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Method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, crystal of said compound, and method for producing said crystal

A technology of hydroxyethoxy and manufacturing methods, applied in the directions of organic chemistry methods, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of high bulk density, low bulk density, etc., to improve the purity, reduce the manufacturing cost, Handling easy effects

Inactive Publication Date: 2014-11-12
HONSHU CHEM INDAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] It is known that conventional low melting point 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene crystals have a low bulk density, while high melting point 9,9-bis(4-(2- The bulk density of hydroxyethoxy)phenyl)fluorene crystals is high

Method used

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  • Method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, crystal of said compound, and method for producing said crystal
  • Method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, crystal of said compound, and method for producing said crystal
  • Method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, crystal of said compound, and method for producing said crystal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] A four-necked flask equipped with a thermometer, a stirrer, and a cooling tube was charged with 544.7 g (3.94 mol) of 2-phenoxyethanol. After replacing the reaction vessel with nitrogen, 840.7 g (8.75 mol) of methanesulfonic acid was added at 40°C. After that, 3.8 g of β-mercaptopropionic acid was added at 50°C, and 347.9 g (1.93 mol) 9- was dissolved in 521.9 g (3.78 mol) of 2-phenoxyethanol at 50° C. for 1 hour. A solution of fluorenone for the reaction. After the dripping was completed, stirring was performed at 50°C for 17 hours. The reaction solution was analyzed by high performance liquid chromatography using a standard curve. As a result, the yield of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene present in the reaction solution was 85.4%.

[0078] After the completion of the reaction, 1287.2 g of toluene and 890.9 g of water were added at 50° C. while stirring, and then left to stand to extract 1664 g of the water layer. The concentration of methanesulfonic acid in ...

Embodiment 2

[0083] A four-necked flask equipped with a thermometer, a stirrer, and a cooling tube was charged with 60.0 g of crude crystals obtained in the same manner as in Example 1, and after nitrogen substitution, 60.0 g of 1-butanol and 60.0 g of toluene were added, and the temperature was raised to Dissolve at 70°C. Thereafter, a seed crystal of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene as a high melting point crystal was added at 60°C, and the crystal was precipitated while being held at 35°C for 30 minutes. After that, the temperature was raised to 50°C and slowly cooled to 25°C, and the precipitated crystals were filtered out. The obtained crystals were heated to 80°C under reduced pressure and dried to obtain 44.3 g of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene. The yield relative to the crude crystals was 74%, and the purity analyzed by high performance liquid chromatography was 99.2%. The DSC data of the obtained crystals are as follows figure 2 Shown.

[0084] Maximum endot...

Embodiment 3

[0087] A four-necked flask equipped with a thermometer, a stirrer, and a cooling tube was charged with 60.0 g of the crude crystals obtained in the same manner as in Example 1. After nitrogen replacement, 40.0 g of 1-butanol and 80.0 g of toluene were added, and the temperature was raised to Dissolve at 70°C. Thereafter, a seed crystal of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene as a high melting point crystal was added at 60°C, and the crystal was precipitated while being held at 33°C for 30 minutes. After that, the temperature was raised to 50°C and slowly cooled to 25°C, and the precipitated crystals were filtered out. The obtained crystals were heated to 70°C under reduced pressure and dried to obtain 44.3 g of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene. The yield relative to the crude crystals was 75%, and the purity analyzed by high performance liquid chromatography was 99.0%. The DSC data of the obtained crystals are as follows image 3 Shown.

[0088] Maximum endoth...

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Abstract

A method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, which can be used for obtaining 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene having a high static bulk density and a low melting point, and is characterized in that 9-fluorenone is reacted with 2-phenoxy ethanol in the presence of methanesulfonic acid and the resultant product is purified using butanol.

Description

Technical field [0001] The present invention relates to a method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, a crystal body thereof, and a method for producing crystal body thereof. Background technique [0002] In recent years, fluorene derivatives such as 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene have excellent heat resistance and transparency, and show high refractive index, so they can be expected as epoxy resins , Polyester resin, polycarbonate resin and other resin raw materials. [0003] As a method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene by reacting 9-fluorenone with 2-phenoxyethanol, Patent Document 1 and Patent Document 2 describe the use Sulfuric acid catalyst method. Through such a reaction, although the reaction rate is faster than other catalysts, it is synthesized or easily sulfonated as a by-product sulfonate. As a result, sulfur remains in the product, which affects the color tone of the target, and is used as an optical material ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/30C07C41/40C07C43/23C07B61/00
CPCC07C41/30C07C41/40C07C43/23
Inventor 岩井龙也沟口隼国吉祥悟
Owner HONSHU CHEM INDAL
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