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1,2-cis-glucoside surfactant and preparation method thereof

A technology of glucoside and glucopyranoside, which is applied in the field of hydrocarbyloxyethyl glucoside nonionic surfactant and its synthesis, can solve the problems of poor water solubility and easy precipitation of alkyl glucoside, and achieves reduction of solution surface tension, Renewable raw materials and enhanced hydrophilicity

Inactive Publication Date: 2018-08-17
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to improve the inherent defects of the above-mentioned alkyl polyglycosides and isolated or synthesized alkyl glycosides, such as poor water solubility and easy precipitation at low temperature, and provide a class of alkoxylated polyglycosides that improve their hydrophilicity and water solubility. Ethyl-α-D-glucopyranoside and its synthetic method

Method used

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  • 1,2-cis-glucoside surfactant and preparation method thereof
  • 1,2-cis-glucoside surfactant and preparation method thereof
  • 1,2-cis-glucoside surfactant and preparation method thereof

Examples

Experimental program
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Effect test

preparation example

[0028] Add 111.12mmol anhydrous glucose and 944.52mmol acetic anhydride to a 500mL three-neck round bottom flask, heat to 85°C-90°C with stirring, add 50.00mmol anhydrous sodium acetate in batches, heat up to 100°C-110°C, keep warm Reflux reaction, until TLC (V 石油醚 :V 乙酸乙酯 =2:1) ​​The detection reaction is complete. The reaction solution was quickly poured into 600 mL of ice water while it was hot, stirred at room temperature for 12 h, then suction filtered, washed 5 times with 1000 mL of water, and dried. With methanol and water (V 甲醇 :V 水 =1:2.5) mixed solvent for recrystallization to obtain pentaacetylglucose as a white solid with a yield of 86.8%. This product was used directly in reactions in subsequent examples.

Embodiment 1

[0030] Example 1: Hexyloxyethyl-α-D-glucopyranoside

[0031] (1) In a 100mL round bottom flask, add 12.81mmol of pentaacetylglucose and 45mL of Molecular sieve-dried dichloromethane, stirred and dissolved at room temperature, added 12.81 mmol of ethylene glycol monohexyl ether, and added dropwise 57.65 mmol of BF under stirring 3 ·Et 2 O, be warming up to 45 ℃, insulation reaction 16 hours, TLC (V 石油醚 :V 乙酸乙酯 =1.5:1) The detection reaction is complete. The mixed solution was washed successively with saturated aqueous sodium bicarbonate solution and saturated saline solution, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated, and column chromatography (V 石油醚 :V 乙酸乙酯 =3.5:1) separation to obtain hexyloxyethyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside with a yield of 45.3%. used directly in the next reaction.

[0032] (2) Add 11.50 mmol of hexyloxyethyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside and 45 mL of anhydrous methanol to a 100 mL round...

Embodiment 2

[0035] Example 2: Synthesis of Heptyloxyethyl-α-D-Glucopyranoside

[0036] (1) In a 250mL round bottom flask, add 25.62mmol of pentaacetylglucose and 85mL of Molecular sieve-dried dichloromethane, stirred and dissolved at room temperature, added 30.74 mmol of ethylene glycol monoheptyl ether, and added dropwise 115.29 mmol of BF under stirring 3 ·Et 2 O, be warming up to 48 ℃, insulation reaction 16.5 hours, TLC (V 石油醚 :V 乙酸乙酯 =2:1) ​​The detection reaction is complete. The mixed solution was washed successively with saturated aqueous sodium bicarbonate solution and saturated saline solution, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated, and column chromatography (V 石油醚 :V 乙酸乙酯 =4:1) separation to obtain hexyloxyethyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside with a yield of 44.7%. used directly in the next reaction.

[0037] (2) Add 15.00 mmol of the above-prepared heptyloxyethyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside and 55 mL of ...

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Abstract

The invention belongs to the technical field of chemistry, and particularly discloses a glycosyl nonionic surfactant 1,2-cis-hydroxyethyl glucoside and a preparation method. The structure of the glycosidic compound is as shown in formula (I). The corresponding preparation method comprises the following steps: converting glucose into pent-acetyl glucose; catalyzing the pent-acetyl glucose and glycol monohydrocarbyl ether by lewis acid (BF3.Et2O) to obtain the corresponding 1,2-cis acyl protected glucoside; and carrying out deprotection to obtain the corresponding 1,2-cis-hydroxyethyl glucoside.The alkoxyl ethyl glucoside is in series, the preparation method is simple and easy, and conditions are gentle and controllable. Because the structure is introduced with hydrophilic oxyethyl segments(-OCH2CH2-), the HLB value is increased, the hydrophilicity is improved, and the water solubility is also improved.

Description

technical field [0001] The invention relates to the technical field of alkoxyethyl glucoside nonionic surfactant and its synthesis. technical background [0002] In order to solve the dilemma of some traditional surfactants such as alkylphenol polyoxyethylene ether (APEO) (printing and dyeing auxiliaries, 2013, 30(9): 24-27) which are banned due to environmental protection reasons, the development of safe, mild, High-efficiency, environmentally friendly new surfactants and related synthesis processes have become a hot spot in contemporary surfactant research. [0003] Alkyl polyglycoside (APG) (Journal of Shaanxi University of Science and Technology, 2017, 35(1): 72-78), as a new type of green nonionic surfactant, has excellent surface activity, rich and delicate foam, and foam stabilizing performance Good, good compatibility, non-toxic, non-irritating, strong detergency, easy biodegradation, improving rumen fermentation of herbivores and many other advantages, it is widely...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/04C07H1/00B01F17/56C09K23/56
CPCC07H1/00C07H15/04C09K23/00
Inventor 陈朗秋张艳花陈凯奋
Owner XIANGTAN UNIV
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