Exaltolide preparing process from garlic oil

A technology of cyclopentadecanolactone and garlic fruit oil, applied in the direction of organic chemistry, etc., to achieve the effects of reducing reaction steps, high total yield, and simplifying the process

Inactive Publication Date: 2004-07-07
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The technical problem to be solved by the present invention is to simplify the process of producing cyclopentadecanolide from garlic fruit oil, to improve the utilization rate of active ingredients in garlic fruit oil under the condition of industrialized production, to reduce environmental pollution, and to reduce environmental pollution as much as possible. Produce as much high-quality cyclopentadecanolide as possible at low cost

Method used

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  • Exaltolide preparing process from garlic oil
  • Exaltolide preparing process from garlic oil
  • Exaltolide preparing process from garlic oil

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] 2400 grams of garlic fruit oil (about 30% of the mass content of tetracos-15-enoic acid) and 5600 grams of sherwood oil are mixed and put into a gas-liquid reactor, and ozone is fed into the reaction at 20 ° C. When the reaction reaches the end Afterwards, an aqueous solution containing 800 g of potassium borohydride was slowly added dropwise under stirring at 25° C., and the reaction time was 4 hours. Then use sulfuric acid to adjust PH=6~7, stand to separate layers, take the oil layer and heat to evaporate solvent to obtain 2100 grams of hydroxyglycerides. Take 240 grams of hydroxyglycerides and put them into a three-necked flask, add 18 grams of sodium methoxide, heat the reaction solution to 180-230° C. under a vacuum of 3-10 mmHg, and react for 12 hours to obtain 188 grams of the product. After rectification and ethanol crystallization, 48 grams of cyclopentadecanolide with a purity of 98.5% were obtained. The total yield was (2100 / 2400) x (48 / 240) = 17.5%.

Embodiment 2

[0018] 300 grams of garlic fruit oil (about 50% of the mass content of tetracos-15-enoic acid) is mixed with 1000 grams of sherwood oil and 500 grams of ethanol and put into a gas-liquid reactor, and then feed ozone at 10°C for reaction. After the reaction reaches the end point, an aqueous solution containing 65 g of potassium borohydride is slowly added dropwise under stirring at 25° C., and the reaction time is 4 hours. Then use sulfuric acid to adjust PH=6~7, let stand to separate layers, take the oil layer and heat to evaporate solvent to obtain 265 grams of hydroxyglycerides. Take 180 grams of hydroxyglycerides and put them into the reactor, add 7 grams of sodium methoxide, heat the reaction solution to 180-230° C. under a vacuum of 3-10 mmHg, add glycerin as an entrainer for entrainment distillation, and react for 12 hours to obtain the product 130 gram. After rectification and ethanol crystallization, 59 grams of cyclopentadecanolide with a purity of 98.5% were obtaine...

Embodiment 3

[0020] The manufacture method of hydroxyglyceride is with embodiment 2. Take 180 grams of hydroxyglycerides into the reactor, add 9 grams of sodium methoxide, heat the reaction solution to 180-230 ° C under a vacuum of 3-10 mmHg, add glycerin as an entrainer for entrainment distillation, and react for 16 hours to obtain 136 grams of the product. After rectification and ethanol crystallization, 61 grams of cyclopentadecanolide with a purity of 98.5 were obtained. The total yield was (61 / 180)=33.9%.

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Abstract

The method for extracting cyclopentadecanolide from oil of garlic includes the following steps: adding reaction solvent into oil of garlic, then introducing ozone into said mixture containing oil of garlic, and adding reducing agent to said obtained ozonized glyceride intermediate to make reaction to obtain hydroxyglyceride containing pentadecacarbon, then in the presence of proper catalyst, making said product produce direct cyclization reaction to obtain mixed macrolide containing cyclopentadecanolide, then making said product undergo the processes of separation and purification to obtain the invented cyclopentadecanolide.

Description

technical field [0001] The invention belongs to the field of preparation method of macrocyclic lactone, especially cyclopentadecanolide. Background technique [0002] Garlic fruit (Malania oleifera Chun et Lee), native name Jatropha, is a woody oil plant distributed in Guangxi and Yunnan. After analysis and identification, the molecular formula of its seed oil (i.e. garlic fruit oil) is the following glyceride: [0003] where R 1 , R 2 , R 3 Alkenyl with carbon chain 15-25 [0004] As cyclopentadecanolactone has been more and more widely used in pharmaceutical products and high-grade perfume industries, more and more researches have been done on its production and preparation. There have been reports in the literature on the preparation of pentadecylactone (the same compound as cyclopentadecanolide) by using garlic fruit oil under laboratory conditions (see "Acta Chemica Sinica" 1987.45 volume 1217-1218, Guo Maodao, etc.) (hereinafter refer...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D313/00
Inventor 刘雄民李伟光李飘英
Owner GUANGXI UNIV
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