Materials useful as electrolytic solutes
AssigneesACEP Inc., Centre National De La Recherche Scientifique, Universite de Montreal
InventorsChristophe Michot, Michel Armand, Michel Gauthier, Nathalie Ravet
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Abstract
The invention concerns novel ionic compounds with low melting point whereof the onium type cation having at least a heteroatom such as N, O, S or P bearing the positive charge and whereof the anion includes, wholly or partially, at least an ion imidide such as (FX1O)N−(OX2F) wherein X1 and X2 are identical or different and comprise SO or PF, and their use as solvent in electrochemical devices. Said composition comprises a salt wherein the anionic charge is delocalised, and can be used, inter alia, as electrolyte.
Claims23
An ionic compound having a cation of the onium type with at least one heteroatom comprising N, O, S or P bearing the positive charge and the anion including, in whole or in part, at least one imide ion at the type (FX1O)N−(OX2F) wherein X1 and X2 are the same or different and comprise SO or PF, wherein the compound comprises at least an anion selected from Cl−;
- Br−;
- I−;
- NO3−;
- M(R10)4−;
- A(R10)6−;
- R11YO2−;
- R11YONZ1−;
- R11YOCZ2Z3;
- 4,5-dicyano-1,2,3-triazole;
- 3,5-bis(RF)-1,2,4-triazole;
- tricyanomethane;
- pentacyanocyclopentadiene;
- pentakis(trifluoromethyl)cyclopentadiene;
- and barbituric acid, and;
- M is B, Al, Ga or Bi;
- A is P, As and Sb;
- R10 is a halogen;
- R11 represents H, F, alkyl, alkenyl, aryl, arylalkyl, alkylaryl, arylalkenyl, alkenylaryl, dialkylamino, alkoxy or thioalkoxy, each having from 1 to 18 carbon atoms and being unsubstituted or substituted with one or more oxa, thia, or aza substituents, and wherein one or more hydrogen atoms are optionally replaced with halogen in a ratio of 0 to 100%, and eventually being part of polymeric chain;
- Y represents C, SO, S═NCN, S═C(CN)2, PR11, P(NCN)R11, P(C(CN)2)R11, and when Y is P(NCN)R11 or P(C(CN)2)R11, then R11YO2, R11YONZ1, and R11YOCZ2Z3 become R11YO, R11YNZ1, and R11YCZ2Z3, respectively, an alkyl, alkenyl, aryl, arylalkyl, alkylaryl, arylalkenyl, alkenylaryl having from 1 to 18 carbon atoms and optionally substituted by one or more oxa, thia or aza;
- a dialkylamino group N(R11)2;
- Z1, Z2, and Z3 represent independently R11, R11YO or CN, this group being optionally part of a polymeric chain.
A method of using electrolytic composition, comprising the step of:
- carrying out chemical or electrochemical reactions involving soluble species in a medium comprising said electrolytic composition,
- wherein said reactions are selected tram Diels-Alder, Friedel-Craft, mixed aldolization, condensation, polymerization, nucleophilic substitution, and electrophilic substitution reactions,
- and where in said electrolytic composition comprises at least one ionic compound of low melting point having a cation of the onium type with at least one heteroatom selected from N, O, S or P bearing the positive charge and the anion including, in whole or in part, at least one imide ion of the type (FX1O)N−(OX2F), wherein X1 and X3 are the same or different and comprise SO or PF.
A medium used to perform an organic chemistry reaction involving soluble species present in said medium, comprising:
- at least one ionic compound of low melting point comprising a cation of the onium type having at least one heteroatom selected from N, O, S or P carrying a positive charge;
- and
- an anion including, in whole or in part, at least one imide ion of the type (FX1O)N−(OX2F), wherein X1 and X2 are the same or different and comprise SO or PF,
- and wherein such medium is optionally used in combination with at least one other component selected from the group consisting of a metallic salt, a polar polymer, and an aprotic cosolvent,
- and wherein the medium comprises at least one chiral onium cation allowing enantioselective reactions.
A medium used to perform an organic chemistry reaction involving soluble species present in said medium, comprising:
- at least one ionic compound of low melting point comprising a cation of the onium type having at least one heteroatom selected from N, O, S or P carrying a positive charge;
- and
- an anion including, in whole or in part, at least one imide ion of the type (FX1O)N−(OX2F), wherein X1 and X2 are the same or different and comprise SO or PF.
- and wherein such medium is optionally used in combination with at least one other component selected from the group consisting of a metallic salt, a polar polymer, and an aprotic cosolvent,
- and wherein the medium comprises at least one catalytic species.
An electrochemical device having at least two electrodes and one electrolyte, said electrolyte comprising at least one ionic compound of low melting point, comprising:
- a cation of the onium type with at least one heteroatom selected from N, O, S or P carrying a positive charge;
- and
- an anion including, in whole or in part, at least one imide ion of the type (FX1O)N−(OX2F), wherein X1 and X2 are the same or different and comprise SO or PF,
- and wherein the electrolyte comprises at least one anion [B] selected from the group consisting of Cl−;
- Br−;
- I−;
- NO3−;
- M(R10)4−;
- A(R10)6−;
- R11YO2−;
- [R11YONZ1]−;
- [R11YOCZ2Z3]−;
- (R11)2PO 2−;
- (R11)2P(NCN)O−;
- (R11)2P(C(CN)2)O−;
- [(R11)2P(NCN)NZ1]−;
- [(R11)2P(C(CN)2)NZ1]−;
- 4,5-dicyano-1,2,3-triazole;
- 3,5-bis(Rf)-1,2,4-triazole;
- tricyanomethane;
- pentacyanocyclopentadiene;
- pentakis(trifluoromethyl)cyclopentadiene;
- barbituric acid;
- and Meldrum acid derivatives and their substitution products, wherein
- M is B, Al, Ga or Bi;
- A is P, As and Sb;
- R10 is a halogen;
- R11 represents independently H, F, alkyl, alkenyl, aryl, arylalkyl, alkylaryl, arylalkenyl, alkenylaryl, dialkylamino, alkoxy or thioalkoxy, each having from 1 to 18 carbon atoms and being unsubstituted or substituted with one or more oxa, thia, or aza substituents, and wherein one or more hydrogen atoms are optionally replaced with halogen in a ratio of 0 to 100%, and eventually being part of polymeric chain;
- Y represents C, SO, S═NCN, S═C(CN)2, an alkyl, alkenyl, aryl, arylalkyl, alkylaryl, arylalkenyl, alkenylaryl having from 1 to 18 carbon atoms and optionally substituted by one or more oxa, thia, or aza, or a dialkylamino group N(R10)2;
- and
- Z1 to Z3 represent independently R11, R11YO,(R11)2PO, (R11)2P(NCN), (R11) 2P(C(CN)2) or CN, wherein this group is optionally part of a polymeric chain.
An electrochemical device having at least two electrodes and one electrolyte, said electrolyte comprising at least one ionic compound of low melting point comprising:
- a cation of the onium type with at least one heteroatom selected from N, O, S or P carrying a positive charge;
- and
- an anion including, in whole or in part, at least one imide ion of the type (FX1O)N−(OX2F), wherein X1 and X2 are the same or different and comprise SO or PF,
- and wherein the electrolyte is impregnated in a porous membrane.
Dependencies are inferred from the claim text.