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Method for preparing carvacrol by recycling carvone synthesis by-product

A technology for carvacrol and carvone is applied in the field of recovering by-products from synthesizing carvone to prepare carvacrol, which can solve problems such as waste, environmental protection, and difficulty in separation, and achieves convenient operation, mild conditions and high quality. Good results

Active Publication Date: 2009-07-08
江苏宏邦化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the production of carvone, carvone oxime undergoes a hydrolysis reaction under acidic conditions to obtain carvone products, and carvone partially undergoes intramolecular rearrangement reactions under acidic conditions, and is further converted into carvacrol, accounting for about 10% of carvone. 5% of the amount of avone, and the boiling point of carvrol and carvone is only 7.5 ° C, the separation is difficult, so in the production of carvone, there are many fractions rich in carvacrol and the carvone in it is also It cannot be converted into products, causing great waste and serious environmental problems

Method used

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  • Method for preparing carvacrol by recycling carvone synthesis by-product
  • Method for preparing carvacrol by recycling carvone synthesis by-product
  • Method for preparing carvacrol by recycling carvone synthesis by-product

Examples

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Effect test

Embodiment 1

[0015] Under the protection of nitrogen, add 100 grams of fractions with a mass content of 83.2% of carvacrol into a 500ml flask, add 280 grams of 15% sodium hydroxide solution dropwise under stirring and cooling in a water bath, maintain the temperature at 33°C, and drop for about 4 hours. After the addition, continue to react for half an hour, stand and separate layers; the organic phase is washed with saturated brine and rectified to obtain 13 grams of carvone; the aqueous phase is under nitrogen protection, stirring and ice-water bath, and 10% hydrochloric acid with a mass concentration of 10% is added dropwise The pH value of the solution was adjusted to 5.0, the titration rate was controlled, the temperature was maintained at 25° C., the layers were left to stand, the organic phase was washed with saturated saline solution, and 80.4 g of carvacrol was obtained by rectification under reduced pressure, with a content of 99.35% and a yield of 96.6%.

Embodiment 2

[0017] Under the protection of nitrogen, add 100 grams of fractions with a mass content of 86.2% carvacrol into a 500ml flask, add 250 grams of 15% sodium hydroxide solution dropwise under stirring and cooling in a water bath, maintain the temperature at 35°C, and drop for about 4.5 hours After the addition, continue to react for half an hour, let stand and separate layers; the organic phase is washed with saturated brine, and rectified to obtain 12 grams of carvone; The pH value was 6.0, the titration rate was controlled, the temperature was maintained at 20°C, the layers were allowed to stand, the organic phase was washed with saturated saline solution, and 82.7 g of carvacrol was obtained by rectification under reduced pressure, with a content of 99.45% and a yield of 95.9%.

Embodiment 3

[0019] Under the protection of nitrogen, add 100 grams of fractions with a mass content of 85.7% carvacrol into a 500ml flask, add 280 grams of potassium hydroxide solution with a mass concentration of 17% under stirring and cooling in a water bath, and keep the temperature at 32°C for about 5 hours. After the addition, continue to react for half an hour, stand and separate layers; the organic phase is washed with saturated brine, and rectified to obtain 12.3 g of carvone; the aqueous phase is under nitrogen protection, stirring and ice-water bath, and 10% hydrochloric acid is added dropwise The pH value of the solution was adjusted to 5.5, the titration rate was controlled, the temperature was maintained at 22°C, the layers were allowed to stand, the organic phase was washed with saturated saline solution, and 83.1 g of carvacrol was obtained by rectification under reduced pressure, with a content of 99.43% and a yield of 97%.

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Abstract

The invention discloses a method for recovering and preparing carvacrol from byproducts of synthetic carvone. The method is characterized in that fractions rich in carvacrol in the production for synthesizing food-grade L-carvone are taken as raw materials; inorganic base is adopted to react with carvacrol in the fractions to prepare carvacrol salt; the carvacrol salt is dissolved in water and separated from unreacted carvone; carvacrol salt aqueous solution is subjected to acid precipitation by use of inorganic acid and is rectified to prepare carvacrol; and finished carvone products can be obtained by distilling the unreacted carvone. The method has the advantages of digesting the byproducts in carvone synthesis and preparing carvacrol from the byproducts, along with mild conditions, convenient operation, easiness for industrial implementation and good economic and social benefit.

Description

technical field [0001] The invention relates to a method for processing by-products of synthesis of spice compounds and recovering high value-added by-products, in particular to a method for recovering carvacrol from by-products in the synthesis of carvone. Background technique [0002] Carvacrol is an important product used in spices, food additives, feed additives, antioxidants, sanitation fungicides, insect repellents, preservatives, deodorants, pharmaceutical intermediates and other industries, with broad market prospects. Carvacrol has strong bactericidal and antibacterial effects of clearing away heat, removing dampness, dispelling heat, relieving the exterior, and regulating qi. It is a safe, efficient, green, and non-incompatible traditional Chinese medicine additive. [0003] Carvacrol is a colorless to pale yellow liquid with a boiling point of 237°C and a structural formula of: [0004] [0005] In the production of carvone, carvone oxime undergoes a hydrolysi...

Claims

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Application Information

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IPC IPC(8): C07C39/07C07C37/68C07C37/86
Inventor 林祥陈文昌陈兆刚许竹青
Owner 江苏宏邦化工科技有限公司
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