WO2001038319A1 - Dioxolone und ihre verwendung als elektrolyte - Google Patents
Dioxolone und ihre verwendung als elektrolyte Download PDFInfo
- Publication number
- WO2001038319A1 WO2001038319A1 PCT/EP2000/011456 EP0011456W WO0138319A1 WO 2001038319 A1 WO2001038319 A1 WO 2001038319A1 EP 0011456 W EP0011456 W EP 0011456W WO 0138319 A1 WO0138319 A1 WO 0138319A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- general formula
- alkyl
- compounds
- electrolytes
- different
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M6/00—Primary cells; Manufacture thereof
- H01M6/14—Cells with non-aqueous electrolyte
- H01M6/16—Cells with non-aqueous electrolyte with organic electrolyte
- H01M6/162—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte
- H01M6/164—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte by the solvent
Definitions
- the invention relates to a novel use for 1,3-dioxol- (4) -ones and to new dioxolones.
- Lithium batteries have an electrolyte comprising a conductive salt and a non-aqueous solvent.
- a very good conductive salt is LiPF .
- other lithium salts such as LiBF 4 , lithium salts of trifluoromethanesulfonic acid or of bis- (trifluoromethanesulfonyl) iid can also be used.
- solvents used are alkylene carbonates, ethers, formamides, sulfolanes or methylsulfolanes. Certain nitriles or nitrogen-containing compounds such as nitromethane, pyrrolidinones etc. can also be used.
- the object of the present invention was to provide further compounds which can be used as solvents for electrolytes. This object is achieved by the invention.
- the present invention provides compounds of the general formula (I)
- R 1 and R 2 are identical or different and represent hydrogen, Cl-C3-alkyl, Cl-C3-alkyl substituted by one or more halogen atoms and R3 and R4 are identical or different and represent Cl-C3-alkyl or by at least 1 fluorine atom substituted Cl-C3-alkyl are available as solvents, especially in electrolytes of Li batteries.
- R and R are preferably independently of one another hydrogen or methyl.
- R 3 preferably represents methyl
- R 4 preferably represents trifluoromethyl.
- a very particularly preferred compound is 2-trifluoromethyl-2, 5, 5-trimethyl-1, 3-dioxolone- (4).
- the compounds of formula (I) can be used as the sole solvent in electrolytes. It is preferably used together with at least one other aprotic solvent.
- the known solvents for electrolytes can be used as a further solvent. Usable types of solvents are described, for example, in the literature reference by Ue et al. mentioned. Alkylene carbonates, lactones, nitriles and formamides are particularly useful. Mixtures with dialkylamides of fluorinated carboxylic acids, for example N, N-dialkylamides of trifluoroacetic acid, are also very advantageous.
- Alkyl here means C1-C3-alkyl.
- amides of trifluoroacetic acid in which the amide nitrogen is incorporated into a saturated 5-ring or 6-ring system, which can also contain further heteroatoms, are also very useful.
- the amide group can be formed by the pyrrolidinyl, morpholinyl or piperidinyl radical.
- the molar ratio of the compound of formula (I) and the other solvent is in the range from 1: 0.1 to 1:10.
- electrolytes which are a compound of the general formula (I) and a conductive salt included, also subject of the invention.
- Preferred conductive salts include the lithium cation as the cation, although, for example, quaternary ammonium cations are also useful.
- the preferred anion of the conducting salt is the simply negatively charged anion PF 6 , but the simply negatively charged anions BF 4 , CF 3 S0 3 , C10 4 or [N (S0 2 CF 3 ) 2 ] can also be used.
- a further electrolyte solvent is preferably contained in the electrolyte, preferably an alkylene carbonate or an N, N-disubstituted amide of trifluoroacetic acid, such as the abovementioned, in particular N, N-dialkylamide, of trifluoroacetic acid, alkyl preferably being C1-C3-alkyl.
- R 1 and R 2 are identical or different and represent hydrogen, C1-C3-alkyl, C1-C3-alkyl substituted by one or more halogen atoms and R ⁇ and R ⁇ are identical or different and represent C1-C3-alkyl or C1-C3-alkyl substituted by at least 1 fluorine atom, with the proviso that at least 1 halogen atom is contained in the molecule and where R and R are not CF ⁇ Cl or CF 3 at the same time mean.
- R 1 and R 2 are identical or different and represent hydrogen, C1-C3-alkyl, C1-C3-alkyl substituted by one or more halogen atoms
- R ⁇ and R ⁇ are identical or different and represent C1-C3-alkyl or C1-C3-alkyl substituted by at least 1 fluorine atom, with the proviso that at least 1 halogen atom is contained in the molecule and where R and R are not CF ⁇
- the already known compounds of the general formula (I) are prepared by the known production methods.
- the new compounds of the general formula (I) according to the invention are prepared in such a way that ⁇ -hydroxycarboxylic acids of the general formula R ⁇ C (OH) C (O) OH with ketones of the general formula R 3 C (0) R 4 , wherein R 1 , R 2 , R 3 and R 4 have the meaning given above, to give compounds of the general formula (I).
- Catalytic amounts of acid can be added to increase the reaction rate.
- the technology in particular with regard to the range of available solvents, particularly in the case of electrolytes for batteries, is enriched by the invention.
- Dimethylglycolic acid (31.2 g; 0.3 mol; 104 g / mol -1 ) was suspended in trifluoroacetone (200 ml; 250.4 g; 2.23 mol; 112 g mol "1 ; 1.252 g cm -3 ). Excess trifluoroacetone also formed the solvent for the reaction and could be easily recovered by distillation after the reaction was complete.
- LiPF 6 was dissolved in the solvent at 20 ° C.
- the solubility was determined by NMR spectroscopy. It was 1.09 mol LiPF 6 / l.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Secondary Cells (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU23577/01A AU2357701A (en) | 1999-11-24 | 2000-11-17 | Novel use of dioxolones |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1999156363 DE19956363A1 (de) | 1999-11-24 | 1999-11-24 | Neuartige Verwendung von Dioxolonen |
DE19956363.2 | 1999-11-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2001038319A1 true WO2001038319A1 (de) | 2001-05-31 |
WO2001038319A8 WO2001038319A8 (de) | 2001-09-13 |
Family
ID=7930063
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/011456 WO2001038319A1 (de) | 1999-11-24 | 2000-11-17 | Dioxolone und ihre verwendung als elektrolyte |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU2357701A (de) |
DE (1) | DE19956363A1 (de) |
WO (1) | WO2001038319A1 (de) |
Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1263779B (de) * | 1965-08-18 | 1968-03-21 | Basf Ag | Verfahren zur Herstellung von 1, 3-Dioxolan-5-onen |
US4071665A (en) * | 1972-09-18 | 1978-01-31 | E. I. Du Pont De Nemours And Company | High energy density battery with dioxolane based electrolyte |
DD130508A1 (de) * | 1977-04-20 | 1978-04-05 | Peter Czerny | Strahlungsempfindliches material |
DD158650A1 (de) * | 1981-04-28 | 1983-01-26 | Herrmann Matschiner | Verfahren zur herstellung von 2-(2,2-dichlorvinyloxy)-bzw.2-(2,2-dichlervinylthio)-carbonsaeuren sowie ihrer ester |
JPS62219476A (ja) * | 1986-03-20 | 1987-09-26 | Nippon Telegr & Teleph Corp <Ntt> | リチウム二次電池 |
JPS62290070A (ja) * | 1986-06-09 | 1987-12-16 | Matsushita Electric Ind Co Ltd | 有機電解質電池 |
EP0272644A2 (de) * | 1986-12-23 | 1988-06-29 | ZAMBON S.p.A. | Zwischenprodukte und deren Verwendung für die Synthese von organischen Verbindungen |
US4952330A (en) * | 1989-05-25 | 1990-08-28 | Eveready Battery Company, Inc. | Nonaqueous electrolyte |
EP0529802A1 (de) * | 1991-08-13 | 1993-03-03 | Eveready Battery Company | Nichtwässrige Elektrolyten |
JPH0750175A (ja) * | 1993-08-04 | 1995-02-21 | Nippon Telegr & Teleph Corp <Ntt> | 非水溶媒電解質二次電池 |
JPH0750174A (ja) * | 1993-08-04 | 1995-02-21 | Nippon Telegr & Teleph Corp <Ntt> | 非水溶媒電解質二次電池 |
JPH07240232A (ja) * | 1994-01-07 | 1995-09-12 | Sony Corp | 非水電解液二次電池 |
JPH10199567A (ja) * | 1997-01-10 | 1998-07-31 | Hitachi Ltd | 非水電解液二次電池 |
-
1999
- 1999-11-24 DE DE1999156363 patent/DE19956363A1/de not_active Withdrawn
-
2000
- 2000-11-17 AU AU23577/01A patent/AU2357701A/en not_active Abandoned
- 2000-11-17 WO PCT/EP2000/011456 patent/WO2001038319A1/de active Search and Examination
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1263779B (de) * | 1965-08-18 | 1968-03-21 | Basf Ag | Verfahren zur Herstellung von 1, 3-Dioxolan-5-onen |
US4071665A (en) * | 1972-09-18 | 1978-01-31 | E. I. Du Pont De Nemours And Company | High energy density battery with dioxolane based electrolyte |
DD130508A1 (de) * | 1977-04-20 | 1978-04-05 | Peter Czerny | Strahlungsempfindliches material |
DD158650A1 (de) * | 1981-04-28 | 1983-01-26 | Herrmann Matschiner | Verfahren zur herstellung von 2-(2,2-dichlorvinyloxy)-bzw.2-(2,2-dichlervinylthio)-carbonsaeuren sowie ihrer ester |
JPS62219476A (ja) * | 1986-03-20 | 1987-09-26 | Nippon Telegr & Teleph Corp <Ntt> | リチウム二次電池 |
JPS62290070A (ja) * | 1986-06-09 | 1987-12-16 | Matsushita Electric Ind Co Ltd | 有機電解質電池 |
EP0272644A2 (de) * | 1986-12-23 | 1988-06-29 | ZAMBON S.p.A. | Zwischenprodukte und deren Verwendung für die Synthese von organischen Verbindungen |
US4952330A (en) * | 1989-05-25 | 1990-08-28 | Eveready Battery Company, Inc. | Nonaqueous electrolyte |
EP0529802A1 (de) * | 1991-08-13 | 1993-03-03 | Eveready Battery Company | Nichtwässrige Elektrolyten |
JPH0750175A (ja) * | 1993-08-04 | 1995-02-21 | Nippon Telegr & Teleph Corp <Ntt> | 非水溶媒電解質二次電池 |
JPH0750174A (ja) * | 1993-08-04 | 1995-02-21 | Nippon Telegr & Teleph Corp <Ntt> | 非水溶媒電解質二次電池 |
JPH07240232A (ja) * | 1994-01-07 | 1995-09-12 | Sony Corp | 非水電解液二次電池 |
JPH10199567A (ja) * | 1997-01-10 | 1998-07-31 | Hitachi Ltd | 非水電解液二次電池 |
Non-Patent Citations (13)
Title |
---|
A. KONDO ET AL.: "Synthesis of the cyanohydrin of methyl perfluoroheptyl ketone and reaction of the ketone with hydrogen cyanide", JOURNAL OF FLUORINE CHEMISTRY, vol. 26, 1984, pages 59 - 67, XP000926276 * |
F. WEYGAND ET AL.: "2,2-Bis-trifluormethyl-1,3-dioxolone-(4)", CHEMISCHE BERICHTE, vol. 99, 1966, pages 280 - 4, XP002166206 * |
FENG PNZHEN: "Free radical ring opening polymerization of cyclic acrylates", CHINESE JOURNAL OF POLYMER SCIENCE, vol. 10, no. 4, 1992, pages 350 - 5, XP000926274 * |
H. E. SIMMONS ET AL.: "Fluoroketones. I", J. AM. CHEM. SOC., vol. 82, May 1960 (1960-05-01), pages 2288 - 96, XP002166207 * |
I. L. KNUNYANTS ET AL., IZV. AKAD. NAUK SSSR, SER. KHIM., no. 4, 1981, pages 860 - 3, XP000926275 * |
PATENT ABSTRACTS OF JAPAN vol. 012, no. 080 (E - 590) 12 March 1988 (1988-03-12) * |
PATENT ABSTRACTS OF JAPAN vol. 012, no. 187 (E - 615) 31 May 1988 (1988-05-31) * |
PATENT ABSTRACTS OF JAPAN vol. 1995, no. 05 30 June 1995 (1995-06-30) * |
PATENT ABSTRACTS OF JAPAN vol. 1996, no. 01 31 January 1996 (1996-01-31) * |
PATENT ABSTRACTS OF JAPAN vol. 1998, no. 12 31 October 1998 (1998-10-31) * |
UE M ET AL: "ELECTROCHEMICAL PROPERTIES OF ORGANIC LIQUID ELECTROLYTES BASED ON QUATERNARY ONIUM SALTS FOR ELECTRICAL DOUBLE-LAYER CAPACITORS", JOURNAL OF THE ELECTROCHEMICAL SOCIETY,ELECTROCHEMICAL SOCIETY. MANCHESTER, NEW HAMPSHIRE,US, vol. 141, no. 11, November 1994 (1994-11-01), pages 2989 - 2996, XP002911304, ISSN: 0013-4651 * |
V. R. LIKHTEROV ET AL., KHIM. GETEROTSIKL. SOEDIN., no. 10, 1985, pages 1316 - 8, XP000926272 * |
W. J. BAILEY ET AL.: "Free radical ring-opening polymerization of cyclic acrylates", POLYM. PREPR. (AM. CHEM. SOC., DIV. POLYM. CHEM., vol. 28, no. 1, 1987, pages 154 - 5, XP000926273 * |
Also Published As
Publication number | Publication date |
---|---|
AU2357701A (en) | 2001-06-04 |
DE19956363A1 (de) | 2001-05-31 |
WO2001038319A8 (de) | 2001-09-13 |
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