N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof

A technology based on alkyl ammonium bromide and sugar amide group, which is applied in the field of sugar-based amide quaternary ammonium salt surfactant and its synthesis to achieve balanced reaction, good compatibility and mild performance

Inactive Publication Date: 2013-01-16
CHINA RES INST OF DAILY CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Use gluconolactone or lactobionic acid to react with N,N-dimethyl-1,3-propanediamine, and then react with brominated alkyl to gen

Method used

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  • N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof
  • N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof
  • N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1. Synthesis of N,N-dimethyl-N'-glucosyl-1,3-propanediamine

[0035] In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 21.4 g (120 mmol) gluconolactone ), methanol 80 mL. Under the condition of stirring, the temperature was kept at 55 °C, and the reaction was carried out for 8 h. Remove from heat and let cool. The solvent was distilled off with a rotary evaporator, and the resulting product was washed twice with ether to remove residual N,N-dimethyl-1,3-propanediamine to obtain a white powder solid (N,N-dimethyl-N '-glucosyl-1,3-propanediamine) 32.2 g, yield 95.8%.

[0036] IR(KBr): 3368 cm -1 ( ν (O–H)), 2941-2819 cm -1 ( ν (C–H) in –CH 2 – or -CH 3 ), ( 1651 cm -1 ( ν (C=O) in amide), 1542 cm -1 (δ(N–H) in amide), 1461 cm -1 ( ν (C–H) in –CH 2 – ), 1091-1036 cm -1 ( ν (O–H)), 718 cm -1 (δ(C-C) in >4CH 2 ).

[0037] 1 H-NMR (CDCl 3 , ppm) δ: ...

Embodiment 2

[0042] Synthesis of N,N-Dimethyl-N'-glucosyl-1,3-propanediamine

[0043] In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 20.5 g (115 mmol) gluconolactone ), methanol 80 mL. Under the condition of stirring, the temperature was kept at 60 °C, and the reaction was carried out for 7 h. Remove from heat and let cool. Evaporate the solvent with a rotary evaporator, wash the resulting product twice with ether to remove residual N,N-dimethyl-1,3-propanediamine, and obtain a white powder solid (N,N-dimethyl-N '-glucosyl-1,3-propanediamine) 30.2g, yield 92.4%.

[0044] Synthesis of N,N-Dimethyl-N[3-(glucosamido)]propyl-N-decylammonium bromide

[0045] In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 15 g (53.6 mmol) of N,N-dimethyl-N′-glucosyl-1,3-propanediamine, bromodecyl Alkane 13 g (59 mmol), absolute ethanol 80 mL. Under t...

Embodiment 3

[0048] Synthesis of N,N-Dimethyl-N'-glucosyl-1,3-propanediamine

[0049] In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 19.6 g (110 mmol) gluconolactone ), methanol 80 mL. Under the condition of stirring, keep the temperature at 65 ℃, and react for 6 h. Remove from heat and let cool. Evaporate the solvent with a rotary evaporator, wash the resulting product twice with ether to remove residual N,N-dimethyl-1,3-propanediamine, and obtain a white powder solid (N,N-dimethyl-N '-glucosyl-1,3-propanediamine) 30 g, yield 94.3%.

[0050] Synthesis of N,N-Dimethyl-N[3-(glucosamido)]propyl-N-dodecylammonium bromide

[0051] In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 15 g (53.6 mmol) of N,N-dimethyl-N′-glucosyl-1,3-propanediamine, decabromide Dioxane 15.9 g (64 mmol), 95% ethanol 80 mL. Under the condition of stirring, th...

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Abstract

The invention relates to N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide of which the general formula of structure is as follows: wherein the R is a long chain alkyl of the C8-C14; and the glycosyl is a single-glycosyl or a dual-glycosyl. The synthetic method provided by the invention has the advantages that the synthetic process is simple, the requirement to equipment is low, the method is suitable for industrialization, the required reaction temperature is low, pressure and catalyst are not required, the reaction positions on the glycosyl are certain, the reaction is balanced, the amount of generated substitution products is not large, and the productivity is high.

Description

Technical field [0001] The present invention involves a kind of glycamide duplex ammonium salt surfactant and its synthesis method. Specifically, it involves a n, n-di methyl -N [3- (glucanamide)] propylene-N-alkylCromine and its synthesis method. Background technique [0002] In recent years, with the increasing attention of people's environmental problems, preparing environmentally friendly surfactants has also attracted more and more attention.The use of carbohydrates to produce surface active agents is not only low in raw materials and rich resources, but also for mild, non -toxic, excellent performance, and good environmental compatibility. It is one of the hotspots that people pay attention to in the 21st century.Glucose and lactose acid are prepared from starch of renewable resource starch. It has the advantages of cheap, green environmental protection, easy to react with alkylide, and the reaction does not require cumbersome, expensive hydroxyl group on the hydroxyl group...

Claims

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Application Information

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IPC IPC(8): C07C235/10C07C231/12C07H15/04C07H1/00B01F17/18B01F17/22B01F17/38B01F17/56C09K23/18C09K23/22C09K23/38C09K23/56
Inventor 智丽飞李秋小李运玲
Owner CHINA RES INST OF DAILY CHEM IND
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