A kind of p-toluenesulfonate group gemini quaternary ammonium salt and preparation method thereof

A technology of p-toluenesulfonate and gemini quaternary ammonium salt, which is applied in the direction of sulfonate ester preparation, amino compound preparation, chemical instruments and methods, etc. It can solve the problem of sudden drop in molecular weight, lower corrosion inhibition performance, and can not really meet the requirements of environmental protection and other problems, to achieve the effect of rapid response, increased reaction rate, and not easy to decompose

Active Publication Date: 2017-11-21
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as a corrosion inhibitor, the sudden drop of its molecular weight leads to the obstruction of the arrangement of the molecular film on the metal surface. Although its degradation performance is improved, its corrosion inhibition performance is reduced.
[0006] The problem that plagues the development of ester-based gemini quaternary ammonium salts is that the degradation can only be decomposed in a small range, and cannot really meet the requirements of environmental protection

Method used

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  • A kind of p-toluenesulfonate group gemini quaternary ammonium salt and preparation method thereof
  • A kind of p-toluenesulfonate group gemini quaternary ammonium salt and preparation method thereof
  • A kind of p-toluenesulfonate group gemini quaternary ammonium salt and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] see figure 1 , 1) Add the weighed 0.02mol of dodecyldimethyl tertiary amine into a 100mL three-necked flask filled with 10mL of isopropanol, heat to 50°C, and then drop 4.0mL of 2.5mol / L hydrochloric acid into it Solution, stirred at 450r / min until uniform. Gradually add 0.01mol of epichlorohydrin to the system dropwise within 30 minutes, and adopt a temperature program at the same time. After 12 hours, the heating was stopped to obtain a crude product. The crude product was evaporated under reduced pressure at 85°C and 0.09MPa to remove the solvent, then dissolved in acetone at 60°C, recrystallized at room temperature, filtered with suction, and redissolved. After repeating three times, dry to obtain hydroxypropyl gemini quaternary ammonium salt; the yield is 87.9%.

[0035] 2) Add 0.01mol of the intermediate product hydroxypropyl gemini quaternary ammonium salt and 0.01mol of p-toluenesulfonyl chloride into a 100mL flask containing 20mL of chloroform, and after stir...

Embodiment 2

[0037]1) Add 0.02mol of dodecyldimethyl tertiary amine into a 100mL three-necked flask filled with 10mL of isopropanol, heat to 50°C, and then drop 4.0mL of 2.5mol / L hydrochloric acid solution into it , Stir at 450r / min until uniform. Gradually add 0.01mol of epichlorohydrin to the system dropwise within 30 minutes, and adopt a temperature program at the same time. After 12 hours, the heating was stopped to obtain a crude product. The crude product was evaporated under reduced pressure at 85°C and 0.09MPa to remove the solvent, then dissolved in acetone at 60°C, recrystallized at room temperature, filtered with suction, and redissolved. After repeating three times, dry to obtain hydroxypropyl gemini quaternary ammonium salt; the yield is 89.13%.

[0038] 2) Add 0.01mol of the intermediate product hydroxypropyl gemini quaternary ammonium salt and 0.01mol of p-toluenesulfonyl chloride into a 100mL flask containing 20mL of chloroform, and after stirring evenly, slowly add dropwi...

Embodiment 3

[0040] 1) Add 0.021mol of dodecyldimethyl tertiary amine into a 100mL three-neck flask filled with 10mL of isopropanol, heat to 50°C, and then drop 4.0mL of 2.5mol / L hydrochloric acid solution into it , Stir at 450r / min until uniform. Gradually add 0.01mol of epichlorohydrin to the system dropwise within 30 minutes, and adopt a temperature program at the same time. After 12 hours, the heating was stopped to obtain a crude product. The crude product was evaporated under reduced pressure at 85°C and 0.09MPa to remove the solvent, then dissolved in acetone at 60°C, recrystallized at room temperature, filtered with suction, and redissolved. After repeating three times, dry to obtain hydroxypropyl gemini quaternary ammonium salt; the yield is 92.1%.

[0041] 2) Add 0.01mol of the intermediate product hydroxypropyl gemini quaternary ammonium salt and 0.013mol of p-toluenesulfonyl chloride into a 100mL flask containing 20mL of chloroform, stir evenly, and slowly add dropwise at 60°C...

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Abstract

The invention relates to a p-toluenesulfonate-group Gemini quaternary ammonium salt and a preparation method thereof. The preparation method comprises the following steps: adding long-chain alkyl tertiary amine and isopropanol into a container, heating, and dropwisely adding hydrochloric acid; after the dropwise addition, stirring uniformly, dropwisely adding epoxy chloropropane into the container, and reacting to obtain the hydroxypropyl Gemini quaternary ammonium salt; and adding the hydroxypropyl Gemini quaternary ammonium salt and paratoluensulfonyl chloride into a solvent, stirring uniformly, dropwisely adding a NaOH solution while stirring until the reaction is completed, stopping stirring, and heating to obtain the p-toluenesulfonate-group Gemini quaternary ammonium salt. The p-toluenesulfonate-group Gemini quaternary ammonium salt simultaneously has two hydrophilic quaternary ammonium salt groups; and the plane structure of the p-toluenesulfonate-group benzene ring in the linking group, the lone electron pair of heteroatoms in the sulfonate group and the metal surface can easily form a coordinate bond, so that the molecules form a film on the iron pipe wall, thereby facilitating the corrosion inhibition effect on the steel pipeline. The sulfonate group can not be easily hydrolyzed and decomposed in water, and thus, can not further pollute the water body.

Description

technical field [0001] The invention relates to a preparation method of a gemini quaternary ammonium salt, in particular to a p-toluenesulfonate group gemini quaternary ammonium salt and a preparation method thereof. Background technique [0002] Gemini surfactant is a new type of surfactant that connects two traditional surfactant molecules by chemical bonds at or near the head group through a special linking group. [0003] Ester-based gemini surfactants are easily hydrolyzed into non-surface active fragments due to the ester group structure in the hydrophobic chain, and have good biodegradability and excellent surface activity. Therefore, it is a good chemical intermediate and a surfactant with good performance. [0004] Chinese patent CN 104262182 A mixes a halogenated carboxylic acid or a halogenated acetyl halide and a long-carbon chain alcohol in a certain proportion under solvent-free conditions, and reacts to obtain an α-halogenated carboxylic acid ester. Then mix...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/73C07C303/28
CPCC07C209/12C07C303/28C07C309/73C07C211/63
Inventor 郭睿李欢乐刘爱玉甄建斌杨江月李晓芳程敏王超
Owner SHAANXI UNIV OF SCI & TECH
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