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Solvate crystal of 9,9-bis(6-hydroxy naphthalene-2-group) fluorene and preparation thereof

A technology of solvate and hydroxynaphthalene, which is applied in the field of solvate crystals of 9,9-bifluorene and its preparation, can solve the problems of deepening color, poor thermal stability, and decreased purity, and achieve good fluidity and thermal stability High performance and high bulk density

Active Publication Date: 2014-12-24
JIANGSU EVER GALAXY CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Japanese patent JP2012207008 used the same synthetic method to prepare the crude product of 9,9-bis(6-hydroxynaphthalene-2-yl)fluorene, and the obtained crude product was recrystallized from toluene to obtain α-crystal form (melting point 213°C), Heating to 207°C to transform into β-crystal form (melting point 226°C), recrystallization with isopropyl ether to obtain γ-crystal form (melting point 230°C), these polycrystals have poor thermal stability, and the color deepens when stored at 40°C for four months (increased chroma), decreased purity (gamma-crystal purity decreased from 99.4% to 88.0%)

Method used

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  • Solvate crystal of 9,9-bis(6-hydroxy naphthalene-2-group) fluorene and preparation thereof
  • Solvate crystal of 9,9-bis(6-hydroxy naphthalene-2-group) fluorene and preparation thereof
  • Solvate crystal of 9,9-bis(6-hydroxy naphthalene-2-group) fluorene and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 9-fluorenone (36g, 0.2mol), 2-naphthol (66.24g, 0.46 mol), 3-mercaptopropionic acid (cocatalyst) (2g), toluene 300 mL into the reaction flask, and stir until 9-fluorenone After the ketone and 2-naphthol were dissolved, 39.4 g (0.4 mol) of 98% sulfuric acid was slowly added dropwise. The reaction was stirred at 50-60°C for 4-8 hours. HPLC analysis confirmed that the 9-fluorenone content was below 0.1% and the reaction was stopped. Add 10% sodium hydroxide to neutralize, wash with 3*200 g water at 80°C. Separate the organic layer, evaporate the solvent under reduced pressure, add 200 mL of methanol, and stir to precipitate crystals. Recrystallize with acetonitrile, filter out the crystals, and dry in vacuo at 60°C for 8 hours to obtain 68g of solvate crystal I with a yield of 75.5%, and a purity of 99.5% by high performance liquid chromatography (HPLC). 1 H-NMR) (500Mz, CDCl 3 )δ: 7.03-7.11(m, 4H), 7.38-7.40(m, 2H), 7.50-7.58(m, 14H), 7.83-7.98(d, 2H). The X-ray ...

Embodiment 2

[0024] Add 9-fluorenone (36g, 0.2mol), 2-naphthol (66.24g, 0.46mol), 3-mercaptopropionic acid (co-catalyst) (2g), toluene 300 mL in the reaction flask, stir until 9- After fluorenone and 2-naphthol were dissolved, 39.4 g (0.4 mol) of 98% sulfuric acid was slowly added dropwise. The reaction was stirred at 50-60°C for 4-8h. HPLC analysis confirmed that the 9-fluorenone content was below 0.1% and the reaction was stopped. Add 10% sodium hydroxide to neutralize, wash with 3*200 g water at 80°C. Separate the organic layer, evaporate the solvent under reduced pressure, add 200 mL of methanol, and stir to precipitate crystals. Recrystallize with ethyl acetate, filter out the crystals, and vacuum dry at 60°C for 8 hours to obtain 72g of solvate crystal II with a yield of 80.0% and a purity of 99.6% as analyzed by high performance liquid chromatography (HPLC). H NMR spectrum test ( 1 H-NMR) (500Mz, CDCl 3 ) test, its δ values ​​are 7.01-7.10(m, 4H), 7.35-7.40(m, 2H), 7.48-7.58(...

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Abstract

The invention discloses a solvate crystal of 9,9-bis(6-hydroxy naphthalene-2-group) fluorene and preparation thereof. A solvate crystal prepared from the 9,9-bis(6-hydroxy naphthalene-2-group) fluorene and acetonitrile is a solvate crystal I of the 9,9-bis(6-hydroxy naphthalene-2-group) fluorene, and a solvate crystal prepared from the 9,9-bis(6-hydroxy naphthalene-2-group) fluorene and ethyl acetate is a solvate crystal II of the 9,9-bis(6-hydroxy naphthalene-2-group) fluorene. The solvate crystal I and solvate crystal II of the 9,9-bis(6-hydroxy naphthalene-2-group) fluorene, which is prepared through the invention achieve the maximum melting endothermic peaks of 261-266 DEG C and the stacking density of 0.4 g / mL after being desolvated, is basically unchanged in color and purity after being preserved at 40 DEG C for three months due to high heat stability and has the advantages of high stacking density, good flowability and easiness for loaded material transfer.

Description

technical field [0001] The invention relates to a solvate crystal of 9,9-bis(6-hydroxynaphthalene-2-yl)fluorene and its preparation. Background technique [0002] 9,9-bis(6-hydroxynaphthalene-2-yl)fluorene is an important intermediate of optoelectronic materials. The epoxy resin and acrylic resin derived from it have high refractive index, high thermal stability and good transparency. It has important applications in light-emitting diode packaging materials, light guide devices, enhancement films, polarizing films, reflective films, optical lenses, gas separation films, and electronic lithography materials. [0003] Japanese patent JP2007099741 reported the preparation method of 9,9-bis(6-hydroxynaphthalene-2-yl)fluorene, using concentrated sulfuric acid as catalyst, 3-mercaptopropionic acid as cocatalyst, 9-fluorenone and 2-naphthol Stir and react in toluene solution at 60°C for 6 hours, wash with sodium hydroxide solution after the reaction, and recrystallize the crude ...

Claims

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Application Information

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IPC IPC(8): C07C39/17C07C37/84
CPCC07B2200/13C07C37/84C07C2603/18C07C39/17
Inventor 田礼彬陆国元张强
Owner JIANGSU EVER GALAXY CHEM CO LTD
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