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Preparation of novel fluorine-containing bisphenol compound

A technology of phenolic compounds and phenol, which is applied in the field of synthesis of novel fluorine-containing bisphenol compound 1,3-bis-hexafluoropropylidene)benzene, can solve the problems of few reports and no discovery of fluorine-containing phenol compounds, and achieve Low cost and wide application effect

Inactive Publication Date: 2014-03-19
BEIHANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although there are many reports on polyfluorinated compounds, there are fewer reports on fluorine-containing phenolic compounds, and there is no patent disclosure of 1,3-bis(2-(4-hydroxyphenyl)-hexafluoropropylidene)benzene report

Method used

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  • Preparation of novel fluorine-containing bisphenol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Into a 500mL glass bottle equipped with a reflux condenser (the upper end of the condenser is equipped with a nitrogen protection balloon), a thermometer and an addition funnel, add 200ml of tetrahydrofuran and 2.8g (0.4mol) of lithium wire, heat to 40°C, and drop under vigorous stirring Add 11.8g (0.2mol) m-dibromobenzene, after the lithiation reaction is initiated, the temperature of the reaction solution rises to boiling quickly. Control the rate of addition to maintain a slight boiling state, and it takes about 1 hour for all the drops to be completed. Keep the slightly boiling state and continue to react for 2h, and the lithium filaments completely disappear.

[0020] Cool the above reaction solution to room temperature, add 62g (0.4mol) of hexafluoroacetone dropwise under stirring, control the rate of addition to keep the temperature of the reaction solution not higher than 40°C, complete the dropwise addition of hexafluoroacetone within 1h, and continue the natur...

Embodiment 2

[0024]Add 200ml of toluene-tetrahydrofuran (mass ratio 3:1) and 2.8g (0.4mol) of lithium wire into a 500mL glass bottle equipped with a reflux condenser (a nitrogen protection balloon is installed at the upper end of the condenser), a thermometer and an addition funnel, and heat At 60°C, 11.8 g (0.2 mol) of m-dibromobenzene was added dropwise under vigorous stirring. After the lithiation reaction was initiated, the temperature of the reaction solution rose to slightly boiling quickly. Control the rate of addition to maintain a slight boiling state, and it takes about 0.5 hours for all the drops to be completed (compared with the higher boiling point of tetrahydrofuran medium, the rate of addition can be faster). Keep the slightly boiling state and continue the reaction for 1h, and the lithium filaments completely disappear.

[0025] The above reaction solution was cooled to room temperature, and 62g (0.4mol) of hexafluoroacetone was added dropwise under stirring, and the rate ...

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Abstract

The invention relates to a preparation method for preparing a novel fluorine-containing bisphenol compound, namely 2, 2-bis (4-(2, 4-diaminophenoxy) phenyl) hexafluoropropane. The preparation method comprises the following steps of lithiating m-dibromobenzene to prepare m-phenyl dilithium salt; performing addition reaction on the m-phenyl dilithium salt and hexafluoroacetone to prepare 1, 3-bis (2-hydroxy-hexafluoropropylidene) benzene; and performing condensation reaction on the 1, 3-bis (2-hydroxy-hexafluoropropylidene) benzene and phenol to prepare 1, 3-bis (1-(4-hydroxyphenyl)-hexafluoropropylidene) benzene. The preparation method provided by the invention has the advantages of simplicity in operation and low cost, the purity of the obtained product is more than 99%, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of a novel fluorine-containing bisphenol compound 1,3-bis(2-(4-hydroxyphenyl)-hexafluoropropylidene)benzene, which belongs to the technical field of fine chemicals. technical background [0002] Since the advent of freon in the early 1930s, organic fluorine chemistry has been showing a vigorous development trend, and fluorine-containing compounds have penetrated into almost every aspect of our daily life. After 1945, with the onset of the Cold War, various defense programs provided an enduring impetus for the continued development of fluorine chemistry and the use of fluorine-containing compounds. In the 1950s and 1960s, due to the emergence of more civilian products such as fluorine-containing drugs, pesticides and fluorine-containing materials, the research on organic fluorine chemistry was pushed to the forefront. For example, the substance called Halon is a Bromine-containing and fluorine-containing alka...

Claims

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Application Information

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IPC IPC(8): C07C39/367C07C37/11C08G73/06
CPCC07C29/40C07C37/16C07F1/02C07C39/367C07C33/46
Inventor 王明存王志强
Owner BEIHANG UNIV
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