Ionic compounds having a silyloxy group

Patent metadata

Field	Value
Publication number	US-9969757-B2
Application number	US-201314390638-A
Country	US
Kind code	B2
Filing date	Apr 5, 2013
Priority date	Apr 5, 2012
Publication date	May 15, 2018
Grant date	May 15, 2018

Abstract

There is provided an ionic compound having attached thereto a silyloxy group. There is also provided methods of making this ionic compound as well as electrolytes, electrochemical cells and capacitors comprising this ionic compound.

First claim

The invention claimed is:

1. A lithium or lithium-ion battery electrolyte consisting of a conducting lithium salt dissolved in at least one ionic liquid of formula (I), and optionally up to 15 wt %, based on the total weight of the electrolyte, of one or more unsaturated carbonate,
the ionic liquid of formula (I) being:

wherein:
CAT + represents a cation containing a positively singled charged atom, which is nitrogen, phosphorus or sulfur;
R, R 1 and R 2 are independently C 1 -C 8 alkyl, alkenyl or alkynyl groups,
L represents a linker and is a C 1 -C 12 alkylene, alkenylene, or alkynylene group, optionally comprising one or more ether function, and optionally substituted with one or more halogen atoms, and
ANI − represents an anion.

2. The electrolyte of claim 1 , wherein L together with the oxygen atom to which it is attached form one or more alkyleneoxy group.

3. The electrolyte of claim 1 , wherein the positively charged atom is nitrogen.

4. The electrolyte of claim 1 , wherein the cation is of formula (IIIa), (IIIb), or (IIIc):

wherein:
X is —CH 2 —CH 2 —CH 2 —,
—CH 2 —C(═O)—CH 2 —CH 2 —,
—CH 2 —CH 2 —C(═O)—CH 2 —,
—N(alkyl)-CH 2 —CH 2 —CH 2 —,
—CH 2 —CH 2 —CH 2 —N(alkyl)-,
—CH 2 —N(alkyl)-CH 2 —CH 2 —,
—CH 2 —CH 2 —N(alkyl)-CH 2 —,
—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —,
—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —,
—CH 2 —CH 2 —O—CH 2 —CH 2 —,
—CH 2 —O—CH 2 —CH 2 —CH 2 —,
—CH 2 —CH 2 —CH 2 —O—CH 2 —,
—CH 2 —CH 2 —N(alkyl)-CH 2 —CH 2 —,
—CH 2 —N(alkyl)-CH 2 —CH 2 —CH 2 —,
—CH 2 —CH 2 —CH 2 —N(alkyl)-CH 2 —,
—N(alkyl)-CH 2 —CH 2 —CH 2 —CH 2 —, or
—CH 2 —CH 2 —CH 2 —CH 2 —N(alkyl)-; and
R 6 is a C 1 -C 16 alkyl, alkenyl, or alkynyl group.

5. The electrolyte of claim 1 , wherein the cation is of formula (IVa), (IVb), or (IVc):

wherein:
for IVa, Z is —CH═CH—, —CH 2 —CH 2 —CH 2 —, —CH═CH—CH═CH—CH 2 —,
—N═CH—CH═CH—, —CH═N—CH═CH—, —N(alkyl)-CH═CH—,
—CH 2 —CH═CH—O—, ═CH—CH 2 —CH 2 —O—, —O—CH 2 —CH═CH—, —O—CH═CH—CH 2 —,
—CH═CH—O—CH 2 —, ═CH—CH 2 —O—CH 2 —, —CH 2 —O—CH═CH—, ═CH—O—CH 2 —CH 2 —, or
—N(alkyl)-N═CH—,
for IVb, Z is —CH═CH—, and
for IVc, Z is —N(alkyl)-CH═CH—; and
R 7 is hydrogen or alkyl.

6. The electrolyte of claim 1 , wherein the cation is of formula (IIa), (IIb) or (IIc):

wherein R 3 , R 4 and R 5 are independently C 1 -C 16 alkyl, alkenyl, or alkynyl groups.

7. The electrolyte of claim 6 , wherein the cation is a formula (IIa).

8. The electrolyte of claim 1 , wherein the anion is:
a halide,
perchlorate,
hexafluorophosphate,
tris(pentafluoroethyl)trifluorophosphate,
tetrafluoroborate,
trifluoromethyltrifluoroborate,
pentafluoroethyltrifluoroborate,
heptafluoropropyltrifluoroborate,
nonafluorobutyltrifluoroborate,
trifluoromethanesulfonate,
trifluoroacetate,
bis(fluorosulfonyl)amide,
or a sulfonylamide of formula (V):
A-N − —SO 2 —B  (V),

wherein A is F—SO 2 —, CF 3 —SO 2 —, C 2 F 5 —SO 2 —, C 3 F 7 —SO 2 —, C 4 F 9 —SO 2 —, or CF 3 —C(═O)—; and B is —F, —CF 3 , —C 2 F 5 , —C 3 F 7 , —C 4 F 9 ; N is Nitrogen; and S is Sulfur.

9. The electrolyte of claim 8 , wherein the sulfonylamide of formula (V) is:
bis(trifluoromethanesulfonyl)amide,
bis(pentafluoroethylsulfonyl)amide,
bis(heptafluoropropylsulfonyl)amide,
bis(nonafluorobutylsulfonyl)amide,
N-trifluoroacetyl-fluorosulfonylamide,
N-trifluoroacetyl-trifluoromethanesulfonylamide,
N-trifluoroacetyl-pentafluoroethylsulfonyl amide,
N-trifluoroacetyl-heptafluoropropylsulfonylamide,
N-trifluoroacetyl-nonafluorobutylsulfonylamide,
N-fluorosulfonyl-trifluoromethanesulfonylamide,
N-fluorosulfonyl-pentafluoroethylsulfonylamide,
N-fluorosulfonyl-heptafluoropropylsulfonylamide,
N-fluorosulfonyl-nonafluorobutylsulfonylamide,
N-trifluoromethanesulfonyl-pentafluoroethylsulfonyl amide,
N-trifluoromethanesulfonyl-heptafluoropropylsulfonylamide, or
N-trifluoromethanesulfonyl-nonafluorobutylsulfonylamide.

10. The electrolyte of claim 1 , wherein the one or more unsaturated carbonate are absent.

11. The electrolyte of claim 1 , wherein the one or more unsaturated carbonate are present.

12. The electrolyte of claim 11 , wherein the one or more unsaturated carbonate is vinylene carbonate.

13. The electrolyte of claim 1 , wherein the ionic liquid comprises:

14. The electrolyte of claim 1 , wherein the ionic liquid comprises:

15. The electrolyte of claim 1 , wherein
CAT + represents a cation of formula (IIa):

wherein R 3 , R 4 and R 5 are independently C 1 -C 6 alkyl groups;
R, R 1 and R 2 are independently C 1 -C 4 alkyl groups;
L together with the oxygen atom to which it is attached form one or two ethyleneoxy groups; and
ANI − represents a sulfonylamide anion of formula (V):
A-N − —SO 2 —B  (V),

wherein A is F—SO 2 —, CF 3 —SO 2 —, C 2 F 5 —SO 2 —, C 3 F 7 —SO 2 —, C 4 F 9 —SO 2 —; and B is —F, —CF 3 , —C 2 F 5 , —C 3 F 7 , —C 4 F 9 .

16. The electrolyte of claim 15 , wherein R 3 , R 4 and R 5 are independently C 1 -C 3 alkyl groups.

17. The electrolyte of claim 15 , wherein R, R 1 and R 2 are independently C 1 -C 2 alkyl groups.

18. The electrolyte of claim 15 , wherein the anion is bis(fluorosulfonyl)amide, bis(trifluoromethanesulfonyl)amide, or N-fluorosulfonyl-trifluoro-methanesulfonylamide.

19. An electrochemical cell comprising an anode, a cathode, and an electrolyte as defined in claim 1 .

20. The electrochemical cell of claim 19 , wherein the anode is a graphite electrode.

Assignees

• Hydro Quebec
• Hydro Quebec

Inventors

• Kozelj Matjaz
• Guerfi Abdelbast
• Trottier Julie
• Zaghib Karim

Classifications

• H01G9/022

  Electrolytes; Absorbents · CPC title

• H01G9/145

  Liquid electrolytic capacitors (H01G11/00 takes precedence) · CPC title

• H01M2300/0045

  Room temperature molten salts comprising at least one organic ion · CPC title

• H01M10/052

  Li-accumulators · CPC title

• C07C307/00 Primary

  Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups · CPC title