Preparation method of 2,2-di[4-(4-amidophenoxy)phenyl]hexafluoropropane

A technology of aminophenoxy and hexafluoropropane, applied in 2 fields, can solve problems such as low product yield and long preparation process route

Inactive Publication Date: 2007-02-07
SHANGHAI RES INST OF SYNTHETIC RESINS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation process has a long route and the product yield is not high, which needs to be improved in terms of economic benefits and technological advancement

Method used

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  • Preparation method of 2,2-di[4-(4-amidophenoxy)phenyl]hexafluoropropane
  • Preparation method of 2,2-di[4-(4-amidophenoxy)phenyl]hexafluoropropane

Examples

Experimental program
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Effect test

Embodiment 1

[0014] (a) Preparation of 2,2-bis[4-(4-nitrophenoxy)phenyl]hexafluoropropane;

[0015] 33.6g (0.1mol) of bisphenol AF was dissolved in 180ml of dimethylformamide / 20ml of toluene solution, then 32g (0.23mol) of potassium carbonate was added, and 31.5g (0.2mol) of p-chloro Nitrobenzene was refluxed at 133°C for 8.5 hours, and the precipitate was filtered to obtain 2,2-bis[4-(4-nitrophenoxy)phenyl]hexafluoropropane with a melting point of 157.6°C and a yield of 99%.

[0016] (b) Preparation of 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane;

[0017] 29g (0.05mol) of above-mentioned preparation 2,2-bis[4-(4-nitrophenoxy group) phenyl] hexafluoropropane is dissolved in 200ml ethanol, in 0.7g iron trichloride / 5.2g active carbon reduction catalyst In the presence of hydrazine hydrate, 10g (0.2mol) hydrazine hydrate was refluxed at 77°C for 4 hours, filtered hot, and filtered under cooling to obtain 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, whose melting point was 164°...

Embodiment 2

[0019] (a) Preparation of 2,2-bis[4-(4-nitrophenoxy)phenyl]hexafluoropropane;

[0020] In addition to adding 120ml dimethylacetamide / 80ml toluene, 24g potassium carbonate and 36.2g p-chloronitrobenzene, reflux at 123°C for 13 hours to obtain 2,2-bis[4-(4-nitrophenoxy) The melting point of phenyl]hexafluoropropane is about 158.7°C. Other formula, operation and result are the same as embodiment 1.

[0021] (b) Preparation of 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane;

[0022] In addition to adding 261ml of methanol, 0.5g of ferric chloride / 5.0g of activated carbon and 7.5g of hydrazine hydrate to reflux at 76°C for 5 hours, the prepared 2,2-bis[4-(4-aminophenoxy)phenyl ] The yield of hexafluoropropane is 90%, and the measured value of elemental analysis is: C, 62.50; H, 3.90; N, 5.35. Other formulas, operating steps and results are exactly the same as Example 1.

Embodiment 3

[0024] (a) Preparation of 2,2-bis[4-(4-nitrophenoxy)phenyl]hexafluoropropane;

[0025] In addition to adding 190ml dimethylformamide / 10ml toluene, 17g potassium carbonate and 36.2g p-chloronitrobenzene, reflux at 110°C for 4.5 hours to obtain 2,2-bis[4-(4-nitrophenoxy) The melting point of phenyl]hexafluoropropane is about 157.3°C. Other formula, operation and result are exactly the same as embodiment 1.

[0026] (b) Preparation of 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane;

[0027] Except adding 116ml ethanol, 1.0g iron trichloride / 1.1g gac and hydrazine hydrate 12.5g were refluxed at 76 ℃ for 3 hours, other formulas, operating steps and results were exactly the same as in Example 1.

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Abstract

A preparation method for 2,2-bis-[4-(4-amino-phenoxy)phenyl] hexafluoropropane includes the preparation of 2,2-bis-[4-(4-nitrophenoxy)phenyl]hexafluoropropane and the preparation of 2,2-bis-[4-(4-aminophenoxy)phenyl]hexafluoropropane. The method comprises dissolving bisphenol AF in N,N-dimethylformamide or N,N- dimethylacetamide and toluene or xylene solvent mixture, adding potassium carbonate, refluxing and dehydrating, adding p-chloronitrobenzene at 110-153DEG C for 4-13 hours, filtering and precipitating to obtain 2,2-bis-[4-(4-nitrophenoxy)phenyl]hexafluoropropane, and carrying out reduction with ferric chloride/activated carbon as the catalyst and hydrazine hydrate in methanol or ethanol to obtain 2,2-bis-[4-(4-amino-phenoxy)phenyl]hexafluoropropane with melting point of 164DEG C, purity of 99.4% and yield of 86-90%.

Description

technical field [0001] The present invention relates to a preparation method of perfluoroisopropyldiamine, more precisely, to a preparation method of 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane. Background technique [0002] Has a polymer repeating unit structure [0003] [0004] Polyimide has a high glass transition temperature (Tg above 260°C), low dielectric constant (ε=2.88 or so), good solubility in organic solvents and good melt fluidity, and is widely used in micro Electronics industry, optical field and intelligence and information industry. Specific applications include: semiconductor devices, printed wiring, liquid crystal display devices, shielding for X-ray exposure, color filters, optical fibers, coatings, and film materials. The importance of 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane as one of such polyimide components is apparent. For the production method of 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, prior art U.S. Pat. No. 4,1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/90C07C213/02
Inventor 胡志强张春华
Owner SHANGHAI RES INST OF SYNTHETIC RESINS
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