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Synthesis method of tertiary aliphatic amine

A technology for the synthesis of fatty tertiary amines, which is applied in the field of surfactant intermediates and their preparation, and the synthesis of fatty tertiary amines, which can solve the problems of low cost, high reaction temperature, and high cost of raw materials, and achieve complete reaction and simple synthesis process , the effect of high yield

Active Publication Date: 2014-08-06
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the industry mainly adopts the direct amination method of alcohol, which is to directly aminate fatty alcohol in the presence of a catalyst. high
For the fatty acid method, fatty acid is mostly used as raw material at present, aminated and dehydrated into fatty nitrile (200-360°C), and then methylated to obtain fatty tertiary amine (120-230°C, 1.38-7.0MPa); or with Dimethylamine undergoes amidation reaction to generate N,N-dimethylalkylamide (200-290°C, 3-14MPa), which is then reduced to the corresponding N,N-dimethylalkyl tertiary amine by catalytic hydrogenation. Although this method has low cost of raw materials, the reaction needs to be carried out under high temperature and high pressure.

Method used

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  • Synthesis method of tertiary aliphatic amine
  • Synthesis method of tertiary aliphatic amine
  • Synthesis method of tertiary aliphatic amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Synthesis of N,N-dimethyl-(9 or 10-phenyl) heptadecyl tertiary amine

[0039] N,N-Dimethyl-(9 or 10-phenyl)heptadecyl tertiary amine

[0040]

[0041] (wherein, m=5, n=1 or 2, j=8 or 7, m+n+j=14) synthesized according to the following steps:

[0042] (1) At 15°C, mix 9 or 10-phenyl-octadecanoic acid amide (methanol solution) with 7.5 mL sodium hypochlorite solution (active chlorine ≥ 5.2%, NaOH content 7-8%) in a molar ratio of 1:1.5 The reaction was carried out, stirred for 1 h, then heated to 55° C., and reacted for another 4 h to generate methyl (9 or 10-phenyl)heptadecylcarbamate.

[0043] (2) Add 3.6 g of sodium hydroxide (4.5 mol / L) to the methanol solution of methyl (9 or 10-phenyl) heptadecylcarbamate, and react at 85°C for 8 h. After the reaction, the excess is removed by evaporation. of methanol, then add an appropriate amount of water, and separate the upper layer material to obtain (9 or 10-phenyl) heptadecylamine. Its GC-MS spectrum is shown ...

Embodiment 2

[0045] Example 2 Synthesis of N,N-dimethyl-(9 or 10-phenyl) heptadecyl tertiary amine

[0046] (1) At 15°C, mix the methanol solution of 9 or 10-phenyl-octadecanoic acid amide with 7.5 mL of sodium hypochlorite solution (active chlorine ≥ 5.2%, NaOH content 7-8%) in a molar ratio of 1:1.5 The reaction was carried out, stirred for 1 h, then heated to 55° C., and reacted for another 4 h to generate methyl (9 or 10-phenyl)heptadecylcarbamate.

[0047] (2) Add 3.6 g of sodium hydroxide (4.5 mol / L) to the methanol solution of methyl (9 or 10-phenyl) heptadecylcarbamate, and react at 85°C for 8 h. After the reaction, the excess is removed by evaporation. The methanol was added to the appropriate amount of water, and the upper layer was separated to obtain (9 or 10-phenyl) heptadecylamine.

[0048] (3) Mix (9 or 10-phenyl) heptadecylamine with 1.2 mL formaldehyde solution (HCHO content 37.0-40.0%), 1.8 mL glacial acetic acid and 1.04 g zinc powder in a molar ratio of 1:2:4:2 The mi...

Embodiment 3

[0049] Example 3 Synthesis of N,N-dimethyl-(9 or 10-phenyl) heptadecyl tertiary amine

[0050] (1) At 15°C, mix 9 or 10-phenyl-octadecanoic acid amide (methanol solution) with 7.5 mL sodium hypochlorite solution (active chlorine ≥ 5.2%, NaOH content 7-8%) in a molar ratio of 1:1.5 The reaction was carried out, stirred for 1 h, then heated to 55° C., and reacted for another 4 h to generate methyl (9 or 10-phenyl)heptadecylcarbamate.

[0051] (2) Add 3.6 g of sodium hydroxide (4.5 mol / L) to the methanol solution of methyl (9 or 10-phenyl) heptadecylcarbamate, and react at 85°C for 8 h. After the reaction, the excess is removed by evaporation. The methanol was added to the appropriate amount of water, and the upper layer was separated to obtain (9 or 10-phenyl) heptadecylamine.

[0052] (3) Mix (9 or 10-phenyl) heptadecylamine with 1.2 mL formaldehyde solution (HCHO content 37.0-40.0%), 1.8 mL glacial acetic acid and 1.04 g zinc powder in a molar ratio of 1:2:4:2 The mixture was ...

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Abstract

The invention provides a synthesis method of tertiary aliphatic amine. By adopting the method disclosed by the invention, fatty acid amide is taken as a raw material, and the tertiary aliphatic amine is synthesized by Hofmann degradation and reaction for reducing methylation. The synthesis method has the advantages of simple synthesis process, mild reaction conditions, complete reaction, few side reactions, low energy consumption and high yield.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, relates to a surfactant intermediate and its preparation, in particular to the synthesis of a fatty tertiary amine, which can be applied to the synthesis of amphoteric surfactants. Background technique [0002] Long-chain aliphatic tertiary amines, especially N,N-dimethylalkyl tertiary amines, are important intermediates for the synthesis of cationic surfactants and amphoteric surfactants. Most of the cationic surfactants and zwitterionic surfactants are Is a derivative of aliphatic tertiary amines. The synthesis methods of fatty tertiary amines mainly include fatty alcohol method and fatty acid method. At present, the direct amination method of alcohol is mainly used in the industry. This method is to directly aminate aliphatic alcohols in the presence of a catalyst, which not only requires a catalyst with high activity and high selectivity, but also has a high reaction temperature (180-230°C)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/28C07C213/08C07C211/27C07C215/28C07C211/08
Inventor 牟伯中杨世忠刘金峰刚洪泽罗全迁
Owner EAST CHINA UNIV OF SCI & TECH
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