CN103086871B - Preparation method of dicarboxylic acid with branch at alpha position for aluminum electrolytic capacitor electrolyte - Google Patents
Preparation method of dicarboxylic acid with branch at alpha position for aluminum electrolytic capacitor electrolyte Download PDFInfo
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Abstract
The invention discloses a preparation method of dicarboxylic acid with a branch at an alpha position for aluminum electrolytic capacitor electrolyte. The method comprises the following steps of: adding an absolute ethyl alcohol solution of alkali into an anhydrous xylene solution of an ester shown as a general formula (1), dropping an anhydrous xylene solution of monohaloalkyl with carbon mumber being 1-12 for 4 hours at normal temperature, after heating refluxing for 8 hours, directly raising temperature to separate out xylene and ethanol, adding water for layering to obtain tetrabasic ester shown as a general formula (2), carrying out basification and acidification on the tetrabasic ester to obtain tetrabasic carboxylic acid shown as a general formula (3), dissolving the tetrabasic carboxylic acid in pyridine, and heating for refluxing to obtain the dicarboxylic acid with the branch at the alpha position, shown as a general formula (4). The preparation method disclosed by the invention has the advantages that the used deacidification method is low in temperature, easy to control, and the obtained product is high in purity and is more than 99%, does not influence high temperature performance of the electrolyte. The preparation method is applied to a high-voltage capacitor, extremely small in electrical characteristics deterioration and high temperature electrical conductivity, and pretty high in high temperature spark.
Description
Technical field
The present invention relates to the preparation method of α bit strip side chain di-carboxylic acid for a kind of aluminum electrolytic capacitor electrolyte.
Background technology
Present stage aluminium electrolutic capacitor used mesohigh electrolytic solution, to take ethylene glycol as solvent, add boric acid or ammonium pentaborate, add again 2-methyl nonane diacid, 2-butyl suberic acid, UB-20, nonane diacid, sebacic acid, 12 diacid and ammonium or amine salt etc. as the main solute of electrolytic solution, such electrolytic solution, at 105 ℃ or higher temperature, is easy to esterification.Under high temperature, As time goes on, specific conductivity declines very fast, and the oxide film repair ability that is anodizing to paper tinsel is poor, thereby affects performance and the life-span of electrical condenser.
The branched di-carboxylic acid in α position is because solubleness is large, and Heat stability is good, starts for aluminium electrolutic capacitor mesohigh electrolytic solution.The preparation method of the branched di-carboxylic acid in disclosed α position has multiple, but reactions steps is all more complicated.As Chinese patent CN1602532A and the disclosed synthetic method of CN101521117A, employing be all high temperature depickling.High temperature depickling, temperature is restive, and in product, by product is more, and sterling yield is lower and larger to the performance impact of electrolytic solution.
Summary of the invention
It is simple that technical problem to be solved of the present invention is to provide a kind of technique, be easy to control, and product purity and yield higher, the high-temperature behavior of electrolytic solution is not had to the preparation method of α bit strip side chain di-carboxylic acid for influential aluminum electrolytic capacitor electrolyte.
For solving the problems of the technologies described above, the preparation method of α bit strip side chain di-carboxylic acid for aluminum electrolytic capacitor electrolyte of the present invention, the steps include:
A) ester general formula of 1mol (1) being represented dissolves with 500mL anhydrous dimethyl benzene,
In formula, each R ＇ represents identical or different alkyl, and n is 0-12 integer;
B) by the alkali of 2mol with after 100mL anhydrous alcohol solution, in 25 ℃ of solution that join below a) step, reflux 15 minutes, cooling;
C), by single haloalkane of the carbon number 1-12 of 2mol, after dissolving with 150mL anhydrous dimethyl benzene, normal temperature splashes into b for lower 4 hours) in the solution of step, after reflux 8 hours, directly heat up and separate after dimethylbenzene and ethanol, add water stratification, obtain the tetracarboxylic ester that general formula (2) represents:
In formula, each R represents respectively identical or different alkyl, and the R ＇ in R and general formula (1) is identical or different;
D) tetracarboxylic ester that general formula (2) represents uses the aqueous sodium hydroxide solution alkaline hydrolysis of 15N after 8～12 hours, cooling, with the salt acid treatment of 6N, obtains the tetracarboxylic acid that general formula (3) represents:
E) tetracarboxylic acid that general formula (3) represents dissolves with pyridine again, and under reflux, decarbonate obtains the α bit strip side chain di-carboxylic acid that general formula (4) represents:
。
Total carbon number of the α bit strip side chain di-carboxylic acid that general formula (4) represents is generally 14-24, good 16-24, good 18-24, and best 18-22.Total carbon number is below 13, and the repair ability that is anodizing to the oxide film of paper tinsel is not very good, the side chain di-carboxylic acid of 24 above carbon numbers, and specific conductivity is lower.Embodiment has: 2, 5-dibutyl hexanodioic acid, 2, 5-dioctyl hexanodioic acid, 2, 5-dihexyl hexanodioic acid, 2, 5-diethyl hexanodioic acid, 2, 7-dibutyl suberic acid, 2, 7-dioctyl suberic acid, 2, 7-dihexyl suberic acid, 2, 7-diethyl suberic acid, 2, 9-dipropyl sebacic acid, 2, 9-dibutyl sebacic acid, 2, 9-dioctyl sebacic acid, 2, 9-diethyl suberic acid, 2, 11-dipropyl dodecanedioic acid, 2, 11-dibutyl dodecanedioic acid, 2, 11-dioctyl dodecanedioic acid, 2, 11-diethyl dodecanedioic acid, 2, 15-dipropyl Thapsic acid, 2, 15-dibutyl Thapsic acid, 2, 15-dioctyl Thapsic acid, 2, 15-diethyl Thapsic acid.Mixture a kind of or of more than two kinds can be used for aluminum electrolytic capacitor electrolyte.
The identical or different alkyl that the common carbon number of R in general formula is 3-8.R carbon number is 2 when following, sterically hindered less, can not suppress the esterification of it and ethylene glycol, and more than 8, its solubleness in ethylene glycol is less, and specific conductivity is lower.
R embodiment has: n-propyl group, n-butyl, n-amyl group, n-hexyl, n-heptyl, n--octyl group, sec.-propyl, isobutyl-, the tertiary butyl etc.
N in general formula is generally 1-12 integer, good is 4-8 integer.N is more than 13, and the solubleness in ethylene glycol is poor.
Alkali can be used the super bases such as sodium hydride, sodium ethylate, salt of wormwood, preferably sodium hydride.
Single haloalkane of carbon number 1-12 for technique scheme, the ester representing with general formula (1) under alkaline condition react, then alkaline hydrolysis, acidifying, decarbonate obtain the α bit strip side chain di-carboxylic acid of general formula (4) expression.The acid stripping method in pyridine solvent that the present invention is used, temperature is lower, is easy to the product purity controlling and obtain higher, can reach more than 99%, on the not impact of the high-temperature behavior of electrolytic solution.During gained α bit strip side chain di-carboxylic acid high temperature of the present invention, esterification is suppressed, and the oxide film repair ability that is anodizing to paper tinsel is stronger, and for high voltage capacitor, electrical characteristic worsen minimum, and high-temperature conductivity declines minimum, and high temperature sparking voltage is higher.Made electrolytic solution is at 85 ℃, and 2mA determines current measurement, and the lift velocity of sparking voltage is more than 50V/Min.Under condition of normal pressure, 150 ℃, after thermostatically heating test in 10 hours, specific conductivity rate of descent is below 30%.
Accompanying drawing explanation
Accompanying drawing is the schematic flow sheet of the inventive method.
Embodiment
The present invention is usingd drawings and Examples as explanation, but is not limited only to embodiment.
Referring to accompanying drawing, the preparation method of α bit strip side chain di-carboxylic acid for aluminum electrolytic capacitor electrolyte, the steps include:
A) ester general formula of 1mol (1) being represented dissolves with 500mL anhydrous dimethyl benzene,
In formula, each R ＇ represents identical or different alkyl, and n is 0-12 integer;
B) by the alkali of 2mol with after 100mL anhydrous alcohol solution, in 25 ℃ of solution that join below a) step, reflux 15 minutes, cooling;
C), by single haloalkane of the carbon number 1-12 of 2mol, after dissolving with 150mL anhydrous dimethyl benzene, normal temperature splashes into b for lower 4 hours) in the solution of step, after reflux 8 hours, directly heat up and separate after dimethylbenzene and ethanol, add water stratification, obtain the tetracarboxylic ester that general formula (2) represents:
In formula, each R represents respectively identical or different alkyl, and the R ＇ in R and general formula (1) is identical or different;
D) tetracarboxylic ester that general formula (2) represents uses the aqueous sodium hydroxide solution alkaline hydrolysis of 15N after 8～12 hours, cooling, with the salt acid treatment of 6N, obtains the tetracarboxylic acid that general formula (3) represents:
E) tetracarboxylic acid that general formula (3) represents dissolves with pyridine again, and under reflux, decarbonate obtains the α bit strip side chain di-carboxylic acid that general formula (4) represents:
。
Embodiment 1:2,7-ethyl dicarboxylate base suberic acid diethyl ester 374.1g, with anhydrous dimethyl benzene 500mL, dissolve, the sodium hydride 60g of massfraction 80%, with after 100mL anhydrous alcohol solution, 25 ℃ join in 2,7-ethyl dicarboxylate base suberic acid diethyl ester solution below, reflux 15 minutes, cooling, take 274g1 bromination of n-butane, after dissolving with 150mL anhydrous dimethyl benzene, normal temperature drips off for lower 4 hours, after reflux 8 hours, directly heat up and separate after dimethylbenzene and ethanol, add water stratification, obtain tetracarboxylic ester.Tetracarboxylic ester uses the aqueous sodium hydroxide solution alkaline hydrolysis of 15N after 812 hours again, cooling, with the salt acid treatment of 6N, obtains tetracarboxylic acid, and tetracarboxylic acid dissolves with pyridine again, and under reflux, decarbonate obtains 2,7-dibutyl suberic acid 125g.
Embodiment 2: 2 in embodiment 1, and 7-ethyl dicarboxylate base suberic acid diethyl ester 402g2,9-ethyl dicarboxylate base ethyl sebacate replaces, and other obtains 2,9-dibutyl sebacic acid 130g with example 1.
Embodiment 3: in embodiment 12,7-ethyl dicarboxylate base suberic acid diethyl ester substitutes with 2,15-ethyl dicarboxylate base hexadecane dicarboxylic acid diethyl ester 486g, and the other the same as in Example 1 obtains 2,15-dibutyl hexadecane dicarboxylic acid 175g.
The electrolytic solution of mesohigh electrolytic condenser, generally all contains solute and solvent.Solute is α bit strip side chain di-carboxylic acid and ammonium or amine salt, and massfraction is 1-40%, and solvent is ethylene glycol.α bit strip side chain di-carboxylic acid ammonium or general formula (5) expression for amine salt:
In formula, R ＂ represents NH
4or R-NH
2, R-NH wherein
2in R represent alkyl.
Amine has 1 grade of amine (methylamine, ethamine, quadrol etc.), 2 grades of amine (dimethylamine, diethylamine etc.), 3 grades of amine (Trimethylamine 99, triethylamine, diethyl methylamine, dimethyl amine, dimethyl Isopropylamine), and good is triethylamine.
The α bit strip side chain di-carboxylic acid ammonium that the carboxyl of the α bit strip side chain di-carboxylic acid that general formula (4) represents, general formula (5) represent or the ammonium of amine salt or the mol ratio of amido are 1:0～2, and that good is 1:1.2, preferably 1:0.8.Both add up to the weight percentage for electrolytic solution, and good is 1%～70%, and best is 5%～40%.
The polar organic solvent of aluminum electrolytic capacitor electrolyte has: the one kind or two or more mixture of alcohols, ethers, amides, lactone, carbonic ether.
(1), alcohols: 1 valency alcohol: methyl alcohol, ethanol, propyl alcohol, butanols etc.; Divalent alcohol: ethylene glycol, propylene glycol, Diethylene Glycol etc.; 3 valency alcohol: glycerine.
(2), ethers: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether.
(3), amides: N-METHYLFORMAMIDE, DMF, N, N-diethylformamide.
(4), lactone: gamma-butyrolactone.
(5), carbonic ether: methylcarbonate, diethyl carbonate, propylene carbonate, the rare ester of ethylene.
Other organic polar solvent: tetramethylene sulfone, DMI.
Above-mentioned solvent based, good is ethylene glycol.
(6), the weight percentage of above-mentioned solvent to electrolytic solution, be 5%～95% preferably, good is 60%～95%.
Electrolytic solution conventionally also need to add some additives as:
Phosphoric acid class: phosphoric acid, phosphoric acid ester.
Boric acid class: the carboxylate of the carboxylate of boric acid, boric acid and polyose, boric acid and polyvalent alcohol.
Nitro-compound: o-Carboxynitrobenzene, p-nitrobenzoic acid, 3-nitroacetophenone, o-NP, p-NP, o-Nitrophenyl methyl ether.In addition, for improving oxidation efficiency and the specific conductivity of electrolytic solution, also should suitably add some 2,3 grades of carboxylic acids.As hexanodioic acid, nonane diacid, 1,6-DDA, 2-methyl nonane diacid, M-nitro benzoic acid etc., but their total weight account for electrolytic solution gross weight should be below 10%.
Electrolytic solution pH should be controlled at 5～9.
The method that the ammonia salt that above-described embodiment 1,2,3 resulting materials are made is prepared electrolytic solution is: the ethylene glycol solution that ammonia salt is made into weight concentration 20%, be incorporated in 100 ℃～200 ℃ and boil 1～2 hour cetomacrogol 1000, boric acid, N.F,USP MANNITOL, ethylene glycol are mixed, be cooled to again 100 ℃～150 ℃ and add ammonium sebacate, poly carboxylic acid and ammonia salt ethylene glycol solution, additive constant temperature 30 minutes again, be cooled to 50 ℃.By weight, concrete example is as follows:
Concrete example 1:
2,7-dibutyl ammonium octanedioic acid ethylene glycol solution 30%
Ammonium sebacate 2%
Poly carboxylic acid 3%
Cetomacrogol 1000 2%
N.F,USP MANNITOL 2%
Boric acid 2%
Additive 1%
Ethylene glycol 58%
Concrete example 2:
2,9-dibutyl ammonium sebacate ethylene glycol solution 30%
Ammonium sebacate 2%
Poly carboxylic acid 3%
Cetomacrogol 1000 2%
N.F,USP MANNITOL 2%
Boric acid 2%
Additive 1%
Ethylene glycol 58%
Concrete example 3:
2,15-dibutyl Thapsic acid ammonium ethylene glycol solution 30%
Ammonium sebacate 2%
Poly carboxylic acid 3%
Cetomacrogol 1000 2%
N.F,USP MANNITOL 2%
Boric acid 2%
Additive 1%
Ethylene glycol 58%
Comparative example 1:
Alkyl ammonium sebacate ethylene glycol solution 30%
Ammonium sebacate 2%
Poly carboxylic acid 3%
Cetomacrogol 1000 2%
N.F,USP MANNITOL 2%
Boric acid 2%
Additive 1%
Ethylene glycol 58%
With the electrolytic solution of above-mentioned three concrete examples and comparative example make 450V4700 μ F76 * 150 bolt electrical condenser each 10, at 105 ℃, carry out endurance test, it is at 0H(hour) and the endurance test data of 500 H, 1000 H, 2000 H, 3000 H, 4000 H, 5000 H, 6000 H, 7000H, 8000H, 9000H, 10000H respectively in Table 1, table 2, table 3, table 4, table 5, table 6, table 7, table 8, table 9, table 10, table 11.
Table 1: aluminium electrolutic capacitor is at the endurance test table of 0H and 500 H
Table 2: aluminium electrolutic capacitor is at the endurance test table of 1000 H
Table 3: aluminium electrolutic capacitor is at the endurance test table of 2000 H
Table 4: aluminium electrolutic capacitor is at the endurance test table of 3000 H
Table 5: aluminium electrolutic capacitor is at the endurance test table of 4000 H
Table 6: aluminium electrolutic capacitor is at the endurance test table of 5000 H
Table 7: aluminium electrolutic capacitor is at the endurance test table of 6000 H
Table 8: aluminium electrolutic capacitor is at the endurance test table of 7000 H
Table 9: aluminium electrolutic capacitor is at the endurance test table of 8000 H
Table 10: aluminium electrolutic capacitor is at the endurance test table of 9000 H
Table 11: aluminium electrolutic capacitor is at the endurance test table of 10000 H
The electrical condenser that comparative example 1 is made explosion-proof plug when 3000H is seriously heaved and lost efficacy, three micro-drums of electrical condenser explosion-proof plug after 9000H that concrete example is made.
Claims (4)
1. a preparation method for α bit strip side chain di-carboxylic acid for aluminum electrolytic capacitor electrolyte, the steps include:
A) ester general formula of 1mol (1) being represented dissolves with 500mL anhydrous dimethyl benzene,
In formula, each R ＇ represents identical or different alkyl, and n is 0-12 integer;
B) by the alkali of 2mol with after 100mL anhydrous alcohol solution, in 25 ℃ of solution that join below a) step, reflux 15 minutes, cooling;
C), by single haloalkane of the carbon number 1-12 of 2mol, after dissolving with 150mL anhydrous dimethyl benzene, normal temperature splashes into b for lower 4 hours) in the solution of step, after reflux 8 hours, directly heat up and separate after dimethylbenzene and ethanol, add water stratification, obtain the tetracarboxylic ester that general formula (2) represents:
In formula, each R represents respectively identical or different alkyl, and the R ＇ in R and general formula (1) is identical or different;
D) tetracarboxylic ester that general formula (2) represents uses the aqueous sodium hydroxide solution alkaline hydrolysis of 15N after 8～12 hours, cooling, with the salt acid treatment of 6N, obtains the tetracarboxylic acid that general formula (3) represents:
E) tetracarboxylic acid that general formula (3) represents dissolves with pyridine again, and under reflux, decarbonate obtains the α bit strip side chain di-carboxylic acid that general formula (4) represents:
。
2. the preparation method of α bit strip side chain di-carboxylic acid for aluminum electrolytic capacitor electrolyte according to claim 1, is characterized in that: the n in described general formula (1) is 4-8 integer.
3. the preparation method of α bit strip side chain di-carboxylic acid for aluminum electrolytic capacitor electrolyte according to claim 1, is characterized in that: in described general formula (2), R is that carbon number is 3-8 identical or different alkyl.
4. the preparation method with α bit strip side chain di-carboxylic acid according to the aluminum electrolytic capacitor electrolyte described in claim 1,2 or 3, is characterized in that: described alkali is sodium hydride.
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| CN105037138A (en) * | 2015-07-06 | 2015-11-11 | 上海应用技术学院 | Preparation method for 2,9-dibutyl sebacate |
| CN105239128B (en) * | 2015-09-01 | 2018-03-30 | 广西贺州市桂东电子科技有限责任公司 | A kind of super-pressure Waste Acid From Hua Cheng Foil forms liquid and compound method |
| CN106098379B (en) * | 2016-08-08 | 2019-10-29 | 深圳市智胜新电子技术有限公司 | Electrolyte, the preparation method of electrolyte and aluminium electrolutic capacitor |
| CN108047028A (en) * | 2017-12-15 | 2018-05-18 | 中国石油大学(华东) | A kind of preparation method of capacitor stage 2,7- dibutyl suberic acids |
| CN109180540A (en) * | 2018-09-20 | 2019-01-11 | 武汉海斯普林科技发展有限公司 | A kind of preparation method and application of highly branched chain dicarboxylic acids ammonium salt |
| CN114380684A (en) * | 2022-02-21 | 2022-04-22 | 长春工业大学 | Carboxylic acid electrolyte with branched chain and preparation method thereof |
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| KR0173687B1 (en) * | 1991-02-28 | 1999-04-01 | 노보루 시마자끼 | Electrolyte for electrolytic capacitor and electrolytic capacitor using the same |
| WO2003026582A2 (en) * | 2001-09-26 | 2003-04-03 | Emisphere Technologies Inc. | Method of preparing phenoxy alkanoic, alkenoic, and alkynoic acids and salts thereof via a dicarboxylate intermediate |
| HU228776B1 (en) * | 2001-12-11 | 2013-05-28 | Okamura Oil Mill Ltd | Composition for electrolytic solution and process for producing the same |
| CN100432038C (en) * | 2003-09-19 | 2008-11-12 | 宇部兴产株式会社 | Method for producing nitrile compound, carboxylic acid compound or carboxylate compound |
| CN101521117B (en) * | 2009-03-27 | 2011-06-29 | 深圳新宙邦科技股份有限公司 | preparation method of alpha- dicarboxylic acids for electrolyte for aluminium electrolytic capacitor |
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