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Method for synthesizing chiral carvone from chiral 8-hydroxycarvone

A technology of hydroxycarvone and carvone, applied in the chemical field, can solve problems such as unfavorable industrialized production, complicated reaction route, expensive gold catalyst, etc., and achieve the effects of good industrial application prospect, high reaction efficiency, and reduced production cost.

Active Publication Date: 2021-03-05
江苏宏邦化工科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method of chiral L-carvone is mainly obtained by oxidation of chiral carveol, as reported by Kazuaki Ishihara (Journal of the American Chemical Society, 2009, 131, 251) catalyzed by 2-iodobenzenesulfonic acid to L-carvone was synthesized in 91% yield; Oscar Navarro (Journal of Organic Chemistry, 2011, 76, 1390) introduced the oxidation of chiral carveol catalyzed by carbene palladium catalyst under microwave, and L-carvone was obtained in 93% yield , but the catalyst is very expensive, and the microwave reaction is not conducive to industrial production; Qin Huali (Advanced Synthesis & Catalysis, 2019, 361, 2262) reported that the target ketone product was obtained with a yield of 68%, but the highly toxic sulfuryl fluorine
In addition, there are methods to reduce the corresponding chiral oxime, for example, Jordi Burés and Jaume Vilarrasa (Angewandte Chemie International Edition 2011, 50, 3275) developed a method of gold-catalyzed reduction of the corresponding chiral oxime to obtain L-carvone, but the gold catalyst It is also very expensive; patent CN106748707 reports the chlorination, dehydrochlorination and hydrolysis of limonene to obtain L-carvone. The reaction yield of each step of the method is all high, but the reaction route is complicated

Method used

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  • Method for synthesizing chiral carvone from chiral 8-hydroxycarvone

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Experimental program
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Effect test

Embodiment 1

[0022] Add 500g of L-8-hydroxycarvone, 100g of mesitylene and 100g of catalyst (copper supported on carbon media material, copper content is 3wt%) into a 1000 mL reactor, then react at 160~170℃ for about 6~ After 7 hours, GC showed that after the reaction was over, the catalyst was removed by filtration, and the filtrate was rectified under reduced pressure to reclaim 98 g of the catalyst and 96 g of mesitylene as a solvent. %. The catalyst obtained by filtration can be reused.

Embodiment 2

[0024] Add 500g of L-8-hydroxycarvone, 60g of diphenyl ether and 98g of the catalyst recovered in Example 1 into a 1000 mL reactor, then react at 210-230°C for about 2-3 hours, after GC shows that the reaction is over, filter The catalyst was removed, the filtrate was rectified under reduced pressure, and 96g of the catalyst was recovered, and further rectified to obtain 427g of L-carvone finished product with a content greater than 97%, with a yield of 96%. The catalyst obtained by filtration can be reused.

Embodiment 3

[0026] Add 500g of L-8-hydroxycarvone, 150g of N-methylpyrrolidone and 96g of the catalyst recovered in Example 2 into a 1000 mL reactor, then react at 190 to 200°C for about 5 to 6 hours, and GC shows that after the reaction ends, The catalyst was removed by filtration, and the filtrate was rectified under reduced pressure to recover 92 g of the catalyst, and further rectified to obtain 421 g of L-carvone finished product with a content greater than 97%, with a yield of 94%. The catalyst obtained by filtration can be reused.

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Abstract

The invention discloses a method for synthesizing chiral carvone from chiral 8-hydroxycarvone. The method comprises the following steps: dissolving chiral 8-hydroxycarvone and a catalyst in a solvent,carrying out heating to realize an end removal reaction of chiral 8-hydroxycarvone so as to generate chiral carvone, conducting filtering after the reaction is finished so as to separate the catalyst, carrying out vacuum distillation on the filtrate, recovering the solvent to obtain, and further conducting rectification under vacuum to obtain a finished chiral carvone product. The catalyst is a carbon-based composite catalyst. According to the method, the carvone is synthesized by taking chiral 8-hydroxycarvone as a raw material; the method is a brand-new chiral carvone synthesis method; thecomprehensive utilization of existing levo-8-hydroxycarvone is realized; the application range of 8-hydroxycarvone is expanded; and the production cost of the levo-carvone is reduced.

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 chiral carvone with chiral 8-hydroxy carvone. [0002] technical background [0003] L-carvone (D-Carvone) is an important spice with the aroma of parsley, dill seeds and black bread, widely used in food industry and chemical industry, especially in toothpaste, hard candy, chewing gum and various beverages middle. Carvone generally refers to spearmint oil, also known as peppermint herb oil, spearmint oil or spearmint oil, and its main component is L-carvone. Its usage continues to grow, especially in China, and its synthesis method has always been concerned by researchers. [0004] At present, the naturally extracted carvone is in the form of mixed rotation, but limited by natural conditions, seasons and regions, the output is small and the price is expensive. The synthesis is also based on the mixed...

Claims

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Application Information

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IPC IPC(8): C07C49/647C07C45/65
CPCC07C45/65C07B2200/07C07C49/647Y02P20/584
Inventor 刘晓涛张万斌陈建中张振锋彭优斌管静魏瀚林胡雅雯
Owner 江苏宏邦化工科技有限公司
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