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WO2005027157A2 - Sel fusible a temperature ordinaire et dispositif electrochimique - Google Patents

Sel fusible a temperature ordinaire et dispositif electrochimique Download PDF

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Publication number
WO2005027157A2
WO2005027157A2 PCT/JP2004/013393 JP2004013393W WO2005027157A2 WO 2005027157 A2 WO2005027157 A2 WO 2005027157A2 JP 2004013393 W JP2004013393 W JP 2004013393W WO 2005027157 A2 WO2005027157 A2 WO 2005027157A2
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WO
WIPO (PCT)
Prior art keywords
group
tfsi
ion
room temperature
molten salt
Prior art date
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Ceased
Application number
PCT/JP2004/013393
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English (en)
Japanese (ja)
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WO2005027157A1 (fr
WO2005027157A3 (fr
Inventor
Hajime Matsumoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
National Institute of Advanced Industrial Science and Technology AIST
Original Assignee
National Institute of Advanced Industrial Science and Technology AIST
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
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Priority to JP2005513940A priority Critical patent/JP4478790B2/ja
Publication of WO2005027157A1 publication Critical patent/WO2005027157A1/fr
Publication of WO2005027157A2 publication Critical patent/WO2005027157A2/fr
Publication of WO2005027157A3 publication Critical patent/WO2005027157A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/54—Electrolytes
    • H01G11/58—Liquid electrolytes
    • H01G11/60—Liquid electrolytes characterised by the solvent
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/54—Electrolytes
    • H01G11/58—Liquid electrolytes
    • H01G11/62—Liquid electrolytes characterised by the solute, e.g. salts, anions or cations therein
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0567—Liquid materials characterised by the additives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the present invention relates to a room temperature molten salt (ionic liquid) and a room temperature molten salt electrochemical denoise.
  • Organic solvents are used as a medium for chemical synthesis and as a medium for the conversion of high densities of electrochemical denos (such as lithium batteries). Many organic solvents are volatile [ ⁇ raw and have a high boiling point and are volatile! ⁇ ⁇ ⁇ ⁇ 3 ⁇ 4 ⁇ ⁇ ⁇ "" "" "” “” “” “ Ah
  • An object of the present invention is to provide a highly safe, room-temperature molten salt as a difficult male or female.
  • Fig. 4 Variation of thermal capacity of various ionic liquids synthesized according to the present invention ⁇ (Radiation rate: 10. C / min) (organic i3 ⁇ 4: GBL: y-butyrolactone, PC: propylene carbonate) ECETMA-C1: ECETMA-TFSI is a room temperature molten salt obtained in Example 2.
  • TMOTFA-C1 TMOTFA-TFSI is the room temperature molten salt obtained in Example 4.
  • TMODA-C1 TMODA-TFSI is the room temperature molten salt obtained in Example 5.
  • Figures 5 and 6 show refilling.
  • the vertical axis is 3 ⁇ 4ffi (Voltage), and the horizontal axis is specific capacity 4 (Specffic capacity).
  • the present invention provides the following room-temperature melting electrochemical electrochemical.
  • the electrochemical device according to Item 2 which is a lithium secondary battery, an electric secondary capacitor, a solar cell, or an electoric chromic anode. Since the room-temperature solution of the present invention has non-volatility, it can be used as a non-volatile electrochemical device.
  • the melting point of the room temperature molten salt of the present invention is generally 100 ° C or lower, preferably 80 ° C or lower, more preferably 60 ° C or lower, further preferably 40 ° C or lower, and particularly preferably 25 ° C or lower.
  • Room temperature molten salt of C or less can be widely used.
  • the temperature of the molten salt is preferably lower than room temperature (25 ° C), more preferably 0 ° C or lower, and particularly preferably 1 The following is even more preferred.
  • the power component of the room-temperature molten salt of the present invention is obtained by adding a power source of ⁇ 4 ⁇ to the volatile solvent.
  • Examples of the cation include an ammonium group, a phonium cation such as a phomonium group, and a phome, and preferably an ammonium group.
  • 4 ⁇ can be introduced into one organic solvent compound, preferably one or two.
  • the organic solvent compound includes one or more oxygen atoms (for example, ethers, alcohols, esters, carbonates, cholesterols, alcohols, alcohols). Ether, etc.).
  • oxygen atoms for example, ethers, alcohols, esters, carbonates, cholesterols, alcohols, alcohols). Ether, etc.
  • the quaternary ammonium group is preferably introduced into a ⁇ atom instead of a ⁇ atom.
  • Such a cation is introduced into the organic solvent via a ⁇ alkylene group as needed.
  • the organic solvent include compounds having a boiling point at normal pressure of OO ° C to 300 ° C, preferably 30 ° C to 300 ° C, and which are solid or liquid at normal temperature. Compounds are exemplified:
  • Anoschcols ethylene glycol, propylene glycol, petitylene, recall, jetylene, recall, triethylenedalicol, etc .;
  • Alkylene alcohol monoalkyl ethers Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene alcohol monomethyl ether, propylene glycol monoethyl ether, petylene glycol U-e-nomethyl ether , Flenk U-monoethyl ether, diethylene glycol monomethyl ether, dimethylene glycol and ethyl ether, etc .; • Alkylene glycol, 3-: resin alkyl ethers: ethylene glycol; ⁇ -nordimethyletheno DME) polyethylene Rendarico 1 / regetyl ether, propylene glycol / ledimethyl ether, propylene glycol Recohol dimethinole ether, petitylene, Ricoh / directioninole ether, diethylene glycol, riconeole dimethyl ether, dimethylene glycolone regetyl, etc .; esters: acetyl acetate, ethy
  • Heteroalicyclic compounds ,: San, morpholine, pyrrolidine, etc .;
  • Sulfides dimethyl sulfide, getyl sulfide, di-n-propyl sulfide, dipropyl olenos sulfide, etc .;
  • Organic Solvent represents the above organic solvent
  • Ra represents an alkyl group
  • N represents a nitrogen atom
  • P represents a phosphorus atom
  • S represents Represents sulfur atoms
  • R 1 and R 2 are the same or different
  • T, T-alkyl group, haloalkyl group, alkoxy group, alkino group, reether group, Te Les indicates ⁇ 3 ⁇ 4 Yo Rere Ararukiru group or an alkoxyalkyl group
  • Zeta is NR 2 instar
  • R 1 ⁇ Hi R 2 is 3 ⁇ 4 ⁇ is the connexion 5-8 membered ring such together with the nitrogen atom T, even ⁇ , nitrogen-containing heterocyclic group ⁇ ⁇ ⁇ Tfc ⁇
  • X indicates de-fibre.
  • the haloalkyl group the number of carbon atoms in which at least one of the hydrogen atoms of the above alkyl group is a halogen atom (chlorine, bromine, fluorine, iodine), especially a fluorine atom:! To 20, preferably 1 to 6, More preferably, it is a haloalkyl group having a straight and fine branch having 3 to 3 carbon atoms;
  • the alkoxy group has (0—the above alkyl) structure having 2 carbon atoms.
  • Tb5 preferably a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms;
  • alkino group examples include those having a (S—alkyl) structure and having 20 to 20 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 3 carbon atoms.
  • aryl group examples include an aryl group having 6 to 10 carbon atoms such as a phenyl group, a tolyl group, a xylyl group, an ethylphenyl group, and a 1,3,5-trimethinolephenyl group; Tu5.
  • aralkyl group examples include aralkyl groups having 7 to 15 carbon atoms, such as benzyl, phenyl, naphthylmethyl and the like.
  • the alkoxy group and the alkoxy group of the alkoxyalkyl group are the same as those of flit, and the number of carbon atoms directly branched is! ⁇ 20.
  • alkyl groups of 20 Tokunime 1 Kinmechiru SiCH C DOO Q, main 1 Kinechiru 3 ⁇ 4 (03 ⁇ 4. ⁇ 2 0. ⁇ ), ethoxymethyl group (cao C ⁇ CH ⁇ Etokishechiru 3 ⁇ 4 ( ⁇ 3 ⁇ 4 ⁇ 3 ⁇ 4 ⁇ CH 2 CH exemplified is i ⁇ .
  • the polyether group - ⁇ ci - ⁇ - o -CCHC ⁇ o) ⁇ c r c 4 alkyl), or, - (ci-3 ⁇ 4-o-
  • nl is: a ⁇ 4 3 ⁇ 43 ⁇ 4, n2 is 1 to 4, the CrQ ⁇ Bruno Le, methyl, Echiru, n Examples include -propyl, isopropyl, n-butyl, igatyl, sec “butyl, and tert-butyl.
  • I ⁇ iR 2 is a 5- to 8-membered, preferably 5- or 6-membered nitrogen-containing heterocyclic group (pyrrolidinium) , Piberidinium, pyrrolychem, pyrididium, etc.).
  • An ether, ester or keto structure may be formed by interposing one or more ⁇ —, one COO—, or one CO— between C—C single bonds at any position of the badly alkyl group. .
  • aryl and aralkyl groups examples include halogen atoms (F, Cl, Br, I), 7-fiber, mesh, nitro, acetyl, and acetylamino.
  • X is a small number, and specific examples thereof include a chromium atom, a bromine atom, an iodine atom, a thiol group, and P- toluenesulfonyl;
  • the present invention introduces a quaternary ammonium group into a low-boiling, high-volatility, I-raw male to lead to a room temperature molten salt. 4 As described above, the conversion of ammonia and tertiary amines You may go and decompose the amino group of the amino acid nada.
  • the Anion component of the ambient temperature molten salt of the present invention is illustrated below; ⁇ Anio ⁇ fine possible 3 ⁇ 4> 3 ⁇ 4: • On: CI-, Br -, F one, ⁇ , SCN -, C10 4 - ,: BF 4 -, BC1 4 -, BBr 4 _, PF 6 -, -,
  • Lemonimide ion ⁇ (RSO ⁇ -, R is an alkyl group which may have a substituent, a halogenated alkyl group which may have a thigh, an aryl group which may have a substituent ⁇ ,
  • Monovalent or carboxylate ions for example, zwitterion, chiion, propionate ion, butyrate ion, velvet ion, isovalerate ion, trifluoroacetate ion, fluoroacetate ion, chloroacetate ion, trichloroacetate ion , Dichloro Rooster, Monochrome Mouth Rooster, Roof Acid, Gu! ; Cholate ion, lithium ion,
  • Rf-BF 3 (wherein, Rf represents CnF2n + l, and n represents 1-4 women), such as CF 3 BF 3 , Ji 2 , C BF 3 , and C 4 FgBF 3 ; Even if CnF2n + l is a fiber, it has a branch and Tfc is good.
  • the room-temperature molten salt of the present invention can be easily produced by mixing the above-mentioned components.
  • the above-mentioned cation component and thione component are each a single component, but the combination ratio of two or more components is good.
  • H— anion component
  • the room-temperature molten salt of the present invention is suitable for electrochemical denomination of lithium secondary batteries, electric two-capacitors, fuel tanks, solar cells, and the like, as well as the conversion of chemistry.
  • the room temperature molten salt of the present invention can be used in a lithium secondary battery, a room temperature molten salt that is electrochemically unstable to a highly active coal electrode or lithium anode (eg, 1- Etino 3-methylimidazolymtetraf (E.g., fluoroborate), and the passive stability of S to the negative electrode_h can significantly improve the apparent electrochemical stability.
  • a room temperature molten salt that is electrochemically unstable to a highly active coal electrode or lithium anode eg, 1- Etino 3-methylimidazolymtetraf (E.g., fluoroborate)
  • the passive stability of S to the negative electrode_h can significantly improve the apparent electrochemical stability.
  • the agent is also a molten salt at room temperature, the overall movement is maintained.
  • Example 1 Ionic liquefaction of shetan (DME): Synthesis of 1- (2-mequine-ethoxyshethyl) -tomethinopyridinium-bis (trifluoromethylsulfol-l) imide (MEE P FSI)
  • the synthesis was performed in the same order except that bromo ⁇ -butyrolactone was used instead of 1-bromoethoxy-2-methoxyethane in Example 1 until the synthesis of the bromide as a raw material (80% yield).
  • the solvent used for recrystallization was the acetone / ethanol power of Example 1, but ethanol / ethyl ether was used instead.
  • Substance (TMOTFA-TFSI) dissolves in carbon dioxide, so anion exchange to TFSI should be performed not in water, but in ethanol, and ethanol should be distilled off with ⁇ porator, and then dichlorometa / "e extraction (30% yield) ).
  • TMODA-TFSI by R The analysis values of TMODA-TFSI by R are as follows.
  • Figure 1 shows the change in the weight of heat in a material, which is the heat-resistant I. It is used as a battery for GBL and PCs.
  • the shelf solvent has a boiling point of 200. C or more, but 100 due to the presence of life. Volatile before C and the weight is reduced.
  • DEC is organic like GBL and PC? is there.
  • ECETMA-C1 is a salt that is solid at room temperature, but it is stable up to around 150 ° C.
  • the anion is exchanged for TFSI with TFSI (ECETMA-TFSI, room temperature). It is clear from Fig. 1 that the fiber (liquid) is further improved.
  • the use of the room-temperature molten salt of the present invention as a battery early liquid improves the age and performance.
  • EM-TFSI has lower electrochemical stability than ammonium-based, but has the advantage of relatively low viscosity.
  • the electrification reportability was poor, and the point was that it was used for carbon electrodes.
  • the force l that shows a large capacity of 50 QnL3 ⁇ 4g during charging (dotted line) is T at which irreversible reduction of EM cations occurs. It indicates that cation insertion has occurred and that both have occurred.
  • there is no capacity in the (Taihuai line) and a system with poor electrification characteristics such as EM-TFSI cannot use a coal electrode at all.
  • the EM-TFSI can produce a good 53 ⁇ 4m characteristic I in the EM-TFSI.
  • the strength of the ⁇ is due to the formation of the SEI coating on the surface of the BTJb from ECBTMA-TFSI, which suppresses the insertion of EI and carbon materials.
  • Leakage with a Carboel structure like GBL'EC or GBL'EC! "C known, o Organic solvents such as GBL and EC have problems with ⁇ I"
  • An ionic liquid having a violent viscosity is hardly viscous and has greatly improved heat resistance, which greatly contributes to safety.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Power Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • General Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Secondary Cells (AREA)
  • Electric Double-Layer Capacitors Or The Like (AREA)
  • Conductive Materials (AREA)

Abstract

La présente invention se rapporte à un sel fusible à température ordinaire, qui contient : un ingrédient cation, obtenu par l'introduction d'un groupe cationique dans un solvant organique volatil ; et un ingrédient anion, sélectionné parmi un ion inorganique, un ion sulfonimide, un ion acide carboxylique, un ion acide sulfonique mono ou polyvalent, (alkyle éventuellement substitué, cycloalkyle ou aryle)4B-, (R1SO2)3C- (où R1 représente alkyle éventuellement substitué, haloalkyle éventuellement substitué ou aryle éventuellement substitué), et Rf-BF3- (où Rf représente CnF2n+1, n étant un entier compris entre 1 et 4).
PCT/JP2004/013393 2003-09-09 2004-09-08 Sel fusible a temperature ordinaire et dispositif electrochimique Ceased WO2005027157A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2005513940A JP4478790B2 (ja) 2003-09-09 2004-09-08 常温溶融塩及び電気化学デバイス

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JP2003316471 2003-09-09
JP2003-316471 2003-09-09

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WO2005027157A3 WO2005027157A3 (fr) 2005-05-06

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Cited By (8)

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JP2011525173A (ja) * 2008-04-29 2011-09-15 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 反応性イオン液体
JP2012116802A (ja) * 2010-12-02 2012-06-21 Nitto Boseki Co Ltd イオン液体及びその製造方法
CN103130779A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的马来酰亚胺类离子液体及其制备方法和应用
CN103130783A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的四氢噻吩类离子液体及其制备方法和应用
CN103130776A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的咪唑类离子液体及其制备方法和应用
CN103130764A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的季铵盐类离子液体及其制备方法和应用
CN103130778A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的吡嗪类离子液体及其制备方法和应用
CN103130777A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的吡啶类离子液体及其制备方法和应用

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FR3002086B1 (fr) 2013-02-13 2015-03-27 Commissariat Energie Atomique Procede de synthese de liquides ioniques a groupe fonctionnel carbonate et liquides ioniques ainsi obtenus.

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JP2001035253A (ja) * 1999-07-19 2001-02-09 Fuji Photo Film Co Ltd 電解質組成物、光電変換素子および光電気化学電池
JP5081345B2 (ja) * 2000-06-13 2012-11-28 富士フイルム株式会社 光電変換素子の製造方法
JP4637334B2 (ja) * 2000-08-29 2011-02-23 富士フイルム株式会社 電解質組成物および電気化学電池
JP4240263B2 (ja) * 2000-12-22 2009-03-18 富士フイルム株式会社 電解質組成物及び非水電解質二次電池
JP2003201272A (ja) * 2001-07-31 2003-07-18 Tokuyama Corp オニウム塩
KR101090547B1 (ko) * 2003-02-13 2011-12-08 고에이 가가쿠 고교 가부시키가이샤 제4급 암모늄염
JP2004262897A (ja) * 2003-03-04 2004-09-24 Tosoh Corp ４級アンモニウム系常温溶融塩及び製造法

Cited By (13)

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Publication number Priority date Publication date Assignee Title
JP2011525173A (ja) * 2008-04-29 2011-09-15 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 反応性イオン液体
US9624160B2 (en) 2008-04-29 2017-04-18 Basf Se Reactive ionic liquids
US9006457B2 (en) 2008-04-29 2015-04-14 Basf Se Reactive ionic liquids
JP2012116802A (ja) * 2010-12-02 2012-06-21 Nitto Boseki Co Ltd イオン液体及びその製造方法
CN103130778A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的吡嗪类离子液体及其制备方法和应用
CN103130764A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的季铵盐类离子液体及其制备方法和应用
CN103130776A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的咪唑类离子液体及其制备方法和应用
CN103130777A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的吡啶类离子液体及其制备方法和应用
CN103130783A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的四氢噻吩类离子液体及其制备方法和应用
CN103130779B (zh) * 2011-12-01 2015-08-05 海洋王照明科技股份有限公司 含碳酸酯基团的马来酰亚胺类离子液体及其制备方法和应用
CN103130778B (zh) * 2011-12-01 2016-02-10 海洋王照明科技股份有限公司 含碳酸酯基团的吡嗪类离子液体及其制备方法和应用
CN103130783B (zh) * 2011-12-01 2016-04-13 海洋王照明科技股份有限公司 含碳酸酯基团的四氢噻吩类离子液体及其制备方法和应用
CN103130779A (zh) * 2011-12-01 2013-06-05 海洋王照明科技股份有限公司 含碳酸酯基团的马来酰亚胺类离子液体及其制备方法和应用

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JP4478790B2 (ja) 2010-06-09
JPWO2005027157A1 (ja) 2006-11-24
WO2005027157A3 (fr) 2005-05-06

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