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Preparation method for bis(3-amino-4-hydroxyphenyl)hexafluoropropane

A technology of hexafluoropropane and hydroxyphenyl, which is applied in the field of dihexafluoropropane preparation, can solve the problems of harsh reaction conditions, difficult wastewater treatment, high price, etc., and achieve simple separation and purification of products, mild reaction conditions, and less side reactions Effect

Active Publication Date: 2020-06-19
SHANGHAI ROLECHEM CO LTD
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Problems solved by technology

[0003] The preparation method of bis(3-amino-4-hydroxyphenyl)hexafluoropropane has been extensively studied. For example, in 1993, Japan Fushi Chemical Co., Ltd. Nishinomiya Hikari and Kawai Shunwa produced 2,2-bis(4-hydroxyphenyl)hexafluoropropane. Propane is used as raw material, nitrated by mixed acid, palladium carbon is used as catalyst, and hydrogen pressure is 5kg / cm 2 , when the temperature is 100°C, use hydrogen for reduction, filter the reaction solution, filter out the catalyst, pour the filtrate into water, and precipitate a gray reduction product, recrystallize with ethyl acetate after drying to obtain white 2,2-bis(3- Amino-4-hydroxyphenyl)hexafluoropropane; the raw materials used in the method are electronic grade products, and electronic grade 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane can be obtained, but the method receives The yield is lower than 50%, the reaction conditions are harsh, the cost is too high, and it is not suitable for industrial production
The main raw material for preparing bis(3-amino-4-hydroxyphenyl) hexafluoropropane is bisphenol AF at present, and bisphenol AF is a phenol-containing substance, and the waste water generated after the reaction is difficult to handle; and bisphenol AF is expensive, and 1kg exceeds 500 yuan
After multiple reactions and purification, the price of bis(3-amino-4-hydroxyphenyl)hexafluoropropane is more expensive, and it is difficult to realize the production of bis(3-amino-4-hydroxyphenyl)hexafluoropropane More importantly, due to the high activity of bisphenol AF, it is easy to generate polynitro compounds in the process of nitration reaction, which brings safety hazards to the safety control of nitration reaction and the waste disposal of crystallization mother liquor , is not conducive to safe production

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  • Preparation method for bis(3-amino-4-hydroxyphenyl)hexafluoropropane

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preparation example Construction

[0024] In order to solve the above problems, the invention provides a kind of preparation method of two (3-amino-4-hydroxyphenyl) hexafluoropropane, comprising the following steps:

[0025] The first step: the reactant (I) is passed through hexafluoroacetone in the presence of a catalyst to react to obtain the compound (II);

[0026] The second step: reacting the compound (II) obtained in the first step with nitric acid and sulfuric acid to obtain the compound (III);

[0027] The third step: adding the compound (Ⅲ) obtained in the second step to an inorganic base to react to obtain the compound (Ⅳ);

[0028] The fourth step: Catalytic hydrogenation of the compound (IV) obtained in the third step to obtain bis(3-amino-4-hydroxyphenyl)hexafluoropropane;

[0029] Wherein, the reactant (I) is a halogenated benzene, the compound (II) is bis(4-halophenyl)hexafluoropropane, and the compound (III) is bis(3-nitro-4-halophenyl)hexafluoropropane Fluoropropane, the compound (IV) is bis(...

Embodiment 1

[0088] Embodiment 1 provides a kind of preparation method of bis(3-nitro-4-fluorophenyl)hexafluoropropane, the synthesis reaction formula is as follows:

[0089]

[0090] Preparation steps include:

[0091] The first step: the synthesis of bis(4-fluorophenyl)hexafluoropropane

[0092] Put 96.1g of fluorobenzene into a 250mL four-neck bottle, add 20.7g of aluminum trichloride, start stirring and raise the temperature to 60°C, and pass hexafluoroacetone gas at a rate of 100mL / min. After aeration for 10 hours, the intermediate is controlled in the gas phase When the p-fluorophenylhexafluoroacetone content is 50%, stop ventilation, raise the kettle temperature to reflux reaction at 80-85°C, stop the reaction when the p-fluorophenylhexafluoroacetone content<1.0%, and the target product bis(4- The gas phase content of fluorophenyl)hexafluoropropane is 98%, and the system is black; after the kettle temperature is lowered to room temperature, 90g of water is added dropwise to quen...

Embodiment 2

[0096] Embodiment 2 provides a kind of preparation method of bis(3-nitro-4-chlorophenyl)hexafluoropropane, the synthesis reaction formula is as follows:

[0097]

[0098] Preparation steps include:

[0099] The first step: the synthesis of bis(4-chlorophenyl)hexafluoropropane

[0100] Put 133.8g of chlorobenzene into a 500mL four-necked bottle, add 36.0g of aluminum trichloride, start stirring and raise the temperature to 70°C, and pass in hexafluoroacetone gas at a speed of 100mL / min. After aeration for 6 hours, the intermediate p-chlorobenzene When the content of p-chlorophenyl hexafluoroacetone is 50%, stop the ventilation, raise the still temperature to react at 80-85°C, stop the reaction when the content of p-chlorophenyl hexafluoroacetone <1.0%, and the target product bis(4-chlorophenyl) The gas phase content of hexafluoropropane is 98%, and the system is black. Lower the temperature of the kettle to room temperature, add 100g of dichloromethane, slowly add 100g of w...

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Abstract

The invention belongs to the technical field of electronic chemical materials, and more specifically relates to a preparation method for bis(3-amino-4-hydroxyphenyl)hexafluoropropane. The preparationmethod for the bis(3-amino-4-hydroxyphenyl)hexafluoropropane disclosed by the invention comprises the following steps: step 1, introducing hexafluoroacetone into a reactant (I) in the presence of a catalyst for a reaction so as to obtain a compound (II); step 2, allowing the compound (II) obtained in the step 1 with nitric acid and sulfuric acid so as to obtain a compound (III); step 3, adding thecompound (III) obtained in the step 2 into inorganic base for a reaction so as to obtain a compound (IV); and step 4, carrying out catalytic hydrogenation on the compound (IV) obtained in the step 3so as to obtain the bis(3-amino-4-hydroxyphenyl)hexafluoropropane.

Description

technical field [0001] The invention belongs to the technical field of electronic chemical materials, and more specifically, the invention relates to a preparation method of bis(3-amino-4-hydroxyphenyl)hexafluoropropane. Background technique [0002] Bis(3-amino-4-hydroxyphenyl)hexafluoropropane is a material chemical intermediate product with excellent performance, especially it can be used as a polymer functional monomer for the preparation of polyimide, and it can be used as a resistor in wire and cable Combustion and high temperature resistant materials, membrane plastics, etc. Polyimide is a high temperature resistant polymer with excellent oxidation stability, chemical resistance, radiation resistance, good toughness and flexibility, and is widely used in aviation / aerospace, electronics / electrical , glass, automobile, precision machinery and automatic office machinery and other fields. [0003] The preparation method of bis(3-amino-4-hydroxyphenyl)hexafluoropropane h...

Claims

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Application Information

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IPC IPC(8): C07C201/08C07C205/12C07C17/263C07C25/18C07C201/12C07C205/26C07C213/02C07C215/80
CPCC07C17/2637C07C201/08C07C201/12C07C213/02C07C205/12C07C25/18C07C205/26C07C215/80
Inventor 江杰王存远蔡家豪
Owner SHANGHAI ROLECHEM CO LTD
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