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Method for preparing high-carbon dibasic acid ester from unsaturated fatty acid ester

A technology of fatty acid esters and dibasic esters, which is applied in the field of preparing high-carbon dibasic esters, can solve the problems of non-renewability, and achieve the effect of industrial production, simple steps, and mild conditions

Inactive Publication Date: 2020-02-21
SHIHEZI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials (methanol and mixed dibasic acid) in the traditional synthesis method belong to petrochemical energy and are not renewable

Method used

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  • Method for preparing high-carbon dibasic acid ester from unsaturated fatty acid ester
  • Method for preparing high-carbon dibasic acid ester from unsaturated fatty acid ester
  • Method for preparing high-carbon dibasic acid ester from unsaturated fatty acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Mix 0.3 mmol of methyl linoleate, the second-generation Hoveyda-Grubbs catalyst (1.0% in mole percentage of methyl linoleate) and 2 mL of toluene solvent, heat up to 45° C., and then react for 6 hours. After the completion of the reaction, through gas chromatography detection, the yield of 1,4-cyclohexadiene was 84%, and the yield of high-carbon dibasic ester was 81%; the high-carbon dibasic acid ester was obtained by separation by column chromatography. Yield: 62%.

Embodiment 2

[0066] Mix 0.3 mmol of methyl linoleate, the second-generation Hoveyda-Grubbs catalyst (1.0% by mole of methyl linoleate) and 2 mL of toluene solvent, heat up to 35° C., and then react for 6 hours. After the completion of the reaction, through gas chromatography detection, the yield of 1,4-cyclohexadiene was 80%, and the yield of high carbon dibasic ester was 80%.

Embodiment 3

[0068] Mix 0.5 mmol of methyl linoleate with the second-generation Hoveyda-Grubbs catalyst (1.0% in mole percentage of methyl linoleate), heat up to 35° C. without solvent, and then react for 6 hours. After the completion of the reaction, the gas chromatography detection showed that the yield of 1,4-cyclohexadiene was 70%, and the yield of high carbon dibasic ester was 71%.

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Abstract

The invention provides a method for preparing high-carbon dibasic acid ester from unsaturated fatty acid ester, belonging to the technical field of organic synthesis. The preparation method comprisesthe following steps: mixing unsaturated fatty acid ester with a catalyst, and carrying out an olefin metathesis reaction to obtain the high-carbon dibasic acid ester. Vegetable oil is rich in unsaturated fatty acids such as oleic acid, linoleic acid, linolenic acid and ricinoleic acid and undergoes an esterification reaction to obtain the high-carbon dibasic acid ester. According to the invention,the high-carbon dibasic acid ester can be prepared by utilizing the metathesis reaction of the unsaturated fatty acid ester; the defect that the high-carbon dibasic acid ester is prepared by adoptingpetrochemical resources in the prior art is overcome; and the vegetable oil is wide in distribution, low in price, easy to obtain and renewable; so the method has good application prospects. When theunsaturated fatty acid ester contains more than two double bonds, 1,4-cyclohexadiene can be obtained by using the method, and the 1,4-cyclohexadiene is also a common organic intermediate.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing high-carbon dibasic esters by utilizing unsaturated fatty acid esters. Background technique [0002] High-carbon dibasic ester is an organic intermediate and an excellent green solvent, which is widely used in the coating industry. In industry, it is usually obtained by reacting methanol with mixed dibasic acid. The raw materials (methanol and mixed dibasic acid) in the traditional synthesis method belong to petrochemical energy and are not renewable. Therefore, there is a need to provide a method for preparing high carbon dibasic esters using renewable resources. SUMMARY OF THE INVENTION [0003] The object of the present invention is to provide a kind of method that utilizes unsaturated fatty acid ester to prepare high carbon dibasic acid ester, utilizes unsaturated fatty acid ester derived from vegetable oil as raw material, obtains high ca...

Claims

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Application Information

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IPC IPC(8): C07C67/475C07C69/593C07C1/20C07C13/23
CPCC07C1/20C07C67/475C07C2601/16C07C69/593C07C13/23
Inventor 刘宁代斌张魁魁刘振邦
Owner SHIHEZI UNIVERSITY
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