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Co-production method for capacitance-grade 2-butylsebacic acid and 2, 9-butylsebacic 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, improved oxidation efficiency and high yield

Active Publication Date: 2015-03-25
JIANGSU GUOTAI SUPER POWER NEW MATERIALS
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  • Abstract
  • Description
  • Claims
  • 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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  • Co-production method for capacitance-grade 2-butylsebacic acid and 2, 9-butylsebacic acid
  • Co-production method for capacitance-grade 2-butylsebacic acid and 2, 9-butylsebacic acid
  • Co-production method for capacitance-grade 2-butylsebacic acid and 2, 9-butylsebacic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Step 1: Add 1922.4 g (12.0 mol) of diethyl malonate and 1463.8 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: Carry out rectification of the above solution, collect the fraction with a top temperature of 165~200 ℃ (3mmHg), and 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 2000g (4.97 mol) of 2,9-bis(ethoxycarbonyl)-diethyl sebacate and 1498.2g (10.9 mol) of n-bromobutane into a 10L three-necked flask, and the mass concentration of the dropwise addition is 3707.1g of 20% sodium ethoxide...

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 (13.2 mol), stirred under reflux for 8 hours after the dropwise addition, cooled to room temperature, and filtered to obtain 6860.1g ethanol solution of ethyl 9,9-bis(methoxycarbonyl)-undecanecarboxylate (C) .

[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 (4.97 mol) and n-bromobutane 1498.1g (10.9 mol) into a 10L three-necked flask. 20% sodium ethoxide ethanol solution 3707.2g (10.9 mol), after the dropwise addition was completed, stirred under reflux for 8 hours, c...

Embodiment 3

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

[0045] Step 3: Add 2000g (4.97 mol) of 2,9-bis(ethoxycarbonyl)-diethyl sebacate and 1498.3g (10.9 mol) of n-bromobutane into a 20L three-necked flask, and the mass concentration of the dropwise addition is 7739.0g (10.9 mol) 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 ℃ (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, ...

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Abstract

The invention relates to a co-production method for capacitance-grade 2-butylsebacic acid and 2, 9-butylsebacic acid. The co-production method comprises the steps of carrying out nucleophilic substitution reaction on diethyl malonate and 1, 6-dibromohexane serving as raw materials in a strong alkali solution to obtain 2, 9-bis(ethoxycarbonyl)-diethyl sebacate, then, enabling 2, 9-bis(ethoxycarbonyl)-diethyl sebacate to react with n-butyl bromide in the strong alkali solution, and distilling to obtain 2-butyl-2, 9-diethoxycarbonyldiethyl sebacate and 2, 9-dibutyl-2, 9-diethoxycarbonyldiethyl sebacate; and respectively saponifying, acidifying and carrying out decarboxylic reaction to obtain 2-butylsebacic acid and 2, 9-butylsebacic acid. Due to the improvement on a technological process, a byproduct, namely 2-butyl-8-thyoxyloctanoic acid is prevented from being generated, and high-purity 2-butylsebacic acid has more excellent electrochemical properties than 2-butyloctanedioic acid sold on the market, so that the oxidation efficiency of electrolyte is increased, and the co-production method has favorable market prospects.

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 (CN101805255 A, 2010-8-18); Ⅳ) 2,9-dibutyl sebacic acid...

Claims

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Application Information

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Patent Type & Authority Applications(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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