WO2021140869A1 - 有機亜鉛触媒の製造方法 - Google Patents

有機亜鉛触媒の製造方法 Download PDF

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WO2021140869A1
WO2021140869A1 PCT/JP2020/047342 JP2020047342W WO2021140869A1 WO 2021140869 A1 WO2021140869 A1 WO 2021140869A1 JP 2020047342 W JP2020047342 W JP 2020047342W WO 2021140869 A1 WO2021140869 A1 WO 2021140869A1
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acid
reaction
catalyst
mass
organozinc
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PCT/JP2020/047342
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English (en)
French (fr)
Japanese (ja)
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匠 藤野
直久 早水
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住友精化株式会社
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Priority to KR1020227015128A priority Critical patent/KR20220122599A/ko
Priority to JP2021569803A priority patent/JPWO2021140869A1/ja
Publication of WO2021140869A1 publication Critical patent/WO2021140869A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/06—Zinc compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates

Definitions

  • the present disclosure relates to a method for producing an organozinc catalyst, an organozinc catalyst produced by the production method, and the like.
  • the contents of all documents described herein are incorporated herein by reference.
  • an organozinc compound obtained by reacting an inorganic zinc compound with an aliphatic dicarboxylic acid and an aliphatic monocarboxylic acid is used as an organozinc catalyst for catalyzing a reaction for obtaining a polyalkylene carbonate from carbon dioxide and epoxide.
  • the present inventors studied for the purpose of efficiently obtaining the organozinc catalyst.
  • the present inventors In producing an organozinc catalyst, the present inventors have found that the amount of water in the reaction system when reacting an inorganic zinc compound with an aliphatic carboxylic acid may affect the yield of the obtained organozinc catalyst. , Further examination was repeated.
  • Item 1 Including reacting inorganic zinc compounds and aliphatic carboxylic acids The water content of the reaction system at the start of the reaction is 0.05 to 10% by mass with respect to the inorganic zinc compound.
  • Method for producing organozinc compound Item 2.
  • Item 2. The production method according to Item 1, wherein the inorganic zinc compound is at least one selected from the group consisting of zinc oxide and zinc hydroxide.
  • Item 3. Item 2. The production method according to Item 1 or 2, wherein the aliphatic carboxylic acid is at least one selected from the group consisting of an aliphatic dicarboxylic acid and an aliphatic monocarboxylic acid.
  • Item 8. An organozinc compound obtained by the production method according to any one of Items 1 to 7.
  • Item 9. Item 8.
  • an inorganic zinc compound is reacted with an aliphatic carboxylic acid in producing an organozinc compound which can be preferably used as a catalyst (particularly, a catalyst in a reaction for obtaining a polyalkylene carbonate from carbon dioxide and epoxide).
  • an organozinc compound which can be preferably used as a catalyst (particularly, a catalyst in a reaction for obtaining a polyalkylene carbonate from carbon dioxide and epoxide).
  • the yield of the obtained polypropylene carbonate can be improved.
  • the present disclosure preferably includes, but is not limited to, a method for producing a specific organozinc compound, an organozinc compound produced by the method, and the use of the organozinc compound as a catalyst.
  • the present disclosure includes everything disclosed herein and recognizable to those skilled in the art.
  • the method for producing an organozinc compound included in the present disclosure includes reacting an inorganic zinc compound with an aliphatic carboxylic acid, and the water content of the reaction system at the start of the reaction is 0 with respect to the zinc compound. It is a manufacturing method of .05 to 10% by mass.
  • the production method included in the present disclosure may be referred to as "the organic zinc compound production method of the present disclosure”.
  • the organozinc compound may be referred to as "organozinc compound of the present disclosure”.
  • the organozinc compound of the present disclosure can be used as a catalyst (particularly, a catalyst in a reaction for obtaining a polyalkylene carbonate from carbon dioxide and an epoxide).
  • the catalyst may be referred to as "the catalyst of the present disclosure”.
  • the organozinc compound of the present disclosure is obtained by reacting an inorganic zinc compound with an aliphatic carboxylic acid.
  • the organozinc compound of the present disclosure can be said to be a reaction product of an inorganic zinc compound and an aliphatic carboxylic acid.
  • Examples of the inorganic zinc compound include zinc oxide, zinc sulfate, zinc chlorate, zinc nitrate, zinc acetate, and zinc hydroxide, and zinc oxide and zinc hydroxide are more preferable.
  • the inorganic zinc compound may be used alone or in combination of two or more.
  • an aliphatic carboxylic acid for example, an aliphatic monocarboxylic acid, an aliphatic dicarboxylic acid, an aliphatic tricarboxylic acid and the like can be used. Of these, it is preferable to use an aliphatic dicarboxylic acid.
  • the aliphatic carboxylic acid can be used alone or in combination of two or more. Of these, it is preferable to use an aliphatic dicarboxylic acid, or to use an aliphatic dicarboxylic acid and an aliphatic monocarboxylic acid.
  • the molar ratio of the aliphatic monocarboxylic acid to the aliphatic dicarboxylic acid is about 0.0001 to 0.1 or 0.001 to 0.05. It is preferable to use it so as to be a degree.
  • an aliphatic dicarboxylic acid having 2 to 15 carbon atoms (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15) is preferable. More specifically, for example, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid and the like can be mentioned.
  • the aliphatic monocarboxylic acid has 1 to 15 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15).
  • Monocarboxylic acids are preferred, and more specific examples include formic acid, acetic acid, propionic acid, trifluoroacetic acid and the like.
  • an aliphatic tricarboxylic acid having 3 to 15 carbon atoms is preferable, and more specific.
  • examples thereof include tricarbaryl acid and 3,3', 3''-nitrilotripropionic acid.
  • malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid, formic acid, acetic acid, and propionic acid are particularly preferable.
  • the water content of the reaction system at the start of the reaction is 0.05 to 10% by mass with respect to the inorganic zinc compound.
  • the lower limit of the range may be, for example, about 0.1, 0.15, 0.2, or 0.25% by mass.
  • the upper limit of the range may be, for example, about 9.5, 9, 8.5, 8, 7.5, 7, 6.5, or 6% by mass.
  • the water content of the reaction system at the start of the reaction is measured as follows. That is, after charging the raw materials (inorganic zinc compound, aliphatic carboxylic acid and other components (for example, solvent)) into the reaction vessel, the mixture is stirred, and 0.5 g of the mixture is sampled within 1 minute from the start of stirring. 5 g of methanol is added to the mixture and mixed. After filtering the mixed solution with a 0.45 ⁇ m filter, the filtrate is introduced into a Karl Fischer moisture meter to measure the water content.
  • the raw materials inorganic zinc compound, aliphatic carboxylic acid and other components (for example, solvent)
  • the ratio of the inorganic zinc compound and the aliphatic carboxylic acid used is preferably about 0.1 to 1.5 mol, preferably about 0.5 to 1.2 mol, with respect to 1 mol of the inorganic zinc compound. Is more preferable, and about 0.8 to 1.0 mol is further preferable.
  • the reaction between the inorganic zinc compound and the aliphatic carboxylic acid a known reaction can be used, and for example, the reaction conditions described in Patent Document 1 or 2 can be used. More specifically, for example, the reaction solvent is not particularly limited, and various organic solvents can be used. Specific examples of such an organic solvent include aromatic hydrocarbon solvents such as benzene, toluene and xylene, aliphatic solvent such as hexane, heptane and cyclohexane, dichloromethane, chloroform, 1 and 2.
  • aromatic hydrocarbon solvents such as benzene, toluene and xylene
  • aliphatic solvent such as hexane, heptane and cyclohexane
  • dichloromethane chloroform
  • -Halogen-based hydrocarbon solvents such as dichloroethane, alcohol-based solvents such as methanol, ethanol and isopropanol, ether-based solvents such as diethyl ether, tetrahydrofuran and dioxane, ester-based solvents such as ethyl acetate and butyl acetate, acetone and methylethiel ketone.
  • Ketone-based solvents such as methyl isobutyl ketone
  • carbonate-based solvents such as dimethyl carbonate, diethyl carbonate and propylene carbonate
  • acetonitrile dimethylformamide, dimethylsulfoxide, hexamethylphosphotriamide and the like.
  • aromatic hydrocarbon solvents such as benzene, toluene, and xylene are preferable from the viewpoint of facilitating the reaction.
  • the amount of the reaction solvent used is not particularly limited, but from the viewpoint of facilitating the reaction and obtaining an effect commensurate with the amount used, for example, 500 to 10000 parts by mass with respect to 100 parts by mass of the inorganic zinc compound. Is preferable.
  • the reaction temperature is not particularly limited, but is preferably 0 to 110 ° C, more preferably 20 to 100 ° C, and even more preferably 50 to 80 ° C.
  • the reaction temperature is 0 ° C. or higher, the reaction can proceed more efficiently. Further, when the reaction temperature is 110 ° C. or lower, side reactions are less likely to occur, and a decrease in yield can be suppressed.
  • the reaction time varies depending on the reaction temperature and cannot be unequivocally determined, but is, for example, about 1 to 50 hours.
  • reaction is preferably carried out in an atmosphere of an inert gas (for example, nitrogen).
  • an inert gas for example, nitrogen
  • an organozinc compound obtained by reacting at least zinc oxide and glutaric acid can be mentioned as a particularly preferable form of the organozinc compound of the present disclosure.
  • the organozinc compound was reacted with only zinc oxide as the inorganic zinc compound, reacted with only glutaric acid as the aliphatic carboxylic acid, or reacted with only zinc oxide and glutaric acid. Those are preferably included.
  • the organozinc compound of the present disclosure is particularly preferably used for catalyzing a reaction (copolymerization reaction) for obtaining a polyalkylene carbonate from carbon dioxide and an epoxide.
  • the present disclosure also preferably includes a method for producing a polyalkylene carbonate by reacting carbon dioxide and an epoxide in the presence of the organozinc compound of the present disclosure (copolymerization reaction).
  • the epoxide is not particularly limited, but for example, ethylene oxide, propylene oxide, 1-butane oxide, 2-butane oxide, isobutylene oxide, 1-pentene oxide, 2-pentene oxide, 1-hexene oxide, 1-.
  • the working pressure of carbon dioxide is not particularly limited, but is usually preferably 0.1 to 20 MPa, more preferably 0.1 to 10 MPa, and even more preferably 0.1 to 5 MPa. Carbon dioxide may be supplied in a lump sum, intermittently, or continuously.
  • the amount of the organozinc catalyst used is, for example, preferably 0.001 to 50 parts by mass, more preferably 0.01 to 40 parts by mass, and 0.1 to 30 parts by mass with respect to 100 parts by mass of the epoxide. It is more preferably a part.
  • the solvent used in the copolymerization reaction is not particularly limited, and various organic solvents can be used.
  • organic solvent include aliphatic hydrocarbon solvents such as pentane, hexane, octane, decane and cyclohexane; aromatic hydrocarbon solvents such as benzene, toluene and xylene; dichloromethane and chloroform.
  • 1,2-Dichloroethane chlorobenzene, bromobenzene and other halogenated hydrocarbon solvents
  • ethyl acetate isopropyl acetate, butyl acetate and other ester solvents
  • tetrahydrofuran, 1,4-dioxane and other ether solvents dimethyl carbonate
  • carbonate solvents such as diethyl carbonate and propylene carbonate.
  • the amount of the solvent used is not particularly limited, but is, for example, 100 to 10000 parts by mass with respect to 100 parts by mass of the epoxide from the viewpoint of smoothing the reaction and obtaining an effect commensurate with the amount used. Is preferable. Moreover, it is not necessary to use a solvent.
  • the method for producing the polyalkylene carbonate has different polymerization forms such as solution polymerization and precipitation polymerization depending on the type and amount of the solvent used, but the copolymerization reaction proceeds without any problem in any of the polymerization forms. , Their reaction efficiency is very high.
  • the reaction temperature of the copolymerization reaction is not particularly limited, but is preferably, for example, 20 to 100 ° C, more preferably 40 to 80 ° C.
  • the reaction time cannot be unequivocally determined because it varies depending on the reaction temperature, but is, for example, 2 to 40 hours.
  • the method for mixing the organozinc catalyst with carbon dioxide and epoxide is not particularly limited, but for ease of mixing, for example, there is a method of adding carbon dioxide after mixing the organozinc catalyst with epoxide. ..
  • the polyalkylene carbonate thus obtained is dried by using a vacuum drying method or the like after removing the catalyst or the like by filtration or washing with a dilute acid aqueous solution or a dilute alkaline aqueous solution, if necessary, and then reprecipitating.
  • a vacuum drying method or the like after removing the catalyst or the like by filtration or washing with a dilute acid aqueous solution or a dilute alkaline aqueous solution, if necessary, and then reprecipitating.
  • ⁇ Analyzer TG / DTA 7220 (manufactured by Hitachi High-Tech Science Corporation) -Sample pretreatment: 1 g of slurry is collected and dried at 70 ° C. under reduced pressure (1 kPa ⁇ abs) for 1 Hr.
  • ⁇ Analytical conditions 30 to 300 ° C. 10 ° C./min Atmosphere N 2 200 mL / min, Sample 5 mg ⁇ 1 mg -Analysis conditions: Since the catalyst using zinc oxide and glutaric acid is described in this example, the case of zinc oxide and glutaric acid is also shown as an example for the analysis conditions such as the calculation method.
  • the tangent at 100 ° C was T 1
  • the tangent at 250 ° C was T 2
  • the tangent at the inflection point between 100 and 250 ° C was T 3 .
  • the mass W 1 at the intersection of the tangents T 1 and T 3 was obtained.
  • the mass W 2 at the intersection of the tangents T 2 and T 3 was obtained.
  • the mass difference between the intersections (W 1- W 2 ) is defined as the glutaric acid (aliphatic carboxylic acid) content, and the value obtained by dividing the glutaric acid (aliphatic carboxylic acid) content by the mass W 1 of the intersection on the low temperature side is calculated.
  • the content of glutaric acid (aliphatic carboxylic acid) was used (see FIG. 1 and Formula 1).
  • R CA glutaric acid (aliphatic carboxylic acids) according to Equation 2.
  • R CA [%] (1-C CA / C 0 ) x 100 (Equation 2)
  • R CA Glutaric acid (aliphatic carboxylic acid) reaction rate [%]
  • C CA Glutaric acid (aliphatic carboxylic acid) content [%]
  • C 0 Glutaric acid (aliphatic carboxylic acid) content at the time of preparation [%]
  • C 0 (glutaric acid (aliphatic carboxylic acid) content at the time of preparation) was calculated from the following formula 3.
  • C 0 [%] ⁇ W CA / (W CA + W Zn ) ⁇ ⁇ 100 (Equation 3)
  • C 0 Glutaric acid (aliphatic carboxylic acid) content at the time of preparation [%]
  • W CA Amount of charged glutaric acid (aliphatic carboxylic acid) [g]
  • W Zn Amount of zinc oxide (zinc compound) charged [g]
  • Example 1 Production of Organozinc Compound 81 g (1.00 mol) of zinc oxide, 132 g (1.00 mol) of glutaric acid, and 1000 g of toluene were charged into a 1.5 L volume separable flask equipped with a cooling tube / thermometer and a stirrer. When the mixed solution was sampled and the water content was measured, the water content with respect to zinc oxide (100% by mass) was 0.1% by mass. Then, the temperature was raised to 60 ° C. under a nitrogen atmosphere, and the mixture was stirred and reacted at the same temperature for 6 hours. The mixed solution after the reaction was sampled, the amount of residual glutaric acid was measured, and the reaction rate was calculated.
  • the powder was used as an organozinc catalyst in the production of polypropylene carbonate.
  • the powder is also referred to as a catalytic dry powder.
  • Example 2 In the production of the catalyst of Example 1, 195 g of dry catalyst powder was obtained in the same manner as in Example 1 except that 0.20 g of water was added at the time of preparation. The water content at the initial stage of the reaction was 0.26% by mass with respect to zinc oxide, and the reaction rate of the reaction 6Hr was 98.0% by mass. Using this catalyst, polymerization was carried out in the same manner as in Example 1 to obtain 87 g of polypropylene carbonate (yield 85% by mass, molecular weight Mw 351,000).
  • Example 3 In the production of the catalyst of Example 1, 195 g of dry catalyst powder was obtained in the same manner as in Example 1 except that 0.4 g of water was added at the time of preparation. The water content at the initial stage of the reaction was 0.42% by mass with respect to zinc oxide, and the reaction rate of the reaction 6 hours was 98.0% by mass. Using this catalyst, polymerization was carried out in the same manner as in Example 1 to obtain 84 g of polypropylene carbonate (yield 82% by mass, molecular weight Mw 336,000).
  • Example 4 In the production of the catalyst of Example 1, 195 g of dry catalyst powder was obtained in the same manner as in Example 1 except that 4.00 g of water was added at the time of preparation. The water content at the initial stage of the reaction was 5.12% by mass with respect to zinc oxide, and the reaction rate of the reaction 6Hr was 97.5% by mass. Using this catalyst, polymerization was carried out in the same manner as in Example 1 to obtain 86 g of polypropylene carbonate (yield 84% by mass, molecular weight Mw 317,000).
  • Example 5 In the production of the catalyst of Example 1, 196 g of dry catalyst powder was obtained in the same manner as in Example 1 except that 7.00 g of water was added at the time of preparation. The water content at the initial stage of the reaction was 8.55% by mass with respect to zinc oxide, and the reaction rate of the reaction 6Hr was 95.6% by mass. Using this catalyst, polymerization was carried out in the same manner as in Example 1 to obtain 84 g of polypropylene carbonate (yield 82% by mass, molecular weight Mw 326,000).
  • Example 2 In the production of the catalyst of Example 1, 197 g of dry catalyst powder was obtained in the same manner as in Example 1 except that 9.00 g of water was added at the time of preparation. The water content at the initial stage of the reaction was 11.50% by mass with respect to zinc oxide, and the reaction rate of the reaction 6 hours was 90.9% by mass. Using this catalyst, polymerization was carried out in the same manner as in Example 1 to obtain 78 g of polypropylene carbonate (yield 76% by mass, molecular weight Mw 289,000).
  • the water content of the reaction system at the start of the reaction is 0.05 with respect to the inorganic zinc compound. It was found that the reaction occurred with high efficiency when the content was ⁇ 10% by mass. Furthermore, it was found that a polyalkylene carbonate having a relatively large molecular weight can be obtained in a high yield by using an organozinc compound produced under these conditions as a catalyst when reacting carbon dioxide with an epoxide.

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PCT/JP2020/047342 2020-01-08 2020-12-18 有機亜鉛触媒の製造方法 WO2021140869A1 (ja)

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JP2018531314A (ja) * 2016-03-11 2018-10-25 エルジー・ケム・リミテッド 熱安定性および加工性が向上したポリアルキレンカーボネートを含む樹脂組成物の経済的製造方法

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JP5095954B2 (ja) 2006-05-09 2012-12-12 住友精化株式会社 有機亜鉛触媒およびそれを用いたポリアルキレンカーボネートの製造方法
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