Modified ionic liquids containing phosphorus

1. A compound, comprising:

an ionic liquid compound,

an anion comprising an aluminate, arsenide, cyanide, thiocyanate, nitrite, benzoate, chlorate, chlorite, chromate, sulfate, sulfite, silicate, thiosulfate, oxalate, acetate, formate, hydroxide, nitrate, phosphate, imide, or borate; and

a cation attached to a phosphorus moiety according to the formula:

wherein:

A is a CAT + or R 1 ;

B is a CAT + or R 2 ;

CAT + is a pyrrolidinium, piperdinium, azepanium, sulfonium, phosphonium, imidazolium, pyridine or a 5- or 6-membered heterocyclic ring having 1 to 3 heteroatoms as ring members comprising nitrogen, oxygen, silicon or sulfur;

R 1 and R 2 are independently a methyl or C 2 -C 8 alkyl, alkenyl, alkoxy, aryl, alkynyl, alkylsiloxy, silyl, thioether, sulfoxide, azo, amino or silane group, or a phenyl or benzyl, wherein any of the carbon or hydrogen atoms therein are optionally further substituted with a halide, alkyl, alkenyl, alkoxy, aryl, alkynyl, alkylsiloxy, phenyl, benzyl, silyl, thioether, sulfoxide, azo, amino or silane; and

X is (a) a linker, comprising a methylene, C 2 -C 8 alkylene, alkenylene, alkynylene, alkoxy, ester, carbonylene, phenylene, thioether, sulfoxide, azo or aryl group, wherein any of the carbon or hydrogen atoms therein are optionally further substituted with a halide; (b) O, S, N, or C; or (c) O, S, N, or C attached to the linker, with the proviso that when each X is O, then R 1 or R 2 are not methyl or C 2 -C 8 alkyl, R 1 and R 2 do not form a ring with phosphite, and CAT+ is not an imidazolium.

2. The compound of claim 1 , wherein either or both of A and B is CAT+.

3. The compound of claim 1 , wherein either or both of R 1 and R 2 is phenyl, wherein any of the carbon or hydrogen atoms therein are optionally further substituted with a halide, alkyl, alkenyl, alkoxy, aryl, alkynyl, alkylsiloxy, phenyl, benzyl, silyl, thioether, sulfoxide, azo, amino or silane.

4. An electrical energy storage device electrolyte, comprising:

a) an aprotic organic solvent;

b) a metal salt;

c) an additive; and

d) an ionic liquid compound, comprising:

an anion comprising an aluminate, arsenide, cyanide, thiocyanate, nitrite, benzoate, chlorate, chlorite, chromate, sulfate, sulfite, silicate, thiosulfate, oxalate, acetate, formate, hydroxide, nitrate, phosphate, imide, or borate; and

a cation attached to a phosphorus moiety according to the formula:

wherein:

A is a CAT + or R 1 ;

B is a CAT + or R 2 ;

CAT + is a pyrrolidinium, piperdinium, azepanium, sulfonium, phosphonium, imidazolium, pyridine or a 5- or 6-membered heterocyclic ring having 1 to 3 heteroatoms as ring members comprising nitrogen, oxygen, silicon or sulfur;

R 1 and R 2 are independently a methyl or C 2 -C 8 alkyl, alkenyl, alkoxy, aryl, alkynyl, alkylsiloxy, silyl, thioether, sulfoxide, azo, amino or silane group, or a phenyl or benzyl, wherein any of the carbon or hydrogen atoms therein are optionally further substituted with a halide, alkyl, alkenyl, alkoxy, aryl, alkynyl, alkylsiloxy, phenyl, benzyl, silyl, thioether, sulfoxide, azo, amino or silane; and

X is (a) a linker, comprising a methylene, C 2 -C 8 alkylene, alkenylene, alkynylene, alkoxy, ester, carbonylene, phenylene, thioether, sulfoxide, azo or aryl group, wherein any of the carbon or hydrogen atoms therein are optionally further substituted with a halide; (b) O, S, N, or C; or (c) O, S, N, or C attached to the linker, with the proviso that when each X is O, then R 1 or R 2 are not methyl or C 2 -C 8 alkyl, R 1 and R 2 do not form a ring with phhosphite, and CAT+ is not an imidazolium.

5. The electrolyte of claim 4 , wherein the aprotic organic solvent comprises open-chain or cyclic carbonates, carboxylic acid esters, nitrites, ethers, sulfones, ketones, lactones, dioxolanes, glymes, crown ethers, siloxanes, phosphoric acid esters, phosphates, phosphites, mono- or polyphosphazenes or mixtures thereof.

6. The electrolyte of claim 4 , wherein the additive comprises sulfur-containing compounds, phosphorus-containing compounds, boron-containing compounds, silicon-containing compounds, fluorine-containing compounds, nitrogen-containing compounds, compounds containing at least one unsaturated carbon-carbon bond, carboxylic acid anhydrides or the mixtures thereof.

7. The electrolyte of claim 4 , where either or both of A and B is CAT+.

8. The electrolyte of claim 4 , where either or both of R 1 and R 2 is phenyl, wherein any of the carbon or hydrogen atoms therein are optionally further substituted with a halide, alkyl, alkenyl, alkoxy, aryl, alkynyl, alkylsiloxy, phenyl, benzyl, silyl, thioether, sulfoxide, azo, amino or silane.

9. The electrolyte of claim 4 , wherein the cation of the metal salt comprises an alkali metal.

10. The electrolyte of claim 9 , wherein the alkali metal is lithium or sodium.

11. The electrolyte of claim 4 , wherein the cation of the metal salt comprises aluminum or magnesium.