Method for epoxidating methyl oleate

A methyl oleate, epoxidation technology, applied in chemical instruments and methods, organic chemistry, chemical/physical processes, etc., can solve the problems of unstable organic peroxy acid, easy explosion, environmental pollution, etc., and achieve conversion rate. and high selectivity, mild reaction conditions, and short reaction times

Inactive Publication Date: 2010-12-29
CHINA RES INST OF DAILY CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process has many disadvantages: ①The organic peroxyacid is unstable and easy to explode; ②The residual organic acid and organic peroxyacid must be washed away with a large amount of water, which is difficult to post-process; ③Ring-opening reaction is prone to occur; ④Unreacted materials are difficult to reuse ; ⑤ serious environmental pollution
But the research that heteropolyacid quaternary ammonium salt is applied to the epoxidation reaction of methyl oleate, there is no report at present

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1, 5.00g phosphotungstic heteropolyacid (H 3 o 40 PW 12 ) and 3.05g dioctadecyldimethylammonium chloride ((C 18 h 37 ) 2 N(CH 3 ) 2 Cl) were respectively dissolved in water (the molar ratio was 1:3), and then the aqueous solution of heteropolyacid was slowly added dropwise to the aqueous solution of dioctadecyldimethylammonium chloride at room temperature, and stirred at room temperature for 4 hours. The cloudy solution after the reaction was vacuum filtered, the filter cake was washed 3 times with water, then washed 3 times with ether, and dried in vacuum for 20 hours to obtain [(C 18 h 37 ) 2 N(CH 3 ) 2 ] 3 ·PW 12 o 40 (referred to as phosphotungstic acid-1821).

[0025] 20g methyl oleate (iodine value 80g / 100g, the same below) was added to the reactor (four-neck flask with agitator, reflux condenser, thermometer and dropping funnel, the same below), and 0.5g phosphorus Tungstic acid-1821 and 70g tetrahydrofuran, heated to 70°C and kept the t...

Embodiment 2

[0026] Embodiment 2, 5.00g phosphomolybdenum heteropolyacid (H 3 o 40 PMo 12 ) and 4.50g dioctadecyl dimethyl ammonium chloride ((C 18 h 37 ) 2 N(CH 3 ) 2 Cl) were respectively dissolved in a small amount of water (the molar ratio was 1:3.5), and then the heteropolyacid aqueous solution was slowly added dropwise to the aqueous solution of dioctadecyldimethylammonium chloride at room temperature, and stirred at room temperature for 5 hours . The cloudy solution after the reaction was vacuum filtered, the filter cake was washed 4 times with water, then 4 times with ether, and dried in vacuum for 25 hours to obtain [(C 18 h 37 ) 2 N(CH 3 ) 2 ] 3 ·PM 12 o 40 (referred to as phosphomolybdic acid-1821).

[0027] 20g methyl oleate is joined in the reactor, add 0.5g phosphomolybdic acid-1821 and 100g chloroform, heat to 70 ℃ and keep this temperature constant, slowly add dropwise 40mL hydrogen peroxide (30wt%), make hydrogen peroxide Finish dripping within 2 hours, and...

Embodiment 3

[0028] Embodiment 3, 5.00g phosphotungstic heteropolyacid (H 3 o 40 PW 12 ) and 3.25g dioctadecyl dimethyl ammonium chloride ((C 18 h 37 ) 2 N(CH 3 ) 2 Cl) were dissolved in water respectively (the molar ratio was 1:3.2), and then the aqueous heteropolyacid solution was slowly added dropwise to the aqueous solution of dioctadecyldimethylammonium chloride at room temperature, and stirred at room temperature for 4.5 hours. The cloudy solution after the reaction was vacuum filtered, the filter cake was washed 3 times with water, then 3 times with ether, and dried in vacuum for 23 hours to obtain [(C 18 h 37 ) 2 N(CH 3 ) 2 ] 3 ·PW 12 o 40 .

[0029]20g of methyl oleate was added to the reactor, 0.5g of phosphotungstic acid-1821 and 60g of 1,2-dichloroethane were added, heated to 70°C and the temperature was kept constant, and 40mL of hydrogen peroxide (30wt %), hydrogen peroxide was dripped within 2.5 hours, and then continued to insulate for 2 hours after the dropw...

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PUM

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Abstract

The invention discloses a method for epoxidating methyl oleate, which comprises the following steps of: adding the methyl oleate into a reactor, adding a catalyst and an organic solvent, heating the mixture to the required reaction temperature of 50 to 70 DEG C, keeping constant the temperature, adding dropwise hydrogen peroxide with the concentration of 30 weight percent according to the mass ratio of the hydrogen peroxide to the methyl oleate of 1-2:1 in a way of ensuring that the dropwise addition of the hydrogen peroxide is finished within 2 to 2.5 hours, and continuing to preserve the heat for 2 to 6 hours after the dropwise addition is finished, wherein the mass ratio of the organic solvent to the methyl oleate is 2.0-5.0:1, and the mass ratio of the catalyst to the methyl oleate is 5-25:1,000; standing the reacted mixed solution in an environment of 5 to 10 DEG C for 3 to 5 hours to slowly separate the catalyst out and filtering the mixed solution to remove the catalyst; and standing and demixing filtrate, and distilling an organic layer under reduced pressure to remove the organic solvent to obtain the product epoxy methyl oleate. The method has the advantages of easy post-treatment, no environmental pollution, and high percent conversion and selectivity.

Description

[0001] Field [0002] The invention relates to a method for epoxidizing methyl oleate. Background technique [0003] Methyl oleate is a very potential substitute for mineral lubricating oil, but methyl oleate contains a large number of double bonds, resulting in poor oxidation stability and it is difficult to meet the performance standards of conventional lubricants. The epoxidation of methyl oleate can greatly reduce its iodine value, and the obtained epoxidized methyl oleate has high oxidation stability and good lubricating performance, and can meet the performance standard of lubricating oil. In addition, epoxidized methyl oleate is a non-toxic plasticizer recognized in the world. It has excellent thermal stability and light stability, and has good plasticizing durability. It is a very important industrial additive. [0004] There are three main methods for epoxidation of double bonds in oils: [0005] 1. Epoxidation method using organic peroxyacid and its derivatives ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/42C07D301/12B01J31/34
Inventor 康保安周喜阳武华萍杨卉艳孙晋源
Owner CHINA RES INST OF DAILY CHEM IND
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