Method for synthesizing betaine from long-chain tertiary amine by means of anhydrous quaternization under normal pressures

A long-chain tertiary amine and betaine technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of potential safety hazards and high equipment requirements, achieve high flash point, excellent performance, and inhibit hydrolysis The effect of product formation

Inactive Publication Date: 2016-05-11
PETROCHINA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this process needs to be carried out in a 3-10atm autocla

Method used

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  • Method for synthesizing betaine from long-chain tertiary amine by means of anhydrous quaternization under normal pressures
  • Method for synthesizing betaine from long-chain tertiary amine by means of anhydrous quaternization under normal pressures
  • Method for synthesizing betaine from long-chain tertiary amine by means of anhydrous quaternization under normal pressures

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 10

[0026] Example 1 Synthesis of octadecyl dimethyl hydroxypropyl sultaine under normal pressure anhydrous quaternization

[0027] In a 250mL three-necked flask equipped with a thermometer and a condensing reflux tube, add 29.7g of 0.1mol octadecyldimethyl tertiary amine, 21.6g of 0.11mol sodium trichlorodihydroxypropanesulfonate, 10mL ethylene glycol, 10mL1,2, -Propylene glycol, 5mL n-butanol, then place the three-necked flask in an oil bath at 125°C, turn on the magnetic stirrer, and detect the reaction by measuring the residual amine value. After 3 hours, the measured amine value is converted to a conversion rate of greater than 96%, closed flash point It is 75°C. figure 1 It is the ESI-MS spectrum of the product. The molecular ion peak at 436 m / z is the +H peak of octadecyl dimethyl hydroxypropyl sultaine (Mw 435).

Embodiment 2

[0028] Example 2 Synthesis of erucic acid acyl propyl dimethyl hydroxypropyl sultaine under normal pressure anhydrous quaternization

[0029] In a 250mL three-necked flask equipped with a thermometer and a condensing reflux tube, add 42.2g of 0.1mol octadecyldimethyl tertiary amine, 23.6g of 0.12mol sodium trichlorodihydroxypropanesulfonate, 10mL ethylene glycol, 15mL1,2. -Propylene glycol, 3mL n-pentanol, then place the three-necked flask in an oil bath at 135°C, turn on the magnetic stirrer, and detect the reaction by measuring the residual amine value. After 2.5 hours, the conversion rate of the measured amine value is greater than 95%, and the closed flash point It is 82°C. figure 2 It is the ESI-MS spectrum of the product. The molecular ion peak at 561 m / z is the +H peak of erucyl propyl dimethyl hydroxypropyl sulfobetaine (Mw 560).

Embodiment 3

[0030] Example 3 Synthesis of m-xylyl octadecyl dimethyl carboxy betaine under normal pressure anhydrous quaternization

[0031] In a 250mL three-necked flask equipped with a thermometer and a reflux tube, add 0.1 mol of m-xylyl octadecyl dimethyl tertiary amine 40.1 g, 0.13 mol sodium chloroacetate 15.2 g, 10 mL ethylene glycol, and 20 mL 1,2-propylene glycol. , 4mL n-butanol, then place the three-necked flask in a 140℃ oil bath, turn on the magnetic stirrer, and detect the reaction by measuring the residual amine value. After 3.5 hours, the conversion rate of the measured amine value is greater than 98%, and the closed flash point is 68 ℃. image 3 It is the ESI-MS spectrum of the product. The molecular ion peak at 460 m / z is the +H peak of meta-xylyl octadecyl dimethyl carboxy betaine (Mw 459).

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Abstract

The invention provides a method for synthesizing betaine from long-chain tertiary amine by means of anhydrous quaternization under normal pressures. The method includes a step of enabling the long-chain tertiary amine and chloro hydroxypropyl sodium sulfonate or chloroactic acid or sodium chloroacetate to react to each other in anhydrous mixed solvent systems under the conditions of the normal-pressures and the temperatures of 110-150 DEG C to generate long-chain betaine compounds. The method has the advantages that the method is particularly suitable for producing the displacement betaine compounds with long carbon chains, the reaction temperatures can be increased to reach 110-150 DEG C by the aid of the anhydrous mixed solvent systems under the normal pressures, and the reaction speeds and the conversion rates can be increased; generation of hydrolysis products under high-temperature conditions can be suppressed, the conversion rates can be higher than 95% by means of quaternization reaction of the tertiary amine with carbon chains higher than C18 within the reaction time of four hours, shortcomings of low flashing points and incapability of assisting solubilization of betaine with long carbon chains of conventional processes for synthesizing the betaine can be effectively overcome, and the betaine with the long carbon chains can be safely and efficiently produced by the aid of the method.

Description

Technical field [0001] The invention belongs to the technical field of surfactants, and in particular relates to a method for synthesizing betaine by anhydrous quaternization of long-chain tertiary amines under normal pressure. Background technique [0002] Betaine surfactant is an amphoteric surfactant. Its special structure determines its excellent ability and efficiency to reduce surface interfacial tension, and it has a wide range of application prospects in the field of tertiary oil recovery. The synthesis reaction of betaine surfactants (ie quaternization reaction) refers to the reaction of tertiary amine with chloroacetic acid (sodium) or sodium chlorohydroxypropyl sulfonate in a solvent to remove sodium chloride and generate the target product betaine Surfactant. Betaine BS12 commonly used in industry is made by reacting dodecyl tertiary amine and chloroacetic acid (sodium) in isopropanol aqueous solution at 80°C for 12 hours, with a conversion rate of about 90%. A larg...

Claims

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Application Information

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IPC IPC(8): C07C303/32C07C309/14C07C227/08C07C229/12C07C229/14C09K8/584
CPCC07C303/32C07C227/08C09K8/584C07C309/14C07C229/12C07C229/14
Inventor 周朝辉张群王红庄罗文利马德胜田茂章蔡红岩张帆
Owner PETROCHINA CO LTD
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