Guerbet alcohol nonionic surfactant and preparation method thereof

A Guerbet alcohol, non-ionic surface technology, applied in the field of non-ionic surfactant chemistry, can solve problems such as hindering the reaction, and achieve the effects of good biodegradability, simple operation and high yield

Inactive Publication Date: 2017-12-29
湖南华腾制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most organic reagents are insoluble in water, which directly hinders the reaction

Method used

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  • Guerbet alcohol nonionic surfactant and preparation method thereof
  • Guerbet alcohol nonionic surfactant and preparation method thereof
  • Guerbet alcohol nonionic surfactant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Guerbet Cetyl Alcohol PEG500 Tetrapolyethylene Glycol Malonate

[0026] (1) Add 20 g of tetraethylene glycol into 150 ml of tetrahydrofuran, weigh 0.12 g of crushed sodium metal, add it to the above solution, and stir at room temperature for 1 h. Weigh 33g of tert-butyl acrylate and add dropwise to the above reaction solution, and stir at room temperature for 12h. TLC showed that the reaction was complete, and 20ml of water was added to quench the reaction, the solvent tetrahydrofuran was spin-off, and 150ml of water was added, followed by extraction with 200ml of dichloromethane for 3 times. The dichloromethane phase was dried with anhydrous sodium sulfate, spin-dried, and column purified to obtain about 42 g of polyethylene glycol dipropionate tert-butyl, yield: 92%. NMR data are as follows: 1HNMR (400MHz, CDCl 3 ): δ: 3.724(t, J=6.4Hz, 4H); 3.672~3.638(m, 12H); 3.530(t, J=4.8Hz, 4H); 2.893(t, J=6.8Hz, 4H); 1.460 (s, 18H).

[0027] (2) Dissolve 42 g of the product...

Embodiment 2

[0030] Guerbet Cetyl Alcohol PEG2000 Tetrapolyethylene Glycol Malonate

[0031] (1) Add 20 g of tetraethylene glycol to 150 ml of dioxane, weigh 0.15 g of crushed metal potassium, add it to the above solution, and stir at room temperature for 1 h. Weigh 33g of tert-butyl acrylate and add dropwise to the above reaction solution, and stir at room temperature for 12h. TLC showed that the reaction was complete, and 20ml of water was added to quench the reaction, the solvent dioxane was spin-off, and then 150ml of water was added, followed by extraction with 200ml of dichloromethane for 3 times. The dichloromethane phase was dried with anhydrous sodium sulfate, spin-dried, and column purified to obtain 42 g of the product, yield: 92%. NMR data are as follows: 1HNMR (400MHz, CDCl 3 ): δ: 3.733(t, J=6.4Hz, 4H); 3.652~3.622(m, 12H); 3.520(t, J=4.8Hz, 4H); 2.890(t, J=6.8Hz, 4H); 1.458 (s, 18H).

[0032](2) Dissolve 42 g of the product obtained in step (1) in 200 ml of dichlorometha...

Embodiment 3

[0035] Guerbet Cetyl Alcohol PEG2000 Tetrapolyethylene Glycol Malonate

[0036] (1) Add 20 g of tetraethylene glycol to 150 ml of dioxane, weigh 0.15 g of crushed metal potassium, add it to the above solution, and stir at room temperature for 1 h. Weigh 33g of tert-butyl acrylate and add dropwise to the above reaction solution, and stir at room temperature for 12h. TLC showed that the reaction was complete, and 20ml of water was added to quench the reaction, the solvent dioxane was spin-off, and then 150ml of water was added, followed by extraction with 200ml of dichloromethane for 3 times. The dichloromethane phase was dried with anhydrous sodium sulfate, spin-dried, and column purified to obtain 42 g of the product, yield: 92%. NMR data are as follows: 1HNMR (400MHz, CDCl 3 ): δ: 3.733(t, J=6.4Hz, 4H); 3.652~3.622(m, 12H); 3.520(t, J=4.8Hz, 4H); 2.890(t, J=6.8Hz, 4H); 1.458 (s, 18H).

[0037] (2) Dissolve 42 g of the product obtained in step (1) in 200 ml of dichlorometh...

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Abstract

The invention relates to a Guerbet alcohol nonionic surfactant and a preparation method thereof. The preparation method comprises the following steps of (1) dissolving monodisperse dihydroxy polyethylene glycol and metal alkali into a first organic solvent; dripping tert-butyl acrylate; performing reaction to obtain polyethylene glycol tert-butyl dipropionate; (2) dissolving the polyethylene glycol tert-butyl dipropionate into the first organic solvent; adding trifluoroacetic acid; performing reaction to obtain polyethylene glycol dipropionic acid; (3) dissolving the polyethylene glycol dipropionic acid into thionyl chloride for reaction; then, dissolving into a second organic solvent; under the alkali catalysis, performing single esterification reaction with Guerbet alcohol to obtain a single esterification product; (4) dissolving the single esterification product into the second organic solvent; adding PEG and alkali; performing condensation to obtain a finial product. The separation and purification are not needed; the operation is simple; the reaction temperature range is small; the reaction process controllability is high; the cost is low; the yield is high.

Description

technical field [0001] The invention belongs to the field of nonionic surfactant chemistry, and in particular relates to a Guerbet alcohol nonionic surfactant and a preparation method thereof. Background technique [0002] Most of the traditional organic reactions take place in organic solvents, and there are difficulties in the recovery of organic solvents. This not only increases the cost, but also brings serious environmental pollution problems. Especially for the synthesis of some drugs, a small amount of solvent residue will reduce the activity of the drug and even cause physiological toxicity. The concept of green chemistry proposed by the American Chemical Society encourages scholars to explore greener chemical solvents. Water has a bright future as a solvent with abundant reserves, green and low cost. However, most organic reagents are insoluble in water, which directly hinders the reaction. In view of the above problems, by adding surface active substances, the r...

Claims

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Application Information

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IPC IPC(8): C07C69/708C08G65/332C07C67/14B01F17/44C09K23/44
CPCC07C69/708C08G65/3322C09K23/00
Inventor 邓泽平成佳李虎张安林
Owner 湖南华腾制药有限公司
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