Method for preparing high-purity delta decalactone

A kind of decanolide and high-purity technology, which is applied in the field of preparation of high-purity butyl-decalactone, can solve problems such as difficult industrialized production, complicated reaction route, expensive raw materials, etc., and achieves low price, easy-to-obtain reaction raw materials, and high raw materials. low cost effect

Inactive Publication Date: 2011-04-13
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to solve the above-mentioned problems of expensive raw materials, complex reaction routes, low product yields, and difficulty in industrialized production, the present invention provides a kind of raw materials that are easy to obtain, has few preparation steps and simple operation, and the resulting product has high purity and is easy to realize. Industrial production, that is, a method for preparing butyl decanolactone with glutaric anhydride as raw material

Method used

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  • Method for preparing high-purity delta decalactone
  • Method for preparing high-purity delta decalactone

Examples

Experimental program
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Effect test

Embodiment 1

[0025] (1) Preparation of bromopentane Grignard reagent

[0026] Under the protection of nitrogen, add 200ml of tetrahydrofuran, 10g of magnesium flakes and a small amount of iodine into a 500ml four-necked flask equipped with electromagnetic stirring, a thermometer and a reflux condenser with a drying tube, raise the temperature to 50°C, and add dropwise 60g of tetrahydrofuran dissolved in 40ml of tetrahydrofuran Pentyl bromide, control the temperature not to exceed 70°C, after the dropwise addition, continue to stir for 1 hour to obtain the Grignard reagent of pentyl bromide;

[0027] (2), Preparation of 5-oxodecanoic acid intermediate

[0028] Under the protection of nitrogen, add 300ml of tetrahydrofuran, 36g of glutaric anhydride and 2.8g of cuprous iodide into a 1L four-neck flask, cool to -20°C, add the above-mentioned Grignard reagent of bromopentane dropwise, and the dropping time is About 1h. After the dropwise addition, continue to stir for 2 hours, add 1mol / L hyd...

Embodiment 2

[0032] (1), preparation of chloropentane Grignard reagent

[0033] Under the protection of nitrogen, add 200ml of tetrahydrofuran, 10g of magnesium flakes and a small amount of iodine into a 500ml four-necked flask equipped with electromagnetic stirring, a thermometer and a reflux condenser with a drying tube, raise the temperature to 50°C, and add dropwise 42.7 g pentane chloride, control the temperature not to exceed 70°C, after the dropwise addition, continue to stir for 1 hour to obtain the Grignard reagent of pentane chloride;

[0034] (2), Preparation of 5-oxodecanoic acid intermediate

[0035] Under the protection of nitrogen, add 300ml of tetrahydrofuran, 36g of glutaric anhydride and 2.8g of cuprous iodide into a 1L four-neck flask, cool to -20°C, add the above-mentioned Grignard reagent of chloropentane dropwise, and the dropping time is About 1h, after the dropwise addition, continue to stir for 2h, add 1mol / L hydrochloric acid solution to hydrolyze to pH=2, let st...

Embodiment 3

[0039] (1) Preparation of bromopentane Grignard reagent

[0040] With embodiment 1;

[0041] (2), Preparation of 5-oxodecanoic acid

[0042] Under the protection of nitrogen, add 300ml of tetrahydrofuran, 36g of glutaric anhydride and 4g of copper bromide into a 1L four-neck flask, cool to -20°C, add the above-mentioned Grignard reagent of bromopentane dropwise, and the dropping time is about 1h , after the dropwise addition, continue to stir for 2 hours, add 1mol / L hydrochloric acid solution to hydrolyze to pH = 2, let stand to separate the water layer, extract the water layer twice with methyl tert-butyl ether, combine the organic phases, and saturated chlorine Wash with sodium chloride solution until neutral, dry over anhydrous magnesium sulfate, and remove the solvent under reduced pressure to obtain 45.5 g of crude product 5-oxodecanoic acid;

[0043] (3), the preparation of butyl decalactone

[0044] Add 215g of 5% sodium hydroxide solution and the above-mentioned cru...

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Abstract

The invention discloses a method for preparing high-purity delta decalactone. The method for preparing the high-purity delta decalactone comprises the following steps of: adding glutaric anhydride serving as a raw material and a Grignard reagent of halogenated pentane to obtain a 5-oxodecanoic acid intermediate; and under alkalic condition, reducing the 5-oxodecanoic acid intermediate by using sodium borohydride and performing acidification cyclization to obtain the high-purity delta decalactone. The raw materials, such as the glutaric anhydride and the halogenated pentane, in the method are commercial products; and the reaction materials are readily available and low in cost. The method for preparing the high-purity delta decalactone has fewer steps and is simple in operation and easy to industrialize; the yield of the products is high; the mole yield of the products reaches 70 percent; and the purity of the products reaches over 99 percent.

Description

technical field [0001] The invention relates to a preparation method of high-purity butyl-decalactone. Background technique [0002] δ-decalactone, also known as δ-n-pentyl-δ-valerolactone or butyl-decalactone, has a strong and long-lasting creamy aroma characteristic component, and is the main fragrance for preparing milk and cream flavors. Deploying coconut, strawberry, peach and other spices, δ-decalactone is widely used in margarine, ice cream, soft drinks, candies, baked goods and seasonings, and has a large market demand. [0003] Although there are many reports on the synthesis of butyldecalactone, its synthetic routes mainly include the following two categories: the first category: firstly prepare α-pentylcyclopentanone, and then expand it by Baeyer-Villiger reaction. [0004] Cycling into butyl-decalactone. Due to the asymmetric structure of α-pentylcyclopentanone, there is a reverse insertion side reaction in the Baeyer-Villigery oxidative rearrangement reaction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/30
Inventor 赵延伟梁立冬贾卫民王之建
Owner SHANGHAI INST OF TECH
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