CN101131897A - Aluminum electrolytic capacitor, preparing method for quaternary ammonium salt for super capacitor - Google Patents

Aluminum electrolytic capacitor, preparing method for quaternary ammonium salt for super capacitor Download PDF

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CN101131897A
CN101131897A CN 200610111648 CN200610111648A CN101131897A CN 101131897 A CN101131897 A CN 101131897A CN 200610111648 CN200610111648 CN 200610111648 CN 200610111648 A CN200610111648 A CN 200610111648A CN 101131897 A CN101131897 A CN 101131897A
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ammonium salt
quaternary ammonium
alkyl
carbon number
salt
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CN100561619C (en
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郑仲天
吴科国
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HUIZHOU CAPCHEM CHEMICALS CO., LTD.
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SHENZHEN XINYUBANG ELECTRONIC MATEIRALS TECHNOLOGY Co Ltd
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    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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    • Y02E60/13—Energy storage using capacitors

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Abstract

The present invention discloses a preparation methods of aluminum electrolytic capacitors and super capacitor using quaternary ammonium salt.This method uses quaternary ammonium salt containing carbonate-alkyl esters to react with complex ammonium fluoride salt, for example Fluoroboric acid , in a suitable solvent. This method is characterized by non- introduction of halogen elements and H2O during the manufacturing process. At the same time, this method would have a high yield, and its reaction operation is simple, and its raw materials are easy to get.

Description

The preparation method of aluminium electrolytic capacitor, quaternary ammonium salt for super capacitor
Technical field
The present invention relates to the preparation method of quaternary salt, mainly be meant the preparation method of a kind of aluminium electrolytic capacitor, quaternary ammonium salt for super capacitor.
Background technology
Known, the quaternary salt of tetrafluoro aluminic acid, tetrafluoro boric acid, hexafluorophosphoric acid is widely used in aluminium electrolytic capacitor and ultracapacitor, and the electrolyte as the electrolyte of these capacitors has high conductivity, thereby its prepared element also possesses good performance.
Japan Patent is opened flat 5-286981 (gloomy field chemistry), makes (C2H5) 4NFnHF with anhydrous hydrogen fluoride reaction with (C2H5) 4NBr in ice-water bath.Under 170 ℃, evaporate HF and obtain (C 2H5) 4NF2HF with the reaction of 51%BF3 methanol solution, is heated to 150 ℃ and removes methyl alcohol and unnecessary HF then, obtains with recrystallizing methanol again.
Japanese patent laid-open 11-310555 (Mitsui Chemicals) reacts in ice-water bath with carbonic acid monomethyl ester triethyl group-ammonium methyl and anhydrous HF and obtains (C2H5) 4NFnHF, and below operation is opened flat 5-286981 with the spy.
Japanese patent laid-open 11-315055 (Mitsui Chemicals) reacts with 42% tetrafluoroborate solution down at 25 ℃ with carbonic acid monomethyl ester triethyl group-ammonium methyl, under 60 ℃, 70mmHg, concentrate, make triethyl group-methyl ammonium tetrafluoroborate of 80%, add isopropyl alcohol and separate out, vacuumize and getting by triethyl group-methyl ammonium tetrafluoroborate.
The Japan Patent spy opens 2000-16995 (Mitsubishi Chemical) manufacture method, opens flat 11-310555 basically identical with the spy.
It is with etamon chloride (or tetraethylammonium bromide) and 30%HBF4 methanol solution reaction that the Japan Patent spy opens 2001-348388, is cooled to 0 ℃ and separates out tetrafluoro boric acid, and crystallization is dry down and get at 105 ℃.
Japanese patent laid-open 5-286981 and spy open flat 2001-348388 and all use chlorination (or bromination) quaternary ammonium salt as raw material, and aluminium electrolytic capacitor or ultracapacitor must control Cl with electrolyte -Or Br -All below 1ppm, make above method for making reach this requirement, operation meeting more complicated, the special simultaneously BF3 methanol solution of opening flat 5-286981 all must be anhydrous with the special methanol solution of opening flat 2001-348388HBF4, and raw material is not easy to obtain.
Japanese patent laid-open 11-310555 etc. must react with anhydrous HF, the equipment requirements height, and complicated operation, the anhydrous HF deep-etching has severe toxicity.
Japanese patent laid-open 11-3150555 must use the 42%HBF4 aqueous solution, introduces more moisture content, and removing the H2O process can be cumbersome.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of aluminium electrolytic capacitor, quaternary ammonium salt for super capacitor, by using carbonic acid mono alkyl ester quaternary ammonium salt, the ammonium salt of fluorine-containing complex acid such as tetrafluoro boric acid reacts in polar solvent, need not anhydrous HF, can not introduce H2O and Cl -, Br -
Realize that technical scheme of the present invention is: this method comprises
Quaternary ammonium salt and solvent are made into the solution that concentration is 20-40%;
In solution, add ammonium salt backflow 24-48 hour, then solvent is drained finished product;
Wherein: the mol ratio of quaternary ammonium salt and ammonium salt is 1: 1.
This technical scheme also comprises: described quaternary ammonium salt comprises carbonic acid mono alkyl ester class quaternary ammonium salt; Described ammonium salt comprises the ammonium salt of fluorine-containing complex acid.
Described quaternary ammonium salt anion, i.e. carbonic acid mono alkyl ester anion, its general formula is:
Figure A20061011164800091
Wherein: R 1For carbon number smaller or equal to 5 alkyl, be preferably methyl;
Described quaternary ammonium salt cationic, its general formula is:
Figure A20061011164800092
Wherein: R 2For carbon number is less than or equal to 5 alkyl, R 3, R 4, R 5For carbon number is the alkyl of 1-20, wherein R 2, R 3, R 4, R 5Can be connected to ring-type arbitrarily in twos.
Described quaternary ammonium salt cationic also comprises season imidazole salts cation, and its general formula is:
Figure A20061011164800093
Wherein: R 6, R 8For carbon number is less than or equal to 5 alkyl, R 7, R 9, R 10For H atom or carbon number are less than or equal to 5 alkyl, R 6, R 7, R 8, R 9, R 10Can be connected to ring-type arbitrarily in twos.
Described quaternary ammonium salt cationic also comprise season imidazoline or season pyrimidine moiety or season the amidine cation, its general formula is:
Figure A20061011164800101
Wherein, R11, R12, R14, R15 can be that carbon number is less than or equal to 5 alkyl, and R13 can be that H atom or carbon number are less than or equal to 5 alkyl, and wherein R11, R12, R13, R14, R15 can be connected to ring-type in twos.
Described quaternary ammonium salt cationic also comprises season pyridine or season pyrroles salt cation, and wherein the pyridiniujm general formula is season:
Wherein: the R16 carbon number is the alkyl of 1-5, and pyridine ring also can have alkyl or alkoxyl or ether or ketone group substituting group, and R16 is preferably methyl;
Season pyrroles salt general formula is:
Figure A20061011164800103
Wherein: R17 is that carbon number is the alkyl of 1-5, can be on the pyrrole ring by alkyl or alkoxyl or ether or ketone group group, and R17 is preferably methyl.
Described quaternary ammonium salt cationic also comprises the quaternary alkylphosphonium salt cation, and its general formula is:
Figure A20061011164800111
Wherein: R18 is that carbon number is less than or equals 5 alkyl, and R19, R20, R21 are the alkyl of carbon number 1-20, and R18, R19, R20, R21 can be connected to ring-type arbitrarily in twos.
Described ammonium salt anion comprises tetrafluoro boric acid anion or hexafluorophosphoric acid anion or tetrafluoro aluminic acid anion or hexafluoroarsenate anion or hexafluoro-antimonic acid anion;
Described ammonium salt cation comprises a kind of in the following cation, and its general formula is:
Figure A20061011164800112
Wherein, R22, R23, R24 are that H atom or carbon number are the alkyl of 1-3, can link to each other in twos arbitrarily between R22, R23, the R24.
Described solvent comprises alcohols or nitrile or amide-type or lactone or inorganic acid ester class or amine or sulfone class or ethers or phosphoramide types, wherein particular methanol or ethanol or acetonitrile or N, N-dimethylformamide.
Described method comprises that carbonic acid mono alkyl ester quaternary ammonium salt and ammonium tetrafluoroborate or ammonium hexafluorophosphate react in methyl alcohol or ethanol or acetonitrile or N, dinethylformamide solution.
The beneficial effect that the present invention has: the present invention carries out metathesis reaction with two kinds of salt (A and B) and makes, salt A is a carbonic acid mono alkyl ester quaternary ammonium salt, salt B is that the ammonium salt of tetrafluoro boric acid fluorine-containing complex acids such as (or hexafluorophosphoric acids) reacts in polar solvent, need not anhydrous HF, can not introduce H20 and Cl -, Br -Possess simple to operate, the raw material characteristics that are easy to get, H2O and Cl in the finished product -, Br -Control easily.
Embodiment
The present invention will be further described below in conjunction with embodiment:
The present invention carries out metathesis reaction with two kinds of salt (A and B) and makes, and salt A is a carbonic acid mono alkyl ester quaternary ammonium salt, and salt B is that the ammonium salt of fluorine-containing complex acids such as tetrafluoro boric acid reacts in polar solvent.
The present invention is with salt A anion, i.e. carbonic acid mono alkyl ester anion, and general formula is:
Figure A20061011164800121
R1 is a carbon number smaller or equal to 5 alkyl, is preferably methyl.
The used salt A cation of the present invention can be a quaternary ammonium salt cationic, its general formula:
Figure A20061011164800122
R2 is that carbon number is less than or equal to 5 alkyl.
R3, R4, R5 are that carbon number is the alkyl of 1-20.
R2, R3, R4, R5 can be connected to ring-type arbitrarily in twos.
As: tetramethyl-ammonium root, trimethyl-ethyl ammonium root, dimethyl diethyl ammonium root, triethyl group-ammonium methyl root, tripropyl-ammonium methyl root, tributyl-ammonium methyl root, trioctylphosphine-ammonium methyl root, tetraethyl ammonium root, trimethyl-propyl ammonium root, trimethylphenyl ammonium root etc.
The used salt A cation of the present invention can be a season imidazole salts cation, and its general formula is:
Figure A20061011164800131
R 6, R 8Be less than or equal to 5 alkyl for carbon number.
R 7, R 9, R 10For H former in or carbon number be less than or equal to 5 alkyl.
R 6, R 7, R 8, R 9, R 10Can be connected to ring-type arbitrarily in twos.
As 1,2,3-tri-methylimidazolium, 1,2,3,4-tetramethyl imidazoles, 1,3-dimethyl-2-ethyl imidazol(e), 1-methyl-2,3-diethyl imidazoles, 1,2,3-trimethyl-4-ethyl imidazol(e) etc., can also enumerate multiple as this type of salt ion.
The used salt A cation of the present invention can be the season imidazoline, season pyrimidine moiety and season the amidine cation, general formula is:
Figure A20061011164800132
R 11, R 12, R 14, R 15Can be that carbon number is less than or equal to 5 alkyl.
R 13Can be that H atom or carbon number are less than or equal to 5 alkyl.
R 11, R 12, R 13, R 14, R 15Can be connected to ring-type in twos.
As 1,2,3,4-tetramethyl imidazoline, 2,3-dimethyl-1-ethyl imidazol(e) quinoline, 1,2,3,4-tetramethyl pyrimidine moiety, 1,3-diethyl imidazoles, can enumerate many as this compounds.
The salt A cation that the present invention is used can be a season pyridine or season pyrroles salt cation, as season pyridiniujm its for general formula be:
Figure A20061011164800141
The R16 carbon number is the alkyl of 1-5, and pyridine ring also can have substituting groups such as alkyl, alkoxyl, ether, ketone group.The R16 preferable methyl.
As its general formula of season pyrroles salt can be:
Figure A20061011164800142
R17 is that carbon number is the alkyl of 1-5, can be by groups such as alkyl, alkoxyl, ether, ketone groups on the pyrrole ring.R17 is preferably methyl.
The used salt A cation of the present invention also can Shi quaternary alkylphosphonium salt cation, and its general formula is:
Figure A20061011164800143
R18 is that carbon number is less than or equals 5 alkyl.
R19, R20, R21 are the alkyl of carbon number 1-20.
R18, R19, R20, R21 can be connected to ring-type arbitrarily in twos.
As triphenyl-Jia Ji Phosphonium, tributyl-Jia Ji Phosphonium, triphenyl-Yi Ji Phosphonium, tributyl-Yi Ji Phosphonium etc.
Used salt B anion of the present invention can be tetrafluoro boric acid anion, hexafluorophosphoric acid anion and tetrafluoro aluminic acid anion, also can be hexafluoroarsenate anion, hexafluoro-antimonic acid anion.
The cation of used salt B of the present invention also can be a kind of in the following cation, and general formula is:
Figure A20061011164800151
R 22, R 23, R 24For H atom or carbon number are the alkyl of 1-3.
R 22, R 23, R 24Can be connected to ring-type arbitrarily in twos.
As NH 4+, CH 3NH 3+, (CH 3) 2NH 2+, (CH 3) 3NH +, C 2H 5NH 3+, (C 2H 5) 2NH 2+Deng, be preferably NH 4+
The used solvent of salt A of the present invention and salt B reaction is H2O or non-aqueous polar solvent, can select alcohols, nitrile, amide-type, lactone, inorganic acid ester class, amine, sulfone class, ethers, phosphoramide types etc., the lower solvents of boiling point such as particular methanol, ethanol, acetonitrile, N, dinethylformamide as non-aqueous polar solvent.
Used salt A of the present invention can get with corresponding compound reaction with carbonic ester, can be with reference to corresponding patent, and salt A is easy to get.
The present invention gets salt A and is made into 20% ~ 40% solution with above-mentioned solvent, with salt B (boiling) 24h-48h hour that reflux, then above-mentioned solvent is drained finished product.
The mol ratio of salt A and salt B was got 1: 1.
Embodiment 1:
Get carbonic acid mono-methyl-methyl triethyl ammonium 40% methanol solution 300g (0.63mol), put into the 1000ml there-necked flask, add ammonium tetrafluoroborate 66g (0.63mol), allow its backflow 24h, drain, get finished product-methyltriethylammonitetrafluoroborate tetrafluoroborate 115g, yield is 90%.
Embodiment 2:
Get carbonic acid mono-methyl-methyl triethyl ammonium 40% methanol solution 300g (0.63mol) and place the 1000ml there-necked flask, add ammonium hexafluorophosphate 103g (0.63mol), backflow 24h drains, and gets finished product methyl triethyl group ammonium hexafluorophosphate 141g, and yield is 86%.
Embodiment 3:
Carbonic acid mono-methyl 1,2,3-tri-methylimidazolium salt 40% methanol solution 300g (0.65mol) places the 1000ml there-necked flask, add ammonium tetrafluoroborate 68g (0.65mol), backflow 24h drains, and gets finished product tetrafluoro boric acid-1,2,3-tri-methylimidazolium salt 113g, yield is 88%.

Claims (10)

1. the preparation method of an aluminium electrolytic capacitor, quaternary ammonium salt for super capacitor is characterized in that described method comprises
A. quaternary ammonium salt and solvent are made into the solution that concentration is 20-40%;
B. in solution, add ammonium salt backflow 24-48 hour, then solvent is drained finished product;
Wherein: the mol ratio of quaternary ammonium salt and ammonium salt is 1: 1.
2. the preparation method of aluminium electrolytic capacitor as claimed in claim 1, quaternary ammonium salt for super capacitor is characterized in that described quaternary ammonium salt comprises carbonic acid mono alkyl ester class quaternary ammonium salt; Described ammonium salt comprises the ammonium salt of fluorine-containing complex acid.
3. the preparation method of aluminium electrolytic capacitor as claimed in claim 1 or 2, quaternary ammonium salt for super capacitor is characterized in that described quaternary ammonium salt anion, i.e. carbonic acid mono alkyl ester anion, and its general formula is:
Figure A2006101116480002C1
Wherein: R1 is a carbon number smaller or equal to 5 alkyl, is preferably methyl;
Described quaternary ammonium salt cationic, its general formula is:
Figure A2006101116480002C2
Wherein: R2 is that carbon number is less than or equal to 5 hydrocarbon base, and R3, R4, R5 are that carbon number is the alkyl of 1-20, and wherein R2, R3, R4, R5 can be connected to ring-type arbitrarily in twos.
4. the preparation method of aluminium electrolytic capacitor as claimed in claim 3, quaternary ammonium salt for super capacitor is characterized in that described quaternary ammonium salt cationic also comprises season imidazole salts cation, and its general formula is:
Figure A2006101116480003C1
Wherein: R6, R8 are that carbon number is less than or equal to 5 alkyl, and R7, R9, R10 are that H atom or carbon number are less than or equal to 5 alkyl, and R6, R7, R8, R9, R10 can be connected to ring-type arbitrarily in twos.
5. the preparation method of aluminium electrolytic capacitor as claimed in claim 3, quaternary ammonium salt for super capacitor, it is characterized in that described quaternary ammonium salt cationic also comprise season imidazoline or season pyrimidine moiety or season the amidine cation, its general formula is:
Figure A2006101116480003C2
Wherein, R11, R12, R14, R15 can be that carbon number is less than or equal to 5 alkyl, and R13 can be that H atom or carbon number are less than or equal to 5 alkyl, and wherein R11, R12, R13, R14, R15 can be connected to ring-type in twos.
6. preparation method's season pyridine of aluminium electrolytic capacitor as claimed in claim 3, quaternary ammonium salt for super capacitor or season pyrroles salt cation, wherein the pyridiniujm general formula is season:, it is characterized in that described quaternary ammonium salt cationic also comprises
Figure A2006101116480004C1
Wherein: the R16 carbon number is the alkyl of 1-5, and pyridine ring also can have alkyl or alkoxyl or ether or ketone group substituting group, and R16 is preferably methyl;
Season pyrroles salt general formula is:
Wherein: R17 is that carbon number is the alkyl of 1-5, can be on the pyrrole ring by alkyl or alkoxyl or ether or ketone group group, and R17 is preferably methyl.
7. the preparation method of aluminium electrolytic capacitor as claimed in claim 3, quaternary ammonium salt for super capacitor is characterized in that described quaternary ammonium salt cationic also comprises the quaternary alkylphosphonium salt cation, and its general formula is:
Figure A2006101116480005C1
Wherein: R18 is that carbon number is less than or equals 5 alkyl, and R19, R20, R21 are the alkyl of carbon number 1-20, and R18, R19, R20, R21 can be connected to ring-type arbitrarily in twos.
8. the preparation method of aluminium electrolytic capacitor as claimed in claim 1 or 2, quaternary ammonium salt for super capacitor is characterized in that described ammonium salt anion comprises tetrafluoro boric acid anion or hexafluorophosphoric acid anion or tetrafluoro aluminic acid anion or hexafluoroarsenate anion or hexafluoro-antimonic acid anion;
Described ammonium salt cation comprises a kind of in the following cation, and its general formula is:
Wherein, R22, R23, R24 are that H atom or carbon number are the alkyl of 1-3, and R22, R23, R24 can link to each other arbitrarily in twos.
9. the preparation method of aluminium electrolytic capacitor as claimed in claim 1, quaternary ammonium salt for super capacitor, it is characterized in that described solvent comprises alcohols or nitrile or amide-type or lactone or inorganic acid ester class or amine or sulfone class or ethers or phosphoramide types, wherein particular methanol or ethanol or acetonitrile or N, dinethylformamide.
10. the preparation method of aluminium electrolytic capacitor as claimed in claim 1 or 2, quaternary ammonium salt for super capacitor is characterized in that described method comprises that carbonic acid mono alkyl ester quaternary ammonium salt and ammonium tetrafluoroborate or ammonium hexafluorophosphate react in methyl alcohol or ethanol or acetonitrile or N, dinethylformamide solution.
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Cited By (4)

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CN101570491A (en) * 2008-04-30 2009-11-04 深圳新宙邦科技股份有限公司 Method for preparing tetrafluoroborate
CN101987824A (en) * 2009-07-31 2011-03-23 武汉凯门化学有限公司 Preparation method of high-purity conductive salt for super capacitor
CN102760574A (en) * 2011-04-27 2012-10-31 海洋王照明科技股份有限公司 Electric double layer capacitor electrolyte and electric double layer capacitor using electrolyte
CN107868053A (en) * 2016-09-22 2018-04-03 深圳新宙邦科技股份有限公司 A kind of preparation method of the hydrocarbyl carbonate salt of sulfuric acid one

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CN107221456B (en) * 2017-06-30 2020-04-28 北方民族大学 Aviation nickel-doped carbon-based super capacitor and preparation method thereof

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JP3702645B2 (en) * 1998-05-12 2005-10-05 三菱化学株式会社 Method for producing organic onium salt
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Publication number Priority date Publication date Assignee Title
CN101570491A (en) * 2008-04-30 2009-11-04 深圳新宙邦科技股份有限公司 Method for preparing tetrafluoroborate
CN101987824A (en) * 2009-07-31 2011-03-23 武汉凯门化学有限公司 Preparation method of high-purity conductive salt for super capacitor
CN101987824B (en) * 2009-07-31 2013-07-03 岳阳凯门科技有限公司 Preparation method of high-purity conductive salt for super capacitor
CN102760574A (en) * 2011-04-27 2012-10-31 海洋王照明科技股份有限公司 Electric double layer capacitor electrolyte and electric double layer capacitor using electrolyte
CN102760574B (en) * 2011-04-27 2015-08-26 海洋王照明科技股份有限公司 A kind of double electric layer capacitor electrolytic solution and use the double electric layer capacitor of this electrolyte
CN107868053A (en) * 2016-09-22 2018-04-03 深圳新宙邦科技股份有限公司 A kind of preparation method of the hydrocarbyl carbonate salt of sulfuric acid one
CN107868053B (en) * 2016-09-22 2021-05-14 深圳新宙邦科技股份有限公司 Preparation method of alkyl sulfate

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