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Synthetic method of eugenol

A synthesis method and eugenol technology are applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., and can solve problems such as increased production cost, pollution, and difficulty in wastewater treatment, and achieve increased yield, reduced production cost, and reaction mild conditions

Pending Publication Date: 2020-07-28
江西恒诚天然香料油有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, the yield of eugenol is only about 30%, and the use of copper salt makes wastewater treatment very difficult, causing relatively large pollution; the method disclosed in patent WO2015 / 15445 improves the above method, adding a dosage of more Sodium iodide and other compounds
After the improvement, the productive rate of eugenol has been increased to about 50%, but the production cost has been greatly increased, and there are still about 10% ortho isomer by-products in the eugenol product obtained after high vacuum distillation

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 1. Add 12.40 grams (0.10mol) of guaiacol, 20.25 grams (0.15mol) of sulfuryl chloride and 60ml of toluene into a 200ml round bottom flask, stir and react at 20°C, and absorb the tail gas with sodium hydroxide solution; after 6 hours of reaction Stop heating, add saturated sodium bicarbonate solution to the reaction mixture to neutralize to pH = 6-7, separate the toluene layer, dry over anhydrous sodium sulfate, filter, and distill toluene under reduced pressure to obtain 4-chloro-2-methoxy 14.27 g (0.09 mol) of base phenol, yield 90%.

[0036] 2. Add 15.86 grams (0.10mol) of 4-chloro-2-methoxyphenol, 15.18 grams (0.15mol) of triethylamine and 80ml methylene chloride in a 200ml round bottom flask, and add 12.08 grams of methyl chloromethyl ether dropwise. gram (0.15 mol). After the dropwise addition was completed, the reaction was stirred at room temperature for 12 hours, then 100ml of water was added to the reaction mixture, the dichloromethane layer was separated, the ...

Embodiment 2

[0041] 1. Add 12.40 g (0.10 mol) of guaiacol, 0.16 mol of thionyl chloride and 70 ml of dichloromethane into a 200 ml round bottom flask, stir and react at 25°C, and absorb the tail gas with sodium hydroxide solution. Stop heating after reacting for 7 hours, add saturated sodium bicarbonate solution to the reaction mixture to neutralize to pH = 6-7, separate the dichloromethane layer, dry over anhydrous sodium sulfate, filter, and distill off the dichloromethane under reduced pressure to obtain 14.43 g (0.091 mol) of 4-chloro-2-methoxyphenol, yield 91%.

[0042] 2. Add 15.86 g (0.10 mol) of 4-chloro-2-methoxyphenol, 0.16 mol of ethyl diisopropylamine and 80 ml of dichloroethane in a 200 ml round bottom flask, add ethyl-2-chloro Ethyl ether 0.16mol. After the dropwise addition was completed, the reaction was stirred at room temperature for 13 hours, then 120ml of water was added to the reaction mixture, the dichloroethane layer was separated, the water layer was extracted once...

Embodiment 3

[0047] 1. Add 12.40 g (0.10 mol) of guaiacol, 0.18 mol of thionyl chloride and 80 ml of dichloroethane into a 200 ml round bottom flask, stir and react at 22 ° C, and absorb the tail gas with sodium hydroxide solution. Stop heating after reacting for 6.5 hours, add saturated sodium bicarbonate solution to the reaction mixture to neutralize to pH = 6-7, separate the dichloroethane layer, dry over anhydrous sodium sulfate, filter, and distill off dichloroethane under reduced pressure Afterwards, 14.59 g of 4-chloro-2-methoxyphenol was obtained with a yield of 92%.

[0048] 2. Add 15.86 g (0.10 mol) of 4-chloro-2-methoxyphenol, 0.14 mol of potassium carbonate and 75 ml of toluene into a 200 ml round bottom flask, and add 0.14 mol of methyl bromomethyl ether dropwise. After the dropwise addition was completed, the reaction was stirred at room temperature for 11.5 hours, then 95ml of water was added to the reaction mixture, the toluene layer was separated, the water layer was extra...

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Abstract

A synthetic method of eugenol comprises the following steps of: dropwise adding a halogenating reagent into guaiacol, adding an alkaline saturated solution for layering, washing with water, drying, filtering, and carrying out reduced pressure distillation to obtain 4-halogen-2-methoxyphenol; adding 4-halogen-2-methoxyphenol and alkali into an organic solvent, adding alkyl halide alkyl ether, adding water, layering, extracting the water layer with a solvent, drying the organic layer, filtering, and removing the solvent to obtain 4-halogen-2-methoxy-1-alkoxy alkylphenol; dropwise adding 4-halogen-2-methoxy-1-alkoxy alkylphenol into an ether solution of allyl magnesium halide; adding an ammonium chloride aqueous solution to obtain a mixture, carrying out reduced pressure distillation to remove ether, carrying out water layer extraction, combining ethyl acetate layers, drying, filtering, and carrying out reduced pressure distillation to obtain 4-allyl-2-methoxy-1-alkoxy alkylphenol; and mixing the product with p-toluenesulfonic acid monohydrate, stirring, carrying out reduced pressure distillation, and carrying out high vacuum distillation to obtain eugenol. The defects that in the prior art, guaiacol directly reacts with 3-chloropropene, so that ortho-position reaction is easier, and the para-position product yield is low and does not exceed 50% are overcome.

Description

technical field [0001] The invention relates to the technical field of synthesis of eugenol, and specifically designs a synthesis method of eugenol. Background technique [0002] Eugenol, also known as 4-allyl guaiacol, is a colorless or pale yellow liquid with a strong clove aroma and is insoluble in water. It is mainly used for antibacterial and blood pressure lowering. It can also be used in perfume flavors, various cosmetic flavors and soap flavor formulas, and can also be used in the deployment of food flavors. The structural formula is as follows: [0003] [0004] Natural eugenol is mainly obtained by extracting and distilling the dried buds of cloves, a plant of the family Myrtaceae. The chemical synthesis of eugenol basically takes guaiacol as a raw material for reaction. The Claisen rearrangement reaction is a common method for synthesizing eugenol from guaiacol, and its chemical equation is as follows: [0005] [0006] Because the ortho position is easi...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/26
CPCC07C41/26C07C41/48C07C41/22C07C43/23C07C43/315
Inventor 傅深敬傅敏
Owner 江西恒诚天然香料油有限公司
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