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A kind of synthetic method of terpinolene 4,8-epoxide

A technology of terpineolene and epoxide, which is applied in the field of synthesis of terpineolene 4,8-epoxide, can solve the problems of difficult catalyst recovery, wastewater pollution oxidation selectivity, harsh reaction conditions, etc., and achieve oxidation Moderate performance, low equipment requirements, and simple treatment

Active Publication Date: 2022-03-11
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The object of the present invention is to propose a kind of terpineolene 4,8-epoxide for the problems of harsh reaction conditions, difficult catalyst recovery, waste water pollution and poor oxidation selectivity in the existing terpineolene epoxidation reaction. resolve resolution

Method used

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  • A kind of synthetic method of terpinolene 4,8-epoxide

Examples

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Effect test

Embodiment 1

[0027] Mix 10 g of terpinolene raw material (mass fraction 84%), 3 g of 2,2,2-trifluoroacetophenone, 5 g of acetonitrile and 6 g of toluene to obtain a mixture solution, which is transferred to a batch reactor 10g of 50% hydrogen peroxide solution was slowly added dropwise to the mixture solution at 30°C, and the dropping time was 2h. After the dropwise addition, continue to stir and react for 9 hours, then let it stand, collect the organic phase and the water phase after the mixture is separated, add 9 g of sodium sulfite solution (mass fraction 15%) to the organic phase, stir for 30 minutes, and remove the remaining hydrogen peroxide. The remaining organic phase was sampled for chromatographic analysis.

Embodiment 2

[0029] Mix 100 g of terpinolene raw material (mass fraction 84%), 25 g of 2,2,2-trifluoroacetophenone, 50 g of acetonitrile and 50 g of toluene to obtain a mixture solution, which is transferred to a batch reactor 180g of 30% hydrogen peroxide solution was slowly added dropwise to the mixture solution at 35°C for 2 hours. After the dropwise addition, continue to stir and react for 9 hours, then stand still, collect the organic phase and the water phase after the mixture is separated, add 92.4g of sodium sulfite solution (mass fraction 15%) to the organic phase, stir for 30 minutes, and remove the remaining hydrogen peroxide , and the remaining organic phase was sampled for chromatographic analysis.

Embodiment 3

[0031] Hexafluoroacetone was used to replace the 2,2,2-trifluoroacetophenone used in Example 1, and the addition amount was 2.9 g, and the rest of the steps were the same as in Example 1.

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Abstract

The invention discloses a method for synthesizing terpineolene 4,8-epoxide. The method uses terpineolene, a downstream product of turpentine, as a raw material, mixes it evenly with a solvent, a catalyst and a catalyst auxiliary agent, and then mixes it with A solution containing oxidant hydrogen peroxide is reacted to synthesize terpinolene 4,8-epoxide. The oxidation selectivity of the catalytic oxidation system adopted in the present invention is high, the catalyst is easy to recycle, the reagents used are environmentally friendly, the process is safe, and it is suitable for industrialized production. Under the optimal conditions of the experiment of the present invention, the conversion rate of terpinolene can reach more than 95%, and the product selectivity is more than 85%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of terpinolene 4,8-epoxide. Background technique [0002] Terpinen-4-ol has high added value and is often used as a component of synthetic flavors and fragrances. However, due to the uncertainty of supplying terpinene-4-ol with natural plants as raw materials, the industry often uses the ring of terpinene. The terpinene 4,8-epoxide obtained by the oxidation route is further reacted to obtain terpinene-4-ol, but the epoxidation reaction of terpinene is always a bottleneck of this industrial production route. This is because both the 1 and 4 carbons of terpineolene have double bonds (the structural formula is as follows), which is very active and can easily be completely oxidized to form terpineolene 1,2-4,8-diepoxy compound, which reduces the selectivity of the reaction; and the double bond has strong reactivity, and under certain conditio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/04C07D301/12
CPCC07D301/12C07D303/04Y02P20/584
Inventor 郑辉东黄元斌赵素英王莹淑曾燕茹
Owner FUZHOU UNIV
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