Synthesis method of chiral gamma-dodecalactone

A technology of laurolactone and a synthesis method, which is applied in the field of synthesis of chiral γ-dodecolactone, can solve the problems of obvious artificial traces, poor use effect, turbid aroma of spices, etc., and achieves simple process operation and added value. High, spice fragrance pure effect

Inactive Publication Date: 2012-03-28
JINGJIANG TAIDA PERFUME CHEM
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problem that the γ-laurolactone fragrance in the prior art is mainly derived from chemical synthesis, the lactone fragrance obtained by using non-optical substances under general conditions is a racemate, the fragrance of the fragrance is relatively turbid, and the impurity gas Many, ar

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0014] In a 2000mL four-necked flask equipped with a stirrer, add 1000g of nonanol, add 20g of R-(+)-α-phenylethylamine zinc ruthenium acetate organic complex, stir and heat to 175°C, and dropwise add 100g of nonanol: 110g of acrylic acid: 2g of L tartaric acid: 3g of peroxide, after proportioning nonanol and acrylic acid, the reactants are reacted in a reactor equipped with a silica-alumina mixed catalyst with a mass ratio of 1:2. A reaction mixture containing (S)-(-)-γ-laudecanolide was obtained. The reaction mixture was roughly distilled to obtain (S)-(-)-γ-laurolactone crude product, and after vacuum distillation, 123 g of (S)-(-)-γ-laurolactone was obtained. The enantiomeric excess value was 90%. The product yield is 44.8%

Embodiment 2

[0016] In a 2000mL four-neck flask equipped with a stirrer, add 1350g of nonanol, add 18g of S-(-)-α-phenylethylamine acetate copper chromium organic complex, stir and heat to 180°C, and dropwise add 134g of nonanol: Acrylic acid 120g: D tartaric acid 2g: peroxide 3g Proportion ratio of nonanol and acrylic acid ratio liquid, the reactants are reacted through a reactor equipped with a silica-alumina mixed catalyst with a mass ratio of 1:2, A reaction mixture containing (R)-(+)-γ-dodecanolide was obtained. The reaction mixture was roughly distilled to obtain crude (R)-(+)-γ-laurolactone, and after vacuum distillation, 108 g of (R)-(+)-γ-laurolactone was obtained. The enantiomeric excess value was 91%. The product yield is 39.4%.

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Abstract

The invention discloses a synthesis method of chiral gamma-dodecalactone. The method comprises the following steps of: synthesizing a lactone molecule with optical activity from a reactant under the environment and induction of a chiral molecule; proportionally mixing nonanol, acrylic acid and peroxide, and adding a certain amount of chiral alpha-phenylethylamine zinc acetate ruthenium or copper chromium organic complex into the reaction backing material; and synthesizing the gamma-dodecalactone with optical cavity under the action of silica-alumina mixed catalyst and the induction of D or L tartaric acid. Through the invention, the problems that the gamma-dodecalactone spice is mainly made by chemical synthesis in the prior art, the lactone spices synthesized from a substance without optical activity under general conditions are all racemic mixtures with turbid aroma, lots of foreign gases and relatively obvious artificial traces; and the synthesis method of chiral gamma-dodecalactone provided by the invention is easy to operate, has a relatively good use effect; and the synthesized product has a relatively high enantiomeric excess value and the aroma of the spice is more fresh.

Description

technical field [0001] The invention relates to a preparation method of chiral synthetic perfume, in particular to a synthesis method of chiral γ-laurolactone. Background technique [0002] Natural lactone flavors are mostly found in the fruits of various fruits, such as γ-decalactone, γ-undecalactone, and γ-laurolactone, which are widely found in peaches, almonds, strawberries and other fruits. For example, γ-undecalactone, also known as peach aldehyde, has a strong peach aroma, and its appearance is a colorless to light yellow viscous liquid, insoluble in water and glycerin, soluble in organic solvents such as ethanol. They are widely used in the formulation of food flavors and daily cosmetic flavors. [0003] Lactone fragrances currently on the market are mainly derived from chemical synthesis. The lactone fragrances obtained by synthesis method under general conditions with non-optical active substances are all racemates. The synthetic fragrance of the racemate has a ...

Claims

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Application Information

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IPC IPC(8): C07D307/33C07B53/00
Inventor 韦宇高栋华刘萍
Owner JINGJIANG TAIDA PERFUME CHEM
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