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Method for synthesizing carvacrol by limo nene epoxides

A technology for epoxy limonene and carvacrol is applied in the chemical field, can solve problems such as limited application, environmental pollution, aluminum salt and iron salt solid waste generation, etc., and achieves the effects of convenient source, green synthesis process and low cost.

Active Publication Date: 2016-04-13
江苏宏邦化工科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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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 synthesizing carvacrol by limo nene epoxides

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Experimental program
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Effect test

Embodiment 1

[0021] Step 1: Add 300g (2mol) of epoxy limonene and 5g (0.03mol) of cuprous bromide into a 500mL three-necked flask, and then react at 160°C for 6-8 hours. After the GC shows that the reaction is over, add 30g of white oil to the reaction. After vacuum distillation, 250 g of isodihydrocarvone with a content greater than 90% was obtained, with a yield of 83%. In addition, the rectification still liquid containing the catalyst can catalyze the reaction to proceed normally again.

[0022] Step 2 Put 250g (1.67mol) of isodihydrocarvone obtained above and 20g of xylene into a 500mL three-necked flask, then add 100g (0.05mol) of catalyst B, and react under reflux at 190-220°C. During the reaction, Constantly use the pump to blow air under the surface of the reaction liquid to continuously distill the water produced by dehydrogenation. After about 4 to 5 hours, GC shows that 39% of isodihydrocarvone remains, stop the reaction, filter to remove the catalyst, and decompress the filtra...

Embodiment 2

[0025] Step 1: Add 300 g (2 mol) of epoxylimonene and 3 g (0.02 mol) of cuprous bromide into a 500 mL three-necked flask, and then react at 170 ° C for about 4 to 5 hours. After the GC shows that the reaction is over, rectify under reduced pressure to obtain a content greater than 90% isodihydrocarvone 255g, productive rate 85%.

[0026] Step 2 Put 255g (1.7mol) of isodihydrocarvone obtained above and 20g of xylene into a 500mL three-necked flask, then add 50g (0.023mol) of catalyst B, and react under reflux at 190-220°C. During the reaction, Constantly use the pump to blow air under the reaction liquid surface, about 6 to 8 hours, GC shows that 40% of isodihydrocarvone remains, stop the reaction, filter to remove the catalyst, carry out vacuum distillation on the filtrate, recover 16g of solvent and unreacted 97g of raw materials were further rectified to obtain 118g of carvacrol finished product with a content greater than 98%, and the effective yield was 75%.

Embodiment 3

[0028] Step 1: Add 300g (2mol) of epoxy limonene and 3.5g (0.01mol) of nickel trifluoromethanesulfonate into a 500mL three-necked flask, and then react at 160°C for about 2 to 3 hours. After the reaction is shown by GC, rectify under reduced pressure 240 g of isodihydrocarvone with a content greater than 90% was obtained, and the yield was 80%.

[0029] Step 2 Put 240g (1.6mol) of isodihydrocarvone obtained above and 20g xylene into a 500mL three-necked flask, then add 80g (0.038mol) of catalyst B, and react under reflux at 190-220°C. During the reaction, Continuously use the pump to blow air under the reaction liquid surface, about 6 to 7 hours, GC shows that 32% of isodihydrocarvone remains, stop the reaction, filter to remove the catalyst, and carry out vacuum distillation on the filtrate to recover 16g of solvent and unreacted 76g of raw material was further rectified to obtain 118g of carvacrol finished product with a content greater than 98%, and the effective yield was ...

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Abstract

The invention provides a method for synthesizing carvacrol by limo nene epoxides. The method comprises the following steps: step 1, under the action of a Lewis acid catalyst A, limo nene epoxide is heated up for open-loop rearrangement reaction to produce isodihydrocarvone, after reaction, white oil is added into the reaction liquid, vacuum distillation is conducted to obtain an isodihydrocarvone end product, and the catalyst A remains in the residue; step 2, isodihydrocarvone prepared in the step 1 and a catalyst B are dissolved in a solvent, the solvent is heated up for dehydrogenation oxidation to produce carvacrol, the reaction process is monitored by gas chromatography, when the content of isodihydrocarvone is 30-40%, the reaction is terminated, the catalyst B is filtered and separated out, vacuum distillation is performed on the filtrate, isodihydrocarvone and the solvent which are not subjected to reaction are reclaimed, and distillation is further conducted to obtain a carvacrol end product. The raw material is low in price and easily accessible, the synthesis process is environment-friendly, the catalysts can be recycled, and the method provided by the invention is 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 epoxy limonene. 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 ingredien...

Claims

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Application Information

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IPC IPC(8): C07C39/06C07C37/07
CPCC07C37/07C07C37/74C07C45/58C07C45/82C07C49/603C07C39/06
Inventor 刘晓涛李绍玉吴庆典万猛张建洋刘颖汤海潮
Owner 江苏宏邦化工科技有限公司
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