CN114262269B - Preparation method of propylene glycol methyl ether acetate - Google Patents
Preparation method of propylene glycol methyl ether acetate Download PDFInfo
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Abstract
The application is applicable to the technical field of chemistry, and provides a preparation method of propylene glycol methyl ether acetate, which comprises the following steps: (1) Placing industrial grade propylene glycol methyl ether acetate into a distillation tower for rectification, controlling the temperature of the top of the tower to 145-147 ℃ and the reflux ratio to be 1: (2-3) and condensing water at 1-5 ℃ to obtain fractions; the organic purity of the fraction is more than or equal to 99.99 percent, and the content of single metal impurities of the fraction is less than or equal to 1ppb; (2) Placing the fraction obtained in the step (1) in a middle tank, connecting the middle tank to a filtering system through a connecting pipeline, and filtering the fraction through the filtering system to obtain propylene glycol methyl ether acetate; the organic purity of the propylene glycol methyl ether acetate is more than or equal to 99.99 percent, the content of single metal impurities is less than or equal to 1ppb, and the content of particles with the particle size of 0.1 mu m is less than or equal to 0.1pcs/ml. The preparation method is simple and convenient, has high conversion rate and yield, short preparation time, few byproducts, simple post-treatment and less pollution to the environment, and is suitable for industrial mass production.
Description
Technical Field
The application belongs to the technical field of chemistry, and particularly relates to a preparation method of propylene glycol methyl ether acetate.
Background
As integrated circuit sizes continue to decrease, the resolution requirements for photoresist during photolithography continue to increase. Therefore, the intensive research on photoresist materials mainly comprising short-wavelength light sources such as KrF, arF or F2 excimer laser is promoted, and photoresist materials with smaller line width, higher resolution and smaller line roughness are continuously developed. Propylene glycol methyl ether acetate is an important raw material for photoresists and is widely used in photoresists. In the prior art, the preparation method of propylene glycol methyl ether acetate has various preparation ways, most of the preparation methods have harsh reaction conditions, the conversion rate and the yield are low, the reaction time is long, byproducts are many, the post-treatment is complex and complicated, the pollution to the environment is large, and the method is not suitable for industrial mass production.
Disclosure of Invention
The embodiment of the application provides a preparation method of propylene glycol methyl ether acetate, which aims to solve the problems of harsh reaction conditions, low conversion rate and yield, long reaction time, more byproducts, complex and complicated post-treatment, larger environmental pollution and unsuitability for industrial mass production in the existing preparation method.
The embodiment of the application is realized in such a way that the preparation method of propylene glycol methyl ether acetate comprises the following steps:
(1) Placing industrial grade propylene glycol methyl ether acetate into a distillation tower for rectification, controlling the temperature of the top of the tower to 145-147 ℃ and the reflux ratio to be 1: (2-3) and condensing water at 1-5 ℃ to obtain fractions; the organic purity of the fraction is more than or equal to 99.99 percent, and the content of single metal impurities of the fraction is less than or equal to 1ppb;
(2) Placing the fraction obtained in the step (1) in a middle tank, connecting the middle tank to a filtering system through a connecting pipeline, and filtering the fraction through the filtering system to obtain propylene glycol methyl ether acetate; the organic purity of the propylene glycol methyl ether acetate is more than or equal to 99.99 percent, the content of single metal impurities is less than or equal to 1ppb, and the content of particles with the particle size of 0.1 mu m is less than or equal to 0.1pcs/ml.
Further, in the step (2),
the filtration system is preferably a filtration system in which multiple filtration systems are connected in series. The fraction was filtered through a multistage system to reduce the 0.1 μm particle size to below 0.1pcs/ml.
The material of the intermediate tank is preferably one of pp material, pe material, pdf material, ptfe material, pfa material, borosilicate glass material, quartz material or 316L stainless steel material.
The material of the connecting pipe is preferably one of pp material, pe material, pdf material, ptfe material or 316L stainless steel material.
The filter of the filter system is preferably made of one of pp material, pe material, pdf material, ptfe material or 316L stainless steel material.
The pore size combination of the filter system is preferably 10 microns+1 microns+30 nanometers, 10 microns+5 microns+30 nanometers, 5 microns+1 microns+30 nanometers or 1 micron+30 nanometers+10 nanometers.
Further, the preparation method of the propylene glycol methyl ether acetate further comprises the following step (3): placing the propylene glycol methyl ether acetate obtained in the step (2) into a metal impurity filter for filtering to obtain propylene glycol methyl ether acetate for filtering metal impurities; the flow rate of the filtration is 3-10L/min; in the propylene glycol methyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10ppt.
The monometal impurity of the propylene glycol methyl ether acetate obtained after the treatment in the step (2) is controlled below 1ppb, so that the filtering width and the filtering depth of the metal impurity can be effectively ensured. By controlling the flow rate of metal impurity filtration to be 3-10L/min, the metal impurity filter can be effectively protected and the maximum filtration effect can be ensured.
The material of the metal impurity filter is preferably one of pp material, pe material, pdf material, ptfe material, or 316L stainless steel material.
The metal impurity filter is preferably one of an adsorption filter, an ion exchange power device, or a chemical reaction filter.
The high-purity propylene glycol methyl ether acetate can be obtained through high-temperature rectification, particle filtration, metal impurity filtration and other treatments, the organic purity of the propylene glycol methyl ether acetate is more than or equal to 99.99 percent, the content of single metal impurities is less than or equal to 10ppt, and the content of 0.1 mu m particles is less than or equal to 0.1pcs/ml. The preparation method is simple and convenient, has high conversion rate and yield, short preparation time, few byproducts, simple post-treatment and less pollution to the environment, and is suitable for industrial mass production.
Detailed Description
The present application will be described in further detail with reference to the following examples in order to make the objects, technical solutions and advantages of the present application more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the application.
In the prior art, the preparation method of propylene glycol methyl ether acetate has various preparation ways, most of the preparation methods have harsh reaction conditions, the conversion rate and the yield are low, the reaction time is long, byproducts are many, the post-treatment is complex and complicated, the pollution to the environment is large, and the method is not suitable for industrial mass production. Based on the above, the embodiment of the application provides a preparation method of propylene glycol methyl ether acetate to solve the above technical problems.
The preparation method of propylene glycol methyl ether acetate can obtain the propylene glycol methyl ether acetate with single metal impurity below 10ppt,0.1 mu m particle below 0.1pcs/ml and organic purity above 99.99 percent.
Specifically, the embodiment of the application is realized in such a way that the preparation method of propylene glycol methyl ether acetate comprises the following steps:
(1) Placing industrial grade propylene glycol methyl ether acetate into a distillation tower for rectification, controlling the temperature of the top of the tower to 145-147 ℃ and the reflux ratio to be 1: (2-3) and condensing water at 1-5 ℃ to obtain fractions; the organic purity of the fraction is more than or equal to 99.99 percent, and the content of single metal impurities of the fraction is less than or equal to 1ppb;
(2) Placing the fraction obtained in the step (1) in a middle tank, connecting the middle tank to a filtering system through a connecting pipeline, and filtering the fraction through the filtering system to obtain propylene glycol methyl ether acetate; the organic purity of the propylene glycol methyl ether acetate is more than or equal to 99.99 percent, the content of single metal impurities is less than or equal to 1ppb, and the content of particles with the particle size of 0.1 mu m is less than or equal to 0.1pcs/ml.
Further, in the step (2),
the filtration system is preferably a filtration system in which multiple filtration systems are connected in series. The fraction was filtered through a multistage system to reduce the 0.1 μm particle size to below 0.1pcs/ml.
The material of the intermediate tank is preferably one of pp material, pe material, pdf material, ptfe material, pfa material, borosilicate glass material, quartz material or 316L stainless steel material.
The material of the connecting pipe is preferably one of pp material, pe material, pdf material, ptfe material or 316L stainless steel material.
The filter of the filter system is preferably made of one of pp material, pe material, pdf material, ptfe material or 316L stainless steel material.
The pore size combination of the filter system is preferably 10 microns+1 microns+30 nanometers, 10 microns+5 microns+30 nanometers, 5 microns+1 microns+30 nanometers or 1 micron+30 nanometers+10 nanometers.
Further, the preparation method of the propylene glycol methyl ether acetate further comprises the following step (3): placing the propylene glycol methyl ether acetate obtained in the step (2) into a metal impurity filter for filtering to obtain propylene glycol methyl ether acetate for filtering metal impurities; the flow rate of the filtration is 3-10L/min; in the propylene glycol methyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10ppt.
The monometal impurity of the propylene glycol methyl ether acetate obtained after the treatment in the step (2) is controlled below 1ppb, so that the filtering width and the filtering depth of the metal impurity can be effectively ensured. By controlling the flow rate of metal impurity filtration to be 3-10L/min, the metal impurity filter can be effectively protected and the maximum filtration effect can be ensured.
The material of the metal impurity filter is preferably one of pp material, pe material, pdf material, ptfe material, or 316L stainless steel material.
The metal impurity filter is preferably one of an adsorption filter, an ion exchange power device, or a chemical reaction filter.
In the present application, 0.1 μm particles means particles having a particle diameter of 0.1 μm or more.
The high-purity propylene glycol methyl ether acetate can be obtained through high-temperature rectification, particle filtration, metal impurity filtration and other treatments, the organic purity of the propylene glycol methyl ether acetate is more than or equal to 99.99 percent, the content of single metal impurities is less than or equal to 10ppt, and the content of 0.1 mu m particles is less than or equal to 0.1pcs/ml. The preparation method is simple and convenient, has high conversion rate and yield, short preparation time, few byproducts, simple post-treatment and less pollution to the environment, and is suitable for industrial mass production.
Example 1
The preparation method of propylene glycol methyl ether acetate provided by the embodiment of the application comprises the following steps:
(1) Placing industrial grade propylene glycol methyl ether acetate into a distillation tower for rectification, controlling the temperature at 145 ℃ at the top of the tower, and controlling the reflux ratio to be 1:2, obtaining a fraction when the temperature of the condensed water is 1 ℃; the organic purity of the fraction is more than or equal to 99.99 percent, and the content of single metal impurities of the fraction is less than or equal to 1ppb;
(2) Placing the fraction obtained in the step (1) in a middle tank, connecting the middle tank to a filtering system through a connecting pipeline, and filtering the fraction through the filtering system to obtain propylene glycol methyl ether acetate; the organic purity of the propylene glycol methyl ether acetate is more than or equal to 99.99 percent, the content of single metal impurities is less than or equal to 1ppb, and the content of particles with the particle size of 0.1 mu m is less than or equal to 0.1pcs/ml.
(3) Placing the propylene glycol methyl ether acetate obtained in the step (2) into a metal impurity filter for filtering to obtain propylene glycol methyl ether acetate for filtering metal impurities; the flow rate of the filtration is 3L/min; in the propylene glycol methyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10ppt.
Further, in the step (2),
the filter system is a filter system with multiple stages of filter systems connected in series. The material of the intermediate tank is pp material. The connecting pipeline is made of pp material. The filter of the filtering system is made of pp material. The pore size combination mode of the filter system is 10 micrometers+1 micrometers+30 nanometers.
Further, in the step (3),
the material of the metal impurity filter is pp material. The metal impurity filter is an adsorption filter.
Table 1 test results of propylene glycol methyl ether acetate prepared in example one
Example two
The preparation method of propylene glycol methyl ether acetate provided by the embodiment of the application comprises the following steps:
(1) Rectifying industrial grade propylene glycol methyl ether acetate in a distillation tower, wherein the temperature of the tower top is controlled to be 146 ℃, the reflux ratio is 1:3, and the condensed water temperature is 3 ℃ to obtain fractions; the organic purity of the fraction is more than or equal to 99.99 percent, and the content of single metal impurities of the fraction is less than or equal to 1ppb;
(2) Placing the fraction obtained in the step (1) in a middle tank, connecting the middle tank to a filtering system through a connecting pipeline, and filtering the fraction through the filtering system to obtain propylene glycol methyl ether acetate; the organic purity of the propylene glycol methyl ether acetate is more than or equal to 99.99 percent, the content of single metal impurities is less than or equal to 1ppb, and the content of particles with the particle size of 0.1 mu m is less than or equal to 0.1pcs/ml.
(3) Placing the propylene glycol methyl ether acetate obtained in the step (2) into a metal impurity filter for filtering to obtain propylene glycol methyl ether acetate for filtering metal impurities; the flow rate of the filtration is 6L/min; in the propylene glycol methyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10ppt.
Further, in the step (2),
the filter system is a filter system with multiple stages of filter systems connected in series. The material of intermediate tank is pe material. The connecting pipeline is made of pvdf material.
The material of the filter of the filtering system is pe material. The pore size combination mode of the filter system is 10 micrometers+5 micrometers+30 nanometers.
Further, in the step (3),
the metal impurity filter is made of pvdf material.
The metal impurity filter is an ion exchange power device.
Table 2 test results of propylene glycol methyl ether acetate prepared in example two
| Parameters (parameters) | Unit (B) | Results |
| Measurement | wt％ | ≤99.99 |
| Metallic impurity (Li) | ppt | ≤10 |
| Metallic impurity (Na) | ppt | ≤10 |
| Metallic impurity (K) | ppt | ≤10 |
| Metal impurity (Mg) | ppt | ≤10 |
| Metallic impurity (Ca) | ppt | ≤10 |
| Metallic impurity (Fe) | ppt | ≤10 |
| Metallic impurity (Cu) | ppt | ≤10 |
| Metallic impurity (Mn) | ppt | ≤10 |
| Metallic impurity (Cr) | ppt | ≤10 |
| Metallic impurity (Ni) | ppt | ≤10 |
| Metal impurity (AL) | ppt | ≤10 |
| Metallic impurity (Ag) | ppt | ≤10 |
| Metallic impurity (Co) | ppt | ≤10 |
| Metallic impurity (Pb) | ppt | ≤10 |
| Metallic impurity (Zn) | ppt | ≤10 |
| Metallic impurity (Sn) | ppt | ≤10 |
| Particles (not less than 0.1 um) | pcs/ml | ≤0.1 |
Example III
The preparation method of propylene glycol methyl ether acetate provided by the embodiment of the application comprises the following steps:
(1) Rectifying industrial propylene glycol methyl ether acetate in a distillation tower with the tower top temperature of 147 ℃, the reflux ratio of 1:2.5 and the condensed water temperature of 5 ℃ to obtain fractions; the organic purity of the fraction is more than or equal to 99.99 percent, and the content of single metal impurities of the fraction is less than or equal to 1ppb;
(2) Placing the fraction obtained in the step (1) in a middle tank, connecting the middle tank to a filtering system through a connecting pipeline, and filtering the fraction through the filtering system to obtain propylene glycol methyl ether acetate; the organic purity of the propylene glycol methyl ether acetate is more than or equal to 99.99 percent, the content of single metal impurities is less than or equal to 1ppb, and the content of particles with the particle size of 0.1 mu m is less than or equal to 0.1pcs/ml.
(3) Placing the propylene glycol methyl ether acetate obtained in the step (2) into a metal impurity filter for filtering to obtain propylene glycol methyl ether acetate for filtering metal impurities; the flow rate of the filtration is 10L/min; in the propylene glycol methyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10ppt.
Further, in step (2), the filtration system is preferably a filtration system in which a plurality of filtration systems are connected in series. The material of the intermediate tank is pfa high borosilicate glass material. The connecting pipeline is made of 316L stainless steel. The filter of the filtering system is made of ptfe material. The pore size combination mode of the filter system is 5 micrometers+1 micrometers+30 nanometers.
Further, in the step (3), the metal impurity filter is made of pvdf. The metal impurity filter is a chemical reaction filter.
TABLE 3 detection results of propylene glycol methyl ether acetate prepared in example III
| Parameters (parameters) | Unit (B) | Results |
| Measurement | wt％ | ≤99.99 |
| Metallic impurity (Li) | ppt | ≤10 |
| Metallic impurity (Na) | ppt | ≤10 |
| Metallic impurity (K) | ppt | ≤10 |
| Metal impurity (Mg) | ppt | ≤10 |
| Metallic impurity (Ca) | ppt | ≤10 |
| Metallic impurity (Fe) | ppt | ≤10 |
| Metallic impurity (Cu) | ppt | ≤10 |
| Metallic impurity (Mn) | ppt | ≤10 |
| Metallic impurity (Cr) | ppt | ≤10 |
| Metallic impurity (Ni) | ppt | ≤10 |
| Metal impurity (AL) | ppt | ≤10 |
| Metallic impurity (Ag) | ppt | ≤10 |
| Metallic impurity (Co) | ppt | ≤10 |
| Metallic impurity (Pb) | ppt | ≤10 |
| Metallic impurity (Zn) | ppt | ≤10 |
| Metallic impurity (Sn) | ppt | ≤10 |
| Particles (not less than 0.1 um) | pcs/ml | ≤0.1 |
Example IV
The preparation method of propylene glycol methyl ether acetate provided by the embodiment of the application comprises the following steps:
(1) Placing industrial grade propylene glycol methyl ether acetate into a distillation tower for rectification, controlling the temperature at the top of the tower to be 147 ℃ and the reflux ratio to be 1:2.3, obtaining a fraction when the temperature of condensed water is 4 ℃; the organic purity of the fraction is more than or equal to 99.99 percent, and the content of single metal impurities of the fraction is less than or equal to 1ppb;
(2) Placing the fraction obtained in the step (1) in a middle tank, connecting the middle tank to a filtering system through a connecting pipeline, and filtering the fraction through the filtering system to obtain propylene glycol methyl ether acetate; the organic purity of the propylene glycol methyl ether acetate is more than or equal to 99.99 percent, the content of single metal impurities is less than or equal to 1ppb, and the content of particles with the particle size of 0.1 mu m is less than or equal to 0.1pcs/ml.
(3) Placing the propylene glycol methyl ether acetate obtained in the step (2) into a metal impurity filter for filtering to obtain propylene glycol methyl ether acetate for filtering metal impurities; the flow rate of the filtration is 8L/min; in the propylene glycol methyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10ppt.
Further, in the step (2),
the filter system is a filter system with multiple stages of filter systems connected in series. The material of the middle tank is ptfe material.
The connecting pipeline is made of pvdf material.
The filter of the filtering system is made of ptfe material.
The pore size combination mode of the filter system is 1 micrometer+30 nanometers+10 nanometers.
Further, in the step (3),
the metal impurity filter is made of 316L stainless steel.
The metal impurity filter is an adsorption filter.
Table 4 test results of propylene glycol methyl ether acetate prepared in example IV
The foregoing description of the preferred embodiments of the application is not intended to be limiting, but rather is intended to cover all modifications, equivalents, and alternatives falling within the spirit and principles of the application.
Claims (6)
1. The preparation method of propylene glycol methyl ether acetate is characterized by comprising the following steps:
(1) Placing industrial grade propylene glycol methyl ether acetate into a distillation tower for rectification, controlling the temperature of the top of the tower to 145-147 ℃ and the reflux ratio to be 1: (2-3) and condensing water at 1-5 ℃ to obtain fractions; the organic purity of the fraction is more than or equal to 99.99 percent, and the content of single metal impurities of the fraction is less than or equal to 1ppb;
(2) Placing the fraction obtained in the step (1) in a middle tank, connecting the middle tank to a filtering system through a connecting pipeline, and filtering the fraction through the filtering system to obtain propylene glycol methyl ether acetate; the organic purity of the propylene glycol methyl ether acetate is more than or equal to 99.99 percent, the content of single metal impurities is less than or equal to 1ppb, and the content of particles with the particle size of 0.1 mu m is less than or equal to 0.1pcs/ml;
in the step (2), the filtering system is a filtering system with a plurality of filtering systems connected in series;
in the step (2), the pore size combination mode of the filter of the filtering system is 10 micrometers+1 micrometers+30 nanometers, 10 micrometers+5 micrometers+30 nanometers, 5 micrometers+1 micrometers+30 nanometers or 1 micrometer+30 nanometers+10 nanometers;
the preparation method of the propylene glycol methyl ether acetate also comprises the following step (3): placing the propylene glycol methyl ether acetate obtained in the step (2) into a metal impurity filter for filtering to obtain propylene glycol methyl ether acetate for filtering metal impurities; the flow rate of the filtration is 3-10L/min; in the propylene glycol methyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10ppt.
2. The method according to claim 1, wherein in the step (2), the material of the intermediate tank is one of pp material, pe material, pdf material, ptfe material, pfa material, borosilicate glass material, quartz material, and 316L stainless steel material.
3. The method according to claim 1, wherein in the step (2), the connecting pipe is made of one of pp material, pe material, pvdf material, ptfe material and 316L stainless steel material.
4. The method according to claim 1, wherein in the step (2), the filter of the filtering system is made of one of pp material, pe material, pdf material, pt fe material, or 316L stainless steel material.
5. The method for producing propylene glycol methyl ether acetate according to claim 1, wherein the metal impurity filter is made of one of pp material, pe material, pvdf material, ptfe material and 316L stainless steel material.
6. The method for producing propylene glycol methyl ether acetate according to claim 1, wherein the metal impurity filter is one of an adsorption filter, an ion exchange filter, and a chemical reaction filter.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107098810A (en) * | 2017-05-16 | 2017-08-29 | 天津大学 | A kind of process for separation and purification for preparing electronic grade propylene glycol methyl ether acetate |
| CN108727191A (en) * | 2017-04-20 | 2018-11-02 | 江苏华伦化工有限公司 | A kind of preparation method of semiconductor grade propylene glycol methyl ether acetate |
| CN109180425A (en) * | 2018-10-29 | 2019-01-11 | 江阴市大洋固废处置利用有限公司 | Process for refining and system containing cyclopentanone and propylene glycol methyl ether acetate recovered liquid |
| CN110204442A (en) * | 2019-05-23 | 2019-09-06 | 安徽京控环境技术服务有限公司 | A method of purification propylene glycol methyl ether acetate is recycled from spent organic solvent |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108727191A (en) * | 2017-04-20 | 2018-11-02 | 江苏华伦化工有限公司 | A kind of preparation method of semiconductor grade propylene glycol methyl ether acetate |
| CN107098810A (en) * | 2017-05-16 | 2017-08-29 | 天津大学 | A kind of process for separation and purification for preparing electronic grade propylene glycol methyl ether acetate |
| CN109180425A (en) * | 2018-10-29 | 2019-01-11 | 江阴市大洋固废处置利用有限公司 | Process for refining and system containing cyclopentanone and propylene glycol methyl ether acetate recovered liquid |
| CN110204442A (en) * | 2019-05-23 | 2019-09-06 | 安徽京控环境技术服务有限公司 | A method of purification propylene glycol methyl ether acetate is recycled from spent organic solvent |
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