WO2021015083A1 - Cristal de 2, 2'-bis(éthoxycarbonylméthoxy)-1, 1'-binaphtyle - Google Patents

Cristal de 2, 2'-bis(éthoxycarbonylméthoxy)-1, 1'-binaphtyle Download PDF

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Publication number
WO2021015083A1
WO2021015083A1 PCT/JP2020/027640 JP2020027640W WO2021015083A1 WO 2021015083 A1 WO2021015083 A1 WO 2021015083A1 JP 2020027640 W JP2020027640 W JP 2020027640W WO 2021015083 A1 WO2021015083 A1 WO 2021015083A1
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crystal
bis
crystals
ethoxycarbonylmethoxy
binaphthyl
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PCT/JP2020/027640
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English (en)
Japanese (ja)
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大地 佐久間
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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
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708—Ethers
    • C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring

Definitions

  • the present invention relates to a novel crystal of a dicarboxylic acid ethyl ester compound.
  • polyester resins and polyester carbonate resins having a diester component having a binaphthalene skeleton as a polymerization component are excellent in optical properties such as high refractive index and low birefringence, and have high heat resistance. It is expected as a raw material for optical members such as sex substrates and optical filters. Among them, 2,2'-bis (ethoxycarbonylmethoxy) -1,1'-binaphthyl (hereinafter, may be referred to as "Compound A”) having a chemical structure represented by the following chemical formula is produced as a polymerization component. Resins are particularly attracting attention as having excellent optical properties (for example, Patent Documents 1 to 3 and the like).
  • 1,1'-binaphthalene-2,2'- A method of reacting a diol with a halogenated acetate such as ethyl chloroacetate is known (for example, Patent Document 4 and the like).
  • a halogenated acetate such as ethyl chloroacetate
  • the 2,2'-bis (ethoxycarbonylmethoxy) -1,1'-binaphthyl obtained by the reaction is converted into a derivative such as a dicarboxylic acid or an acid chloride as a crude product without purification. Often used. Therefore, it is preferable to purify the intermediate 2,2'-bis (ethoxycarbonylmethoxy) -1,1'-binaphthyl, and a crystal having good handleability is desired.
  • the present invention has been made in the context of the above circumstances, and provides a crystal of 2,2'-bis (ethoxycarbonylmethoxy) -1,1'-binaphthyl, which is suitable as a resin raw material having excellent optical properties. Make it an issue.
  • the present inventors have conducted powder X-ray diffraction with Cu—K ⁇ rays, which has a crystal body of compound A, particularly an endothermic peak top temperature in a specific range by differential scanning calorific analysis. A crystal of compound A having a specific peak in the peak pattern or having a loose bulk density in a specific range was found, and the present invention was completed.
  • the present invention is as follows. Crystals of 1.2,2'-bis (ethoxycarbonylmethoxy) -1,1'-binaphthyl. 2. 2. 1. The endothermic peak top temperature by differential scanning calorimetry is in the range of 107 to 113 ° C. 2,2'-Bis (ethoxycarbonylmethoxy) -1,1'-binaphthyl crystal described in 1. 3. 3. In the powder X-ray diffraction peak pattern by Cu-K ⁇ rays, the diffraction angles 2 ⁇ are 10.0 ⁇ 0.2 °, 17.7 ⁇ 0.2 °, 19.3 ⁇ 0.2 °, 21.0 ⁇ 0. 1.
  • the crystal of the present invention in the production of compound A, it becomes possible to stably obtain a crystal having good handleability, which is very useful for industrial production.
  • the crystal of the present invention has a high melting point, so that it has excellent storage stability and does not block.
  • the crystal of the present invention since the crystal of the present invention has a large loose bulk density, the amount of the compound that can be obtained per production can be increased, and the transportation efficiency is also improved, which is advantageous for industrial production.
  • the crystal of the present invention has improved solvent solubility as compared with 2,2'-bis (carboxymethoxy) -1,1'-binaphthyl, 2,2'-bis (carboxymethoxy) -1 , 1'-In the production using binaphthyl as a starting material, more efficient production becomes possible, which is industrially advantageous. That is, the provision of the crystals of the present invention is very useful in industrial use.
  • FIG. 1 It is a chart figure which shows the differential scanning calorimetry data of the crystal obtained in Example 1.
  • FIG. It is a chart figure which shows the powder X-ray diffraction data by the Cu—K ⁇ ray of the crystal obtained in Example 1.
  • FIG. It is a chart figure which shows the differential scanning calorimetry data of the crystal obtained in Example 2.
  • FIG. It is a chart figure which shows the differential scanning calorimetry data of the crystal obtained in Example 3.
  • FIG. It is a chart figure which shows the differential scanning calorimetry data of the crystal obtained in Example 4.
  • FIG. It is a chart figure which shows the powder X-ray diffraction data by the Cu—K ⁇ ray of the crystal obtained in Example 4.
  • the compound A according to the crystal of the present invention is a compound represented by the following chemical formula.
  • the method for synthesizing the compound A according to the crystal of the present invention is not particularly limited, but for example, in the presence of a base, halogenation of known 1,1'-binaphthalene-2,2'-diol and ethyl chloroacetate or the like Examples thereof include a production method of reacting with ethyl acetate.
  • ethyl halide examples include ethyl chloroacetate, ethyl bromoacetate, and ethyl iodoacetate, and among them, ethyl chloroacetate or ethyl bromoacetate is preferable.
  • the amount of ethyl halide acetate used is not particularly limited as long as it is a theoretical value (2.0) or more as the charged molar ratio to 1,1'-binaphthalene-2,2'-diol, but it is usually used. It is used in the range of 2 to 20 times molar amount, preferably in the range of 2 to 10 times molar amount, and more preferably in the range of 2 to 6 times molar amount.
  • the reaction is carried out in the presence of a base, and examples of the base used include triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate and the like. Of these, sodium carbonate and potassium carbonate are preferable.
  • the molar ratio of the base charged is usually in the range of 0.8 to 4 times the molar amount, preferably in the range of 0.85 to 3 times the molar amount, and more preferably 0.9 to 2 times the molar amount with respect to ethyl halide. It is a range of quantities.
  • a catalyst may be used, for example, alkali metal bromide salts such as sodium bromide and potassium bromide, alkali metal iodide salts such as sodium iodide and potassium iodide, ammonium bromide, ammonium iodide and the like. Can be mentioned.
  • the amount of the catalyst used is usually in the range of 0.1 to 100% by weight, preferably in the range of 0.1 to 20% by weight, more preferably 0, based on 1,1'-binaphthalene-2,2'-diol. It is in the range of 1 to 10% by weight.
  • reaction solvent is not particularly limited as long as it is not distilled out from the reaction vessel at the reaction temperature and is inactive in the reaction.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, tetrahydrofuran and 1,4-dioxane.
  • Ethers such as 1,3-dioxane and diethoxyethane
  • aprotic polar solvents such as acetonitrile, dimethyl sulfoxide, dimethylformamide and N-methylpyrrolidone.
  • organic solvents may be used alone, or two or more of them may be used in combination as appropriate to adjust the polarity.
  • methyl isobutyl ketone and acetonitrile are preferable.
  • the reaction temperature is usually in the range of 25 to 120 ° C., preferably in the range of 40 to 110 ° C., more preferably in the range of 50 to 100 ° C.
  • reaction temperature is high, the yield will decrease due to hydrolysis of the produced ester compound, and if the reaction temperature is low, the reaction rate will be slow, which is not preferable.
  • the reaction pressure is usually carried out under normal pressure, but depending on the boiling point of the organic solvent used, the reaction pressure may be carried out under pressure or reduced pressure so that the reaction temperature is within the above range.
  • the end point of the reaction can be confirmed by liquid chromatography or gas chromatography analysis. It is preferable that the end point of the reaction is the time when the unreacted 1,1'-binaphthalene-2,2'-diol disappears and the increase of the target substance is no longer observed.
  • the reaction time varies depending on the reaction conditions such as the reaction temperature, but is usually completed in about 1 to 30 hours.
  • the target compound A After completion of the etherification reaction, it is preferable to purify and isolate the target compound A from the reaction product mixture.
  • a conventional method after completion of the reaction, neutralization, washing with water, crystallization, filtration, distillation, column chromatography Compound A can be obtained by performing a post-treatment operation such as separation by.
  • purification by distillation, recrystallization or column chromatography may be carried out according to a conventional method.
  • the step of crystallizing the compound A obtained by the etherification reaction will be described in detail.
  • the compound A used in the crystallization step include crude crystals obtained by treating the reaction solution, recrystallized crystals of the crude crystals, and a residue obtained by distilling off the solvent from the solution containing the compound A. It may be amorphous.
  • Solvents that can be used for crystallization include, for example, aromatic hydrocarbons such as toluene, xylene and benzene, aliphatic hydrocarbons having 5 or more carbon atoms such as hexane, heptane and cyclohexane, and total carbon number 3 such as acetone.
  • the solvent used for crystallization includes a chain aliphatic ketone solvent having 5 to 8 carbon atoms, a mixed solvent of a chain aliphatic ketone having 3 or 4 carbon atoms and water, and a solvent having 1 to 4 carbon atoms.
  • any of an aliphatic alcohol solvent and a mixed solvent of a monocyclic aromatic hydrocarbon having 6 to 10 carbon atoms and an aliphatic hydrocarbon having 5 to 8 carbon atoms (chain or cyclic) is preferable.
  • the amount of the solvent that can be used for crystallization will be described below.
  • the range of 80 to 500 parts by weight is preferable, and the range of 100 to 300 parts by weight is more preferable with respect to 100 parts by weight of the compound A contained in the crude crystal or the like.
  • the mixed solvent of the chain aliphatic ketone having 3 or 4 carbon atoms and water is preferably in the range of 100 to 500 parts by weight, preferably 120 to 300 parts by weight, based on 100 parts by weight of the compound A contained in the crude crystal or the like.
  • the range is more preferable, and the concentration of the chain aliphatic ketone in the mixed solvent is preferably in the range of 65 to 85% by weight, more preferably in the range of 70 to 80% by weight.
  • the aliphatic alcohol solvent having 1 to 4 carbon atoms the range of 700 to 3000 parts by weight is preferable, and the range of 800 to 2000 parts by weight is more preferable with respect to 100 parts by weight of the compound A contained in the crude crystals and the like.
  • a mixed solvent of a monocyclic aromatic hydrocarbon having 6 to 10 carbon atoms and an aliphatic hydrocarbon having 5 to 8 carbon atoms 100 to 1000 parts by weight with respect to 100 parts by weight of compound A contained in crude crystals or the like.
  • the range of 150 to 500 parts by weight is more preferable, and the concentration of the aliphatic hydrocarbon in the mixed solvent is preferably in the range of 50 to 90% by weight, more preferably in the range of 60 to 80% by weight.
  • the rate at which compound A is dissolved in the solvent and then cooled is preferably 10 to 20 ° C., more preferably 13 to 17 ° C. per hour.
  • the temperature at which the crystals are precipitated is preferably 30 to 85 ° C, more preferably 35 to 75 ° C, and particularly preferably 40 to 65 ° C.
  • the final cooling temperature is preferably 15 to 60 ° C, more preferably 20 to 50 ° C.
  • the precipitated crystals are separated by a filtration operation.
  • the solvent used in crystallization can be removed. This drying can be carried out on the crystals obtained by crystallization, preferably at 50 to 105 ° C. under reduced pressure, and more preferably at 60 to 100 ° C. under reduced pressure. Drying may be carried out under normal pressure or reduced pressure, but when carried out industrially, it is more efficient to carry out under reduced pressure because the solvent used in crystallization can be removed.
  • the endothermic peak top temperature by differential scanning calorimetry is in the range of 107 to 113 ° C.
  • crystals having the endothermic peak top temperature in the range of 108 to 112 ° C. are preferable, crystals in the range of 110 to 112 ° C. are more preferable, and crystals in the range of 111 to 112 ° C. are most preferable.
  • the crystal of the present invention has a diffraction angle of 2 ⁇ of 10.0 ⁇ 0.2 °, 17.7 ⁇ 0.2 °, 19.3 ⁇ 0. In the powder X-ray diffraction peak pattern by Cu—K ⁇ ray.
  • the crystal of the present invention is characterized in that the loose bulk density is in the range of 0.3 to 0.7 g / cm 3 .
  • the loose bulk density of the present invention is generally measured by uniformly charging the granules to be measured into the container without forming a cavity in a container having a constant volume and without applying an external force such as vibration to the container. It means the value measured by dividing the weight by the container volume, for example, using a multifunctional powder physical property measuring instrument Multitester (MT-1001 type / manufactured by Seishin Co., Ltd.) or the like.
  • the loose bulk density of the crystal of the present invention is preferably in the range of 0.3 to 0.7 g / cm 3 .
  • the lower limit value in this numerical range is preferably 0.4 g / cm 3 or more, more preferably 0.5 g / cm 3 or more, and particularly preferably 0.55 g / cm 3 or more.
  • the upper limit value in this numerical range is preferably a numerical value closer to 0.6 g / cm 3 .
  • the loose bulk density of the crystal of the present invention is particularly preferably in the range of 0.55 g / cm 3 to 0.60 g / cm 3 .
  • the crystal of the present invention can suppress dust, prevent adhesion to manufacturing equipment and clogging, and can reduce the capacity of the reaction vessel when used as a reaction raw material and the vessel during transportation, thus improving productivity. It exerts excellent effects in terms of operability, such as being able to reduce transportation costs.
  • DSC Differential scanning calorimetry
  • the crystals were precisely weighed in an aluminum pan, and measured using a differential scanning calorimetry device (manufactured by Shimadzu Corporation: DSC-60) under the following operating conditions using aluminum oxide as a control. (Operating conditions) Heating rate: 10 ° C / min Measurement temperature range: 30-200 ° C Measurement atmosphere: open, nitrogen 50 mL / min Sample amount: 3 mg ⁇ 1 mg 2. 2.
  • Powder X-ray diffraction (XRD) 0.1 g of the crystal was filled in the sample filling portion of the glass test plate, and the measurement was carried out under the following conditions using a powder X-ray diffractometer (manufactured by Rigaku Co., Ltd .: SmartLab).
  • Example 1 Crystal of Compound A 30.0 g of crude crystals, 20 g of toluene, and 55 g of cyclohexane obtained in the above synthesis example were placed in a four-necked flask and heated to 70 ° C. to dissolve them. After washing the oil layer with water, the oil layer was cooled to 25 ° C. at a cooling rate of 15 ° C./hour, and seed crystals were added at 60 ° C. on the way to precipitate crystals. The crystals were separated by filtration and dried to obtain 23.5 g of crystals of the target compound A.
  • the endothermic peak top temperature by differential scanning calorimetry was 112.0 ° C., and the loose bulk density was 0.53 g / cm 3 .
  • the characteristic diffraction angle 2 ⁇ (deg, peak with relative integral intensity of 10 or more) in the powder X-ray diffraction peak pattern by Cu—K ⁇ rays is 10.0, 11.6, 15.4, 17.7. , 19.3, 20.1, 20.9, 22.1, 23.3, 24.3, 26.8, 27.0.
  • FIG. 1 shows a chart showing the differential scanning calorific value analysis data of the obtained crystal
  • FIG. 2 shows a chart showing the powder X-ray diffraction data by Cu—K ⁇ rays.
  • Example 2 Crystal of Compound A 30.0 g of crude crystals and 45 g of methyl isobutyl ketone obtained in the above synthesis example were placed in a four-necked flask and heated to 70 ° C. to dissolve them. After washing the oil layer with water, the oil layer was cooled to 25 ° C. at a cooling rate of 15 ° C./hour, and seed crystals were added at 40 ° C. on the way to precipitate crystals. The crystals were separated by filtration and dried to obtain 20.6 g of crystals of the target compound A. The endothermic peak top temperature by differential scanning calorimetry was 111.8 ° C., and the loose bulk density was 0.58 g / cm 3 .
  • the characteristic diffraction angle 2 ⁇ (deg, peak with relative integral intensity of 10 or more) in the powder X-ray diffraction peak pattern by Cu—K ⁇ rays is 10.1, 11.7, 15.2, 15.5. , 17.7, 19.4, 20.2, 21.0, 22.2, 23.3, 24.3, 24.6, 26.8, 27.1.
  • FIG. 3 shows a chart diagram showing differential scanning calorific value analysis data of the obtained crystals
  • FIG. 4 shows a chart diagram showing powder X-ray diffraction data by Cu—K ⁇ rays.
  • Example 3 Crystal of Compound A 30.0 g of crude crystals and 300 g of methanol obtained in the above synthesis example were placed in a four-necked flask and heated to 60 ° C. to dissolve them. The mixture was cooled to 25 ° C. at a cooling rate of 15 ° C./hour, and seed crystals were added at 55 ° C. on the way to precipitate crystals. The crystals were separated by filtration and dried to obtain 22.7 g of crystals of the target compound A. The endothermic peak top temperature by differential scanning calorimetry was 108.3 ° C., and the loose bulk density was 0.44 g / cm 3 .
  • the characteristic diffraction angle 2 ⁇ (deg, peak with relative integral intensity of 10 or more) in the powder X-ray diffraction peak pattern by Cu—K ⁇ rays is 10.0, 11.7, 15.2, 15.4. , 17.7, 19.3, 20.2, 21.0, 22.1, 23.3, 24.3, 24.6, 26.8, 27.0.
  • FIG. 5 shows a chart showing the differential scanning calorific value analysis data of the obtained crystals
  • FIG. 6 shows a chart showing the powder X-ray diffraction data by Cu—K ⁇ rays.
  • Example 4 Crystal of Compound A 30.0 g of crude crystals and 54.0 g of a 75% acetone aqueous solution obtained in the above synthesis example were placed in a four-necked flask and heated to 55 ° C. to dissolve them. The mixture was cooled to 25 ° C. at a cooling rate of 15 ° C./hour, and seed crystals were added at 50 ° C. on the way to precipitate crystals. The crystals were separated by filtration and dried to obtain 27.2 g of crystals of the target compound A. The endothermic peak top temperature by differential scanning calorimetry was 110.7 ° C., and the loose bulk density was 0.44 g / cm 3 .
  • the characteristic diffraction angle 2 ⁇ (deg, peak with relative integral intensity of 10 or more) in the powder X-ray diffraction peak pattern by Cu—K ⁇ rays is 10.0, 11.6, 11.8, 15.4. , 17.7, 19.3, 20.1, 20.9, 22.1, 23.3, 24.3, 24.5, 26.8, 27.0.
  • FIG. 7 shows a chart showing the differential scanning calorific value analysis data of the obtained crystals
  • FIG. 8 shows a chart showing the powder X-ray diffraction data by Cu—K ⁇ rays.

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Abstract

Le problème à résoudre par la présente invention concerne la fourniture d'un cristal de 2, 2'-bis(éthoxycarbonylméthoxy)-1, 1'-binaphtyle qui est approprié en tant que matière première de résine ayant d'excellentes caractéristiques optiques. La solution selon l'invention concerne un cristal de 2, 2'-bis(éthoxycarbonylméthoxy)-1, 1'-binaphtyle, en particulier un cristal de 2, 2'-bis(éthoxycarbonylméthoxy)-1, 1'-binaphtyle qui a une température de pic endothermique dans une plage spécifique telle que déterminée par analyse de calorimétrie différentielle à balayage, un pic spécifique dans un motif de pic de diffraction de rayons X sur poudre à l'aide d'un rayon Cu-Kα, ou une densité apparente en vrac dans une plage spécifique.
PCT/JP2020/027640 2019-07-19 2020-07-16 Cristal de 2, 2'-bis(éthoxycarbonylméthoxy)-1, 1'-binaphtyle WO2021015083A1 (fr)

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KR20230108320A (ko) 2021-02-05 2023-07-18 미쓰이 가가쿠 가부시키가이샤 중합성 조성물, 수지, 성형체, 광학 재료, 및 렌즈
WO2023176687A1 (fr) * 2022-03-14 2023-09-21 本州化学工業株式会社 Composé de biphénanthrène ou sel de métal alcalin de celui-ci
WO2024171925A1 (fr) * 2023-02-15 2024-08-22 田岡化学工業株式会社 Cristal de composé diester ayant un squelette binaphtyle et son procédé de production

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JP2018059074A (ja) * 2016-10-06 2018-04-12 大阪ガスケミカル株式会社 フルオレン骨格を有するポリエステル樹脂

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JP2018059074A (ja) * 2016-10-06 2018-04-12 大阪ガスケミカル株式会社 フルオレン骨格を有するポリエステル樹脂

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