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Method for directly preparing N,N-bislactose-1,10-decamethylene diamine by adopting one-pot reaction

A decanediamine, lactose-based technology, applied in the field of sugar-based surfactant synthesis, can solve the problems of difficult control of reaction conditions, complex reaction, harsh conditions, etc., and achieves high implementation value, simple post-processing, simple and mild reaction conditions. Effect

Inactive Publication Date: 2013-03-27
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction of sugar and diamine mentioned in the literature has: Tomokazu Yoshimura, reported in 2005 to use ethylenediamine and lactobionic acid to obtain gemini surfactant through multi-step reaction, the reaction is complicated, the conditions are harsh, and the yield is low; MatthewL.Fielden, In 2001, the reaction of glucose and hexamethylenediamine was used to obtain gemini sugar-based surfactants. The reaction conditions are not easy to control, and expensive catalysts are required.

Method used

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  • Method for directly preparing N,N-bislactose-1,10-decamethylene diamine by adopting one-pot reaction
  • Method for directly preparing N,N-bislactose-1,10-decamethylene diamine by adopting one-pot reaction
  • Method for directly preparing N,N-bislactose-1,10-decamethylene diamine by adopting one-pot reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] This example is the synthesis of N,N'-dilactosyl-1,10-decanediamine. In a 250mL three-necked flask equipped with a condenser, add 10.269g (30mmol) of lactose, 2.585g (15mmol) of decanediamine, and 51g of an alcohol-water mixed solvent with a volume ratio of methanol:water of 50:100. Stir mechanically at room temperature for 20 hours, then heat in a water bath to 45°C for 2 hours, cool and place for 0.5 hours, a large amount of solid precipitates, filter with suction, wash with ether, acetone, and ethanol in sequence to obtain a light yellow solid. Then recrystallized with absolute ethanol at 60° C., recrystallized three times, and freeze-dried to obtain a white solid with a mass of 7.389 g (9 mmol) and a yield of 60%. of the resulting product 1 H-NMR (DMSO): δ1.35 corresponds to the 16 protons on the 8 methylene (16H) in the long chain of the alkyl group, and δ1.45 corresponds to the 2 methylenes connected to the secondary amino group in the long chain of the alkyl gro...

Embodiment 2

[0015] This example is the synthesis of N,N'-dilactosyl-1,10-decanediamine. In a 500mL three-neck flask equipped with a condenser, add 56.480g (165mmol) of lactose, 12.924g (75mmol) of decanediamine, and 347g of an alcohol-water mixed solvent with a volume ratio of isopropanol:water of 67:100. Stir mechanically at room temperature for 22 hours, then heat in a water bath to 50°C for 2 hours, cool and place for 2 hours, a large amount of solid precipitates, filter with suction, wash with ether, acetone, and ethanol in sequence to obtain a light yellow solid. Then recrystallized with absolute ethanol at 60° C., recrystallized three times, and freeze-dried to obtain a white solid with a mass of 44.334 g (54 mmol) and a yield of 72%. Product structure characterization results are the same as in Example 1.

Embodiment 3

[0017] This example is the synthesis of N,N'-dilactosyl-1,10-decanediamine. In a 500mL three-necked flask equipped with a condenser, add 35.428g (103.5mmol) of lactose, 7.754g (45mmol) of decanediamine, and 259g of an alcohol-water mixed solvent with a volume ratio of ethanol:water of 75:100. Stir mechanically at room temperature for 24 hours, then heat in a water bath to 55°C for 1 hour, cool and place for 1 hour, a large amount of solid precipitates, filter with suction, wash with ether, acetone, and ethanol in sequence to obtain a light yellow solid. Then recrystallized with absolute ethanol at 60°C, recrystallized three times, and freeze-dried to obtain a white solid with a mass of 27.709 g (33.75 mmol) and a yield of 75%. Product structure characterization results are the same as in Example 1.

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Abstract

The invention discloses a method for directly preparing N,N-bislactose-1,10-decamethylene diamine by adopting one-pot reaction, belonging to the technical field of synthesis of glycosyl surfactants. The method comprises the steps of: mixing lactose with decamethylene diamine in a molar ratio of (2.0-2.5):1, adding an alcohol and water mixed solvent with a volume ratio of alcohol to water being (50-75):100, wherein the ratio of the total mass of the lactose and the decamethylene diamine to the mass of the mixed solvent is 1:(4-6); and mechanically stirring for 20-24h at a normal temperature, heating to 45-60 DEG C in a water bath, reacting for 1-2h, cooling and placing for 0.5-2h, separating out a large quantity of solids, filtering, washing, re-crystallizing with absolute ethyl alcohol, freezing and drying to obtain a white solid, i.e. N,N-bislactose-1,10-decamethylene diamine. The method has the advantages of low price and easy obtaining of raw materials, simple and mild reaction conditions, convenience and safety in operation, simpleness in post-treatment, high production yield, suitability for industrial production, and high implementation value.

Description

technical field [0001] The invention relates to a method for preparing N,N'-dilactosyl-1,10-decanediamine, in particular to a one-pot method for directly preparing N,N'-dilactose with lactose and decanediamine as raw materials A method for base-1,10-decanediamine belongs to the technical field of synthesis of sugar-based surfactants. Background technique [0002] Sugar plays an important role in the interaction between cells. If the hydrophilic group of the surfactant is a sugar group, it can eliminate the toxicity of the surfactant at the molecular level and improve the water solubility of the surfactant. Therefore, the sugar-based surface Active agents can be used as components of biomaterials and drug delivery systems. N,N'-Dilactosyl-1,10-decanediamine is a gemini sugar-based surfactant, and the gemini sugar group is used as a hydrophilic group. It is green, non-toxic, and has good biocompatibility. It is a burden on the environment and the human body. Low, is an envir...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/12C07H1/00B01F17/16B01F17/38C09K23/16C09K23/38
Inventor 顾文秀王玉如毛小庆李磊吴婷婷邹路易王海军
Owner JIANGNAN UNIV
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