CN114262269A - 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 invention is suitable for the technical field of chemistry, and provides a preparation method of propylene glycol monomethyl ether acetate, which comprises the following steps: (1) placing industrial-grade propylene glycol monomethyl ether acetate in a distillation tower for rectification, controlling the temperature at the top of the tower to be 145-147 ℃, and the reflux ratio to be 1: (2-3) and the temperature of the condensed water is 1-5 ℃, so as to obtain a fraction; 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 1 ppb; (2) placing the fraction obtained in the step (1) into 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 propylene glycol monomethyl ether acetate has an organic purity of more than or equal to 99.99 percent, the content of single metal impurities of less than or equal to 1ppb and the content of 0.1 mu m particles of less than or equal to 0.1 pcs/ml. The preparation method is simple and convenient, high in conversion rate and yield, short in preparation time, few in byproducts, simple in post-treatment, less in environmental pollution and suitable for industrial mass production.
Description
Technical Field
The invention belongs to the technical field of chemistry, and particularly relates to a preparation method of propylene glycol methyl ether acetate.
Background
As the size of integrated circuits is becoming smaller, the resolution requirements for photoresists during photolithography are also increasing. This has led to intensive research into photoresist materials based on short wavelength light sources such as KrF, ArF, or F2 excimer lasers, and the development of photoresist materials with smaller line widths, higher resolutions, and smaller line roughness has been continued. Propylene glycol methyl ether acetate is an important raw material of photoresist and is widely used in the photoresist. In the prior art, the preparation methods of propylene glycol monomethyl ether acetate are various, most of the preparation methods are harsh in reaction conditions, low in conversion rate and yield, long in reaction time, numerous in byproducts, complex and tedious in post-treatment, large in environmental pollution and not suitable for industrial mass production.
Disclosure of Invention
The embodiment of the invention provides a preparation method of propylene glycol monomethyl ether acetate, and aims to solve the problems that the existing preparation method is harsh in reaction conditions, low in conversion rate and yield, long in reaction time, large in number of byproducts, complex and tedious in post-treatment, large in environmental pollution and not suitable for industrial mass production.
The embodiment of the invention is realized in such a way that the preparation method of the propylene glycol monomethyl ether acetate comprises the following steps:
(1) placing industrial-grade propylene glycol monomethyl ether acetate in a distillation tower for rectification, controlling the temperature at the top of the tower to be 145-147 ℃, and the reflux ratio to be 1: (2-3) and the temperature of the condensed water is 1-5 ℃, so as to obtain a fraction; 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 1 ppb;
(2) placing the fraction obtained in the step (1) into 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 propylene glycol monomethyl ether acetate has an organic purity of more than or equal to 99.99 percent, the content of single metal impurities of less than or equal to 1ppb and the content of 0.1 mu m particles of less than or equal to 0.1 pcs/ml.
Further, in the step (2),
the filtration system is preferably a filtration system with multiple stages of filtration systems in series. By performing filtration in a multistage system, the fraction with 0.1 μm particles can be reduced to below 0.1 pcs/ml.
The material of the intermediate tank is preferably one of pp material, pe material, pvdf material, ptfe material, pfa material, borosilicate glass material, quartz material or 316L stainless steel material.
The material of the connecting pipeline is preferably one of pp material, pe material, pvdf material, ptfe material or 316L stainless steel material.
The material of the filter of the filtering system is preferably one of pp material, pe material, pvdf material, ptfe material or 316L stainless steel material.
The aperture combination mode of the filter of the filtering system is preferably 10 micrometers +1 micrometer +30 nanometers, 10 micrometers +5 micrometers +30 nanometers, 5 micrometers +1 micrometer +30 nanometers or 1 micrometer +30 nanometers +10 nanometers.
Further, the preparation method of the propylene glycol methyl ether acetate further comprises the step (3): placing the propylene glycol methyl ether acetate obtained in the step (2) in 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 monomethyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10 ppt.
The single metal impurities of the propylene glycol monomethyl ether acetate obtained after the treatment of the step (2) are controlled to be below 1ppb, so that the filtering width and the filtering depth of the metal impurities can be effectively ensured. The flow rate of the metal impurity filter is controlled to be 3-10L/min, so that the metal impurity filter can be effectively protected and the filtering effect can be maximized.
The material of the metal impurity filter is preferably one of pp material, pe material, pvdf material, ptfe material or 316L stainless steel material.
The metallic impurity filter is preferably one of an adsorption filter, an ion exchange power device, or a chemical reaction filter.
The high-purity propylene glycol monomethyl ether acetate can be obtained by high-temperature rectification, particle filtration, metal impurity filtration and other treatments, the organic purity is more than or equal to 99.99 percent, the content of single metal impurity is less than or equal to 10ppt, and the content of 0.1 mu m particles is less than or equal to 0.1 pcs/ml. The preparation method is simple and convenient, high in conversion rate and yield, short in preparation time, few in byproducts, simple in post-treatment, less in environmental pollution and suitable for industrial mass production.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In the prior art, the preparation methods of propylene glycol monomethyl ether acetate are various, most of the preparation methods are harsh in reaction conditions, low in conversion rate and yield, long in reaction time, numerous in byproducts, complex and tedious in post-treatment, large in environmental pollution and not suitable for industrial mass production. Based on this, the embodiment of the invention provides a preparation method of propylene glycol methyl ether acetate to solve the technical problems.
By the preparation method of the propylene glycol monomethyl ether acetate, the high-purity propylene glycol monomethyl ether acetate with single metal impurities below 10ppt, 0.1 mu m particles below 0.1pcs/ml and organic purity above 99.99 percent can be obtained.
Specifically, the embodiment of the invention is realized in such a way that the preparation method of propylene glycol monomethyl ether acetate comprises the following steps:
(1) placing industrial-grade propylene glycol monomethyl ether acetate in a distillation tower for rectification, controlling the temperature at the top of the tower to be 145-147 ℃, and the reflux ratio to be 1: (2-3) and the temperature of the condensed water is 1-5 ℃, so as to obtain a fraction; 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 1 ppb;
(2) placing the fraction obtained in the step (1) into 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 propylene glycol monomethyl ether acetate has an organic purity of more than or equal to 99.99 percent, the content of single metal impurities of less than or equal to 1ppb and the content of 0.1 mu m particles of less than or equal to 0.1 pcs/ml.
Further, in the step (2),
the filtration system is preferably a filtration system with multiple stages of filtration systems in series. By performing filtration in a multistage system, the fraction with 0.1 μm particles can be reduced to below 0.1 pcs/ml.
The material of the intermediate tank is preferably one of pp material, pe material, pvdf material, ptfe material, pfa material, borosilicate glass material, quartz material or 316L stainless steel material.
The material of the connecting pipeline is preferably one of pp material, pe material, pvdf material, ptfe material or 316L stainless steel material.
The material of the filter of the filtering system is preferably one of pp material, pe material, pvdf material, ptfe material or 316L stainless steel material.
The aperture combination mode of the filter of the filtering system is preferably 10 micrometers +1 micrometer +30 nanometers, 10 micrometers +5 micrometers +30 nanometers, 5 micrometers +1 micrometer +30 nanometers or 1 micrometer +30 nanometers +10 nanometers.
Further, the preparation method of the propylene glycol methyl ether acetate further comprises the step (3): placing the propylene glycol methyl ether acetate obtained in the step (2) in 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 monomethyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10 ppt.
The single metal impurities of the propylene glycol monomethyl ether acetate obtained after the treatment of the step (2) are controlled to be below 1ppb, so that the filtering width and the filtering depth of the metal impurities can be effectively ensured. The flow rate of the metal impurity filter is controlled to be 3-10L/min, so that the metal impurity filter can be effectively protected and the filtering effect can be maximized.
The material of the metal impurity filter is preferably one of pp material, pe material, pvdf material, ptfe material or 316L stainless steel material.
The metallic 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 mean particles having a particle diameter of 0.1 μm or more.
The high-purity propylene glycol monomethyl ether acetate can be obtained by high-temperature rectification, particle filtration, metal impurity filtration and other treatments, the organic purity is more than or equal to 99.99 percent, the content of single metal impurity is less than or equal to 10ppt, and the content of 0.1 mu m particles is less than or equal to 0.1 pcs/ml. The preparation method is simple and convenient, high in conversion rate and yield, short in preparation time, few in byproducts, simple in post-treatment, less in environmental pollution and suitable for industrial mass production.
Example one
The preparation method of propylene glycol monomethyl ether acetate provided by the embodiment of the invention comprises the following steps:
(1) placing industrial-grade propylene glycol monomethyl ether acetate in a distillation tower for rectification, controlling the temperature at the top of the tower to be 145 ℃ and the reflux ratio to be 1:2, the temperature of the condensed water is 1 ℃, and a fraction is obtained; 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 1 ppb;
(2) placing the fraction obtained in the step (1) into 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 propylene glycol monomethyl ether acetate has an organic purity of more than or equal to 99.99 percent, the content of single metal impurities of less than or equal to 1ppb and the content of 0.1 mu m particles of less than or equal to 0.1 pcs/ml.
(3) Placing the propylene glycol methyl ether acetate obtained in the step (2) in 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 monomethyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10 ppt.
Further, in the step (2),
the filtering system is formed by connecting a plurality of stages of filtering systems in series. The material of the intermediate tank is pp material. The connecting pipeline is made of pp materials. The filter of the filtering system is made of pp material. The aperture combination mode of the filter of the filtering system is 10 micrometers +1 micrometer +30 nanometers.
Further, in the step (3),
the metal impurity filter is made of pp. 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 monomethyl ether acetate provided by the embodiment of the invention comprises the following steps:
(1) placing industrial-grade propylene glycol monomethyl ether acetate in a distillation tower for rectification, and controlling the tower top temperature to be 146 ℃, the reflux ratio to be 1:3 and the condensate temperature to be 3 ℃ to obtain a fraction; 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 1 ppb;
(2) placing the fraction obtained in the step (1) into 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 propylene glycol monomethyl ether acetate has an organic purity of more than or equal to 99.99 percent, the content of single metal impurities of less than or equal to 1ppb and the content of 0.1 mu m particles of less than or equal to 0.1 pcs/ml.
(3) Placing the propylene glycol methyl ether acetate obtained in the step (2) in 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 monomethyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10 ppt.
Further, in the step (2),
the filtering system is formed by connecting a plurality of stages of filtering systems in series. The material of pans is the pe material. The connecting pipeline is made of a pvdf material.
The material of filtration system's filter is the pe material. The aperture combination mode of the filter of the filtering system is 10 microns, 5 microns and 30 nanometers.
Further, in the step (3),
the material of metal impurity filter is the pvdf material.
The metal impurity filter is an ion exchange power device.
TABLE 2 detection results of propylene glycol monomethyl ether acetate prepared in example two
| Parameter(s) | Unit of | Results |
| Measurement of | wt％ | ≤99.99 |
| Metallic impurity (Li) | ppt | ≤10 |
| Metallic impurity (Na) | ppt | ≤10 |
| Metallic impurity (K) | ppt | ≤10 |
| Metallic 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 |
| Metallic 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 |
| Particle (not less than 0.1um) | pcs/ml | ≤0.1 |
EXAMPLE III
The preparation method of propylene glycol monomethyl ether acetate provided by the embodiment of the invention comprises the following steps:
(1) placing industrial-grade propylene glycol monomethyl ether acetate in a distillation tower for rectification, and controlling the tower top temperature to be 147 ℃, the reflux ratio to be 1:2.5 and the condensate temperature to be 5 ℃ to obtain a fraction; 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 1 ppb;
(2) placing the fraction obtained in the step (1) into 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 propylene glycol monomethyl ether acetate has an organic purity of more than or equal to 99.99 percent, the content of single metal impurities of less than or equal to 1ppb and the content of 0.1 mu m particles of less than or equal to 0.1 pcs/ml.
(3) Placing the propylene glycol methyl ether acetate obtained in the step (2) in 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 monomethyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10 ppt.
Further, in the step (2), the filtering system is preferably a filtering system in which a plurality of filtering systems are connected in series. The material of pans is pfa material borosilicate glass material. The connecting pipeline is made of 316L stainless steel. The material of the filter of the filtering system is ptfe material. The aperture combination mode of the filter of the filtering system is 5 microns +1 micron +30 nanometers.
Further, in the step (3), the material of the metal impurity filter is a pvdf material. The metal impurity filter is a chemical reaction filter.
TABLE 3 detection results of propylene glycol monomethyl ether acetate prepared in example III
| Parameter(s) | Unit of | Results |
| Measurement of | wt％ | ≤99.99 |
| Metallic impurity (Li) | ppt | ≤10 |
| Metallic impurity (Na) | ppt | ≤10 |
| Metallic impurity (K) | ppt | ≤10 |
| Metallic 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 |
| Metallic 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 |
| Particle (not less than 0.1um) | pcs/ml | ≤0.1 |
Example four
The preparation method of propylene glycol monomethyl ether acetate provided by the embodiment of the invention comprises the following steps:
(1) placing industrial-grade propylene glycol monomethyl ether acetate in 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 and the temperature of the condensed water is 4 ℃ to obtain a fraction; 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 1 ppb;
(2) placing the fraction obtained in the step (1) into 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 propylene glycol monomethyl ether acetate has an organic purity of more than or equal to 99.99 percent, the content of single metal impurities of less than or equal to 1ppb and the content of 0.1 mu m particles of less than or equal to 0.1 pcs/ml.
(3) Placing the propylene glycol methyl ether acetate obtained in the step (2) in 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 monomethyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10 ppt.
Further, in the step (2),
the filtering system is formed by connecting a plurality of stages of filtering systems in series. The tundish is made of ptfe.
The connecting pipeline is made of a pvdf material.
The material of the filter of the filtering system is ptfe material.
The aperture combination mode of the filter of the filtering system is 1 micron +30 nm +10 nm.
Further, in the step (3),
the material of the metal impurity filter is 316L stainless steel.
The metal impurity filter is an adsorption filter.
TABLE 4 detection results of propylene glycol monomethyl ether acetate prepared in example IV
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (9)
1. The preparation method of the propylene glycol monomethyl ether acetate is characterized by comprising the following steps:
(1) placing industrial-grade propylene glycol monomethyl ether acetate in a distillation tower for rectification, controlling the temperature at the top of the tower to be 145-147 ℃, and the reflux ratio to be 1: (2-3) and the temperature of the condensed water is 1-5 ℃, so as to obtain a fraction; 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 1 ppb;
(2) placing the fraction obtained in the step (1) into 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 propylene glycol monomethyl ether acetate has an organic purity of more than or equal to 99.99 percent, the content of single metal impurities of less than or equal to 1ppb and the content of 0.1 mu m particles of less than or equal to 0.1 pcs/ml.
2. The method for preparing propylene glycol monomethyl ether acetate according to claim 1, wherein in the step (2), the filtration system is a filtration system in which a plurality of filtration systems are connected in series.
3. The method for preparing propylene glycol methyl ether acetate according to claim 1, wherein in the step (2), the material of the intermediate tank is one of pp material, pe material, pvdf material, ptfe material, pfa material, borosilicate glass material, quartz material or 316L stainless steel material.
4. The method for preparing propylene glycol methyl ether acetate according to claim 1, wherein in the step (2), the connecting pipeline is made of one of pp material, pe material, pvdf material, ptfe material or 316L stainless steel material.
5. The method for preparing propylene glycol methyl ether acetate according to claim 1, wherein in the step (2), the material of the filter of the filtering system is one of pp material, pe material, pvdf material, ptfe material or 316L stainless steel material.
6. The method for preparing propylene glycol methyl ether acetate according to claim 1, wherein in the step (2), the filter of the filtering system has a pore size combination mode of 10 microns +1 micron +30 nm, 10 microns +5 microns +30 nm, 5 microns +1 micron +30 nm, or 1 micron +30 nm +10 nm.
7. The method for preparing propylene glycol methyl ether acetate according to claim 1, wherein the method for preparing propylene glycol methyl ether acetate further comprises the step (3): placing the propylene glycol methyl ether acetate obtained in the step (2) in 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 monomethyl ether acetate for filtering metal impurities, the content of single metal impurities is less than or equal to 10 ppt.
8. The method for preparing propylene glycol monomethyl ether acetate according to claim 7, wherein the metallic impurity filter is made of one of pp material, pe material, pvdf material, ptfe material or 316L stainless steel material.
9. The method for preparing propylene glycol monomethyl ether acetate according to claim 7, wherein the metal impurity filter is one of an adsorption filter, an ion exchange power device, or 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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