by liquid phase condensation of formaldehyde and propionaldehyde.
6. The ionic liquid catalyst as claimed in claims 1 to 4, wherein the ionic liquid catalyst is amine organic acid salt or inorganic acid salt.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114264740A (en) * | 2021-12-13 | 2022-04-01 | 青岛三力本诺新材料股份有限公司 | Method for measuring effective components in circulating catalyst for synthesizing methacrolein |
| CN114264740B (en) * | 2021-12-13 | 2024-05-31 | 青岛三力本诺新材料股份有限公司 | Method for measuring effective components in circulating catalyst for synthesizing methacrolein |
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| CN104311403A (en) * | 2014-10-08 | 2015-01-28 | 中国科学院过程工程研究所 | Production method for methylacrolein |
| CN206746044U (en) * | 2017-05-18 | 2017-12-15 | 天津神侬环保科技有限公司 | A kind of ionic-liquid catalyst regenerates extraction equipment |
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| CN114264740A (en) * | 2021-12-13 | 2022-04-01 | 青岛三力本诺新材料股份有限公司 | Method for measuring effective components in circulating catalyst for synthesizing methacrolein |
| CN114264740B (en) * | 2021-12-13 | 2024-05-31 | 青岛三力本诺新材料股份有限公司 | Method for measuring effective components in circulating catalyst for synthesizing methacrolein |
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