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Method for preparing 9,10-dihydroxystearic acid and its methyl by hydrogen dioxide oxidation process

A technology of dihydroxystearic acid and hydrogen peroxide, which is applied in the field of preparation 9, can solve the problems of no separation and purification, and achieve the effects of environmental friendliness, greening, and cost reduction

Inactive Publication Date: 2008-05-14
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

[0009] Song Heyuan from Lanhua Institute of Chinese Academy of Sciences obtained dihydroxystearic acid by using 50% hydrogen peroxide as oxidant and tungsten compound as catalyst during the synthesis of azelaic acid, but did not separate and purify it.

Method used

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  • Method for preparing 9,10-dihydroxystearic acid and its methyl by hydrogen dioxide oxidation process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] With 50g oleic acid (mass percentage is 75%, molar ratio is 0.1329mol), the mixture of 25g (0.5435mol) formic acid is placed in three-necked reaction flask, is that 20% hydrogen peroxide 50ml is added dropwise at room temperature, is warming up to 30 ℃ oxidation;

[0035] React 2 hours after hydrogen peroxide is added dropwise;

[0036] Carry out underpressure distillation recovery solvent after reaction finishes, and reaction mixture adopts organic solvent ethyl acetate recrystallization;

[0037] After drying the crystallized product, a 9,10-dihydroxystearic acid product with a yield of 90% and a purity of 92.6% can be obtained;

[0038] The acid value of the obtained 9,10-dihydroxystearic acid product is 185, the iodine value is 0, and the melting point is 89-93°C;

[0039] Add the 7g calcium oxide of raw material weight in the remaining formic acid aqueous solution after reaction, obtain product calcium formate reclaiming through routine method;

[0040] Add 3 ti...

Embodiment 2

[0042] A mixture of 53g oleic acid (75% by mass, 0.1409mol molar ratio) and 50g (1.087mol) formic acid was placed in a three-necked reaction flask, 80ml of 25% hydrogen peroxide was added dropwise at room temperature, and the temperature was raised to 40°C for oxidation ;

[0043] After the hydrogen peroxide has been added dropwise, react for 4 hours;

[0044] After the reaction is finished, the solvent is recovered by distillation under reduced pressure, and the reaction mixture is recrystallized with the organic solvent diethyl ether;

[0045] The 9,10-dihydroxystearic acid product with a yield of 94% and a purity of 93.6% can be obtained after drying the crystallized product;

[0046] The acid value of the obtained 9,10-dihydroxystearic acid product is 173, the iodine value is 0, and the melting point is 90-94°C;

[0047] Add the 10g calcium carbonate of raw material weight in the formic acid aqueous solution that remains after reaction, obtain product calcium formate recov...

Embodiment 3

[0050] With 55g oleic acid (mass percentage is 75%, molar ratio is 0.1463mol), the mixture of 110g (2.3914mol) formic acid is placed in three-necked reaction flask, and concentration is 30% hydrogen peroxide 100m at room temperature, is warming up to 45 ℃l oxidation;

[0051] React 5 hours after hydrogen peroxide has been added dropwise;

[0052] After the reaction is finished, the solvent is recovered by distillation under reduced pressure, and the reaction mixture is recrystallized from ethyl acetoacetate;

[0053] The 9,10-dihydroxystearic acid product with a yield of 94% and a purity of 95% can be obtained after drying the crystallized product;

[0054] The acid value of the obtained 9,10-dihydroxystearic acid product is 171, the iodine value is 0, and the melting point is 94-96°C;

[0055] Add the 10g calcium oxide of raw material weight in the formic acid aqueous solution that remains after reaction, obtain product calcium formate reclaim through routine method;

[00...

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Abstract

The invention relates to a preparation method for 9, 10-dihydroxy stearic acid and methyl ester, which is characterized in that the oleic acid and the formic acid are mixed uniformly in room temperature; the mixture is added with hydrogen peroxide, and warmed up and separated from water phase; the solvent is recycled through decompression and distillation; the generative reaction admixture is recrystallized with organic solvent, so that the product 9, 10-dihydroxy stearic acid is prepared. The recovered formic acid solution can generate ice-cream calcium formate salt separation by adding calcium oxide and calcium carbonate; subsequently the methyl alcohol and oil of vitriol is arranged into the product 9, 10-dihydroxy stearic acid for a reflux reaction, and then is rotated and vaporized out the water phase and oil phase for being washed to be neutral, thereby the 9, 10-dihydroxy stearic acid methyl ester product is generated through dehydration. The invention has the advantages of clean process, safe implementation, easy operation, full utilization of the reactant, reduced waste emission, effective utilization of the low-concentration hydrogen peroxide, and favorableness to large-scale production.

Description

technical field [0001] The invention relates to a method for preparing 9,10-dihydroxystearic acid and its methyl ester by using a hydrogen peroxide oxidation method. Background technique [0002] 9,10-dihydroxystearic acid is a very important chemical intermediate, it is a white waxy or powdery solid, the molecular weight is 316, the melting point is 92°C-96°C, it is insoluble in water and ethyl acetate, and easily soluble In methanol, ethanol, ether and other solvents. It is further oxidized and cracked to generate azelaic acid and corresponding useful chemical products. At the same time, 9,10-dihydroxystearic acid and its derivatives can be used in medicine, feed additives, flavors and fragrances, and daily chemical industries. Its structure diagram is as follows: [0003] [0004] Michael A. Oakley et al. used tungstic acid as a catalyst to oxidize 60% hydrogen peroxide to obtain 9,10-dihydroxystearic acid, but it was not analyzed as a separate ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/105C07C69/675C07C51/367C07C67/08
Inventor 吾满江·艾力阿依夏木古丽·努尔艾买提夏木西卡马尔·买买提哈丽丹·买买提
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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