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A kind of preparation method of nitrooleic acid and its derivatives

A technology of nitrooleic acid and its derivatives, which is applied in the preparation of nitrooleic acid or nitrooleic acid methyl ester, and in the field of preparation of nitrooleic acid and its derivatives. It can solve problems such as complex methods and achieve synthesis steps simple effect

Active Publication Date: 2016-01-20
INNOBIO CORP LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the current synthesis of nitrooleic acid using toxic raw materials and complex methods, the purpose of the present invention is to propose a "one-step method" to prepare nitrooleic acid and nitrooleic acid methyl ester. This method does not need to use toxic raw materials, is environmentally friendly, and The method is simple and easy

Method used

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  • A kind of preparation method of nitrooleic acid and its derivatives
  • A kind of preparation method of nitrooleic acid and its derivatives
  • A kind of preparation method of nitrooleic acid and its derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Weigh 0.592 g (0.002 mol) of the purified methyl oleate, dissolve it in 20 ml of n-hexane dewatered by molecular sieves, and obtain a methyl oleate solution. Prepare 160ml of sulfuric acid aqueous solution with a concentration of 3wt%, weigh 2.76g (0.04mol) NaNO 2 Dissolve in 20ml of deionized water, add 5ml dropwise to the sulfuric acid aqueous solution with a dropping funnel every 30min, add dropwise 4 times, stir rapidly at room temperature, and remove the generated gas (NO 2 ) into the methyl oleate solution at a flow rate of 2.5ml / min, and after continuous nitration reaction for 4 hours, nitrogen gas was continuously introduced for 30 minutes to remove NO in the solution 2 gas. The reaction product was distilled under reduced pressure, dissolved in chloroform, and separated by thin layer chromatography (Merck's silica gel preparation plate PLCSilicagel60F254, the developing solvent was n-hexane:chloroform:ethyl acetate=60:13:4) to obtain nitro oil Acid methyl est...

Embodiment 2

[0037] Weigh 0.564 g (0.002 mol) of purified oleic acid and dissolve it in 20 ml of n-hexane dewatered by molecular sieves to obtain an oleic acid solution. Prepare 160ml of sulfuric acid aqueous solution with a concentration of 3wt%, weigh 2.76g (0.04mol) NaNO 2 Dissolve in 20ml of deionized water, add 5ml dropwise to the sulfuric acid aqueous solution with a dropping funnel every 30min, add dropwise 4 times, stir rapidly at room temperature, and remove the generated gas (NO 2 ) into the oleic acid solution at a flow rate of 2.5ml / min. After continuous nitration reaction for 4 hours, nitrogen gas was continuously passed for 30 minutes to remove NO in the solution. 2 gas. The reaction product was distilled under reduced pressure, dissolved in chloroform, and separated by thin-layer chromatography (Merck's silica gel preparation plate PLCSilicagel60F254, the developing solvent was n-hexane:ethyl acetate:acetic acid=60:4:3) to obtain nitro oil The acid product is 0.078g with a...

Embodiment 3

[0040] All the reaction raw materials and operating methods used are the same as in Example 1, except that the nitration reaction time is 12 hours, and the nitromethyl oleate product is prepared.

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Abstract

The invention discloses a method for preparing a nitro-oleic acid and derivatives thereof and belongs to the field of organic synthesis. The method for preparing the nitro-oleic acid and derivatives thereof take oleic acid or methyl oleate as a raw material and comprises the following steps: introducing a gas containing nitric oxide (NO) into the raw material, mixing with oxygen, and carrying out one-step synthesis to obtain nitro-oleic acid or nitro methyl oleate, wherein synthesis yield is 10-25%; and further separating by adopting thin-layer chromatography, wherein purity of the obtained final product is higher than 90%. The method for preparing the nitro-oleic acid and derivatives thereof is simple and practicable and high in yield and does not adopt highly toxic chemical reagents of mercuric chloride (HgCl2), phenyl selenium bromide and the like in the traditional synthesis method, so that the method for preparing the nitro-oleic acid and derivatives thereof is an environment-friendly macro preparation method. The method for preparing the nitro-oleic acid and derivatives thereof can provide study on experimental and theoretical basis for popularization and development on nitro fatty acid and derivatives thereof, and application of the nitro fatty acid in the biological field is further expanded.

Description

technical field [0001] The invention relates to a preparation method of nitrooleic acid and derivatives thereof, in particular to a preparation method of nitrooleic acid or methyl nitrooleate, belonging to the field of organic synthesis. Background technique [0002] Since 1986, scientists have discovered through experiments that nitric oxide (NO), a highly active and toxic molecule, can relax human blood vessels and have a magical effect on cardiovascular and cerebrovascular diseases. It has become a molecule that transmits information and instructions to cells. Facts, in one fell swoop established the status of NO in modern medicine, created a new concept that the human body can use gas molecules to transmit information between cells. NO plays an important role in the immune mechanism of the human body. By inducing the operation of synthetase, when inflammation occurs, the immune system will activate phagocytes to produce nitric oxide free radicals ( · NO), relying on the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C205/50C07C201/08
Inventor 费旭吴文忠
Owner INNOBIO CORP LTD