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Method for preparing high-purity eugenol epoxy, product and application of product

A technology of eugenol epoxy and eugenol, which is applied in the field of preparation of high-purity eugenol epoxy, can solve the problems that eugenol epoxy affects processing and utilization, and impurity is difficult to purify, etc., so as to improve compatibility, improve purity, and improve Effects of Modification Effects

Active Publication Date: 2017-12-08
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The purity of the product obtained by the two-step method is higher, but due to the problem of the purification process, the product still contains some impurities that are difficult to purify, and the purity of eugenol epoxy will directly affect the subsequent further processing and utilization

Method used

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  • Method for preparing high-purity eugenol epoxy, product and application of product
  • Method for preparing high-purity eugenol epoxy, product and application of product
  • Method for preparing high-purity eugenol epoxy, product and application of product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 350 g of epichlorohydrin and 100 g of eugenol were mixed to obtain a mixed solution, and 3.5 g of benzyltriethylammonium chloride was added to the mixed solution, and the temperature was raised to 110° C. for 2 hours to react. Then, 135 g of 20% aqueous sodium hydroxide solution was added dropwise within 5 hours, and the reaction was continued at 110° C. for 5 hours to obtain a crude product. After washing the crude product three times with water, the excess epichlorohydrin was removed by vacuum distillation to obtain the crude product, and then the crude product was mixed with methanol, cooled to -5°C and filtered to obtain eugenol epoxy, which was tested by NMR. The purity was 98%, and the yield was 82%.

Embodiment 2

[0042] The preparation process is the same as in Example 1, the only difference being that two low-temperature recrystallization processes are adopted, and the same process conditions are used twice. After nuclear magnetic testing, the purity of the eugenol epoxy prepared in this embodiment is more than 99%. The rate is 78%.

Embodiment 3

[0044] The preparation process is the same as that of Example 2, the only difference being that the process parameters of the second low-temperature recrystallization process are different from the first one, and the temperature is -20°C. Tested by nuclear magnetic resonance, the prepared eugenol epoxy has a purity of 99% and a yield of 85%.

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Abstract

The invention discloses a method for preparing high-purity eugenol epoxy. The method comprises the steps: mixing epoxy chloropropane, eugenol and benzyltriethylammonium chloride, carrying out a ring-opening reaction, then, adding a sodium hydroxide aqueous solution, and carrying out a ring-closing reaction, so as to obtain a crude product; subjecting the crude product to reduced-pressure distillation, and then, carrying out low-temperature recrystallization, thereby obtaining the eugenol epoxy, wherein the low-temperature recrystallization specifically comprises the steps of mixing liquid, obtained through reduced-pressure distillation, with an organic solvent, cooling the temperature of the mixture to -20 DEG C to -0 DEG C, and carrying out filtering, thereby obtaining the purified eugenol epoxy. According to the method for preparing the high-purity eugenol epoxy, provided by the invention, the crude product is subjected to a specific purification process, and thus, the purity of the crude product is remarkably improved to 99% or more from 90%.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method, product and application of a high-purity eugenol epoxy. Background technique [0002] Eugenol epoxy is an epoxide synthesized from bio-based raw materials. Eugenol can be extracted from lilac flower, which is a renewable biological resource. And its molecule contains allyl bonds that can be functionalized, which is beneficial to its further processing and utilization. [0003] At present, there are few eugenol epoxy synthesis methods reported in the literature, mainly including two methods: one-step method and two-step method. The one-step method is to directly add sodium hydroxide to the mixture of eugenol and epichlorohydrin, and the ring-opening reaction and ring-closing reaction are carried out simultaneously. The two-step method is to first allow eugenol and epichlorohydrin to carry out ring-opening reaction, and then add sodium hydroxide to carry ou...

Claims

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Application Information

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IPC IPC(8): C07D303/24C07D301/28C07F7/18C08K9/06
Inventor 范宏曹骏
Owner ZHEJIANG UNIV
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