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Method for synthesizing carvacrol with epoxy limonene foot oil

A technology of epoxy limonene and carvacrol, which is applied in the chemical industry, can solve problems such as limited application, environmental pollution, aluminum salt and iron salt solid waste, and achieve the effect of solving environmental protection problems

Active Publication Date: 2018-08-03
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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Step 1: Add 500g of epoxy limonene foot oil (60% diethylene glycol content, 300g), 300g of toluene and 15g of p-toluenesulfonic acid into a 1000 mL reactor, then react at 120-150°C for about 3-4 hours, GC After showing that the reaction is over, lower the temperature of the kettle to below 40°C and add 250g of 5wt% 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 230 g of isodihydrocarvone with a content greater than 90%, with a yield of 86%.

[0021] Step 2 Put 230g of isodihydrocarvone and 20g of xylene obtained above into a 500 mL three-neck flask, then add 180g of catalyst B, and react under reflux at 190-220°C. During the reaction, pump the reaction liquid continuously Blow air under the face, about 4-5 hours, GC shows that 40% of isodihydrocarvone remains, stop the reaction, filter to remove the catalyst, carry out vacuum distillation on the filtrate, recover 14g o...

Embodiment 2

[0024] Step 1: Add 500g of epoxy limonene foot oil (60% diethylene glycol content), 300g of toluene and 10g of p-toluenesulfonic acid into a 1000 mL reactor, then react at 120-150°C for about 4-5 hours, GC shows that the reaction After the end, reduce the kettle temperature to below 40°C, add 200g 5wt% 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 225 g of isodihydrocarvone with a content greater than 90%, with a yield of 84%.

[0025] Step 2 Put 225g of isodihydrocarvone and 20g of xylene obtained above into a 500 mL three-necked flask, then add 115g of catalyst B, and react under reflux at 190-220°C. During the reaction, pump continuously to the reaction solution Blow air under the face, about 5-6 hours, GC shows that 38% of isodihydrocarvone remains, stop the reaction, filter to remove the catalyst, carry out vacuum distillation on the filtrate, recover 15g of solvent a...

Embodiment 3

[0027] Step 1: Add 500g of epoxy limonene foot oil (60% diethylene glycol content), 300g of toluene and 5g of p-toluenesulfonic acid into a 1000 mL reactor, then react at 120-150°C for 6-7 hours, GC shows that the reaction is complete After that, the temperature of the kettle was lowered to below 40°C, and 170g of 5wt% NaHCO was added 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 213 g of isodihydrocarvone with a content greater than 90%, with a yield of 80%.

[0028] Step 2 Put 213g of isodihydrocarvone and 20g of xylene obtained above into a 500 mL three-necked flask, then add 50g of catalyst B, and react under reflux at 190-220°C. During the reaction, pump continuously to the reaction solution Blow air under the face, about 9 to 10 hours, GC shows that 33% of isodihydrocarvone remains, stop the reaction, remove the catalyst by filtration, carry out vacuum distillation on the ...

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PUM

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Abstract

The invention discloses a method for synthesizing carvacrol with limonene epoxide foot oil. The method includes the following steps that 1, the limonene epoxide foot oil and a catalyst A are dissolved in solvent, menthene diol in the limonene epoxide foot oil is dehydrated and subjected to a ring opening rearrangement reaction through heating to generate dihydrocarvone, the dihydrocarvone is neutralized to reach the pH value of 7-8 through an alkaline solution after the reaction is ended, and then through standing layering and organic phase vacuum distillation, a dihydrocarvone finished product is obtained; 2, the prepared dihydrocarvone in the step1 and a catalyst B are dissolved in solved and heated for a dehydrogenation oxidation reaction to generate carvacrol, the catalyst B is subjected to filtering separation, filtrate is subjected to vacuum distillation, and then the carvacrol finished product is obtained, wherein the catalyst A is organic or inorganic acid, and the catalyst B is a carbon-based composite catalyst. The brand-new method for synthesizing carvacrol is provided, more importantly, the existing limonene epoxide foot oil (the effective component is menthene diol) is comprehensively utilized, and while environmental friendliness in production is achieved, new social benefits and economic benefits are created.

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 foot oil. 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/07C07C39/06
CPCC07C37/07C07C45/52C07C39/06C07C49/603
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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