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Dimethyl sebacate electrochemical synthesis method

A technology for the synthesis of dimethyl sebacate, which is applied in the direction of electrolysis process, electrolysis components, electrolysis organic production, etc., and can solve the problems of reaction selectivity and low current efficiency of the preparation method

Active Publication Date: 2021-09-21
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, the applicant has found that the dimethyl sebacate prepared by the existing electrochemical method will produce a large amount of by-products, such as methyl pentenoate, and the production of dimethyl sebacate will by-produce pentenoic acid per ton. Methyl ester 0.15 tons of methyl pentenoate, resulting in very low reaction selectivity and current efficiency of the electrochemical method preparation method, there is no effective means to solve this problem at present

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] A kind of electrochemical synthesis method of dimethyl sebacate, the steps are:

[0054] 1) Get 80g (0.5mol) monomethyl adipate, 160g benzene and 5.25g (0.075mol) potassium methylate and mix them uniformly and then transfer them to the electrolytic cell, wherein the mass ratio of the raw material monomethyl adipate to the organic solvent benzene The ratio is 0.5:1, and the addition amount of the electrolyte potassium methoxide is 15% of the molar amount of the raw material monomethyl adipate in terms of moles. The anode of the electrolytic cell uses a platinum-titanium electrode, and the cathode uses a nickel cathode. Using CO 2 After the gas replaces the air in the electrolytic cell 5 times, fill the electrolytic cell with CO 2 to 0.5MPa, then raise the temperature of the electrolytic cell to 60°C, and start the electrolytic reaction. The current density of the electrolytic cell is 1200A / m 2 , Electrolysis potential 2V.

[0055] 2) Mix 1.48g of 37wt% (0.015mol in t...

Embodiment 2

[0059] 1) Get 87g (0.5mol) dimethyl adipate, 145g pyridine and 5.4g (0.01mol) sodium methoxide and mix them uniformly and then transfer them to the electrolytic cell, wherein the mass ratio of the raw material dimethyl adipate to the organic solvent pyridine The ratio is 0.6:1, and the added amount of the electrolyte sodium methoxide is 20% of the molar amount of the raw material dimethyl adipate on a molar basis. The anode of the electrolytic cell uses Ti-based IrO 2 The anode and the cathode are nickel cathodes. Using CO 2 After the gas replaces the air in the electrolytic cell 5 times, fill the electrolytic cell with CO 2 to 0.8MPa, then raise the temperature of the electrolytic cell to 65°C, and start the electrolytic reaction. The current density of the electrolytic cell is 1400A / m 2 , Electrolysis potential 2.2V.

[0060] 2) Mix 2.56g of 25wt% (0.018mol in terms of HCl) hydrochloric acid with 0.683g (0.0087mol) of sodium peroxide, wherein the amount of hydrochloric a...

Embodiment 3

[0064] 1) Get 73g (0.5mol) of adipic acid, 91.25g of acetonitrile and 6.16g (0.01mol) of potassium hydroxide and mix them uniformly and transfer them to the electrolytic cell, wherein the mass ratio of the raw material adipic acid to the organic solvent acetonitrile is 0.8:1 , the amount of electrolyte potassium hydroxide added in moles is 22% of the molar amount of adipic acid as the raw material. The anode of the electrolytic cell uses Ti-based PbO 2 The anode and the cathode are nickel cathodes. Using CO 2 After the gas replaces the air in the electrolytic cell 5 times, fill the electrolytic cell with CO 2 to 1.0MPa, then raise the temperature of the electrolytic cell to 70°C to start the electrolytic reaction, and the current density of the electrolytic cell is 1500A / m 2 , Electrolysis potential 2.4V.

[0065] 2) 4.91g33wt% (0.02mol in terms of HBr) hydrobromic acid is mixed with 1.76g (0.016mol) potassium peroxide, wherein the hydrobromic acid consumption is 4.0% of t...

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Abstract

The invention discloses a dimethyl sebacate electrochemical synthesis method, which comprises: 1) mixing adipic acid and an ester compound thereof, an organic solvent and an electrolyte, placing in an electrolytic tank, introducing a carbon dioxide gas into the electrolytic tank to make the system pressure reach 0.5-4 Mpa (gauge pressure), heating the electrolytic tank to a temperature of 60-80 DEG C, and starting an electrolytic reaction; and 2) adding a mixture of haloid acid and peroxide into the electrolytic reaction system in the step 1), and obtaining the dimethyl sebacate after the electrolytic reaction is finished. According to the method, the generation of a byproduct methyl pentenoate can be remarkably reduced, and the selectivity of dimethyl sebacate is improved.

Description

technical field [0001] The invention belongs to the field of organic electrochemical synthesis and relates to an electrochemical synthesis method of dimethyl sebacate. Background technique [0002] Sebacic acid is an important raw material for the synthesis of polymer materials and organic synthesis. The published patent CN101318892A describes a method for preparing sebacic acid from castor oil compounds. Sebacic acid is prepared by alkaline cracking of ricinoleic acid under high pressure and high temperature; Sesame oil prices fluctuate greatly. In order to prepare sebacic acid cheaply, researchers are actively looking for new raw materials and synthetic methods. [0003] Among them, using adipic acid as a raw material to esterify adipate compounds, and then through Brown-Walker electrolytic decarboxylation coupling to synthesize sebacic acid ester compounds, and then hydrolyzing into sebacic acid is an effective way, which has the advantages of simple product separation....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/07
CPCC25B3/07
Inventor 栾谨鑫杜旺明钱向阳张永振
Owner WANHUA CHEM GRP CO LTD
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