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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 separation methods, chemical instruments and methods, liquid separation, etc., can solve the problem of few types of thixotropic gel factors and achieve high recovery rate

Inactive Publication Date: 2016-08-24
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] Raw material 2,4-(3,4-dichlorobenzylidene)-D-methyl gluconate used in the present invention is made by following method:

[0033]

[0034] Add 215.8g of 50wt% D-gluconic acid aqueous solution (containing 0.55mol D-gluconic acid), 100mL of methanol, and 200mL of concentrated hydrochloric acid into a 1L four-necked flask equipped with mechanical stirring and a thermometer at room temperature, and stir. Add a methanol solution of 3,4-dichlorobenzaldehyde (dissolve 87.5g (0.50mol) of 3,4-dichlorobenzaldehyde in 300mL of methanol), and the system becomes viscous after 4 hours of reaction. Continue stirring for 20 hours. After the reaction was completed, add 100mL of water to the system, stir for 2 hours and then filter with suction, wash the filter cake with a large amount of water to pH 6-7, then wash twice with 200mL of hot dichloromethane, drain to obtain product II, and dry to obtain 140g . The yield was 76%, and the melting point was 188.6-189.2°C. 1 H NMR (400MHz,...

Embodiment 2

[0036] The preparation method of the glucosamide substituted by acetal comprises the steps:

[0037] With 4-dimethylaminopyridine (DMAP) as catalyst, 2,4-(3,4-dichlorobenzylidene)-D-gluconate methyl ester and aliphatic monoamine as raw materials, pyridine as solvent (solvent can also be selected Methanol) synthesized under the conditions of acetal-substituted glucose amide compounds, the reaction equation is as follows. Among them: n=1-10, 12, 14, 16, 18; the corresponding compound is referred to as B n .

[0038]

Embodiment 3

[0040] Acetal substituted glucamide (B 1 ) preparation method, comprising the steps of:

[0041] Add 5g (0.014mol) 2,4-(3,4-dichlorobenzylidene)-D-gluconate methyl ester (II) to a 250mL four-neck flask equipped with mechanical stirring and a thermometer at 20-25°C, Pyridine 50mL was used as solvent, DMAP 0.01g (0.008mmol) was used as catalyst, after stirring for 30min, 3.3g of 40% (mass percent concentration) methylamine aqueous solution (containing 0.042mol 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, then filtered with suction, and the filter cake was washed with water, then washed with methanol and dried to obtain a crude product. The crude product was refluxed in 20 mL of methanol for 30 min, cooled to room temperature, stirred for 1 h and filtered with suction, the filter cake was washed with methanol, and dried to obtain 3.9 g of the compound N-methyl-2...

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Abstract

Disclosed are an acetal-substituted glucamide and a preparation method thereof, and a method for preparing a supramolecular gel, wherein the acetal-substituted glucamide is as shown in formula I, wherein n is one of 1-10, 12, 14, 16 or 18; and the supramolecular gel formed by the acetal-substituted glucamide of the present invention is thixotropic in a solution, has a high recovery rate and is regulatable. Such a gelator has the abilities of separating oil and water, purifying dye wastewater, etc. The supramolecular gel can be used to prepare paints, inks and lubricants.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to an acetal-substituted glucose amide, a preparation method thereof, and a gel-forming method. Background technique [0002] Small molecule gelling factor can gel solvent molecules under certain conditions through hydrogen bond, π-π stacking, van der Waals force and other non-covalent interaction. Under the stimulation 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 are also thixotropic: when a certain external force is applied, the gel will become liquid, and the system will return to the gel state when the external force is removed. The research on thixotropic small organic molecule gelling factors is a relatively new research field, and there are few types of thixotropic gelling factors discovered so far. [0003] Van Esch et al. found that the ur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D319/06B01J20/22B01J20/28B01J20/30C02F1/28C02F1/40B01J13/00
CPCB01J13/00B01J20/22B01J20/28B01J20/30C02F1/28C02F1/40C07D319/06
Inventor 宋健管西栋冯荣秀申花花
Owner TIANJIN UNIV
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