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1,2-trans alcohol ether xyloside surfactant and preparation method

A technology of xyloside and alcohol ether, which is applied in the field of fine chemical surfactants and can solve the problems of poor water solubility of alkyl glycosides

Inactive Publication Date: 2019-06-28
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to improve the inherent defects of the above-mentioned APG and alkyl glycosides obtained by separation, purification or synthesis, such as poor water solubility and easy precipitation at low temperature, as well as the vision of making full use of xylose obtained from the conversion of leftovers of agricultural products, and provides A class of novel alcohol ether xyloside nonionic surfactants with improved hydrophilicity and water solubility 1,2-trans alkyl oligooxyethyl-β-D-xylopyranoside and preparation method thereof

Method used

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  • 1,2-trans alcohol ether xyloside surfactant and preparation method
  • 1,2-trans alcohol ether xyloside surfactant and preparation method
  • 1,2-trans alcohol ether xyloside surfactant and preparation method

Examples

Experimental program
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Effect test

preparation example

[0023] Add 0.33mol of dried D-xylose, 1.67mol of acetic anhydride and 83.26mmol of anhydrous sodium acetate into a 500mL three-necked flask, heat up to dissolve the solid slightly, then stop heating and continue stirring until the solid is completely dissolved. The reaction solution was clear and cooled to room temperature. Add 83.26mmol anhydrous sodium acetate again, heat to 110 ℃ reflux reaction again, TLC (developing agent: V 石油醚 :V 乙酸乙酯 = 1:1) Monitor the reaction to the end point. When it was slightly cold, the reaction solution was poured into ice water and stirred while it was hot, and a large amount of solids were precipitated immediately, filtered with suction, and the filter cake was washed several times with water, and dried to obtain 78.60 g of acetyl-protected D-xylose, with a yield of 74.8%. The compound was washed with aqueous methanol (V 甲醇 :V 水 =1:2) After recrystallization and purification, it was directly used in the reactions in subsequent examples.

Embodiment 1

[0025] Embodiment 1: Octyldipolyoxyethyl-β-D-xylopyranoside (C 8 (OE) 2 X)

[0026] (1) In the round-bottomed flask, add successively prepared 22.42mmol of acetyl-protected D-xylose, Molecular sieve-dried 50mL dichloromethane and 33.63mmol diethylene glycol monooctyl ether were stirred and dissolved, cooled to 0°C, 67.27mmol boron trifluoride diethyl ether was added dropwise, the temperature was naturally raised to room temperature and stirred for reaction, TLC (developing agent: V 石油醚 :V 乙酸乙酯 =2:1) ​​Monitor the progress of the reaction, and the reaction is completed in 3h. 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 subjected to column chromatography (V 石油醚 :V 乙酸乙酯 =5:1) separation to obtain 7.06 g of triacetyloctyldipolyoxyethyl-β-D-xylopyranoside, with a yield of 66.1%.

[0027] (2) Add 14.82mmol of triac...

Embodiment 2

[0030] Embodiment 2: nonyldipolyoxyethyl-β-D-xylopyranoside (C 9 (OE) 2 X)

[0031] The method is similar to Example 1. (1) The dosage is specifically: 22.29mmol acetyl-protected D-xylose, Molecular sieve-dried 50mL dichloromethane, 33.44mmol diethylene glycol monononyl ether, 66.87mmol boron trifluoride ether; 3h to complete the reaction; through similar post-treatment, the ratio of the eluent separated by column chromatography for V 石油醚 :V 乙酸乙酯 =5:1, 7.41 g of triacetylnonyldipolyoxyethyl-β-D-xylopyranoside was obtained with a yield of 67.8%. (2) The dosage is specifically: 15.11 mmol of triacetylnonyldipolyoxyethyl-β-D-xylopyranoside, 40 mL of anhydrous methanol, and the reaction is completed in 2 hours. Through similar post-treatment, 4.81 g of nonyldipolyoxyethyl-β-D-xylopyranoside was obtained with a yield of 87.3%.

[0032] nonyldipolyoxyethyl-β-D-xylopyranoside 1 H NMR, mass spectrometry test data are as follows:

[0033] 1 H NMR (D 2 O)δ4.37(d,J 1,2 =7.7H...

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Abstract

The invention discloses a sugar-based non-ionic surfactant 1,2-trans alcohol ether xyloside (Cn(OE)mX) and a preparation method thereof. The compound is novel in structure, a hydrophilic connecting arm is introduced to increase an HLB value, the hydrophilicity and the water solubility are improved, and the application range can be expanded. At the same time, renewable xylose is also utilized as araw material to prepare the xyloside compound through the method which is easy to implement and mild and controllable in condition.

Description

technical field [0001] The invention belongs to the field of fine chemical surfactants, and in particular relates to a novel sugar-based nonionic surfactant 1,2-trans alcohol ether xyloside and a preparation method. technical background [0002] Alkyl glycoside is a new type of nonionic surfactant, which is a mixture of monoglycoside, diglycoside, triglycoside and other polyglycosides. It is customary to call this mixture alkyl glycoside or alkyl polyglycoside. English It is called alkylpolyglycoside, or APG for short. As a new type of green nonionic surfactant, APG has many advantages such as good surface activity, good compatibility, non-toxicity, non-irritation, and easy biodegradation (Applied Chemical Industry, 2008, 37 (6): 683-684), It is widely used in detergents, daily cosmetics (China Cosmetics, 2012, (1): 64-68), textile printing and dyeing (printing and dyeing auxiliaries, 2006, 23 (6): 1-4), food additives, oil extraction ( Applied Chemical Industry, 2012, 41(...

Claims

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Application Information

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IPC IPC(8): C07H15/08C07H1/00B01F17/56C09K23/56
Inventor 陈朗秋伍修炳陈凯奋
Owner XIANGTAN UNIV
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