CN100413873C - 离子型液体ⅱ - Google Patents

离子型液体ⅱ Download PDF

Info

Publication number
CN100413873C
CN100413873C CNB011228059A CN01122805A CN100413873C CN 100413873 C CN100413873 C CN 100413873C CN B011228059 A CNB011228059 A CN B011228059A CN 01122805 A CN01122805 A CN 01122805A CN 100413873 C CN100413873 C CN 100413873C
Authority
CN
China
Prior art keywords
ionic liquid
solvent
equal
less
trifluorophosphate
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
CNB011228059A
Other languages
English (en)
Other versions
CN1327986A (zh
Inventor
M·施米特
U·海德
W·盖斯勒
N·伊格纳蒂夫
V·希拉里斯
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.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of CN1327986A publication Critical patent/CN1327986A/zh
Application granted granted Critical
Publication of CN100413873C publication Critical patent/CN100413873C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00Secondary cells; Manufacture thereof
    • H01M10/06Lead-acid accumulators
    • H01M10/08Selection of materials as electrolytes
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01GCAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/004Details
    • H01G9/022Electrolytes; Absorbents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00Secondary cells; Manufacture thereof
    • H01M10/05Accumulators with non-aqueous electrolyte
    • H01M10/052Li-accumulators
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00Secondary cells; Manufacture thereof
    • H01M10/05Accumulators with non-aqueous electrolyte
    • H01M10/056Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564Accumulators 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
    • H01M10/0566Liquid materials
    • H01M10/0568Liquid materials characterised by the solutes
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/221Six-membered rings containing nitrogen and carbon only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/223Five-membered rings containing nitrogen and carbon only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/223Five-membered rings containing nitrogen and carbon only
    • C10M2215/224Imidazoles
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/063Ammonium or amine salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01Physico-chemical properties
    • C10N2020/077Ionic Liquids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10Inhibition of oxidation, e.g. anti-oxidants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/08Hydraulic fluids, e.g. brake-fluids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/14Electric or magnetic purposes
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M6/00Primary cells; Manufacture thereof
    • H01M6/14Cells with non-aqueous electrolyte
    • H01M6/16Cells with non-aqueous electrolyte with organic electrolyte
    • H01M6/162Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte
    • H01M6/164Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte by the solvent
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/13Energy storage using capacitors

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Electrochemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Power Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Physics & Mathematics (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Secondary Cells (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electric Double-Layer Capacitors Or The Like (AREA)

Abstract

本发明涉及用于电化学电池和有机合成的离子型液体。

Description

离子型液体Ⅱ
本发明涉及用于电化学电池和有机合成中的离子型液体。
美国专利US 2446331中第一次描述了无溶剂的离子型液体或“在室温下熔化的盐类”。这些强路易斯酸存在的问题是与大气中的潮气接触易形成有毒气体。
人们对涉及AlCl3和1-乙基-3-甲基咪唑(EMI)氯化物的化合物进行了长期研究。Wilkes和Zaworotko于1992年发现了新型无溶剂的离子型液体,EMI BF4和EMI O2CCH3,见J.Chem.Soc.,Chem.Commun.,第965页。但是,这些化合物不适宜在电化学电池中用做电解质,因为BF4和CH3CO2阴离子甚至在相对低的电位下也易被氧化.
德国专利DE 196 41138中描述了一种新型导电盐,氟代烷基磷酸锂。这些盐具有十分突出的高电化学稳定性和低水解倾向。(M.Schmidt et al.10thInternational Meeting on Lithium Batteries,Como 2000)。在循环实验中,这些化合物显示特别好的结果,且被证明是特别稳定的。
美国专利US 5827602描述了离子型液体的用途,该组离子型液体选自包含吡啶,哒嗪,嘧啶,吡嗪,咪唑,吡唑,噻唑,噁唑,和***盐的一组,在电化学电池中含有亚氨盐和甲烷盐(Methanide)作为阴离子。这些离子型液体由于具有良好的导电性特别适合于这种用途。其重要的缺点在于原材料特别是阴离子的昂贵合成。
本发明的目的在于提供具有大的液体范围,高热稳定性,低腐蚀性及较低合成造价的阴离子的离子型液体。
本发明的目的通过通式为下式的离子型液体实现:
K+A-(I)
其中,K+为阳离子,选自:
Figure C0112280500051
其中R1到R5相同或不同,可选择地通过一单键或双键彼此直接键合,且每个单独或一起具有以下的意义:
-H,
-卤素,
-烷基(C1到C8),它可部分或全部被进一步的基团,优选F,Cl,N(CnF(2n+1-x)Hx)2,O(CnF(2n+1-x)Hx),SO2(CnF(2n+1-x)Hx)或CnF(2n+1-x)Hx取代,其中1<n<6且0<x≤2n+1
且A-为阴离子,选自:
[PFx(CyF2y+1-zHz)6-x]-
其中1≤x<6
1≤y≤8,以及
0≤z≤2y+1。
优选的是,本发明的目的是通过通式为下式的离子型液体实现:
K+A-(I)
其中:
K+为阳离子,选自:
其中R1到R5相同或不同,任意选择地通过一单键或双键彼此直接键合,且每个单独或一起具有以下的意义:
-H,
-卤素,
-具有1-8个碳原子的烷基基团,
且A-为选自如下的阴离子:
[PFx(CyF2y+1-zHz)6-x]-
其中1≤x<6
1≤y≤8
0≤z≤2y+1,
而且上述阴离子不包括[(CF3)2PF4]-、[(CF3)3PF3]-、[(CF3)4PF2]-、[(CF3)5PF]-和[(CF3)6P]-
这些离子型液体适合作为有机合成的溶剂,但也可以用于电化学电池。另外,这些离子型液体还适合于用作有机反应的催化剂。另外,它们还适用于作为高反应活性的化学品的惰性溶剂。还可以用于液压液体领域。
已发现本发明化合物由于使用了全氟烷烃链,优选使用相对长链的全氟烷烃因而是疏水的。而且无水合成最大限度地减少了不希望带入反应体系的水分。
令人惊奇的发现离子型液体是不腐蚀的,但比通常用于电化学电池的铝电流集电器更钝化。这使得循环稳定性增加。另外,通过使用离子型液体可观察到体系的热稳定性的改善。
人们发现加入低粘度的溶剂可提高导电性。低粘度和高导电性是用于电化学电池的先决条件。本发明的化合物具有大的液体范围,使得它们特别适合这种应用。
用于双层电容器的先决条件是高导电性。本发明的化合物满足这一标准,因此可单独使用或以与其它溶剂或导电盐的混合物的形式使用。这些适合的溶剂选自有机碳酸酯(例如,碳酸亚乙酯,碳酸亚丙酯,及其衍生物,碳酸亚丁酯,碳酸二甲酯,碳酸二乙酯,碳酸乙基甲基酯,等),有机羧酸酯(例如,γ-丁内酯,甲酸甲酯,乙酸甲酯,乙酸乙酯,丙酸乙酯,丙酸甲酯,丁酸甲酯,丁酸乙酯,等),有机羧酸酰胺(例如,二甲基甲酰胺,甲基甲酰胺,甲酰胺等),有机醚(例如,1,2-二甲氧基乙烷,四氢呋喃,2-甲基四氢呋喃,四氢呋喃衍生物,1,3-二氧环戊烷,二氧杂环己烷,二氧杂环戊烷衍生物等)或其它对质子惰性的溶剂(例如乙腈,环丁砜。二甲亚砜。硝基甲烷,磷酸三酯,三甲氧基甲烷,3-甲基-2-噁唑烷二酮等)。同样的也可以使用溶剂的混合物,例如碳酸亚乙酯/碳酸二甲酯(ECIDMC)。
本发明的化合物可与常规导电性盐一起用于惯常的电解质中。它们可以1-99%存在于混合物中。适合的电解质的例子为带有选自如下的导电盐的电解质:LiPF6,LiBF4,LiClO4,LiAsF6,LiCF3SO3,LiN(CF3SO2)2和LiC(CF3SO2)3及其混合物。
该电解质也包含有机异氰酸酯(DE 199 44 603)以减少水含量。
也提供了通式(DE 199 51 804)如下的复合盐:
Mx+[EZ]y- x/y
其中:
x和y为1,2或3,
Mx+为金属离子,
E为一种Lewis酸,选自:
BR1R2R3,AlR1R2R3,PR1R2R3R4R5,AsR1R2R3R4R5和VR1R2R3R4R5
R1到R5可相同或不同,可选择地直接与另一个基团通过一单键或双键键合,且每个单独或一起为:
卤素(F,Cl或Br),
烷基或烷氧基(C1到C8),它们可被部分或全部被F,Cl或Br取代,
芳香环,任意选择地通过氧键合,选自:苯基,萘基,蒽基和菲基,这些基团可以是来取代的,或被烷基(C1至C8)或F,Cl或Br单取代到多取代,
芳香杂环,任意选择地通过氧键合,选自:吡啶基,吡唑基和嘧啶基,这些基团可以是未取代的,或被烷基(C1至C8)或F,Cl或Br单取代到多取代,
Z为OR6,NR6R7,CR6R7R8,OSO2R6,N(SO2R6)(SO2R7),C(SO2R6)-(SO2R7)(SO2R8)或OCOR6,其中
R6到R8相同或不同,可选择地直接与另一个基团通过一单键或双键键合,且每个单独或一起为:
氢或如R1到R5的定义,
通过相应的硼或磷Lewis酸/溶剂加合物与亚氨化锂或四烷基铵,methanide或三氟甲磺酸盐反应制备。
也提供了通式如下的硼酸盐(DE 199 59 722):
Figure C0112280500081
其中:
M为金属离子或四烷基铵离子,
x和y为1,2或3,
R1到R4相同或不同,为烷氧基或羧基(C1-C8),它们任意选择地直接与另外的基团通过单键或双键键合。这些硼酸盐可如下制备,使四烷氧基硼酸锂或烷氧基锂与硼酸的1∶1混合物,与适合的羟基或羧基化合物在对质子惰性的溶剂中按2∶1或4∶1的比例反应
也可以存在添加剂,例如通式如下的硅烷化合物:
SiR1R2R3R4
其中R1到R4
H
CyF2y+1-zHz
OC(O)CyF2y+1-zHz
OSO2CyF2y+1-zHz
且1<x<6
1<y<8
0<z<2y+1
R1-R4可相同或不同,为选自苯基和萘基的芳香环,而苯基或萘基可以是非取代的或被下面基团单取代或多取代:F,CyF2y+1-zHz,OCyF2y+1-zHz,OC(O)CyF2y+1-zHz,OSO2CyF2y+1-zHz或N(CyF2y+1-zHz)2,或为选自吡啶基,吡唑基,或嘧啶基的杂芳环,该这些基团中的每一个可被下面基团单取代或多取代:F,CyF2y+1- zHz,OCyF2y+1-zHz,OC(O)CyF2y+1-zHz,OSO2 CyF2y+1-zHz或N(CyF2y+1-zHz)2(DE 100 27626)。
本发明的化合物也可以用于含有下式表示的氟烷基磷酸锂电解质:
Li+[PFx(CyF2y+1-zHz)6-x]-
其中1≤x≤5
3≤y≤8
0≤z≤2y+1
配体(CyF2y+1-zHz)可以相同或不同,只是以下通式化合物除外:
Li+[PFa(CHbFC(CF3)d)c]-
其中,a为2-5的整数,b=0或1,c=0或1,d=2,e为1-4的整数,前提是b和c不能同时分别为0,且a+e的和等于6,配体(CHbFC(CF3)d)可以相同或不同(DE 100 089 55)。
制备氟烷基磷酸锂的方法,其特征在于至少一种通式为下式的化合物:
HmP(CnH2n+1)3-m
OP(CnH2n+1)3
ClmP(CnH2n+1)3-m
FmP(CnH2n+1)3-m
CloP(CnH2n+1)5-o
FoP(CnH2n+1)5-o
其中,0<m<2,1<n<8且0<o<4,
通过在氟化氢中电解氟化,得到的氟化产物的混合物通过提取,相分离和/或蒸馏加以分离,得到的氟化的烷基膦(phosphorane)在质子惰性的溶剂混合物中,在除去水分的条件下与氟化锂反应,得到的盐提纯并用常规方法分离。
本发明的化合物也可以用于含有下式的盐的电解质:
Li[P(OR1)a(OR2)b(OR3)c(OR4)dFe]
其中0<a+b+c+d≤5且a+b+c+d+e=6,R1到R4,各自独立的为烷基,芳基或杂芳基基团,其中R1到R4至少两个可与另外一个通过单键或双键直接键合(DE 100 16 801)。该化合物可通过下面制备:将通式如下的磷(V)化合物:
Li[P(OR1)a(OR2)b(OR3)c(OR4)dFe]
其中0<a+b+c+d≤5且a+b+c+d+e=5,R1到R4的定义如上,与氟化锂在有机溶剂存在下反应。
电解质中也可存在下面通式的离子型液体:
K+A-
其中,K+为选自如下的阳离子:
Figure C0112280500101
其中R1到R5相同或不同,可选择地直接与另一个基团通过一单键或双键键合,且每个单独或一起具有以下的意义:
-H,
-卤素,
-烷基(C1到C8),可被部分或全部被进一步的下列基团取代:F,Cl,N(CnF(2n+1-x)HX)2,O(CnF(2n+1-x)HX),SO2(CnF(2n+1-X)HX)或CnF(2n+1-X)HX,其中1<n<6且0<x≤2n+1
且A-为选自如下的阴离子:
[B(OR1)n(OR2)m(OR3)o(OR4)p]-
其中0<n,m,o,p≤4,且
m+n+o+p=4,
其中,R1到R4不同或成对的相同,可选择地直接与另一个基团通过一单键或双键键合,且每个单独或一起为:
芳环,选自:苯基,萘基,蒽基和菲基,这些基团可以是未取代的,或被下列基团单取代到多取代;CnF(2n+1-x)HX,其中1<n<6且0<x≤13,或卤素(F,Cl或Br),
芳杂环,选自:吡啶基,吡唑基和嘧啶基,这些基团可以是未取代的,或被下列基团单取代到多取代;CnF(2n+1-x)HX,其中1<n<6且0<x≤13,或卤素(F,Cl或Br),
烷基(C1到C8),可部分或全部被进一步的基团、优选F,Cl,N(CnF(2n+1-x)HX)2,O(CnF(2n+1-x)HX),SO2(CnF(2n+1-x)HX或CnF(2n+1-x)HX,其中1<n<6和0<x≤13,取代
或OR1到OR4
单独或一起为芳香或脂肪羧基,二羧基,氧代磺酰基,或氧代羰基基团,这些基团可部分或全部被进一步的基团、优选F,Cl,N(CnF(2n+1-x)HX)2,O(CnF(2n+1-x)HX),SO2(CnF(2n+1-x)HX)或CnF(2n+1-x)HX,其中1<n<6和0<x≤13取代(DE 10026565)。
根据本发明的化合物也可以用在包含下面通式的化合物的电解质中:
NR1R2R3
其中,R1和R2为H,CyF(2y+1-z)Hz或(CnF2n-mHm)X,其中X为芳香的或杂环的基团,
R3为(CnF2n-mHm)Y,其中Y为杂环基团,或(CoF2o-pHp)Z,其中Z为芳香基团,
且其中n,m,o,p,y和z满足下列条件:
0≤n≤6
0≤m≤2n
2≤o≤6
0≤p≤2o,
1≤y≤8且
0≤z≤2y+1,
用于在电化学电池中减少对质子惰性的电解质体系的酸含量。
也可以使用通式如下的氟烷基磷酸盐:
Mn+[PFx(CyF2y+1-zHz)6-x]-
其中:
1≤x≤6
1≤y≤8
0≤z≤2y+1
1≤n≤3,且
Mn+为单价或三价阳离子,特别是:
NR1R2R3R4
PR1R2R3R4
P(NR1R2)kR3 mR4 4-k-m(基中k=1-4,m=0-3且k+m≤4),
C(NR1R2)(NR3R4)(NR5R6),
C(烷基)3,Rb或托品基(tropylium),
其中R1到R8为H,烷基或芳基(C1-C8),可被F,Cl或Br部分取代,
其中,排除Mn+=Li+,Na+,Cs+,K+和Ag+的情况。这些氟烷基磷酸盐通过将正磷与氟化物,或金属氟烷基磷酸盐与氟化物或氯化物在有机非质子溶剂中反应得到(DE 100 388 58)。
电解质也可以包含下面的混合物:
a)至少一种下面通式的氟烷基磷酸锂:
Li+[PFx(CyF2y+1-zHz)6-x]-
其中:
1≤x≤5
1≤y≤8且
0≤z≤2y+1
在每中情况下配体CyF2y+1-zHz可相同或不同,及
b)至少一种聚合物(DE 100 58 264)。
电解质还可以包括下面通式的四氟烷基硼酸盐:
Mn+([BR4]-)n
其中,Mn+为单价,二价或三价阳离子,
在每种情况下配体R相同,为(CxF2x+1),其中1≤x≤8,且n=1,2或3(DE100 558 11)。制备四氟烷基硼酸盐的方法,其特征在于至少有一种通式为Mn+([B(CN)4]-)n的化合物,其中Mn+和n的定义如上,通过与至少一种氟化试剂在至少一种溶剂中氟化,得到的被氟化的化合物通过常规方法提纯和分离。
电解质还可以包括下面通式的硼酸盐:
Mn+[BFx(CyF2y+1-zHz)4-x]n -
其中
1<x<3,1≤y≤8且0≤z≤2y+1,
M为除了钾和钡之外的单价到三价阳离子(1≤n≤3),
特别是:
Li,
NR1R2R3R4,PR5R6R7R8,P(NR5R6)kR7 mR8 4k-m(其中k=1-4,m=0-3且k+m≤4),或
C(NR5R6)(NR7R8)(NR9R10),其中
R1到R4为CyF2y+1-zHz
R5到R10为H或CyF2y+1-zHz,或
芳香杂环阳离子,优选含氮和/或氧和/或硫的芳香杂环阳离子(DE 101 03189)。制备这些化合物的特征在于:
a)1∶1的BF3/溶剂复合物与烷基锂在冷却下反应,缓慢升温下除去大部分的溶剂,而后过滤得到的固体,用适当的溶剂洗涤,
b)在适当的溶剂中锂盐与B(CF3)F3盐1∶1的反应,混合物升温搅拌,除去溶剂,向反应混合物中加入非质子非水溶剂,优选那些用于电化学电池中的溶剂,将反应混合物干燥,或
c)B(CF3)F3盐与锂盐按1∶1到1∶1.5的比例在水中在升温下反应,在沸点下加热0.5到2小时,除去水,向反应混合物中加入非质子非水溶剂,优选那些用于电化学电池中的溶剂,将反应混合物干燥。
电解质也可以包含下面通式的氟烷基磷酸盐:
Mn+[PFx(CyF2y+1-zHz)6-x]n -
Mn+为单价,二价或三价阳离子,
1≤x≤5
1≤y≤8且
0≤z≤2y+1,n=1,2或3,在每种情况下配体(CyF2y+1-zHz)可以相同或不同,其中氟烷基磷酸盐中
Mn+为锂阳离子,且盐
M+([PF4(CF3)2]-)中M+=Cs+,Ag+或K+
M+([PF4(C2F5)2]-)中M+=Cs+
M+([PF3(C2F5)3]-)中M+=Cs+,K+,Na+或对-Cl(C6H4)N2 +
M+([PF3(C3F7)3]-)中M+=Cs+,K+,Na+,对-Cl(C6H4)N2 +或对-O2N(C6H4)N2 +,被排除(DE 100 558 12)。制备这些氟烷基磷酸盐的特征在于:至少一种下面通式的化合物:
HrP(CsH2s+1)3-r
OP(CsH2s+1)3
ClrP(CsH2s+1)3-r
FrP(CsH2s+1)3-r
CltP(CsH2s+1)5-t和/或
FtP(CsH2s+1)5-t
其中,在每种情况下:
0≤r≤2
3≤s≤8且
0≤t≤4,
通过在氟化氢中电解被氟化,得到的氟化产物混合物分离,将得到的氟化的烷基磷酸在非质子溶剂或在除去水分的溶剂的混合物中与下面的通式的化合物反应:
Mn+(F-)n,其中Mn+和n如上述所定义,
得到的氟烷基磷酸盐通过常规方法提纯和分离。
本发明的化合物也可以用于含有下式的氟烷基磷酸盐(DE 10109032)电解质中:
(Ma+)b[(CnF2n+1-mHm)yPF5-y(CR1R2)xPF5-y(CnF2n+1-mHm)y](2-) (a+b/2)
其中,
Ma+为单价,二价或三价阳离子,
a=1,2或3,b=2对应于a=1,b=2对应于a=3,b=1对应于a=2,且在每种情况下:
1≤n≤8,
0≤m≤2对应于n=1或2,
0≤m≤4对应于3≤n≤8
1≤x≤12,
0≤y≤2
其中在每种情况下R1和R2相同或不同,选自:氟,氢,烷基,氟烷基和全氟烷基取代基,且
在其中每种情况下,取代基(CnF2n+1-mHm)相同或不同。这些化合物如下制备:将至少一种氟-α,ω-双(烷基氟代磷酰)烷烃与至少一种通式为(Ma+)[F-]a,其中(Ma+)和a的定义同上的氟盐在溶液中反应,得到氟烷基磷酸盐,并在必要时用常规方法对后者加以提纯和/或分离。
本发明的化合物可用于下面的电化学电池的电解质,其阳极材料由涂覆的金属核构成。金属选自Sb,Bi,Cd,In,Pb,Ga和锡或它们的合金(DE 100 16 024)。制备这种阳极材料的方法的特征在于:
a)制备一种金属或合金核在乌洛脱品中的悬浊液或溶液,
b)将该悬浊液在的C5-C12-烷烃中乳化,
c)将乳化液沉淀在金属或合金核上,
d)通过加热体系将金属氧化物或过氧化物转化为相应的氧化物。
本发明的化合物还可用于下面的电化学电池的电解质,其阴极材料由通常的锂嵌入或***化合物制成。阴极材料也可以由用一种或多种金属氧化物涂覆的混合金属氧化物锂颗粒构成(DE 199 22 522)。它们也可以由用一种或多种聚合物涂覆的混合金属氧化物锂颗粒构成(DE 199 46 066)。本发明的化合物同样可以用于下面的阴极体系,其阴极由用一种或多种碱金属化合物和金属氧化物涂覆的混合金属锂颗粒构成(DE 100 14 884)。制备这些材料的特征在于:将颗粒悬浮于有机溶剂中,加入悬浮于有机溶剂中的碱金属盐化合物,加入溶于有机溶剂的金属氧化物,向悬浊液中加入水解溶液,随后过滤被涂覆的颗粒,干燥并煅烧。本发明的化合物也可以用于含有浸渍了氧化锡的阳极材料的体系(DE 100 25761)。这些阳极材料可按下面方法制备:
a)向氯化锡溶液中加入尿素,
b)向溶液中加入乌洛脱品和适宜的浸渍化合物,
c)得到的溶液在石油醚中乳化,
d)洗涤得到的凝胶,抽滤除去溶剂,
e)干燥并加热该凝胶。
本发明的化合物还可以用于含有用还原的锡氧化物制成的阳极材料的体系(DE 100 257 62)。阳极材料如下制备:
a)向氯化锡溶液中加入尿素,
b)向溶液中加入乌洛脱品,
c)得到的溶液在石油醚中乳化,
d)洗涤得到的凝胶,抽滤除去溶剂,
e)干燥并加热该凝胶。
f)将得到的SnO2暴露在一可通空气的反应炉中暴露在还原气蒸汽中。
下面将对本发明的一般实施例加以详细解释。
阴离子选自由下式构成的一组:
[PFx(CyF2y+1-zHz)6-x]-
其中1≤x≤6
1≤y≤8且
0≤z≤2y+1
按照DE 196 411 38所使用的方法制备。
阳离子选自下面构成的一组:
Figure C0112280500171
由已知的US 5827602中的方法制备。将起始原料在对质子惰性的有机溶剂中,在溶剂为液体范围的温度下反应0.5到12小时,优选1-4小时。
为除去副产物,将混合物冷却至-30℃,例如在LiCl为副产物的情况下,冷却至-10℃到-20℃,将沉淀的副产物过滤除去,优选在真空下过滤。
溶剂/产物的混合物可以直接用于电解质中。在必要时,可蒸馏除去溶剂,将得到的产物干燥以用于所述是用途。
下面的实施例旨在对本发明加以详细说明,但不限制发明。
实施例
实施例1
三(五氟乙基)三氟磷酸1-乙基-3-甲基咪唑鎓的合成
三(五氟乙基)三氟磷酸锂按照DE 196411 38的方法合成。产物在乙腈中按照下面反应式进行反应:
Figure C0112280500172
反应混合物在冷却下用玻璃漏斗真空过滤,以除去所形成的LiCl副产物。在减压下蒸馏除去溶剂,得到的三(五氟乙基)三氟磷酸1-乙基-3-甲基咪唑鎓在减压下干燥。
实施例2
三(五氟乙基)三氟磷酸1,2-二甲基-3-丙基咪唑鎓
三(五氟乙基)三氟磷酸锂按照DE 196411 38的方法合成。产物在乙腈中按照下面反应式进行反应:
反应混合物在冷却下用玻璃漏斗真空过滤,以除去所形成的LiCl副产物。在减压下蒸馏除去溶剂,得到的三(五氟乙基)三氟磷酸1,2-二甲基-3-丙基咪唑鎓在减压下干燥。
实施例3
三(九氟丁基)三氟磷酸1-乙基-3-甲基咪唑鎓的合成
三(九氟丁基)三氟磷酸锂的合成类似于三(五氟乙基)三氟磷酸锂合成。产物在乙腈中按照下面反应式进行反应:
Figure C0112280500182
反应混合物在冷却下用玻璃漏斗真空过滤,以除去所形成的LiCl副产物。在减压下蒸馏除去溶剂,得到的三(九氟丁基)三氟磷酸1-乙基-3-甲基咪唑鎓在减压下干燥。

Claims (9)

1. 通式为下式的离子型液体:
K+A-(I)
其中:
K+为阳离子,选自:
Figure C011228050002C1
其中R1到R5相同或不同,任意选择地通过一单键或双健彼此直接键合,且每个单独或一起具有以下的意义:
-H,
-卤素,
-具有1-8个碳原子的烷基基团,
且A-为选自如下的阴离子:
[PFx(CyF2y+1-zHz)6-x]-
其中1≤x<6
1≤y≤8
0≤z≤2y+1,
而且上述阴离子不包括[(CF3)2PF4]-、[(CF3)3PF3]-、[(CF3)4PF2]-、[(CF3)5PF]-和[(CF3)6P]-
2. 权利要求1的离子型液体,其中阴离子A-是三(五氟乙基)三氟磷酸根或三(九氟丁基)三氟磷酸根。
3. 权利要求1或2的离子型液体,其中杂环阳离子是
Figure C011228050003C1
其中R1到R5相同或不同,每个单独或一起具有以下意义:
-H,或
具有1-8个碳原子的烷基基团。
4. 如权要求1所定义的离子型液体在对质子惰性的溶制的混合物中的用途。
5. 如权利要求1所定义的离子型液体在与选自LiPF6、LiBF4、LiClO4、LiAsF6、LiCF3SO3、LiN(CF3SO2)2、LiC(CF3SO2)3和其混合物的导电性盐的混合物中的用途。
6. 如权利要求1所定义的离子型液体在电化学电池中的用途。
7. 如权利要求1所定义的离子型液体在超级电容器中的用途。
8. 如权利要求1所定义的离子型液体作为溶剂及在催化化学反应中的用途。
9. 如权利要求1所定义的离子型液体作为液压液的用途。
CNB011228059A 2000-06-09 2001-06-08 离子型液体ⅱ Expired - Fee Related CN100413873C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10027995.3 2000-06-09
DE10027995A DE10027995A1 (de) 2000-06-09 2000-06-09 Ionische Flüssigkeiten II

Publications (2)

Publication Number Publication Date
CN1327986A CN1327986A (zh) 2001-12-26
CN100413873C true CN100413873C (zh) 2008-08-27

Family

ID=7644877

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB011228059A Expired - Fee Related CN100413873C (zh) 2000-06-09 2001-06-08 离子型液体ⅱ

Country Status (10)

Country Link
US (1) US7153974B2 (zh)
EP (1) EP1162204B1 (zh)
JP (1) JP5236135B2 (zh)
KR (1) KR100781473B1 (zh)
CN (1) CN100413873C (zh)
BR (1) BR0102318A (zh)
CA (1) CA2349903C (zh)
DE (2) DE10027995A1 (zh)
RU (1) RU2272043C2 (zh)
TW (1) TWI300780B (zh)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10027995A1 (de) * 2000-06-09 2001-12-13 Merck Patent Gmbh Ionische Flüssigkeiten II
KR100473433B1 (ko) * 2000-07-17 2005-03-08 마쯔시다덴기산교 가부시키가이샤 비수전해액 및 그것을 포함하는 비수전해액전지 및 전해콘덴서
DE10038858A1 (de) * 2000-08-04 2002-02-14 Merck Patent Gmbh Fluoralkylphosphate zur Anwendung in elektrochemischen Zellen
DE10055811A1 (de) 2000-11-10 2002-05-29 Merck Patent Gmbh Tetrakisfluoroalkylborat-Salze und deren Verwendung als Leitsalze
EP1205998A2 (de) 2000-11-10 2002-05-15 MERCK PATENT GmbH Elektrolyte
DE10109032A1 (de) * 2001-02-24 2002-09-05 Merck Patent Gmbh Fluoralkylphosphat-Salze und Verfahren zur Herstellung dieser Substanzen
DE10130940A1 (de) * 2001-06-27 2003-01-16 Merck Patent Gmbh Supersäuren, Herstellverfahren und Verwendungen
JP2003313171A (ja) * 2002-04-23 2003-11-06 Kuraray Co Ltd N−アルキル−n’−アルキルイミダゾリウム塩の製造方法
FR2840916B1 (fr) * 2002-06-17 2004-08-20 Inst Francais Du Petrole Procede d'elimination des composes soufres et azotes de coupes hydrocarbonees
AU2003263890A1 (en) 2002-08-16 2004-03-03 Sachem, Inc. Lewis acid ionic liquids
US7750166B2 (en) * 2002-08-16 2010-07-06 University Of South Alabama Ionic liquids containing a sulfonate anion
JP4085986B2 (ja) * 2003-04-01 2008-05-14 ソニー株式会社 電池
DE10325051A1 (de) 2003-06-02 2004-12-23 Merck Patent Gmbh Ionische Flüssigkeiten mit Guanidinium-Kationen
WO2005028446A1 (ja) * 2003-09-18 2005-03-31 Sumitomo Chemical Company, Limited イオン性液体及びそれを使用する反応方法
JP4982083B2 (ja) * 2003-10-10 2012-07-25 出光興産株式会社 潤滑油
JP2005147394A (ja) * 2003-10-23 2005-06-09 Sankyo Seiki Mfg Co Ltd 動圧軸受装置、及び、ディスク駆動装置
JP5376746B2 (ja) * 2003-11-05 2013-12-25 協同油脂株式会社 半固体状潤滑剤組成物
US7423164B2 (en) * 2003-12-31 2008-09-09 Ut-Battelle, Llc Synthesis of ionic liquids
US8715521B2 (en) * 2005-02-04 2014-05-06 E I Du Pont De Nemours And Company Absorption cycle utilizing ionic liquid as working fluid
DE102005007100A1 (de) * 2005-02-16 2006-08-17 Solvent Innovation Gmbh Prozess- bzw. Arbeitsmaschine mit ionischer Flüssigkeit als Betriebsflüssigkeit
JP4926411B2 (ja) * 2005-04-08 2012-05-09 出光興産株式会社 グリース組成物
JP5074687B2 (ja) * 2005-07-15 2012-11-14 出光興産株式会社 含油軸受用潤滑剤
WO2007055324A1 (ja) * 2005-11-14 2007-05-18 The Nippon Synthetic Chemical Industry Co., Ltd. 合成潤滑油
US7737106B2 (en) * 2005-11-29 2010-06-15 The Procter & Gamble Company Process for making an ionic liquid comprising ion actives
US20070129568A1 (en) * 2005-12-06 2007-06-07 Ngimat, Co. Ionic liquids
DE102006005103A1 (de) * 2006-02-04 2007-08-09 Merck Patent Gmbh Oxonium- und Sulfoniumsalze
BRPI0711234A2 (pt) * 2006-05-31 2012-03-20 E.I Du Pont De Mours And Company aparelhos de ajuste de temperatura e processos de ajuste da temperatura
US20080153697A1 (en) * 2006-12-22 2008-06-26 E. I. Dupont De Nemours And Company Mixtures of ammonia and ionic liquids
DE102007004698A1 (de) 2007-01-31 2008-08-07 Merck Patent Gmbh Verbindungen enthaltend Organofluorochlorophosphatanionen
DE102008032825B3 (de) * 2008-07-11 2010-01-14 Siemens Aktiengesellschaft Strahlpumpe sowie Verfahren zu deren Betrieb
JP2010287431A (ja) * 2009-06-11 2010-12-24 Sony Corp 電池
CN102473527B (zh) 2009-08-03 2014-07-30 默克专利有限公司 电解液体系
DE102009058969A1 (de) * 2009-12-18 2011-06-22 Merck Patent GmbH, 64293 Verbindung mit (Perfluoralkyl)fluorohydrogenphosphat - Anionen
US8846922B2 (en) 2010-09-27 2014-09-30 Merck Patent Gmbh Functionalized fluoroalkyl fluorophosphate salts
DE102012006896A1 (de) 2012-04-05 2013-10-10 Merck Patent Gmbh Silikate mit organischen Kationen
EP3772129B1 (de) 2019-07-31 2021-06-30 Innolith Technology AG Auf so2-basierender elektrolyt für eine wiederaufladbare batteriezelle und wiederaufladbare batteriezelle denselben umfassend

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0513278A (ja) * 1991-07-04 1993-01-22 Matsushita Electric Ind Co Ltd 電解コンデンサ駆動用溶融塩形電解質
US5827602A (en) * 1995-06-30 1998-10-27 Covalent Associates Incorporated Hydrophobic ionic liquids
CN1232465A (zh) * 1996-10-05 1999-10-20 默克专利股份有限公司 氟磷酸锂和其作为导电盐的用途

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS612278A (ja) * 1984-06-14 1986-01-08 Mitsui Petrochem Ind Ltd 電池
EP0839139B2 (en) * 1995-06-30 2009-11-18 Covalent Associates Incorporated Hydrophobic ionic liquids
JPH1021914A (ja) * 1996-07-05 1998-01-23 Mitsubishi Chem Corp 非水電解液二次電池
GB9616264D0 (en) * 1996-08-02 1996-09-11 British Nuclear Fuels Plc Reprocessing irradiated fuel
JPH11273734A (ja) * 1998-03-23 1999-10-08 Sanyo Chem Ind Ltd 難燃性非水電解液およびそれを用いた二次電池
DE19910968A1 (de) * 1999-03-12 2000-11-09 Merck Patent Gmbh Anwendung von Additiven in Elektrolyten für elektrochemische Zellen
DE10008955C2 (de) * 2000-02-25 2002-04-25 Merck Patent Gmbh Lithiumfluoralkylphosphate, Verfahren zu ihrer Herstellung und deren Verwendung als Leitsalze
DE10026565A1 (de) * 2000-05-30 2001-12-06 Merck Patent Gmbh Ionische Flüssigkeiten
DE10027995A1 (de) * 2000-06-09 2001-12-13 Merck Patent Gmbh Ionische Flüssigkeiten II

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0513278A (ja) * 1991-07-04 1993-01-22 Matsushita Electric Ind Co Ltd 電解コンデンサ駆動用溶融塩形電解質
US5827602A (en) * 1995-06-30 1998-10-27 Covalent Associates Incorporated Hydrophobic ionic liquids
CN1232465A (zh) * 1996-10-05 1999-10-20 默克专利股份有限公司 氟磷酸锂和其作为导电盐的用途

Also Published As

Publication number Publication date
TWI300780B (en) 2008-09-11
DE10027995A1 (de) 2001-12-13
US7153974B2 (en) 2006-12-26
KR100781473B1 (ko) 2007-12-03
DE50106762D1 (de) 2005-08-25
US20020015884A1 (en) 2002-02-07
JP2002025610A (ja) 2002-01-25
EP1162204A1 (de) 2001-12-12
JP5236135B2 (ja) 2013-07-17
KR20020017934A (ko) 2002-03-07
BR0102318A (pt) 2002-02-13
RU2272043C2 (ru) 2006-03-20
CA2349903C (en) 2010-02-02
EP1162204B1 (de) 2005-07-20
CA2349903A1 (en) 2001-12-09
CN1327986A (zh) 2001-12-26

Similar Documents

Publication Publication Date Title
CN100413873C (zh) 离子型液体ⅱ
JP4611567B2 (ja) イオン性液体
KR100801811B1 (ko) 전기화학 전지용 플루오로알킬 포스페이트
KR20010110330A (ko) 화학 전지용 전해질중의 첨가제인 실란 화합물
JP3728236B2 (ja) テトラキスフルオロアルキルホウ酸塩およびそれらの導電性塩としての使用
US20010033964A1 (en) Alkylspiroborate salts for use in electrochemical cells
US6423454B1 (en) Lithium fluoroalkylphosphates and their use as electrolyte salts
KR20010062269A (ko) 전기화학 전지에 사용하기 위한 알킬스피로보레이트 염
US6893774B2 (en) Fluoroalkylphosphate salts, and process for the preparation of these substances
US20020001755A1 (en) Lithium salt and a process of preparing thereof
JP2002249670A (ja) 電解質
RU2246499C2 (ru) Способ получения литиевых комплексных солей для использования в химических источниках тока
JP2002356491A (ja) フルオロアルキルホスフェートの調製方法
KR20010040169A (ko) 전기화학 전지에 사용하기 위한 착체 염

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20080827

Termination date: 20170608

CF01 Termination of patent right due to non-payment of annual fee