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Method for synthetizing carvacrol through enediol

A technology of enediol and carvacrol, applied in the field of synthesis of carvacrol from ? The process is simple and the synthesis process is green and environmentally friendly

Active Publication Date: 2016-06-22
HUAIAN WAN BANG SPICE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As reported in the patent CN1488615, the method of using aluminum trichloride or ferric chloride to promote the reaction of o-cresol and 2-chloropropane to synthesize carvacrol, but this method will produce a large amount of aluminum salt and iron salt solid waste, Cause environmental pollution, which limits its further application in production

Method used

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  • Method for synthetizing carvacrol through enediol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Step 1: Add 600g of diol, 300g of toluene and 18g of p-toluenesulfonic acid into a 1000mL reactor, then react at 120-150°C for about 3-4 hours, after the GC shows that the reaction is over, lower the temperature of the kettle to below 40°C , add 300g5wt%NaHCO 3 The aqueous solution was washed to pH=7-8, and the organic phase obtained by liquid separation was rectified under reduced pressure to obtain 510 g of isodihydrocarvone with a content greater than 90%, with a yield of 85%.

[0020] Step 2 Put 510g of isodihydrocarvone and 40g of xylene obtained above into a 1000mL three-necked flask, then add 400g of catalyst B, and react under reflux at 190-220°C. During the reaction, pump continuously to the reaction liquid level Blow air for about 4 to 5 hours, GC shows that 30% of isodihydrocarvone remains, stop the reaction, remove the catalyst by filtration, carry out rectification under reduced pressure on the filtrate, recover 37g of solvent and 151g of unreacted raw mate...

Embodiment 2

[0023] Step 1: Add 600g of diol, 300g of toluene and 15g of p-toluenesulfonic acid into a 1000mL reactor, then react at 120-150°C for about 4-5 hours, after the GC shows that the reaction is over, lower the temperature of the kettle to below 40°C , add 250g5wt%NaHCO 3 The aqueous solution was washed to PH = 7-8, and the organic phase obtained by liquid separation was rectified under reduced pressure to obtain 504 g of isodihydrocarvone with a content greater than 90%, with a yield of 84%.

[0024] Step 2 Put 504g of isodihydrocarvone and 35g of xylene obtained above into a 1000mL three-necked flask, then add 300g of catalyst B, and react under reflux at 190-220°C. During the reaction, pump continuously to the reaction liquid level Blow air for about 5-6 hours, GC shows that 38% of isodihydrocarvone remains, stop the reaction, remove the catalyst by filtration, carry out rectification under reduced pressure on the filtrate, recover 30g of solvent and 190g of unreacted raw mater...

Embodiment 3

[0026] Step 1: Add 600g of diol, 300g of toluene and 7g of p-toluenesulfonic acid into a 1000mL reactor, and then react at 120-150°C for 6-7 hours. After the GC shows that the reaction is over, lower the temperature of the kettle to below 40°C. Add 200g5wt%NaHCO 3 The aqueous solution was washed to pH=7-8, and the organic phase obtained by liquid separation was rectified under reduced pressure to obtain 486 g of isodihydrocarvone with a content greater than 90%, with a yield of 81%.

[0027] Step 2 Put 486g of isodihydrocarvone and 30g of xylene obtained above into a 1000mL three-necked flask, then add 150g of catalyst B, and react under reflux at 190-220°C. During the reaction, pump continuously to the reaction liquid level Blow the air for about 9 to 10 hours, GC shows that 34% of isodihydrocarvone remains, stop the reaction, remove the catalyst by filtration, carry out vacuum distillation on the filtrate, recover 28g of solvent and 164g of unreacted raw materials, and furth...

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Abstract

The invention discloses a method for synthetizing carvacrol through enediol. The method comprises the following steps of (1) dissolving the enediol and a catalyst A into a solvent, heating to enable the enediol to produce dehydration, ring-opening and rearrangement reactions, generating iso-dihydrocarvone, after reaction, neutralizing pH to be 7 to 8 through aqueous alkali, standing for layering, and carrying out organic phase vacuum distillation to obtain an iso-dihydrocarvone finished product; (2) dissolving the iso-dihydrocarvone prepared through the step (1) and a catalyst B into a solvent, heating to produce dehydrogenation oxidation reaction, generating the carvacrol, filtering and separating the catalyst B, carrying out filter liquor vacuum distillation to obtain a carvacrol finished product. According to the method for synthetizing the carvacrol through the enediol provided by the invention, the raw materials are convenient in source, low in price and easy to obtain; the synthetic process is green and environmentally friendly; post-processing purification only depends on rectification, so that the process is simple; the catalysts can be recycled so as to be suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical industry and relates to a chemical synthesis method, in particular to a method for synthesizing carvacrol with ethylene glycol. technical background [0002] Carvacrol is a colorless to light yellow thick oily liquid with thymol smell. As a commonly used food additive and fragrance, it has the characteristics of low toxicity and naturalness, and has been approved as safe in the United States and Europe food additives. Natural carvacrol mainly exists in a variety of Labiatae plants, such as thyme and oregano. Carvacrol has a wide range of functions and application value. By destroying and changing the cell membrane structure of pathogenic bacteria, or the structure of mycelium, or effectively inhibiting the activity of conidia, it has a good growth inhibitory effect on bacteria, yeast, fungi, insects and mites, and has great Good antibacterial and insecticidal effects. It is an active ingredie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/06C07C37/07
CPCC07C37/07C07C39/06Y02P20/584C07C45/52C07C49/603
Inventor 刘晓涛李绍玉吴庆典万猛张建洋刘颖汤海潮
Owner HUAIAN WAN BANG SPICE IND CO LTD
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