A method of co-producing capacitor grade 2-butyl sebacic acid and 2,9-dibutyl sebacic acid

A technology of butyl sebacic acid and diethoxycarbonyl diethyl sebacate, applied in chemical instruments and methods, carboxylate preparation, carboxylate preparation and other directions, can solve problems such as low oxidation efficiency of electrolyte , to achieve the effect of excellent electrochemical performance, simple synthesis method and high product purity

Active Publication Date: 2016-03-09
JIANGSU GUOTAI SUPER POWER NEW MATERIALS
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

Due to the existence of by-products, the application in the electrolyte will lead to low oxidation efficiency of the electrolyte

Method used

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  • A method of co-producing capacitor grade 2-butyl sebacic acid and 2,9-dibutyl sebacic acid
  • A method of co-producing capacitor grade 2-butyl sebacic acid and 2,9-dibutyl sebacic acid
  • A method of co-producing capacitor grade 2-butyl sebacic acid and 2,9-dibutyl sebacic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Step 1: Add 1922.4 g (12.0 mol) of diethyl malonate and 1,463.8 g (6.0 mol) of 1,6-dibromohexane into a 10L three-necked flask, and dropwise add 4489.3 g of sodium ethoxide ethanol solution with a mass concentration of 20% g (of which 13.2 mol of sodium ethoxide), stirred under reflux for 8 hours after the dropwise addition, cooled to room temperature, and filtered to obtain ethyl 9,9-bis(methoxycarbonyl)-undecanecarboxylate (C) ethanol Solution 6803.3g.

[0029] Step 2: Distill the above solution, collect the fraction with a top temperature of 165~200°C (3mmHg) to obtain 2,9-bis(ethoxycarbonyl)-diethyl sebacate 2200.0g, step 1 and 2 The total yield was 91.1%, and the purity was 98.9% by gas phase detection.

[0030] Step 3: Add 2,9-bis(ethoxycarbonyl)-diethyl sebacate 2000g (4.97mol) and n-bromobutane 1498.2g (10.9mol) into a 10L three-necked flask, and the mass concentration of the drops is 3707.1g of 20% sodium ethoxide ethanol solution (including 10.9mol of sodium...

Embodiment 2

[0036] Step 1: Add 2403.0 g (15.0 mol) of diethyl malonate and 1463.7 g (6.0 mol) of 1,6-dibromohexane into a 10L three-necked flask, and dropwise add 4489.4 g of sodium ethoxide ethanol solution with a mass concentration of 20% g (13.2mol), stirred under reflux for 8 hours after the dropwise addition, cooled to room temperature, and filtered to obtain 6860.1g of 9,9-bis(methoxycarbonyl)-undecanoic acid ethyl ester (C) ethanol solution .

[0037] Step 2: Distill the above solution, collect the fraction with a top temperature of 165~200°C (3mmHg), and obtain 2,9-bis(ethoxycarbonyl)-diethyl sebacate 2213.1g, step 1 and 2 The total yield was 91.6%, and the purity was 98.2% by gas phase detection.

[0038] Step 3: Add 2,9-bis(ethoxycarbonyl)-diethyl sebacate 2000g (4.97mol) and n-bromobutane 1498.1g (10.9mol) into a 10L three-necked flask. 20% sodium ethoxide ethanol solution 3707.2g (10.9mol), stirred under reflux for 8 hours after the dropwise addition, cooled to room temperat...

Embodiment 3

[0044] Step one, step two: with embodiment 1

[0045] Step 3: Add 2000g (4.97mol) of 2,9-bis(ethoxycarbonyl)-diethyl sebacate and 1498.3g (10.9mol) of n-bromobutane into a 20L three-necked flask. 7739.0g (10.9mol) of 20% potassium carbonate ethanol solution, stirred under reflux for 8 hours after the dropwise addition, cooled to room temperature, and filtered to obtain 2-butyl-2,9-diethoxycarbonyl sebacic acid di 5483.5 g of ethyl ester and diethyl 2,9-dibutyl-2,9-diethoxycarbonyl sebacate in ethanol.

[0046] Step 4: Distill the above solution, collect the fraction with a top temperature of 170~180°C (3mmHg), and obtain 454.0g of 2-butyl-2,9-diethoxycarbonyl sebacate (ester 1) , the total yield of the two-step ester 1 in steps 3 and 4 was 19.9%, and the fraction with a top temperature of 200~206°C (3mmHg) was collected to obtain 2,9-dibutyl-2,9-diethoxycarbonyldecanedi Acid diethyl ester (ester 2) was 1850.1g, and the total yield of ester 2 in steps 3 and 4 was 72.3%.

[0...

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Abstract

The invention relates to a co-production capacitor stage 2- Butyl sebacic acid and 2,9- The method of dibutyl sebacic acid to diethyl malonate and 1,6- Dibromohexane is used as a raw material, and it is obtained by nucleophilic substitution reaction in a strong alkali solution 2,9- Bis(ethoxycarbonyl) - Diethyl sebacate, then reacted with n-butane bromide in a strong alkali solution, and then obtained by rectification 2- Butyl -2,9- Diethyl diethoxycarbonyl sebacate and 2,9- Dibutyl -2,9- Diethoxycarbonyl sebacate diethyl ester; obtained through saponification, acid precipitation and decarboxylation respectively 2- Butyl sebacic acid and 2,9- Dibutyl sebacic acid. The present invention avoids by-products by improving the technological process 2- Butyl -8- production of ethoxycaprylic acid, and, high-purity 2- Butyl sebacic acid has a higher 2- Butyl suberic acid has more excellent electrochemical properties, thereby improving the oxidation efficiency of the electrolyte, and has a good market prospect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for co-producing capacitor-grade 2-butyl sebacic acid and 2,9-dibutyl sebacic acid. Background technique [0002] In order to meet the requirements of long-life aluminum electrolytic capacitors such as automotive electronics, the electrolyte of the branched chain dibasic acid series has gradually become a new favorite in the market, especially the dibasic acid with a branched chain at the α position can inhibit the esterification reaction between the acid and the solvent ethylene glycol. It plays an extremely important role in the working electrolyte of high-voltage aluminum electrolytic capacitors. At present, there are more branched dibasic acids used in the market as follows: Ⅰ) 2-methyl azelaic acid; Ⅱ) 8-vinyl-10-octadecanedioic acid; Ⅲ) single α-position substituted branched chain dibasic acid (CN101805255A, 2010-8-18); Ⅳ) 2,9-dibutyl sebacic acid, et...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C55/02C07C51/38
CPCC07C51/09C07C51/38C07C51/412C07C67/343C07C67/54C07C55/02C07C69/34
Inventor 闻立新施苏萍何永刚邹凯熊鲲严向军郭军关士友李建中
Owner JIANGSU GUOTAI SUPER POWER NEW MATERIALS
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