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A kind of preparation method of pentafluorophenol

A technology of pentafluorophenol and hexafluorobenzene, which is applied in the field of preparation of pentafluorophenol, can solve the problems of poor solvent recovery effect, low product yield and purity, and high single impurity content, and achieve the maximum single impurity content of the product. The effect of good product quality and less catalyst consumption

Active Publication Date: 2020-04-14
QUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to solve the technical problems of many side reactions, poor solvent recovery effect, low product yield and purity, and high single impurity content in the prior art, and provide a simple and reasonable process with few side reactions. , reaction yield and the high pentafluorophenol preparation method of product purity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] (1) Preparation of functionalized D101 macroporous adsorption resin

[0023] Add 1000g of D101-Cl macroporous adsorption resin with a degree of chloromethylation of 1.5mmol / g and 13.5L of dimethylformamide successively in the reaction kettle, and static swelling After 15 hours, add 3500g sodium chloride, 350g p-aminobenzotrifluoride and 500g sodium hydroxide, stir and react at 65°C for 48 hours, wash repeatedly with ethanol and distilled water until no precipitation occurs after adding silver nitrate solution, and dry to obtain functionalized The D101 macroporous adsorption resin, the functionalization degree is 1.05mmol / g;

[0024] (2) Preparation of pentafluorophenol

[0025] Add 100g hexafluorobenzene, 500g mass fraction 80% tert-butanol aqueous solution, 90g potassium hydroxide, 5g tetrabutyl ammonium bisulfate, 1g N-sulfonic acid propyl-3-methylpyridine trifluoromethanesulfonate in the reaction kettle Acid salt, 0.1g N-methyl-2-[(2-methylphenoxy)acetyl]hydrazine ...

Embodiment 2

[0029] (1) Preparation of functionalized D101 macroporous adsorption resin

[0030] Add 1000g of D101-Cl macroporous adsorption resin with a degree of chloromethylation of 1.5mmol / g and 13.5L of dimethylformamide successively in the reaction kettle, and static swelling After 15 hours, add 3500g sodium chloride, 350g p-aminobenzotrifluoride and 500g sodium hydroxide, stir and react at 65°C for 48 hours, wash repeatedly with ethanol and distilled water until no precipitation occurs after adding silver nitrate solution, and dry to obtain functionalized The D101 macroporous adsorption resin, the functionalization degree is 1.05mmol / g;

[0031] (2) Preparation of pentafluorophenol

[0032] Add 100g hexafluorobenzene, 500g mass fraction 80% tert-butanol aqueous solution, 90g potassium hydroxide, 5g tetrabutyl ammonium bisulfate, 1g N-sulfonic acid propyl-3-methylpyridine trifluoromethanesulfonate in the reaction kettle salt, 0.1g N-methyl-2-[(2-methylphenoxy)acetyl]hydrazinemethyl...

Embodiment 3

[0036] (1) Preparation of functionalized D101 macroporous adsorption resin

[0037] Add 1000g of D101-Cl macroporous adsorption resin with a degree of chloromethylation of 1.5mmol / g and 13.5L of dimethylformamide successively in the reaction kettle, and static swelling After 15 hours, add 3500g sodium chloride, 350g p-aminobenzotrifluoride and 500g sodium hydroxide, stir and react at 65°C for 48 hours, wash repeatedly with ethanol and distilled water until no precipitation occurs after adding silver nitrate solution, and dry to obtain functionalized The D101 macroporous adsorption resin, the functionalization degree is 1.05mmol / g;

[0038] (2) Preparation of pentafluorophenol

[0039]Add 100g hexafluorobenzene, 300g mass fraction 85% tert-butanol aqueous solution, 75g potassium hydroxide, 2g tetrabutyl ammonium bisulfate, 0.75g N-sulfonic acid propyl-3-picoline trifluoromethane in the reaction kettle Sulfonate, 0.1g N-methyl-2-[(2-methylphenoxy)acetyl]hydrazine methylthioami...

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PUM

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Abstract

The invention provides a pentafluorophenol preparation method, which comprises: using hexafluorobenzene and potassium hydroxide as raw materials, adding an appropriate amount of tetrabutylammonium hydrogen sulfate, N-sulfopropyl-3-methylpyridine triflate, N-methyl-2-[(2-methylphenoxy)acetyl]hydrazinium methylthioamide and 2,2,6,6-tetramethylpiperidine-oxynitride to a tert-butyl alcohol aqueous solution with a mass fraction of 80-85%, heating to achieve a slight boiling state, carrying out a reflux reaction for 2-3 h, adding an appropriate amount of water, distilling to recover the tert-butyl alcohol solvent, adjusting the PH value of the remaining aqueous solution by using refined hydrochloric acid to 9-10, adsorbing with a functionalized D101 macroporous adsorption resin, acidifying with refined hydrochloric acid to achieve the PH value of 1-2, layering, distilling the upper layer water phase until no oily substance exists, collecting the distilled product, combining the collected product and the lower layer oil phase, rectifying, collecting the distillate at the temperature of 142-144 DEG C, and cooling to a room temperature to obtain the colorless and transparent crystal pentafluorophenol. According to the present invention, the preparation method has advantages of simple and reasonable process, less side reactions, high reaction yield and high product purity, and can meet the quality requirements for the preparation of the high-quality liquid crystal materials and drugs.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of pentafluorophenol. Background technique [0002] Pentafluorophenol, the full name of which is 2,3,4,5,6-pentafluorophenol, is an important intermediate in medicine, liquid crystals and polymer materials, and is mostly used in the preparation of oral therapeutic drugs for hepatitis C, Sofosbuvir, Pentafluorophenyl active esters synthesized by peptides and intermediates of high-performance polyfluorinated liquid crystal materials. [0003] CN1847210A proposes a method for preparing Grignard reagent by Grignard reaction with pentafluorobromobenzene as raw material, and then performing oxidation reaction with peroxide to prepare pentafluorophenol. CN103420801A adopts pentafluorobromobenzene and alkylmagnesium halide displacement reaction to prepare Grignard reagent, and then carries out oxidation reaction with peroxide to prepare pentafluorophenol. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/02C07C37/70C07C37/82C07C39/27B01J31/02
CPCB01J31/0271C07C37/02C07C37/685C07C37/70C07C37/82C07C39/27
Inventor 冯晓亮吕延文谢建伟雷宏谢艳吴晓秉
Owner QUZHOU UNIV
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