A synthetic method of chiral gamma-decalactone

A synthesis method and decanolide technology, applied in the field of essence, can solve the problems of low fermentation yield, no industrialization conditions, and high strain requirements, and achieve the effects of easy synthesis, easy production and operation, and moderate pressure.

Inactive Publication Date: 2017-08-29
TIANJIN ANKAITE CATALYST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, relatively pure products with optical activity can be obtained by biological methods, and the production process that requires many steps by chemical synthesis can be completed at one time, but the fermentation yield of this process is very low, and the requirements for bacterial strains are very high. Ready for industrialization

Method used

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  • A synthetic method of chiral gamma-decalactone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthetic method of described chiral gamma-decalactone, this synthetic method comprises the steps:

[0032] (1) Add 1.62g of concentrated sulfuric acid in 54ml of methanol, then add 0.045g of ruthenium chloride, 0.18g of BINAP, 0.9g of benzyltriethylammonium chloride, and finally add 18g of methyl 4-carbonyldecanoate to react;

[0033] (2) Transfer the reactants obtained in step (1) to the autoclave, cover the autoclave, replace the air in the autoclave with hydrogen for 3 times, then pressurize at 3.0Mpa, stir and heat up to 90°C, and pressurize the hydrogen Increase to 5.0Mpa, the reaction time is 8 hours;

[0034] (3) The reactant obtained in step (2) is neutralized, filtered, solvent recovered, and distilled to obtain the chiral γ-decalactone. The chromatographic analysis raw material content is 2.26%, and the (R) isomer is 94.39%. , (S) isomer 1.85%, calculated ee value 96.2%.

[0035] Described methyl 4-carbonyldecanoate is prepared by the method comprising ...

Embodiment 2

[0037] The synthetic method of described chiral gamma-decalactone, this synthetic method comprises the steps:

[0038] (1) Add 1.62g of concentrated sulfuric acid to 54ml of methanol, then add 0.045g of palladium chloride, 0.18g of BINAP, 0.9g of benzyltriethylammonium chloride, and finally add 18g of methyl 4-carbonyldecanoate to react;

[0039] (2) Transfer the reactants obtained in step (1) to the autoclave, cover the autoclave, replace the air in the autoclave with hydrogen for 3 times, then pressurize at 3.0Mpa, stir and heat up to 90°C, and pressurize the hydrogen Increase to 5.0Mpa, the reaction time is 8 hours;

[0040] (3) The reactant obtained in step (2) is neutralized, filtered, solvent recovered, and distilled to obtain the chiral gamma-decalactone, the chromatographic analysis raw material content is 2.6%, (R) isomer 93.33% , (S) isomer 2.27%, calculated ee value 95.3%.

[0041] Described methyl 4-carbonyldecanoate is prepared by the method comprising the follo...

Embodiment 3

[0043] The synthetic method of described chiral gamma-decalactone, this synthetic method comprises the steps:

[0044] (1) Add 1.62g concentrated sulfuric acid in 54ml methanol, then add rhodium chloride 0.045g, 0.18g BINAP, benzyltriethylammonium chloride 0.9g, finally add 4-carbonyldecanoic acid methyl ester 18g and react;

[0045] (2) Transfer the reactants obtained in step (1) to the autoclave, cover the autoclave, replace the air in the autoclave with hydrogen for 3 times, then pressurize at 3.0Mpa, stir and heat up to 90°C, and pressurize the hydrogen Increase to 5.0Mpa, the reaction time is 8 hours;

[0046] (3) The reactant obtained in step (2) is neutralized, filtered, solvent recovered, and distilled to obtain the chiral γ-decalactone. The raw material content of chromatographic analysis is 1.6%, and the (R) isomer is 93.93%. , (S) isomer 2.43%, calculated ee value 95.0%.

[0047] Described methyl 4-carbonyldecanoate is prepared by the method comprising the followi...

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Abstract

A synthetic method of chiral gamma-decalactone is provided. The method includes steps of (1) adding concentrated sulfuric acid into an organic solvent, then adding a catalyst, a ligand and a phase-transfer catalyst into the mixture, finally adding methyl 4-carbonyldecanoate into the mixture, and reacting the mixture; (2) transferring a reaction product obtained in the step (1) into an autoclave, and filling the autoclave with hydrogen to pressurize the autoclave to 3-6 MPa, with the reaction temperature being 60-120 DEG C and reaction time being 4-8 h; and (3) subjecting a reaction product obtained in the step (2) to neutralization, filtration, solvent recovery and distillation to obtain the chiral gamma-decalactone. The reaction temperature and pressure of the method are proper, and production operation is easy so that the method can be used for industrial production. The ee value of the product can be 95% or above.

Description

technical field [0001] The invention belongs to the field of essences, and in particular relates to a synthesis method of chiral gamma-decalactone. Background technique [0002] γ-Decalactone exists in peaches, almonds, strawberries and other fruits, and has a strong fruity aroma. A large number of studies have found that (R) isomers and (S) isomers have different aroma characteristics, and the production of chiral lactones has been paid attention to in the fragrance and fragrance industry. [0003] The gamma-decalactone currently on the market is still mainly a non-optical active racemic mixture synthesized by chemical methods. The common chemical synthesis of gamma-decalactone is mainly the condensation of octanal and malonic acid, and then deacidification ring turned into. However, relatively pure products with optical activity can be obtained by biological methods, and the production process that requires many steps by chemical synthesis can be completed at one time, b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor 王广柏高永鑫高志国
Owner TIANJIN ANKAITE CATALYST
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