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Fluorine-containing chelating agent and its preparation method and application

A chelating agent and reaction technology, applied in the field of fluorine-containing chelating agent and its preparation, can solve the problems of poor solvency, high operating pressure, low extraction efficiency, etc., achieve low extraction pressure, reduce energy consumption and operating costs, and improve extraction efficiency high effect

Active Publication Date: 2015-12-09
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] A technical problem to be solved by the present invention is to overcome the shortcomings of existing chelating agents such as poor solubility in supercritical carbon dioxide, low extraction efficiency, high operating pressure and narrow application range in the application of supercritical carbon dioxide extraction, and provide a A fluorine-containing chelating agent with excellent solubility in supercritical carbon dioxide, strong chelating effect on metal ions, and low operating pressure in supercritical carbon dioxide extraction applications

Method used

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  • Fluorine-containing chelating agent and its preparation method and application
  • Fluorine-containing chelating agent and its preparation method and application
  • Fluorine-containing chelating agent and its preparation method and application

Examples

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Embodiment 1

[0026] Taking the preparation of the fluorine-containing chelating agent of the following formula as an example, its specific preparation method is as follows:

[0027]

[0028] 1. Synthesis of diethyl iminodiacetate

[0029] Under nitrogen protection and condensing reflux, add 71.4g (0.6mol) of thionyl chloride dropwise into a round-bottomed flask containing 33.3g (0.25mol) of iminodiacetic acid, heat to 45°C under stirring, and react at a constant temperature After 5 hours, add 117mL (2mol) of ethanol, raise the temperature to 60°C and react at this temperature for 12 hours, after distilling off excess ethanol, then distill under reduced pressure to obtain 45.6g of diethyl iminodiacetate, the yield is 92%.

[0030] 2. Synthesis of fluorine-containing chelating agent

[0031] Under nitrogen protection and condensing reflux, 49.8g (0.10mol) hexafluoropropylene oxide trimer (CF 3 CF 2 CF 2 OCF (CF 3 ) CF 2 OCF (CF 3 ) COF, provided by Zhejiang Huanxin Fluorine Materi...

Embodiment 2

[0037] Taking the preparation of the fluorine-containing chelating agent of the following formula as an example, its specific preparation method is as follows:

[0038]

[0039] The synthesis of diethyl iminodiacetate in this example is the same as in Example 1. In step 2 of synthesizing a fluorine-containing chelating agent, 100 g (0.025 mol) of polyhexafluoro Propylene oxide (CF 3 CF 2 CF 2 O(CF(CF 3 ) CF 2 O) 22 CF(CF 3 ) COCl, the average degree of polymerization is 24, by the corresponding polyhexafluoropropylene oxide (CF) containing carboxylic acid end group 3 CF 2 CF 2 O(CF(CF 3 ) CF 2 O) 22 CF(CF 3 )COOH) and thionyl chloride were synthesized according to the method reported in the literature (J.Mater.Res., 1995,10,3,530-537), in which polyhexafluoropropylene oxide containing carboxylic acid end groups was provided by DuPont, USA) Put 5.68g (0.03mol) of diethyl iminodiacetate and 1.73g (0.0125mol) of anhydrous potassium carbonate into a round-bottomed ...

Embodiment 3

[0044] Taking the preparation of the fluorine-containing chelating agent of the following formula as an example, its specific preparation method is as follows:

[0045]

[0046] The synthesis of diethyl iminodiacetate in this example is the same as in Example 1. In step 2 of synthesizing a fluorine-containing chelating agent, under nitrogen protection and condensing reflux, 140 g (0.02 mol) of polyhexafluoro Propylene oxide (CF 3 CF 2 CF 2 O(CF(CF 3 ) CF 2 O) 40 CF(CF 3 ) COCl, the average degree of polymerization is 42, by the corresponding polyhexafluoropropylene oxide (CF) containing carboxylic acid end group 3 CF 2 CF 2 O(CF(CF 3 ) CF 2 O) 40 CF(CF 3 )COOH) and thionyl chloride were synthesized according to the method reported in the literature (J.Mater.Res., 1995,10,3,530-537), in which polyhexafluoropropylene oxide containing carboxylic acid end groups was provided by DuPont, USA) Put 4.75g (0.025mol) iminodiacetic acid diethyl ester and 2.1g (0.015mol) a...

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Abstract

The invention discloses a fluorine-containing chelating agent and a preparation method and application thereof. The structural formula of the fluorine-containing chelating agent is shown in the specification; and the preparation method comprises the following steps: with iminodiacetic acid as a reaction substrate, protecting carboxyl through an esterification reaction between carboxyl and alcohol; establishing a basic skeleton of the fluorine-containing chelating agent through an amidation reaction between imino group and fluorine-containing acyl halide or an amination reaction between imino group and fluorine-containing halogenated hydrocarbon; and de-protecting for releasing carboxyl through a hydrolysis reaction of ester. The fluorine-containing chelating agent disclosed by the invention has good dissolving property in supercritical carbon dioxide, can be mixed and dissolved in the supercritical carbon dioxide under mild conditions, has a strong chelating effect on metal ions and can be applied to the extraction of heavy metal ions from the supercritical carbon dioxide medium, also can be used in the purifying treatment and resource recycling of pollutants such as wastewater, soil and electronic waste containing heavy metal ions and used for cleaning high-precision electronic devices such as small-size integrated circuits and the like.

Description

technical field [0001] The invention belongs to the technical field of green chemistry and chemical engineering, and in particular relates to a fluorine-containing chelating agent and its preparation method and application. Background technique [0002] While the rapid development of industry has brought enormous wealth to human beings, it has also had severe negative impacts on the environment. A large amount of waste liquid and slag discharged in the production process and a large amount of electronic waste generated in the consumption process contain a considerable amount of heavy metal ions. The pollution of the above-mentioned heavy metal ions to the natural environment such as water body and soil is shocking. For heavy metal ion pollutants, traditional treatment methods (such as landfill method and chemical precipitation method, etc.) can alleviate or eliminate the problem of ground environmental pollution to a certain extent in a small range, but the secondary polluti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/12C07C233/47C07C231/12C08G65/333C02F1/58B09C1/02B09C1/08C02F101/10C02F101/20
CPCY02P20/544Y02P20/54
Inventor 陈建刚刘昭铁郭金龙王宽沈淑坤刘忠文江金强郝郑平
Owner SHAANXI NORMAL UNIV
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