WO2021140868A1 - Catalyseur à base d'organate-zinc - Google Patents

Catalyseur à base d'organate-zinc Download PDF

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Publication number
WO2021140868A1
WO2021140868A1 PCT/JP2020/047341 JP2020047341W WO2021140868A1 WO 2021140868 A1 WO2021140868 A1 WO 2021140868A1 JP 2020047341 W JP2020047341 W JP 2020047341W WO 2021140868 A1 WO2021140868 A1 WO 2021140868A1
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Prior art keywords
catalyst
acid
organozinc catalyst
zinc
organozinc
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PCT/JP2020/047341
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English (en)
Japanese (ja)
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中村　陽一
宗輝 前田
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住友精化株式会社
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Priority to JP2021569802A priority Critical patent/JPWO2021140868A1/ja
Priority to KR1020227015127A priority patent/KR20220125214A/ko
Publication of WO2021140868A1 publication Critical patent/WO2021140868A1/fr

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    • 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
    • C08G64/20—General preparatory processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • 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
    • 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
    • C08G64/20—General preparatory processes
    • C08G64/32—General preparatory processes using carbon dioxide
    • 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
    • C08G64/20—General preparatory processes
    • C08G64/32—General preparatory processes using carbon dioxide
    • C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers

Definitions

  • the present disclosure relates to an organozinc catalyst and a method for producing a polyalkylene carbonate using the catalyst.
  • the contents of all documents described herein are incorporated herein by reference.
  • an organozinc compound obtained by reacting a 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 have studied to develop a method for controlling the molecular weight of polyalkylene carbonate when reacting carbon dioxide with epoxide to obtain polyalkylene carbonate.
  • the present inventors have found that the water content of a specific organozinc catalyst that catalyzes the reaction of obtaining a polyalkylene carbonate from carbon dioxide and an epoxide may be related to the molecular weight of the obtained polyalkylene carbonate, and further improvements have been made. Stacked.
  • the organozinc compound used as a catalyst When the organozinc compound used as a catalyst is completely dried, it does not show the activity of catalyzing the reaction for obtaining the polyalkylene carbonate, or the activity is very low. Although it is described in Cited Document 3 that water is added and used as a catalyst, the amount of water added is about 2 ppm at most.
  • Item 1 An organozinc catalyst obtained by reacting a zinc compound and a carboxylic acid. Moisture content is 10 to 10000 ppm, Organozinc catalyst.
  • Item 2. The organozinc catalyst according to Item 1, which is obtained by reacting a zinc compound and a dicarboxylic acid.
  • Item 3. The organozinc catalyst according to Item 1, which is obtained by reacting a zinc compound, a dicarboxylic acid, and a monocarboxylic acid.
  • the dicarboxylic acid is an aliphatic dicarboxylic acid having 2 to 15 carbon atoms (preferably at least one selected from the group consisting of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid and sebacic acid).
  • the dicarboxylic acid is an aliphatic dicarboxylic acid having 2 to 15 carbon atoms (preferably at least one selected from the group consisting of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid and sebacic acid).
  • the monocarboxylic acid is an aliphatic monocarboxylic acid having 1 to 15 carbon atoms (preferably at least one selected from the group consisting of formic acid, acetic acid, propionic acid, and trifluoroacetic acid).
  • Item 3. The organozinc catalyst according to Item 3.
  • Item 6. Item 2. The organozinc catalyst according to any one of Items 1 to 5, wherein the zinc compound is zinc oxide and / or zinc hydroxide.
  • the organozinc catalyst according to Item 1 which is obtained by reacting at least zinc oxide and glutaric acid.
  • Item 9 The present invention comprises reacting carbon dioxide with an epoxide in the presence of the organozinc catalyst according to any one of Items 1 to 8 to produce a polyalkylene carbonate.
  • the present disclosure preferably includes, but is not limited to, a specific organozinc catalyst, a method for producing a polyalkylene carbonate under the catalyst, and the like, and the present disclosure is disclosed in the present specification and recognized by those skilled in the art. Include everything you can.
  • the organozinc catalyst included in the present disclosure is an organozinc catalyst obtained by reacting a zinc compound and a carboxylic acid, and has a water content of 10 to 10,000 ppm.
  • the catalyst included in the present disclosure may be referred to as “organozinc catalyst of the present disclosure” or “catalyst of the present disclosure”.
  • the catalyst of the present disclosure is obtained by reacting a zinc compound and an aliphatic carboxylic acid.
  • the catalyst of the present disclosure can be said to be a reaction product of a zinc compound and an aliphatic carboxylic acid.
  • an inorganic zinc compound is preferable.
  • 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 zinc compound may be used alone or in combination of two or more.
  • the aliphatic carboxylic acid it is preferable to use at least an aliphatic dicarboxylic acid. Further, an aliphatic monocarboxylic acid and an aliphatic tricarboxylic acid can also be used. 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 ratio of the zinc compound and the aliphatic carboxylic acid used is, for example, preferably about 0.1 to 1.5 mol, more preferably about 0.5 to 1.2 mol, based on 1 mol of the zinc compound. It is preferable, and more preferably about 0.8 to 1.0 mol.
  • the reaction between the 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, methyl ethyl ketone and methyl isobutyl.
  • ketone solvents such as ketones
  • carbonate 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 is 500 to 10000 parts by mass with respect to 100 parts by mass of the zinc compound, for example, from the viewpoint of smoothing the reaction and obtaining an effect commensurate with the amount used. It is preferable to have.
  • 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, 1 to 20 hours.
  • reaction is preferably carried out in an atmosphere of an inert gas (for example, nitrogen).
  • an inert gas for example, nitrogen
  • an organic zinc catalyst obtained by reacting at least zinc oxide and glutaric acid can be mentioned as a particularly preferable form of the catalyst of the present disclosure.
  • the organozinc catalyst is, for example, one in which only zinc oxide is reacted as a zinc compound, one in which only glutaric acid is reacted as an aliphatic carboxylic acid, or one in which only zinc oxide and glutaric acid are reacted. Is preferably included.
  • the catalyst of the present disclosure has a water content of 10 to 10000 ppm.
  • the lower limit of the range may be, for example, 20, 30, 40, 50, 60, 70, 80, 90, or 100 ppm.
  • the upper limit of the range may be, for example, 9000, 8000, 7000, 6000, 5000, 4000, 3000, 2000, or 1800 ppm.
  • the range is preferably 10 to 5000 ppm, more preferably 20 to 3000 ppm.
  • the water content is a value obtained by vaporizing the water content in the catalyst and measuring the water content by the Karl Fischer method.
  • a moisture vaporizer for example, manufactured by Hiranuma Sangyo, product name "EV-6" can be used for moisture vaporization in the catalyst. Further, for the measurement by the Karl Fischer method, a Karl Fischer moisture meter (for example, manufactured by Hiranuma Sangyo, product name "AQ-300”) can be used.
  • the catalyst of the present disclosure is 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 (copolymerizing) carbon dioxide and an epoxide under the catalyst of the present disclosure.
  • 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, diethyl Examples thereof include carbonate-based solvents such as 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.
  • the present disclosure includes reacting carbon dioxide with an epoxide in the presence of the organozinc catalyst to produce a polyalkylene carbonate, and the polyalkylene carbonate produced using the water content of the organozinc catalyst used as an index. Also preferably includes a method of controlling the molecular weight of.
  • the present inventors In the reaction of carbon dioxide and epoxide in the presence of the organozinc catalyst to produce polyalkylene carbonate, the present inventors have a water content of 10 to 10000 ppm (preferably, for example, 10 to 5000 ppm) of the organozinc catalyst. , More preferably in the range of, for example, 20 to 3000 ppm), it was found that there is a correlation between the water content and the molecular weight of the obtained polyalkylene carbonate.
  • the molecular weight of the polypropylene carbonate to be produced can be controlled by adjusting the water content of the organozinc catalyst. Further, the water content of the organozinc catalyst can be appropriately adjusted by adjusting the drying treatment (for example, adjusting the drying treatment time).
  • the molecular weight of the polypropylene carbonate to be produced is about 10,000 to 40,000 (preferably about 20,000 to 35,000), it correlates strongly with the water content of the organozinc catalyst.
  • it is particularly preferable to use this method.
  • Moisture meter analysis conditions / generated liquid "Hydranal Coulomat AK” manufactured by Sigma-Aldrich ⁇
  • Counter electrode Sigma-Aldrich
  • Hydranal Coulomat CG-K Moisture vaporizer temperature: 120 °C ⁇ Wait time: 5 minutes ⁇ Analysis time: 30 minutes
  • Example 1 Production of organozinc catalyst 81 g (1.00 mol) of zinc oxide, 132 g (1.00 mol) of glutaric acid, 1000 g of toluene in a 1.5 L volume separable flask equipped with a cooling tube / thermometer and a stirrer. Was prepared. Then, the temperature was raised to 60 ° C. under a nitrogen atmosphere, and the mixture was stirred and reacted at the same temperature for 8 hours. Then, the mixture was cooled to room temperature and suction filtered to obtain 310 g of a zinc catalyst (moisture content: 20000 ppm, hereinafter referred to as undried zinc catalyst). By drying 50 g of this undried zinc catalyst at 90 ° C.
  • Example 2 By drying 50 g of the undried zinc catalyst of Example 1 at 90 ° C. and 7.5 mmHg for 2 hours, 29 g of a catalyst having a water content of 696 ppm was obtained. Using this catalyst, polymerization was carried out in the same manner as in Example 1 to obtain 84 g of polypropylene carbonate (yield 82%, molecular weight Mw261000).
  • Example 3 By drying 50 g of the undried zinc catalyst of Example 1 at 90 ° C. and 7.5 mmHg for 4 hours, 30 g of the catalyst having a water content of 513 ppm was obtained. Using this catalyst, polymerization was carried out in the same manner as in Example 1 to obtain 86 g of polypropylene carbonate (yield 84%, molecular weight Mw251000).
  • Example 4 By drying 50 g of the undried zinc catalyst of Example 1 at 90 ° C. and 7.5 mmHg for 8 hours, 29 g of a catalyst having a water content of 408 ppm was obtained. Using this catalyst, polymerization was carried out in the same manner as in Example 1 to obtain 88 g of polypropylene carbonate (yield 86%, molecular weight Mw248000).
  • Example 5 By drying 50 g of the undried zinc catalyst of Example 1 at 70 ° C. and 7.5 mmHg for 4 hours, 30 g of a catalyst having a water content of 1600 ppm was obtained. Using this catalyst, polymerization was carried out in the same manner as in Example 1 to obtain 83 g of polypropylene carbonate (yield 81%, molecular weight Mw312000).
  • Example 6 By drying 50 g of the undried zinc catalyst of Example 1 at 120 ° C. and 7.5 mmHg for 4 hours, 29 g of the catalyst having a water content of 71 ppm was obtained. Using this catalyst, polymerization was carried out in the same manner as in Example 1 to obtain 83 g of polypropylene carbonate (yield 81%, molecular weight Mw220,000).
  • Example 1 The results of the polymerization carried out in Examples 1 to 6 (zinc catalyst water content, polypropylene carbonate molecular weight, and polypropylene carbonate yield) are summarized in Table 1 below.
  • the polymers in Table 1 are polypropylene carbonates.
  • the relationship between the water content of the organozinc catalyst and the molecular weight of polypropylene carbonate is shown in FIG. 1 as a graph.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un moyen pour ajuster le poids moléculaire d'un carbonate de polyalkylène, lors de la réaction d'un dioxyde de carbone avec un époxyde pour obtenir un carbonate de polyalkylène. Plus précisément, l'invention concerne un catalyseur à base d'organate-zinc qui est obtenu par réaction d'un composé du zinc avec un acide carboxylique aliphatique et présente une teneur en eau de 10 à 10 000 ppm.
PCT/JP2020/047341 2020-01-08 2020-12-18 Catalyseur à base d'organate-zinc WO2021140868A1 (fr)

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KR1020227015127A KR20220125214A (ko) 2020-01-08 2020-12-18 유기 아연 촉매

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030134740A1 (en) * 2001-12-18 2003-07-17 Guangzhou Institute Of Chemistry, Chinese Academy Of Sciences Supported catalysts for the fixation of carbon dioxide into aliphatic polycarbonates and a process for preparing the same
JP2008095090A (ja) * 2006-09-15 2008-04-24 Mitsui Chemicals Inc 水崩壊性ブロック共重合体の製造方法、および該方法により得られる水崩壊性ブロック共重合体
JP2012520333A (ja) * 2009-03-16 2012-09-06 バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト 芳香族カルバメートの製造方法
US20130331544A1 (en) * 2008-12-19 2013-12-12 The University Of Sydney Organometallic catalyst and preparation thereof
JP2014009282A (ja) * 2012-06-29 2014-01-20 Nippon Zeon Co Ltd ポリカーボネート化合物および電解質組成物
JP2016535134A (ja) * 2013-11-18 2016-11-10 エルジー・ケム・リミテッド 有機亜鉛触媒、その製造方法およびこれを用いたポリアルキレンカーボネート樹脂の製造方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
JP5514557B2 (ja) 2010-01-08 2014-06-04 株式会社アルバック 非晶質Ｓｉ太陽電池基板の製造方法
CN102869444A (zh) 2010-03-05 2013-01-09 巴斯夫欧洲公司 C4-8-链烷二羧酸的改性锌盐及其用作聚合催化剂的用途

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030134740A1 (en) * 2001-12-18 2003-07-17 Guangzhou Institute Of Chemistry, Chinese Academy Of Sciences Supported catalysts for the fixation of carbon dioxide into aliphatic polycarbonates and a process for preparing the same
JP2008095090A (ja) * 2006-09-15 2008-04-24 Mitsui Chemicals Inc 水崩壊性ブロック共重合体の製造方法、および該方法により得られる水崩壊性ブロック共重合体
US20130331544A1 (en) * 2008-12-19 2013-12-12 The University Of Sydney Organometallic catalyst and preparation thereof
JP2012520333A (ja) * 2009-03-16 2012-09-06 バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト 芳香族カルバメートの製造方法
JP2014009282A (ja) * 2012-06-29 2014-01-20 Nippon Zeon Co Ltd ポリカーボネート化合物および電解質組成物
JP2016535134A (ja) * 2013-11-18 2016-11-10 エルジー・ケム・リミテッド 有機亜鉛触媒、その製造方法およびこれを用いたポリアルキレンカーボネート樹脂の製造方法

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JPWO2021140868A1 (fr) 2021-07-15
KR20220125214A (ko) 2022-09-14

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