Preparation method of chiral gamma-decalactone

A decanolactone and chiral technology, which is applied in the field of preparation of chiral γ-decalactone, can solve the problems of high extraction and refining costs, low half-quantity yield, harsh operating conditions, etc., and achieves industrialization and high efficiency. Enantiomeric excess value, effect of reducing production difficulty

Inactive Publication Date: 2018-07-20
博润生物科技南通有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since microbial metabolites and target products have inhibitory and toxic effects on microorganisms, the concentration of target products is often maintained at a low level, and most of the aroma substances have strong volatility and low water solubility. Therefore, the extraction and refining costs are very high
2. Using chemical asymmetric synthesis, but most of them are in the research stage, and there are still very few methods that can be used in

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Add 262g of NaOH and 3000g of water into a 10L three-necked flask, heat to 60°C, add 750g (4.40mol) of racemic γ-decalactone dropwise, finish adding dropwise in half an hour, react for 2h until there is no oil layer, and cool the reaction solution to 30°C, add 2000g of ethyl acetate, dropwise add sulfuric acid with a mass concentration of 80% to PH=5, separate the liquid to separate the oil layer, extract the water phase with 200g of ethyl acetate twice, combine the oil phase, discard the water phase, and Phase is dried with 100g anhydrous sodium sulfate, filters to obtain gamma-hydroxyacid ethyl acetate filtrate;

[0026] (2) Add 530g of S-α-phenylethylamine (4.37mol) to the filtrate, raise the temperature to 40°C, stir and cool down to 0°C, crystals precipitate out, and filter to obtain γ-hydroxy acid S-α-phenylethylamine with low optical activity Amine salt filter cake;

[0027] (3) Add 4 times the amount of water to the amine salt filter cake, heat to 60°C to d...

Embodiment 2

[0032](1) Add 90g of NaOH and 900g of water into a 3L three-necked flask, heat to 60°C, add 258g (1.52mol) of racemic γ-decalactone dropwise, finish adding dropwise in 10min, react for 1.5h until there is no oil layer, and cool the reaction solution to room temperature, add 600 g of ethyl acetate, dropwise add sulfuric acid with a mass fraction of 80% to PH=5, separate the oil layer, extract the water phase with 65 g of ethyl acetate twice, combine the oil phase, discard the water phase, and Dry with 30g of anhydrous sodium sulfate, filter to obtain gamma-hydroxyacid ethyl acetate filtrate;

[0033] (2) Add 220g of recovered S-α-phenylethylamine (1.82mol) to the filtrate, raise the temperature to 40°C, stir and cool down to 0°C, crystals precipitate, filter and wash with ethyl acetate to obtain γ-hydroxyl with low optical activity Acid S-α-phenethylamine salt filter cake;

[0034] (3) Add 4 times the amount of water to the amine salt filter cake, heat to 60°C to dissolve, the...

Embodiment 3

[0039] (1) Add 57.6g of NaOH and 672g of water into a 2L three-necked flask, heat to 60°C, add 163.2g (0.96mol) of racemic γ-decalactone dropwise, finish adding dropwise in 10 minutes, and react for 1 hour until there is no oil layer. Cool to room temperature, add 600 g of ethyl acetate, dropwise add sulfuric acid with a mass fraction of 80% to PH=5, separate the oil layer, extract the water phase with 150 g of ethyl acetate twice, combine the oil phase, discard the water phase, and Phase is dried with 30g anhydrous sodium sulfate, filters to obtain gamma-hydroxyacid ethyl acetate filtrate;

[0040] (2) Add 116.4g S-α-phenylethylamine (0.96mol) to the filtrate, raise the temperature to 40°C, stir and cool down to 20°C, crystals precipitate, filter, and wash with ethyl acetate to obtain γ-hydroxy acid with low optical activity S-α-phenethylamine salt filter cake;

[0041] (3) Add 4 times the amount of water to the filter cake, heat it to 60°C to dissolve, then cool down to 20°...

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PUM

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Abstract

The invention discloses a preparation method of chiral gamma-decalactone. The method comprises the following steps that (1) racemic gamma-decalactone is subjected to loop opening by an inorganic alkali solution to obtain a gamma-hydroxy acid and alkali metal saline solution; then, an organic solvent is added; the PH value is regulated to a weak acid state by inorganic acid, so that generated gamma-hydroxy acid enters an organic phase; the separated organic phase is dried; (2) (S)-(-)-alpha-phenylethylamine is added into the organic phase; crystallization is performed to separate out gamma-hydroxy acid (S)-(-)-alpha-phenylethylamine salt with optical activity; (3) obtained amine salt is added into water; stirring, dissolution, crystallization and filtering are performed; after filter cake is added with water to be dissolved, inorganic acid is added; after acidification cyclization, an organic solvent is added for extraction to obtain (R)-(+)-gamma-decalactone; (4) inorganic acid is added into crystallization mother liquid in the steps (2) and (3) for further acidizing treatment; the organic solvent is used for extraction to obtain (S)-(-)-gamma-decalactone. When the preparation method is used, the operation is easy; two kinds of configuration of chiral gamma-decalactone can be obtained; the fragrance is pure, the advantages of high-half-quantity yield, high enantiomer excess values and low cost are realized.

Description

technical field [0001] The invention relates to a preparation method of chiral lactone, in particular to a preparation method of chiral γ-decalactone. Background technique [0002] Gamma-decalactone (4-hexylbutyrolactone) occurs naturally in fruits such as peaches, almonds, and strawberries. It has a strong fruity aroma and peach aroma when diluted. It is mainly used in the preparation of food, soap, daily cosmetic essence, and can also be used as a margarine flavor enhancer. [0003] The aroma of (S)-(-)-γ-decalactone is soft, sweet coconut milk, with obvious fat color, with fruity, banana, lactone and jasmine-like top notes. The main aroma is very close to the raceme, but the aroma is fuller, the sweet and floral aroma is weaker, but the aroma is stronger and the lactone aroma is more obvious. Its specific rotation: [α] D 20 =-48.1° (c=1.5~2.5, CH 3 OH). [0004] (R)-(+)-γ-Decalactone has an intense, fat-sweet fruity, coconut-like, caramel flavor. Very suitable for...

Claims

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Application Information

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IPC IPC(8): C07D307/33
CPCC07D307/33C07B2200/07
Inventor 王文瀚蔡茂军陈冬权夏伟峰张宏顺
Owner 博润生物科技南通有限公司
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