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Method for preparing nervonic acid

A technology for nervonic acid and methyl nervate, which is applied in the preparation of carboxylate, the preparation of organic compounds, and the preparation of carboxylate/lactone, etc., can solve the problem of low nervonic acid conversion rate, low nervonic acid yield, and nervonic acid content. Low problems, to achieve the effect of single product, broad requirements, simple production and operation

Pending Publication Date: 2019-07-16
重庆中科德馨生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to overcome the extremely low content of the existing nervonic acid in nature, it is bound to pay extremely high production costs to obtain high-purity nervonic acid directly through plant extraction, and the conversion rate of the preparation of nervonic acid in the existing literature is very low Or high cost and other defects, provide a method that can efficiently prepare nervonic acid, and solve the problems of low output and high price of nervonic acid at this stage

Method used

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  • Method for preparing nervonic acid
  • Method for preparing nervonic acid
  • Method for preparing nervonic acid

Examples

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Effect test

Embodiment 1

[0023] (1) Synthesis of ethyl erucate: the synthetic route is attached figure 1 . Mix 30.0g of erucic acid, 70.2g of cyclohexane, 118.3g of ethanol and 2.8g of concentrated sulfuric acid, heat to 80°C, reflux and stir at a stirring rate of 500r / min for 6h, after the reaction of the raw materials is complete, spin off the solvent to obtain mustard ethyl acetate;

[0024] (2) Synthesis of mustard alcohol: the synthetic route is attached figure 2 . Mix 55.2g and 115.5g red aluminum solutions with petroleum ether, add 35.0g ethyl erucate obtained in step (1) dropwise to the above mixture and react at room temperature for 8h, then slowly add 2M hydrochloric acid until there are no bubbles After generation, the filtrate is collected by filtration, and the oil phase is taken after the filtrate is separated, and the solvent is spin-dried to obtain erucitol;

[0025] (3) Synthesis of mustard bromide: the synthetic route is attached image 3 . Under an ice-water bath, drop 17.8g ...

Embodiment 2

[0030] (1) Synthesis of ethyl erucate: the synthetic route is attached figure 1 . Mix erucic acid 30.0g, cyclohexane 70.2g, ethanol 118.3g and concentrated sulfuric acid 5.6g evenly, heat to 80°C, reflux and stir at a stirring rate of 500r / min for 6h, after the raw materials have reacted completely, spin off the solvent to obtain mustard ethyl acetate;

[0031] (2) Synthesis of mustard alcohol: the synthetic route is attached figure 2 . Same as example 1;

[0032] (3) Synthesis of mustard bromide: the synthetic route is attached image 3 . Same as example 1;

[0033] (4) Synthesis of mustard bromide docking dimethyl malonate: see attached for the synthetic route Figure 4 . Same as example 1;

[0034] (5) Synthesis of nervonic acid methyl ester: see the appendix for the synthetic route Figure 5 . Same as example 1;

[0035] (6) Synthesis of nervonic acid: see attached for the synthetic route Figure 6 . With example 1, obtain purity and be 93% nervonic acid pro...

Embodiment 3

[0037] (1) Synthesis of ethyl erucate: the synthetic route is attached figure 1. Mix 30.0g of erucic acid, 70.2g of cyclohexane, 118.3g of ethanol and 1.8g of concentrated sulfuric acid, heat to 80°C, and stir under reflux at a stirring rate of 500r / min for 6h. After the raw materials are completely reacted, spin off the solvent to obtain mustard ethyl acetate;

[0038] (2) Synthesis of mustard alcohol: the synthetic route is attached figure 2 . Same as example 1;

[0039] (3) Synthesis of mustard bromide: the synthetic route is attached image 3 . Same as example 1;

[0040] (4) Synthesis of mustard bromide docking dimethyl malonate: see attached for the synthetic route Figure 4 . Same as example 1;

[0041] (5) Synthesis of nervonic acid methyl ester: see the appendix for the synthetic route Figure 5 . Same as example 1;

[0042] (6) Synthesis of nervonic acid: see attached for the synthetic route Figure 6 . With example 1, obtain purity and be 92% nervonic...

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Abstract

The invention relates to a method for preparing nervonic acid. According to the method, erucic acid is uses as the starting raw material to first prepare erucic acid ethyl ester, then erucic acid ethyl ester is converted into docosa-13-en-1-ol, then docosa-13-en-1-ol is converted into docosa-13-en-1-bromine, then docosa-13-en-1-bromine is subjected to a reaction to obtain 2-(docosa-13-en-1-yl)-malonic acid dimethyl ester, then 2-(docosa-13-en-1-yl)-malonic acid dimethyl ester is converted into nervonic acid methyl ester by a reaction, and finally nervonic acid methyl ester is hydrolyzed to obtain nervonic acid. The method can be used for the scale preparation of nervonic acid. The method has a single product, the comprehensive conversion rate is up to 50% or more, and the nervonic acid product with 90% or more of high purity can be obtained. The method has simple production operation and low equipment requirements, and greatly reduces the production cost of nervonic acid.

Description

technical field [0001] The invention relates to a preparation method of nervonic acid, which belongs to the field of chemical synthesis for preparing medicine and its intermediates. Background technique [0002] Nervous acid, English name: Nervonic Acid, scientific name: Cis-15-Tatracosanic Acidl, alias: Salacholaic Acid, is a monounsaturated fatty acid, its structure As shown in formula I. The active form of naturally occurring nervonic acid has all the double bonds at position 15 in cis. Nervous acid is a physiologically active substance that exists in animal nerve tissue and brain tissue. It was first isolated from shark brain and cow brain. The double-effect magical substance that promotes the regeneration of nerve cells has the function of restoring the activity of nerve endings, promoting the growth and development of nerve cells, and plays an important role in improving the activity of cranial nerves and preventing cranial neurasthenia. Neural acid is mainly used t...

Claims

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Application Information

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IPC IPC(8): C07C27/02C07C57/03
CPCC07C67/08C07C29/147C07C17/16C07C67/343C07C67/32C07C51/09C07C69/533C07C33/025C07C21/14C07C69/593C07C57/03
Inventor 张天毛羽张楹川
Owner 重庆中科德馨生物科技有限公司
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