WO2023238911A1 - マグネシウム化合物の製造方法 - Google Patents

マグネシウム化合物の製造方法 Download PDF

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WO2023238911A1
WO2023238911A1 PCT/JP2023/021368 JP2023021368W WO2023238911A1 WO 2023238911 A1 WO2023238911 A1 WO 2023238911A1 JP 2023021368 W JP2023021368 W JP 2023021368W WO 2023238911 A1 WO2023238911 A1 WO 2023238911A1
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magnesium
alkyl group
compound
magnesium compound
alcohol
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French (fr)
Japanese (ja)
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大輔 森
義明 鈴木
有理 中山
秀樹 川▲崎▼
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Murata Manufacturing Co Ltd
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Murata Manufacturing Co Ltd
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Priority to CN202380024792.3A priority Critical patent/CN118715232A/zh
Priority to JP2024527016A priority patent/JPWO2023238911A1/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
    • C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
    • 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
    • C07F3/02—Magnesium compounds
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids

Definitions

  • This technology is a method for producing magnesium compounds.
  • magnesium compounds Development of magnesium compounds is progressing, and various studies are being conducted regarding methods for producing the magnesium compounds. Specifically, a method for producing a magnesium compound using magnesium borohydride (Mg(BH 4 ) 2 ) or dibutylmagnesium (Mg(C 4 H 9 ) 2 ) as a starting material has been proposed (for example, (See Patent Document 1.) A magnesium compound produced using this production method is used as an electrolyte salt of an electrolytic solution (see, for example, Patent Document 1).
  • Mg(BH 4 ) 2 magnesium borohydride
  • Mg(C 4 H 9 ) 2 dibutylmagnesium
  • a method for producing a magnesium compound according to an embodiment of the present technology includes mixing metallic magnesium, at least one of alcohol and iodine, a fluorinated alcohol represented by formula (1), and a solvent.
  • a magnesium compound represented by formula (3) is formed by forming a magnesium precursor represented by formula (2) and mixing a solvent containing the magnesium precursor, borane, and a fluorinated alcohol with each other. It is something to do.
  • each of the three R1's is hydrogen, fluorine, an alkyl group, or a fluorinated alkyl group. However, at least one of the three R1's is one of fluorine and a fluorinated alkyl group.
  • each of the six R2's is hydrogen, fluorine, an alkyl group, or a fluorinated alkyl group. However, at least one of the six R2's is one of fluorine and a fluorinated alkyl group.
  • each of the 24 R3's is hydrogen, fluorine, an alkyl group, or a fluorinated alkyl group. However, at least one of the 24 R3's is one of fluorine and a fluorinated alkyl group.
  • metallic magnesium is so-called magnesium alone.
  • the purity of metallic magnesium is not particularly limited, the metallic magnesium may contain any amount of impurities.
  • a magnesium precursor is formed by mixing metallic magnesium, at least one of alcohol and iodine, a fluorinated alcohol, and a solvent, and then Since a magnesium compound is formed by mixing a solvent containing a magnesium precursor, borane, and a fluorinated alcohol, the magnesium compound can be easily and stably produced.
  • the method for producing a magnesium compound described here is a method for producing a magnesium compound represented by formula (3) described below, and more specifically, a method for producing a magnesium compound using metallic magnesium as a starting material. It is.
  • this magnesium compound contains a magnesium ion (Mg 2+ ) as a cation and a boron-containing ion ([B(OC(R3) 3 ) 4 ] - ) as an anion. It is a magnesium salt that contains
  • the use of the magnesium compound is not particularly limited, but specifically, it is used as an electrolyte for magnesium batteries.
  • a magnesium compound is used as the electrolyte salt.
  • FIG. 1 shows the flow of the manufacturing procedure in order to explain the method for manufacturing a magnesium compound according to the first embodiment. Below, the manufacturing procedure of a magnesium compound will be explained with reference to FIG.
  • magnesium alone is used instead of magnesium compounds such as magnesium borohydride and dibutylmagnesium.
  • metal magnesium, alcohol, fluorinated alcohol, borane, and a solvent are prepared as raw materials.
  • metallic magnesium is magnesium alone, and may contain any amount of impurities.
  • the content of this impurity is preferably as low as possible. This is because magnesium compounds are more likely to be formed.
  • Alcohol is a catalyst for promoting the dissolution reaction of magnesium metal.
  • This alcohol unlike fluorinated alcohol, is a compound that does not contain fluorine as a constituent element.
  • the type of alcohol is not particularly limited as long as it is one or more types of arbitrary alcohols. Specific examples of alcohols include methanol, ethanol and propanol. Note that the alcohol such as propanol having three or more carbon atoms may be chain-like or branched.
  • the alcohol contains methanol. This is because the dissolution reaction of magnesium metal progresses more easily, and a magnesium compound is more likely to be formed.
  • Fluorinated alcohol is a material that serves as a source of fluorine-containing groups (-OC(R3) 3 ) contained in magnesium compounds.
  • This fluorinated alcohol is a compound that contains fluorine as a constituent element, unlike alcohol. That is, a fluorinated alcohol is a compound in which one or more hydrogen atoms in an alcohol are replaced with fluorine, and more specifically, any one of the compounds represented by formula (1) Contains one or more types.
  • each of the three R1's is hydrogen, fluorine, an alkyl group, or a fluorinated alkyl group. However, at least one of the three R1's is one of fluorine and a fluorinated alkyl group.
  • this fluorinated alcohol is a compound in which one or more hydrogen atoms in the alcohol are replaced with fluorine. Accordingly, a compound in which all three R1's are either hydrogen or an alkyl group does not fall under the category of fluorinated alcohol as described herein.
  • the number of carbon atoms in the alkyl group is not particularly limited. Further, the type of alkyl group may be linear or branched. Specific examples of alkyl groups include methyl and ethyl groups. Among these, the alkyl group is preferably a methyl group. This is because the compatibility of fluorinated alcohols is improved.
  • a fluorinated alkyl group is a group in which one or more hydrogens in an alkyl group are substituted with fluorine.
  • the number of fluorines contained in the fluorinated alkyl group is not particularly limited.
  • fluorinated alcohols include (CF 3 ) 2 HCOH, (CF 3 ) 3 COH, (CH 3 )(CF 3 )HCOH, (CH 3 ) , as described later in relation to specific examples of magnesium compounds.
  • the fluorinated alcohol preferably contains (CF 3 ) 2 HCOH, which is hexafluoroisopropanol (hexafluoro-2-propanol). This is because magnesium compounds are more likely to be formed.
  • B boron
  • boron is the central element of the anion (boron-containing ion) contained in the magnesium compound.
  • the solvent contains one or more organic solvents that can dissolve metal magnesium.
  • the solvent contains an ether compound. This is because metallic magnesium is stably dissolved.
  • This ether compound is a compound having an ether bond (-O-), and may be a chain compound, a cyclic compound, or both.
  • ether compounds include dimethoxyethane, diethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and tetrahydrofuran. This is because metallic magnesium is sufficiently dissolved.
  • Specific examples of the series of ether compounds described here are mainly so-called glyme-based ethers.
  • the ether compound contains one or both of dimethoxyethane and tetrahydrofuran, since metallic magnesium is better dissolved therein.
  • Step S102 metal magnesium, alcohol, fluorinated alcohol, and a solvent are mixed with each other (step S102).
  • the solvent may be stirred using a stirring device or the like.
  • each of the six R2's is hydrogen, fluorine, an alkyl group, or a fluorinated alkyl group. However, at least one of the six R2's is one of fluorine and a fluorinated alkyl group.
  • This magnesium precursor is an intermediate product used to synthesize a magnesium compound, and as is clear from formula (2), a magnesium atom is bonded to two fluorine-containing groups (-OC(R2) 3 ). It is a compound that has been Accordingly, a compound in which all six R2's are either hydrogen or an alkyl group does not fall under the magnesium precursor described herein.
  • Chemical reaction A progresses at room temperature, and in chemical reaction A, magnesium methoxide (Mg(CH 3 O) 2 ) is synthesized.
  • Mg(CH 3 O) 2 magnesium methoxide
  • the solubility of magnesium methoxide in alcohol (CH 3 OH) is low, as chemical reaction A progresses, the reaction rate of chemical reaction A decreases. This is because, due to the presence of magnesium methoxide having low solubility, the magnesium methoxide coats the surface of metal magnesium (Mg) and the stirring efficiency of the solvent containing the magnesium methoxide decreases.
  • magnesium precursor synthesis step not only chemical reactions A and B proceed, but also chemical reaction C.
  • this chemical reaction C unlike chemical reactions A and B, a magnesium precursor is directly synthesized from metallic magnesium without going through magnesium methoxide.
  • the reaction rate of chemical reaction C at room temperature is lower than the reaction rate of each of chemical reactions A and B. In this case, the reaction rate becomes lower due to the formation of an oxide film on the surface of the metal magnesium, so that the progress of the chemical reaction C is inhibited.
  • magnesium precursor synthesis process in chemical reactions A and B, a magnesium precursor is indirectly synthesized using metallic magnesium as a starting material, and in chemical reaction C, magnesium precursor is synthesized indirectly using metallic magnesium as a starting material. Precursors are synthesized directly.
  • a solvent containing a magnesium precursor, borane, and a fluorinated alcohol are mixed with each other (step S104).
  • the solvent may be stirred using a stirring device or the like.
  • the magnesium precursor reacts with each of borane and fluorinated alcohol in the solvent, so that the magnesium compound shown in formula (3) is synthesized (step S105).
  • each of the 24 R3's is hydrogen, fluorine, an alkyl group, or a fluorinated alkyl group. However, at least one of the 24 R3's is one of fluorine and a fluorinated alkyl group.
  • this magnesium compound is a compound in which a magnesium atom is bonded to two boron-containing groups (-B(OC(R3) 3 ) 4 ). Therefore, a compound in which all 24 R3's are either hydrogen or an alkyl group does not fall under the magnesium compound described here.
  • this magnesium compound is thereby obtained.
  • this magnesium compound is a magnesium salt containing a magnesium ion (Mg 2+ ) as a cation and a boron-containing ion ([B(OC(R3) 3 ) 4 ] - ) as an anion. It is.
  • Mg[B(OCH( CF3 ) 2 ) 4 ] 2 is synthesized as a magnesium compound by using hexafluoroisopropanol (( CF3 ) 2HCOH ) as a fluorinated alcohol. This is a chemical reaction in case.
  • a magnesium precursor (Mg[OCH( CF3 ) 2 ] 2 ) reacts with borane ( BH3 ) and a fluorinated alcohol (( CF3 ) 2HCOH ).
  • a magnesium compound (Mg[B(OCH(CF 3 ) 2 ) 4 ] 2 ) is synthesized.
  • composition of the magnesium compound produced by the above production procedure is determined depending on the composition of the fluorinated alcohol used in the production procedure.
  • composition of the fluorinated alcohol the composition of the magnesium precursor, and the composition of the magnesium compound is as follows.
  • Mg[OCH(CF 3 ) 2 ] 2 is formed as a magnesium precursor, and Mg[B(OCH(CF 3 ) 2 ] 2 is formed as a magnesium compound. ) 4 ] 2 is manufactured.
  • Mg[OC(CF 3 ) 3 ] 2 is formed as a magnesium precursor, and Mg[B(OC(CF 3 ) 3 ) 3 is formed as a magnesium compound. ) 4 ] 2 is manufactured.
  • Mg[OCH(CF 3 )(CH 3 )] 2 is formed as a magnesium precursor, and Mg[B( OCH( CF3 )( CH3 )) 4 ] 2 is produced.
  • Mg[OC(CF 3 )(CH 3 ) 2 ] 2 is formed as a magnesium precursor, and Mg[OC(CF 3 )(CH 3 ) 2 ] 2 is formed as a magnesium compound.
  • B(OC( CF3 )(CH3 )2 ) 4 ] 2 is produced.
  • a magnesium precursor is formed by mixing metallic magnesium, an alcohol, a fluorinated alcohol, and a solvent, and then a solvent containing the magnesium precursor and borane are mixed together.
  • a magnesium compound is formed by mixing the fluorinated alcohols with each other.
  • a magnesium compound is synthesized using chemically stable elemental magnesium (metallic magnesium) as a starting material, without using a chemically unstable magnesium compound as a starting material.
  • chemically unstable magnesium compound include the above-mentioned magnesium borohydride and dibutylmagnesium.
  • the magnesium compound is easily and stably synthesized, the magnesium compound can be easily and stably obtained. In this case, since it is not necessary to use an expensive magnesium compound as a starting material, a large amount of magnesium compound can be obtained at low cost.
  • the fluorinated alcohol contains hexafluoroisopropanol, a magnesium compound is more likely to be formed, so higher effects can be obtained.
  • the alcohol contains methanol, magnesium compounds are more likely to be formed, so higher effects can be obtained.
  • the magnesium compound will be stably dissolved, so higher effects can be obtained.
  • the ether compound contains one or both of dimethoxyethane and tetrahydrofuran, the magnesium compound will be sufficiently dissolved, and even higher effects can be obtained.
  • the content of the method for producing a magnesium compound in the second embodiment is the same as the content of the method for producing a magnesium compound in the first embodiment, except that iodine (I 2 ) is used instead of alcohol. Like alcohol, this iodine is a catalyst for promoting the dissolution reaction of metal magnesium.
  • FIG. 2 shows the flow of the manufacturing procedure for explaining the method for manufacturing a magnesium compound according to the second embodiment, and corresponds to FIG. 1. Below, the manufacturing procedure of a magnesium compound will be explained with reference to FIG.
  • metal magnesium is used instead of a magnesium compound as a source of magnesium contained in the magnesium compound.
  • metal magnesium, iodine, fluorinated alcohol, borane, and a solvent are prepared as raw materials. Details regarding each of the magnesium metal, the fluorinated alcohol, and the solvent are as described above.
  • step S202 metal magnesium, iodine, fluorinated alcohol, and a solvent are mixed with each other (step S202).
  • the solvent may be stirred using a stirring device or the like.
  • a magnesium precursor is synthesized (step S203). Details regarding the magnesium precursor are as described above.
  • the chemical reaction E described here is the chemistry in which Mg[OCH(CF 3 ) 2 ] 2 is synthesized as a magnesium precursor by using hexafluoroisopropanol ((CF 3 ) 2 HCOH) as a fluorinated alcohol. It is a reaction.
  • Chemical reaction E progresses at room temperature, and in chemical reaction E, magnesium iodide (MgI 2 ) is synthesized. Further, the chemical reaction C described above proceeds.
  • magnesium metal Mg
  • chemical reaction E the oxide film formed on the surface of metallic magnesium is dissolved, so that the surface (active surface) of metallic magnesium is easily exposed. This promotes the chemical reaction C, so that a magnesium precursor (Mg[OCH(CF 3 ) 2 ] 2 ) is synthesized in the chemical reaction C.
  • a solvent containing a magnesium precursor, borane, and a fluorinated alcohol are mixed with each other (step S204).
  • the solvent may be stirred using a stirring device or the like.
  • the magnesium precursor reacts with each of borane and fluorinated alcohol in the solvent, so that a magnesium compound is synthesized (step S205).
  • a magnesium compound is obtained.
  • composition of the magnesium compound produced by the above production procedure is determined depending on the composition of the fluorinated alcohol used in the production procedure.
  • the relationship among the composition of the fluorinated alcohol, the composition of the magnesium precursor, and the composition of the magnesium compound is as explained in the first embodiment.
  • a magnesium precursor is formed by mixing metallic magnesium, iodine, a fluorinated alcohol, and a solvent, and then a magnesium precursor is formed by mixing a solvent containing the magnesium precursor with borane.
  • a magnesium compound is formed by mixing the fluorinated alcohols with each other.
  • the magnesium compound is easily and stably produced, the magnesium compound can be easily and stably obtained.
  • alcohol was used as a catalyst to promote the dissolution reaction of metal magnesium.
  • iodine was used as a catalyst for promoting the dissolution reaction of metal magnesium.
  • both alcohol and iodine may be used. In this case as well, the same effect can be obtained because the magnesium compound is easily and stably produced.
  • a secondary battery used as a power source may be a main power source or an auxiliary power source in electronic devices, electric vehicles, and the like.
  • the main power source is a power source that is used preferentially, regardless of the presence or absence of other power sources.
  • the auxiliary power source may be a power source used in place of the main power source, or may be a power source that can be switched from the main power source.
  • magnesium batteries are as described below.
  • Electronic devices such as video cameras, digital still cameras, mobile phones, notebook computers, headphone stereos, portable radios, and portable information terminals.
  • Backup power supplies and storage devices such as memory cards.
  • Power tools such as power drills and power saws. This is a battery pack installed in electronic devices.
  • Medical electronic devices such as pacemakers and hearing aids.
  • Electric vehicles such as electric vehicles (including hybrid vehicles).
  • a power storage system such as a household or industrial battery system that stores power in case of an emergency. In these applications, one magnesium battery or multiple magnesium batteries may be used.
  • the battery pack may use single cells or assembled batteries.
  • the electric vehicle is a vehicle that runs using a magnesium battery as a power source for driving, and may also be a hybrid vehicle that also includes a drive source other than the magnesium battery.
  • a home power storage system it is possible to use the power stored in a magnesium battery, which is a power storage source, to power home appliances and the like.
  • a magnesium compound was produced by the procedure described below.
  • Example 1 The magnesium compound was manufactured using the method for manufacturing a magnesium compound in the first embodiment.
  • solution X was dried under reduced pressure to recover the magnesium precursor.
  • the magnesium precursor (0.01 mol) was added to 20 cm 3 of the solvent (dimethoxyethane, which is an ether compound), and the solvent was stirred to prepare a solution Y in which the magnesium precursor was dissolved. .
  • Example 2 The magnesium compound was manufactured using the method for manufacturing a magnesium compound in the second embodiment.
  • iodine (I 2 ) was added to a solvent (tetrahydrofuran, which is an ether compound), and the solvent was stirred to prepare an iodine solution in tetrahydrofuran.
  • the magnesium precursor When evaluating a magnesium precursor, the magnesium precursor was added to a solvent, and then the solvent was stirred. As a result, the magnesium precursor was dissolved in the solvent, so a sample for analysis was obtained.
  • a dimethylsulfoxide-d 6 solution LiTFSI DMSO-d 6 ) of bis(trifluoromethanesulfonyl)imide lithium (LiN(CF 3 SO 2 ) 2 ) was used. After this, the sample was analyzed using proton nuclear magnetic resonance ( 1H NMR).
  • Example 1 In the results of analysis of the magnesium precursor using proton nuclear magnetic resonance, a peak due to a fluorine-containing group (-OCH(CF 3 ) 2 ) was detected at 8.0 ppm (reference material: tetramethylsilane). This confirmed that a magnesium precursor (Mg(OCH(CF 3 ) 2 ) 2 ) was synthesized. In this case, it was also confirmed that alcohol (methanol) and solvents (dimethoxyethane and tetrahydrofuran) each existed as a crystallization solvent or coordination solvent.
  • Example 2 Evaluation results similar to those of Example 1 were obtained. As a result, a magnesium precursor (Mg(OCH(CF 3 ) 2 ) 2 ) 2 ) was synthesized, and a magnesium compound (Mg[B(OCH(CF 3 ) 2 ) 4 ] 2 ) was synthesized. confirmed.
  • Example 2 As described above, since hydrogen was generated due to the reaction of metallic magnesium, it was confirmed that the metallic magnesium was reacting with the fluorinated alcohol (hexafluoroisopropanol). This result also confirmed that a magnesium compound was synthesized via a magnesium precursor.
  • magnesium compound is used in a magnesium battery
  • the use of the magnesium compound is not particularly limited. Therefore, magnesium compounds can be widely used in applications other than magnesium batteries.
  • a magnesium precursor represented by formula (2) is formed by mixing metallic magnesium, at least one of alcohol and iodine, a fluorinated alcohol represented by formula (1), and a solvent. , Forming a magnesium compound represented by formula (3) by mixing the solvent containing the magnesium precursor, borane, and the fluorinated alcohol with each other; A method for producing a magnesium compound.
  • R1 3COH ...(1) Each of the three R1's is hydrogen, fluorine, an alkyl group, or a fluorinated alkyl group. However, at least one of the three R1's is one of fluorine and a fluorinated alkyl group.
  • each of the six R2's is hydrogen, fluorine, an alkyl group, or a fluorinated alkyl group. However, at least one of the six R2's is one of fluorine and a fluorinated alkyl group.
  • Mg[B(OC(R3) 3 ) 4 ] 2 ...(3) (Each of the 24 R3's is hydrogen, fluorine, an alkyl group, or a fluorinated alkyl group. However, at least one of the 24 R3's is one of fluorine and a fluorinated alkyl group.
  • the fluorinated alcohol includes hexafluoroisopropanol.
  • the alcohol includes methanol, A method for producing a magnesium compound according to ⁇ 1> or ⁇ 2>.
  • the solvent contains an ether compound having an ether bond (-O-), A method for producing a magnesium compound according to any one of ⁇ 1> to ⁇ 3>.
  • the ether compound contains at least one of dimethoxyethane and tetrahydrofuran. The method for producing a magnesium compound according to ⁇ 4>.

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Citations (2)

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US20160294010A1 (en) * 2015-03-31 2016-10-06 The Trustees Of Princeton University Electrolytes for magnesium-ion batteries
JP2021178801A (ja) * 2020-05-15 2021-11-18 国立研究開発法人物質・材料研究機構 ホウ素系マグネシウム塩の製造方法、電解液の製造方法、ホウ素系マグネシウム塩、電解液、及び、二次電池

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EP3975303A4 (en) * 2019-05-22 2022-08-24 Panasonic Intellectual Property Management Co., Ltd. ANHYDROUS ELECTROLYTE SOLUTION FOR MAGNESIUM SECONDARY BATTERY AND MAGNESIUM SECONDARY BATTERY WITH IT

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US20160294010A1 (en) * 2015-03-31 2016-10-06 The Trustees Of Princeton University Electrolytes for magnesium-ion batteries
JP2021178801A (ja) * 2020-05-15 2021-11-18 国立研究開発法人物質・材料研究機構 ホウ素系マグネシウム塩の製造方法、電解液の製造方法、ホウ素系マグネシウム塩、電解液、及び、二次電池

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