US20180273465A1 - High-purity carboxylic acid ester and method for producing same - Google Patents

High-purity carboxylic acid ester and method for producing same Download PDF

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US20180273465A1
US20180273465A1 US15/763,590 US201615763590A US2018273465A1 US 20180273465 A1 US20180273465 A1 US 20180273465A1 US 201615763590 A US201615763590 A US 201615763590A US 2018273465 A1 US2018273465 A1 US 2018273465A1
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carboxylic acid
acid ester
exchange resin
anion
impurities
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Kuniaki Muneyasu
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Mitsubishi Gas Chemical Co Inc
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Mitsubishi Gas Chemical Co Inc
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Assigned to MITSUBISHI GAS CHEMICAL COMPANY, INC. reassignment MITSUBISHI GAS CHEMICAL COMPANY, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MUNEYASU, KUNIAKI
Publication of US20180273465A1 publication Critical patent/US20180273465A1/en
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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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/04—Processes using organic exchangers
    • B01J39/05—Processes using organic exchangers in the strongly acidic form
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/16—Organic material
    • B01J39/18—Macromolecular compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/26—Cation exchangers for chromatographic processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/04—Processes using organic exchangers
    • B01J41/07—Processes using organic exchangers in the weakly basic form
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/12—Macromolecular compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/20—Anion exchangers for chromatographic processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J47/00—Ion-exchange processes in general; Apparatus therefor
    • B01J47/02—Column or bed processes
    • B01J47/026—Column or bed processes using columns or beds of different ion exchange materials in series
    • B01J47/028—Column or bed processes using columns or beds of different ion exchange materials in series with alternately arranged cationic and anionic exchangers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
    • C07C69/68—Lactic acid esters

Definitions

  • the present invention relates to a method for purifying a carboxylic acid ester, wherein the metal impurity content and the anionic impurity content are reduced.
  • the carboxylic acid ester of the present invention is useful for a wide range of applications such as synthetic raw materials, cleaning agents for electronic components and solvents for paints, adhesives and the like. Further, it is used as a treatment agent for cleaning of a semiconductor substrate, etching, development of a photoresist and the like in the production of integrated circuits and large-scale integrated circuits. In particular, in applications for semiconductors, very high purity is required because of contamination of semiconductor substrates, and a high-purity carboxylic acid ester containing impurities in an amount as small as possible is required.
  • carboxylic acid esters conventionally used have high concentrations of metal impurities and anionic impurities, and have problems in which, for example, these cannot be used in applications for semiconductors.
  • Patent Document 1 describes a method for limiting the water content in a carboxylic acid ester as a technique for improving storage stability and corrosiveness against metal materials of the carboxylic acid ester. Further, the document describes a method for limiting the water content to suppress hydrolysis of the carboxylic acid ester, thereby suppressing increase in an acid content (a hydrolyzate of the carboxylic acid ester) which causes corrosion of metal materials, etc., but does not describe reduction in metal impurities.
  • Patent Document 2 describes a method for reducing an acid content in a carboxylic acid ester by means of neutralization or the like to improve storage stability (decomposition, discoloration, etc. during storage). In this method, just decomposition and discoloration of the carboxylic acid ester itself are suppressed, and the document does not describe reduction in metal impurities.
  • Patent Document 3 describes a method for bringing a substantially anhydrous organic solution into contact with one or a plurality of cation-exchange resins for the purpose of reducing the content of alkali metal and alkaline earth metal cations.
  • the type of metal cations to be reduced is limited to alkali metals and alkaline earth metals, and the document does not describe reduction in anionic impurities. Therefore, the method is insufficient as a method for purifying a carboxylic acid ester.
  • Patent Documents 4 and 5 describe a method of purification with a very high purity at the time of removing metal ions and the like contained in a non-aqueous liquid material using an ion exchange resin, wherein the non-aqueous liquid material is brought into contact with a cation-exchange resin alone or a mixed ion exchange resin consisting of a cation-exchange resin and an anion-exchange resin to reduce the concentration of metal impurities in the non-aqueous liquid material to a very low level, and wherein an eluate from the resin itself is also removed.
  • the Na concentration after purification is 50 ppb or less and does not satisfy the concentration of metal impurities required for applications for semiconductors (1 ppb or less), and therefore the method is insufficient as a method for purifying a carboxylic acid ester.
  • Patent Document 6 describes a method of removing metal ions in an organic solvent by using an ion exchange resin having OH or a weak acid as a counter ion of a strongly basic anion-exchange resin.
  • the document describes only Fe and Pd as metal impurities that can be removed, and does not describe removal of impurities including other alkali metals. Therefore, the method is insufficient as a method for purifying a carboxylic acid ester. Thus, there is no known method for highly purifying a carboxylic acid ester.
  • Patent Document 1 Japanese Patent No. 3813199
  • Patent Document 2 Japanese Patent No. 4116104
  • Patent Document 3 Japanese Patent No. 4302201
  • Patent Document 4 Japanese Laid-Open Patent Publication No. 2004-181351
  • Patent Document 5 Japanese Laid-Open Patent Publication No. 2004-181352
  • Patent Document 6 Japanese Laid-Open Patent Publication No. 2005-247770
  • the objective of the present invention is to provide a high-purity carboxylic acid ester, wherein the metal impurity content and the anionic impurity content are significantly reduced.
  • the present inventors diligently made researches on methods for purifying a carboxylic acid ester in order to solve the problems and found that a carboxylic acid ester can be highly purified by using an ion exchange resin at the time of removing metal impurities and anionic impurities from carboxylic acid ester and by defining the order of a cation-exchange resin and anion-exchange resin for flowing through, and thus the present invention was achieved.
  • the present invention is as follows:
  • a high-purity carboxylic acid ester wherein the Ag, Al, Au, Ca, Cr, Cu, Fe, K, Mg, Na, Sn and Zn contents as metal impurity contents are each less than 1 ppb, and wherein the anionic impurity content is less than 1 ppm.
  • a method for producing a high-purity carboxylic acid ester including: a step of bringing a crude carboxylic acid ester that contains anionic impurities and at least Ag, Al, Au, Ca, Cr, Cu, Fe, K, Mg, Na, Sn and Zn as metal impurities into contact with a cation-exchange resin (II); and a step of subsequently bringing the crude carboxylic acid ester into contact with an anion-exchange resin (III).
  • ⁇ 3> The method for producing a high-purity carboxylic acid ester according to item ⁇ 2>, which includes a step of bringing the crude carboxylic acid ester into contact with an anion-exchange resin (I) before bringing the crude carboxylic acid ester into contact with the cation-exchange resin (II).
  • ⁇ 4> The method for producing a high-purity carboxylic acid ester according to item ⁇ 2> or ⁇ 3>, wherein the carboxylic acid ester is at least one selected from the group consisting of methyl lactate, ethyl lactate, propyl lactate, methyl ⁇ -hydroxyisobutyrate, ethyl ⁇ -hydroxyisobutyrate, propyl ⁇ -hydroxyisobutyrate, butyl ⁇ -hydroxyisobutyrate, methyl ⁇ -hydroxyisobutyrate, ethyl ⁇ -hydroxyisobutyrate, propyl ⁇ -hydroxyisobutyrate and butyl ⁇ -hydroxyisobutyrate.
  • ⁇ 5> The method for producing a high-purity carboxylic acid ester according to any one of items ⁇ 2> to ⁇ 4>, wherein in the obtained high-purity carboxylic acid ester, the Ag, Al, Au, Ca, Cr, Cu, Fe, K, Mg, Na, Sn and Zn contents as metal impurity contents are each less than 1 ppb and the anionic impurity content is less than 1 ppm.
  • ⁇ 6> The method for producing a high-purity carboxylic acid ester according to any one of items ⁇ 2> to ⁇ 5>, wherein in the crude carboxylic acid ester, the Ag, Al, Au, Ca, Cr, Cu, Fe, K, Mg, Na, Sn and Zn contents as metal impurity contents are each 8 ppb or more and the anionic impurity content is 20 ppm or more.
  • metal impurities and anionic impurities are highly reduced, and it can be suitably used for many applications in which a carboxylic acid ester is used, in particular, applications in the field of electronics industry. Specifically, it is used for a wide range of applications such as synthetic raw materials, cleaning agents for electronic components and solvents for paints, adhesives and the like, or it is used as a treatment agent for cleaning of a semiconductor substrate, etching, development of a photoresist and the like in the production of integrated circuits and large-scale integrated circuits. Accordingly, the present invention has industrial significance.
  • FIG. 1 is a schematic view showing a process of obtaining a high-purity carboxylic acid ester by flowing a carboxylic acid ester through a weakly basic anion-exchange resin (I), a strongly acidic cation-exchange resin (II) and a weakly basic anion-exchange resin (III) in this order in Examples 1 and 2.
  • a weakly basic anion-exchange resin I
  • a strongly acidic cation-exchange resin II
  • III weakly basic anion-exchange resin
  • the present invention relates to a high-purity carboxylic acid ester in which metal impurity contents are each less than 1 ppb and the anionic impurity content is less than 1 ppm, and a method for producing the same.
  • the high-purity carboxylic acid ester of the present invention is produced by bringing a crude carboxylic acid ester that contains metal impurities and anionic impurities into contact with a cation-exchange resin and an anion-exchange resin to remove the metal impurities with both the cation-exchange resin and the anion-exchange resin and remove the anionic impurities with the anion-exchange resin.
  • the anionic impurities of the present invention include a carboxylic acid, which is contained in the crude carboxylic acid ester and is generated by a hydrolysis reaction of the carboxylic acid ester.
  • the crude carboxylic acid ester of the present invention contains metal impurities and anionic impurities. It may also contain water as one of other components.
  • the metal impurities include at least Ag, Al, Au, Ca, Cr, Cu, Fe, K, Mg, Na, Sn and Zn.
  • the Ag, Al, Au, Ca, Cr, Cu, Fe, K, Mg, Na, Sn and Zn contents as the contents of the metal impurities are each preferably 8 ppb or more.
  • the content of the anionic impurities is preferably 20 ppm or more. According to the present invention, it is possible to produce a high-purity carboxylic acid ester even when using such a crude carboxylic acid ester with a high impurity concentration.
  • cation-exchange resin (II) to be used in the present invention an H-type strongly acidic cation-exchange resin and a Na-type strongly acidic cation-exchange resin are preferred, and among them, an H-type strongly acidic cation-exchange resin having a sulfonic acid group can be particularly suitably used.
  • a commercially-available product can be used, and specific examples thereof include 15JS-HG DRY (manufactured by Organo Corporation).
  • anion-exchange resins (I) and (III) to be used in the present invention include a strongly basic anion-exchange resin and a weakly basic anion-exchange resin, but a weakly basic anion-exchange resin is preferred, and a free base type weakly basic anion-exchange resin is more preferred. Among them, a weakly basic anion-exchange resin having a tertiary ammonium base can be particularly suitably used.
  • anion-exchange resin a commercially-available product can be used, and specific examples thereof include B20-HG DRY (manufactured by Organo Corporation).
  • the anion-exchange resin (I) and the anion-exchange resin (III) may be the same or different.
  • the method for bringing the crude carboxylic acid ester into contact with the cation-exchange resin (II) and anion-exchange resins (I) and (III) is not particularly limited, but a method for flowing the crude carboxylic acid ester through the cation-exchange resin and anion-exchange resins is generally employed.
  • the temperatures of the crude carboxylic acid ester, cation-exchange resin and anion-exchange resins are preferably 100° C. or lower.
  • the production method of the present invention can be carried out by using either a batch method or a flow method, but in view of purification efficiency, the flow method in which the crude carboxylic acid ester is flowed through columns filled with ion exchange resins is preferably employed.
  • the method of delivering a solution may be either upflow or downflow, and the space velocity of flowing through (SV: Hr ⁇ 1 ) is suitably determined depending on the type and viscosity of the solution, pressure loss of resin, etc. but is preferably 1 to 50 Hr ⁇ 1 , and more preferably 10 to 20 Hr ⁇ 1 .
  • the concentration of moisture in the crude carboxylic acid ester is not defined, but when bringing a carboxylic acid ester containing moisture into contact with the cation-exchange resin and flowing it therethrough, an acid content is generated by hydrolysis. When subsequently bringing the carboxylic acid ester containing the increased acid content into contact with the anion-exchange resin and flowing it therethrough, the generated acid content is captured by the anion-exchange resin and shortens the life of the anion-exchange resin. For this reason, the concentration of moisture in the crude carboxylic acid ester is preferably 0.01% by weight or less.
  • a method for producing the high-purity carboxylic acid ester of the present invention a method in which contact with the anion-exchange resin (I) is performed before contact with the cation-exchange resin (II) is more preferred.
  • the hydrolysis reaction between moisture contained in the crude carboxylic acid ester and the carboxylic acid ester is caused to newly generate the anionic impurities.
  • the anionic impurities (the carboxylic acid) contained in the crude carboxylic acid ester are brought into contact with the anion-exchange resin (I) to be captured before contact with the cation-exchange resin (II), thereby reducing the load of the anionic impurities to be subsequently captured by the anion-exchange resin (III). For this reason, the life of the anion-exchange resin (III) can be improved.
  • the present invention will be specifically described by way of working examples and comparative examples. However, the present invention is not limited to the working examples. Note that the concentrations of the metal impurities and anionic impurities in the carboxylic acid ester were analyzed as described below.
  • Quantitative analysis was carried out using an ICP mass spectrometer (Agilent 7900 ICP-MS manufactured by Agilent).
  • Quantitative analysis was carried out using an automatic titrator (automatic titrator AT-510 manufactured by Kyoto Electronics Manufacturing Co., Ltd.) with 0.01 mol/L of sodium hydroxide. Analysis was carried out after 30 mL of methanol was added to 50 mL of carboxylic acid ester.
  • each of an H-type strongly acidic cation-exchange resin (trade name: 15JS-HG DRY, manufactured by Organo Corporation) and a free base type weakly basic anion-exchange resin (trade name: B20-HG DRY, manufactured by Organo Corporation) was put into ethyl lactate separately and immersed therein for 1 hour or longer while being gently stirred suitably.
  • one FEP column having an inner diameter of 16 mm was filled with 10 ml of strongly acidic cation-exchange resin, and each of two FEP columns having an inner diameter of 16 mm was filled with 10 ml of weakly basic anion-exchange resin.
  • each of an H-type strongly acidic cation-exchange resin (trade name: 15JS-HG DRY, manufactured by Organo Corporation) and a free base type weakly basic anion-exchange resin (trade name: B20-HG DRY, manufactured by Organo Corporation) was put into methyl hydroxyisobutyrate separately and immersed therein for 1 hour or longer while being gently stirred suitably.
  • one FEP column having an inner diameter of 16 mm was filled with 10 ml of strongly acidic cation-exchange resin, and each of two FEP columns having an inner diameter of 16 mm was filled with 10 ml of weakly basic anion-exchange resin.
  • the anionic impurity concentrations after flowing through are shown in Table 3. According to Table 3, the anion content was highly removed during time between when flowing through was started and when the amount was 2000 ml, but the anion content was increased after the amount reached 2500 ml.
  • H-type strongly acidic cation-exchange resin (trade name: 15JS-HG DRY, manufactured by Organo Corporation) and a free base type weakly basic anion-exchange resin (trade name: B20-HG DRY, manufactured by Organo Corporation) were pretreated with methyl hydroxyisobutyrate in a manner similar to that in Example 2.
  • one FEP column having an inner diameter of 16 mm was filled with 10 ml of strongly acidic cation-exchange resin, and another FEP column having an inner diameter of 16 mm was filled with 10 ml of weakly basic anion-exchange resin.
  • Example 2 the ability to remove the anion content can be more improved in Example 2 in which methyl hydroxyisobutyrate was flowed through the weakly basic anion-exchange resin (I) before it was flowed through the strongly acidic cation-exchange resin (II), and in addition, the life of the anion-exchange resin (III) can be improved.
  • the carboxylic acid ester is a compound useful for a wide range of applications such as synthetic raw materials, cleaning agents for electronic components and solvents for paints, adhesives and the like, or as a treatment agent for cleaning of a semiconductor substrate, etching, development of a photoresist and the like in the production of integrated circuits and large-scale integrated circuits.

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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WO2023169810A1 (de) 2022-03-11 2023-09-14 Röhm Gmbh Verfahren zur herstellung von alpha-hydroxyisobuttersäuremethylester und dessen anwendung in der elektronik-industrie
US11759774B2 (en) * 2015-12-28 2023-09-19 Dow Global Technologies Llc Purification process for hydrophilic organic solvent

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JP7229023B2 (ja) * 2019-01-24 2023-02-27 倉敷繊維加工株式会社 カルボン酸誘導体を含む薬液を濾過する方法
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Cited By (4)

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EP3397386A4 (en) * 2015-12-28 2019-08-21 Dow Global Technologies, LLC PROCESS FOR PURIFYING HYDROLYSABLE ORGANIC SOLVENT
US10913058B2 (en) 2015-12-28 2021-02-09 Dow Global Technologies Llc Purification process for hydrolysable organic solvent
US11759774B2 (en) * 2015-12-28 2023-09-19 Dow Global Technologies Llc Purification process for hydrophilic organic solvent
WO2023169810A1 (de) 2022-03-11 2023-09-14 Röhm Gmbh Verfahren zur herstellung von alpha-hydroxyisobuttersäuremethylester und dessen anwendung in der elektronik-industrie

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JP6760299B2 (ja) 2020-09-23
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WO2017057320A1 (ja) 2017-04-06
KR102605799B1 (ko) 2023-11-23
TW201730144A (zh) 2017-09-01
US11046634B2 (en) 2021-06-29
TWI698425B (zh) 2020-07-11
KR20180059472A (ko) 2018-06-04
CN108137476B (zh) 2021-03-02

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