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Preparation method of long-chain alkyl amidopropyl dimethylamine with CO2 responsiveness

A technology of alkyl acid amidopropyl dimethylamine and CO2, which is applied in the field of preparation and purification of long-chain alkyl acid amidopropyl dimethylamine, can solve the problem of not having good conversion efficiency and purification steps, high temperature, and no There are problems such as reaction catalyst, purification process and final product characterization, so as to achieve the effect of high yield, simple method and high product purity

Inactive Publication Date: 2017-12-08
CHINA UNIV OF PETROLEUM (EAST CHINA)
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Chinese patent CN201510792794 reports the reaction of erucic acid and propyl dimethylamine to generate erucamide propyl dimethylamine, but there is no specific reaction catalyst, purification process and characterization of the final product
Previous reports were limited by reaction catalysts and purification methods, required high temperature and did not have good conversion efficiency and purification steps

Method used

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  • Preparation method of long-chain alkyl amidopropyl dimethylamine with CO2 responsiveness
  • Preparation method of long-chain alkyl amidopropyl dimethylamine with CO2 responsiveness
  • Preparation method of long-chain alkyl amidopropyl dimethylamine with CO2 responsiveness

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1) Add stearic acid and N,N-dimethylaminopropylamine in a molar ratio of 1:1.1 into a three-necked flask with a condenser tube and a fractionating head, add sodium fluoride as a catalyst, and add calcium chloride as a catalyst in the fractionating head. The water remover is used to separate the by-product water in time, so that the reaction proceeds in the forward direction, and the condensation reaction is carried out under the protection of nitrogen gas, the reaction temperature is 130-150°C, and the reaction time is 8 hours.

[0030] 2) Then the unreacted dimethylaminopropylamine was removed by rotary evaporation, washed several times with a mixed solution of acetone and water ratio of 2:1 until colorless, filtered, and dried to obtain C 23 h 48 N 2 O White solid. Yield: 99%, 1 HNMR(400MHz,Chloroform-d)δ7.22s,(s,1H),3.47(J=2.6Hz,1H),2.28(J=9.4Hz,2H),2.11–1.95(8H),1.84(2H), 1.51 (2H), 1.13 (J=13.2Hz, 28H), 0.78 (J=6.1, 3H). Elemental analysis results: theoretical...

Embodiment 2

[0032] Add oleic acid and N,N-dimethylaminopropylamine in a molar ratio of 1:1.1 into a three-necked flask with a condenser and a fractionating head, add sodium fluoride as a catalyst, and add calcium chloride as a water remover in the fractionating head In order to separate the by-product water in time and make the reaction proceed in the direction of positive reaction, the condensation reaction is carried out under the protection of nitrogen gas, the reaction temperature is 130-150°C, and the reaction time is 8 hours. Then the unreacted dimethylaminopropylamine was removed by rotary evaporation, washed several times with a mixed solution of acetone and water at a ratio of 2:1 until colorless, separated, and dried to obtain C 23 h 46 N 2 O dark yellow liquid. Yield: 99%, 1 HNMR (400MHz, Chloroform-d) ppm: δ7.22 (s, 2H), 5.19 (J = 2.5Hz, 2H), 3.17 (J = 4.5Hz, 2H), 2.22 (J = 9.1, 6.4Hz, 3H) , 2.12–1.88 (10H), 1.87 (s, 3H), 1.69–1.22 (7H), 1.15 (J=13.2Hz, 20H), 0.74 (J=6.3, ...

Embodiment 3

[0034] Add palmitic acid and N,N-dimethylaminopropylamine in a molar ratio of 1:1.1 into a three-necked flask with a condenser tube and a fractionating head, add sodium fluoride as a catalyst, and add calcium chloride in the fractionating head as a dehydrator In order to separate the by-product water in time, the reaction proceeds to the forward reaction direction, and the condensation reaction is carried out under the protection of nitrogen gas, the reaction temperature is 130-150 ° C, and the reaction time is 8 hours. Then the unreacted dimethylaminopropylamine was removed by rotary evaporation, washed several times with a mixed solution of acetone and water at a ratio of 2:1 until colorless, filtered, and dried to obtain C 21 h 44 N 2 O white solid powder. Yield: 99%, 1HNMR(400MHz,Chloroform-d)ppm:δ7.20(s,1H),3.29(2H),2.38(2H),2.15(8H),1.51(2H),1.16-1.21(J=11.2Hz,26H) , 0.74 (t, J=4.7Hz, 3H). Elemental analysis results: theoretical value: C, 74.06; H, 13.02; N, 8.22; O,...

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Abstract

The invention provides a preparation method of long-chain alkyl amidopropyl dimethylamine with CO2 responsiveness, and relates to the preparation, purification and structure of several long-chain alkyl amidopropyl dimethylamine compounds with CO2 responsiveness as well as CO2 responsiveness characterization. The long-chain alkyl amidopropyl dimethylamine with CO2 responsiveness comprises palmitylamidopropyl dimethylamine, stearamidopropyl dimethylamine, oleamidopropyl dimethylamine and behenamidopropyl dimethylamine, and is low in preparation temperature, simple in the preparation method and high in the yield; and the aqueous solution of the long-chain alkyl amidopropyl dimethylamine has CO2 responsiveness, and phase transition can happen when CO2 is led in, so that the long-chain alkyl amidopropyl dimethylamine can be applied to reaction and separation with different polarity requirements, and the aqueous solution of the long-chain alkyl amidopropyl dimethylamine can be used as CO2-responsive gel. A compound prepared by the preparation method disclosed by the invention can also be used for increasing the recovery ratio of oil and gas fields.

Description

technical field [0001] The invention belongs to the technical field of oilfield exploitation products, and in particular relates to a method for preparing and purifying long-chain alkyl acid amidopropyl dimethylamine with CO2 responsive performance. Background technique [0002] The unique tertiary amine molecular structure of the end group of long-chain alkyl acid amidopropyl dimethylamine endows it with excellent CO 2 Responsive performance. by CO 2 Induction is a controllable system that can change the response of one physical property structure to another physical property structure. i.e. in CO 2 Under induction, the molecule can transform from a low-polarity structure to a high-polarity structure, which can be used in different reactions or separation processes that require solvents of different polarities. [0003] by CO 2 Induction, the end group of the long-chain alkyl acid amidopropyl dimethylamine changes from a weakly hydrophilic tertiary amine structure to a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/36C07C233/38C07C231/02C07C231/24C09K8/584C09K8/594C09K8/60C09K8/68C09K8/80C09K8/86
CPCC07C233/36C07C231/02C07C231/24C07C233/38C09K8/584C09K8/594C09K8/602C09K8/68C09K8/80C09K8/86C09K2208/30
Inventor 戴彩丽吴雪鹏赵明伟孙永鹏吴一宁赵光方丝丝李浩
Owner CHINA UNIV OF PETROLEUM (EAST CHINA)
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