WO2024106204A1 - Procédé de production d'acide carboxylique binaphtyle - Google Patents

Procédé de production d'acide carboxylique binaphtyle Download PDF

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WO2024106204A1
WO2024106204A1 PCT/JP2023/039371 JP2023039371W WO2024106204A1 WO 2024106204 A1 WO2024106204 A1 WO 2024106204A1 JP 2023039371 W JP2023039371 W JP 2023039371W WO 2024106204 A1 WO2024106204 A1 WO 2024106204A1
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formula
binaphthyl
bis
represented
carboxymethoxy
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PCT/JP2023/039371
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English (en)
Japanese (ja)
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雅斗 小寺
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本州化学工業株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • 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
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings

Definitions

  • the present invention relates to a method for producing binaphthyl carboxylic acid.
  • it relates to a method for producing 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compounds with good color.
  • polyester resins and polyester carbonate resins using a binaphthyl carboxylic acid component as a polymerization component have been expected to be used as raw materials for optical components such as optical disks, transparent conductive substrates, and optical filters, because they have excellent optical properties such as a high refractive index and low birefringence, and also have high heat resistance.
  • resins produced using 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl hereinafter referred to as "compound A"
  • compound A 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl
  • the present invention was made against the background of the above circumstances, and aims to provide a method for producing binaphthyl carboxylic acid with good hue, which is suitable as a raw material for a resin with excellent optical properties.
  • binaphthyl carboxylic acid with a good hue can be obtained by carrying out the etherification reaction in an atmosphere or airflow with an oxygen concentration of 6% by volume or less, and thus completed the present invention.
  • the present invention is as follows. 1. A method for producing a 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl derivative represented by formula (2), which comprises using a 1,1'-binaphthyl-2,2'-diol derivative represented by formula (1) as a starting material and carrying out the following steps (i) to (iii) in this order: (i): A step of etherifying a 1,1'-binaphthyl-2,2'-diol represented by formula (1) with a halogenated acetate represented by formula (3) in an atmosphere or air stream having an oxygen concentration of 6% by volume or less to produce a 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl represented by formula (4).
  • each R 1 independently represents a linear or branched alkyl group having 1 to 10 carbon atoms, a cyclic alkyl group having 5 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and each m independently represents 0 or an integer of 1 to 4.
  • R 1 and m are defined as in formula (1).
  • X represents a halogen atom
  • R2 represents a linear or branched alkyl group having 1 to 10 carbon atoms.
  • each R 2 is independently defined as in formula (3).
  • a method for producing a 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound according to 1. characterized in that the crystallization in step (iii) is carried out twice.
  • a method for producing a 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound according to 1. characterized in that all of steps (ii) to (iii) are carried out under an atmosphere or flow of an inert gas.
  • the present invention it is possible to obtain binaphthyl carboxylic acid having a good hue.
  • the production method of the present invention is extremely useful in the industrial use of resin raw materials, etc.
  • R 1 in formulas (1), (2), and (4) each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms, a cyclic alkyl group having 5 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms. Among them, a linear or branched alkyl group having 1 to 6 carbon atoms, or an aromatic hydrocarbon group having 6 or 10 carbon atoms is preferred. As the alkyl group, an alkyl group having 1 to 4 carbon atoms is preferred, and an alkyl group having 1 to 2 carbon atoms is more preferred.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a 2-methylpentyl group, and a cyclohexyl group.
  • the aromatic hydrocarbon group having 6 to 10 carbon atoms may be substituted with an alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms includes the number of carbon atoms of the substituted alkyl group, and specific examples include a 4-methylphenyl group, a 4-isopropylphenyl group, a phenyl group, and a naphthyl group.
  • m each independently represents 0 or an integer of 1 to 4. Among these, an integer of 0 or 1 or 2 is preferred.
  • X in formula (3) represents a halogen atom, specifically, for example, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, among which a chlorine atom or a bromine atom is preferred, and a chlorine atom is more preferred.
  • R 2 in formulas (3) and (4) each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms.
  • a linear or branched alkyl group in which the carbon bonded to the oxygen atom is a primary or secondary carbon is preferred, a linear or branched alkyl group in which the carbon is a primary carbon is more preferred, and a linear alkyl group is even more preferred.
  • the alkyl group an alkyl group having 1 to 8 carbon atoms is preferred, an alkyl group having 1 to 4 carbon atoms is more preferred, and an alkyl group having 1 to 2 carbon atoms is even more preferred.
  • Specific examples thereof include a methyl group, an ethyl group, an isopropyl group, an n-propyl group, an isobutyl group, and an n-butyl group.
  • 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound represented by formula (2) which is the final product in the production method of the present invention, include 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl ("compound A"), 2,2'-bis(carboxymethoxy)-6,6'-diphenyl-1,1'-binaphthalene, 2,2'-bis(carboxymethoxy)-3,3'-dimethyl-1,1'-binaphthalene, 2,2'-bis(carboxymethoxy)-4,4'-dimethyl-1,1'-binaphthalene, etc.
  • compound A 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl
  • compound A 2,2'-bis(carboxymethoxy)-6,6'-diphenyl-1,1'-binaphthalene
  • halogenated acetic acid ester represented by formula (3) in the production method of the present invention include, for example, methyl chloroacetate, ethyl chloroacetate, propyl chloroacetate, methyl bromoacetate, ethyl bromoacetate, propyl bromoacetate, methyl iodoacetate, ethyl iodoacetate, propyl iodoacetate, etc.
  • Two or more halogenated acetic acid esters having different R2 moieties in formula (3) may be used in combination, but it is preferable to use one type of halogenated acetic acid ester in order to simplify step (ii).
  • Step (i) in the production method of the present invention is a step of etherifying a 1,1'-binaphthyl-2,2'-diol represented by formula (1) with a halogenated acetate represented by formula (3) in an atmosphere or airflow having an oxygen concentration of 6% by volume or less to produce a 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl represented by formula (4).
  • the oxygen concentration is preferably 5% by volume or less, more preferably 4.5% by volume or less, and even more preferably 4% by volume or less.
  • the atmosphere or airflow having an oxygen concentration of 6% by volume or less may specifically include using an inert gas such as nitrogen, argon, or helium, or using air mixed with an inert gas such as nitrogen gas to have an oxygen concentration of 6% or less.
  • an inert gas such as nitrogen, argon, or helium
  • air mixed with an inert gas such as nitrogen gas to have an oxygen concentration of 6% or less.
  • a mixture of air and an inert gas is preferred, and a mixture of air and nitrogen is more preferred, with the lower limit of the oxygen concentration being preferably 1% by volume or more, and more preferably 2% by volume or more.
  • the halogenated acetate ester represented by formula (3) is preferably used in an amount of 2.1 to 3.0 moles, more preferably 2.2 to 2.8 moles, per mole of the 1,1'-binaphthyl-2,2'-diol represented by formula (1).
  • Such a base is not particularly limited, but alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, etc., alkali metal hydrogen carbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, etc., alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc., as well as organic bases such as triethylamine and pyridine, etc. are preferably used. Among them, sodium carbonate and potassium carbonate are preferable.
  • the amount of the base used is preferably 2.0 to 2.5 times by mole, more preferably 2.05 to 2.15 times by mole, per mole of the 1,1'-binaphthyl-2,2'-diol represented by formula (1).
  • the method for producing a salt of 1,1'-binaphthyl-2,2'-diol represented by formula (1) with a base is preferably to charge the 1,1'-binaphthyl-2,2'-diol represented by formula (1) and the base together with a reaction solvent described below into a reaction vessel, raise the temperature with stirring, and maintain the temperature for about 10 minutes to 1 hour to produce a salt.
  • this salt production method it is more preferable to charge the reaction vessel together with an alkali metal iodide described below to produce a salt.
  • step (i) it is preferable to use a chain or cyclic ketone solvent having 5 to 8 carbon atoms, or a chain nitrile solvent having 2 to 6 carbon atoms.
  • the amount of the solvent used is preferably in the range of 150 to 500 parts by weight, more preferably 200 to 300 parts by weight, relative to 100 parts by weight of the 1,1'-binaphthyl-2,2'-diol represented by formula (1).
  • the reaction temperature in step (i) is preferably in the range of 50 to 130° C., more preferably in the range of 70 to 120° C., and even more preferably in the range of 90 to 110° C.
  • the reaction is usually carried out under normal pressure, but depending on the boiling point of the solvent used, the reaction may be carried out under increased or reduced pressure so that the reaction temperature falls within the above range, but it is preferable to carry out the reaction under normal pressure.
  • the method of forming a salt of 1,1'-binaphthyl-2,2'-diol represented by formula (1) with a base and then reacting the halogenated acetic acid ester represented by formula (3) is preferably a method of forming the salt, followed by dropping the halogenated acetic acid ester represented by formula (3) thereto under stirring at the above reaction temperature, and more preferably, the method of forming the salt by the above method. If the dropping time is too long, the reaction time will be longer accordingly, and if the dropping time is too short, depending on the reaction scale or equipment, it becomes difficult to control the temperature due to heat generation.
  • the dropping time is preferably about 5 minutes to 2 hours, and more preferably 10 minutes to 1 hour.
  • the dropping time is more preferably 20 minutes to 40 minutes, and particularly preferably about 30 minutes, from the viewpoint of the reaction rate.
  • alkali metal iodides In the etherification reaction in step (i) of the production method of the present invention, it is preferable to carry out the reaction in the presence of an alkali metal iodide.
  • the alkali metal iodide include potassium iodide, sodium iodide, cesium iodide, and lithium iodide. These may be used alone or in combination of two or more. Among them, potassium iodide and sodium iodide are preferred.
  • the amount of the alkali metal iodide used is preferably in the range of 1 to 25 mol %, more preferably in the range of 2 to 15 mol %, further preferably in the range of 2.5 to 10 mol %, and particularly preferably in the range of 3 to 5 mol %, based on the 1,1'-binaphthyl-2,2'-diol represented by formula (1).
  • Step (ii) in the production method of the present invention is a step of hydrolyzing the 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl compound represented by formula (4) obtained in step (i) and then treating with an acid.
  • the 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl compound represented by formula (4) used in the hydrolysis reaction in step (ii) the reaction liquid obtained by the etherification reaction in step (i) may be used as it is, or an oil layer obtained by washing the reaction liquid with water may be used, or a solid or crystal extracted from the oil layer or reaction liquid by crystallization or the like may be used.
  • a base In the hydrolysis of the 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl compound represented by formula (4), it is preferable to use a base.
  • the base to be used include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide. By using these, an alkali metal salt of the 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound represented by formula (2) can be obtained.
  • the base to be used may be added to the reaction vessel either as a solid or in the form of an aqueous solution.
  • the concentration is preferably 10 to 60% by weight, more preferably 20 to 50% by weight.
  • the amount of these bases to be used is preferably 2.0 to 6.0 mol, more preferably 2.5 to 4.0 mol, per mol of the 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl compound represented by formula (4).
  • the amount of water used for hydrolysis, including the water contained in the aqueous base solution to be added, is preferably 10 to 200 parts by weight, more preferably 20 to 150 parts by weight, per 100 parts by weight of the 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl compound represented by formula (4).
  • the reaction temperature is usually in the range of 30 to 100° C., preferably in the range of 50 to 90° C., and more preferably in the range of 60 to 80° C., and it is preferable to add or dropwise add the above-mentioned base or an aqueous solution thereof while maintaining this temperature.
  • a reaction solvent may not be used, but is preferably used for reasons such as improved operability and reaction rate during industrial production.
  • the reaction solvent is not particularly limited as long as it is not distilled from the reaction vessel at the reaction temperature and is inactive in the reaction, and examples thereof include chain or cyclic ketone solvents having 5 to 8 carbon atoms, such as diethyl ketone, methyl isobutyl ketone, methyl amyl ketone, 2-octanone, cyclopentanone, and cyclohexanone, and chain nitrile solvents having 2 to 6 carbon atoms, such as acetonitrile and propanenitrile.
  • chain or cyclic ketone solvents having 5 to 8 carbon atoms such as diethyl ketone, methyl isobutyl ketone, methyl amyl ketone, 2-octanone, cyclopentanone, and cyclohexanone
  • chain nitrile solvents having 2 to 6 carbon atoms, such as acetonitrile and propanenitrile.
  • the amount of the solvent used is preferably 100 to 600 parts by weight, more preferably 130 to 400 parts by weight, based on 100 parts by weight of the 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl compound of formula (4).
  • the acid used include inorganic acids such as hydrogen chloride, hydrogen bromide, and sulfuric acid, and organic acids such as p-toluenesulfonic acid, methanesulfonic acid, and trifluoromethanesulfonic acid.
  • Hydrogen chloride is preferably used as concentrated hydrochloric acid.
  • the amount of these acids used is preferably 2.2 to 4.0 mol, and more preferably 2.5 to 3.0 mol, per mol of the 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl compound represented by formula (4) that is the raw material for the hydrolysis reaction.
  • the solvent in the acid treatment is preferably a chain or cyclic ketone solvent, more preferably a chain or cyclic ketone solvent having 5 to 8 carbon atoms, and even more preferably a chain ketone solvent having 5 to 8 carbon atoms.
  • Specific examples include diethyl ketone, methyl isobutyl ketone, methyl amyl ketone, 2-octanone, cyclopentanone, and cyclohexanone.
  • the amount of the solvent used is preferably 250 to 1050 parts by weight, more preferably 350 to 900 parts by weight, relative to 100 parts by weight of the 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl compound represented by formula (4) or 100 parts by weight of the alkali metal salt of the 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound represented by formula (2), which is the raw material for the hydrolysis reaction.
  • the temperature for the acid treatment is usually in the range of 30 to 100°C, preferably in the range of 50 to 90°C, and more preferably in the range of 75 to 85°C.
  • water or a solvent that separates from water as necessary, separate the aqueous layer, and then perform a water washing operation once or a plurality of times in which water is added to the obtained oil layer, the mixture is stirred, allowed to stand, and the aqueous layer is removed, thereby reducing or removing the generated salt and acid from the oil layer.
  • Step (iii) in the production method of the present invention is a step of crystallizing the 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound represented by formula (2) obtained in step (ii).
  • the 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound may be precipitated by crystallizing the oil layer containing the 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound represented by formula (2) obtained in step (ii), or the solvent may be added to and dissolved in the residual liquid obtained by removing the solvent from the oil layer by distillation or the like, or the solvent in the oil layer may be replaced with another solvent and then crystallized.
  • Examples of the solvent used for crystallization include linear or cyclic ketone solvents, cyclic ether solvents, and cyclic ester solvents, with linear or cyclic ketone solvents having 5 to 8 carbon atoms and cyclic ethers or cyclic esters having 4 to 8 carbon atoms being preferred, and linear ketone solvents having 5 to 8 carbon atoms being more preferred.
  • the solvent examples include diethyl ketone, methyl isobutyl ketone, methyl amyl ketone, 2-octanone, cyclopentanone, cyclohexanone, tetrahydrofuran, 1,4-dioxane, ⁇ -butyrolactone, and ⁇ -valerolactone.
  • the amount of the solvent used is preferably 250 to 1000 parts by weight, more preferably 300 to 800 parts by weight, and even more preferably 400 to 600 parts by weight, relative to 100 parts by weight of the 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound represented by formula (2) used in step (iii) in the case of a chain ketone having 5 to 8 carbon atoms.
  • the amount used is preferably 50 to 600 parts by weight, more preferably 50 to 400 parts by weight, and even more preferably 100 to 200 parts by weight, relative to 100 parts by weight of the 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound represented by formula (2) used in step (iii).
  • a solution of the 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound represented by formula (2) dissolved in the above-mentioned solvent or the like is prepared, and the solution is cooled or the solvent is distilled off, or other known methods are used to precipitate crystals of the 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound represented by formula (2).
  • the target product having a good hue can be obtained by crystallizing under the above conditions and filtering off the precipitated crystals. It is more preferable to further crystallize the target product obtained, that is, to carry out the crystallization in step (iii) twice, in order to obtain a target product having a good hue.
  • the crystals obtained by the crystallization in step (iii) are preferably dried.
  • the drying method is not particularly limited, and the crystals may be air-dried at room temperature.
  • the crystals are preferably dried under reduced pressure and/or in an inert gas such as nitrogen. Industrially, the drying is preferably carried out at 70 to 110°C.
  • all steps (ii) to (iii) are preferably carried out in an atmosphere or airflow with an oxygen concentration of 6% by volume or less, preferably 5% by volume or less, more preferably 4.5% by volume or less, and even more preferably 4% by volume or less. It is particularly preferable to carry out the process in an atmosphere or airflow of an inert gas such as nitrogen, argon, or helium in order to obtain a 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl compound represented by formula (2) with a good hue.
  • an inert gas such as nitrogen, argon, or helium
  • Example 1 60 g of 1,1'-binaphthalene-2,2'-diol, 150 g of methyl isobutyl ketone, 60.8 g of potassium carbonate, and 1.2 g of potassium iodide were charged into a four-neck flask, and nitrogen substitution was performed, and the oxygen concentration was confirmed to be 0% by volume using an oxygen concentration meter. The temperature was raised to 100°C, and 60 g of methyl isobutyl ketone was distilled under reduced pressure, and the pressure was returned to nitrogen, and the oxygen concentration was confirmed to be 0% by volume.
  • Example 2 60 g of 1,1'-binaphthalene-2,2'-diol, 150 g of methyl isobutyl ketone, 60.8 g of potassium carbonate, and 1.2 g of potassium iodide were charged into a four-neck flask, and the mixture was replaced with a mixed gas of air and nitrogen with an oxygen concentration of 3.5%, and the oxygen concentration was confirmed to be 4% by volume using an oxygen concentration meter. The temperature was raised to 100°C, and 67 g of methyl isobutyl ketone was distilled under reduced pressure, and the pressure was restored with the above mixed gas, and the oxygen concentration was confirmed to be 4% by volume.
  • a mixed solution of 56.9 g of ethyl chloroacetate and 0.5 g of N-methylpyrrolidone was prepared, and this mixed solution was added dropwise to the reaction solution while maintaining the temperature at 90 to 100°C. After stirring for 10 hours, the oxygen concentration was confirmed to be 4%, and then nitrogen replacement was performed, and the oxygen concentration was confirmed to be 0%. The subsequent operations were performed under a nitrogen gas atmosphere. 240 g of water was added to the reaction solution, and the temperature was raised to 80°C, and the solution was left to stand and the water layer was removed (step i).
  • step iii The mixture was cooled to 30°C at a cooling rate of 10°C per hour and filtered to obtain 79 g of 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl of APHA70 (step iii).
  • step iii Recrystallization of the target product
  • 65 g of the crystals obtained in the above step (iii) 378 g of methyl isobutyl ketone, and 92 g of water were charged into a four-neck flask, and nitrogen replacement was performed, and the oxygen concentration was confirmed to be 0% using an oxygen concentration meter.
  • the subsequent operations were also performed under a nitrogen gas atmosphere. Thereafter, the temperature was raised to 85°C, and the mixture was stirred and dissolved.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention aborde le problème de la fourniture d'un procédé de production d'acide binaphtyle carboxylique qui est approprié en tant que matière première de résine ayant d'excellentes propriétés optiques et qui a une bonne teinte. La présente invention concerne un procédé de production de 2,2'-bis(carboxyméthoxy)-1,1'-binaphtyle représenté par la formule (2), ledit procédé étant caractérisé en ce que le 1,1'-binaphtyl-2,2'-diol représenté par la formule (1) est utilisé en tant que matériau de départ, et les étapes (i) à (iii) sont effectuées dans l'ordre. L'étape (i) qui consiste à réaliser une réaction d'éthérification entre du 1,1'-binaphtyl-2,2'-diol représenté par la formule (1) et un ester d'acide haloacétique représenté par la formule (3) dans une atmosphère ou sous un flux d'air dans lequel la concentration en oxygène n'est pas supérieure à 6 % en volume, ce qui permet de produire du 2,2'-bis(alcoxycarbonylméthoxy)-1,1'-binaphtyle représenté par la formule (4). L'étape (ii) qui consiste à hydrolyser le 2,2'-bis(alcoxycarbonylméthoxy)-1,1'-binaphtyle représenté par la formule (4) et le soumettre ensuite à un traitement acide. L'étape (iii) qui consiste à réaliser une cristallisation pour obtenir du 2,2'-bis(carboxyméthoxy)-1,1'-binaphtyle représenté par la formule (2).
PCT/JP2023/039371 2022-11-18 2023-11-01 Procédé de production d'acide carboxylique binaphtyle WO2024106204A1 (fr)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008024650A (ja) * 2006-07-21 2008-02-07 Okayama Univ 光学活性な大環状化合物、その製造法およびその利用
WO2019230685A1 (fr) * 2018-05-31 2019-12-05 本州化学工業株式会社 Cristal de 2,2'-bis(carboxyméthoxy)-1,1'-binaphtyle
JP2020534350A (ja) * 2017-08-30 2020-11-26 ロイター ヒェミッシャー アパラ—テバウ エー．カー． ビナフチル化合物
WO2021010363A1 (fr) * 2019-07-17 2021-01-21 本州化学工業株式会社 Procédé de production de binaphtyls
WO2021054309A1 (fr) * 2019-09-20 2021-03-25 本州化学工業株式会社 Procédé de production d'un composé biséther aromatique
WO2021107017A1 (fr) * 2019-11-29 2021-06-03 本州化学工業株式会社 Composition de matériau de départ de résine
WO2021107016A1 (fr) * 2019-11-29 2021-06-03 本州化学工業株式会社 Procédé de production d'acide carboxylique binaphtyle

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008024650A (ja) * 2006-07-21 2008-02-07 Okayama Univ 光学活性な大環状化合物、その製造法およびその利用
JP2020534350A (ja) * 2017-08-30 2020-11-26 ロイター ヒェミッシャー アパラ—テバウ エー．カー． ビナフチル化合物
WO2019230685A1 (fr) * 2018-05-31 2019-12-05 本州化学工業株式会社 Cristal de 2,2'-bis(carboxyméthoxy)-1,1'-binaphtyle
WO2021010363A1 (fr) * 2019-07-17 2021-01-21 本州化学工業株式会社 Procédé de production de binaphtyls
WO2021054309A1 (fr) * 2019-09-20 2021-03-25 本州化学工業株式会社 Procédé de production d'un composé biséther aromatique
WO2021107017A1 (fr) * 2019-11-29 2021-06-03 本州化学工業株式会社 Composition de matériau de départ de résine
WO2021107016A1 (fr) * 2019-11-29 2021-06-03 本州化学工業株式会社 Procédé de production d'acide carboxylique binaphtyle

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