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Acetal-substituted glucosamide, preparation method and method for preparing supramolecular gel

A technology of glucosamide and supramolecular gel, which is applied in the field of gel formation, acetal-substituted glucosamide and its preparation, can solve the problems of few types of thixotropic gel factors and achieve high recovery rate

Inactive Publication Date: 2015-04-01
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The research on thixotropic organic small molecule gelling factors is a relatively new research field, and there are few types of thixotropic gelling factors discovered so far.

Method used

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  • Acetal-substituted glucosamide, preparation method and method for preparing supramolecular gel
  • Acetal-substituted glucosamide, preparation method and method for preparing supramolecular gel
  • Acetal-substituted glucosamide, preparation method and method for preparing supramolecular gel

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Experimental program
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Effect test

Embodiment 1

[0032] The raw material used in the present invention, 2,4-(3,4-dichlorobenzylidene)-D-gluconate methyl ester is prepared by the following method:

[0033]

[0034] Add 215.8g of 50wt% D-gluconic acid aqueous solution (containing 0.55mol D-gluconic acid), 100 mL of methanol, and 200 mL of concentrated hydrochloric acid to a 1L four-neck flask equipped with mechanical stirring and thermometer at room temperature, and stir. Add the methanol solution of 3,4-dichlorobenzaldehyde (87.5g (0.50mol) of 3,4-dichlorobenzaldehyde is dissolved in 300mL methanol). After 4 hours of reaction, the system begins to become viscous. Continue to stir and react for 20 hours. After the reaction is completed, add 100 mL of water to the system, stir for 2 hours, and then filter with suction. The filter cake is washed with a large amount of water to pH 6-7, and then washed twice with 200 mL of hot dichloromethane, drained to obtain product II, and dried to obtain 140 g . The yield was 76%, and the melti...

Embodiment 2

[0036] The preparation method of acetal-substituted glucamide includes the following steps:

[0037] Using 4-dimethylaminopyridine (DMAP) as a catalyst, 2,4-(3,4-dichlorobenzylidene)-D-gluconate methyl ester and aliphatic monoamine as raw materials, pyridine as a solvent (the solvent can also be selected An acetal-substituted glucamide compound was synthesized under the condition of methanol. The reaction equation is shown below. Among them: n=1-10,12,14,16,18; the corresponding compound is called B for short n .

[0038]

Embodiment 3

[0040] Acetal-substituted glucamide (B 1 ) The preparation method includes the following steps:

[0041] Add 5g (0.014mol) 2,4-(3,4-dichlorobenzylidene)-D-gluconate methyl (II) into a 250mL four-neck flask equipped with mechanical stirring and thermometer at 20-25℃, 50 mL of pyridine was used as the solvent, 0.01 g (0.008 mmol) of DMAP was used as the catalyst, and after stirring for 30 minutes, 3.3 g of a 40% (mass percentage) methylamine aqueous solution (containing 0.042 mol of methylamine) was added and stirred overnight at room temperature. After the reaction was completed, 25 mL of water was added to the system, stirred for 2 hours and filtered with suction. After the filter cake was washed with water, it was washed with methanol and drained to obtain a crude product. The crude product was refluxed in 20 mL methanol for 30 minutes, cooled to room temperature, stirred for 1 hour, and filtered with suction. The filter cake was washed with methanol and dried to obtain 3.9 g of...

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Abstract

The invention discloses acetal-substituted glucosamide, a preparation method and a method for preparing a supramolecular gel. The acetal-substituted glucosamide is as shown in formula I (as shown in Specification), wherein n is selected from 1-10, 12, 14, 16 or 18. The supramolecular gel formed from the acetal-substituted glucosamide disclosed by the invention in a solution is thixotropic, high in recovery rate and controllable. The gel factors are capable of achieving oil and water separation, dye wastewater purification and the like. The supramolecular gel can be used for preparing coatings, ink and lubricants.

Description

Technical field [0001] The invention belongs to the technical field of fine chemicals, and specifically relates to an acetal-substituted glucamide, a preparation method thereof and a method for forming a gel. Background technique [0002] The small molecule gelling factor interacts through hydrogen bonds, π-π stacking, van der Waals forces and other non-covalent bonds, and can gel solvent molecules under certain conditions. Under the stimulus of external conditions, it can reversibly change between the sol state and the gel state. In addition to thermal reversibility, some organic small molecule gels also have thixotropy: when a certain external force is applied, the gel will become liquid, and the system can return to a gel state when the external force is removed. The research on organic small molecule gel factors with thixotropy belongs to a relatively new field of research, and currently there are fewer categories of thixotropic gel factors. [0003] Van Esch et al. found tha...

Claims

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Application Information

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IPC IPC(8): C07D319/06B01J20/22B01J20/28B01J20/30C02F1/28C02F1/40B01J13/00
CPCB01J13/00B01J20/22B01J20/28B01J20/30C02F1/28C02F1/40C07D319/06B01J13/0065B01J20/28047B01J20/3085C02F1/285
Inventor 宋健管西栋冯荣秀申花花
Owner TIANJIN UNIV
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