CN111467874A - Method for filtering medical liquid containing carboxylic acid derivative - Google Patents
Method for filtering medical liquid containing carboxylic acid derivative Download PDFInfo
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- CN111467874A CN111467874A CN202010074773.XA CN202010074773A CN111467874A CN 111467874 A CN111467874 A CN 111467874A CN 202010074773 A CN202010074773 A CN 202010074773A CN 111467874 A CN111467874 A CN 111467874A
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- carboxylic acid
- acid derivative
- substrate
- group
- filtering
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D37/00—Processes of filtration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D27/00—Cartridge filters of the throw-away type
- B01D27/04—Cartridge filters of the throw-away type with cartridges made of a piece of unitary material, e.g. filter paper
- B01D27/06—Cartridge filters of the throw-away type with cartridges made of a piece of unitary material, e.g. filter paper with corrugated, folded or wound material
- B01D27/07—Cartridge filters of the throw-away type with cartridges made of a piece of unitary material, e.g. filter paper with corrugated, folded or wound material having a coaxial stream through the filtering element
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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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Filtering Materials (AREA)
Abstract
The invention provides a method for filtering a chemical liquid containing a carboxylic acid derivative, which can inhibit hydrolysis of the carboxylic acid derivative, and is a method for filtering a chemical liquid containing a carboxylic acid derivative by using a filter substrate, wherein the filter substrate (1) is formed by alternately arranging a substrate (3) composed of a polyolefin member to which a cation exchange group is chemically bonded and a substrate (4) composed of a polyolefin member to which a strong anion exchange group is chemically bonded, and the chemical liquid is allowed to pass through the filter substrate (1).
Description
Technical Field
The present invention relates to a method for filtering a chemical liquid containing a carboxylic acid derivative.
Background
In recent years, with the progress of semiconductor manufacturing technology in the electronics industry, the design size of the wiring pitch of integrated circuits has become as small as ten nm. With the miniaturization of integrated circuits, the operating speed tends to increase and power consumption tends to decrease. In the process of manufacturing an integrated circuit, metal impurities contained in a chemical solution cause a short circuit of wiring, a decrease in current value, and a decrease in yield, and therefore, it is necessary to increase the purity of the chemical solution. As a means for removing such metal impurities, distillation or ion exchange resins are used, but there are problems that the cost is high in the case of distillation and the processing speed is slow and contamination is caused by the eluted substances in the case of ion exchange resins. A depth type cartridge filter for adsorbing and removing metals in a solution has been known. Patent documents 1 to 3 propose that a polyolefin nonwoven fabric having a strongly acidic cation group such as a sulfonic acid group grafted as a cation exchange group and a polyolefin nonwoven fabric having a quaternary ammonium group grafted as an anion exchange group are used as filter fabrics.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open No. 2014-071004
Patent document 2: japanese patent laid-open publication No. 2009-090259
Patent document 3: japanese laid-open patent publication No. 4-284853
Disclosure of Invention
Technical problem to be solved by the invention
However, the present inventors have found that the conventional filter has a problem that the carboxylic acid derivative is hydrolyzed when the metal ions are removed.
The present invention has been made to solve the problems found by the present inventors, and an object of the present invention is to provide a method for filtering a chemical liquid containing a carboxylic acid derivative, which can suppress hydrolysis of the carboxylic acid derivative.
Means for solving the problems
The method for filtering a chemical liquid containing a carboxylic acid derivative is characterized in that a chemical liquid containing a carboxylic acid derivative is filtered using a filter substrate in which a substrate composed of a polyolefin member to which a cation exchange group is chemically bonded and a substrate composed of a polyolefin member to which a strong anion exchange group is chemically bonded are alternately arranged, and the chemical liquid is passed through the filter substrate.
Effects of the invention
According to the present invention, hydrolysis of a carboxylic acid derivative can be suppressed by using a filter substrate in which a substrate composed of a polyolefin member to which a cation exchange group is chemically bonded and a substrate composed of a polyolefin member to which a strong anion exchange group is chemically bonded are alternately arranged, and passing the chemical solution through the filter substrate.
Drawings
Fig. 1 is a schematic, partially cut-away view of a filter cartridge (filter cartridge) in a depth type cartridge filter according to an embodiment of the present invention.
Fig. 2 is a schematic explanatory view of a treatment apparatus incorporating a depth type cartridge filter according to an embodiment of the present invention.
Fig. 3 is a schematic explanatory view of a liquid passage test apparatus according to an embodiment of the present invention.
FIG. 4 is a schematic explanatory view of the liquid passage test apparatus of example 1.
FIG. 5 is a schematic explanatory view of the liquid passing test apparatus of comparative example 1.
FIG. 6 is a schematic explanatory view of the liquid passing test apparatus of comparative example 2.
FIG. 7 is a graph showing the results of the liquid passing test in examples of the present invention and comparative examples.
Description of the symbols
1, 10 depth type cylinder filter
2 hollow inner cylinder (hollow tube with hole)
3, 17a.. 17j is bonded with the nonwoven fabric layer of cation exchange group
4, 18a
5-depth type cylinder filter
6 container of filter
7 supply port
8 taking-out opening
9a, 9b end cap
11 liquid passing test device
12, 20 container
13 liquid to be treated
14a, 14b fluororesin (PFA) tube
15 nitrogen cylinder
16 column
19, 22, 23 laminated filter
21 treating liquid
Detailed Description
The present invention relates to a method for filtering a chemical liquid containing a carboxylic acid derivative using a filter substrate. The filter substrate is formed by alternately arranging a substrate composed of polyolefin members to which cation exchange groups are chemically bonded and a substrate composed of polyolefin members to which strong anion exchange groups are chemically bonded. Here, the alternating arrangement means that the number of the various base materials may be different. For example, the various substrates may be alternately arranged every 1 layer, or the same substrates may be partially arranged side by side with each other. In addition, the concentration of the functional groups bonded to the various substrates may also be different.
As the filter substrate, for example, a filter cartridge in which a substrate composed of a polyolefin member to which a cation exchange group is chemically bonded and a substrate composed of a polyolefin member to which a strong anion exchange group is chemically bonded are alternately laminated or alternately laminated and wound around a hollow inner tube can be used. The chemical solution is passed through a filter substrate to remove metal ions and recover the carboxylic acid derivative. In this case, hydrolysis of the carboxylic acid derivative is suppressed, and the carboxylic acid derivative is efficiently recovered.
The carboxylic acid derivative is preferably at least one compound selected from the group consisting of an ester bond-containing compound, an amide bond-containing compound, an acid anhydride and a nitrile. These carboxylic acid derivatives are neither resistant to acids (H)+) Nor alkali (OH)-) And is easy to hydrolyze. When in useWhen the chemical solution is passed through a filter substrate (individual layer) composed of a polyolefin member to which a cation exchange group is chemically bonded or a filter substrate (individual layer) composed of a polyolefin member to which a strong anion exchange group is chemically bonded, the carboxylic acid derivative is easily hydrolyzed, but when a filter substrate in which a substrate composed of a polyolefin member to which a cation exchange group is chemically bonded and a substrate composed of a polyolefin member to which a strong anion exchange group is chemically bonded are alternately arranged is used, this problem can be improved.
As the carboxylic acid derivative, specifically, the following are mentioned.
(1) Compounds containing ester linkages
Ethyl lactate, ethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (PGMEA)
(2) Compound containing amido bond
N, N-Dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP)
(3) Acid anhydride compound
Acetic anhydride
(4) Nitrile compound
Acetonitrile
The strong anion exchange group includes a quaternary ammonium group, a pyridyl group, and the like, and a trimethyl amine group is preferably one of the quaternary ammonium groups. This is because metal ion adsorption is high.
The cation exchange group includes a sulfonic acid group, a carboxylic acid group, a phosphoric acid group, and the like, and a sulfonic acid group is preferable. This is because metal ion adsorption is high.
The number of layers of the substrate constituting the filter substrate is preferably 10 or more in total, more preferably 15 or more in total, and still more preferably 20 or more in total.
The most downstream layer of the filter substrate is preferably a substrate composed of a polyolefin member to which cation exchange groups are chemically bonded.
In the invention, the cation exchange groups mainly adsorb Na, Cu and K, and the strong anion exchange groups mainly adsorb Cr, Al and Fe. Therefore, in order to recover a carboxylic acid derivative from a chemical solution containing the carboxylic acid derivative and a metal ion, it is necessary to use a substrate to which a cation exchange group is chemically bonded and a substrate to which a strong anion exchange group is chemically bonded in combination.
The substrate is preferably a base fabric made of a nonwoven fabric, and more preferably a long fiber nonwoven fabric of polyolefin. This is because the long fiber nonwoven fabric is less likely to generate fiber chips and has high filter performance. Wherein the mass per unit area (basis weight) is preferably 10 to 100g/m2The melt-blown long fiber nonwoven fabric of (1). The average diameter of the fibers constituting the long fiber nonwoven fabric is preferably 0.2 to 10 μm. When the above range is used, the filter performance is high. Further, the surface area (specific surface area) can be increased, and the surface of the base material for graft polymerization reaction also increases, so that the graft ratio can be increased. The graft ratio is, for example, preferably 30 to 70%, more preferably 40 to 60%. The reason for this is that if the graft ratio is increased, the base material becomes brittle.
The polyolefin member is preferably one selected from the group consisting of polypropylene, a copolymer of propylene and ethylene, polyethylene, and a copolymer of ethylene and another α -olefin having 4 or more carbon atoms, and particularly preferably high-density polyethylene.
The polyolefin member is irradiated with radiation such as electron beam or gamma ray, and then is brought into contact with an emulsion containing a reactive monomer such as Glycidyl Methacrylate (GMA) or the polyolefin member is brought into contact with an emulsion containing a reactive monomer, and then is irradiated with radiation such as electron beam or gamma ray to graft-polymerize the reactive monomer onto the polyolefin member.
As the graft polymerization method, specifically, for example, there is a liquid phase graft polymerization method in which a nonwoven fabric is activated by irradiation with radiation such as γ rays or electron beams, and then immersed in an emulsion containing water, a surfactant, and a reactive monomer to complete graft polymerization of the nonwoven fabric substrate, and then a sulfonic acid group and a trimethyl amine group are introduced into a graft chain formed in the substrate. The introduction is not limited to the liquid phase graft polymerization method, and a gas phase graft polymerization method in which the substrate is brought into contact with the vapor of the monomer to carry out polymerization; an immersion gas phase graft polymerization method in which a substrate is immersed in a monomer solution, then taken out of the monomer solution, and reacted in a gas phase.
The following description will be made with reference to the drawings. In the drawings, the same reference numerals denote the same components. FIG. 1 is a schematic, partial cross-sectional view of a filter cartridge in a depth type cartridge filter according to one embodiment of the present invention. This filter cartridge 1 is used by winding 2 layers of a filter substrate around a hollow inner tube (hollow tube with holes) 2. That is, 2 layers of a substrate (for example, a nonwoven fabric layer to which a strong anion exchange group is bonded) 3 comprising a polyolefin member to which a cation exchange group is chemically bonded and a substrate (for example, a nonwoven fabric layer to which a strong anion exchange group is bonded) 4 comprising a polyolefin member to which a strong anion exchange group is chemically bonded are wound.
Fig. 2 is a schematic explanatory view of a treatment apparatus incorporating a depth type cartridge filter according to an embodiment of the present invention. In the treatment apparatus 5, the end caps 9a and 9b are attached to the depth type cartridge filter 10, and the apparatus is assembled into the container 6 of the filter, and the liquid to be treated (the chemical liquid containing the carboxylic acid derivative and the metal ions) is supplied from the supply port 7, and the liquid to be treated is led from the outside to the inside of the cartridge 10, while the metal ions are removed, and the treatment liquid is taken out from the take-out port 8.
Fig. 3 is a schematic explanatory view of a liquid passage test apparatus according to an embodiment of the present invention. The liquid passage test apparatus 11 sends nitrogen gas from a nitrogen gas cylinder 15 to the container 12 through a fluororesin (PFA) tube 14a, pushes up the liquid to be treated 13 contained in the container 12, and conveys the liquid to the column 16 through a fluororesin (PFA) tube 14 b. Then, the metal ions contained in the liquid to be treated 13 are adsorbed and removed by the laminated filter 19, and the treatment liquid 21 is introduced into the container 20. In the laminated filter 19, a nonwoven fabric layer (a)17a.. 9 j to which cation exchange groups are bonded on the downstream side and a nonwoven fabric layer (B)18a.. 18j to which strong anion exchange groups are bonded on the upstream side are alternately laminated. The liquid passage test apparatus shown in fig. 3 is a column-type laminated filter, and its basic structure is the same as that of a wound filter. Therefore, the test results of the wound filter can be considered to be the same as those of the column-type laminated filter.
Examples
The present invention will be described in detail with reference to examples. Further, the present invention is not limited to the following examples.
(example 1)
1. Manufacturing process of filter
< graft ratio >
The graft ratio was determined from the following equation using the mass of the nonwoven fabric before and after grafting.
The grafting rate (mass%) is 100 × (B-A)/A
(in the formula, A represents the mass of the nonwoven fabric substrate before grafting, and B represents the mass of the nonwoven fabric substrate after grafting.)
< introduction method of sulfonic acid group and trimethyl amino group >
(Electron Beam irradiation step and graft chain introduction step)
Melt-blown nonwoven Fabric (having a Mass of 81 g/m) for a high-Density polyethylene raw Material having an average fiber diameter of 6 μm20.38mm thick) was irradiated with an electron beam at an acceleration voltage of 200kV and an irradiation dose of 50kGy in a nitrogen atmosphere. Subsequently, the irradiated meltblown nonwoven fabric was immersed in a monomer solution in an emulsion state previously prepared and subjected to nitrogen substitution (nitrogen bubbling), and emulsion graft polymerization was performed for 4 hours while maintaining the temperature at 55 ℃.
The monomer solution used was a pure water emulsion solution containing 1.6 mass% of Glycidyl Methacrylate (GMA) and 0.2 mass% of Tween20 (manufactured by Nacalai Tesque corporation) as a surfactant, based on the total weight of the solution.
When the graft ratio was evaluated, the graft ratio of GMA was 50% by mass.
(sulfonic acid group introduction step)
The GMA graft polymerized nonwoven fabric obtained above was immersed in a 10 mass% sodium sulfite solution prepared by dissolving sodium sulfite in a solution containing 15 mass% isopropyl alcohol and 85 mass% pure water, and heated at 80 ℃ for 9 hours to introduce sulfonic acid groups. The nonwoven fabric was taken out, washed with pure water, and dried to obtain a sulfonic acid type nonwoven fabric.
The nonwoven fabric having sulfonic acid groups introduced therein obtained above was immersed in sulfuric acid having a concentration of 1N, and heated at 80 ℃ for 2 hours to open the remaining epoxy groups and replace sodium ions with hydrogen ions. The nonwoven fabric was taken out, washed with pure water, and dried to obtain a sulfonic acid type ion-exchange nonwoven fabric having an ion-exchange capacity of 2 meq/g. The thickness of the nonwoven fabric was 0.82 mm.
(Trimethylamino group-introducing step)
The GMA graft polymerized nonwoven fabric obtained above was immersed in a mixture of a 10 mass% trimethylamine hydrochloride solution prepared by dissolving trimethylamine hydrochloride in pure water and a 1 equivalent sodium hydroxide aqueous solution, and heated at 60 ℃ for 1 hour to introduce a trimethylamine group. The nonwoven fabric was taken out, washed with pure water, dried, washed with a 3.6% hydrochloric acid aqueous solution, and immersed in a 1% sodium hydroxide aqueous solution. The nonwoven fabric was washed with pure water and dried to obtain a trimethylamine type ion-exchange nonwoven fabric having an ion-exchange capacity of 1.5 meq/g. The thickness of the nonwoven fabric was 0.70 mm.
< production of Metal removing Filter >
Sulfonic acid type ion exchange nonwoven fabric + trimethylamine type ion exchange nonwoven fabric
A sulfonic acid type ion-exchange nonwoven fabric and a trimethylamine type ion-exchange nonwoven fabric were cut into pieces having a diameter of 7mm phi, and 10 pieces of each of them were alternately stacked in a column made of PFA (copolymer of tetrafluoroethylene and perfluoroalkyl vinyl ether) having a diameter of 7mm phi, for a total of 20 pieces. The state is shown in fig. 4.
Mass per 1 substrate
Sulfonic acid type ion exchange nonwoven fabric ═ 0.006 (g/sheet)
Trimethylamine type ion-exchange nonwoven fabric ═ 0.006 (g/sheet)
< liquid to be treated used in experiment >
Ethyl lactate: ethyl lactate with a content of 99.0 wt% or more for electronics industry manufactured by SHOWA DENKO
< liquid introduction and sampling >
Ethyl lactate was introduced into the filter at predetermined flow rates (0.07m L/min, 0.3m L/min, 0.9m L/min), and the solution passed through the filter was sampled into a gas chromatography-mass spectrometry (GC-MS) analysis bottle of 2m L, and the ethanol concentration was measured using the following GC-MS analyzer, and the ethanol concentration was the average of the results of 2 experiments, and the results are shown in table 1.
< GC-MS analysis apparatus
Manufactured by Shimadzu corporation, gas chromatography quality analyzer, model number: GCMS-QP2020
Comparative example 1
An experiment was performed in the same manner as in example 1, except that only the sulfonic acid type ion-exchange nonwoven fabric was used for the metal removal filter. The sulfonic acid type ion-exchange nonwoven fabric was cut into pieces having a diameter of 7mm phi, and 10 pieces of the same were stacked in a column made of PFA (copolymer of tetrafluoroethylene and perfluoroalkyl vinyl ether) having a diameter of 7mm phi. The state is shown in fig. 5.
Comparative example 2
An experiment was performed in the same manner as in example 1, except that only a trimethylamine-type ion-exchange nonwoven fabric was used as the metal removing filter. A trimethylamine type ion-exchange nonwoven fabric was cut into a diameter of 7mm phi, and 10 sheets were stacked in a column made of PFA (copolymer of tetrafluoroethylene and perfluoroalkyl vinyl ether) having a diameter of 7mm phi. The state is shown in fig. 6.
(reference example 1)
Neither sulfonic acid type ion exchange nonwoven fabric nor trimethylamine type ion exchange nonwoven fabric was used, and a column not provided with a substrate was used.
The results are summarized in table 1 and fig. 7.
TABLE 1
When a carboxylic acid derivative (for example, ethyl lactate) is recovered from a chemical solution containing the carboxylic acid derivative and metal ions, it is necessary to use a substrate to which a cation exchange group is chemically bonded in combination with a substrate to which trimethylamine having a strong anion exchange group is chemically bonded; from the results of table 1, it was confirmed: when the substrate to which trimethylamine is chemically bonded is used, ethyl lactate is hydrolyzed to have a high ratio of ethanol to lactic acid, but when a filter in which ethyl lactate is laminated with each other is used, the decomposition of ethyl lactate is suppressed.
Industrial applicability of the invention
The method for filtering a chemical liquid containing a carboxylic acid derivative according to the present invention is useful for recovering a carboxylic acid derivative from a chemical liquid containing a carboxylic acid derivative and a metal ion used in semiconductor production or the like. If the carboxylic acid derivative can be recovered efficiently, it can be reused by distillation or the like.
Claims (6)
1. A method for filtering a chemical liquid containing a carboxylic acid derivative, characterized in that the chemical liquid containing a carboxylic acid derivative is filtered using a filter substrate in which a substrate composed of a polyolefin member to which a cation exchange group is chemically bonded and a substrate composed of a polyolefin member to which a strong anion exchange group is chemically bonded are alternately arranged, and the chemical liquid is passed through the filter substrate.
2. The method for filtering a chemical solution containing a carboxylic acid derivative according to claim 1, wherein the base material is a base fabric made of a nonwoven fabric.
3. The method for filtering a chemical liquid containing a carboxylic acid derivative according to claim 1 or 2, wherein the carboxylic acid derivative is at least one compound selected from the group consisting of an ester bond-containing compound, an amide bond-containing compound, an acid anhydride, and a nitrile.
4. The method for filtering a chemical solution containing a carboxylic acid derivative according to claim 1 or 2, wherein the strong anion exchange group is a trimethyl amine group.
5. The method for filtering a chemical solution containing a carboxylic acid derivative according to claim 1 or 2, wherein the cation exchange group is a sulfonic acid group.
6. The method for filtering a chemical liquid containing a carboxylic acid derivative according to claim 1 or 2, wherein the most downstream layer of the filter substrate is a substrate composed of a polyolefin member to which a sulfonic acid group is chemically bonded.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019-010065 | 2019-01-24 | ||
| JP2019010065A JP7229023B2 (en) | 2019-01-24 | 2019-01-24 | Method for Filtration of Chemical Solution Containing Carboxylic Acid Derivative |
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| CN111467874A true CN111467874A (en) | 2020-07-31 |
| CN111467874B CN111467874B (en) | 2023-02-28 |
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| JP (1) | JP7229023B2 (en) |
| CN (1) | CN111467874B (en) |
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| GB847770A (en) * | 1959-01-28 | 1960-09-14 | Du Pont | Improvements in the purification of dimethylformamide |
| GB924572A (en) * | 1959-12-19 | 1963-04-24 | Bayer Ag | A process for purifying n-dialkylated acid amides |
| JPH04284853A (en) * | 1991-03-13 | 1992-10-09 | Japan Atom Energy Res Inst | Ion exchange filtering method and apparatus therefor |
| CN101678252A (en) * | 2003-04-28 | 2010-03-24 | 创新建材 | Preposition filter and method |
| CN101993386A (en) * | 2010-11-03 | 2011-03-30 | 天津大学 | Method for preparing electronic-grade N, N-dimethylformamide by ion exchange resin method |
| CN102001986A (en) * | 2010-12-23 | 2011-04-06 | 上海化学试剂研究所 | Method for improving quality of industrial N-methylpyrrolidone |
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| JPH01228560A (en) * | 1988-03-08 | 1989-09-12 | Hitachi Chem Co Ltd | Manufacture of solution containing decreased impure metallic components |
| US5446125A (en) * | 1991-04-01 | 1995-08-29 | Ocg Microelectronic Materials, Inc. | Method for removing metal impurities from resist components |
| JP2004330056A (en) | 2003-05-07 | 2004-11-25 | Ebara Corp | Filter cartridge for electronic element substrate surface treatment liquid |
| JP2005247770A (en) | 2004-03-05 | 2005-09-15 | Nippon Kayaku Co Ltd | Process for removing trace metal ion |
| JP5096907B2 (en) | 2007-12-25 | 2012-12-12 | オルガノ株式会社 | Ester purification method |
| JP2013061426A (en) | 2011-09-12 | 2013-04-04 | Nomura Micro Sci Co Ltd | Impurity removal method, impurity removal filtration member and impurity removal filtration device, for resin solution for forming photoresist film |
| KR102605799B1 (en) | 2015-10-02 | 2023-11-23 | 미츠비시 가스 가가쿠 가부시키가이샤 | High purity carboxylic acid ester and method for producing the same |
| EP3397386A4 (en) | 2015-12-28 | 2019-08-21 | Dow Global Technologies, LLC | Purification process for hydrolysable organic solvent |
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2019
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB847770A (en) * | 1959-01-28 | 1960-09-14 | Du Pont | Improvements in the purification of dimethylformamide |
| GB924572A (en) * | 1959-12-19 | 1963-04-24 | Bayer Ag | A process for purifying n-dialkylated acid amides |
| JPH04284853A (en) * | 1991-03-13 | 1992-10-09 | Japan Atom Energy Res Inst | Ion exchange filtering method and apparatus therefor |
| CN101678252A (en) * | 2003-04-28 | 2010-03-24 | 创新建材 | Preposition filter and method |
| CN101993386A (en) * | 2010-11-03 | 2011-03-30 | 天津大学 | Method for preparing electronic-grade N, N-dimethylformamide by ion exchange resin method |
| CN102001986A (en) * | 2010-12-23 | 2011-04-06 | 上海化学试剂研究所 | Method for improving quality of industrial N-methylpyrrolidone |
Also Published As
| Publication number | Publication date |
|---|---|
| JP7229023B2 (en) | 2023-02-27 |
| CN111467874B (en) | 2023-02-28 |
| JP2020116524A (en) | 2020-08-06 |
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