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Preparation method of 9,9-bis(4-aminophenyl)fluorene

A technology of aminophenyl and fluorenone, which is applied in the field of preparation of 9,9-bis(4-aminophenyl)fluorene, can solve the problems of difficult operation, large amount of recrystallization solvent, cumbersome process route, etc., and achieve inhibition The formation of by-products, mild method conditions, and the effect of increasing the reaction yield

Inactive Publication Date: 2012-04-18
CHANGZHOU SUNLIGHT PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of this method are: two-step condensation reaction is required, the reaction conditions are complicated, the solvent demand is large and the toxicity is high, and the purification of intermediates and products is relatively complicated, resulting in cumbersome process routes and low yields, and is not suitable for large-scale industrial production.
The disadvantages of this method are: (1) Aniline is used as a solvent, and the amount of aniline is large (11 times the equivalent of fluorenone, and 2.6 times the equivalent of aniline hydrochloride)
(2) The reaction temperature is too high (the boiling point of aniline is as high as 184°C), the operation is not easy, and aniline is easily oxidized at high temperature, which is not conducive to the purification of the product
(3) Post-treatment requires two recrystallizations to obtain qualified products, and the amount of recrystallization solvent is large
(4) The reaction yield is low, only 54%, which is not suitable for large-scale industrial production
The disadvantages of this method are: (1) Aniline is used as a solvent, and the amount of aniline is very large (22 times the equivalent of fluorenone, 7 times the equivalent of aniline hydrochloride)
(2) The final yield is only 20%

Method used

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  • Preparation method of 9,9-bis(4-aminophenyl)fluorene

Examples

Experimental program
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Effect test

Embodiment 1）

[0013] The preparation method of this example is as follows: under nitrogen protection, add 3.6 g of fluorenone (20 mmol), 7.2 g of aniline hydrochloride (55.6 mmol), and 0.5 g to a 100 mL two-necked bottle equipped with a water separator sodium bisulfite (4.8 mmol), 8.8 mL of aniline (96.4 mmol) and 6 mL of toluene. Slowly rise to 120°C under stirring, react for 30 minutes, separate out the green liquid produced in the water separator, maintain the temperature for 3 hours, separate out the water produced in the water separator, then slowly raise the temperature to 135°C, maintain this temperature for reaction After 1.5 hours, the reaction can be stopped when no more water is produced in the water separator.

[0014] Cool the reacted material to about 60°C, add 10wt% potassium hydroxide solution to the mixed solution, adjust the pH value to 9, stir for 15 minutes while it is hot, then carry out suction filtration, and wash the filter cake with 30mL of toluene Recrystallizatio...

Embodiment 2～ Embodiment 3）

[0016] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0017]

Embodiment 4～ Embodiment 6）

[0019] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 2.

[0020]

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Abstract

The invention discloses a preparation method of 9,9-bis(4-aminophenyl)fluorene, which comprises the following steps: under the protection of inert gas, adding fluorenone, aniline hydrochloride and aniline used as raw materials, methyl benzene used as a solvent and sodium bisulfite used as a catalyst into a reaction device with a water separator; heating up to 110-130 DEG C while stirring, reacting for 20-40 minutes, and then separating out a liquid generated in the water separator; continuing to react at this temperature for 2-4 hours, and then separating out water generated in the water separator; slowly heating up to 130-140 DEG C, reacting at this temperature for 1-2 hours, and stopping the reaction when no water is generated in the water separator; and carrying out post treatment to obtain the 9,9-bis(4-aminophenyl)fluorene. The method has the advantages of moderate conditions and high yield, and is suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a preparation method of 9,9-bis(4-aminophenyl)fluorene. Background technique [0002] 9,9-bis(4-aminophenyl)fluorene has good optical properties and semiconductor properties, and it is also an important intermediate for the synthesis of polyfluorene derivatives. Its preparation method mainly contains following several kinds at present: [0003] U.S. Patent No. 5,387,725 discloses that an intermediate 9,9-dichlorofluorene is prepared by reacting fluorene and carbon tetrachloride under basic conditions and the presence of a phase transfer catalyst, and then reacting the intermediate with aniline The condensation reaction gives 9,9-bis(4-aminophenyl)fluorene. The disadvantages of this method are: two-step condensation reaction is required, the reaction conditions are complicated, the solvent demand is large and the toxicity is high, and the purification of intermediates a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/50C07C209/68
Inventor 游劲松闵雪锋吴建华胡国宜兰静波李明亮仇鲸祥
Owner CHANGZHOU SUNLIGHT PHARMA
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