CN116102424A - High-purity AAEM purification process and purification system applied to process - Google Patents
High-purity AAEM purification process and purification system applied to process Download PDFInfo
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- CN116102424A CN116102424A CN202310198531.5A CN202310198531A CN116102424A CN 116102424 A CN116102424 A CN 116102424A CN 202310198531 A CN202310198531 A CN 202310198531A CN 116102424 A CN116102424 A CN 116102424A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Abstract
The application relates to the technical field of chemical separation and purification, and particularly discloses a high-purity AAEM purification process and a purification system applied to the process. A high purity AAEM purification process comprising the steps of: sequentially introducing carbon dioxide and water vapor into the AAEM reaction liquid to obtain an AAEM treatment liquid, and sequentially carrying out the steps of active adsorption and microfiltration on the AAEM treatment liquid to obtain an AAEM finished product, wherein the purity of the AAEM finished product is higher than 98%; the purification process can effectively separate HEMA from AAEM, reduce the content of HEMA and effectively improve the purity of AAEM; in addition, the purification process is simple to operate, mild and stable in reaction conditions, suitable for industrial production, good in quality of the purified AAEM product, capable of reaching more than 98% in purity and 97% in yield, and capable of effectively solving the difficult problem of difficult separation of the AAEM after-treatment.
Description
Technical Field
The application relates to the technical field of chemical synthesis and separation and purification, in particular to a high-purity AAEM purification process and a purification system applied to the process.
Background
Acetoacetoxy Ethyl Methacrylate (AAEM) is an important methacrylic monomer that can react with amines and nitriles to make it an ideal monomer for self-crosslinking, greenhouse curing acrylic emulsions. The AAEM has the advantages of low toxicity, easy copolymerization, good complexing performance and the like, and the special molecular structure of the AAEM enables the AAEM to have wide application in the fields of acrylic emulsion polymerization, unsaturated polyester resin-based resin, UV photo-curing, high polymer modification, paint industry and the like. The application potential of AAEM in industry is expanding continuously, and acetoacetate-based ethyl methacrylate (AAEM) is light yellow transparent liquid, is one of novel methacrylic acid monomers which are currently researched internationally more and have relatively large value, has the characteristics of low toxicity, easy copolymerization and the like, and has wide application in the aspects of high polymer synthesis and modification.
The acetoacetate-based ethyl methacrylate (AAEM) contains vinyl and dicarboxyl in the molecule, so that the acetoacetate-based ethyl methacrylate (AAEM) not only can synthesize methacrylic resin with special functions, but also can be used as a cross-linking agent of rubber, plastics and the like, and can be used for replacing N-methylolacrylamide, diacetone acrylamide, hydroxyethyl methacrylate and the like.
In the related art, the synthesis method of AAEM generally adopts hydroxyethyl methacrylate (HEMA) and ethyl acetoacetate as raw materials, and uses concentrated sulfuric acid as a catalyst to perform transesterification reaction for synthesis. The concentrated sulfuric acid has catalytic action on transesterification, oxidation, dehydration and other reactions, and a series of side reactions occur, so that the AAEM product purity is too low, the concentrated sulfuric acid serving as a catalyst cannot be recycled, and the method has a series of defects of high product loss, equipment corrosion and the like.
In addition, the synthesis method of AAEM can also adopt hydroxyethyl methacrylate and diketene to carry out addition reaction synthesis, and the post-treatment adopts purification methods such as molecular distillation, water washing and the like to carry out purification operation on AAEM. However, the AAEM product has the main difficulty in separation of post-treatment, and as the boiling point of AAEM is up to 273 ℃, and the polarity of HEMA is similar to that of AAEM, separation is difficult, and high-temperature rectification is extremely easy to polymerize, so that the product yield is low. At present, no effective separation report exists, and the HEMA content in the existing AAEM industrialized product is higher due to the fact that the post-treatment is difficult, and the product purity is generally lower than 96%.
Disclosure of Invention
In order to improve the technical defects of the Acetoacetic Acid Ethyl Methacrylate (AAEM) purification method in the related art, the invention provides a high-purity purification process and a purification system applied to the process, the purification process has mild reaction conditions, can effectively separate and purify impurities in the AAEM, can separate HEMA from the AAEM, and improves the product purity of the AAEM. The AAEM product purified by the purification process has good quality, the purity of the AAEM product reaches more than 98 percent, the yield is more than 97 percent, and the difficult problem of difficult separation of the AAEM after-treatment is solved.
In a first aspect, the present application provides a high purity AAEM purification process, which adopts the following technical scheme:
a high purity AAEM purification process comprising the steps of:
and sequentially introducing carbon dioxide and water vapor into the AAEM reaction liquid to obtain an AAEM treatment liquid, and sequentially carrying out the steps of active adsorption and microfiltration on the AAEM treatment liquid to obtain an AAEM finished product, wherein the purity of the AAEM finished product is higher than 98%.
By adopting the technical scheme, because the AAEM reaction liquid adopted by the application is obtained by an addition method of hydroxyethyl methacrylate and diketene under the catalysis of triethylamine, the AAEM reaction liquid contains a small amount of diketene, acetone, acetic anhydride, acetic acid, triethylamine, water, hydroxyethyl methacrylate, polycondensate, solid salt particles, colloid, mechanical impurities and other impurities, and because the boiling point of AAEM is up to 273 ℃, HEMA and AAEM have similar polarities, separation is difficult, and high-temperature rectification is easy to polymerize; moreover, as AAEM is insoluble in water, HEMA is miscible with water; therefore, the method can effectively remove hydroxyethyl methacrylate (HEMA) in AEMM by introducing steam, realize the rapid separation of HEMA and AAEM, ensure that the purified AAEM has higher purity, and solve the difficult problem of difficult separation of the AAEM after treatment, and has the advantages of mild purification method conditions, good product quality, product purity of more than 98 percent and yield of more than 97 percent.
Preferably, the specific purification steps are as follows:
step one: introducing weak acid gas into the AAEM reaction liquid for neutralizing triethylamine in the AAEM reaction liquid and removing low-boiling-point impurities in the AAEM reaction liquid;
step two: introducing water vapor into the AAEM reaction solution obtained in the step one, and removing impurities which react with or dissolve in water in the AAEM reaction solution to obtain AAEM treatment solution;
step three: the AAEM treatment liquid obtained in the second step is subjected to active soil adsorption treatment, so that the chromaticity of the AAEM treatment liquid is reduced, and the impurity content of polycondensates is reduced;
step four: and (3) carrying out microfiltration treatment on the AAEM treatment liquid obtained in the step (III) to remove solid impurities in the AAWM reaction liquid, thereby obtaining a high-purity AAEM finished product.
By adopting the technical scheme, in the first step, the weakly acidic gas is introduced mainly for neutralizing the catalyst triethylamine in the AAEM reaction liquid, and meanwhile, the weakly acidic gas can also take away part of low-boiling-point substances such as acetone and the like through flowing; in the second step, steam is introduced, mainly for removing impurities which react with water or are mutually soluble in the AAEM reaction liquid, such as impurities of diketene, acetone, acetic anhydride, acetic acid, hydroxyethyl methacrylate (HEMA) and the like, so that the content of the impurities is reduced to be within a qualified index range; in the third step, the AEMM treatment liquid is subjected to active soil adsorption treatment, and the purpose of the active soil is mainly to adsorb trace colored substances and polycondensates in the AEMM treatment liquid, so that the chromaticity of an adsorbed AAEM product is reduced to 0.2-0.6Gardner, and the content of polycondensates with the molecular weight of more than 500 is reduced to below 0.1%; in the fourth step, the AEMM treatment liquid is subjected to microfiltration treatment, mainly for removing solid salt, colloid, mechanical impurities and active soil and other particulate impurities carried in the AAEM treatment liquid, so that the impurity level of the finished product AAEM particles is lower, specifically +.0.2 μm particles are reduced to below 100/ml, therefore, the purification process is adopted to purify the AAEM, HEMA and AAEM can be effectively separated, the HEMA content is reduced, and the AAEM purity is higher than 98%.
Preferably, a pair ofThe flow rate of the weak acid gas is 1-10m 3 /h。
Preferably, in the second step, the steam is introduced under the pressure of-0.07 MPa to-0.1 MPa, and the temperature of the AAEM reaction solution is 50-80 ℃.
Through adopting the technical scheme, in the second step, the AAEM is subjected to heating treatment, and meanwhile, the water vapor is introduced under the pressure of-0.07 MPa to-0.1 MPa, so that the water vapor is kept from condensing, enters the AAEM reaction liquid in a gas form, and is then vacuumized.
Preferably, in the second step, the flow rate of the water vapor is 1-5m3/h, and the pressure is 0.1-1.5Mpa.
Preferably, in the third step, the adsorption treatment of the AAEM treatment liquid is performed under the pressure of-0.03 to-0.07 MPa.
Preferably, in the fourth step, the microfiltration treatment of the AAEM treatment fluid is carried out under the condition that the pressure is 0.01-0.2 mpa, and the flow rate of the AAEM treatment fluid is 0.02-2.0m 3 /h。
By adopting the technical scheme, the treatment efficiency of micro-filtration can be effectively improved by controlling the pressure and the flow rate of the filtrate, and meanwhile, the impurity level of the finished AAEM particles is lower, specifically, the particle size of 0.2 μm is reduced to below 100 particles/ml.
Preferably, in the third step, the chromaticity of the product after the AAEM treatment liquid is subjected to adsorption treatment is 0.2-0.6Gardner, and the content of polycondensate with the molecular weight of more than 500 in the AAEM treatment liquid is reduced to below 0.1%.
By adopting the technical scheme, the AAEM reaction liquid is generally deeper than 1.5-4.0 Gardner, and after adsorption treatment in the application, the chromaticity of the adsorbed AAEM product can be reduced to 0.2-0.6Gardner, and part of polycondensate can be adsorbed and removed, so that the polycondensate content of more than 500 molecular weight in the AAEM treatment liquid is reduced to below 0.1%.
Preferably, the AAEM reaction solution is obtained by an addition method of hydroxyethyl methacrylate (HEMA) and diketene under the catalysis of a triethylamine catalyst.
In a second aspect, the present application provides a high purity AAEM purification system, which adopts the following technical scheme:
the utility model provides a high purity AAEM purification system, includes dropwise add jar, reation kettle, gas collection jar, light component collection jar, comdenstion water collection jar, adsorption column, microporous filter device, middle receiving tank and filtrate collection jar, dropwise add jar, reation kettle, adsorption column, middle receiving tank, microporous filter device and filtrate collection jar series connection, light component collection jar and reation kettle intercommunication, just light component collection jar all communicates with gas collection jar and comdenstion water collection jar.
In summary, the present application has the following beneficial effects:
1. the method can effectively remove hydroxyethyl methacrylate (HEMA) in AEMM by introducing steam, realizes quick separation of HEMA and AAEM, ensures that the purified AAEM has higher purity, has mild conditions, good product quality, product purity of more than 98 percent and yield of more than 97 percent, and solves the difficult problem of difficult post-treatment separation of the AAEM.
2. And step two, heating AAEM, introducing water vapor under the pressure of-0.07 MPa to-0.1 MPa, keeping the water vapor not condensed, entering AAEM reaction liquid in a gas form, and then vacuumizing.
3. After adsorption treatment, the chromaticity of the adsorbed AAEM product can be reduced to 0.2-0.6Gardner, and part of polycondensate can be adsorbed and removed, so that the polycondensate content of the AAEM treatment liquid with the molecular weight of more than 500 is reduced to below 0.1%.
Drawings
FIG. 1 is a schematic diagram of a purification system provided herein;
FIG. 2 is a gas chromatogram of the AAEM reaction solution of example 1 of the present application;
FIG. 3 is a gas chromatogram of the AAEM finished product of example 1 of the present application;
reference numerals illustrate:
1. a dripping tank; 2. a reaction kettle; 3. a gas collection tank; 4. a light component collection tank; 5. a condensed water collection tank; 6. an adsorption column; 7. a microporous filter device; 8. an intermediate receiving tank; 9. a filtrate collection tank.
Detailed Description
The present application is described in further detail below in conjunction with figures 1-2 and examples. The specific description is as follows: the following examples, in which the specific conditions are not specified, are conducted under conventional conditions or conditions recommended by the manufacturer, and the raw materials used in the following examples are commercially available from ordinary sources except for the specific descriptions.
Examples
The embodiment of the application discloses a high-purity AAEM purification process and a purification system applied to the process.
The present embodiment discloses a purification system applied to a high purity AAEM purification process, referring to fig. 1, which includes a dropping tank 1, a reaction kettle 2, a gas collection tank 3, a light component collection tank 4, a condensed water collection tank 5, an adsorption column 6, a microporous filtering device 7, an intermediate receiving tank 8 and a filtrate collection tank 9, and the dropping tank 1, the reaction kettle 2, the adsorption column 6, the intermediate receiving tank 8, the microporous filtering device 7 and the filtrate collection tank 9 are connected in series communication. Namely, the bottom outlet of the dripping tank 1 is communicated with the top inlet of the reaction kettle 2, and the bottom of the reaction kettle 2 is provided with a gas inlet so as to be convenient for introducing weak acid gas and water vapor. Meanwhile, the bottom of the reaction kettle 2 is also communicated with the top inlet of the adsorption column 6; the bottom outlet of the adsorption column 6 is communicated with the inlet of the intermediate receiving tank 8, while the outlet of the intermediate receiving tank 8 is communicated with the inlet of the micro-filtration device 7, and the outlet of the micro-filtration device 7 is communicated with the inlet of the filtrate collecting tank 9.
The inlet of the light component collection tank 4 is also communicated with the top outlet of the reaction kettle 2, and the top outlet of the light component collection tank 4 is simultaneously communicated with the inlet of the gas collection tank 3 and the inlet of the condensed water collection tank 5.
Preparing AAEM reaction liquid: 88.2g of diketene is weighed and added into a dripping tank 1, 130g of hydroxyethyl methacrylate, 0.3g of triethylamine and 0.05g of hydroquinone are respectively weighed and added into a reaction kettle 2, and the mixture is stirred and heated to 40 ℃; then, slowly dripping diketene in the dripping tank 1 into the reaction kettle 2, and preserving heat for reaction for 1h after dripping; then, as can be seen from the GC detection by sampling and referring to FIG. 2, the reaction end point is the reaction end point which is the reaction end point with the hydroxyethyl methacrylate content of 4% or less, and the temperature is lowered to the room temperature, thereby obtaining AAEM reaction liquid.
The application also discloses a high-purity AAEM purification process, referring to fig. 1 and 3, specifically comprising the following steps:
step one: at a rate of 2m from the bottom of the reaction kettle 2 3 The weak acid gas is introduced at the flow rate/h, the weak acid gas adopted in the embodiment of the application is carbon dioxide, tail gas carbon dioxide is collected into the gas collection tank 3 through the light component collection tank 4, the carried-out part of light components such as acetone are collected into the light component collection tank 4, and the carbon dioxide can be subjected to neutralization reaction with triethylamine in the light component collection tank 4 when passing through the AAEM reaction liquid, so that the content of the triethylamine in the AAEM reaction liquid is reduced. And (3) introducing carbon dioxide for 2 hours, sampling and detecting that the triethylamine content in the reaction liquid is less than 0.01%, and stopping introducing the carbon dioxide.
Step two: after the carbon dioxide is introduced, a vacuum pump is started, heating is started, when the vacuum degree in the reaction kettle 2 is minus 0.08MPa and the temperature is 60 ℃, water vapor with the pressure of 1.0MPa is introduced from a gas inlet at the bottom of the reaction kettle 2, and the flow rate of the water vapor is 2m 3 And/h, keeping the vapor not condensed, entering the AAEM reaction liquid in a gas form, and then vacuumizing, wherein the process can reduce the content of impurities dissolved in water or reacted with water, such as diketene, acetone, acetic anhydride, acetic acid, hydroxyethyl methacrylate and the like, to be within a qualified index range. And then, collecting tail gas steam into a condensed water collecting tank 5 after passing through a light component collecting tank 4 and condensing, collecting the carried-out light component impurities into the light component collecting tank 4 for 1h to obtain AAEM treatment liquid, and then, sampling and detecting the content of the diketene 0.03559%, the acetone content 0.07761%, the acetic anhydride content 0.00802%, the acetic acid content 0.00816%, the hydroxyethyl methacrylate content 0.29818% and the AAEM content 98.65105% in the AAEM treatment liquid, and stopping introducing steam when the AAEM treatment liquid is subjected to water vapor.
Step three: after the water vapor is introduced, pumping AAEM treatment liquid from the bottom of the reaction kettle 2 to the top of an adsorption column 6 through a material pump, wherein the adsorption column 6 is filled with 0.1-2 times of active soil in volume. The activated soil is mainly for decolorizing treatment, so that decolorizing materials such as activated carbon, activated alumina, diatomite, silicon dioxide and bentonite can be selected, the activated soil adopted in the embodiment of the application is activated clay, and meanwhile, the bottom of the adsorption column 6 is communicated with the middle receiving tank 8, and AAEM treatment liquid passing through the adsorption column 6 can be collected in the middle receiving tank 8. The activated clay adsorption can remove trace colored substances and polycondensates in an AAEM treatment liquid system, the operation is carried out under the condition of vacuum negative pressure of-0.05 MPa, the sampling chromaticity detection of the adsorbed AAEM treatment liquid is 0.5Gardner, and the GC content of the polycondensate with the molecular weight of more than 500 is 0.03%.
Step four: the AAEM treatment liquid in the intermediate receiving tank 8 after being adsorbed by the activated clay is pumped into the micro-pore filter device 7 through the material pump, and a micron-sized filter element is arranged in the micro-pore filter device 7, wherein the aperture of the filter element is 0.1 micron. The microporous filtering device 7 is filled with nitrogen gas to be pressurized to 0.1MPa, and the flow rate of the AAEM treatment liquid serving as filtrate is 0.5m 3 And (3) collecting the AAEM treatment liquid in a filtrate collecting tank 9 through a microporous filtering device 7, wherein 213.6g of filtrate in the filtrate collecting tank 9 is the AAEM finished product, and the yield of the AAEM finished product is 97.7% through calculation.
The foregoing are all preferred embodiments of the present application, and are not intended to limit the scope of the present application in any way. Wherein like parts are designated by like reference numerals. It should be noted that the words "front", "back", "left", "right", "upper" and "lower" used in the above description refer to directions in the drawings, and the words "inner" and "outer" refer to directions toward or away from, respectively, the geometric center of a particular component. Therefore: all equivalent changes in structure, shape and principle of this application should be covered in the protection scope of this application.
Claims (10)
1. The high-purity AAEM purification process is characterized by comprising the following steps of:
and sequentially introducing carbon dioxide and water vapor into the AAEM reaction liquid to obtain an AAEM treatment liquid, and sequentially carrying out the steps of active adsorption and microfiltration on the AAEM treatment liquid to obtain an AAEM finished product, wherein the purity of the AAEM finished product is higher than 98%.
2. The high purity AAEM purification process of claim 1, wherein the specific purification steps are as follows:
step one: introducing weak acid gas into the AAEM reaction liquid for neutralizing triethylamine in the AAEM reaction liquid and removing low-boiling-point impurities in the AAEM reaction liquid;
step two: introducing water vapor into the AAEM reaction solution obtained in the step one, and removing impurities which react with or dissolve in water in the AAEM reaction solution to obtain AAEM treatment solution;
step three: the AAEM treatment liquid obtained in the second step is subjected to active soil adsorption treatment, so that the chromaticity of the AAEM treatment liquid is reduced, and the impurity content of polycondensates is reduced;
step four: and (3) carrying out microfiltration treatment on the AAEM treatment liquid obtained in the step (III) to remove solid impurities in the AAWM reaction liquid, thereby obtaining a high-purity AAEM finished product.
3. The high purity AAEM purification process of claim 2, wherein in step one, the flow rate of the weakly acidic gas is 1 to 10m 3 /h。
4. The process according to claim 2, wherein in the second step, the introduction of steam is performed under a pressure of-0.07 MPa to-0.1 MPa, and the temperature of the AAEM reaction solution is 50-80 ℃.
5. The high purity AAEM purification process of claim 2, wherein in step two, the flow rate of the water vapor is 1-5m 3 And the pressure is 0.1-1.5Mpa.
6. The process according to claim 2, wherein in the third step, the adsorption treatment of the AAEM treating liquid is performed under a pressure of-0.03 to-0.07 MPa.
7. The process according to claim 2, wherein in the fourth step, the microfiltration of the AAEM treating fluid is performed under a pressure of 0.01-0.2 mpa, and the flow rate of the AAEM treating fluid is 0.02-2.0m 3 /h。
8. The process according to claim 2, wherein in step three, the color of the product after the adsorption treatment of the AAEM treatment liquid is 0.2-0.6Gardner, and the polycondensate content of more than 500 molecular weight in the AAEM treatment liquid is reduced to below 0.1%.
9. The process for purifying high-purity AAEM according to claim 1, wherein the AAEM reaction solution is obtained by an addition method of hydroxyethyl methacrylate (HEMA) and diketene under the catalysis of a triethylamine catalyst.
10. The high-purity AAEM purification system is applied to the high-purity AAEM purification process according to any one of claims 1-9, and is characterized by comprising a dripping tank (1), a reaction kettle (2), a gas collecting tank (3), a light component collecting tank (4), a condensed water collecting tank (5), an adsorption column (6), a microporous filtering device (7), an intermediate receiving tank (8) and a filtrate collecting tank (9), wherein the dripping tank (1), the reaction kettle (2), the adsorption column (6), the intermediate receiving tank (8), the microporous filtering device (7) and the filtrate collecting tank (9) are connected in series connection, the light component collecting tank (4) is communicated with the reaction kettle (2), and the light component collecting tank (4) is communicated with the gas collecting tank (3) and the condensed water collecting tank (5).
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116947640A (en) * | 2023-09-21 | 2023-10-27 | 深圳市普利凯新材料股份有限公司 | Purification method of acetoacetyl ethyl methacrylate |
| CN117024279A (en) * | 2023-10-10 | 2023-11-10 | 深圳市普利凯新材料股份有限公司 | Decoloring method of acetoacetic acid ethyl methacrylate |
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2023
- 2023-03-03 CN CN202310198531.5A patent/CN116102424A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116947640A (en) * | 2023-09-21 | 2023-10-27 | 深圳市普利凯新材料股份有限公司 | Purification method of acetoacetyl ethyl methacrylate |
| CN116947640B (en) * | 2023-09-21 | 2023-12-15 | 深圳市普利凯新材料股份有限公司 | Purification method of acetoacetyl ethyl methacrylate |
| CN117024279A (en) * | 2023-10-10 | 2023-11-10 | 深圳市普利凯新材料股份有限公司 | Decoloring method of acetoacetic acid ethyl methacrylate |
| CN117024279B (en) * | 2023-10-10 | 2023-12-15 | 深圳市普利凯新材料股份有限公司 | Decoloring method of acetoacetic acid ethyl methacrylate |
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