N-alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt and preparation method thereof

A technology of perfluoroalkylimidazoline and fluorocarbon imidazoline, which is applied in the field of N-alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt and its preparation, can solve the problem of sulfate-reducing bacteria without bactericidal performance and containing High cost of fluorosurfactants, ineffective corrosion inhibition and other problems, to achieve high thermodynamic stability and chemical stability, low pollution of three wastes, and not easy to hydrolyze

Inactive Publication Date: 2011-05-25
SHAANXI RES DESIGN INST OF PETROLEUM CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The purpose of the present invention is to overcome the shortcomings of traditional hydrocarbon imidazoline quaternary ammonium salts such as single application range, poor temperature resistance, insignificant corrosion inhibition effect, high toxicity, and no bactericidal performance against sulfate-reducing bacteria, and the conventional preparation of fluorine-containing surfactants Defects such as high cost, complex synthesis process, great environmental hazards, low product purity and difficult post-processing

Method used

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  • N-alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt and preparation method thereof
  • N-alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt and preparation method thereof
  • N-alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt and preparation method thereof

Examples

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Embodiment 1

[0028] In a 500ml stainless steel reactor equipped with a thermometer, agitator and pressure gauge, add 232g of perfluorononanoic acid, heat to 70°C and stir evenly, then add 78g of diethylenetriamine, add 1g of mesoporous alumina catalyst, and seal the reactor. The system was heated to 120°C, reacted for 8 hours under medium speed stirring, and cooled to room temperature within 2 hours without separation, directly added 64g of benzyl chloride and then heated to 100°C, and reacted for 10 hours under low speed stirring to obtain N-ethylamino-2- Perfluorononyl imidazoline quaternary ammonium salt. The N-ethylamino-2-perfluorononyl imidazoline quaternary ammonium salt structural formula that the present embodiment makes is shown in (1) (2), wherein R 1 for CF 3 -(CF 2 ) 8 , R 2 Ethyl N-alkylamino-2-perfluoroalkyl imidazoline quaternary ammonium salt.

Embodiment 2

[0030] In a 500ml stainless steel reaction kettle equipped with a thermometer, agitator and pressure gauge, add 207g of perfluorooctanoic acid, heat to 65°C and stir evenly, then add 80g of diethylenetriamine, add phosphotungstic acid / mesoporous alumina yttrium catalyst 1g, seal the reaction kettle. The system was heated to 120°C, reacted for 8 hours under medium speed stirring, and cooled to room temperature within 2 hours without separation, directly added 64g of benzyl chloride and then heated to 100°C, and reacted for 10 hours under low speed stirring to obtain N-ethylamino-2- Perfluoroheptyl imidazoline quaternary ammonium salt. The structural formula of the N-ethylamino-2-perfluoroheptyl imidazoline quaternary ammonium salt prepared in this embodiment is shown in (1) (2), wherein R 1 for CF 3 -(CF 2 ) 6 , R 2 Ethyl N-alkylamino-2-perfluoroalkyl imidazoline quaternary ammonium salt. The infrared spectrum and mass spectrum of the product are as follows figure 1 , 2...

Embodiment 3

[0038] In a 1000L stainless steel reaction kettle with temperature control, agitator and pressure gauge, add 157kg of perfluorocaproic acid, heat to 65-70°C and stir evenly, then add 124kg of diethylenetriamine, and add 500g of zirconate heteropolyacid catalyst , Airtight reactor. Heat the system to 110-120°C, react for 8-10 hours under medium-speed stirring, and then cool down to room temperature within 2 hours without separation, directly add 126kg of dimethyl sulfate and heat up to 100-110°C, and react for 8-10 hours under low-speed stirring 10h, the obtained N-ethylamino-2-perfluorohexyl imidazoline quaternary ammonium salt. The N-ethylamino-2-perfluorohexyl imidazoline quaternary ammonium salt structural formula that the present embodiment makes is shown in (1) (2), wherein R 1 for R 1 for CF 3 -(CF 2 ) 5 , R 2 for R2 Ethyl N-alkylamino-2-perfluoroalkyl imidazoline quaternary ammonium salt.

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Abstract

The invention relates to N-alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt and a preparation method thereof. The N-alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt has molecular structural formulas shown as a formula (1) and a formula (2), wherein R1 is CF3-(CF2)n, and n is between 3 and 11; and R2 is one of C1-10 alkyl, C2-10 alkenyl, C3-7 cycloalkyl or any substituted aryl group, aralkyl group or heteroaryl group. The preparation method comprises the steps of: reacting polyenoid polyamine and perfluorocarboxylic acid serving as raw materials, and aluminum oxide, heteropolyacid, heteropolyacid / aluminum oxide, and phosphotungstic acid / mesoporous yttrium aluminum oxide serving as a catalyst for 7 to 12h at the temperature of between 90 and 150 DEG C to obtain fluorocarbon imidazoline, and then reacting the fluorocarbon imidazoline with a quaternization agent in a molar ratio of 1: (1-3) for 6 to 12h at the temperature of between 60 and 150 DEG C to obtain the N-alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt. The method has the characteristics of mild reaction conditions, high yield, less three wastes, easily obtained raw materials, suitable industrialized production and 'environment-friendly chemical' synthesis.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to N-alkylamino-2-perfluoroalkyl imidazoline quaternary ammonium salt and a preparation method thereof. The structural formula of N-alkylamino-2-perfluoroalkyl imidazoline quaternary ammonium salt is shown in the following formula (1,2), where R 1 for CF 3 -(CF 2 ) n , n=3~11; R 2 for C 1-10 Alkyl, C 2-10 Alkenyl, C 3-7 Cycloalkyl or optionally substituted aryl, aralkyl or heteroaryl. [0002] [0003] where n≥1 [0004] (1) [0005] [0006] where n≥1 [0007] (2) Background technique [0008] N-Alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt is an important fluorocarbon surfactant, because its hydrophobic chain is a fluorocarbon chain, that is, the carbon-carbon bond is replaced by a fluoro-carbon bond with a strong electronegativity Bond, so that it has good surface activity, high thermodynamic stability and chemical stability and strong bactericid...

Claims

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Application Information

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IPC IPC(8): C07D233/20B01F17/32C23F11/00A01P1/00C09K23/32
Inventor 陈晓东张向东刘世川程雯刘彦峰王喜叶
Owner SHAANXI RES DESIGN INST OF PETROLEUM CHEM IND
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