Preparation method of polyfluoro aliphatic carboxylic acid

A technology of aliphatic carboxylic acid and fluorine-containing carboxylic acid potassium salt, which is applied in the synthesis of polyfluoroaliphatic carboxylic acid surface-active compounds and in the field of polyfluoroaliphatic carboxylic Low yield and other problems, to achieve the effect of less reaction by-products, high yield, easy to purify

Inactive Publication Date: 2010-07-14
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this method has many by-products and low yield, es

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0019] Example 1

[0020] Synthesis of 2,2,3,3,4,4,5,5-octafluorovaleric acid:

[0021] In a 2L three-necked flask were sequentially added 2,2,3,3,4,4,5,5-octafluoropentanol 116.0g, 700g water, and 200g acetic acid. The temperature was raised to 80°C under stirring, 126.4g potassium permanganate was added in three times, and the reaction was kept for 4 hours. Cool to room temperature and filter to obtain a colorless transparent filtrate. The filtrate was washed three times with 300g ethyl acetate, then acidified to pH=2 with concentrated hydrochloric acid, extracted three times with 750g ethyl acetate, the extract was washed with water, added with 12g anhydrous sodium sulfate and dried for 1 hour, filtered to remove the desiccant, and concentrated to obtain The crude product was rectified to obtain 96.0 g of product 2,2,3,3,4,4,5,5-octafluorovaleric acid, and its purity was 98.5% as measured by gas chromatography. The yield was 78.0%. Product IR v: 3219.8 (-COOH), 2997.4 (H-CF ...

Example Embodiment

[0022] Example 2

[0023] In a 2L three-necked flask were sequentially added 2,2,3,3,4,4,5,5-octafluoropentanol 116.0g, 700g water, and 200g acetic acid. The temperature was raised to 80°C under stirring, 142.2g potassium permanganate was added in three times, and the reaction was kept warm for 4 hours. Cool and filter to obtain a colorless transparent filtrate. The filtrate was washed three times with 300g dichloromethane, then acidified to pH=2 with concentrated hydrochloric acid, extracted three times with 750g dichloromethane, the extract was washed with water, added with 10g anhydrous magnesium sulfate, dried, filtered to remove the desiccant for 30 minutes, and the filtrate was concentrated The crude product was obtained, and 104.6 g of product 2,2,3,3,4,4,5,5-octafluorovaleric acid was obtained by rectification, and its purity was 98.0% as measured by gas chromatography. The yield was 85.1%.

Example Embodiment

[0024] Example 3

[0025] In a 2L three-necked flask were sequentially added 2,2,3,3,4,4,5,5-octafluoropentanol 116.0g, 700g water, and 200g acetic acid. The temperature was raised to 90°C under stirring, 158.0g potassium permanganate was added in three times, and the reaction was kept warm for 5 hours. Cool and filter to obtain a colorless transparent filtrate. The filtrate was washed with 300g of dichloroethane three times, then acidified with concentrated hydrochloric acid to pH=2, extracted with 750g of dichloroethane three times, the extract was washed with water, added with 12g of anhydrous sodium sulfate and dried for 2 hours, filtered to remove the desiccant, The filtrate was concentrated to obtain a crude product, and 111.4 g of product 2,2,3,3,4,4,5,5-octafluorovaleric acid was obtained by rectification, and its purity was 98.7% as measured by gas chromatography. The yield was 90.6%.

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Abstract

The invention discloses a preparation method of polyfluoro aliphatic carboxylic acid, which comprises the following concrete steps: oxidizing polyfluoro aliphatic alcohol by potassium permanganate to obtain polyfluoro carboxylic acid potassium salt, purifying intermediate products of fluorine-containing potassium carboxylate, namely washing for removing unreacted raw materials, and then, acidizing for releasing polyfluoro carboxylic acid. By utilizing the characteristic that the polyfluoro aliphatic alcohol is oxidized by the potassium permanganate to obtain the polyfluoro carboxylic acid, but the acidity of the polyfluoro carboxylic acid is further stronger than the acidity of acetic acid, so that the generated polyfluoro carboxylic acid is neutralized with potassium hydroxide released by the potassium permanganate in the reaction process to obtain the fluorine-containing carboxylic acid potassium salt, the invention adopts the method of firstly washing the fluorine-containing potassium carboxylate and then acidizing for releasing the polyfluoro carboxylic acid, thereby solving the problem that the polyfluoro aliphatic alcohol and the polyfluoro aliphatic carboxylic acid can not be rectified and separated easily. The polyfluoro aliphatic alcohol which is used as a raw material in the invention is prepared by telomerization of tetrafluoroethylene and belongs to an industrialized raw material. The process for preparing the polyfluoro aliphatic carboxylic acid by oxidizing the polyfluoro aliphatic alcohol has mild conditions and is suitable for industrialized production.

Description

technical field [0001] The invention relates to a synthesis method of polyfluoroaliphatic carboxylic acid surface-active compounds, in particular to a method for preparing polyfluoroaliphatic A method for carboxylic acid belongs to the field of fine chemical synthesis. Background technique [0002] Fluorocarbons are a class of fluorine-containing organic compounds with important application value, and their production and use can be traced back to 50 years ago. Due to its excellent chemical stability, weather resistance, corrosion resistance, heat resistance, pollution-free, oxidation resistance and other properties, it is widely used in textiles, paper, packaging, pesticides, carpets, leather, floor polishing, shampoo and fire extinguishing foam and other industrial and civil fields. [0003] Polyfluoroaliphatic carboxylic acid is a very important fluorocarbon. It can be used as surfactant, water-repellent and oil-repellent agent, and intermediate for synthesizing fluoro...

Claims

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Application Information

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IPC IPC(8): C07C51/16C07C53/21
Inventor 李战雄杜丽萍
Owner SUZHOU UNIV
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