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Method for splitting gamma-dodecalactone chiral molecule

A technology of laurolactone and chiral molecules, which is applied in the field of fine chemical chiral separation and purification, can solve the problems of low half-volume yield and high split cost, achieve high half-volume yield, improve the quality of spices, and use effects Good results

Inactive Publication Date: 2012-05-09
JINGJIANG TAIDA PERFUME CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve the problem of low semi-mass yield and high resolution cost in the resolution of γ-dodecanolide chiral molecules in the prior art, the present invention provides a high half-mass yield with a chromatographic content of 99.9%. Above, the separation method of γ-dodecanolide chiral molecule with great value in large-scale production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] In a 500mL four-neck flask, dissolve 30g of potassium hydroxide in 250ml of water, add 112g of racemic γ-dodecylactone dropwise at 70°C under stirring at 250r / min, and continue to stir and hydrolyze for 5h at this temperature . After stirring and cooling to room temperature, 120ml of ethyl acetate was added, and then 25% sulfuric acid was added dropwise to adjust Ph=6.0. The organic layer was separated and extracted three times with ethyl acetate. Combine the organic layers, add 33.8g R-(+)-α-phenylethylamine and 12g bisphosphine terpene, heat the solution to 70°C, freeze it at -15°C for 10 hours, and filter it to obtain light white crystals. Dissolve the crystals in 100mL of water, heat to 95°C, add 1g of tartaric acid under stirring, and dropwise add 20% concentration of hydrochloric acid to cyclize the lactone to generate (S)-(-)-γ-dodecanolide. The generated (S)-(-)-γ-dodecanolide was extracted with ethyl acetate, and the extracted organic layer was dried with an a...

Embodiment 2

[0016] In a 1000mL four-neck flask, dissolve 57g of potassium hydroxide in 475ml of water, add 212.8g of racemic γ-dodecylactone dropwise at 70°C under stirring at 250r / min, and continue stirring at this temperature for hydrolysis 5h. After stirring and cooling to room temperature, 228ml of ethyl acetate was added, and then 25% sulfuric acid was added dropwise to adjust Ph=6.0. The organic layer was separated and extracted three times with ethyl acetate. Combine the organic layers, add 64.2g of S-(-)-α-phenylethylamine and 22.8g of bisphosphine terpene, heat the solution to 70°C, freeze it at -15°C for 10 hours, and filter it with suction to obtain light white crystals. Dissolve the crystals in 150mL of water, heat to 95°C, add 3g of tartaric acid under stirring, and dropwise add 20% concentration of hydrochloric acid to cyclize the lactone to generate (S)-(-)-γ-dodecanolide. The generated (S)-(-)-γ-dodecanolide was extracted with ethyl acetate, and the extracted organic laye...

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Abstract

The invention discloses a method for splitting a gamma-dodecalactone chiral molecule. The method comprises the following steps of: under the alkaline condition, hydrolyzing gamma-dodecalactone into hydroxy acid; under the action of a catalyst, reacting a chiral splitting agent R-(+)-alpha-phenyl ethylamine with optical activity and the hydroxy acid to form a hydroxyl-acid salt complex; splitting and purifying the racemized hydroxyl-acid salt complex by using a recrystallization method; and under the action of the catalyst, acidifying and cyclizing the purified product to obtain chiral gamma-dodecalactone. According to the method disclosed by the invention, the problems of low half-quantity yield and high splitting cost in the splitting process of the gamma-dodecalactone chiral molecule inthe prior art are solved; and the method for splitting the gamma-dodecalactone chiral molecule with the advantages of high half-quantity yield, chromatogram content as high as over 99.9 percent and higher utilization value in scale production is provided.

Description

technical field [0001] The invention relates to a method for splitting chiral molecules of γ-laurolactone, which belongs to the technical field of chiral separation and purification in fine chemical industry. Background technique [0002] Natural lactone flavors are mostly found in the fruits of various fruits, such as γ-butyrolactone, γ-decalactone, γ-undecalactone, γ-dodecalactone are widely found in peaches, almonds, strawberries Waiting for fruit. Lactone fragrances on the market are mainly derived from chemical synthesis. The lactone fragrances obtained by general chemical synthesis methods are all racemates. Most of the lactones in natural foods are chiral lactones, and there are obvious differences in the aroma between the dextrorotary and levorotatory forms of chiral lactones. The chiral lactone after splitting has a purer aroma than the racemic lactone fragrance, more emphasis on natural style, and higher added value. For example: (R)-(+)-γ-Lauryl lactone contai...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33C07B57/00C11B9/00
Inventor 韦宇高栋华刘萍
Owner JINGJIANG TAIDA PERFUME CHEM
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