Preparation method of gemini amine oxide containing alkyl group, ester group and ethyl group

A technology of alkyl ester and amine oxide, applied in organic chemistry and other directions, can solve the problems of uneasy control of reaction conditions, unenvironmental protection, residues, etc., and achieve the effects of convenient production process, low irritation and mild synthesis conditions

Inactive Publication Date: 2019-05-07
BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, most of the synthesis techniques of geminiamine oxides use highly toxic and corrosive alkyl halides, acyl halides, and dihalides as raw materials to obtain products through Schotten-Baumann condensation reactions, etc., and the reaction conditions are not easy. Control, and not environmentally friendly, and there will be a certain amount of residue in the product, so that the surfactant product will inevitably have a certain degree of irritation and toxicity

Method used

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  • Preparation method of gemini amine oxide containing alkyl group, ester group and ethyl group
  • Preparation method of gemini amine oxide containing alkyl group, ester group and ethyl group
  • Preparation method of gemini amine oxide containing alkyl group, ester group and ethyl group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] (1) Preparation of N,N'-dimethyl-bis(2-hydroxyethyl)-ethylenediamine

[0018] Add 0.1mol N,N'-bis(2-hydroxyethyl)-ethylenediamine and 30mL methanol into a 250mL three-necked flask, slowly add 0.7mol formic acid dropwise while stirring, and then slowly dropwise add 0.6mol formaldehyde aqueous solution, and heat to 70 ℃, constant temperature reaction 4h. After the reaction is completed, cool to room temperature, add NaOH to fully dissolve the solid, adjust the pH value to 10-12, precipitate a white solid, filter with suction, and dry to obtain N,N'-dimethyl-bis(2-hydroxyethyl)- Ethylenediamine.

[0019] (2) Preparation of N,N'-dimethyl-bis(2-lauryl ester ethyl)-ethylenediamine

[0020] Add 0.1mol N,N'-dimethyl-bis(2-hydroxyethyl)-ethylenediamine, 0.3mol lauric acid and 30mL dichloromethane into a 250mL round-bottom flask. After stirring for 10min at room temperature, add 0.3mol bicyclic Hexylcarbodiimide and 0.5wt% 4-dimethylaminopyridine as the reaction substrate are used as...

Embodiment 2

[0024] (1) Preparation of N,N'-dimethyl-bis(2-hydroxyethyl)-ethylenediamine

[0025] Add 0.1mol N,N'-bis(2-hydroxyethyl)-ethylenediamine and 30mL methanol into a 250mL three-necked flask, slowly add 0.7mol formic acid dropwise while stirring, and then slowly dropwise add 0.6mol formaldehyde aqueous solution, and heat to 70 ℃, constant temperature reaction 4h. After the reaction is completed, cool to room temperature, add NaOH to fully dissolve the solid, adjust the pH value to 10-12, precipitate a white solid, filter with suction, and dry to obtain N,N'-dimethyl-bis(2-hydroxyethyl)- Ethylenediamine.

[0026] (2) Preparation of N,N'-dimethyl-bis(2-myristyl ester ethyl)-ethylenediamine

[0027] Add 0.1mol N,N'-dimethyl-bis(2-hydroxyethyl)-ethylenediamine, 0.3mol myristic acid and 30mL dichloromethane into a 250mL round-bottomed flask. After stirring for 10min at room temperature, add 0.3mol Cyclohexylcarbodiimide and 0.5wt% 4-dimethylaminopyridine as a reaction substrate are used as...

Embodiment 3

[0031] (1) Preparation of N,N'-dimethyl-bis(2-hydroxyethyl)-1,3-propanediamine

[0032] Add 0.1mol N,N′-bis(2-hydroxyethyl)-1,3-propanediamine and 30mL methanol into a 250mL three-necked flask, slowly add 0.7mol formic acid dropwise while stirring, and then slowly dropwise add 0.6mol formaldehyde aqueous solution. , Heat to 70°C and react at constant temperature for 4h. After the reaction is completed, cool to room temperature, add NaOH to fully dissolve the solid, adjust the pH value to 10-12, precipitate a white solid, filter with suction, and dry to obtain N,N'-dimethyl-bis(2-hydroxyethyl)- 1,3-propanediamine.

[0033] (2) Preparation of N,N'-dimethyl-bis(2-palmityl ester ethyl)-1,3-propanediamine

[0034] Add 0.1mol N,N'-dimethyl-bis(2-hydroxyethyl)-1,3-propanediamine, 0.3mol palmitic acid and 30mL dichloromethane into a 250mL round bottom flask. After stirring for 10min at room temperature, add 0.3 mol of dicyclohexylcarbodiimide and 0.5 wt% of 4-dimethylaminopyridine as a re...

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Abstract

The invention discloses a preparation method of gemini amine oxide containing an alkyl group, an ester group and an ethyl group, and belongs to the technical field of organic compound synthesis. The preparation method of the gemini amine oxide containing the alkyl group, the ester group and the ethyl group comprises reaction of N,N'-bis(2-hydroxyethyl)-ethylenediamine or N,N'-bis(2-hydroxyethyl)-1,3-propanediamine with formaldehyde and formic acid to obtain a hydroxyethyl-containing bis-tertiary amine, dehydration and esterification of the bis-tertiary amine with a fatty acid and dicyclohexylcarbodiimide and 4-dimethylaminopyridine to obtain a bis-tertiary amine containing an alkyl group, an ester group and an ethyl group, reaction of the bis-tertiary amine containing the alkyl group, theester group and the ethyl group with hydrogen peroxide to generate the gemini amine oxide containing the alkyl group, the ester group and the ethyl group. The gemini amine oxide containing the alkyl group, the ester group and the ethyl group has the advantages of excellent surface activity, low irritation, low toxicity and the like, the synthesis conditions are mild, and the method is an efficientand convenient production process.

Description

Technical field [0001] The invention relates to the preparation of gemini amine oxides containing alkyl ester groups and ethyl groups, and belongs to the technical field of organic compound synthesis. Background technique [0002] As a kind of weak cationic amphoteric surface activity, amine oxide has the advantages of micro-oxidizing, slightly alkaline, good biodegradability, low irritation and low toxicity. It is added to many types of shampoo baths. With the improvement of people's living standards, the demand for high-end daily chemical products continues to increase. The high-efficiency compatibility of amine oxide with other anionic and cationic surfactants has become increasingly prominent, and its market has gradually expanded. [0003] Compared with ordinary surfactants, gemini amine oxides containing alkyl ester ethyl groups not only have the advantages of higher surface activity and lower critical micelle concentration, but also have good thickening, antistatic, soft, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C291/04
Inventor 不公告发明人
Owner BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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