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Preparation method and application of amphoteric fluorinion-containing ionic surfactant

A surfactant and zwitterion technology is applied in the field of preparation of fluorine-containing surfactants, which can solve the problems of refractory organic pollutants, high bioaccumulation and toxicity to multiple organs of the human body, and achieve high surface activity and productivity. High and excellent surface properties

Inactive Publication Date: 2012-06-13
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, perfluorooctane sulfonyl compounds (PFOS) and perfluorooctanoic acid and its salts (PFOA), which are widely used at present, have attracted people's attention for their potential impact on the environment and human health. Various experiments have shown that PFOS and PFOA are Almost no observable degradation will occur under various physical and chemical conditions. It is currently one of the most difficult to degrade organic pollutants in the world. It has high bioaccumulation and multi-organ toxicity in the human body. Its use has been banned in various countries.

Method used

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  • Preparation method and application of amphoteric fluorinion-containing ionic surfactant
  • Preparation method and application of amphoteric fluorinion-containing ionic surfactant
  • Preparation method and application of amphoteric fluorinion-containing ionic surfactant

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Amphoteric fluoride ion surfactant preparation.

[0025] Get 1mol perfluorobutylsulfonyl fluoride and 1mol N,N'-dimethyl-1,3-propanediamine to carry out amidation reaction, use benzene as solvent to obtain intermediate (N-[3-(dimethyl Ammonia)-propyl] perfluorobutylsulfonamide), recrystallized with ethanol and then amidated with octylsulfonyl chloride, using acetone as solvent to obtain the intermediate (N'-3-(dimethyl)- Propyl-(N-perfluorobutylsulfonyl-N-octylsulfonyl)-imine), ethanol as solvent, with sodium chloroacetate or sodium chloroethylsulfonate or sodium α-hydroxychloropropylsulfonate Reaction to obtain N'-3-(dimethyl)-propyl-(N-perfluorobutylsulfonyl-N-octylsulfonyl)-imine carboxylic acid betaine, N'-3-(two Methyl)-propyl-(N-perfluorobutylsulfonyl-N-octylsulfonyl)-iminosulfonic acid betaine, N′-3-(dimethyl)-propyl-(N- Perfluorobutylsulfonyl-N-octylsulfonyl)-iminohydroxysulfonic acid betaine, etc.

Embodiment 2

[0027] The synthesis of N-[3-(dimethylamino)-propyl] perfluorobutylsulfonamide in embodiment 1

[0028] The synthesis process is as follows: In a three-necked round bottom flask equipped with a magnet, add 100ml of benzene, 1mol of triethylamine and 1mol of N,N'-dimethyl-1,3-propanediamine, and drop 1mol of Perfluorobutylsulfonyl fluoride, then reacted for 8 hours, filtered with suction, and recrystallized with ethanol to obtain white crystals, the chemical expression of which is:

[0029]

[0030] MS(384);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

[0032] Synthesis of N'-3-(dimethyl)-propyl-(N-perfluorobutylsulfonyl-N-octylsulfonyl)-imine in Example 1

[0033] The synthesis process is as follows: In a three-neck round bottom flask equipped with a magnet, add 100ml of acetone, 1mol of triethylamine and 1mol of N-[3-(dimethylammonia)-propyl]perfluorobutylsulfonamide, after dissolving Add 1 mol of octylsulfonyl chloride dropwise, then react for 6 hours, filter with suction, and recrystallize to obtain white (or light yellow) crystals. The product expression is:

[0034]

[0035] MS(561.2); F 19 NMR: -85.932, -115.041, -123.694, -128.022; H 1 NMR: 3.419 (2H, -CH 2 -), 2.316 (6H, -CH 3 ), 2.608 (2H, -CH 2 -,), 1.721 (2H, -CH 2 -), 3.412 (2H, -CH 2 -), 1.856 (2H, -CH 2 -), 1.294 (10H, -CH 2 -,), 1.022 (3H, -CH 3 ).

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Abstract

The invention discloses a preparation method and application of amphoteric fluorinion-containing ionic surfactant. The method comprises the following steps of: performing amidation on perfluoroalkyl sulfuryl fluoride and N, N'-dimethyl (diethyl)-1,3-propane diamine to obtain an intermediate 1, refining, performing amidation on a refined intermediate 1 and alkyl sulfuryl fluoride (chloride) or alkyl acyl fluoride (chloride) to obtain an intermediate 2, refining, and reacting the refined intermediate 2 and sodium chloroacetate and other substances to obtain the fluorinion-containing imine amphoteric ionic surfactant; and the surfactant can be used as emulsifier, foam stabilizer in a high-efficiency foam extinguishing agent, a wetting agent, a dispersing agent, a metal surface treatment agent, fire extinguishing agent additive, a foam flotation agent, and a crude oil evaporation inhibitor. The invention has the advantages that: the surfactant is low in production cost, and has low requirements on production equipment; the preparation method is simple; a product is environment-friendly, high in yield, excellent in surface property; the conversion rate of fluorinion-containing monomer reaches 96 percent; and the minimum surface tension of certain compounds on water is less than 17mN / m.

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 amphoteric betaine-type ionic surfactants. Background technique: [0002] Commonly used surfactants, whose hydrophobic groups are hydrocarbon groups, may also contain other elements such as oxygen, sulfur, nitrogen, chlorine, bromine, iodine, etc., such commonly used surfactants are called ordinary surfactants . Surfactants containing elements such as fluorine, phosphorus, silicon and boron in the surfactant molecule are called special surfactants. 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. [0003] Fluorocarbon surfactants are divided into four categories:...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/26B01F17/16B01F17/18B01F17/28C07C311/09C07C311/48C07C311/51C07C303/40A62D1/02C09K23/26C09K23/16C09K23/18C09K23/28
Inventor 龙光斗付冬梅肖舒古丽米热李中华黄澄华李训生罗必新周烈平
Owner HUAZHONG NORMAL UNIV
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