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Preparation of 9,9-bis(6-hydroxynaphthalene-2-yl) fluorene crystal without complex residual solvent

A technology for residual solvents and hydroxynaphthalene, which is applied in the field of preparation of 9,9-bis(6-hydroxynaphthalene-2-yl)fluorene crystals without complexing residual solvents, and can solve difficult to implement, high melting point, high temperature melting products Problems such as easy discoloration

Active Publication Date: 2018-09-28
JIANGSU EVER GALAXY CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the 9,9-bis(6-hydroxynaphthalene-2-yl)fluorene crystal complexed with residual solvent can be heated above the melting point and melted to remove the complexed solvent, its melting point is very high and high temperature Molten products are prone to discoloration and are difficult to implement industrially

Method used

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  • Preparation of 9,9-bis(6-hydroxynaphthalene-2-yl) fluorene crystal without complex residual solvent
  • Preparation of 9,9-bis(6-hydroxynaphthalene-2-yl) fluorene crystal without complex residual solvent
  • Preparation of 9,9-bis(6-hydroxynaphthalene-2-yl) fluorene crystal without complex residual solvent

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0027] Add 9-fluorenone (18g, 0.1mol), 2-naphthol (33.1g, 0.23mol), 3-mercaptopropionic acid (1.0g), toluene 200 mL into the reaction flask, stir to dissolve and slowly add 98 % sulfuric acid 20.2g (0.2 mol). 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*100mL water at 80°C. Separate the organic layer, evaporate the solvent under reduced pressure, add 100 mL of methanol, and stir to precipitate crystals. Use 1-chloropropane to recrystallize, and lower the temperature to 0°C under stirring at a speed of 0.3-1.0°C / min to crystallize. The crystals were filtered out, and vacuum-dried at 100°C / 1.33kPa for 8 hours to obtain 33.8 g of crystals, with a yield of 75.0% and a purity of 99.3% by HPLC analysis. 1 H NMR (500MHz, CDCl 3 )δ: 7.00-7.12(m, 4H), 7.37-7.41(m, 2H),7.51-7.57(m, 14H), 7.82-7.97(d, 2H). TGA spectrum (see fig...

example 2

[0029] The crude product was synthesized by the same steps, and then recrystallized with 1,2-dichloroethane, and crystallized at a rate of 0.3-1.0°C / min to 0°C while stirring. The crystals were filtered out and vacuum-dried at 100°C / 1.33 kPa for 8 hours to obtain 36.5 g of crystals with a yield of 81.0% and a purity of 99.5% by HPLC analysis. The X-powder diffraction spectrum shows that it has the same crystal form as Example 1.

example 3

[0031] The crude product was synthesized by the same steps, and then recrystallized with chloroform, and the temperature was lowered to 0 ℃ under stirring at a rate of 0.3-1.0 ℃ / min for crystallization. The crystals were filtered out and vacuum-dried at 100° C. / 1.33 kPa for 8 hours to obtain 33.5 g of crystals, with a yield of 74.5 % and a purity of 99.2 % by HPLC analysis. The X-powder diffraction spectrum shows that it has the same crystal form as Example 1.

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Abstract

The invention discloses a 9,9-bis(6-hydroxynaphthalene-2-yl) fluorene crystal without complex residual solvent and is obtained through beating a low-boiling-point chlorine-containing solvent and carrying out vacuum drying treatment. The thermal gravimetric analysis (TGA) spectrum shows that no complex residual solvent exists, and the melting endothermic peak on the differential scanning calorimeter (DSC) spectrum is 260-266 DEG C. The characteristic 2-theta values of the X-ray powder diffraction (XRPD) analysis are as follows: 8.3+ / -0.20 (48), 9.7+ / -0.20 (50), 17.3+ / -0.20 (74), 19.3+ / -0.20 (100), 19.7+ / -0.20 (72), 20.0+ / -0.20 (61), 22.6+ / -0.20 (48) and 26.9+ / -0.20 (32). The crystal without complex residual solvent has the advantages that when materials of polycarbonate, polyester, polyimide and the like are prepared by adopting a solvent-free polycondensation process, the release and dissipation of residual toxic and harmful solvents are prevented, the air environment is prevented frombeing polluted, and the quality performance of polymer materials is not seriously influenced by the release of encapsulated solvent in the reaction.

Description

Technical field: [0001] 9,9-bis(6-hydroxynaphthalene-2-yl)fluorene crystal and its crystal form without complexing residual solvent as photoelectric material intermediate. technical background: [0002] 9,9-bis(6-hydroxynaphthalene-2-yl)fluorene is an important intermediate of photoelectric materials, and materials such as polycarbonate, polyester, polyimide, epoxy resin and acrylic resin derived from it have Excellent properties such as high refractive index, high thermal stability and good transparency have important applications in photoconductive devices, light-emitting diode packaging materials, optical lenses, liquid crystal display enhancement films, polarizing films, reflective films, and electronic lithography materials. The preparation of these optical materials requires the highly passive monomer 9,9-bis(6-hydroxynaphthalen-2-yl)fluorene. However, 9,9-bis(6-hydroxynaphthalene-2-yl)fluorene is very easy to complex with general organic solvents such as toluene, ace...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/20C07C37/84C07C39/17
CPCC07C37/20C07C37/84C07C39/17C07C2603/18C07B2200/13
Inventor 田礼彬陆国元陆晓峰苏波张强
Owner JIANGSU EVER GALAXY CHEM CO LTD
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