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Preparation of azelaic acid by catalytic oxidizing system

A technology of catalytic oxidation and azelaic acid, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylates, etc., can solve the problems of low product purity, complicated post-processing, low yield, etc., and achieve clean process. , environment-friendly, and the effect of simple reaction process

Inactive Publication Date: 2005-10-12
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] The selectivity of the nitric acid oxidation reaction is not high, and the equipment is severely corroded
The oxidized oleic acid method using potassium permanganate as an oxidant has a low yield and consumes a large amount of sulfuric acid and potassium permanganate, which not only has high cost but also causes serious pollution
Although the technology of potassium permanganate method can be improved by emulsification method, the consumption of potassium permanganate is still very large, and the post-treatment is very complicated, which is not economically desirable.
Using chromic acid as an oxidant is expensive, and it is easy to degrade the oxidation product to produce a low-carbon chain dibasic acid, and the resulting product is not high in purity
It can be seen that in many existing technologies, some methods pollute the environment, some methods have more complicated steps, some methods need to support noble metal catalysts, and need to pass oxygen for a long time, which is time-consuming and costly.
Some methods require high pressure, harsh implementation conditions, high cost, and difficult to scale production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of 9,10-dihydroxystearic acid

[0040] Stir and mix oleic acid (73%), tungstic acid, and isopropanol in a mass ratio of 1:0.0075:2. When the temperature rises to 55° C., add dropwise 50% hydrogen peroxide solution of 0.3 times the amount of oleic acid. The dropwise addition was completed within 20 minutes, and the temperature was raised to 60°C. After 30 minutes of reaction, the isopropanol was recovered by rotary evaporation, and recrystallized with ethyl acetate to obtain 9,10-dihydroxystearic acid;

[0041] Synthesis of Azelaic Acid

[0042] Add catalytic oxidation system solution oleic acid, peracetic acid, hydrogen peroxide, acetic acid, water and concentrated sulfuric acid to the prepared 9,10-dihydroxystearic acid oil phase, the mass ratio is 1:0.5:0.5:2: 2:0.1, react at a temperature of 100°C for 1 hour, remove the solvent by rotary evaporation after the reaction, extract with hot water for 6 times, cool in the refrigerator overnight, produce crysta...

Embodiment 2

[0044] Preparation of 9,10-dihydroxystearic acid

[0045] Stir and mix oleic acid (73%), tungstic acid, and isopropanol in a mass ratio of 1:0.0075:2. When the temperature rises to 65°C, add dropwise 50% hydrogen peroxide solution of 0.3 times the amount of oleic acid. The dropwise addition was completed within 20 minutes, and the temperature was raised to 70°C. After 60 minutes of reaction, the isopropanol was recovered by rotary evaporation, and recrystallized with ethyl acetate to obtain 9,10-dihydroxystearic acid;

[0046] Synthesis of Azelaic Acid

[0047] Add catalytic oxidation system solution oleic acid, peracetic acid, hydrogen peroxide, acetic acid, water and concentrated sulfuric acid to the prepared 9,10-dihydroxystearic acid oil phase, the mass ratio is 1:3:3:5: 5.5:1 reacted at a temperature of 100°C for 4 hours. After the reaction was completed, the solvent was removed by rotary evaporation, extracted with hot water for 6 times, cooled in the refrigerator overn...

Embodiment 3

[0049] Preparation of 9,10-dihydroxystearic acid

[0050] Stir and mix oleic acid (73%), tungstic acid, and isopropanol in a mass ratio of 1:0.0075:2. When the temperature rises to 60°C, add dropwise 50% hydrogen peroxide solution of 0.3 times the amount of oleic acid. The dropwise addition was completed within 20 minutes, and the temperature was raised to 65°C. After 45 minutes of reaction, the isopropanol was recovered by rotary evaporation, and recrystallized with ethyl acetate to obtain 9,10-dihydroxystearic acid;

[0051] (2) Synthesis of azelaic acid

[0052] Add catalytic oxidation system solution oleic acid, peracetic acid, hydrogen peroxide, acetic acid, water and concentrated sulfuric acid to the prepared 9,10-dihydroxystearic acid oil phase, the mass ratio is 1:2.5:0.5:4: 2.8:0.2, react at a temperature of 100°C for 3 hours, remove the solvent by rotary evaporation after the reaction, extract with hot water for 6 times, put in the refrigerator to cool overnight, pr...

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PUM

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Abstract

Production of anchoic acid by catalytic oxidizing system is carried out by agitating and mixing oleic acid, tungstic acid with solvent, raising temperature, dripping adding hydrogen solution, raising temperature, rotary evaporating and recovering solvent, re-crystallizing by acetic ether, obtaining 9,10-dioxystearic acid, adding solution of catalytic oxidizing system into oil-phase of 9,10-dioxystearic acid, extracting, filtering, drying, and obtaining anchoic acid from reacting liquid. Its advantages include high productivity, no environmental pollution, simple operation and no pressure.

Description

technical field [0001] The invention relates to a method for preparing azelaic acid by a catalytic oxidation system Background technique [0002] Azelaic acid, also known as azelaic acid, is a white to yellowish monoclinic prism, needle-like crystal or powder. Molecular formula C 9 h 16 o 4 , molecular weight 188.22, specific gravity 1.0291 (4°C), 1.225 (25°C), melting point 106.5°C, boiling point 286.5°C (13.33kPa), refractive index 1.4303 (111°C), medium-length carbon chain plus two carboxyl groups, giving Azelaic acid has a wide range of uses and is an important intermediate in organic synthesis. [0003] Azelaic acid can be used to synthesize dioctyl azelate (DOZ) plasticizer, synthetic perfume, lubricating oil and polyamide and other products. Dioctyl azelate, didecyl azelate, and tridecyl azelate are good lubricants. Azelaic acid is also used in the production of nylon 69 and nylon 9. Azelaic acid is aminated and hydrogenated to produce...

Claims

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Application Information

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IPC IPC(8): C07C51/285C07C55/18
Inventor 吾满江·艾力高军军张亚刚孙自才胡书明樊莉董昕
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI