WO2017217279A1 - イソプロピルアルコールの製造方法及び不純物が低減されたイソプロピルアルコール - Google Patents

イソプロピルアルコールの製造方法及び不純物が低減されたイソプロピルアルコール Download PDF

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WO2017217279A1
WO2017217279A1 PCT/JP2017/020929 JP2017020929W WO2017217279A1 WO 2017217279 A1 WO2017217279 A1 WO 2017217279A1 JP 2017020929 W JP2017020929 W JP 2017020929W WO 2017217279 A1 WO2017217279 A1 WO 2017217279A1
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isopropyl alcohol
propylene
methyl
water
pentanol
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PCT/JP2017/020929
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English (en)
French (fr)
Japanese (ja)
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勝己 井手西
学 鎌本
俊輔 保坂
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株式会社トクヤマ
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Priority to JP2018523674A priority Critical patent/JP6935399B2/ja
Priority to KR1020187033332A priority patent/KR102313108B1/ko
Publication of WO2017217279A1 publication Critical patent/WO2017217279A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
    • C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/02—Monohydroxylic acyclic alcohols
    • C07C31/10—Monohydroxylic acyclic alcohols containing three carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

Definitions

  • the present invention relates to a novel process for producing isopropyl alcohol and isopropyl alcohol with reduced impurities.
  • Isopropyl alcohol also called 2-propanol
  • isopropyl alcohol with reduced impurities is also used for cleaning and drying of electronic devices, and the amount of use is expected to increase in the future.
  • the production method of isopropyl alcohol includes acetone reduction method in which acetone is reduced; indirect hydration method in which propylene is esterified using concentrated sulfuric acid and then hydrolyzed; direct hydration in which propylene is directly hydrated in the presence of a catalyst. Law; etc. are known.
  • the direct hydration method has the advantage of not using a mineral acid such as sulfuric acid as compared with the indirect hydration method, and in recent years, production of isopropyl alcohol by the direct hydration method has become mainstream.
  • Non-Patent Document 1 describes a fixed bed catalyst method and a solution catalyst method as industrialized processes of the direct hydration method. More specifically, there are three production methods: Veba Chemie method as the gas phase method of the fixed bed catalyst method, Deutsche Texaco method as the gas-liquid mixed phase method of the fixed bed catalyst method, and Tokuyama Soda method as the liquid phase method of the solution catalyst method. Is described.
  • the production process of the Veba Chemie method is to synthesize, separate and purify isopropyl alcohol in the order of the reactor, scrubber (unreacted propylene recovery), low boiling tower, azeotropic tower, and dehydrating tower.
  • the raw material supply ratio of water and propylene is reacted at an equal amount, so that the amount of unreacted water is small and the water contained in the reaction mixture is small. For this reason, in the Veba Chemie method, unreacted water is not recovered and treated as waste water.
  • the manufacturing process of the Irish Texaco method is to synthesize isopropyl alcohol in the order of steps of reactor, separator (reacted unreacted propylene recovery), low boiling tower, azeotropic tower, and dehydrating tower, and separate and purify it. It is.
  • a styrene-based strongly acidic cation exchange resin is used as a catalyst in the reactor, sulfuric acid derived from the cation exchange resin is contained in the reaction mixture. Thereafter, in an azeotropic tower, water containing sulfuric acid and isopropyl alcohol are separated, and water containing sulfuric acid is recovered.
  • the Tokuyama Soda process also synthesizes isopropyl alcohol in the order of the reactor, separator (unreacted propylene recovery), azeotropic tower, low boiling tower, dehydration tower, recovery tower, and high boiling tower. Separated and purified.
  • separator unreacted propylene recovery
  • azeotropic tower low boiling tower
  • dehydration tower recovery tower
  • high boiling tower recovery tower
  • water is recovered from the bottom of the azeotropic tower and the recovered water is reused as a raw material.
  • Patent Document 4 describes that 4-methyl-2-pentanol and 2-methylpentane-2,4-diol as impurities are reduced.
  • the impurity concentration (by mass) is 1 ppm for 4-methyl-2-pentanol and 21 ppm for 2-methylpentane-2,4-diol.
  • the impurity concentration of isopropyl alcohol purified by the conventional method is insufficient for use in the recent manufacturing process of electronic devices, and the method and impurity for producing isopropyl alcohol that can further reduce the impurity concentration A reduced concentration of isopropyl alcohol was desired.
  • isopropyl alcohol is synthesized by a direct hydration method, an indirect hydration method, or an acetone reduction method, which is conventionally known as a method for producing isopropyl alcohol, and after the synthesis reaction, isopropyl alcohol is purified by a distillation step or a filtration step.
  • impurities of about several ppm derived from by-products during the synthesis reaction are contained in the purified isopropyl alcohol. Therefore, it is a big problem to be able to reduce impurities by a simple method and to improve the yield of isopropyl alcohol without incurring great equipment costs and energy costs for removing such impurities of about several ppm. Met.
  • impurities contained in isopropyl alcohol used in the manufacturing process of electronic devices impurities that must be particularly noted are high-boiling compounds having a boiling point higher than that of isopropyl alcohol. It was found that the proportion of high boiling point compounds via propylene oligomers produced by the reaction of propylene as a raw material was high.
  • a recovery step for recovering propylene from the reaction mixture obtained in such a reaction step a first distillation step for removing low-boiling compounds having a boiling point lower than that of isopropyl alcohol from the reaction mixture from which propylene was recovered in the recovery step
  • a second distillation step for removing water from the reaction mixture from which the low-boiling compounds have been removed in the first distillation step it takes a great equipment cost and energy cost to remove impurities of about several ppm.
  • impurities can be reduced by a simple method and have completed the present invention.
  • the ratio of propylene and water in the reactor is 1300 to 2100 parts by mass of water with respect to 100 parts by mass of propylene, and the residence time of water in the reactor is more than 20 minutes and 50 minutes or less. It has been found that high boiling point compounds having a higher boiling point than isopropyl alcohol can be reduced by suppressing the production of propylene oligomers without reducing the yield of isopropyl alcohol.
  • the present invention relates to a method for producing isopropyl alcohol in which propylene and water having a pH of 2.5 to 4.5 are supplied to a reactor.
  • a supply step a reaction step of reacting propylene and water in the reactor, a recovery step of recovering propylene from the reaction mixture obtained in the reaction step, and a reaction in which propylene is recovered in the recovery step
  • a first distillation step for removing low boiling point compounds having a boiling point lower than that of isopropyl alcohol from the mixture, and a reaction mixture from which the low boiling point compounds have been removed in the first distillation step to remove water to obtain isopropyl alcohol.
  • a distillation step wherein the proportion of propylene and water in the reactor is 100 parts by mass of propylene. Water is 1300-2100 parts by weight, the residence time of water in the reactor is less than or equal to 50 minutes beyond the 20 minutes, to provide a method for producing isopropyl alcohol.
  • the present invention also provides isopropyl alcohol in which the concentrations of 4-methyl-2-pentanol, 2-methyl-3-pentanone, and 4-methyl-2-pentanone as impurities are all 20 ppb or less on a mass basis. provide.
  • the production method of the present invention it is possible to suppress the production of propylene oligomers without reducing the yield of isopropyl alcohol, and the selectivity from propylene to isopropyl alcohol can be increased.
  • the concentrations of 4-methyl-2-pentanol, 2-methyl-3-pentanone, and 4-methyl-2-pentanone as impurities are all 20 ppb or less based on mass. Certain isopropyl alcohols can be produced.
  • the production of by-products is suppressed in the reaction of directly hydrating water to propylene, the load applied to the purification process after the synthesis reaction is reduced, and a distillation process or filtration for removing impurities.
  • the process can be simplified.
  • the method for producing isopropyl alcohol of the present disclosure includes a raw material supply step, a reaction step, a recovery step for recovering propylene, and removal of low boiling point compounds A first distillation step, and a second distillation step for recovering water.
  • the method of production of the present disclosure includes a raw material supply step, a reaction step, a recovery step for recovering propylene, and removal of low boiling point compounds A first distillation step, and a second distillation step for recovering water.
  • the raw materials used in the production method of the present disclosure are propylene and water.
  • propylene as a raw material is received in a recovery tank, mixed with the propylene recovered in the recovery process in the recovery tank, and supplied to the reactor.
  • the raw material water is received in the recovery tank, and the water recovered in the second distillation step is mixed in the recovery tank and supplied to the reactor.
  • propylene as a raw material, propylene having a purity of 95% by mass or more that is generally available as an industrial product can be used, and propylene having a purity of 98% by mass or more is used. Is preferred.
  • unsaturated hydrocarbon compounds such as ethylene, butene, pentene, hexene and the like are contained in propylene, they undergo hydration reaction in the reaction step and become impurities. Therefore, it is preferable that the purity of propylene as a raw material is high.
  • the conversion rate of propylene and the selectivity to isopropyl alcohol can be increased, it is not always necessary to use high-purity propylene exceeding 99% by mass.
  • the purity of propylene as a raw material may be 95 to 99% by mass or 98 to 99% by mass.
  • the catalyst required in the reaction step can be added to water as a raw material in advance.
  • the catalyst include various polyanion catalysts such as a molybdenum-based inorganic ion exchanger and a tungsten-based inorganic ion exchanger.
  • a catalyst may be used individually by 1 type and may use 2 or more types together.
  • these catalysts at least one selected from the group consisting of phosphotungstic acid, silicotungstic acid, and silicomolybdic acid is preferable from the viewpoint of reaction activity.
  • the catalyst is preferably added so that the pH of water as a raw material is measured with a pH meter and the pH at 25 ° C. is 2.5 to 4.5.
  • a catalyst so that the pH of the raw material water is in the range of 2.5 to 4.5, it is optimal for obtaining a high selectivity to isopropyl alcohol while maintaining a high propylene conversion rate. It becomes possible to set it as a favorable reaction condition, and also it becomes possible to suppress the production
  • the pH can be adjusted by adding an alkali such as sodium hydroxide.
  • an alkali such as sodium hydroxide.
  • the pH can be easily adjusted by adding a catalyst.
  • the corrosion of the piping and reactor caused by the acid can be suppressed, so that the concentration of metal ions contained in isopropyl alcohol can also be suppressed.
  • reaction process The direct hydration reaction of propylene in the reaction step is represented by the following formula. The following reaction is performed in the reactor to obtain a reaction mixture. C 3 H 6 + H 2 O ⁇ CH 3 CH (OH) CH 3
  • Non-Patent Document 1 exemplifies the Veba Chemie method as the gas phase method of the fixed bed catalyst method, the Irish Texaco method as the gas-liquid mixed phase method of the fixed bed catalyst method, and the Tokuyama Soda method as the liquid phase method of the solution catalyst method.
  • the production method of the present disclosure is an improved method of the solution catalyst method.
  • the reaction conditions are preferably a reaction pressure of 150 to 250 atm, preferably 180 to 250 atm, and a reaction temperature of 200 to 300 ° C., preferably 250 to 280 ° C. When the reaction conditions satisfy this range, the yield of industrial production and the durability of the catalyst tend to be compatible while suppressing the formation of by-products.
  • the concentration of isopropyl alcohol in the reaction mixture after recovering propylene is preferably 5.5% by mass or more, and more preferably 6.0% by mass or more. By setting it as this range, both the purity and yield of isopropyl alcohol tend to be improved.
  • the residence time of water in the reactor is more than 20 minutes and 50 minutes or less.
  • the water residence time is preferably 25 to 40 minutes, more preferably 30 to 40 minutes.
  • the residence time of water in the reactor is less than 20 minutes, the yield of isopropyl alcohol tends to be low, which is inferior in economic efficiency.
  • the residence time of water in the reactor exceeds 50 minutes, the by-product increases, whereby the selectivity of isopropyl alcohol decreases and the purity of isopropyl alcohol tends to decrease. That is, when the residence time of water in the reactor becomes longer, unreacted propylene oligomerizes, and further, hydroxyl groups and ketone groups are added, or unreacted propylene reacts with unsaturated hydrocarbon compounds as impurities. . Furthermore, the synthesized isopropyl alcohol reacts to form a dimer, or the raw material propylene or propylene oligomer is added to isopropyl alcohol. By progressing such side reactions, it is estimated that by-products increase.
  • the residence time of water in the present disclosure is a time defined by the following formula, and can be appropriately changed by changing the supply amount of water as a raw material and the volume of the reactor.
  • Water residence time (min) reactor volume (m 3 ) ⁇ water supply (m 3 / min)
  • the supply amount of water is calculated based on the flow rate of water (110 ° C. in the examples described later) supplied into the reactor.
  • First distillation step In the first distillation step, a distillation operation is performed for the purpose of removing a low-boiling compound having a boiling point lower than that of isopropyl alcohol from the reaction mixture from which propylene has been recovered in the recovery step.
  • the aqueous phase has a low boiling point compound having a lower boiling point than isopropyl alcohol (for example, olefins such as ethylene and propylene, acetone , Diisopropyl ether, and the like) in comparison with conventional production methods.
  • the low-boiling compound having a boiling point lower than that of isopropyl alcohol is removed from the water collected in the second distillation step in the first distillation step of the previous step, and can be suitably used as a raw material for isopropyl alcohol.
  • the recovered water is re-introduced into the water recovery tank in the raw material supply process, and reacted with propylene under synthesis conditions in which the water is excessive, thereby producing high-purity isopropyl alcohol with reduced by-products. Can do.
  • the isopropyl alcohol with reduced impurities obtained in the second distillation step can be further converted into isopropyl alcohol with further reduced impurities through a dehydration step and a purification step.
  • metals and inorganic particles may be removed by a filter process, or metal ions may be removed by an ion exchange resin tower.
  • the concentrations of 4-methyl-2-pentanol, 2-methyl-3-pentanone, and 4-methyl-2-pentanone as impurities are all 20 ppb or less on a mass basis.
  • the isopropyl alcohol of the present disclosure includes 1,2-propanediol, 3-methyl-2-pentanone, 2-hexanone, 3,3-dimethyl-2-butanol, 2,3-dimethyl-2-butanol as impurities, 2-methyl-2-pentanol, 3-methyl-3-pentanol, 2-methyl-3-pentanol, 1-hexanol, 2-hexanol, 3-hexanol, 3-methyl-2-pentanol, 2, 2-dimethyl-1-butanol, 2-ethyl-1-pentanol, 2-methyl-1-pentanol, 3-methyl-1-pentanol, 4-methyl-1-pentanol, 2-methyl-2,
  • concentrations of 4-pentanediol and 2,3-dimethyl-2,3-butanediol are both preferably 20 ppb or less on a mass basis.
  • the isopropyl alcohol of the present disclosure has a higher boiling point than isopropyl alcohol and the concentration of the high-boiling compound as an impurity having 5 to 12 carbon atoms is preferably 20 ppb or less on a mass basis.
  • the isopropyl alcohol of the present disclosure has a boiling point higher than that of isopropyl alcohol and the concentration of the high-boiling compound as an impurity having 5 to 30 carbon atoms is 500 ppb or less on a mass basis.
  • the isopropyl alcohol of the present disclosure has impurities with a higher boiling point than isopropyl alcohol are highly reduced, it can be used for various cleaning applications, and can be particularly suitably used as a cleaning liquid for electronic devices. . Impurities having a boiling point higher than that of isopropyl alcohol are difficult to remove in the drying step after the cleaning step and are likely to remain on the surface of the electronic device. However, by using the isopropyl alcohol of the present disclosure, the surface of the electronic device is cleaned and dried. It is possible to reduce the residue remaining in
  • the isopropyl alcohol of the present disclosure can be manufactured, for example, by the manufacturing method of the present disclosure described above.
  • the high boiling point compound as an impurity is derived from a byproduct resulting from the side reaction of the direct hydration reaction. That is, since isopropyl alcohol is synthesized using propylene having 3 carbon atoms as a raw material, side reactions such as a side reaction that produces a dimer of propylene and a side reaction that produces a dimer of isopropyl alcohol are considered. . For this reason, isopropyl alcohol often contains hydrocarbon compounds having 6, 9, and 12 carbon atoms as impurities. Further, since water is present in the reaction field of the above side reaction, a hydroxyl group or a ketone group may be introduced into the byproduct. For this reason, an alcohol in which a hydroxyl group is introduced into a hydrocarbon compound having 6, 9 or 12 carbon atoms or a ketone in which a ketone group is introduced may be contained as an impurity.
  • the proportion of propylene and water in the reactor is 1300 to 2100 parts by mass of water with respect to 100 parts by mass of propylene, and the residence time of water in the reactor is By setting it to more than 20 minutes and not more than 50 minutes, the selectivity to isopropyl alcohol can be increased while maintaining the yield of isopropyl alcohol. As a result, high purity of isopropyl alcohol can be easily achieved without overloading the isopropyl alcohol purification process.
  • the total amount of impurities contained in isopropyl alcohol can be further reduced.
  • the total concentration of high-boiling compounds as impurities having a boiling point higher than that of isopropyl alcohol and having 5 to 12 carbon atoms is preferably 1 ppm or less, more preferably 100 ppb or less, even more preferably 20 ppb or less, particularly Preferably it can also be 10 ppb or less.
  • the concentration of the salt having an organic acid skeleton having 10 or less carbon atoms and its derivative as impurities can be reduced.
  • the low boiling point compound is discharged out of the system, so that not only the high boiling point compound but also the concentration of the low boiling point compound is reduced. Can be reduced.
  • a linear hydrocarbon compound having 4 or 5 carbon atoms contained as an impurity in propylene as a raw material for example, a linear alkane such as butane, pentane, or hexane can be given.
  • Other examples of the low-boiling compounds include propylene oligomers and diisopropyl ether derived from raw material propylene.
  • concentration condition of the high-boiling compounds for example, distillation is performed for 24 hours with a precision distillation apparatus at a column top temperature of about 82 ° C.
  • the number of theoretical plates in the precision distillation apparatus is 2 to 30. If the number of plates is within this range, distillation and concentration can be performed.
  • GC-MS gas chromatograph-mass spectrometer
  • the concentration of high-boiling organic substances having 5 to 30 carbon atoms is detected if no peak is detected in the region obtained with the above conditions, where the retention time is longer than that of isopropyl alcohol. It can be evaluated that the lower limit is 500 ppb or less.
  • Carrier gas Helium carrier gas Flow rate: 2 mL / min
  • Transfer line temperature: 240 ° C Ion source, quadrupole temperature: 230 ° C, 150 ° C Scan ion: m / Z 25-250
  • the concentration of the low boiling point organic substance is 5000 ppb or less, which is the lower limit of detection Can be evaluated.
  • Example 1 [Production of isopropyl alcohol]
  • propylene as a raw material, as shown in Table 1, those containing 39972 ppm propane, 20 ppm ethane, 8 ppm butene, 0.1 ppm or less pentene, and 0.1 ppm or less hexene as impurities were prepared.
  • a phosphotungstic acid as a catalyst was added to adjust the pH to 3.0.
  • water heated to 110 ° C. is supplied to a reactor having an internal volume of 10 L at a supply rate of 18.4 kg / h (since the density is 920 kg / m 3 , 20 L / h).
  • propylene was added at a supply rate of 1.2 kg / h (raw material supply step).
  • the residence time of water in the reactor at this time is 30 minutes, and 1500 parts by mass of water is supplied to 100 parts by mass of propylene.
  • the reaction temperature in the reactor was 280 ° C.
  • the reaction pressure was 250 atm
  • propylene and water were reacted to obtain isopropyl alcohol (reaction step).
  • reaction mixture containing isopropyl alcohol produced in the reaction step was cooled to 140 ° C., and the pressure was reduced to 18 atm, whereby propylene dissolved in water contained in the reaction mixture was recovered as a gas (recovery step). .
  • the recovered propylene was put into a propylene recovery tank for reuse as a raw material.
  • the reaction mixture was extracted from the bottom of the distillation column and separated into water and isopropyl alcohol using the distillation column (second distillation step).
  • the water extracted from the bottom of the column and collected was placed in a water recovery tank for reuse as a raw material under conditions of a temperature of 110 ° C. and a pressure of 1.5 atm. Further, phosphotungstic acid was added and adjusted so that the pH of the recovered water was maintained at 3.0.
  • isopropyl alcohol extracted from the top of the column contains about 13% of water, a distillation step for dehydration and a distillation step for purifying isopropyl alcohol were performed to obtain isopropyl alcohol.
  • concentration of 2,3-dimethyl-2,3-butanediol was 20 ppb or less, which is the lower limit of detection.
  • tertiary butanol contained as a high boiling point compound is derived from butene contained in the raw material propylene, but could not be separated because the boiling point was 82.4 ° C., the same as isopropyl alcohol.
  • Example 2 [Production of isopropyl alcohol]
  • the water supply rate was 13.8 kg / h (the density was 920 kg / m 3 , so 15 L / h), the propylene supply rate was 0.9 kg / h, and the water residence time in the reactor was 40 minutes. Except that, isopropyl alcohol was produced in the same manner as in Example 1.
  • concentration of 2,3-dimethyl-2,3-butanediol was 20 ppb or less, which is the lower limit of detection.
  • Example 3 [Production of isopropyl alcohol] The same as Example 1 except that as the raw material propylene, what contained 19956 ppm propane, 40 ppm ethane, 4 ppm butene, 0.1 ppm or less pentene, and 0.1 ppm or less hexene as impurities was used. Thus, isopropyl alcohol was produced.
  • concentration of 2,3-dimethyl-2,3-butanediol was 20 ppb or less, which is the lower limit of detection.
  • Example 4 [Production of isopropyl alcohol]
  • the amount of water supplied is 18.4 kg / h (20 L / h because the density is 920 kg / m 3 ), the amount of propylene supplied is 0.9 kg / h, and the amount of water supplied to 100 parts by mass of propylene is 2000 masses.
  • Isopropyl alcohol was produced in the same manner as in Example 1 except that the parts were changed to parts.
  • concentration of 2,3-dimethyl-2,3-butanediol was 20 ppb or less, which is the lower limit of detection.
  • the concentration of 4-methyl-2-pentanol as an impurity was 37 ppb
  • the concentration of 2-methyl-3-pentanone was 35 ppb
  • the concentration of 4-methyl-2-pentanone was 36 ppb.
  • Comparative Example 1 the concentration of isopropyl alcohol in the reaction mixture was 1.1 to 1.5 times that of Examples 1 to 4 and the yield was increased.
  • the concentration of the high-boiling compound in the sample was higher than 20 ppb, and the purity was lower than in Examples 1 to 4.
  • the concentration of the high boiling point compound having 5 to 30 carbon atoms was evaluated to be 500 ppb or less.
  • the concentration of 4-methyl-2-pentanol as an impurity was 45 ppb
  • the concentration of 2-methyl-3-pentanone was 41 ppb
  • the concentration of 4-methyl-2-pentanone was 50 ppb.
  • Comparative Example 2 the concentration of isopropyl alcohol in the reaction mixture was comparable to that in Examples 1 to 4 and the yield was maintained. The concentration was higher than 20 ppb, and the purity was lower than in Examples 1 to 4.

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PCT/JP2017/020929 2016-06-17 2017-06-06 イソプロピルアルコールの製造方法及び不純物が低減されたイソプロピルアルコール WO2017217279A1 (ja)

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WO2020071307A1 (ja) * 2018-10-03 2020-04-09 株式会社トクヤマ 高純度イソプロピルアルコール及びその製造方法
CN112771015A (zh) * 2018-10-05 2021-05-07 株式会社德山 异丙醇的制造方法
WO2021200936A1 (ja) * 2020-04-02 2021-10-07 株式会社トクヤマ 半導体処理液及びその製造方法
WO2021261682A1 (ko) * 2020-06-23 2021-12-30 주식회사 엘지화학 이소프로필 알코올 제조방법
EP4122908A4 (en) * 2021-05-31 2023-08-23 Lg Chem, Ltd. METHOD FOR PREPARING ISOPROPYL ALCOHOL
WO2023176192A1 (ja) * 2022-03-16 2023-09-21 株式会社トクヤマ 半導体洗浄液および半導体洗浄液の製造方法
JP7354494B2 (ja) 2021-05-31 2023-10-03 エルジー・ケム・リミテッド イソプロピルアルコールの製造方法

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KR20220151452A (ko) * 2021-05-06 2022-11-15 주식회사 엘지화학 이소프로필 알코올 제조방법
TWI815364B (zh) * 2022-03-22 2023-09-11 金兆鎔科技股份有限公司 電子級異丙醇回收純化方法及系統
WO2024034794A1 (ko) * 2022-08-11 2024-02-15 주식회사 엘지화학 이소프로필 알코올의 제조 방법 및 제조 장치
CA3237292A1 (en) * 2022-08-22 2024-02-29 Lg Chem, Ltd. Method for preparing isopropyl alcohol

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