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Preparation method of fluorine-containing non-ionic surface active agent and application

A surfactant, non-ionic technology, applied in the field of preparation of fluorine-containing surfactants, can solve the problems of refractory degradation, high bioaccumulation and toxicity to multiple organs of the human body, and achieves low cost, high practical value, high The effect of surface activity

Active Publication Date: 2014-03-26
湖北美畅环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, perfluorooctane sulfonyl compounds (PFOS) and perfluorooctanoic acid and its salts (PFOA), as the most widely used fluorocarbon surfactants, have attracted people's attention for their potential impact on the environment and human health; Experiments show that PFOS and PFOA hardly undergo any observable degradation under various physical and chemical conditions, and are currently one of the most difficult to degrade organic pollutants in the world, with high bioaccumulation and multi-organ toxicity in humans countries have successively banned its use

Method used

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  • Preparation method of fluorine-containing non-ionic surface active agent and application
  • Preparation method of fluorine-containing non-ionic surface active agent and application
  • Preparation method of fluorine-containing non-ionic surface active agent and application

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Preparation of nonionic fluorine-containing ionic surfactants.

[0021] Take 0.1mol perfluorobutylsulfonyl fluoride and 0.1mol N,N'-diethyl-1,3-propanediamine for amidation reaction, and use dichloromethane as solvent to obtain intermediate 1 (N-[3- (diethylammonia)-propyl] perfluorobutylsulfonamide), intermediate 1 uses acetone as solvent, reacts with ethylene oxide or chloroethanol to obtain intermediate 2 (N'-3-(diethyl )-propyl-(N-perfluorobutylsulfonyl-N-epoxy)-amine), intermediate 2 uses acetone as solvent to carry out ring-opening reaction with ethylene oxide to obtain non-ionic fluorine-containing surface active agent.

Embodiment 2

[0023] The synthesis of N-[3-(diethylamino)-propyl] perfluorobutylsulfonamide in embodiment 1

[0024] The synthesis process is as follows: In a three-neck round bottom flask equipped with a magnet, add an appropriate amount of dichloromethane, 0.03mol triethylamine and 0.1mol N,N′-diethyl-1,3-propanediamine, ice-water bath 0.1mol of perfluorobutylsulfonyl fluoride was added dropwise, and then reacted for 8 hours, and then rotary steamed to obtain a yellow oil, which was recrystallized with acetone to obtain a white crystal, the chemical expression of which was:

[0025]

[0026] MS(412.09); F 19 NMR: -85.952, -115.049, -123.705, -128.212; H 1 NMR: 2.322 (6H, -CH 3 ),3.502(2H,-CH 2 -),2.617(2H,-CH 2 -,),1.766(2H,-CH 2 -), 3.488 (-NH).

Embodiment 3

[0028] Synthesis of N'-3-(diethyl)-propyl-(N-perfluorobutylsulfonyl-N-epoxy)-amine in Example 1

[0029] The synthesis process is as follows: In a three-neck round bottom flask equipped with a magnet, add an appropriate amount of acetone, 0.1mol N-[3-(diethylammonia)-propyl]perfluorobutylsulfonamide, add a small amount of NaOH to adjust the pH From 7 to 8, add 0.1mol ethylene oxide dropwise in an ice-water bath, and then react for 6 hours. After rotary steaming, continue to bake to obtain a light yellow viscous substance. The product expression is:

[0030]

[0031] MS(456.11);H 1 NMR: 3.60(2H,-CH 2 -), 2.74(2H,-CH 2 -), 2.55(2H,-CH 2 -,), 2.36(2H,-CH 2 -), 2.40(4H,-CH 2 -), 1.51(2H,-CH 2 -),1.02(6H,-CH 3 ), 2.0 (-OH).

[0032] Minimum surface tension: 19.8 mN / m, CMC value 4 / 1000.

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Abstract

The invention discloses a preparation method of a fluorine-containing non-ionic surface active agent and an application. The preparation method comprises the steps of carrying out amidation reaction on perfluoroalkyl sulfuryl fluoride and N, N'-dimethyl (ethyl)-1, 3-propane diamine to obtain an intermediate 1; after refining, adopting acetone as a solvent to react with ethylene oxide or chlorethyl alcohol to obtain an intermediate 2 (N'-3-(dimethyl(ethyl))-propyl-(N-perfluorobutylsulfonyl-N-epoxy)-amine); carrying out ring-opening reaction on the intermediate 2 and ethylene oxide according to different proportions to obtain the fluorine-containing non-ionic surface active agent. The preparation method disclosed by the invention has the advantages that the production cost of the surface active agent is low, the preparation method is simple, the requirement on production equipment is low, and the production process is simple; the yield is high, the fluorine-containing monomer conversion rate reaches 93%; the surface performance is excellent, the lowest surface tension of certain compound to water is below 20mN / m and the HLB (Hydrophile Lipophile Balance) value of the surface active agent is easily changed.

Description

technical field [0001] The invention relates to a preparation method and application of a fluorine-containing surfactant, in particular to a preparation method and application of a class of fluorine-containing nonionic surfactants. Background technique [0002] Fluorocarbon surfactants are a class of special surfactants that have attracted much attention and obtained a lot of research results. They have outstanding characteristics such as high surface activity, high thermal stability and high chemical stability. However, perfluorooctane sulfonyl compounds (PFOS) and perfluorooctanoic acid and its salts (PFOA), as the most widely used fluorocarbon surfactants, have attracted people's attention for their potential impact on the environment and human health; Experiments show that PFOS and PFOA hardly undergo any observable degradation under various physical and chemical conditions, and are currently one of the most difficult to degrade organic pollutants in the world, with high...

Claims

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Application Information

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IPC IPC(8): B01F17/38B01F17/42B01F17/26B01F17/16C07C311/09C07C303/40C08G65/26C09K23/38C09K23/16C09K23/26C09K23/42
Inventor 龙光斗肖舒古丽米热·加帕黄澄华金广泉陈雪娟叶旭李菁
Owner 湖北美畅环保科技有限公司
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