Method for synthesis of long-chain fatty acid ester derivative

A technology for long-chain fatty acids and derivatives, which is applied in the field of synthesizing long-chain fatty acid lipid derivatives, can solve the problems of rising product cost, increased synthesis steps, etc., and achieves reduction of waste discharge, pollution-free post-processing, and simple post-processing. Effect

Active Publication Date: 2019-12-31
PANASIA OLAUGHLIN BIO TECH WUHAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the yield of the indirect synthesis method will increase, the cost of the product will also increase due to the increase in the number of synthesis steps.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the preparation of ethyl laurate

[0018] Add 150mL absolute ethanol, 40g (0.2mol) lauric acid in the 500mL three-neck flask that thermometer and water separator are housed, add 50mL cyclohexane and 2.52g (0.02mol) glycine methyl ester hydrochloride after stirring and mixing uniformly, The temperature was raised to reflux (at a temperature of 78° C.) for 6 hours. After cooling down to room temperature, concentrate to recover the solvent, add 50 mL of water to the concentrate, and then add 150 mL of ethyl acetate to extract once. The ethyl acetate layer was washed twice with 5% aqueous sodium chloride solution, 50 mL each time. Obtain 48.4 grams of final product crude product after ethyl acetate layer is concentrated, underpressure distillation, collect 174-179oC / 0.06MPa product, obtain final product ethyl laurate 33.8 grams, final product is light yellow oily liquid, the purity of gas chromatography inspection The reaction yield was 97.2%, and the reacti...

Embodiment 2

[0019] Embodiment 2: the preparation of methyl laurate

[0020] Add 150mL methanol, 40g (0.2mol) lauric acid in the 500mL there-necked flask that thermometer and water separator are housed, add 50mL hexanaphthene and 2.52g (0.02mol) glycine methyl ester hydrochloride after stirring and mixing, be warming up to Reflux (at a temperature of 70° C.) for 8 hours. After cooling down to room temperature, concentrate to recover the solvent, add 50 mL of water to the concentrate, and then add 150 mL of ethyl acetate to extract once. The ethyl acetate layer was washed twice with 5% aqueous sodium chloride solution, 50 mL each time. Obtain 43.1 grams of final product crude product after ethyl acetate layer is concentrated, underpressure distillation, collect 151-157oC / 0.06MPa product, obtain final product methyl laurate 34.7 grams, final product is light yellow oily liquid, the purity of gas chromatography inspection The reaction yield was 98.3%, and the reaction yield was 81%, and the...

Embodiment 3

[0021] Embodiment 3: the preparation of ethyl laurate

[0022] Add 150mL absolute ethanol, 40g (0.2mol) lauric acid in the 500mL three-neck flask that thermometer and water separator are housed, add 50mL cyclohexane and 2.8g (0.02mol) ethyl glycine hydrochloride after stirring and mixing, The temperature was raised to reflux (at a temperature of 78° C.) for 6 hours. After cooling down to room temperature, concentrate to recover the solvent, add 50 mL of water to the concentrate, and then add 150 mL of ethyl acetate to extract once. The ethyl acetate layer was washed twice with 5% aqueous sodium chloride solution, 50 mL each time. Obtain 43.4 grams of final product crude product after ethyl acetate layer is concentrated, underpressure distillation, collect 174-179oC / 0.06MPa product, obtain final product ethyl laurate 32.0 grams, final product is light yellow oily liquid, the purity of gas chromatography inspection The reaction yield was 97.7%, and the reaction yield was 70%. ...

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PUM

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Abstract

The invention relates to a method for synthesis of a long-chain fatty acid ester derivative. Specifically, a hydrochloride of glycine methyl ester or glycine ethyl ester is used as a catalyst to catalyze the esterification reaction of long-chain fatty acid. The method includes: subjecting alcohol and long-chain fatty acid to esterification reaction under the action of the catalyst at certain temperature condition, then conducting extraction and precipitation with ethyl acetate, performing flushing with a sodium chloride aqueous solution for purification. A hydrochloride of glycine methyl esteror glycine ethyl ester is adopted as the catalyst, which belongs to a green catalyst, is the development trend of modern chemistry, has the characteristics of no corrosion to the reaction kettle, lowprice, no toxicity and the like, and is suitable for use as a catalyst to produce palmitate and laurate perfume raw materials.

Description

technical field [0001] The invention relates to a method for synthesizing long-chain fatty acid lipid derivatives. Specifically, the hydrochloride of glycine methyl ester and glycine ethyl ester is used as a catalyst to catalyze the esterification reaction of long-chain fatty acid. Background technique [0002] Ester derivatives of long-chain fatty acids (palmitic acid, lauric acid, etc.) are an important fragrance raw material. The industrial synthesis has a direct synthesis method, that is, the fatty acid and the corresponding alcohol undergo an esterification reaction in the presence of a catalyst. Commonly used catalysts include inorganic acids such as sulfuric acid, organic acids such as p-toluenesulfonic acid, Lewis acids such as aluminum chloride, ferric chloride, and acidic ion exchange resins supported by polymer materials. Unlike short-chain and medium-chain fatty acids, the reaction of long-chain fatty acids with alcohols is generally slow and the yield is low du...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C67/58C07C67/54C07C69/24
CPCC07C67/08C07C67/58C07C67/54C07C69/24
Inventor 陈臻
Owner PANASIA OLAUGHLIN BIO TECH WUHAN CO LTD
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