Green synthesis of high-content carvacrol capable of replacing natural origanum

A technology of green synthesis and carvacrol, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of harmful working environment and high toxicity of dichloroethane, and achieve high product yield and convenient operation , the effect of mild reaction conditions

Active Publication Date: 2009-07-08
HUAIAN WAN BANG SPICE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method can obtain carvacrol with higher yield, the solvent used in this method is ethylene dichloride, and ethylene dichloride is highly toxic, is a highly toxic compound, and is al...

Method used

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  • Green synthesis of high-content carvacrol capable of replacing natural origanum
  • Green synthesis of high-content carvacrol capable of replacing natural origanum
  • Green synthesis of high-content carvacrol capable of replacing natural origanum

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Put 130ml of phosphoric acid solution with a mass concentration of 45%, 100ml of L-carvone (about 96 grams) with a mass content of 99.25%, and 1.8 grams of PEG-600 into a 500ml three-necked flask, heat the oil bath to 102°C, keep the temperature for 9.5 hours, and take a sample GC analysis shows that 0.035% of L-carvone remains, the reaction is terminated by lowering the temperature, the stratification is allowed to stand, and the acid liquid phase in the lower layer is recycled; the organic phase in the upper layer is neutralized to PH=6.4 with a 5% sodium carbonate aqueous solution with a mass concentration of 5%, and the organic phase is reused Wash with saturated brine until neutral, dry over anhydrous magnesium sulfate, and distill under reduced pressure to obtain 93.4 g of carvacrol with a content of 99.85% and a yield of 98.1%.

Embodiment 2

[0019] Put 120ml of sulfuric acid solution with a mass content of 43%, 100ml of L-carvone (about 96 grams) with a mass content of 99.25%, and 1.9 grams of PEG-400 into a 500ml three-necked flask, heat the oil bath to 108°C, keep the temperature for 8 hours, and take a sample GC analysis shows that L-carvone remains at 0.027%, the reaction is terminated by cooling down, the layer is allowed to stand for stratification, and the acid liquid phase in the lower layer is recycled; the organic phase in the upper layer is neutralized to PH=6.8 with a 5% aqueous solution of sodium carbonate, and the organic phase is then saturated with Wash with salt water until neutral, dry over anhydrous magnesium sulfate, and distill under reduced pressure to obtain 93.8 g of carvacrol with a content of 99.88% and a yield of 98.5%.

Embodiment 3

[0021] Put 100ml of methanesulfonic acid solution with a mass content of 40%, 100ml of L-carvone (about 96 grams) with a mass content of 99.25%, and 1.6 grams of PEG-600 into a 500ml three-necked flask, heat the oil bath to 105°C, and heat for 8.5 Hours, sampling GC analysis, L-carvone residual 0.01%, cooling to terminate the reaction, standing for stratification, the lower layer of acid liquid phase circulation; the upper organic phase with a mass concentration of 5% sodium carbonate aqueous solution to neutralize to PH = 7.0, organic The phase was washed with saturated brine until neutral, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to obtain 94.1 g of carvacrol with a content of 99.86% and a yield of 98.7%.

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Abstract

The invention discloses a green synthesis method for high-content carvacrol capable of replacing natural oregano. The method comprises the steps of taking food-grade L-carvone as raw material, adopting organic acid or inorganic acid as a main catalyst, taking PEG-400 or PEG-600 as an auxiliary catalyst and preparing the high-content carvacrol through intramolecular rearrangement reaction. The method adopts one step to synthesize a target product, and has the advantages of mild reaction conditions and convenient operation. The product is high in yield and good in quality, and can replace natural carvacrol. As no solvent harmful to human body and environment is added in reaction, the method is safe and friendly to environment.

Description

technical field [0001] The invention relates to a synthesis method of a compound, in particular to a green synthesis method of high-content carvacrol that can replace natural oregano. Background technique [0002] Carvacrol is an important product used in spices, food additives, feed additives, antioxidants, sanitary bactericides, insect repellents, preservatives, deodorants, pharmaceutical intermediates and other industries. It is used in liquid crystal and magnetic materials as Preservatives, etc., the market prospect is broad. [0003] Natural oregano oil is rich in 60% carvacrol, which is the main functional substance of oregano oil, so carvacrol is also called oregano oil. Oregano is a plant of the genus Origanum of the Lamiaceae, also known as Zhishencao, Nepeta and other local symbols. The volatile oil extracted from it is the most pure traditional Chinese medicine additive with broad-spectrum antibacterial properties against 31 common enteritis-causing bacteria and...

Claims

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Application Information

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IPC IPC(8): C07C39/06C07C37/055
Inventor 林祥陈文昌陈兆刚许竹青
Owner HUAIAN WAN BANG SPICE IND CO LTD
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