Cinnamic acetal diglycidyl ether and preparation method and application thereof

A technology of diglycidyl ether and glycidyl ether, which is applied in the field of cinnamon acetal diglycidyl ether and its preparation, can solve the problems of restricting the application of polymer materials, and achieve a low difficulty, wide application prospect, and mild reaction conditions Effect

Active Publication Date: 2018-03-13
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, there is no compound that combines cinnamaldehyde, glycidyl ether and acetal b

Method used

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  • Cinnamic acetal diglycidyl ether and preparation method and application thereof
  • Cinnamic acetal diglycidyl ether and preparation method and application thereof
  • Cinnamic acetal diglycidyl ether and preparation method and application thereof

Examples

Experimental program
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Effect test

Example Embodiment

[0031] Example 1

[0032] Such as Figure 1 to Figure 3 As shown, Embodiment 1 of the present invention includes the following steps:

[0033] (1) At room temperature, weigh 6.6g (0.05mol) of cinnamaldehyde and 23.8g (0.22mol) of trimethyl orthoformate in a dry and clean round bottom flask, dissolve them in 60mL of methanol, and add 30mg of p-toluenesulfonic acid , The reaction system was refluxed for 6 hours at 72°C and 800r / min;

[0034] (2) Add saturated sodium bicarbonate aqueous solution to the reaction system in batches to pH=7-8, remove p-toluenesulfonic acid, concentrate under reduced pressure, extract 3 times with 3*40mL dichloromethane, collect the organic layer, add 8g anhydrous Sodium sulfate removes water for 6 hours;

[0035] (3) Remove the anhydrous sodium sulfate by filtration, remove the solvent under reduced pressure, and separate by column chromatography. The column chromatography components are in a volume ratio, petroleum ether: ethyl acetate = 10:1, to obtain a ...

Example Embodiment

[0044] Example 2

[0045] (1) At room temperature, weigh 3.3 g of cinnamaldehyde and 9.9 g of trimethyl orthoformate in a dry and clean round bottom flask, dissolve in 30 mL of methanol, add 12 mg of p-toluenesulfonic acid, and the reaction system is at 68°C, 800r Reflux for 4 hours at / min;

[0046] (2) Add a saturated aqueous sodium bicarbonate solution to the reaction system in batches to pH=7-8, remove p-toluenesulfonic acid, concentrate under reduced pressure, and extract 3 times with 3*20 mL of dichloromethane. Collect the organic layer and add 4 g of anhydrous Sodium sulfate removes water for 4 hours;

[0047] (3) Remove the anhydrous sodium sulfate by filtration, remove the solvent under reduced pressure, and separate by column chromatography. The column chromatography components are in a volume ratio, petroleum ether: ethyl acetate = 10:1, to obtain a light yellow liquid cinnamon acetal 3.87 g, the yield is 87%;

[0048] (4) Dissolve 3.87g of cinnamon acetal and 3.48g of gl...

Example Embodiment

[0051] Example 3

[0052] (1) At room temperature, weigh 5 g of cinnamaldehyde and 25 g of trimethyl orthoformate in a dry and clean round bottom flask, dissolve in 90 mL of methanol, add 45 mg of p-toluenesulfonic acid, and the reaction system is at 80°C, 800 r / min Reflux for 8 hours;

[0053] (2) Add a saturated aqueous sodium bicarbonate solution to the reaction system in batches to pH=7-8, remove p-toluenesulfonic acid, concentrate under reduced pressure, extract 3 times with 3*30mL dichloromethane, collect the organic layer, add 10g anhydrous Sodium sulfate removes water for 6 hours;

[0054] (3) Remove the anhydrous sodium sulfate by filtration, remove the solvent under reduced pressure, and separate by column chromatography. The column chromatography components are in a volume ratio, petroleum ether: ethyl acetate = 10:1, to obtain a light yellow liquid cinnamon acetal 5.2 g, the yield is 77%;

[0055] (4) Dissolve 5.2 g of cinnamon acetal and 6.24 g of hydroxyethyl acrylate ...

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Abstract

The invention discloses cinnamic acetal diglycidyl ether and a preparation method and application thereof. The preparation method includes: using cinnamaldehyde, trimethyl orthoformate and glycidyl ether as the main raw materials and p-toluenesulfonic acid as the catalyst to perform substitution and etherfication reaction to obtain the target cinnamic acetal diglycidyl ether. The cinnamic acetal diglycidyl ether can be used as the acid-sensitive polyether polyol polymerization monomer. The preparation method has the advantages that the raw materials and reagents used by the method are simple and easy to obtain, the method is mild in reaction condition and low in operation difficulty, and the prepared cinnamic acetal diglycidyl ether is promising in application prospect in fields of organicchemistry and macromolecular drug carriers.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and specifically refers to a cinnamon acetal diglycidyl ether and a preparation method and application thereof. Background technique [0002] Glycidyl ether is mainly used in the production of polyether polyols, propylene glycol and various nonionic surfactants, among which polyether polyols are important raw materials for the production of polyurethane foams, insulation materials, elastomers, adhesives and coatings, etc. Ionic surfactants are widely used in petroleum, chemical, pesticide, textile, daily chemical and other industries. [0003] Cinnamaldehyde, commonly known as cinnamaldehyde, is naturally present in essential oils such as Sri Lankan cinnamon oil, cinnamon oil, patchouli oil, hyacinth oil, and rose oil. It is a synthetic spice for food that is allowed to be used in GB2076-2011 and can be used to prepare meat , condiments, oral care products, chewing gum, flavors for candies. In ...

Claims

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Application Information

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IPC IPC(8): C07D303/30C07D301/00C08G65/02
CPCC07D301/00C07D303/30C08G65/02
Inventor 李钟玉王禄胜卢成洁黄少铭吴丽滨
Owner WENZHOU UNIVERSITY
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