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Green synthetic method of epoxy unsaturated fatty acid methyl ester and catalyst

A fatty acid methyl ester, green synthesis technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, etc., can solve the unsatisfactory hydrophobicity and water resistance of rhenium ionic liquids , The catalytic effect is not very ideal, the double bond structure is complicated, etc., to achieve good catalytic oxidation effect, reduce the difficulty of post-processing, and strong hydrophobic effect

Inactive Publication Date: 2015-02-04
浙江嘉澳环保科技股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, compared with cyclohexene, on the one hand, long-chain mixed unsaturated fatty acid methyl esters contain ester groups, and their water solubility is quite different from that of cyclohexene; on the other hand, the double bond structure in long-chain unsaturated fatty acid methyl esters is more complicated. When adopting above-mentioned ionic liquid and oxidizing agent to carry out epoxidation reaction, catalytic effect is not very ideal, and reaction speed is slower, and the epoxy value of the product obtained is lower
When directly adopting long-chain unsaturated fatty acid methyl ester epoxidation oxidant hydrogen peroxide commonly used, because hydrogen peroxide generally exists in the form of aqueous solution, the hydrophobicity and water resistance of the rhenium ionic liquid in the above-mentioned literature are not ideal, leading to the reaction result poor

Method used

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  • Green synthetic method of epoxy unsaturated fatty acid methyl ester and catalyst
  • Green synthetic method of epoxy unsaturated fatty acid methyl ester and catalyst
  • Green synthetic method of epoxy unsaturated fatty acid methyl ester and catalyst

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preparation example Construction

[0035] The preparation method of above-mentioned hydrophobic rhenium ionic liquid catalyst is:

[0036] Add N-methylimidazole (1mmol) and bromododecane (1.5mmol) respectively into a round bottom flask with a reflux condenser, and stir at 125-135°C for 5 hours to obtain a pale yellow viscous liquid, which is washed with ether for 3 Once, overnight at 40~50°C / 100~133Pa, a light brown waxy solid was obtained, i.e. 1-dodecyl-3-methylimidazolium bromide; 1-dodecyl-3-methylimidazolium Dissolve the bromide salt in hot distilled water, stir quickly, slowly add ammonium perrhenate aqueous solution (20ml, 0.1mol / L) dropwise, stir vigorously at 80-90°C for 6 hours, let stand, pour off the upper aqueous phase, and wash the lower layer with water The ionic liquid is neutralized, the moisture is removed in vacuum, and the vacuum is dried overnight at 60-70°C / 100-133Pa to obtain a yellow viscous liquid, that is, an alkylimidazolium-rhenium ionic liquid.

Embodiment 1

[0038] Put 500 g of unsaturated fatty acid methyl esters with an iodine value of 55% in a three-necked flask, heat to 60°C, add 1g of hydrophobic rhenium ionic liquid catalyst, add dropwise 88.35g of hydrogen peroxide with a concentration of 50%, and react at 60°C for 3 hours, Leave to stand for stratification, vacuum remove a small amount of remaining moisture in the upper oil layer, and obtain the target product epoxy fatty acid methyl ester, the epoxy value is 2.65%, and the iodine value is 5.6%. Formic acid method epoxy unsaturated fatty acid methyl ester with the same iodine value obtains epoxy fatty acid methyl ester with an epoxy value of 2.62% and an iodine value of 5.1%. The lower layer is a mixture of ionic liquid and hydrogen peroxide. The concentration of hydrogen peroxide is about 12%. After removing part of the water under reduced pressure at low temperature, the concentration of hydrogen peroxide is increased to about 30%, which is directly used for the next reac...

Embodiment 2

[0040]Place 500 g of unsaturated fatty acid methyl esters with an iodine value of 90% in a three-necked flask, heat to 50°C, add 2.5g of hydrophobic rhenium ionic liquid catalyst, add dropwise 132.52g of hydrogen peroxide with a concentration of 50%, and react at 62°C for 2 hours , leave to stand for stratification, and the upper oil layer vacuum removes a small amount of remaining moisture to obtain the target product epoxy fatty acid methyl ester, the epoxy value is 3.49%, and the iodine value is 6.0%. Formic acid method epoxy unsaturated fatty acid methyl ester with the same iodine value obtains epoxy fatty acid methyl ester epoxy value of 3.37%, iodine value of 5.7%. The lower layer is a mixture of ionic liquid and hydrogen peroxide. The concentration of hydrogen peroxide is about 14%. After removing part of the water under reduced pressure at low temperature, the concentration of hydrogen peroxide is increased to about 30%, which is directly used for the next reaction.

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Abstract

The invention discloses a green synthetic method of epoxy unsaturated fatty acid methyl ester. the method comprises the following steps: under the action of a catalyst and an oxidizing agent, unsaturated fatty acid methyl ester is subjected to an epoxidation reaction at the temperature of 50-70 DEG C; and after the reaction, post-treatment is carried out to obtain epoxy unsaturated fatty acid methyl ester, wherein the catalyst is a hydrophobic rhenium ionic liquid and the oxidizing agent is hydrogen peroxide. The invention also discloses a hydrophobic rhenium ionic liquid catalyst. In comparison with a traditional formic acid epoxidation method, the preparation method provided by the invention has advantages as follows: a corrosive liquid will not be generated during the whole process, and equipment will not be corroded; and meanwhile, generation of a lot of wastewater and exhaust gas is avoided after the reaction, environmental pollution is reduced, and green catalysis is realized.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a green synthesis method and catalyst of epoxy unsaturated fatty acid methyl ester. Background technique [0002] Epoxy fatty acid methyl ester is a new type of environment-friendly polyvinyl chloride plasticizer. It has high plasticizing efficiency, good compatibility, good thermal stability, and excellent low-temperature performance of the product. It can completely or partially replace the o-phthalic plasticizer DOP , Widely used in PVC products such as food packaging film, medical supplies materials, toys and so on. At the same time, it can also be used as a non-toxic plasticizer and softener for cellulose resin and synthetic rubber. [0003] At present, the production of epoxy fatty acid methyl ester adopts a solvent-free method, with formic acid or acetic acid under the action of concentrated sulfuric acid, hydrogen peroxide as an oxidant and an epoxidat...

Claims

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Application Information

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IPC IPC(8): C07D301/12C07D303/42B01J31/02
CPCC07D301/12B01J31/0284B01J2231/72C07D303/42
Inventor 沈健傅俊红
Owner 浙江嘉澳环保科技股份有限公司
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